As a reminder: Path Nine is a newsletter for people building their next chapter of work.

Let me interrupt you for a second.

You’re thinking about it, aren’t you?

Maybe you’ve been thinking about it for a while.

You have an idea, or at least the kernel of one.

You’re looking out the window and wondering whether it’s time to take the leap.

Before you do, I want to share something nobody told me when I started.

You picked a complicated moment to want this.

There’s a particular anxiety loose in the culture right now.

The old dream was: get in early, ride the wave, then bet on yourself.

It ran—off and on—for about two decades before it started fraying at the edges. Now the cultural energy has shifted, and fewer people are asking “what are you building?”. Instead, they’re asking—or at least they’re thinking—”are you safe?”

“If the brag used to be the bet, now it’s about having the best safety net you can get. Stability is the new status.” - ,

You can feel it everywhere.

The smartest people you know are taking jobs at the biggest ships they can find—the AI labs, well-funded platforms, companies that look like they’ll weather whatever comes next. And while they board their ships and talk about optionality and proximity to leadership, you’re sitting with a different instinct: I want to make something of my own.

That instinct, right now, requires swimming (very hard) against a (very) strong current.

Every flock has one that wanders.

The other ninety-nine can’t understand why—and they don’t have to.

Which means that what happens next—the silence, hesitation, or concern from the people around you—may hit you even harder.

Harder than it should.

So if you’re thinking about making that bold leap, here are some things to know.

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The people you expect in your corner might not show.

Not at the beginning. Not yet.

You assume that when you finally make the leap, they’ll be the first ones in.

They won’t.

You’ll get silence. Or worse,

“interesting…”,

“oh cool…”, or

“I’ll def check it out…”

said in a tone that means the exact opposite.

You’ll get unsolicited advice on why the timing is wrong, the market is hard, the window has closed.

You’ll get the “You know what you should do…” suggestions which is actually what they’d do, masquerading as advice.

You’ll get a particular kind of attention—watchful, patient, judging—that quietly questions: how long before you come back to reality?

What you won’t get, at first, is anyone simply saying: yes, go.

I’ve done this a few times now. Textbook reselling out of my college dorm. A social movie app that was basically Letterboxd before Letterboxd existed. An IoT agency (I mean, why?), an AI analytics company, a product studio. And every single time, I assumed the world would ignore it, at least for a while. That part just comes with the territory.

Now, before I go any further, I want to make one thing clear: none of this is a complaint.

These are just the conditions. Knowing them in advance is the whole point.

Here's the part that caught me off guard: past support simply didn’t translate into future support. The ones with front-row seats to everything you'd built. They stayed in their chairs.

Instead: nothing.

Or worse—that word. Interesting...

And your own brain—familiar and unreliable—turning their doubt into yours:

Maybe they’re right.

Maybe this is the thing that exposes me.

Maybe I should go back.

Maybe…

The silence has a source.

They’ve made a quiet commitment to a different kind of life, and your leap can unsettle that. Not because they actively wish you harm, but because a choice, once made, needs to stay made. If you succeed, it opens a door they’d prefer stay closed.

Maybe they chose the stable job, the safe career, or the sensible path. Maybe they chose the stable job, the safe(r) career, or the sensible path. Some people find stability by staying still. Others find it by moving. Neither is wrong. But they’re running completely different equations.

If you succeed, it forces a question many haven’t had to ask: could they have done something like this too?

They may not know the answer. And not knowing can be destabilizing.

Your failure makes the hard question go away. Your success keeps it open.

So without realizing it, many of them are quietly hoping for the version of this story where you come back to the shared reality.

But not because they dislike you.

Some of them genuinely love you and want to support you.

And yet, they still can’t bring themselves to say go. Because your failure confirms their script. Your struggle becomes the evidence they were right to stay put. Their judgment remains intact and their story is secured. And through it, so is yours.

This dynamic isn’t new, but it’s definitely heightened. Because now the culture is actively, loudly advocating for the safe choice. The signals say: this is a dangerous time to leave safe harbor and go it alone. Veering from the known path isn’t a sign of courage, it’s a death certificate.

But they’ve made a quiet bet of their own— and your success would force them to reckon with it.

It isn’t a verdict, but you won’t know that…yet.

It’s part of why they watch instead of help. It’s part of why the encouragement tends to come only after the success. The “oh yeah, I always thought that was a great idea” or “I always knew you could do it” that arrives once backing you costs them nothing, once your success is confirmed and safe to claim.

A luxury belief in reverse: free to hold once the risk is gone.

And this is why, at the start, when your thing is most fragile and you are most uncertain, their skepticism can feel like reality itself.

The silence isn’t a signal about your idea.

It’s a signal about their relationship with risk.

For once in history, “it’s not you, it’s me” is actually the honest answer.

People who’ve never taken this kind of bet don’t have the tools to evaluate one.

They can only measure what already exists and is known: salaries, job titles, press releases, social posts, names on buildings. As Nassim Taleb reminds astutely observed,

“The three most harmful addictions are heroin, carbohydrates, and a monthly salary.”

Salaries are a powerful sedative.

They have no framework for the version of you that hasn’t arrived yet. They can’t see it because they’ve never had to picture that version of themselves.

Their doubt is not data.

There’s something simpler underneath all of this.

When you leave the default path, people don’t just doubt your idea, they doubt the departure itself. Off-path looks like off-course to someone who’s never left the road, let alone considered other roads might exist.

What you have to learn to hold onto: what looks strange to them might look completely right to you. Not reckless. Not naive. Just different.

It will only look right to them once you’ve made it through. Which means you have to carry it alone, as a conviction, before it ever becomes accepted as fact.

This is the thing that takes longest to learn: the people best positioned to validate your idea— colleagues, peers, your closest professional network—are often the worst sources of early signal. They’re measuring you against what you were, not what you’re building toward. They’re looking at the path you were on, not the path you’re forging.

And they’re doing it from inside the very system you’re trying to exit.

The tragedy is how many people read that silence as confirmation.

I’ve been there many times. You start to think: if the people who know me best won’t get behind this, maybe I’m wrong. And then, naturally, you start to pull back. You return to the safe road and shelve the thing that was only just getting started.

Potential dies in the premature retreat, not failure.

This part is lonely on purpose.

Belief doesn’t arrive before the proof. It arrives after.

After you prove to yourself you can persevere.

After you learn to sit with silence.

After you realize no one is going to tell you you’re ready.

There’s no version of this where you wait for permission and then leap. The leap happens in the dark, before anyone gets behind you, before you have real, concrete evidence it’s going to work, while the people around you are busy finding shelter somewhere else.

You have to go first.

Sometimes on gut, sometimes on data. Ideally on both.

So you keep going. Not because you’re certain it works.

You keep going because the only way to find out is to go through.

The ones who make it aren’t less scared, and they’re not smarter about the odds. They’re just less dependent on permission. They stopped waiting for the world to validate their intuition—they did it themselves.

They learned the silence is neither a verdict nor a signal of failure.

It’s just how every real thing begins.

Go.

Until next time

If this landed for you, subscribe and pass it to one person who’d appreciate it.

I always enjoy hearing from you, so share your reactions, reflections, and comments.

Thanks for reading,

— Kevin K.

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A little over two years ago, my wife and I spent countless nights hunched over blueprints of our dream house. We were building a house in a quiet town a few hours outside Seattle. It felt like the perfect place—safe, slow, and calm. It was the kind of choice that seemed obvious during COVID when so many were rushing to trade chaotic cities for simpler living.

But our conversations weren’t really about the house, or at least not only about the house.

We were talking about the life we believed we wanted.

The house we were building was falling apart almost as fast as we were building. We’d unintentionally found ourselves locked in with a builder who just couldn’t get the job done. I wrote a little about it a few years ago when we were in the thick of it.

I still remember that snowy day, walking up the long driveway toward what should have been our dream home. As I got closer, all I saw were the flaws. A misplaced stair nearly tripped me up. I found a wall so poorly finished that sunlight streamed through its edges. A supposedly secure window wall shifted if I so much as nudged it.

Everywhere I looked, there were problems:

• A bowed roof weighed heavy with snow, sagging because the builder replaced trusses without approval.

• Beams slanted awkwardly across picture windows, clearly deviating from the plans.

• A large opening sat empty because the custom glass didn’t fit—it was never built to spec.

The house—and the dream—felt like it was crumbling. Literally.

And then, right on cue, our perception of that little quaint town began to unravel too.

What once charmed us on weekend visits soon became constant reminders that we’d made a wrong turn. Our evenings, once filled with friends and energy, had become an endless stream of nothing-nights.

Remote work let me keep my job from a picturesque mountaintop, but it also shrank my friendships down to green Slack dots, messages, and video chats.

The pings kept coming. The people didn’t.

Here’s the thing nobody tells you about moving somewhere with no community or network: The shine always wears off, it’s only a matter of time.

I know this better than most. Moving has become my accidental expertise—my wife and I have changed homes roughly every 18 months for the past decade.

I used to love it. Each move felt like hitting the reset button on life. It felt like changing seasons: new street, new home, new possibilities.

But after your tenth move (hopefully sooner), you start to see the pattern.

That new place energy has a shelf life.

And there’s a machine that keeps us focused on it, chasing it, wanting it.

The machine loves to remind you that you’re one small step away from a reset. All you have to do it is follow the novelty: new listings, new cities, new jobs, same emptiness.

And what’s left when the screens fade to black is what actually lights us up.

This realization hits different people at different times and in different ways. For some, it’s six months into a dream job. For others, it’s after moving to a city they’ve romanticized for years. The specifics change, but the feeling is universal:

“Is this really it?”

But that moment is actually very useful.

When you stop chasing the high of new beginnings, you can finally see what you truly need.

I used to think a better job would fix my Sunday Scaries and Monday morning dread, or a new city would transform me from a homebody into an ‘natural extrovert’ (whatever that means).

It’s the classic fresh start fallacy: mistaking movement for meaning.

The truth is messier and simpler: changing your location doesn’t change who you are, only where you are.

So when my wife and I started planning our next move, we did things differently. Sure, we made a spreadsheet (we work in tech after all; it’s in our DNA). We listed all the usual suspects: schools, walkability, housing market, airport access, and so on.

But after all that analysis, we realized there are really only a couple things that make a place livable:

1. People you can hug without booking a flight, and

2. work that creates pathways for meaning and connection.

And if we’re being honest, anything work-related is a very distant second in that list.

There was a harsh truth we’d been avoiding for years.

We’d moved away from everyone we loved for a dream that turned out to be just that—a mirage.

Living in a perfect house in a perfect town means nothing if you’re surrounded by empty spaces where your people should be. When the walls reflect back only your voice, the faint whispers of what once was become truly deafening.

Once we admitted this to ourselves, the decision was simple. Hard, but simple.

Coming Home

Eventually, it became clear: we had to move back to Seattle.

My wife was 18 weeks pregnant. Our half-built house was still a mess of permits and problems. At first, her job was the practical reason to come back. But over time, it felt like something deeper was pulling us back: back to people we missed, back to a place that knew our names, back to a life that didn’t require reinvention to feel alive.

I realized that what I wanted wasn’t what I needed. The house I’d imagined—a house that symbolized so much—couldn’t shelter us nearly as well as our tangled web of laughter, support, and shared history. Ultimately, we traded the unresolved blueprints and dreams for something stronger: a place where we truly belonged.

This wasn’t easy.

We’d poured years and savings into a vision. Leaving felt in a lot of ways like failure.

But the cost of staying was much higher than the feeling of failure.

Leaving was the only way to rebuild something of value. Something deep. Something meaningful. Something that can’t be replaced.

You can’t get the body without the 5am workout.

You don’t get the health without saying no to the unhealthy diet.

You don’t get the life without choosing the hard thing over the shiny new thing.

Nothing worth building comes easy.

Whether it’s a home, a life, or a career—everything takes work.

And the work doesn’t always lead us where we expect it to.

We’ve now moved into a new house in Seattle. It still isn’t fully “settled.” Despite buying it almost a year ago, we’re still missing furniture and dealing with unorganized cupboards, drawers, and closets. There are little corners that still feel temporary.

And yet, it feels more like home than anything we knew prior.

I still work in a browser tab (for now), but now friends and family can knock, not just ping me.

The secret to choosing where to live isn’t finding the perfect place or checking all the right boxes on a spreadsheet. It’s being honest about what actually sustains you, what connects you, and what lets you build a life without needing a reset every 18 months.

Usually, it’s not the view or the weather (no one ever really picks the Seattle rain) or the size of the house.

It’s the people you share it with.

Everything else is just backdrop.

Until Next Time!

That’s it for this week.

If you enjoyed this piece, I hope you’ll share it or subscribe. This newsletter—and my ego— runs on overpriced whiskey and reader engagement.

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Thanks for reading, and see you soon,

— Kevin K. (@kkirkpatrick)

Not because I care about football—my wife and I are terrible fans. And not because of the halftime show, though it was incredible, even if I could only catch it in the ten-second windows between chasing my toddler around the house.

We’re Seattleites, so watching the Seahawks at their professional peak is practically municipal law. We gathered a few friends, filled every available counter space with snacks, and leaned into the ritual. Football culture. Or close enough.

And for a few hours, everything else stopped.

No work. No emails. No Slack pings.

As I watched the Seahawks hold back the Patriots, I realized that for the first time in months, I felt un-needed. I wasn’t checking Slack. I wasn’t tinkering on a side project. I wasn’t doom-scrolling. I was just... watching. Sitting. Being. Along with 120 million other people.

And I realized how rare that is—how rare the collective pause has become. Not the football. The permission. The feeling that for a few hours, nobody needed anything from me (or anyone else, maybe).

What felt so good wasn’t the game—it was sharing a moment at the same time, with no pressure to optimize it. We’ve lost our shared tempo. And that loss is deeper than missing a show: it’s about the disappearance of what I’ve come to think of as cultural third places—synchronized rituals that made being unreachable feel normal. When they vanish, work fills the void. Without meaning to, we’ve let it become the only tempo we share.

This is what we’ve lost. It’s time to bring it back.

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The fragmentation problem

This isn’t a plea to go back to three TV channels. It’s a plea to rebuild the shared rituals that let us exhale together.

We’ve abandoned something valuable in the march to endless personalization and on-demand content: the synchronized experience. The live moment you plan around, anticipate, and collectively share. The kind that doesn’t demand you curate, optimize, or justify your attention. This isn’t about conformity—it’s about connection.

In 1983, the MASH finale drew 83 million viewers—90% of American households gathered around a single story at the same moment. Nothing today comes close. Netflix alone added 589 original titles in 2024. Spotify serves up algorithmically personalized playlists. TikTok’s For You page shows you a feed that literally no one else will ever see.

The shift accelerated fast. By December 2025, Nielsen reported that streaming captured 47.5% of all TV viewing—a record—while cable dropped to just 20.2%, its lowest point ever. The shared screen splintered into millions of individual ones.

We’ve been sold fragmentation as freedom. More choices. More personalization. More you. But it’s come at a cost: no shared focus, fewer communal conversations, and an ever-shrinking window in which you and a colleague might have watched the same thing.

We’ve optimized for individual engagement and lost our collective rhythm in the process.

Work: the everything place

The default setting of modern life is: you are interruptible.

Used to be a weird ad on Super Bowl Sunday could dominate Monday’s chatter. Now the people you sit next to all have different digital lives, curated exclusively for them. A 2024 Gallup report found one in five employees feels lonely—for remote workers, it was worse. We’ve created a generation of workers who are endlessly productive but wildly disconnected.

Without shared rituals, boundaries evaporate. Work creeps into everything because there’s no structure pushing back. Slack’s Workforce Index found that employees who log off at the end of the day show 20% higher productivity than those who feel obligated to work after hours. The always-on culture doesn’t even deliver what it promises. It just burns us out faster.

When shared cultural scaffolding disappears, something replaces it, but poorly. Work becomes our everything place: our tether to belonging, structure, and identity. But unlike community, work’s rewards are conditional:

• You belong as long as you perform

• Your identity is as fragile as your job security

• When layoffs land, you lose more than your paycheck, you lose your people

Even work can’t carry the weight we’ve placed on it.

The third place

In 1989, sociologist Ray Oldenburg coined the term “third place”—a space that isn’t home (first place) or work (second place), but somewhere else entirely. The café. The barbershop. The pub. The park bench. The library. Third places are defined by their leveling effect: status doesn’t matter, you’re not performing or producing, and the only price of admission is showing up.

We’ve been losing them for decades. Robert Putnam documented this in Bowling Alone—the steady erosion of civic life, community organizations, and the casual gathering spots that held neighborhoods together. Starbucks replaced the local café. Remote work emptied the office hallway. Suburban sprawl turned walkable gathering spots into parking lots.

But here’s what I’ve come to realize: we didn’t just lose physical third places. We lost cultural ones too.

Think about what the Super Bowl actually is. For three hours, 120 million people occupy the same cultural space. The game becomes the gathering place. The halftime show becomes the town square. You’re not competing or optimizing—just existing alongside millions of others in a shared moment. That’s a third place. Not a physical one, but a cultural one. And one of the last moments where the attention airspace clears—not by discipline, but by cultural permission.

We’re not just craving connection. We’re craving the safety that third places provide. In those spaces—physical or cultural—you don’t have to signal your taste or build your brand. You just are, unshackled from identity curation. Your choice to watch the same thing as everyone else stops being a statement about who you are. It becomes permission to just be there.

Émile Durkheim called this “collective effervescence”—the energy that emerges when a group shares a common focus at the same moment. It’s the same force behind concerts, stadium crowds, and packed dance floors. Algorithms can personalize your experience endlessly. They can’t manufacture that.

The MASH finale wasn’t just television. It was a town square for 83 million people. That’s what shared tempo built: cultural third places where showing up was the only requirement.

We’re running out of moments like this—places where it’s normal to be unreachable, where nobody even tries, because everyone’s in sync. Holidays used to do this well: not because the day was sacred, but because expectations dropped to zero. Nobody emailed on Christmas morning. Nobody Slacked on Thanksgiving. The shared ritual created a collective buffer that no individual boundaries conversation ever could. That’s what cultural third places do at their best—they don’t just bring us together. They synchronize our absence.

As work becomes more fragmented and precarious—as teams shrink, as the solo-creator economy grows—the need for cultural third places only intensifies. The Sunday scaries aren’t just about dreading Monday. They’re about facing another week without a place—physical or cultural—where you can stop being a professional and just be a person.

Rebuilding the third place

The hunger for shared tempo didn’t disappear—it just moved.

Twitch and Discord built massive communities around synchronous shared attention; millions watching the same stream, reacting together in real time. The resurgence of live events, from local comedy nights to community watch parties, reflects a craving for physical shared tempo. Even Spotify Wrapped works because it mass-synchronizes a cultural moment—everyone posting, comparing, and arguing about their results on the same day.

These are cultural third places. Not physical, but relational—built on shared rituals and synchronous attention.

We don’t need to go back to a world where everyone watches the same thing. We need shared rituals at the scale of a neighborhood, a workplace, a friend group. A team that watches the same documentary and talks about it on Monday. A community channel dedicated to a weekly live event. A block that gathers for the same meal once a month.

The key is reducing coordination friction—creating defaults that run without renegotiation. The Super Bowl works because it’s pre-coordinated. Nobody sends a group text asking “so are we watching?” Most shared rituals we’ve lost failed not because people stopped wanting them, but because every gathering became an individual logistics problem.

If it requires a group text every time, it isn’t a ritual yet. Make it recurring so your future self doesn’t have to renegotiate it. One or two anchors is enough. Lower the bar—the rhythm matters more than the quality.

The platforms and infrastructure exist. The question is whether we use them to extract attention or build connection.

Less, but better

AI is already pushing beyond the typical tech world and into every corner of how we live and work. More personalization. More noise. More addressability. The attention airspace is about to get a lot more crowded.

That means shared tempo becomes more valuable, not less. And the risk gets starker: if we don’t rebuild cultural third places, work will become the only organizing system left—the only place we get community, structure, identity, and rhythm. That’s not just unsustainable. It’s fragile.

Dieter Rams, the legendary industrial designer, had a principle: less, but better. We talk endlessly about portfolio careers—multiple income streams, side hustles, fractional roles. Fine. But we need portfolio lives. Lives with enough texture and dimension that our entire identity doesn’t collapse when a project fails or a job disappears.

That means building cultural third places deliberately. Deep hobbies you embrace for their own sake, not ones you monetize on YouTube. Experiences that exist outside a screen. And most of all, shared rituals you commit to on a recurring basis: the weekly dinner, the pickup game, the neighborhood show where everyone knows the band is mediocre but shows up anyway. These aren’t luxuries or nice-to-haves. They’re the third places we build when the old ones disappear.

The benefit of shared tempo was never the halftime show itself. It was what the halftime show created: a cultural third place where 120 million people had permission to care about something outside of work. Something that brought joy, health, and a kind of wealth we’ve stopped measuring.

Protect your attention airspace. Rebuild your shared tempo. The third place isn’t coming back on its own—we have to build it.

Until next time

If this landed for you, subscribe and pass it to one person who’d appreciate it.

I always enjoy hearing from you, so share your reactions, reflections, and/or questions.

Thanks for reading, and see you soon,

— Kevin K.

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Welcome to the 32 new subscribers—thanks for joining! As a reminder: Path Nine is a newsletter written by Kevin K. It features meditations on work, productivity, tech, and entrepreneurship.

For the last year or so, I’ve been off. Not off work, off parenting, or off life—just off line. I didn’t post. I didn’t write. I didn’t ‘share’ anything.

Offline, didn’t mean disappearing. It meant refusing to turn my life into output.

Maybe you noticed. If you did, I hope it’s because you missed something we shared in the words I sent out; a connection, a shared longing, or a feeling of same-ness.

Maybe you didn’t notice. That’s okay too.

For me, the quiet was the point.

In the first frame: quiet, undisturbed.

Creating space

The funny thing about stepping back from digital noise is that it sharpens everything else. By turning down the volume of constant connectivity, I found I could finally turn up the volume on everything else.

I’m no longer distracted by the noise.

When I’m with friends, I’m actually with them. I’ve stopped reaching for my phone during silent moments, because those moments are rich with possibility, not something to escape.

Even more importantly, clearing the mental clutter opened space in my mind, a space I hadn’t realized was missing. And in that space, I could finally breathe.

And it turns out it’s not just my own feeling. A randomized trial last year blocked mobile internet on participants’ phones for two weeks and found sustained attention improved—about as much as being a decade younger.

In the next frame: morning light at a window. Nothing to check. Nothing to miss.

Building fortitude

It’s actually quite difficult to stay offline. It requires effort, in a way that feels unnatural to most of us these days. The easy thing is to pick up a device, and just let it take you away—no thoughts, no directions, just subtle pulls toward the most compelling notification or signal in that moment.

Resistance, though, is power. In resisting, we challenge the assumptions and incentives of the worlds we exist in online. And incentives are everything. Rewiring our own incentives requires intense focus and fortitude.

There’s a particular allure to being noticed online. Even if you’re not aiming for “fame,” the likes, comments, and reposts create small wins that become addictive.

When that stream quiets, you feel the absence. There’s a void. And what you fill that void with matters.

At first, the urge to check, to scroll, didn’t disappear. But letting that feeling linger taught me something: those empty moments are opportunities. They made me reach out to people in real life, or dig deeper into meaningful content in books and articles, instead of taking the easy win of a quick dopamine hit.

Being here—fully present—takes effort, but the rewards go far beyond what any fleeting notification ever could.

In the next frame: a line at a café. A calm observance of the surrounding architecture.

Reclaiming privacy

I’ve always loved writing and sharing ideas. It’s what drew me to the internet in the first place. But over time, sharing became performance.

Everything we post now feels optimized. We measure our worth in likes, comments, and shares. The algorithms quietly train us to package our lives for engagement or relevance, and that pressure seeps in everywhere.

That’s part of why I struggled to post. I don’t feel compelled to tell you every single moment of my life. I just don’t.

When I stopped posting on Instagram years ago, I felt strange at first, just lurking. But now it feels sane. I’m not only guarding my own clarity; I’m preserving my family’s privacy.

That simple act of stepping away felt freeing, more than I’d expected. Instead of worrying about crafting the “perfect” post, I could focus on living—and that’s a trade-off I’ll choose every time.

In the next frame: a moment that never becomes content. It remains intact.

Making Time

I’ve never been one to waste time. I’ve always unintentionally lived by the mantra: “Every minute matters.” But when I became a parent, my view on time shifted.

When your day is measured in bedtime stories, scraped knees, and first steps, everything changes. Productivity becomes secondary to presence. My child doesn’t care if I draft another post or sign off on one more task. She notices if I’m truly there—connected and happy.

Anything that competes with that connection? It’s gone.

The same is true for my time online. Every scroll or refresh felt cheap, robbing me of moments I wanted to spend elsewhere. Stepping offline helped me prioritize the things—and the people—who really matter.

In the next frame: bedtime. The phone is off. Time returning to its natural speed.

Finding freedom offline

I think, often, about a specific kind of hell: the life of influencers, content creator, or anyone forced to always be online.

Not because those people or jobs are bad. Because the structure and incentives are brutal.

It’s the relentless pull of algorithms. The constant need to produce. The pressure to turn every thought, moment, or process into content.

Even if you’re not “trying to be famous,” the machinery makes it easy to confuse attention with meaning—and to confuse output with self-worth.

I’m not an influencer and never plan to be. But that gravitational force—to monetize everything, to narrate everything, to be “consistent”—is something we’ve all felt and heard.

Walking away was my way of making sure that force never outweighed what’s most meaningful to me.

Creativity, for me, cannot live tethered to an algorithm.

In the next frame: hands empty on a walk. Life happening without proof.

To write or not to write?

I haven’t loved the “post-for-growth” way the internet operates now. For me, writing has always been about sharing, exploring, and learning. It’s a creative outlet and intellectual exercise. No vanity metrics. No growth hacks. Just the words, and the meaning they bring.

Going offline robbed me of an audience, but it also forced me into something deeper. I began to grasp how, at its core, writing exists in the tension between what we choose to share and what we choose to keep.

What remains unseen, unshared—deeply ours—this is a form of wealth that can’t be measured.

The poet Mary Oliver once wrote,

The most regretful people on earth are those who felt the call to creative work...and gave to it neither power nor time.

Her reminder echoes in my mind every time I approach a blank page.

Some of what I write won’t hit the mark.

Some will veer beyond my supposed expertise.

Some pieces may fall into digital silence.

And all of that is ok.

I’m back, not to perform, but to practice.

I’ll keep writing, because the act itself matters.

Algorithms and metrics can lurk, but they won’t decide my path.

The real reward lies in what stays unseen, mine alone, in the quiet spaces where light can seep in.

In the final frame: a blank page, unhurried. The next sentence arriving.

Until Next Time!

That’s it for this week. As always, if you like the content, please do me a favor and like, share, subscribe — this newsletter runs on overpriced whiskey and reader engagement.

If you liked this post, I’d really appreciate it if you subscribe!

Subscribe now

Thanks for reading, and see you soon,

— Kevin K. (@kkirkpatrick)

Welcome to the 12 new subscribers—thanks for joining! Each issue of Path Nine is packed with meditations on work, productivity, tech, and entrepreneurship.

Today's newsletter was co-written with the fecund Tom White of White Noise. Together, we've delved deeply into countless discussions concerning AI, creativity, and the dramatic transformations of the internet. Over recent months, our exchanges have brewed into the thoughts shared in this newsletter.

Alright, let’s dive in.

Before we begin: If you’re reading this but haven’t subscribed to PATH NINE, hit the button below to join creative entrepreneurs that read PATH NINE to learn the strategies reshaping our work and lives.

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There was a time when writing online meant something. When words were wielded by the passionate, not those solely driven by profit or productivity.

When people made things because they had something to say, not something to sell.

Blogs were messy.

Newsletters were niche.

Tweets were raw. LinkedIn was…nonexistent.

The early internet—those halcyon days of Tumblr and Twitter, and MySpace—was imperfect, but at least it was honest.

No longer, I’m afraid.

We’ve barricaded the doors and boarded up the windows, but the call is coming from inside the house.

Today’s creative landscape looks more like a factory floor. Creators aren’t creators—they’re brands. Influencers aren’t interesting—they’re optimized. And everything, from your Instagram feed to your inbox, has been engineered for engagement, not meaning.

Welcome to the age of creator capture.

It nearly always starts with pure, unbridled passion. A writer or designer or thinker makes something weird and true and real. It resonates. It grows. And then the algorithm kicks in. Suddenly, the work becomes a performance. What gets clicks becomes what gets made. The edges get sanded down. Originality gives way to imitation. Junk food wins, so everyone starts cooking junk food.

And just when it seemed like it couldn’t get worse, AI showed up with a jug of high fructose corn syrup and started pouring it in the deep fryer. To wit:

From Inspiration to Imitation to Industrialization

AI doesn’t just speed things up. Worse, it flattens them.

It takes yesterday’s trends, remixes them with today’s keywords, and spits out tomorrow’s mediocrity. It’s not thinking. It’s rehashing. Recursive, regurgitative, relentless.

When AI trains on AI—which it increasingly does—we’re not just in a loop. We’re in a downward spiral.

It is a recursive nightmare. When the snake begins to eat its tail eventually, it devours itself.

Bad input begets bad output.

Sure, the internet isn’t empty; it’s just no longer for us.

Its content is made of, by, and for bots—an echo chamber of tinny, machine-churned noise.

The content gets smoother, faster, and emptier. And we start to lose our taste for the real; that is, “a desire for spiritual and cultural renewal, artistic excellence, and generative entrepreneurial endeavors, ordered toward the flourishing of the human person.”

The Easy Button That’s Making Us Dumb

Engaging no effort, AI tempts us with superficial gains, leaving our cognitive potential unchecked. And thus:

• Our attention spans wither

• Complexity becomes disfavor

• Creativity begins to capitulate

From Culture to Clickbait

Influencers have already transformed the internet into a dopamine market. AI is just scaling the slop.

Creators who once had vision now chase virality. Depth is rare. Speed wins. Authenticity gets optimized away. Anu Atluru said it brilliantly:

We create more than ever, but it weighs nothing.

AI now promises results without the reckoning, but frictionless creation leads to weightless rewards. No one dreams of merely pushing a button to generate their magnum opus. The output matters, but the intention, the struggle, the care is what makes it count — what gives it weight…

Weight is tangible in the physical world—a place we should care about and create more for than we have of late, even if it’s harder to scale. Working with your hands, with weight, shape, and dimension, holds an abundance of untapped virtue and value. Online, by nature, weight is harder to find, harder to hold on to, and only getting harder in a world where it feels like anyone can make anything.

But it is just as imperative.

People ask, "What are you working on?" They’re really asking: What’s your endgame? (It’s one of my favorite questions, too.)

My answer is simple, but not easy:

Make something heavy.

Our soliloquy has now become one long, infinite scroll.

Love letters are now texts.

Reactions, just taps.

Presence has been replaced by pings.

We’re not educating anymore. We’re engaging. Or worse, enraging.

Rage bait and SEO hacks.

Noise over signal.

Sugar over substance.

The platforms reward it.

The algorithms amplify it.

And we, the audience, play along like useful idiots: scrolling, sharing, forgetting ad nauseam.

Victor Hugo's words come to mind:

Everything being a constant carnival, there is no carnival left.

Because the truth is: we’re complicit.

We reward the junk by eating more of it because we have developed a taste for it/an addiction to it.

We are a culture/society in decline, or at least in the midst of creative stagnation—gorging on bread that does not satisfy and circuses that no longer entertain.

What Do We Do?

We can’t unplug. We can’t rewind. But we can resist.

• Cut ties with hollow content—your attention endorses quality.

• Champion authenticity—extol the raw and unreplicable.

• Make AI a tool, not supplanting creativity—a support to aspire, not lean entirely upon.

• Create like it matters. Not for clicks, but for craft. For clarity. For connection.

Because if we don't stay mindful, we risk losing the messy, human process of making something that matters. The shift from genuine creation to mere production is something we’re witnessing unfold right before us.

The Death of Creativity Isn’t a Murder—it’s Surrender

We didn’t lose creativity. We gave it away in exchange for scale, clout, and convenience.

And now we’re watching it suffocate under the weight of its own success.

AI didn’t start this. But it will finish it unless we step in.

In Ulysses, James Joyce wrote: “Think you’re escaping and run into yourself. Longest way round is the shortest way home.”

We must choose the “longest way round” because meaning is neither fast nor viral nor optimized.

It’s made. Slowly. Painfully. Honestly.

By humans.

Until Next Time!

That’s it for this week.

If you enjoyed this piece, I hope you’ll share it or subscribe. This newsletter—and my ego— runs on overpriced whiskey and reader engagement, so help me maximize both.

Share Path Nine

Thanks for reading, and see you soon,

— Kevin K. (@kkirkpatrick)

Welcome to the 48 new subscribers—thanks for joining! Each issue of Path Nine is packed with meditations on work, productivity, tech, and entrepreneurship.

It’s been a while since my last newsletter, but as you’ll see, it’s been a busy year of experimenting. Today I’ll share a bit about what’s been going on, a book (and mindset) that has me really excited, and an app to go along with it.

Alright, let’s dive in.

Before we begin: If you’re reading this but haven’t subscribed to PATH NINE, hit the button below to join creative entrepreneurs that read PATH NINE to learn the strategies reshaping our work and lives.

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I’ve been on a pretty wild ride for the last 12 months. Life has been every shade of vibrant and chaotic.

This past year, I’ve hit exhilarating peaks and endured deep troughs.

I said a final “goodbye” to the house I always dreamt of—a vision that unraveled.

Walked away from the place where I built that house and moved back to Seattle.

Stepped down from my role at Tiny, feeling worn down and itching for something different. I plunged into the world of fractional consulting, working with startups and founding teams.

But the true transformation came with the birth of my first child.

She’s redefined my world.

Sometimes, it’s her infectious laugh and warm smile that turns the grey days into gold. Other days, it’s her late-night cries—teaching me patience, the hard way, one sleepless hour at a time.

But with all change comes challenge.

For the ambitious, slowing down feels like turning off the freeway and directly into a school zone.

Anyone who’s scaled the career heights knows the struggle. There’s this internal pressure to outdo your past achievements. Even after making the conscious shift to step back from the grind, that anxious ambition sits, not-so-silently, waiting for me to get back in the game.

But I didn’t step back this past year just to catch my breath—I did it to reevaluate my relationship with work and ambition. To understand why parts of it felt unnatural, even unhealthy. The signs were there, I just needed to take a look.

The fleeting moments of success, gone as soon as they arrive.

The hollow feeling of a “win.”

The relentless moving of goalposts.

The sprint that morphs into an endless marathon.

It’s that toxic productivity mindset—where every achievement only fuels the next chase.

Too often I convinced myself:

Just spend enough time thinking about the next step or goal, and you’ll be golden. Everything will click into place.

But that finish line never materialized. Instead, I typically end up over-analyzing decisions and getting stuck in analysis paralysis.

Ironically, when running a company, I don’t agonize over decisions. I execute. I embrace an experimenter’s mindset. Yet, when the decisions are about me or my life, the experiments feel weighted.

Professionally, easing off the gas can feel like steering directly into the crash.

Aspire for that promotion? Keep grinding—your peers are closing in.

Want to build your dream home? Log more hours, stack the funds, and build.

Traditional definitions of success often feel limiting. When everyone climbs the same ladder, we become competitive, isolated clones. And when we’re clones, creativity suffers. Authenticity gets stifled.

But what if we flipped the script? What if we lightened the load? Could a change in mindset really change how we engage with ambition? What if we spent less time analyzing and crafting, and more time experimenting?

Life as an Experiment

Over the last year, I’ve been experimenting without even realizing it. Every big change, every difficult decision—it’s all been a series of small tests, some successful, some not. But nothing has made me more aware of the necessity of experimentation than becoming a parent.

Parenting is just a series of tiny (get it?) experiments.

Everything you do to get a baby to stop crying? An experiment.

Everything you think you’re doing right or wrong? Also an experiment.

One day, rocking her to sleep works. The next day, it doesn’t. One moment, she loves a certain food. The next, she spits it out in protest.

It forces you to abandon rigid expectations and embrace flexibility. You try, you learn, you adjust. There’s no way to “win” at parenting—only to iterate. It’s an endless series of tiny experiments.

The more I recognized this, the easier it was to see that life itself is just a series of ongoing experiments. The problem is, we’re stuck trying to plan our way to a perfect life. We treat choices as permanent and failures as fatal when, in reality, they’re just feedback loops.

This realization made me more receptive to Anne-Laure Le Cunff's new book, Tiny Experiments: How to Live Freely in a Goal-Obsessed World.

Embracing an Experimental Mindset

Anne-Laure, a neuroscientist and entrepreneur, challenges the traditional linear life approach, marked by rigid goals and predefined milestones. Instead, she advocates for viewing life as small, meaningful experiments. She encourages a flexible and curious growth mindset, trying different methods, observing results, and adapting. This approach turns uncertainty into a learning opportunity, rather than a source of anxiety.

In 2023, I had a chance to sit down with Anne-Laure to discuss what would eventually become Tiny Experiments. During our call I shared my journey with toxic productivity and my path to a more fulfilling creative, entrepreneurial life. Over the last week or so, I’ve been pouring over the ideas and insights shared in the book. It’s so clear that her emphasis on curiosity as a compass is a powerful way to find authentic paths aligned with our values. I loved this little reflection about how a scientist would think about the results of an experiment:

When a scientist conducts an experiment and they don't get the results they expected, they don't go, 'Oh, shame! I'm such a failure!' They go, 'Huh...interesting! What is going on here?'

The experimenter leans into four key steps to unlock more curiosity in work and life:

• Observe: Assess the current state

• Hypothesis: Formulate a research question (ex: “I believe that doing X will yield Y”)

• Test the hypothesis — repeat the action long enough to get sufficient data

• Analyze the results

Only once you have completed the full test should you analyze the results and draw your conclusions.

This mindset encourages us to see setbacks as learning opportunities.

Inspired by these insights, I found value in letting go of rigid outcomes and following my curiosity, which eased the pressure of constant achievement and opened new avenues for creativity and growth in the years ahead.

Tiny eXperiments: A Tool for Experimentation

Tiny Experiments encouraged me to recalibrate—to focus on what’s right, right now. It made me realize how much we overcomplicate things. How often we stand in our own way.

We just need to execute, without overthinking.

As the saying goes online, “You can just do things.”

As cliche as it sounds, it holds water.

Want to build an app? Nothing is stopping you. No need for permission. No need for lofty long-term goals. Just a willingness to experiment.

So, in true Tiny Experiments fashion, I built a Tiny eXperiments app to help document experiments and support those embracing an experimenter’s ethos.

With the app you can:

• Create and track experiments

• Share your experiments (or keep them private)

• Record your progress on each experiment

• Join other experimenters on their journey

You can share experiments in public to increase your accountability:

Followers can cheer you on along the way or even join you in the experiment.

The idea for this app actually came to me years ago, but the book gave me the push to make it real. I’ve always believed in testing new ideas and finding ways to improve. When we treat life as an experiment, we add a childlike curiosity that makes the world more vivid.

We start asking better questions:

• What do I hope to learn from this experiment?

• How will completing this help me grow?

• What can I take away from the results?

Anne-Laure’s book served as a catalyst for my own creativity. It reminded me to build Tiny eXperiments and reawakened the builder in me.

It helped me just let go of outcomes and follow my curiosity.

If there’s one thing to take away from Anne-Laure’s Tiny Experiments, it’s that when we free ourselves from the shackles of traditional scripts passed down to us, we open ourselves up to a life filled with curiosity, authenticity, and connection.

Here's to tiny experiments, and all of the tiny experimenters.

And, in case you missed it…

Here’s a few related posts I’ve written that people enjoyed:

Until Next Time!

That’s it for this week. As always, if you like the content, please do me a favor and like, share, subscribe — this newsletter runs on overpriced whiskey and reader engagement.

If you liked this post, I’d really appreciate it if you share it!

Share Path Nine

And, in the longstanding tradition of offering to help, here are a few ways I can be helpful:

1. Book a 1:1 Consulting Call with me. During the call, we’ll do a deep dive into whatever issues you’re facing—from growth to validating business ideas to automating and/or delegating work.

2. If your business is looking for help with growth and you need a seasoned builder to reach the next level, reply and let me know.

Thanks for reading, and see you soon,

— Kevin K. (@kkirkpatrick)

It’s Kevin K., and this is Path Nine—a newsletter featuring modern meditations and takes on work, productivity, and entrepreneurship.

Lately, I've been brewing up a storm of fresh ideas. But here's the kicker: while I thrive in the art of tinkering, I've noticed that many don’t know what it means. Curious to learn how this game-changer can supercharge your work and creativity? Explore the idea with me, and let me know your thoughts on tinkering.

Alright, let’s dive in.

Read time: 6 mins

Before we begin: If you’re reading this but haven’t subscribed to PATH NINE, hit the button below to join creative entrepreneurs that read PATH NINE to learn the strategies reshaping our work and lives.

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After lunch on a Sunday afternoon as a kid, I’d often hear my dad proclaim that he was going to ‘tinker’ in the shop. Despite the regularity of these Sunday tinkering ventures, I had no idea what he was it actually entailed. I was more focused on getting out of chores or yard work.

Now that I’m much old(er), I better understand what he meant by tinkering.

Tinkering is work, but it’s also not work.

It’s the kind of work that doesn’t require deep thinking or focus.

For me, it’s the stuff I can do slouched down on the couch with my laptop and The Office playing for the 348th time in the background.

For him, it was rearranging tools and cleaning up his workspace.

In many ways, it isn’t really work at all.

It’s neither hard nor laborious.

It’s both tedious and stimulating.

It’s unfocused and yet engaging.

It’s just…tinkering.

Tinkering—often mistaken for aimless activity—is a crucial foundation for creativity and innovation, providing the mental space necessary for ideas to gestate and evolve.

The act of tinkering is akin to wandering through a garden instead of marching down a path. It's not about deep focus or intentional outcomes. It's all tidying up vs. deep cleaning.

Tinkering is like a music playlist, blending work and life seamlessly. It's not always about striving for capital-P productivity but about activating new ideas through relaxed exploration. By giving ourselves the freedom to tinker, we create space for true creativity to flourish.

In exploring the essence of tinkering, I see found parallels in writing this piece. Like a tinkerer joyfully engages in tasks, such as rearranging pixels or sending emails, I've been tinkering with its ideas, words, and paragraphs, allowing my thoughts to evolve and take shape over time. Instead of leaving you with the final draft, I’ve opted to include them because, as any writer knows: showing always beats telling.

Though I’m sure it makes this article harder to read—maybe that’s the point. By engaging with the variations iterations of an idea and ignoring the modern tendency to only show our best work, we lose the opportunity to truly be creative. The process of experimentation, refinement, and playful productivity is what tinkering is all about.

"Creativity is allowing yourself to make mistakes. Art is knowing which ones to keep." - Scott Adams

It’s a bit unhinged, but in a world where we’re always showing the Instagram version of ourselves, we need more space to let the bad ideas fly, show behind-the-scenes shots, and iterate. Good ideas come through iteration and self-exploration, not striving for perfection.

The funny thing is that a lot of our modern work culture is digital tinkering.

So what is tinkering?

Tinkering with ideas is a playful exploration or a taking of inventory. It's about noodling and letting bad ideas fly pass by so you can discover the good ones. This light, unfocused work prepares for deeper, more meaningful creative work. Letting 1,000 flowers bloom requires some weeds to take root, the key is not to pluck a flower-looking weed or weed-looking flower too early. Creativity requires time to grow and develop.

Tinker-Core: Balancing Shallow and Deep Work

In productivity and creativity, tinkering is the connective tissue between the realm of shallow work and the domain of deep work. Tasks like organizing emails or reading documents can be the first step towards deeper work, a warming of up the creative engines so to speak. By allowing ourselves to tinker with ideas and concepts on a surface level, we create a foundation for deeper exploration. Tinkering, with its playful and exploratory nature, acts as a precursor to the focused attention and immersion required for deep work, enabling us to transition from light experimentation to substantial creativity.

Tinkering takes various forms but has consistent characteristics:

1. Multi-taskable - the work can be done with sports or a podcast on in the background.

2. Highly-variable - the task might not be clear until you’re in it the journey is the destination.

3. Optional - the work isn't critical, but it's necessary for productivity.

Tinkering is the shallow work we do to keep the hedonic productivity wheel turning. We know we’re supposed to work, so we do. In modern, Americanized work cultures, work is the only true form of fulfillment, value, and meaning—happiness is exists only for the productive. If productivity is next to godliness, the lack of productivity is the deepest a form of depravity.

Done right, tinkering is productive and therapeutic. Done wrong, tinkering is it’s nothing more than feckless wandering.

Tinkering, like a gardener pruning with care, can cultivate creativity and productivity. Yet, aimless tinkering is akin to a lost sailor adrift at sea, lacking direction and purpose.

Tinkering is the gentle stream that guides creativity toward its destination, channeling ideas into productive waters. But without a map or compass, tinkering may become a wandering cloud, drifting aimlessly in the sky.

In the words of J.R.R. Tolkien, 'Not all who wander are lost.' Just as wandering holds purpose, so does tinkering. Embracing a playful approach to productivity can lead to creative breakthroughs. Let's label our tinkering correctly and explore the value it brings to our work and lives.

Our work shapes how we think about it; it is a self-fulfilling prophecy. We often categorize tasks as 'work,' attaching a sense of importance or obligation to them. But what if we reframe these activities as tinkering as a way to decrease friction and find ways to reconnect with a more playful form of work? Emailing, reading documents, or sending Slack messages may not require deep thinking or effort, but labeling them as 'work' can make us feel productive. Are we becoming modern-day pencil pushers, engaging in activities that may not involve intense labor but still provide a sense of productivity?

The Value of Tinkering Across Contexts

For me and my dad, tinkering was a mix of playful productivity and therapy. It was a way to feel productive without the stress of actual work (aka the big, haunting tasks you’re avoiding). Tinkering offers a stress-free way to feel accomplished, and potentially enjoy yourself. And for people like me who struggle with perfectionism, anxiety, and intense ambition, finding ways to enjoy work while also feeling a sense of accomplishment is critical. When we push too hard, we end up going backward. It’s like having a fixed gear bike; you can pedal hard, but it’s better to go at the bike's pace, lest the chain comes off.

In the realm of everyday creativity tinkering lies a path to flourishing, as illuminated by a study titled "Everyday Creative Activity as a Path to Flourishing" by Tamlin S. Conner, Colin G. DeYoung, and Paul J. Silvia in The Journal of Positive Psychology. Their insightful research explored the daily lives of 658 young adults, revealing a fascinating cycle: engaging in creative endeavors led to elevated positive emotions and a heightened sense of flourishing the following day. This suggests that nurturing our creativity not only enhances our well-being but also fuels a continuous cycle of creative inspiration and fulfillment.

Whether you’re an entrepreneur or a corporate employee, modern work requires balance, but it can be hard to find. As I’ve written before, there are many ways of working. I'm most fulfilled when I alternate between work and life, combining elements like a guitarist or bassist.

While this approach works for me, others find it jarring or impractical. But it works for me because I spend time tinkering, sitting, thinking, keeping my mind and hands busy, not always worrying about a strong drive for capital P productivity, but activating nascent thoughts and ideas by taking my mind off them.

Organizing my to-do list is never my top priority. Just like organizing and labeling the tools in the shop were not my father’s priority. But this is the preparation for creative thinking and working—the clearing of mental clutter and RAM for productivity’s sake. Completing it in the quiet periods allows you to capitalize on your full creative potential when the opportunity arises.

If my work is a mess and I try to sit down to write, I feel the pull of the unmanaged work, nagging me to attend to it. But when I tinker unproductively, I create more space to think and create, even if not immediately. Gustave Flaubert reminds us that we should,

"Be regular and orderly in your life, so that you may be violent and original in your work.”

Reframing helps me avoid deciding when to work and reduces the anxiety of doing the work, allowing me to put real effort toward it when the time comes.

Maybe this won’t work for you, but it’s been helpful for me.

In a world where productivity is often measured by output and efficiency, the concept of jobs for individuals who simply enjoy tinkering 24/7 seems refreshing, albeit somewhat unrealistic in the near future. Imagine a workforce where individuals are encouraged to explore and experiment without the pressure of traditional work demands. Allowing time for more people to tinker could not only lead to innovative products and ideas, but also foster a unique sense of fulfillment for more of our workforce.

As I think about the impact what the future looks like for tinkerers like me, I imagine AI and Universal Basic Income will play an important role. But that’s an idea for another day, and another time.

Embracing our inner tinkerer allows us to revisit the joy found in unrestricted exploration, blending work and life into a harmonious rhythm that nurtures rather than drains. In this space, we don’t just work—we play, explore, and ultimately, flourish.

Until Next Time!

That’s it for this week. As always, if you like the content, please do me a favor and like, share, subscribe — this newsletter runs on overpriced whiskey and reader engagement.

If you liked this post, I’d really appreciate it if you share it!

Share Path Nine

And, in the longstanding tradition of offering to help, here are a few ways I can be helpful:

1. Book a 1:1 Consulting Call with me. During the call, we’ll do a deep dive into whatever issues you’re facing—from growth to validating business ideas to automating and/or delegating work.

2. If your business is looking for help with growth and you need a seasoned business builder to reach the next level, consider using Uprise.

Thanks for reading, and see you soon,

— Kevin K. (@kkirkpatrick)

It’s Kevin K., and this is Path Nine—a newsletter featuring modern meditations and takes on work, productivity, and entrepreneurship.

This week, I’m reflecting on a hotly-debated topic: the importance of the office (and lack thereof). I won’t spoil it, but I’m rethinking a few key aspects of remote work, and maybe you should too.

Alright, let’s dive in.

Read time: 6 mins

Before we begin: If you’re reading this but haven’t subscribed to PATH NINE, hit the button below to join creative entrepreneurs that read PATH NINE to learn the strategies reshaping our work and lives.

Subscribe now

Acquisitions are weird.

One day, you’re doing your job and things are going well.

The next, you’re working for someone else and hearing that nothing will change.

It's akin to waking up from unconsciousness: the room spins, disorientation sets in, and you’re unsure where you are or how you got there.

In the blink of an eye, the familiar rhythms of my job were upended, ushering me into a new reality where, unbeknownst to me at the time, the seeds of my journey into the future of work were planted. That wild journey led me to a lot of interesting things; last minute international travel, 11pm conference calls, and my introduction to the always-on work culture I’d come to accept as normal.

But most interestingly, it led me to a core feature of what I’d come to see as a key component of the future of work: remote work.

I started working remotely in early 2013. It wasn’t really on purpose, nor was it in vogue. Prior to 2013, remote work wasn’t something people thought a lot about. Outside of support and call centers, or the occasional ‘telecommuter,’ it just wasn’t part of the work vernacular.

And it certainly didn’t feel natural in 2013.

If you look at this chart from We Work Remotely, you can see that the number of jobs listing for remote workers has grown by nearly 1200% in that time.

But honestly, it really didn’t feel like it.

There was no grand “welcome to the remote work party” banner. No strong cultural pulse that brought remote work to the forefront. If anything, remote work was considered a backup option, for specific circumstances like disabilities, outsourced roles, or consultants. It wasn’t mainstream or understood.

I stumbled into a world without borders by accident. At the time, I was working for Deloitte consulting. My job, at the ripe age of 25, was to lead the global expansion efforts for the new consulting line that had formed after the acquisition of my previous company, Übermind.

During this acquisition, I was lucky enough to be given the opportunity to avoid the traditional consultant paths offered by Deloitte, which may have been interesting, but likely would’ve sent me down a completely different career trajectory—a career with more suits, planes, and hotels next to the airport. Instead, I was lucky to be offered a global expansion role, which kept me out of client-specific consulting, and made me an internal operator, tasked with launching and growing the newly-formed Deloitte Digital Studio Model. My role in global expansion had some interesting requirements, which ultimately led me to my first remote work experience. These included:

• Time zone management. As you might imagine with the word ‘global’ in the title, my job entailed working with teams and people in different countries. This meant having to manage time zones outside of my usual +/- 3 hour calculations.

• Video and conference calls. For years, most of my meetings were in person. Whether it was in the office with my studio coworkers or meeting a client to present, my time was spent literally face-to-face. And then one day, that all changed. I went from mostly in-person, to mostly virtual. I didn’t feel it immediately, but over time, it felt like my personality shifted from being a real person to a virtual person.

• Isolation. In the shift to virtual work, it meant a disconnect from my local colleagues. Even if we worked in the same office, we didn’t have the same schedule, the same work, or the same experiences anymore. I found it more and more difficult to talk with them about work, since our worlds were so far apart. Eventually, I stopped coming into the office except to socialize or for the occasional office-sponsored happy hour.

After a decade of working remotely, I’ve realized that there are things I deeply miss about working in an office. I don’t think I’m completely alone here. In fact, just the other day, a past colleague of mine told me they’ve accepted a hybrid role. They’ve been working and advocating for remote work for years, and yet, they decided to take a little break from the fully-remote world.

As someone who has spent a lot of time thinking not just about how we work, but how we are productive, how we cultivate a relationship with work, and how we set boundaries, I think there are gaps that have yet to be filled in remote work. A growing body of research underscores the profound impact of social interactions and environmental context on our work and well-being.

I want to be abundantly clear: I do not want to return to the office, not now, not ever. Further, I don’t believe in-person work is a better way to work, at least not in most cases. But more importantly, I think the remote/in-office debate leaves little room for nuance, and therefore misses the mark altogether.

I’ve realized that there are some important things I am missing when working remotely, and I plan to fix them in 2024. And no, it’s not the ‘random coffee chats’ or ‘in-person’ meetings.

• Scheduled social interactions - again, not the random chat kind. What I miss is the scheduled social interactions of office timelines. I miss the ‘let’s grab lunch/coffee’ times of the day. When we have scheduled social time, we naturally increase our productivity in order to ensure it doesn’t interfere with our social mores the scheduled social time. When our schedule becomes flexible, we lack the urgency of fixed deadlines, even if they’re for social interaction.

• Time offline - I miss the forgiveness and empathy of needing time outside of work. The ability to say, ‘hey, I’m on my way to the office, I’ll look at that when I get in.’ I miss the option to say, ‘I have to leave early to run an errand, so I won’t be able to make a 4pm meeting today.’ I find that, as a remote worker, it is incredibly difficult to share the reasons that we can’t—or won’t do things. Worse still, remote workers are often given very few options to not work. The assumption is that by giving up the commute, you have infinite time to work, and therefore should always be online.

• Thinking time - the commute is shit, but it can have benefits. First and foremost for me: time to think. One of the first things that I realized I was missing about the office was time to be alone, gather my thoughts, and think about things that were on my mind. By removing this time, I’ve found that I default to action. Instead of sitting and thinking about an idea on my commute, I choose to work. Instead of taking time to breathe, I work. Everything gets flattened to work.

• A sense of place - how we feel about what we do is incredibly important, as it shapes our self-worth and helps us orient ourselves to the world. Where we do what we do can be just as important. One of the biggest challenges of working remotely is being able to place ourselves in work mode. When you can work anywhere, we see work everywhere. But the office gives us a place to place work. It lives there. It stays there when we leave. It has a home, and it’s not our actual home.

All of these are specific to me. It doesn’t mean that they are insurmountable, or something that changes the calculation of my interest in working remotely. In fact, they further cement my position on the subject, as they reinforce the idea that remote work isn’t just about where you do your best work, but how you do your best work. If we want better ways to work, we have to think outside the box and explore all ways of working and living in harmony. I want reinforce this in my own work and in the narrative at large.

Rethinking My Office

In 2024, I’m taking a different approach to working remotely. I’m keeping the core components; working asynchronously, documentation-first, (mostly) virtual meetings, etc. But I’m also making some pivotal adjustments that I think will have a major benefit for me, my work, and my family.

• Be a 9-5er - I’m a huge fan of work-life harmony, no matter how you come by it. Historically, I’ve leaned into my natural rhythms of being a cycler, but over time, I find it wears on me. Instead of working when inspiration strikes or I feel ready to tackle something, I just end up grinding through work, all day, with micro-breaks. For 2024, I’m taking a stronger stance on remote work boundaries, and trying a 9-5 schedule—or as close to that as reasonable.

• Co-work - with our recent move back to Seattle, I’ve decided to pick up an office at a co-working space. Luckily, it’s right next to our home, so the commute is the time it takes to ride the elevator down, walk 50 yards through our garage, and ride a second elevator back up two floors. This setup allows my wife to have her own space at home, and helps me enforce my goal of being a 9-5er.

• Go analog - one of my challenges with remote work is the fact that everything goes through my screens—from my phone to my laptop to my desktop, it’s all screens. Passing thoughts, ideas, and chats through this glass box filled with pixels isn’t the way I want to exist, and it’s not how I’ll do my best work. To combat this, I’m integrating analog tools into my workflow, including a whiteboard, notebook(s), and a separate, analog desk.

• Walk it off - I need to walk more. When I was in the office, I’d walk a lot more. I’d go to lunch, get coffee, or just do a walking meeting with people from the office. While most of the time those walks happened with close colleagues and friends, that wasn’t always the case. Sometimes I’d join a random group of designers or engineers, just to get out. It’s hard to do that on your own, but I want walking to be a part of my life. So every day, I take my dog across the street for a walk. Some days, I walk my wife to work. Others, I walk to meet someone for coffee, lunch, or drinks. My goal is to walk as much as possible.

Zooming Out

Depending on your stance, these changes may sound mundane or revolutionary. Remote purists may even take issue with some of these. But that misses the point. The point of remote work has never actually been about working at home, on your couch, or on a beach in Fiji. Remote work is about flexibility. It’s about a way of working that not only helps us do our best work, but bring work and life into harmony. And the harmony of work and life can only be heard when we listen and adjust our tone.

It’s easy to look at what we don’t have and assume it’s better.

We have the Honda, but we want the Tesla.

We have the big house, but we want the boat.

The grass, perpetually seems greener, no matter the context.

In reality, the grass isn’t always greener. Sometimes, the grass is greener in a few spots, and dead everywhere else. We might only see the small patch, and assume the rest looks the same. The map is, in fact, not the territory.

Our workspace choice shouldn’t be binary.

We shouldn’t have to choose between a sub-par home office (aka kitchen table) or a high-rise office.

We shouldn’t have to choose between working a job we like, and spending necessary time with our family.

We shouldn’t have to be forced into these polarities—there exists space for convergence.

When it comes to remote work, it’s easy to feel like we need to pick sides; you’re either with us, or you’re against us. Like anything else in life, we should admit and embrace the need for better options, both in work and at home.

The Delphic oracle might have been speaking to workers when she famously said, "know thyself.” I, for one, plan to do so.

Until Next Time!

That’s it for this week. As always, if you like the content, please do me a favor and like, share, subscribe — this newsletter runs on overpriced whiskey and reader engagement.

If you liked this post, I’d really appreciate it if you share it!

Share Path Nine

And, in the longstanding tradition of offering to help, here are a few ways I can be helpful:

1. Book a 1:1 Consulting Call with me. During the call, we’ll do a deep dive into whatever issues you’re facing—from growth to validating business ideas to automating and/or delegating work.

2. If your business is looking for help with growth and you need a seasoned business builder to reach the next level, consider using Uprise.

Thanks for reading, and see you soon,

— Kevin K. (@kkirkpatrick)

Welcome to this week’s Path Nine Reflection and Recommendations. Each issue aims to enhance your thinking, lifestyle, and work by sharing distilled reflections and recommendations from the past two weeks.

Don’t feel like scrolling? Here’s the tldr version:

• Reflection: Look Back.

• Rec: Product, Tool, or Framework: The Five Whys.

• Rec: Read: The Gap and The Gain: The High Achievers' Guide to Happiness, Confidence, and Success.

• Rec: Watch: Neil Gaiman - Inspirational Commencement Speech at the University of the Arts 2012.

• Rec: Listen: The Happiness Lab with Dr. Laurie Santos Happiness Lessons of The Ancients: Sikhism and Daily Habits.

Have a calm, productive, and creative week!

Before we begin: If you’re reading this but haven’t subscribed to PATH NINE, hit the button below to join creative entrepreneurs that read PATH NINE to learn the strategies reshaping our work and lives.

Subscribe now

Reflections

◎ Look Back

A few weeks ago, I sat down to do some digital procrastination (i.e. moving things around on my personal website to convince myself I’m being productive). After learning about Substack’s Nazi problem, I started thinking it might be time to create a separate digital archive, in case the platform goes the way of the dodo. The problem came to light in November of 2023, following this article in The Atlantic, which surfaced a number of white-supremacist, neo-Confederate, and explicitly Nazi newsletters on Substack, some of which featured overt Nazi symbols. The founder’s laissez-faire approach to content moderation and its indirect profit from such content through subscription revenue shares are concerning, to say the least.

As much as I’ve loved Substack, I have a few lingering concerns about where they’re headed. So, instead of waiting for the Nazis to take over or for the potential downfall of Substack, I decided to move some posts to my personal blog. That way, if the Nazi’s take over Substack, I have a good back up to continue building from, or at least not supporting something I don’t feel proud to be a part of. It’s ironic that Substack’s Nazi problem—and the process of migrating articles—made me consider pride. Not just pride in where my work lives, but in the work itself.

When I started my digital relocation process, I figured it would quick, because I only had a handful of articles to move. Before I knew it, two hours had passed.

And that’s when it hit me; I had actually written a lot over the years.

Not only had I written a lot, I’d actually written some things I liked.

Just like that, I felt it. That feeling I don’t often allow myself feel. That feeling that tells you you’re doing okay. That feeling that reminds you, as much as there is left in the journey ahead, you’ve already come so far. That feeling? Pride.

For years, I told myself I wanted to write more. But year after year, I felt like I wasn’t writing enough to even pretend to be a writer. And then, I saw the evidence—I was writing.

In this moment, I was able to peek over my shoulder and see the journey I’d traveled, one sentence at a time. Each word, another step. Each sentence, another hill. Each article, another mountain. Suddenly, I wasn’t left wondering if it was possible—the proof was right in front of me.

As any ambitious perfectionist knows, this feeling doesn’t come easy.

My body and mind fight to reject the foreign object that is positive feedback. For with positive feedback, comes complacency. With complacency, comes laziness. And laziness is the surest path away from success.

I’m hard on myself because I want more—which makes it difficult to really feel proud of anything.

If I write something, I tear it apart.

If I design something, I have to critique it.

If I build something, I tell you why it could be better.

All that energy helps me push to be better, but it also keeps me from ever feeling good.

I am never proud of myself. Never.

And yet, here I was, somehow feeling proud when hitting copy and paste on my keyboard.

Was I proud of everything I had written?

Of course not; no writer, or perfectionist, is.

But that’s not what matters.

What matters is that we strive for a goal, that we face our fears and push through the pain, regardless of the obstacles or potential outcome.

And, as I cut and pasted each article, I found little bits that reminded me why I love it so much—why I push through the pain. As I wrote in Things You’ll Never Regret

while many details in our lives are unknowable and unchangeable, we're sometimes presented with opportunities to turn mundanity into miracles.

The mundane act of moving these words from one digital space to another gave me a little reward. It forced me to pause, to feel, to reflect, to enjoy—and to rejoice.

It’s important to feel the rewards of our work.

It doesn’t matter if other people like it, sometimes all you have to do is look back.

Looking back lets you see how far you’ve come.

The road ahead is long, winding, and scary.

Sometimes looking back at the road behind reminds us how many mountains we’ve climbed, challenges we’ve faced, and obstacles we’ve overcome.

Don’t forget to turn around, look back, and be proud of how far you’ve come.

Recommendations

✪ Rec: Product, Tool, or Framework

The Five Whys

Anyone in a typical MBA program will likely be familiar with The Five Whys. But for those of you who aren’t already familiar, The Five Whys is a simple problem-solving framework pioneered by Toyota’s manufacturing teams to streamline their production and assist in root-cause analysis. While it’s definitely a great tool for business, I find it just as interesting and effective for personal reflection.

The concept is simple: by asking "why" five times, you can uncover the root cause of a problem or a feeling, including why you might feel dissatisfied with your work or why certain projects felt more fulfilling. It's a method that encourages deep thinking and can lead to significant insights about your creative process and achievements. If nothing else, it forces you to allocate time to think in a methodical manner—something that’s always valuable.

✪ Rec: Reading

The Gap and The Gain: The High Achievers' Guide to Happiness, Confidence, and Success

I read this book one weekend when my wife was traveling for work. I typically have a bit of extra free time, and since she and I do a book club, I couldn’t read the book we were reading together. When I started, I was afraid this would be all fluff, and no substance. To my surprise, this quick read really hit home. As the title eludes to, the book walks you through the difference between the gap and the gain mindset. Without spoiling it too much, the book reminds us to focus on 'the Gain'—our achievements and how far we've come—rather than 'the Gap'—the distance between where we are and where we wish to be. For any perfectionist, this can be powerful tool to unlock pride, fulfillment, and satisfaction in their growth.

✪ Rec: Watching

Neil Gaiman - Inspirational Commencement Speech at the University of the Arts 2012

“The problems of failure are hard. The problems of success can be harder, because nobody warns you about them.” - Neil Gaiman

I rarely watch commencement speeches. For some reason, they feel fake, like a perfectly staged scene in an award-winning drama. But, every now and then one slips through, and proves me wrong. Neil Gaiman's commencement speech is a masterclass in the resilience required for creative work, particularly writing. He shares insights on the journey of a writer, emphasizing the importance of perseverance, making mistakes, and finding pride in your work. It’s a compelling watch for anyone reflecting on their creative journey, offering motivation to embrace the process and the progress made along the way.

✪ Rec: Listening

The Happiness Lab with Dr. Laurie Santos Happiness Lessons of The Ancients: Sikhism and Daily Habits

Look, I’m not going to start talking about happiness and all the warm fuzzies that you’d expect from a recommendation like this. Why? Well, first, it’s not the point. Second, I’m a millennial, so I’ll just keep buying avovado toast instead.

But, what I will talk about is the importance of daily habits that ultimately lead to happiness and fulfillment. Just as I found unexpected joy and pride in the simple act of organizing my digital space, this podcast reminds us that integrating mindful habits into our daily routines can transform mundane activities into sources of profound joy and satisfaction. The episode serves as a gentle reminder that happiness and a sense of accomplishment can emerge from the rhythm of our daily lives, encouraging us to appreciate the progress and meaning in every moment of our creative journey.

Pathfinders’ Spotlight

Fellow Pathfinder hype links and shoutouts.

you are here - Nanya Sudhir ()- If you're drawn to reflections on creativity and the nuances of our daily lives, you'll find a kindred spirit in Nanya's writing. Her article, "Are You Your Routine?", dives into how our daily rituals shape us, blending introspection with enlightening perspectives. I highly recommend it for anyone interested in the interplay between habit and identity. It's a compelling read that resonates well with the themes we cherish here. Check it out ↗︎

Interested in getting a shoutout? Just shoot me a note.

And, just in case you missed it…

Here are some things that I’ve written and shared that people enjoyed.

Until Next Time!

That’s it for this week. As always, if you like the content, please do me a favor and like, share, subscribe — this newsletter runs on overpriced whiskey and reader engagement.

If you liked this post, I’d really appreciate it if you share it!

Share Path Nine

And, in the longstanding tradition of offering to help, here are a few ways I can be helpful:

1. Book a 1:1 Consulting Call with me. During the call, we’ll do a deep dive into whatever issues you’re facing—from growth to validating business ideas to automating and/or delegating work.

2. If your business is looking for help with growth and you need a seasoned business builder to reach the next level, consider using Uprise.

Thanks for reading, and see you soon,

— Kevin K. (@kkirkpatrick)

Welcome to this week’s Path Nine Reflection and Recommendations. Each issue aims to enhance your thinking, lifestyle, and work by sharing distilled reflections and recommendations from the past two weeks.

Don’t feel like scrolling? Here’s the tldr version:

• Reflection: The Curse of Optimization.

• Rec: Product, Tool, or Framework: Rize App.

• Rec: Read: Essentialism: The Disciplined Pursuit of Less by Greg McKeown.

• Rec: Watch: Jeff Bezos - Regret Minimization Framework.

• Rec: Listen: Ditch Your To-Do List and Do This Instead | Sam Corcos | The Tim Ferriss Show.

Have a calm, productive, and creative week!

Before we begin: If you’re reading this but haven’t joined the PATH NINE community, hit the button below to join creative entrepreneurs that read PATH NINE to learn the strategies reshaping our work and lives.

Subscribe now

Reflections

◎ The Curse of Optimization

Today, I write to you with a quiet, peaceful view of the rain-kissed Seattle waterfront. Stereotypical coffee in-hand, books at my side, surrounded by the grey fog. Once again, I find myself nestled amid the familiar rhythms of this city. Having recently returned to the city following a three year stint building a house in central Washington, I’m quickly reminded of the allure of the never-ending optimizations I pursue in work and life. It’s the double-edged sword that tempts me with the promise of increased efficiency, productivity, and progress. Yet, lurking beneath its glossy exterior lies a subtle danger — the curse of over-optimization.

As my wife and I settle back into our 900 square-foot home in downtown Seattle, I’m quickly reminded of the seductive nature of the constant fine-tuning I do in work and in life. At work, it manifests in delegation, optimization, and iteration. At home, though it’s the same process, it seems less insidious. Rearranging books and furniture feels not only productive, but deeply satisfying. And yet, the driving factor of work and personal optimization stems from the same central feeling: fear.

It's easy to get lost in the whirlwind of perfecting our routines and environments, believing that we are moving closer to our goals when, in reality, we may be skirting the hard work that leads to genuine growth and improvement. Eventually, we encounter the law of diminishing marginal returns, exceeding the point of optimal output and risking wasted time and energy with reduced efficiency. Our pull toward the insidious curse of optimization, while offering a facade of productivity, can stifle the very creativity and spontaneity that fuel our most inspired endeavors.

So, as I reacquaint myself with this quite familiar landscape, I remind myself of the importance of balancing creative and productive fulfillment, and embracing the messy and imperfect journey without falling prey to the curse of optimization. For it is in the spaces between the perfectly optimized paths that true creative freedom thrives.

Recommendations

✪ Rec: Product, Tool, or Framework

Rize App

An AI productivity tool that tracks how you spend your time, allowing you to focus on deep work and analyze how you spend your time.

I’ve been intermittently using Rize for a few years. In the beginning, I thought of it as a way to track my time and used it to look for areas where I could continuously optimize and improve my overall productivity. But, I found that left my work feeling hollow, and focused my energy on optimization instead of positive aspects like curiosity, energy, and flow.

Now, I use Rize to help me track and engage with my energy. I look at what tools and tasks help me get into the flow, so I can lean into those more. Instead of trying to squeeze every ounce of work out of myself, I’m trying to fill myself up with what energizes me the most.

✪ Rec: Reading

Essentialism: The Disciplined Pursuit of Less by Greg McKeown

As mentioned above, after three years of living in central Washington, my wife and I just moved back to Seattle. As with any move, it’s a chance to reset and ‘optimize’ our lives for the things we value most. One of the things we’ve been reminded of in the move is that we need—and want—far less than we think.

Essentialism explores the concept of not just having, but wanting less—focusing on what truly matters and eliminating the non-essential. It offers insights into avoiding the trap of over-optimization by prioritizing the vital few over the trivial many. Whether it’s at home, in our work, or through our relationships, sometimes less truly is more. Or, as the author Greg McKeown notes,

You cannot overestimate the unimportance of practically everything.

✪ Rec: Watching

Jeff Bezos - Regret Minimization Framework

It’s a cliche to say that ‘life is short’, but cliches always carry some amount of truth. There’s no shortage of people or things to fill our time. We’re constantly bombarded with opportunities and responsibilities that, one by one, fill up the individual units that comprise our life. No matter how you slice it, time marches on. With each passing moment, we’re faced with the option to fast or feed our creativity. One of the easiest ways to do this is to minimize regret.

The framework is simple, yet profound—when faced with a decision, imagine which option would reduce regret for future you. For Bezos, this led him to leave his job and start Amazon, fearing he would regret not participating in the internet boom more than failing at a startup. Essentially, it's about choosing the path that you'll regret the least when you're older, to ensure you embrace opportunities and live without major regrets.

✪ Rec: Listening

Ditch Your To-Do List and Do This Instead | Sam Corcos | The Tim Ferriss Show

Everyone I know is looking for the next great to-do app or system. It’s why people like James Clear are so popular: people are desperate for the solution to the overwhelming nature of work.

But better to-do lists usually just feel like re-arranging deck chairs on the Titanic. Instead of relying on an infinite to-do list, try translating tasks directly onto your calendar with estimated time allocations. Remember to create open space: It is important to keep approximately 50% of your time open to accommodate unexpected events or spontaneous activities. This will allow you to improve your estimation skills. Over time, you will become more accurate in estimating the time required for tasks, allowing for better planning and utilization of time.

Pathfinders’ Spotlight

Fellow Pathfinder hype links and shoutouts.

offscript - by Priya Rose () - As someone constantly interested in the way we live and work, I’ve always wanted to work at the intersection of technology and architecture, but just haven’t found the right opportunity. Priya has shared and operationalized some of the most interesting ideas about the future of living. If you’re at all interested in the idea of co-living or Scenius, check out her work. I’d recommend starting with her post on How to Live Near Your Friends. Check it out ↗︎

Interested in getting a shoutout? Just shoot me a note.

And, just in case you missed it…

Here are some things that I’ve written and shared that people enjoyed.

Until Next Time!

That’s it for this week. As always, if you like the content, please do me a favor and like, share, subscribe — this newsletter runs on overpriced whiskey and reader engagement.

If you liked this post, I’d really appreciate it if you share it!

Share Path Nine

Thanks for reading, and see you soon,

— Kevin K. (@kkirkpatrick)

Some of you know my wife and I moved back to Seattle this week. We spent the last three years building our house in Lake Chelan but it's taking longer than expected, much to our dismay. And so, as an act of self-preservation, we've moved back to Seattle to finish it from here. We have a better community here, which we need for the foreseeable future. 

Given the chaos of the move, I didn't get a chance to write up a newsletter this week. So, in lieu of a new article, I'm re-releasing an old classic: Parkinson's Law of Productivity. 

Moving, like any daunting task, reminds you that it takes as long as it takes. 

Enjoy the week!

Before we begin: If you’re reading this but haven’t subscribed to PATH NINE, hit the button below to join creative entrepreneurs that read PATH NINE to learn the strategies reshaping our work and lives.

Subscribe now

It’s a rainy evening in Seattle. I’m firmly planted in my desk chair, wine glass in hand, staring at a list of unchecked to-dos, each one nagging away at my sense of weekend productivity. These to-dos are not for the week ahead, they’re from the previous week/weekend.

It seems, no matter how hard I try, work finds a way to absorb all of my time. Any free moments are occupied by work-related emails, Slack messages, and documents. What used to be an active, segmented part of my day, is now every living moment.

Ring a bell?

A day comes, a day goes. The workday begins slightly earlier, and “ends” slightly later, slowly absorbing any time not already dedicated to working. We continue to check off tasks, and yet, our sense of productivity continues to plummet.

This drudgery seems to be stuck on a never-ending loop, aka Groundhog Day.

A recent Families and Work Institute study reports that 75% of working parents do not have enough time for their children or each other. If that doesn’t say something about the state of work, I don’t know what will.

In 2020, a large percentage of the workforce was forced to work from home. Unfamiliar with the nuances of their new environment, many started out with a slight decrease in productivity. But that wouldn’t last long. People quickly found their stride and increased productivity, optimizing their work hours to maximize output. Many thought, “Hey, maybe this ‘work from home’ thing will give me more time outside of work.”

And yet, somehow, here we sit, having flooded our task list day-in and day-out for the last 9 months without feeling more productive, balanced, or fulfilled. The work seems to be sucking the air out of our lungs, one action-item at a time.

This, my friend, may in part be due to our sinister friend, Parkinson’s Law.

What is Parkinson’s Law?

Parkinson’s Law is a term first coined by Cyril Northcote Parkinson in a fantastic essay he penned for the Economist in 1955. What has since been aptly named Parkinson’s Law refers to the maxim that work expands to fill the time allotted. In other words, the work required to complete a task automatically adjusts to fill the time we initially allocated.

For example, if I set aside 5 hours each week to write an article, I’ve practically guaranteed that the article will in fact take at least five hours. Here’s why.

Five hours each week should be enough to draft, edit, and publish an article. But, because I know that five hours is enough time, I expand the scope of my article. What starts out as a simple, straightforward point turns into a complex argument filled with unnecessary tangents and nuanced points. (See, even some sentences fall prey to Parkinson’s Law.)

Work is like a gas — it fills the vessel in which it is contained. What originally started as a project with a fixed amount of time allocated, quickly shifts to a project with a minimum of five hours and a maximum that is “to be determined”.

This is the core premise of Parkinson’s Law.

Why We’re Particularly Susceptible to Parkinson’s Law

It’s easy to assume that we’re all just losing a battle to procrastination. But it’s far more complex than that. And the complexity we experience at work is growing exponentially.

We Shape Our Tools, and Thereafter Our Tools Shape Us

— Marshall McLuhan

As humans, we often look to technology to reduce and manage complexity. Unfortunately, we’re really good at creating tools that actually create more work. The sad paradox is that the more we work to reduce work, the more work we actually create for ourselves.

For example, let’s say you need to manage a project. You could start by using one of the most common and easy to use tools for project management — a spreadsheet. Ok great, we’re all set, right? What if you want to see your tasks in a calendar view? Now it’s time to go look for a purpose-built app that has this feature already built in. With a new app selected, you start creating tasks. Now you need to communicate those to your team. Ah shoot, I guess we need to invite more people. Now they’re adding tasks and contributing. Before you know it, what started as a simple project with a simple set of tools is now an overburdened process.

Whether it’s productivity apps like Sunsama, calendaring apps like Clockwise, or video conference tools like mmhmm, we’re working really hard to keep working really hard.

To go back to our gas metaphor, the work we create for ourselves is what fills our time. We don’t need to constantly create and deliver as much as we do, but because we’ve allocated the time (and space?) we feel obliged to do so.

Really what we’re struggling with is a never-ending flood of this thing we call “work.”

This is a recent phenomenon, driven by our confluence of digital tools, remote work, and our knowledge worker ‘work environment.’ When we work from home, we welcome work into our lives in a way we’ve never done before. It’s a house guest that we hoped would be kind enough to leave once they had overstayed their welcome. But here we are, months later, and they’re still using our toothpaste and eating our snacks.

Every minute we let work stay in our lives is another moment we’ve lost to actually living.

How to Keep Parkinson’s Law at Bay

Knowledge is power. But being powerful and lazy is pretty useless. While it’s great to know about Parkinson’s Law, we still have to practice preventing it from battling back into our lives. Furthermore, we should aim to actively avoid and prevent it.

The best path to successfully fighting Parkinson’s Law is to have a ready-made toolkit and a plan. There’s no one-size-fits-all answer to a complex problem, but there are a few principles:

Use the 5/25 Rule to Set (and Reset) Clear Goals

When we believe we need to fill time, it’s easy to get distracted and start adding mindless, unproductive tasks to our to-do list. That’s also the most dangerous thing we can do and what allows Parkinson’s Law to take over. To fight the urge to just keep working, I recommend using Buffett’s 5/25 Rule to increase your focus. It’s a simple 3-step rule (and tool) that I walkthrough here.

Define Your Work-Life Boundaries

Finding work-life balance is uncharacteristically difficult when we lose the natural physical distance between work and life. But boundary management is no longer optional. Employers and employees need to start developing competencies in work-life balance management to foster a better work environment for the future. Click here to learn what kind of boundary management is best for you.

Learn to Block Work and Life

Most individuals fail to protect and create space for their non-work needs. And why wouldn’t we be bad at blocking?

Prior to the last two decades, the four walls of our office created a natural blocking mechanism that automatically granted us freedom from constant work. But the world has changed a lot in the last two decades. Our work is now just one quick swipe away from our favorite past time. Our boss is literally in our homes at all times, ready and eager for a “quick sync.” If we don’t want to fall victim to Parkinson’s Law, we need to start learning to block for ourselves, our team, and our family. Here’s how to get started.

Manage Scope

There’s a Parkinson’s Law within a Parkinson’s Law message here; it’s called scope creep. The same way work naturally fills a lot of our empty time, project tasks and to-dos fill the time we allot for them. If you’re on a team, you’ve likely experienced this. You start with a set of goals and deliverables for a project, and then somewhere along the way you end up with a list twice as long. The easiest way to combat this is to write it down, sign it, and make it un-editable.

Enter, and Exit, Flow

Flow is the ideal work situation. Distraction is the enemy of flow. And right now, our world is very distracting. The issue with Parkinson’s Law is that it forces us to continuously try to stay in-flow. You can’t hit a home run every time you’re at-bat. You need to ride the pine every now and then, so we should actively seek both entering and exiting flow states.

Like any other goal, breaking it into small increments makes it easier to achieve the desired results. The steps in my recent article on flow can be used in any order and under changing circumstances. Don’t try just one; experiment, learn, and adapt.

Work doesn’t have to fill every square inch of your life. But for the foreseeable future, our employers won’t all be the shepherds of work-life balance. It’s up to each of us to create air pockets that allow us to breathe.

Until Next Time!

That’s it for this week. As always, if you like the content, please do me a favor and share it with your friends — this newsletter runs on overpriced whiskey and reader engagement.

Share Path Nine

Thanks for reading, and see you soon,

— Kevin K. (@kkirkpatrick)

My wife and I are currently enjoying a much-needed vacation in Hawaii. We’ve been going non-stop for the past two years, and we’re in need of a little time away. And yet, the thing that comes to mind amid this time is not a feeling of pause, but of pursuit. While I very much enjoy the downtime and relaxation that comes with a vacation, I love the way it reignites my fire, causing me to reflect on the entire idea of balance and moderation.

A few years ago I started thinking about how best to catalyze chaos amidst the ever-changing world in which we find ourselves. Well, it’s been three years and while things are definitely different, one thing hasn’t changed: our collective appetite for work. So today’s article is about moderation, and whether it’s necessary for everyone.

Before we begin: If you’re reading this but haven’t subscribed to PATH NINE, hit the button below to join creative entrepreneurs that read PATH NINE to learn the strategies reshaping our work and lives.

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Every Monday morning, I sit down at my desk, turn on any Tycho album, pull out my trusty notebook, and plan my week.

This little daily ritual keeps me focused and grounded.

It’s something I try to stick with every weekday, because it helps me avoid overcommitting to too many meetings, too many to-dos, too many agreements.

But recently I realized something: it doesn’t actually work.

Well, it works, but not as intended.

I know this, because I finally sat down and looked at the data.

As one of those OCD people who tracks their time, manages an overly-complex Notion workspace, and uses best-in-class productivity tools like Sunsama and Rize, I have the data.

At the beginning of each new year, I reflect on what I’ve accomplished in the last twelve months and what I’d like to tackle in the coming year. During this practice, I evaluate not just how much I completed, but how I felt about what I completed, and how much effort it took to complete everything.

This year, when I looked at my stats, they were pretty staggering. I’d worked an average of 50-60 hours each week, taken 2-3 weeks off, and only completed 60% of the goals I’d set out to accomplish at the beginning of the year. All in all, it didn’t look great. And yet, my feelings told a different story.

I felt accomplished.

I felt energized.

I felt ready for more, not less.

For most, the outcome of a process like this leads to a goal of working less, scaling back, or finding ways to optimize. And I’ll admit that, for most, this is the right outcome. I’ll play along with the typical work-life balance narratives that even I espouse on a regular basis. Yet, when it comes down to it, my ambition won’t rest. The list of objectives for the coming year just gets longer and longer. And before you tell me about the 80/20 rule, Buffett’s 5/25 rule, or any other prioritization framework, know that I both know these and still find myself in the same situation.

Because, the truth is:

I willingly overstretch myself.

On any given day, I find myself toggling between:

• two monitors

• three books in progress

• dozens of article or newsletter drafts

• hundreds of open browser tabs

• thousands of ideas

For me, chaos breathes life into an otherwise mundane existence.

In fact, managing the chaos often feels like a dance does.

You can learn to dance by following step-by-step instructions; right hand on your partners shoulder, step forward with your left foot, slide your right foot across…and so on. Or, you can watch someone dance and find your own groove. Instead of resisting your natural flow, you can learn to embrace it and move with it.

If you are resisting something, you are feeding it. Any energy you fight, you are feeding. If you are pushing something away, you are inviting it to stay.
— Michael Singer

My fragmented, overworked, chaotic existence goes against all conventional productivity advice and breaks all norms. Most people simply cannot understand how—or why—someone would be a willing participant in such circumstances, especially when it comes to work. We’re willing to accept and embrace a lack of moderation when it comes to particular hobbies, passions, religion, and so many other aspects of modern life.

And yet, when it comes to work, the modern narrative tells us to cut out as much as we can.

Like sugar, work is best consumed in small doses, only when necessary.

While work might produce a nice, temporary high, enjoy too much and you’ll crash.

Or at least that’s what we’re told.

But creative work is different. And makers of all kinds — painters, artists, musicians, etc. — often find that creativity blurs the line between what is considered work, and everything else. Putting artificial constraints on your creative brain, telling it to turn off, rarely works.

Constraints are incredibly powerful tools for creativity. But creativity and innovation aren’t always about limitations. In fact, creativity and innovation often come from connecting disparate ideas or concepts. As David Epstein points out,

Modern work demands knowledge transfer: the ability to apply knowledge to new situations and different domains.

The transfer of knowledge and the ability to apply it across different domains requires expansion, not contraction. The constraints of typical productivity advice turn moderation into frustration. Which is exactly why I choose to accept life without moderation.

Where you see chaos, I see creativity.

Where you see obstacles, I see opportunities.

And, when it comes to work, my brain wants more.

As I wrote in 2020, I think this is crucial for most people to find ways to do the minimum amount necessary to get the most monetary value for themselves. It’s the most logical way to approach anything so transactional: maximize ROI.

But the I in ROI isn’t the same for everyone.

I’ve come to realize that moderation just isn’t for me. And it’s not easy, but nothing in life is easy. Instead of fighting it, I’ve learned to harness it and use it to my advantage.

Accepting and integrating chaos might be the fastest way to find the signal of creative inspiration. Whether it’s work, a hobby, a book, or a creative endeavor, keeping your momentum is the key. If you let doubt or fear stop you, it just might bring all other creative outlets to a screaming halt. Take on more than you think you can handle, and see where each permutation takes you.

And, just in case you missed it…

Here’s a few related posts I’ve written that people enjoyed:

Until Next Time!

That’s it for this week. As always, if you like the content, please do me a favor and share it with your friends — this newsletter runs on overpriced whiskey and reader engagement.

Share Path Nine

Thanks for reading, and see you soon,

— Kevin K. (@kkirkpatrick)

Welcome to this week’s Path Nine Reflections and Recommendations. Each issue aims to enhance your thinking, lifestyle, and work by sharing distilled reflections and recommendations from the past two weeks. If you missed last week’s issue on Munger's Laws you can find it here.

Don’t feel like scrolling? Here’s the tldr version:

• Reflection: Slow it down.

• Rec: Product, Tool, or Framework: 15 Minute Hourglass.

• Rec: Read: In Praise of Slowness by Carl Honoré.

• Rec: Watch: "The Art of Slowing Down in a Fast-Paced World."

• Rec: Listen: Cal Newport on knowledge work, Part 2: “Slow productivity”.

Have a calm, productive, and creative week!

Before we begin: If you’re reading this but haven’t joined the PATH NINE community, hit the button below to join creative entrepreneurs that read PATH NINE to learn the strategies reshaping our work and lives.

Subscribe now

Reflections

◎ Slow It Down

Patience is a funny thing.

When we need it, we don’t have it.

When we have it, it feels like we don’t need it.

Like trying to force ourselves to sleep, forcing ourselves to be patient often just makes us more anxious. Or at least that’s what happens to me.

I won’t pretend to be the type of person who is always in a rush. I wasn’t in a hurry to get anywhere for most of my life. I felt relaxed and patient with the way life unfolded. Part of that feeling came from a general sense of internal contentment and a lack of time anxiety.

Now, as I feel myself aging past the days when I can say “oh, I’m still so young,” the pressure to move quickly seems to have crept up on me.

Where I used to feel comfortable sitting and just reading a book, I now feel pressure to go create, make something, and “be productive.” When someone asks to hang out, I think about whether or not that’s the best use of my time.

But this sense of urgency and question of productivity robs me of a real authentic sense of accomplishment, a kind of slow productivity.

There are different versions and definitions of productivity. Sometimes, it means cranking through every task on the list as quickly as reasonable. Other times, it means sitting in a chair, staring at the wall—leaving space for your brain to work it out.

Knowing which type you need is half the battle.

It takes some fundamental rewiring of our brains and body to understand what it feels like to enjoy slowness and operate at a different pace.

Instead of trying to brute force my way to being productive, I’m learning to live with the idea that being unproductive is a form of being productive. Sometimes, to go fast, we must first slow down.

You waste years by not being able to waste hours. - Amos Tversky

In the last year, many of the people I know have felt the unpredictable nature of the world closing in on them, creeping into their minds and manipulating their bodies. For some, it’s as though time is moving through us, not the other way around. The rapid pace of change has been jarring, to say the least.

Where we used to find time around the holidays and New Year to rest and recover, many felt a sense of continuity, a lack of pause. For all our pleading, the world seemed uninterested in our pleas to stop time.

And though we may wish to stop it, we cannot.

But maybe we can take some control. Maybe we can find a way to adjust our pace, and in doing so, live a little better.

Like eating a great piece of cake, work requests not that we speed up but that we instead slow down and enjoy it, for every bite is worth savoring. We aren’t robots, and we shouldn’t operate like them.

Recommendations

✪ Rec: Product, Tool, or Framework

15-Minute Hourglass

From Pomodoro, to 90-minute sprints and time-blocking, there are a lot of different time management techniques that people enjoy. I’ve tried most, and they’re all useful in their own right. But sometimes, you need a simple, analog way of doing things. Ugmonk makes some fantastic products for slow productivity, but their 15-Minute Hourglass is one of my favorite pieces. Like all of their products, it seamlessly blends form and functionality into an artful, tasteful piece worthy of placing on your desk.

✪ Rec: Reading

In Praise of Slowness by Carl Honoré

The slowness movement always sounded silly to me. As I alluded to above, the idea of slowing down feels so counterproductive. But Honoré changed my mind.

Honoré critiques the modern obsession with speed and argues we all need a more balanced approach to modern life. Having worked in tech for over a decade, I know that most people I interact with daily struggle to create balance and space. They struggle to turn off their work brain.

Every deadline: urgent.

Every project: overdue.

With every passing day, the work just continues to grow, and all we want to do is race to catch up.

And if you’ve every felt this, it’s time to read Honoré’s book.

✪ Rec: Watching

TED Talk - "The Art of Slowing Down in a Fast-Paced World" by Carl Honoré

This talk delves into slowing down in a culture obsessed with speed. It provides a compelling perspective on the pitfalls of constant optimization without considering the broader implications. As noted above in my reading recommendation, In Praise of Slowness encourages readers to reconsider the value of speed in their lives and offers practical insights into how adopting a slower pace can lead to a more fulfilling and meaningful existence. Honoré's narrative combines research, personal anecdotes, and examples from various cultures.

✪ Rec: Listening

Cal Newport on knowledge work, Part 2: “Slow productivity”

Productivity advice can be incredibly useful, or entirely useless. It can be filled with insight, or lacking any at all. Cal Newport repeatedly comes to play. His assessments and analysis of the modern-day worker repeatedly hits the mark. Further, he doesn’t just accept things and move on. He rethinks traditional notions of productivity, particularly in knowledge work, and highlights the importance of social skills, technology integration, and continuous adaptation to changing work environments. If you want to be more productive, without falling into the overly optimized path of r/productivity, listen to this podcast.

Pathfinders’ Spotlight

Fellow Pathfinder hype links and shoutouts.

The Clearing - Katherine May - a writer, a thinker, and someone who I imagine would either intellectually or naturally support the idea of ‘slowness,’ Katherine’s work is creative, inspirational, and calm. Her newsletter is filled with insights and tidbits from her journey as a writer and creator. Whether you’re looking for a thoughtful journaling prompt or an inside look at how a writer starts a new book, her work is worth your time on the path to slow creativity. Check it out ↗︎

Interested in getting a shoutout? Just shoot me a note.

And, just in case you missed it…

Here are some things that I’ve written and shared that people enjoyed.

Until Next Time!

That’s it for this week. As always, if you like the content, please do me a favor and like, share, subscribe — this newsletter runs on overpriced whiskey and reader engagement.

If you liked this post, I’d really appreciate it if you share it!

Share Path Nine

Thanks for reading, and see you soon,

— Kevin K. (@kkirkpatrick)

Welcome to the 11 new subscribers who joined since my last newsletter on the Reflections, Plateaus, and Fresh Starts from 2023—thanks for joining! Each issue of Path Nine is packed with takes on work, productivity, tech, and entrepreneurship to help people and companies do your best work

This week, as a follow up to Eat a Bit of Candy, I’m diving deeper into the man, the myth, the legend: Charlie Munger.

Alright, let’s dive in.

Before we begin: If you’re reading this but haven’t joined the PATH NINE community, hit the button below to join creative entrepreneurs that read PATH NINE to learn the strategies reshaping our work and lives.

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Charlie changed my life.

I felt I knew him, even though I didn't.

I discovered Seeking Wisdom when I was 25, and it was all I needed to be a lifelong Munger follower.

I devoured every book, interview, and speech that featured him. I left no stone unturned when it came to studying the works of this great thinker, spending countless hours capturing his quotes and ideas into my notes database. In a weird way, I guess I hoped that writing his thoughts would improve my own. That they’d embed so deep in my subconscious that it'd make me a little like Charlie.

And in some ways, it worked.

I learned to sit with my thoughts long enough to realize how bad they can be.

I learned to keep things simple, even when pushed to overcomplicate.

I learned that simple communication of complex ideas is an art.

I learned the intricacies of finance, investing, and mental models.

Though I learned a lot, something else stuck with me as I got older. What stuck with me wasn't the reflections and insights, but Munger's inevitable legacy.

As I've grown older, I've started thinking more about legacy. I've seen how great leaders, thinkers, artists, and creators reshape the world, and leave their mark. Even after death, their legacy lives on.

My fixation on legacy emanates from the dialogue it creates with the past, present, and future versions of me. Thinking about your legacy can be narcissistic, or it can be motivating. When I think about it, it's not through the lens of self-indulgence or flattery. Instead, it's to remind myself that everything I do will be part of my legacy, for good or bad. In that way, it is up to me to decide what to do with my time.

Do I choose to create in a way that cements a legacy I can be proud of?

Munger's work was an early inspiration for Path Nine, which became my humble attempt to create and solidify a legacy of my design and thinking. Munger's unwavering character, intelligence, honesty, humility, and professional success fueled my imagination and motivated me not just to work but also to think better.

The Depths of a Great Thinker

Great thinkers are rare.

Charlie Munger was the black swan of modern thinkers.

As I wrote in Eat a Bit of Candy,

Munger saw life with a lot of clarity. He's a thousand-yard stare in human form; focused, precise, resolute.

Munger was the right-hand advisor to the infamous and equally brilliant Warren Buffett. Where Buffett was best known for his financial success and avuncular attitude, Munger was known for his worldly wisdom and insight. No matter your experience or background, it's easy to derive value from the insights he shared across his 99 years of calculated, thoughtful, and intellectual rigor.

He was a man who somehow existed inside and outside of time's bounds. His wisdom wasn't some cheap tweet or cursory snippet pulled together for a soundbite. His thoughts were deep, nuanced, and colorful. His advice wasn't meant to be advice but to communicate a more profound truth. Munger's currency of choice wasn't advice; it was wisdom.

Unfortunately, we lost this great thinker in 2023.

Munger's legacy became more apparent and essential after his passing, as the invaluable wellspring of insights in his brilliant mind ceased to flow. No longer was it possible to get just one more quote or idea. That was it, the end.

Upon passing, countless writers, thinkers, influencers, business leaders, tech bros, and finance execs posted their thoughts, noting Munger's impact on their lives. And before the dust settled on the digital obituary, the listicles and roundups came flying in. If you're so inclined, here are a few:

• 6 longevity tips Charlie Munger believed in for a long and happy life

• 17 Charlie Munger quotes that teach us invaluable lessons about investing and life

• 'Diworsification' and lifelong learning: 3 quotes from Charlie Munger that will make you a better investor

Most of the memoriam posts about Munger focus on some of his most influential insights and quotes, partly because it's the easiest way to pump out an article that gets clicks (we all love an easy win, especially if it requires minimal thought and work, for that matter). Yet, reading each article made me feel more disconnected from the richness of his thinking. A series of quotes can be interesting, but it robs us of the depth we long for and associate with great thinkers. Ironically, most of what was written and shared was antithetical to Munger's belief that everyone isn't just handed cheap, easy wins. Munger said:

I believe in the discipline of mastering the best that other people have ever figured out.

What makes the life—and legacy—of Munger so uniquely interesting? Our ability to relive not just his ideas, but the ideas he co-authored by mastering the best of what other people already figured out.

Through his legacy, we can continue to learn and grow, as I did when I was 25, devouring every word and idea he shared with the world. Ideas that expand on the knowledge he harnessed through other great minds over decades of continuous learning and ideation. We can leverage his legacy to impact ours.

He wasn't overly concerned with being well-known despite his massive success.

He focused on mastering the best of what other people already figured out.

And his pursuit of mastering the best rings loud in my ears.

So, instead of regurgitating Munger's thoughts, I decided to go deep and summarize his thinking into a précis, or a summary of the anthology of Munger.

Developing Munger’s Laws

This piece is my attempt to curate and synthesize 99 years of next-level thinking to serve as a pairing-down of a seminal body of work. It's not meant to be a comprehensive breakdown of Munger's work—there are books for that, after all (Poor Charlie's Almanac, etc.)—but rather a dilation of the lens with which we view and embody his work.

In the process of endlessly digesting Seeking Wisdom and Poor Charlie's Almanack, watching "The Psychology of Human Misjudgment", and devouring every article I could find on Munger, I stumbled upon natural groupings that define this anthology. These are what I call "Munger’s Laws."

Laws that uphold his wisdom.

Laws that remind us of his character, intellect, and generosity.

Laws that, above all else, cement his legacy.

Law 1: Avoid Stupidity

It is remarkable how much long-term advantage people like us have gotten by trying to be consistently not stupid, instead of trying to be very intelligent.

We recognized early on that very smart people do very dumb things, and we wanted to know why and who, so that we could avoid them.

In life, our primary law should be geared toward avoiding stupidity. It’s an evolutionary concept that goes back to the earliest days of every living being. In this Darwinian view, we must evade what could take us out of the game to survive. As Munger once said,

All I want to know is where I'm going to die, so I'll never go there.

At work, most of what we aim to do is to look smart, when in reality, we’d be better off if we tried to avoid stupidity. If you look at some of the most successful people, they’re rarely the smartest or even the most qualified, at least in a traditional sense. During his commencement speech at USC Law School in 2007, Munger stated:

I constantly see people rise in life who are not the smartest, sometimes not even the most diligent, but they are learning machines. They go to bed every night a little wiser than they were when they got up, and boy, does that help, particularly when you have a long run ahead of you.

Dropouts like Thomas Edison, Mark Twain, and Steve Jobs all found success via non-traditional paths by simply putting their head down and focusing on getting a little better each day. Reflecting early and often is one of the best ways to avoid stupidity.

Law 2: Master Compound Interest

Everything starts small. But compound interest turns small things into massive things; it just takes time. Compound interest is a powerful concept that can bring immense benefits to our lives. It helps us earn not only on the initial amount invested, but also on the accumulated interest. Munger knew this like the back of his hand, and he saw how it impacted everything around him, from investing to the growth of every living organism—he saw it everywhere.

Understanding both the power of compound interest and the difficulty of getting it is the heart and soul of understanding a lot of things.

But, as he points out, our ability to comprehend the power of compound interest holds us back from making better decisions. Whether in finance or other areas of life, we can leverage this power law to achieve more significant growth and success. We can continuously learn and combine our skills to accelerate our progress and achieve remarkable results. Just remember what Charlie said,

I think that a life properly lived is just learn, learn, learn all the time.

Law 3: Allocate Time to Think

We pride ourselves on our ability to do. We use phrases like “bias for action” and “be proactive” to describe and encourage people to dive headfirst into something, putting thinking aside. As someone who studied architecture and spent the early days of my consulting career thinking, I’ve always found this to be counterintuitive and, at times, counterproductive. You can’t just start building a house and figure it out as you go. You need plans, details, drawings, annotations, and coordination—all things that require thinking.

Neither Warren nor I is smart enough to make the decisions with no time to think.

In his article “In Defense of Strategy,” Packy McCormick does a fantastic job articulating the value of strategy and thinking. The art of clear thinking doesn’t come from the unpracticed; it comes from those obsessed with exploring the depths of their mind, expanding boundaries, pushing limits, testing ideas, and, most importantly, creating space. Only once we have opened up space and time for thinking can we roam the land without restriction.

If you want to be a good thinker, you must develop a mind that can jump the jurisdictional boundaries.

Law 4: Stay Grounded

When starting my first company, one phone call left a lasting impact on me. I met with a fellow founder who had just sold their software company to a mid-sized tech firm in Seattle. What struck me was not the shared insights or advice but the arrogance I felt dripping off every curt or cryptic reply. Though I was still a young entrepreneur, I swore that no amount of money would ever change me, or my ability to be kind and helpful. And it goes to precisely what Munger would say,

Remember that reputation and integrity are your most valuable assets and can be lost in a heartbeat.

Success shouldn’t change you. Find a way to stay grounded.

Law 5: Create Systems for Success

Munger is both a complex and an uncomplicated thinker. Like Buffett, he embraced both the simplicity of checklists, and also the complexity of a latticework of mental models.

No wise pilot, no matter how great his talent and experience, fails to use his checklist.

It's so easy to get so busy you no longer have time to think. The price of not thinking clearly is relatively high, albeit sometimes delayed. But when it comes to designing a life and a career, it’s important to remember that we need systems to help keep us accountable. Or, as the infamous James Clear puts it, “You do not rise to the level of your goals. You fall to the level of your systems.”

I think about this a lot. Every day, I look at what I’ve accomplished and try to find one optimization—one way to turn a manual process into something scalable, repeatable, and easy to follow. I don’t do this to simplify work, but to maximize space for creativity and deep thinking. It’s my way of looking for patterns that keep me on track and push me toward a more successful version of myself.

You’ve got to have models in your head. And you’ve got to array your experience—both vicarious and direct—on this latticework of models.

Law 6: Passion Amplifies Aptitude

Every week, I read a post on Reddit or Blind asking, "What is the highest-paying job in tech?" Inevitably, these questions are commonplace on platforms that promote financial success as the critical metric for a well-crafted life and career. We should expect no less from a society that cares little about the creative, alternative forms of success that often create the most fulfilling lives and careers. But we certainly shouldn't embrace it.

The problem with these questions is that they rarely lead to a successful career. Say you decide to be a doctor because it pays the highest salary; what happens when your passion dies out or you lose the motivation to keep moving?

What happens when lifestyle creep catches up to you, and you get stuck in a system you hate?

What happens if it causes everything else in life to fall apart, and your family leaves you?

You’ll do better if you have passion for something in which you have aptitude. If Warren had gone into ballet, no one would have heard of him.

The realities of a life and career well-crafted are that they require the delicate intertwining of passion and aptitude; your interests need to meet your skills. It doesn’t need to be a 50/50 split but involves integration. The sooner you realize that moving interests and skills closer together in the Venn diagram of life, the sooner you’ll find yourself in a place that few can replicate, but many will attempt to emulate.

Law 7: Choose Your Challenges

Starting a new business, building a new career, or doing something people don’t understand well or that doesn’t fit into a nice, neat box are all high-risk, high-reward paths in life. But they’re filled with triggers for self-doubt, imposter syndrome, and frustration. All paths are challenging. The question is: what kind of challenge should you choose?

Whenever you think something or some person is ruining your life, it's you. A victimization mentality is so debilitating.

At some point, we have to chin up and move forward. Life gets hard fast. As I look back on the adversity I’ve faced in starting, growing, and building companies, it’s easy to be overwhelmed by the challenges and frustrations faced along the journey. Yet, each has made me better, and therefore made me stronger. For every mistake I made, I found two new ways to improve on that in the future. No matter how bad things seem, there is always a way, and a victimization mentality isn’t a solution.

Law 8: Avoid Mediocrity

Most creative people are cursed with a distinct kind of pain: the pain of optionality.

Being creative often leads to multiple ideas, at times in rapid succession. It’s easy to get excited and distracted all at the same time. There are many things to pursue, and the creative brain sees opportunity everywhere. But without limitation, we risk sending ourselves into a death spiral of projects and ideas that never exceed 10% completion. As Ned Rorem once said, “It isn’t evil that is ruining the earth, but mediocrity. The crime is not that Nero played while Rome burned, but that he played badly.”

And Munger reminds us of the same pains and pitfalls of mediocrity, saying:

It takes character to sit there with all that cash and do nothing. I didn't get to where I am by going after mediocre opportunities.

In Thriving with Limitation, I shared the creative limitation that artist Pierre Soulages, "The painter of black and light," was known for creating some of the most fascinating, minimalist, abstract art in the 20th century. He often felt overwhelmed by choice — materials, colors, subjects, it was all too much. In 1979, he made the radically divergent choice to reduce his palette to one hue: black. We can learn a lot from Soulages. Whether you’re thinking about starting something, building something, or continuing something, constraints are a way to keep you grounded—they allow for and breed creativity.

Law 9: Learn to Rise

Those who keep learning, will keep rising in life.

The first step to rising is realizing we can evolve—we're capable of change and maturation. Munger saw mistakes as the leavening agent in human maturation, providing the necessary conditions to encourage and facilitate intellectual expansion.

I like people admitting they were complete stupid horses’ asses. I know I’ll perform better if I rub my nose in my mistakes. This is a wonderful trick to learn.

We must first face ourselves, before we can face the world.

Forgetting your mistakes is a terrible error if you’re trying to improve your cognition. Reality doesn’t remind you. Why not celebrate stupidities in both categories?

Mistakes are part of growth. Remember them. Learn from them. Reflect and move on.

Law 10: Keep Life Simple, and Minimal

One of the greatest ways to avoid trouble is to keep it simple. When you make it vastly complicated—and only a few high priests in each department can pretend to understand it—what you’re going to find all too often is that those high priests don’t really understand it at all…. The system often goes out of control.

We have a passion for keeping things simple.

We have three baskets: in, out, and too tough… We have to have a special insight, or we’ll put it in the too tough basket.

Simplicity is something I just recently started to understand. When studying architecture in college, I remember a long and detailed discussion with a professor about the differences between simplicity and minimalism, and their relative importance in architecture. To the best of my recollection, the assertion was:

• Simplicity = bad.

• Minimalism = good.

And from that point forward, I only referred to anything in architecture as minimal, never simple. But as I recall, the point was slightly more nuanced and focused on minimalism as a stripping down of elements. Conversely, simplicity resulted from an underdeveloped idea requiring more analysis and study, leading to a less considerate design.

Architecture lessons aside, when it comes to decision-making, simplicity is my north star. My gut usually knows the answer, and my brain tries to convince my gut that it knows nothing. Of course, I’m always an advocate for Second-Order Thinking and in-depth critique, but sometimes, they can stand in the way of what would ultimately be a straightforward decision.

If something is too hard, we move on to something else. What could be simpler than that?

Learning to Leave Your Mark

For all his profound wisdom, Munger was nothing more than a man.

He sweat, bled, cried, laughed—and ate a bit of candy.

His wisdom lifted me and kept me planted firmly on the ground.

His fingerprints are all over my work and my life.

He left a mark.

Though imperfect, Munger’s laws provide foundational principles that can be passed down from generation to generation. These laws are a great place to start if we wish to think, work, and live better in the next 99 years. He was incredibly thoughtful, successful, and yet entirely grounded—and that’s exactly how I want to be remembered.

"Do not seek to follow in the footsteps of the wise, instead, seek what they sought." —Matsuo Bashō

That’s how he beat the market, outlasted the competition, and built a legacy.

Had he not been a billionaire, he’d still be successful.

Because the man, his morality, and his modus operandi surpassed the heights of his fortune.

His legacy lives on.

And, just in case you missed it…

Here’s a few related posts I’ve written that people enjoyed:

Until Next Time!

That’s it for this week. As always, if you like the content, please do me a favor and like, share, subscribe — this newsletter runs on overpriced whiskey and reader engagement.

If you liked this post, I’d really appreciate it if you share it!

Share Path Nine

Thanks for reading, and see you soon,

— Kevin K. (@kkirkpatrick)

Welcome to this week’s Path Nine Reflections and Recommendations. Each issue aims to enhance your thinking, lifestyle, and work by sharing distilled reflections and recommendations from the past two weeks.

Don’t feel like scrolling? Here’s the tldr version:

• Reflection: Don't Break the Chain (aka the Seinfeld Method).

• Rec: Product, Tool, or Framework: WritetoGrow.

• Rec: Read: Grit: The Power of Passion and Perseverance by Angela Duckworth.

• Rec: Watch: Success, Failure, and the Drive to Keep Creating TED Talk.

• Rec: Listen: The Time Ferris Show: Jerry Seinfeld — A Comedy Legend's Systems, Routines, and Methods for Success.

Have a calm, productive, and creative week!

Before we begin: If you’re reading this but haven’t joined the PATH NINE community, hit the button below to join creative entrepreneurs that read PATH NINE to learn the strategies reshaping our work and lives.

Subscribe now

Reflections

◎ Don't Break the Chain (aka the Seinfeld Method)

‘Never give up!'

'Don't let the fear of striking out keep you from playing the game.'

'Don't quit!'

These phrases have been beaten into us relentlessly. They're the focus of the inspiration posters that line the halls of our doctor's office, liberally sprinkled throughout legendary speeches, and a hallmark of our favorite sports movies.

But when it comes down to it, they're just words.

The problem with these phrases is that they offer macro-level advice for a micro-level problem. They tell you to climb the mountain, not take another step toward the summit.

Amid difficulties, not quitting becomes a statement of personal conviction and determination.

Not quitting is a mindset, a conscious decision to persist even when the journey becomes difficult or impossible. It involves embracing the discomfort of uncertainty, facing the fear of failure, and pushing through moments of doubt.

The "Don't Break the Chain" method, also known as the Seinfeld Method, is a productivity strategy that involves committing to a daily goal and marking an "x" on a calendar for each day the goal is accomplished. Although he claims no association with its creation, this strategy was initially inspired by legendary comedian and creator Jerry Seinfeld (featured below in the recommended listening).

Research has shown that 'grit', characterized by perseverance and consistent effort, increases engagement and academic achievement in adolescents. Shockingly, the same research also found that goal commitment plays a more important role than a growth mindset.

Creating a chain of consecutive "x's" makes the streak visually rewarding and motivates you not to break the chain. The method focuses your brain on small, achievable steps that move you closer to a goal, one step at a time. It also takes your mind off the goal and allows you to focus on actions. Further, this method activates the brain's reward system and harnesses the power of small wins.

Consistency is what separates those with dreams from those with big wins. Set the big goals, but focus on consistency and dedication—the rest will take care of itself.

Recommendations

✪ Rec: Product, Tool, or Framework

WritetoGrow

WritetoGrow is a product I recently stumbled upon via X (formerly Twitter). The app offers a unique and immersive writing experience that leverages the “Don’t Break the Chain” method to help writers increase consistency.

Here’s how it works:

1. log into the app

2. write for 2 minutes a day

That’s it.

While the app does offer other features that might be interesting and novel, its ability to enforce and create a writing habit might be its best feature. Whether you need a writing streak tracker or not, I hope this inspires you to break down your big goals and new year resolutions into manageable, little steps.

✪ Rec: Reading

Grit: The Power of Passion and Perseverance by Angela Duckworth

In her New York Times Bestseller, Angela Duckworth delves into what is colloquially known as 'grit.' As the daughter of a scientist and a psychologist, Duckworth shares valuable insights on how grit can be developed, irrespective of one's intelligence quotient (I.Q.) or circumstances. I love how she reframes such a simple concept and provides a compass for one to use grit to find their way out of the most challenging personal and professional conditions.

✪ Rec: Watching

Success, Failure, and the Drive to Keep Creating TED Talk

Elizabeth Gilbert, the renowned author of "Eat, Pray, Love," contemplates success, failure, and continual dedication to creative pursuits. Her speech inspires me to continue developing a resilient mindset that embraces achievements and challenges as part of the journey and softly reminds us, “Don’t Break the Chain.”

✪ Rec: Listening

The Tim Ferris Show: Jerry Seinfeld — A Comedy Legend's Systems, Routines, and Methods for Success

Seinfeld is a comedic legend. And Tim Ferris is a productivity expert. When the two meet, it’s like striking gold. In this podcast, Seinfeld reveals the secrets behind his greatness, consistency, and pursuit of perfection. If you implement the “Seinfeld Method,” shouldn’t you hear from the man himself first?

Pathfinders’ Spotlight

Fellow Pathfinder hype links and shoutouts.

White Noise by Tom White - White Noise is a newsletter written by (my friend) Tom White. Each week, Tom distills and compiles insights from his reading, listening, conversations, and personal experiences. His writing is inspiring, uplifting, and thought-provoking. It’s one of the rare newsletters that I make time for each and every week. Check it out ↗︎

Interested in getting a shoutout? Just shoot me a note.

And, just in case you missed it…

Here are some things that I’ve written and shared that people enjoyed.

Until Next Time!

That’s it for this week. As always, if you like the content, please do me a favor and share it with your friends — this newsletter runs on overpriced whiskey and reader engagement.

If you liked this post, I’d really appreciate it if you share it!

Share Path Nine

Thanks for reading, and see you soon,

— Kevin K. (@kkirkpatrick)

Happy holidays!

This will be the last post of 2023. I’m taking the rest of the year off to rest, reset, and recharge for 2024. While I was tempted to write a how-to guide for end of year reflections or a goal-setting and planning template, I figured why not end on a more sincere note; one focused on transparency, candor, and the hard lessons learned during a difficult year. Providing a little inside baseball on the path I trod, not just the path that lies ahead.

Though the reflections are brutally honest, they’re not intended to be disparaging or melodramatic. Instead, I hope they provide clarity and insight into the challenges that 2023 brought, and provide inspiration for a path that is honest and truthful. I find that diving into the depths of the emotional and intellectual oceans often yield the most beautiful pearls of wisdom.

Cheers,

Before we begin: If you’re reading this but haven’t joined the PATH NINE community, hit the button below to join creative entrepreneurs that read PATH NINE to learn the strategies reshaping our work and lives.

Subscribe now

2023 was a weird year.

It was challenging, frustrating, liberating, and all in all, what Latin speakers might call, annus horribilis, or “a horrible year.”

Even if you're not familiar with Latin, the phrase speaks for itself.

This year was, one of the most challenging years in recent memory. While there were some incredible highs, there were some very real lows.

Both personal and professional work fell off a cliff.

I struggled to find the path forward for building our house.

I wrestled with the challenges of leading a team through the changing macro economic headwinds.

I found it difficult to keep the momentum of writing and building Path Nine.

The theme of this year was not just ups and downs, but false flats. A few years ago, I wrote about the idea of false flats, but if you’re not already familiar, here’s the short version:

A false flat is the stretch of road between two steeper sections of the same hill. Though it may look flat, the path is actually a low-gradient towards a steeper climb.

These sections are especially tricky for many cyclists, as they lure you into a false sense of security. Imagine pushing your body to the max as you race to the summit ahead. "Only a little bit further before I've reached the top," you think as you shift to a higher gear. Just as you approach the top, you realize it is, in fact, a false flat with another steep section that follows.

Your eyes believe it's the top. Your heart assumes you've made it. Your legs scream their own judgment, and your lungs confirm the sentence.

Throughout the year, I experienced a number of hiccups and false starts. As hard as I tried this year, and as soon as I thought I’d reached the top, I found another hill to climb. So this year, I’m reflecting on the hills I’ve climbed, conquered, and fallen down.

Plateaus for Contemplation

I spent a good part of this year unintentionally throwing out the lessons I had learned in all previous years. There were so many times I wanted to shake myself free of the madness, but I couldn’t seem to find the light. Instead of doing the work I needed to do, finding a way to balance myself, or just leaning into my values, I:

• stuck with projects that didn’t work,

• moved slowly, with caution,

• held myself back,

• wasn’t true to myself,

• and let projects take over my entire life.

When I see it listed out like that, it hurts. It feels like I’m talking about someone else, just as I’m about to give them a fresh dose of motivational advice. The hardest lessons aren’t hard because we can’t get through them, they’re hard because we can’t believe we let ourselves be in the position to experience them at all. That’s 2023 in a nutshell for me.

Some of these reflections are personal, others are professional. The imaginary space that exists between work and life is just that, imaginary. At the end of the day, we’re not separate beings who can turn our brains on and off of ‘work’ mode. Severance may or may not be a great idea, but it’s not real, yet. Integration of work and life is too messy, and often leads to unnecessary and unhealthy boundaries. Instead, I’ve learned to strive for a certain kind of harmony, one that bends with the winds, instead of resisting it. Just like climbing the hills of life, I’ve learned to be ready and adaptable to anything that comes my way.

So let’s start with the big, nasty, windy road that is the most challenging personal project I’ve encountered in my life: the house.

Plateau 1: Building a House

In 2021, my wife and I upended our life in Seattle. We left the urban lifestyle we’d built together, and uprooted to move to a small town in central Washington. At the time, I wrote about needing a change. Our plan was to build a house, live and work remotely, and build a different kind of life. In all honesty, a life I still believe in.

But then, 2023 kicked us in the face.

For those of you not within our inner circle of friends and family, let me quickly recap the timeline of events leading up to 2023:

• Nov. 2020 - we hired an architect to co-design our house.

• Mar. 2021 - we moved out of Seattle to Chelan.

• Sept. 2021 - we raced to break ground and start building our house before winter.

• Nov. 2021 - our build was delayed due to a heavy, but expected, snow storm (bad sign 1).

• Apr. 2022 - the build process finally resumed, but was 6+ months off schedule.

• Jul. 2022 - our concrete pour takes 3 months instead of 3 weeks (bad sign 2).

• Sept. 2022 - the day before our wedding, our builder demands we sign a change order (bad sign 3).

• Oct. 2022 - we’re harassed via text by our builder while on our honeymoon (bad sign 4).

• Nov. 2022 - luckily, our architect catches that our builder has altered our roof, without our approval (bad sign 5).

• Jan. 2023 - our builder starts demanding money for work that isn’t done (bad sign 6).

• Feb. 2023 - our builder realizes he’s in over his head, quits, and breaches our contract.

This was the beginning of a nightmare. Part of the nightware wasn’t just the experience, but the realization that we were being sucked into a sunk-cost fallacy, throwing good money after bad in order to complete our commitment. While we hated every moment of working with our builder, we were already 18 months into a challenging and expensive project, and we just wanted a place to live. A place we worked for, dreamed about, and committed to completing.

The process with our builder wasn’t like anything I had ever experienced. Vacations, holidays, important milestones were all intentionally interrupted and sabotaged by our builder. Any mistake made in the project, was somehow our mistake, not his. I won’t bore you with all of the gruesome details—a story for another time—but what I can say is that the rest of the year didn’t get better. We’ve had to involve lawyers, county officials, new builders, architects, engineers, and friends, family, and acquaintances—all people who shouldn’t have to care about our house. The project has effectively been on hold, and has absorbed so much of our life, while also doing significant damage to our savings and well-being.

We’ve felt trapped, incapable of moving for fear of the additional costs and complexities. Every time we thought things couldn’t get worse, they did. Every time we thought we could move forward, we got blocked. Every time we let ourselves breathe, the air left the room. It was hard to see any positivity in the experience.

Our dream house became our prison.

Insights gained on level ground: Be careful the IKEA/Endowment effect. It’s easy to get wrapped up in things we’ve built, and convince ourselves they’re more important simply because we’re building them. While I can’t share exactly what our plan is at this moment, I can tell you, it has changed completely. We are not getting stuck throwing good money after bad. We are not staying attached to it simply because we built it.

Plateau 2: Running a Business

I’ve worked at companies of all sizes, and gained incredible experience at every turn. From big consulting to starting my own companies, I’ve seen it all—and likely done it all. It’s helped me morph my skills as an ex-designer/architect into more business-oriented skills like sales, business development, growth/marketing, and, my least favorite of the bunch, finance.

But the bully of 2023 put me in my place.

2023 walked up to me in the school cafeteria, slapped my lunch out of my hand, gave me a wedgy, and shoved me into my locker.

The business I’ve been running for a few years hit a wall. Hiring fell off a cliff, companies put budgets on hold, and everything came to a grinding halt.

I had to do reduce costs across the board, and found myself and my team ‘doing more with less,’ (aka the theme of 2023). And while I know many businesses had it much worse, it really put me in my place. For the first time in years, I felt like the headwinds were so strong that I wasn’t sure if we could withstand them.

Now, I know that sounds a bit dramatic, and it is. At the end of the day, businesses come and go. They shift, they adapt, they change with the times. And we changed, we adapted. We launched new offerings, we built new revenue lines, we grew in other areas of the business. The clouds didn’t part, but we found the shapes that were interesting and made them into paintings that we could sell.

The lesson didn’t come all at once, but drop by drop in the center of my forehead, each drop doing just a little more damage, but not enough for me to overreact.

Insights gained on level ground: Continue learning to work with worry. Earlier this year, I wrote about the idea of working with worry—a concept I saw other colleagues and friends expressing across social media. With layoffs, hiring freezes, and peak job insecurity, work can be very destabilizing. But sometimes experiencing one thing that is destabilizing can provide focus and clarity to other areas in life.

Plateau 3: Writing This Newsletter

Path Nine turns 4 years old this year—a milestone I didn’t know how to celebrate. My relationship with the newsletter has grown increasingly complicated over the years. What started as an outlet for thought and conversation became an intake for stress, anxiety, and imposter syndrome. In 2019, I started writing as a way to share my experience and hopefully offer an alternative path for people who didn’t fit into the traditional mold, specifically in tech. Newsletters and online content initially felt like an open space for growth, learning, and sharing. I watched great thinkers and writers like Ben Thompson build the foundation for the wave of online writing that was to come. But soon, with the rise of Substack and the growing wave of influencers, writing online started to feel less like an intimate party and more like a crowded convention hall, filled with people selling you get-rich-quick schemes and cheap knockoffs of your favorite brands. It was hard for me to find my place in the chaos of this world.

Over the years, life got increasingly busy and other things got in the way. Or at least that’s what I tell myself.

The truth is: the slow progress didn’t fill up my ego enough to keep the momentum going.

I lost interest in something that didn’t feel like it was “succeeding.” Instead of just pushing through, making time and space to continue growing the newsletter and reaching my goals of writing something helpful, insightful, and meaningful to me, I stopped. Or, as I said to myself, I just put it on pause.

And look, I’m the first to support people taking a pause.

Balance is the antidote to burnout, and I wanted balance.

But, it came with a cost; a cost I felt deeply in 2023. The cost came in the form of not just lost subscribers and momentum, but a sense of meaning, self, and purpose. I felt that lesson every night when I went to sleep without writing. I felt it every day when I avoided reading a book, because I knew it would make me want to write more, and I didn’t feel ready for it. I felt it every time I read an article someone else wrote that I admired. The pain wasn’t in watching others succeed, it was in watching myself fail, or at least letting myself down.

Most people were still supportive. They’d ask “what’s up with the newsletter these days?” And my answers were a mumbling, self-conscious, half-hearted jumble of excuses and tropes about finding balance and reseting. In all honesty, they were just deflections.

Insights gained on level ground: find ways to have less to do.

My goal is no longer to get more done, but rather to have less to do. - Francine Ja

As I wrote earlier this year, this is the way. Instead of finding ways to fit more in, I’ll be cutting more out of my workload. I want to save space to continue writing this newsletter, as I see it as a critical part of a lifelong body of work.

Ascending to New Heights

I don’t want this to sound like a wasted year, or one I’m not grateful to have experienced. There were a lot of highlights: I read some great books, I did things I’ll never regret, and I stretched myself in ways that made me stronger.

If you're going through hell, keep going. - Winston Churchill

Sometimes the only way forward is through. It’s tempting to continue gazing backward, checking that rear view mirror for artifacts of a life left behind.

But there lies madness.

Moving forward isn’t about throwing things away, it’s about finding things that create a way. In my constant efforts to build an antifragile career, I see Path Nine as a critical element in a long-term strategy—a mix of building blocks that offer limitless potential for creation.

While there are a lot of unknowns in the future, there are some things I can promise going forward. I can promise to write and share honestly. Not just for the sake of likes or subscribers, but as a way to bring transparency and truth—at least my truth—to the world. Further, I hope that the honesty and transparency brings clarity and motivation for your path forward. In order to carve your own path, we must be willing to face the truth, both good and bad.

All that said, I want to ensure I’m being honest. So, here are some things I can’t fully promise:

I can’t promise that every article will land. That’s part of the issue with honesty—it doesn’t always resonate with everyone, at every moment. While I hope they do, forgive me if they don’t.

I can’t promise that I’ll keep the same format or stick to one genre. Life is messy, people are too. I pride myself on constantly learning and growing, which leads to many, sometimes divergent interests and ideas.

I can’t promise that I won’t ask for your help - in fact, I will. I don’t write just for myself, so I shouldn’t do it alone.

If you want to go fast, go alone. If you want to go far, go together. - African proverb

Look, I won’t pretend that it’s easy for me to ask for help. Anyone who knows me knows that I pride myself on being fiercely independent, typically to a fault. But here I am, hat in hand, asking for your help. If there’s anything I’ve learning in life, it’s that the Einstein Paradox is real, and worth paying attention to.

How you can support me:

• Like, share, subscribe.

• Share share share - I know I said “share” in the last bullet, but it’s important and helpful.

• Send feedback - I’d love to hear what you’re most interested in. Shoot me an email, add a comment, or just hit reply.

• Become a paid subscriber - it’s not the most important thing, but it is a helpful way to show your appreciation for the work that goes into this newsletter.

I have a lot in store for 2024—from the usual mindful productivity, to alternative ways of thriving creatively, to reimagining work altogether. I often find that when I feel like I’m at my lowest, it’s when I also feel most energized to push myself up that hill. While there were many false flats in 2023, I am ready and eager to push up the hills of 2024. I hope you’ll join me on the journey and ascend to new heights in the coming year.

Thanks for reading, and see you in the new year,

P.S. whether you’re founding a company, thinking about quitting your job to find something new, or already on a new path toward personal and professional harmony, I’d love to help. Please feel free to shoot me an email and let me know if you need support with starting your solopreneur journey, crafting compelling messaging, finding your market, or getting systems and mechanisms in place to help you focus on what matters.

As always, this week’s R&R is short, but if you don’t have time to read the entire article, here’s the tldr version:

• Weekly reflection: What is it you do? Reflecting on how we define ourselves.

• Rec: Product, Tool, or Framework: How Much to Make (calculator)

• Rec: Read: Sell Out (With Me, Oh Yeah)

• Rec: Watch: How Pieter Levels Makes $2.7M/Year With 0 Employees

• Rec: Listen: Prof G Markets: How Scott Manages His Money

Reminder, this is a way for me to clear the cognitive cobwebs and share the reflections and recommendations that I’ve pulled together for the last two weeks. No affiliate links or sponsorships here, just simple links to things I genuinely love and recommend. 

Alrighty, without wasting any more time, here are a few amazing things that will totally up your thinking, working, and living game.

Have an awesome week ahead!

Before we begin: If you’re reading this but haven’t joined the PATH NINE community, hit the button below to join creative entrepreneurs that read PATH NINE to learn the strategies reshaping our work and lives.

Subscribe now

Reflections

▶︎ What is it you do?

"What do you do?" This is such a tricky question to answer. At cocktail parties, dinner conversations, the dreaded networking events; they're all painful ways to conjure the existential question of 'what do you do?' Over the years, I've learned to reframe this question, but I still don't feel I've fully resolved the details in my head. For now, I've settled on using this combination of {impact} + {title or role I like} + {persona}. For example, I'm a productivity architect for creative leaders. It's not perfect, but it helps me think about how I can frame—or reframe—how I fit into my work. It also acts as a reminder that the work you do is singular to you. While you may have the same title as someone else, there are always ways to find your niche within a generalized space.

Rec: Product, Tool, or Framework

▶︎ How Much to Make (calculator)

I love a good calculator. And as an entrepreneur, I find it easy to get wrapped around the calculations of pricing and positioning without ever nailing down what you’re trying to accomplish. This calculator does the simple calculations, telling you exactly how much traffic you need to generate for your digital product based on how much you want to make. While we can all do these calculations, we rarely do. Before you launch or price your product, use this little tool to help you ensure you’re on the right path to hit your financial targets.

Rec: Reading

▶︎ Sell Out (With Me, Oh Yeah)

A lot of people hate marketing. Or at least they think they do. What they really hate is self-promotion, which is easily confused with marketing. As a creative person, it’s taken years for me to reframe my thinking about self-promotion. And, like anything else in life, it’s come down to how I frame it in my own mind. What drove this home for me this week was a post by where she dissects the age-old debate of selling out, reminding us that “Done well, marketing gets baked into the product being marketed.” It’s a beautiful reminder that when we think about our work, we can’t separate the creation or craft from the promotion. Promotion isn’t the enemy, just like marketing isn’t the enemy. If we want to reach the right people at the right time with the right offering, we have to think of marketing and, to some extent, self-promotion. Marketing, when done well, is genuine, functional, and beneficial. Please don’t shy away from it; embrace it.

Rec: Watching

▶︎ How Pieter Levels Makes $2.7M/Year With 0 Employees

If there’s one person on the internet who does a great job mixing craft and marketing, it’s Pieter Levels. Pieter is an entrepreneur’s entrepreneur. He single-handedly created some of the most profitable, scalable products known to digital creators. Not only does he run multiple incredibly profitable businesses, but he boldly shares all the gory details of running these businesses. Whether we’re talking about revenue, technical challenges, complaints, strategies, or growth hacks — Pieter shares it all. By sharing this, it builds community around him and helps him grow his products and businesses faster than he could. Pieter knows what his work is, and doesn’t waste time thinking; he takes action. He ‘sells out’ but in the best way.

Rec: Listening

▶︎ Prof G Markets: How Scott Manages His Money

Everyone has some form of financial frustration. Whether it’s not having enough to cover the bills, having enough to cover the bills but not saving, having a little extra but not knowing what to do with it, or something completely different, the struggle with money can be very real. Professor Galloway, a famed podcaster, educator, and sage mentor for the ambitious, has made a lot of money. And yet, he still has financial fears and frustrations. In this deep dive, he provides a backstage view of the finances of a multi-millionaire. Some of his advice may seem obvious, but some are incredibly unique. No matter your financial situation, his advice might open up a new way of living and looking at your finances, so listen.

And, just in case you missed it…

Here are some things that I’ve written and shared that people enjoyed.

Until Next Time!

That’s it for this week. As always, if you like the content, please do me a favor and share it with your friends — this newsletter runs on overpriced whiskey and reader engagement.

If you liked this post, I’d really appreciate it if you share it!

Share Path Nine

Thanks for reading, and see you soon,

Greetings from Memphis, Tennessee. I’m here with my family for the weekend doing a half-marathon for the St. Jude’s Memorial Race in honor of my late cousin, Stephen. If you feel like donating, if you feel free to do so here. Inline with last week’s article on Things You'll Never Regret, I can definitely say I’ve added this event to the list.

Last week, we lost Charlie Munger, one of the great investors and minds of the 21st century. So this week’s R&R is a sub-5 min read with some reflections and recommendations highlighting the wisdom he gifted us. If you don’t have time to read the entire article, here’s the TL;DR version:

• Weekly reflection: Eat a Bit of Candy

• Product, Tool, or Framework: Cognitive Bias Codex

• Read: Seeking Wisdom or Poor Charlie’s Almanack

• Watch: The Psychology of Human Misjudgement

• Listen: Acquired Podcast Interview with Charlie Munger

Reminder, this is a way for me to clear the cognitive cobwebs and share the reflections and recommendations that I’ve pulled together for the last two weeks. No affiliate links or sponsorships here, just simple links to things I genuinely love and recommend. 

Alrighty, without wasting any more time, here are a few amazing things that will totally up your thinking, working, and living game.

Have an awesome week ahead!

Before we begin: If you’re reading this but haven’t joined the PATH NINE community, hit the button below to join creative entrepreneurs that read PATH NINE to learn the strategies reshaping our work and lives.

Subscribe now

Reflections

▶︎ Eat a Bit of Candy

Charlie Munger’s intelligence was otherworldly; but his appetite for sweets was his true kryptonite. In a memorable CNBC interview last February, Charlie Munger offered a delightful and seemingly unconventional tip:

I'm eating this good peanut brittle,' he said with a grin. 'That's what you want to do if you want to live to be 99.'

Munger's remarks aren't just a lighthearted jab; they belie a secret to his success and longevity in life and business: don't be so serious. Behind his illustrious career as an investor, Munger and his renowned business partner Warren Buffett embraced a refreshingly simple and straightforward approach to investing and life. Living modestly and remaining intensely focused on continuous learning and growth, Munger embodied discipline and unwavering dedication. Yet, even in his pursuit of brilliance, he prioritized indulging in what he loved, even if it meant risking a few cavities. To borrow from another legendary thinker and creator, Charles Eames, he took his pleasures seriously. And after 99 years of brilliance and wisdom, Munger leaves us with plenty to chew on.  

Rec: Product, Tool, or Framework

▶︎ Cognitive Bias Codex

I’m a sucker for a good infographic, or any interesting visual representation of a complex idea. The Cognitive Bias Codex has been around for a while and often gets shared and referenced in articles by anyone thinking about… well, thinking. As much as I love simplicity and approachability of the design, the form itself isn’t the most exciting part about it. What interests me most is its function; a roadmap to understanding the way we think, live, and work. Looking to be a better communicator? It can help facilitate better awareness and communication. Learning to lead? Yep, it can help you better understand and motivate your team. No matter your interest, a bias will likely come into play. So, if life is about learning, then studying the biases serves to help you enhance your life.

Rec: Reading

▶︎ Seeking Wisdom or Poor Charlie’s Almanack

When I was fumbling through founding my first company, I was lucky enough to stumble upon both of these little gems—and they became my bible. As most know, founders face dozens (hundreds? thousands?) of decisions in rapid succession on a daily/weekly basis, and each decision can literally mean the life or death of your company. While the life of a company may sound a bit dramatic, when it has a real impact on your life and your family, those decisions feel particularly weighted. Hence, coping with the weight and depth of those decisions is a high-value skill critical to survival. So, in many ways, Munger’s books act as a survival guide; each offering detailed advice on investing, life, and decision-making. What I love most about Seeking Wisdom is that the checklists referenced throughout the book—and listed at the end—help you walk through decisions consistently and objectively. I loved them so much that I painfully copied each of them into a tool called TextExpander so I could reference them with just a few strokes of the keyboard, and improve my thinking in real time. Now, you may not need to go as far as I did with the checklists, but I’d definitely recommend you check out either of these books if you’re interested in becoming a better thinker and worker.

Rec: Watching

▶︎ The Psychology of Human Misjudgment

Munger saw life with a lot of clarity. He’s a thousand-yard stare in human form; focused, precise, resolute. In this talk, he breaks down what he calls “standard thinking errors,” or how humans misjudge the world. Many of these have been studied at length by some of the world’s best investors, entrepreneurs, and builders, and for good reason. Knowing what we don’t know is the first step to knowing anything.

Rec: Listening

▶︎ Acquired Podcast Interview with Charlie Munger

“Legend” isn’t a strong enough way to describe Charlie Munger—it cheapens his existence and legacy. Though his career was in finance, he garnered icon status with all modern thinkers for building and sharing wisdom across all industries, sectors, and experiences. As mentioned, beyond his wildly successful career with Berkshire Hathaway (and Warren Buffett), Munger was well-known for his takes on decision-making and thinking. And while he’s done many past interviews, according to Ben and David, this was his most extended podcast, coming in at right around an hour. For many, that sounds too long. But like everything Munger produces, it’s worth your time. It’s a helpful reminder with insights on how to frame your life, which can be incredibly helpful as we enter a new year. If you have any breaks or downtime over the upcoming holidays, I recommend listening to this podcast. But be sure to have a pen and paper to take notes—you’re going to need it.

And, just in case you missed it…

Here are some things that I’ve written and shared that people enjoyed that were influenced by Charlie Munger, either directly or indirectly.

Until Next Time!

That’s it for this week. As always, if you like the content, please do me a favor and hit the like button, share it with your friends, or drop in a comment — this newsletter runs on overpriced whiskey and reader engagement.

If you liked this post, I’d really appreciate it if you share it!

Share Path Nine

Thanks for reading, and see you soon,

Happy Thanksgiving to those of you in the US.

Throughout the year it can be easy to get swept away by the millions of little projects, decisions, and to-dos that fill our lives. For me, Thanksgiving is a helpful time to reflect on what—and who—is important in my life. In the spirit of giving thanks, I want to say ‘thank you’ to all of you who read and support P9. Your support motivates, encourages, and ignites.

Whether you’re home, abroad, or in-transit, I hope you find yourself surrounded by the people who enrich, inspire, and motivate you. And, while it can sometimes mean reflecting on those who aren’t with us anymore, it doesn’t mean we have to live without their impact.

Happy Thanksgiving,

Before we begin: If you’re reading this but haven’t joined the PATH NINE community, hit the button below to join creative entrepreneurs that read PATH NINE to learn the strategies reshaping our work and lives.

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It's difficult to fathom the pain outside our limited existence. We are the thinking, feeling, and suffering centers of our universe. Pain, pleasure, gratitude, pride, anxiety, fear, loneliness, regret; each constitutes the best and worst parts of being a human.

In times of struggle, it's helpful to remember that we all feel the same.

Recently, I lost a friend in a tragic accident. He wasn't a close friend, but proximate loss is a tragedy regardless of relationship. The loss—and my processing of it—forced me to evaluate what matters most to me and how I can live a life that honors my values. This isn't a tribute to our friend—he deserves much more than I can write about him. This is a reflection for those of us who wish to live and explore a life without regrets.

Losing anything can serve as a catalyst for change. I personally felt challenged to think critically about where and who I spend my time with. So I asked myself, "What experiences and activities can I do that I will never regret?"

The answer that's beaten into our heads over and over is that, on your deathbed, you'll never wish you'd worked more. But if regrets are simply answers to the question, "What did I want for myself that I didn't allow myself to have?" work might make the list. While there are clearly many things that should make the list, work shouldn't be exiled because that's what we're taught to think—that work is unimportant.

Who we are is a complex tapestry of seemingly innocuous acts that propel us through the universe. Work is a thread that weaves its way into the tapestry, adding color, complexity, nuance, and strength. Frequently, it's a mechanism for meaning and self-esteem. Like it or not, the thing you spend more than 50% of your life doing and focused on (i.e. work), is important.

In both work and life, we're faced with challenges. But worse still, we're handed invisible scripts that we're expected to follow mindlessly. These scripts come from our friends, parents, teachers, colleagues, neighbors— everyone and everywhere. Scripts that tell us to:

• take the well-paying job (even if you hate it)

• buy the house in the suburbs (even if you don’t want to)

• climb the corporate ladder (even if it destroys your family)

• have a few kids (even if you’re not meant to)

And on and on…

For some, they help usher us onto a path of prosperity; they lift, motivate, and encourage.

For others, they hold us back; they oppress, infuriate, and repress.

For my friend, and for many, work isn't the top priority. But I bet if asked, many people would say that work plays a significant role in their lives because it partially enshrines their legacy. Work contributes to self-worth because what we do is often conflated with who we are. While my friend may have regretted certain elements that centered around work, I suspect he wouldn't change it, for it gave him and his family the life they enjoyed together. It built a foundation for his energy. It made up or unlocked a part of him. He built a life not around work, but with work.

He owned a family business and ran it, in part, with the help of his family. Not only was he building a business, he was building a legacy, in his community, his family, and himself. His work was a part of him, not a means to an end. And this is where the confusion lies: in our ability and inability to find the genuine connection between work and living.

For me, work isn't just about laboring or making money; it's about doing something I won't regret. Writing this newsletter is work, but it's work I won't regret. While work may or may not fill the same space in your life — maybe it's your kids, your family, your hobbies, your pets — these things add up to the sum we all want: a life worth living.

Our work may not be the ultimate representation of our existence, but for many, it represents us in ways that are often indescribable: our ambition, energy, ideas, motivations, and legacy. It can open the door to new relationships. It can help you find balance and safety when things go wrong. And, if nothing else, it can be one way to live a life without regret.

Like Mr. Lewis, I won't presume your like is devoid of regret. No one should. Life isn't about living without regret; it's about minimizing the regrets that you have control over. Failure is not allowing yourself to experience the thin line between a well-lived life and a life without regret. A life well-lived inevitably leads to the potential for regret, but at the end of the day, it comes down to the type of regret you're willing to accept.

Here is a list of fifteen things that you won’t regret:

• Staying out too late laughing with close friends

• Dropping whatever you’re doing to help a friend in need

• Spending a little extra on the activities that bring you joy

• Sitting down to watch the sun set

• Holding the hand of someone you love

• Standing up to injustice or oppressive forces

• Pushing physical limits and doing just one more rep at the gym

• Taking five minutes to meditate and breathe

• Stopping to give extra cash or change to a person in need on the street

• Putting every ounce of energy you have into that project at work

• Sending a “just checking in” text to a friend or family member

• Saying “no” to another meeting or request for your time

• Waking up early to go for a sunrise walk/hike/ride/swim

• Taking that ‘once in a lifetime’ trip with people you love

• Taking a leap and betting on yourself

Like it or not, we're all faced with the realities of a finite existence. And while many details in our lives are unknowable and unchangeable, we're sometimes presented with opportunities to turn mundanity into miracles. Life simply cannot be lived without regret. Instead, the essence of life lies in minimizing regret by seizing opportunities, learning, growing, and embracing the depths that life has to offer. We have the power to make choices that we will never regret—and I hope, like me, you find a way to make that happen.

So, what is it that you should do?

What actions, experiences, and contributions will bring you everlasting fulfillment and leave behind a legacy?

Like me, you may find that your work and life endeavors answer the question, "What experiences and activities can I do that I will never regret?"

And if they don't, it's time to re-evaluate.

Until Next Time!

That’s it for this week. As always, if you like the content, please do me a favor and share it with your friends — this newsletter runs on overpriced whiskey and reader engagement.

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This week we’re kicking off the holidays with some weekly R&R (aka reflections and recommendations). No affiliate links or sponsorships here, just simple links to things I genuinely love and recommend.

My wife and I have been super busy globetrotting for both work and fun. We've hit up so many awesome places and had countless adventures. But all this traveling has left us feeling pretty drained and in dire need of some R&R. With a new year just around the corner, we’re eager to take a breather and recharge our batteries. In the next few weeks, I’ll dive into:

• 2023 annual reflections

• 2024 predictions and ideas to consider

• creative inspiration, tools, and ideas for 2024

Alrighty, without wasting any more time, here are a few amazing things that will totally up your thinking, working, and living game.

Have an awesome week ahead!

Before we begin: If you’re reading this but haven’t joined the PATH NINE community, hit the button below to join creative entrepreneurs that read PATH NINE to learn the strategies reshaping our work and lives.

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Reflections

▶︎ What season of personal development are you in?

For years, people have talked about the 'seasons of life' and how we should metaphorically frame our lives around the natural cycles and weather patterns. And that's a great way to look at life, what does it mean for your productivity and creative growth? To truly understand the concept of 'seasons of life' and its implications for personal growth, we must consider how our development stages evolve over time. While youth is marked by rapid growth, adulthood often brings a state of comfort and stability. However, we must acknowledge that the world around us is constantly changing. To foster continued growth and evolution, we must actively seek new challenges, embrace change, and cultivate a mindset of lifelong learning. By doing so, we can navigate the ever-changing landscape and ensure our personal growth remains vibrant and relevant throughout our lives. I’ve been trying to embody this mantra in my daily practices, but I’m curious: “how do you think about personal growth and development phases?” Share your personal growth philosophy in the comments.

Rec: Product, Tool, or Framework

▶︎ Karst Stone Paper Products

I love a good, high-quality notebook. Almost as much as I love a good, high-quality pen or pencil. After spending years obsessing over design, the combination of a well-designed tool and the utility it provides in the act of creation is deeply attractive to me. Part of the attraction stems from a tool's ability to reshape our thinking, and therefore our creation. Like putting on a nice suit for work, a beautiful, albeit utilitarian tool can help us embody a certain level of calm confidence. That’s why I really enjoy the refreshing twist Karst Stone Paper Products puts on a well-designed and sustainable product for creatives. Their Daily Planner Set enriches my morning meditative practice by providing an offline outlet to think critically about my priorities. It's a beautiful, sustainable, and mindful addition to the mundanity of our digital routine.

Rec: Reading

▶︎ Die With Zero: Getting All You Can from Your Money and Your Life by Bill Perkins

I'm not reviewing this book, but maybe I will in the future. I put off reading it for a few months, primarily because the premise just seemed too simple. If you know anything about the publishing industry's economics (and incentives), you’ll know that most traditionally published books turn a tweet-sized idea into a "War and Peace"-sized novel. But in spite of my reservations, I decided to read "Die With Zero"—and I’m glad I did. It wasn't revolutionary, but it was a friendly reminder that money is a tool. And like any tool, it should be used for the right job and at the right time. Whether you’re building a war chest or planning to save all of your money in order to give it to charity when you die, when we use our money can be just as important as how we use it. Don’t waste your life—and your money—waiting for tomorrow. Make the most of what you have, when you have time to enjoy it.

Rec: Watching

▶︎ Radiohead’s - In Rainbows From the Basement (April 2008)

I've listened to and watched this live performance a half-dozen times. Each time, I plan to just play it in the background, but end up completely transfixed by the exceptional performance. As a longtime fan of Radiohead, I greatly appreciate their ability to transform dissonant ideas into mesmerizing melodies. When watching this performance, it feels like the culmination of their life’s work—the pièce de résistance in a long, fruitful career as a band. A true lesson in mastery and coordination. But they didn’t just arrive here. What makes In Rainbows so special is the timing. Arriving as their 7th studio album, it highlights the thematic change in creative and personal development seasons between their previous albums and In Rainbows. The performance serves as a reminder: mastery looks easy, but takes years of hard work, patience, and dedication—so be patient.

Rec: Listening

▶︎ Dissect “In Rainbows”

If you couldn’t tell, Radiohead is a consistent soundtrack in my household. And from what I can tell, that’s also true for legendary music podcasting figure, Cole Cuchna. As the founder and host of the immensely successful show, Dissect, he has gained a reputation for his insightful analysis of talented artists and their albums. In previous seasons, Cuchna delved into the works of remarkable musicians such as Frank Ocean, Kendrick Lamar, Kanye West, Beyoncé, and many others. Currently, he has embarked on a deep exploration of one of my personal all-time favorite albums, "In Rainbows" by Radiohead. For music enthusiasts and musicians alike, his podcast is an incredibly compelling listen that offers valuable insights into the method behind the madness of the music — how the sausage is made, as it were. I highly recommend checking it out.

And, just in case you missed it…

Here are some things that I’ve written and shared that people enjoyed.

Until Next Time!

That’s it for this week. As always, if you like the content, please do me a favor and share it with your friends — this newsletter runs on overpriced whiskey and reader engagement.

If you liked this post, I’d really appreciate it if you share it!

Share Path Nine

Thanks for reading, and see you soon,