Reflections, Plateaus, and Fresh Starts
Unvarnished contemplation amidst a year of turmoil
Welcome back, friends.
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.
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:
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.