Why most people never start

A letter to anyone considering starting something

Kevin Kirkpatrick

Mar 18, 2026

Welcome back, friends.

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.” - Anu, Working Theorys

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.

Woman walking near the gate photo – Free Black Image on Unsplash

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.

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.