Your Definition of Success Is Too Narrow

I’m thirty-one.

I live in my favourite place in the world. I own a home here. I have a wife I’d choose again every single day, three beautiful kids, a stable remote job, a community that actually shows up for each other, and hobbies I care about deeply.

By most reasonable measures, I have it all.

And yet for years I was convinced that none of it would count unless I also built a venture-scale startup.

That’s a strange thing to admit. But I think a lot of people carry a version of it. Some unspoken benchmark they set for themselves at twenty-two that quietly poisons the life they’ve actually built.

I want to talk about how I let go of mine. And about a framework that helped me see what was really happening.

Imagine where you’re standing right now as a single point.

Behind you is the path that got you here. A mixture of decisions you made, chances you took, people you met, and luck you didn’t earn. Some of it was skill. Some of it was timing. Most of it was both at once.

Now look forward.

In front of you is a cone of possibilities. Every future you could plausibly reach from where you’re standing. The cone radiates outward, and how wide it opens is, to a meaningful degree, up to you.

During my GearShare years, I had squeezed that cone down to a pinhole.

I’d decided that building a venture-scale marketplace was the only way I was going to create wealth. The only way to prove I had the work ethic, the intelligence, the grit. The only way to build a legacy for my family. The only way to travel the world on my own terms.

One path. One proof.

I called it focus.

It was fear.

This is what it looked like in practice.

I spent two years perfecting every detail of a product I hadn’t shown to a single person. I built production-grade analytics before I had a staging URL. I chose the hardest possible road because anything easier felt like settling.

I wasn’t building a business. I was building the version of myself that I thought I needed to become. The startup was the vehicle for an identity, not a market problem.

And the narrower the cone got, the more certain I felt. That’s the trap. Narrow feels like conviction. It feels like clarity. You mistake the absence of options for the presence of purpose.

Rand wrote about this, though I didn’t recognise it at the time. She warned against letting your subconscious accumulate “a junk heap of unwarranted conclusions, false generalisations, undefined contradictions... fused into a single, solid weight: self-doubt, like a ball and chain in the place where your mind’s wings should have grown.”

That’s what the narrow cone was. Not a philosophy I’d chosen through “conscious, rational, disciplined” thought. It was an unexamined set of assumptions about what success had to look like, what I had to prove, and who I had to become. I’d mistaken those assumptions for conviction. They were just inherited fears I’d never interrogated.

If you’ve ever been so locked into a single goal that every other part of your life started bending around it, you know this feeling. It’s intoxicating. And it’s a delusion.

Two things happened at once.

My wife and I found out we were expecting twins. And I finally let myself look honestly at GearShare.

The maths didn’t work anymore. Not the business maths. The life maths.

A marketplace that needs all-in commitment, significant capital, and years of patience versus a family that needs stability, presence, and a father who isn’t consumed by runway anxiety.

The honest calculation took five minutes once I stopped negotiating with myself.

But the grief took months.

Because I wasn’t just closing a startup. I was closing the only future I’d allowed myself to imagine. The cone had been so narrow that when I collapsed it, there was nothing else there.

That emptiness was the signal.

Here’s what nobody tells you about letting go of a fixation.

The world doesn’t shrink. It expands.

Once I stopped telling myself that venture-scale startup was the only valid path, I could suddenly see dozens of paths I’d been ignoring.

Property investment. Bootstrapped side projects. Finding the right role at a company that actually aligns with how I think. Going deep on community. Writing here on Substack and seeing how far that could go. Combining consulting with building tools that solve real problems I encounter at work.

None of these are lesser paths. I’d just been too narrow to see them.

The cone widened. And for the first time in years, I could breathe.

This isn’t just my story. Everyone has a cone.

Right now, wherever you’re standing, there’s a range of futures available to you. Some are obvious. Some you haven’t considered. Some you’ve actively blocked because they don’t fit the narrative you’ve built about who you’re supposed to become.

Three questions worth sitting with.

How wide is your cone right now?

If you can only imagine one version of a successful future, your cone is probably too narrow. That’s not conviction. That’s fragility. One setback and the whole thing collapses because you’ve left yourself no other version of “winning.”

What are you refusing to see?

There are paths inside your cone that you’ve dismissed. Not because they wouldn’t work, but because they don’t match the story you’ve been telling yourself. The corporate path that feels like “giving up.” The creative pursuit that feels “unserious.” The simpler life that feels like “settling.”

Challenge those dismissals. They’re usually ego, not strategy.

What values are you actually optimising for?

A wide cone without direction is just indecision. The cone gives you range. Your values give you aim.

My core values are growth and courage. Everything else I care about stems from those two.

Growth means I need to be learning. Always. If a path doesn’t stretch me, it’s the wrong path regardless of how comfortable it looks. Courage means I have to be honest about what I actually want, not what I think I’m supposed to want, and then move toward it even when the outcome isn’t guaranteed.

Presence with my family, building things that teach me something, financial stability that lets me take calculated risks, work that feels like expression rather than compensation. All of those are downstream of growth and courage. They’re the shape those values take in the life I actually live.

Those values don’t point to one path. They point to many. And any path aligned with them has a real shot at working.

That’s the point. The width of the cone is freedom. The values are the compass inside it.

Here’s the part I’m still making sense of.

I got everything I wanted. Just not the way I expected.

At twenty-two, I assumed that by thirty I’d have some visible marker of “career success.” A company. A title. A number. Something I could point to and say, that’s proof.

I don’t have that.

What I have instead is the product of hundreds of smaller, value-aligned decisions made over a decade. Moving to a town I love. Marrying someone who makes me better. Saying yes to consulting work that stretched me. Saying no to things that didn’t fit. Building skills across domains instead of going deep in one. Keeping the cone wide enough that when the right things arrived, I was positioned to receive them.

None of it looked like the plan.

All of it added up to more than the plan ever promised.

That’s the paradox. The narrow cone felt like the path to success. But the wide cone, guided by values, is what actually built the life.

I’m not deterministic about this. And I’m not on the other end either.

You can’t manifest your way into a specific outcome. But life isn’t pure randomness. It’s closer to a feedback loop. You make decisions. Life responds. You adjust. Some choices create options you couldn’t have foreseen. Some close doors you’ll never know about.

The point isn’t to control what comes next. The point is to keep the cone wide enough that when life responds, you’re positioned to move. That takes courage. It’s easier to cling to one path than to hold the uncertainty of many.

Some of the best things in my life, this town, this community, these friendships, my wife, arrived sideways. Not because I chased them, but because I was open enough to notice them and brave enough to say yes.

I don’t know which path I’ll take next.

And for the first time, that doesn’t scare me.

Property. Bootstrapped products. Writing. Consulting. Some combination I haven’t thought of yet. The cone is wide. The values are clear. The life is already good.

The old version of me would have found this uncertainty unbearable. He needed the narrow cone because he needed the certainty that came with it. Even if that certainty was a fiction.

This version of me sees the width as the asset.

Not because more options means more success. But because a wide cone, honestly examined and guided by values that actually belong to you, is more resilient than any single bet.

If you’re reading this and you’re locked into one definition of success, one path, one proof, ask yourself whether that’s conviction or whether it’s fear.

Conviction survives scrutiny. You can poke at it and it holds.

Fear disguised as focus falls apart when you ask simple questions. What if this doesn’t work? What else could I do? What am I refusing to consider?

If those questions terrify you, your cone might be too narrow.

Widen it.

Not to avoid commitment. But to make sure the thing you commit to is actually yours, chosen from courage rather than clung to from scarcity.

Your values will aim you.

The width just gives you room to find the right direction.