Wrong About Success | The Founder Edit

At 25 — what did I think my life would look like at 40?

Let me tell you what I thought.

At 25, I was a complete wreck. Fresh graduate, straight into the subprime crisis. My friends couldn’t find jobs. Somehow I got one instantly, and I thought: maybe God’s favour is with me.

Then I actually started the job.

I spent three months writing a property initiation report. My boss tore it up in front of me. Who does that to a fresh graduate? I quit in four months and told myself: it’s the boss. New job, new environment — surely that changes everything.

A year and a half later, I finally admitted it. Maybe it’s not the boss. Maybe it’s me.

So I did the logical thing. I went into acting.

Here’s what I actually thought success looked like at 25: getting married. Having kids. I was young, not bad looking, there were a lot of guys — and I genuinely believed I could get the ticket. The rich husband ticket.

I wasn’t dreaming small, either. I was dating the 1%. One boyfriend’s father was seriously wealthy. The net worth in my head was in the billions. Not mine, of course. Ours.

At 25, I thought it was going to be easy.

I surely didn’t think that one day, I’d have to be my own husband. My own provider.

At 30, I changed religions — from marrying it to building it. Forget the guys. I’m starting my own business. And my math was simple: if so-and-so can start a company and exit at 20 million in five years, so can I. I wasn’t even being greedy. I didn’t need a billion-dollar valuation. I was happy at twenty, thirty million.

That was ten years ago.

Who knew.

So here’s the honest audit at 40.

What part of my life makes me feel like I haven’t made it? Everything. I drive a crap car. I live in a tiny house. I’ve aged, I’ve gained weight, I ache all over. No exit. No billions. No rich husband — not even a husband.

If this is what every 40-year-old feels like, then 40-year-olds suck.

And what am I secretly proud of?

I sat with that question a long time, because my first answer was: nothing. I’m very good at being critical of myself.

But there is one thing. I have humbled myself beyond what I could ever imagine.

The girl who thought she’d marry billions learned to be her own provider. The girl who planned a 20-million exit in five years is still here in year ten. Still standing. Still building. Still learning.

At 25, I thought success would marry me. At 30, I thought I’d buy it. At 40, I’m finally asking what it actually is.

This season is me finding out.

This is part of The Founder Edit — a season called The Things I Was Wrong About. One honest essay at a time. Start here.