“Can you spot me some cash for lunch?” Alex texts me from the other room.

“Yeah” I reply.

I’m a little tense. The fact that I always have money to lend is starting to look suspicious.

It’s January 2010. We’re employees at a small tech firm. Alex is the CTO, and I lead the design team.

Today we’re going to the pancake place.

The business hasn’t been doing well. We’re still not profitable. The funding we raised two years earlier has run out. Everyone in the company has taken a pay cut, and salaries are often delayed, including mine.

But I've got a little secret. I’ve been doing side gigs since last summer. And I’ve been thinking about quitting and going fully freelance for a while.

I have two clients paying hourly at the end of each month.

It’s shaky. They’re self-funded startups with no revenue.

And frankly, questionable business ideas.

Combined, they pay about as much as my salary, but I only work a few extra hours a day.

Safe enough to quit? Hell no.

No marketing, no visibility, no idea how to sell my work.

No YouTube gurus to learn from.

Damn, I don’t even know what marketing is and how to do it.

Instagram hasn’t launched yet. LinkedIn is a resume platform.

Those two clients could disappear any day. Should I do this or am I an idiot?

April 2010

Monday, 9 a.m. Cold and sunny.

I’m in a traffic jam, driving to the DIY store. I need a new sink strainer.

The store is next to my parents’ house, so I drop in for tea with Mom. Dad’s at work.

We take our time, sip tea, and talk. It’s the first Monday in ten years that I don’t have a job. I’m on my own, I’m 26, I’m a bit lost, and I like it.

November 2025

All this time, I somehow managed to make a living on my own.

That feeling still visits me at times: lost but free, free but lost.

But I guess it’s how it works.

I’ve met hundreds of founders over the years.

Those starting out, those who’ve built something big, and those who’ve lost it all and started anew.

They feel it too. That mix of fear and freedom never goes away.

Somehow, it all works out.