I Got Headhunted to Lead Engineering at a Megaventure. I Lost the Bet.

In my late 30s, I was riding pretty high.

A megaventure called me about running the engineering side of a new business launch — a classic headhunting situation.

The title: Head of Engineering.

My salary jumped considerably, and from the outside, it looked like “you’ve basically peaked, career-wise, no?”

At the time, I probably believed that too.

But life is unpredictable

A competitor running almost the same business model went on to succeed cleanly. They’re still around today as a massive service.

Ours, on the other hand, didn’t take off.

If you start dissecting the reasons in detail, the list never ends. Strategy, timing, funding, organization, internal relationships, market dynamics.

And honestly, my own lack of skill played a role too.

In the end, I left the company.

Or to put it bluntly: I got shown the door.

After I left, the company itself went bankrupt.

Then the CEO got arrested for stock manipulation.

“Is this a TV drama?” I thought.

That period was honestly tough mentally. “What exactly was I betting on?”

Looking back now, ventures genuinely are a gamble.

Of course you need effort. Technical skill matters. Strategy matters.

But in the end, too much of it is outside your control.

Leadership can go off the rails. A single cash flow event can blow everything up.

No matter how hard the team on the ground pushes, sometimes nothing helps.

I was on the losing side of that bet.

That said, it’s not like life ended there.

Life today isn’t bad.

I work as a freelancer with reasonable freedom, still doing technical work.

But sometimes I think.

“What if that business had succeeded?” “What if I’d stayed on the executive track?”

Thinking about it doesn’t change anything — but I’m human, so occasionally I do.

…after writing all that, the conclusion is — there really isn’t one.

Ventures are a gamble. I lost. That’s it. It was interesting, looking back. Honestly.

That’s fine.

The business card from those days that says “Head of Engineering” is still in my desk drawer. I find it now and then and laugh — “I was so young.”

I don’t actively want to throw it out, but I’m not about to show it to anyone either.

The company is gone. The title is gone. But the technical skills I picked up back then I still use pretty normally today.

The things you chase hard for don’t always last as long as the things you happened to pick up along the way.

Life, I think, kind of works like that.

So — sitting somewhere in that half-finished feeling, I’m just casually working away these days.