The Eric Wroolie Blog

I fired my last human developer about a year ago. That sounds worse than it was. It wasn’t dramatic. There was no argument, no falling out. It just… ended. The way these things do.

And now my entire development team is AI.

I’ve been running Overpass for over twenty years. In that time, I’ve hired and let go of more developers than I can count. I’ve had brilliant designers who disappeared for weeks. I’ve had coders who turned out to be juggling five “full-time” jobs under different names. I’ve sat in screen-share sessions doing in an hour what someone spent a week failing to do. I’ve lost sleep over payroll. I’ve wondered, more times than I’d like to admit, whether I was the problem.

Maybe I was. Maybe I’m not easy to work with. I know I’m not easy to be friends with — my kids remind me of that regularly.

But here’s what I keep coming back to: for twenty years, the hardest part of running Overpass was never the code. It was the people. And I don’t mean that in a cold way. I mean it in the way that anyone who has managed remote teams across time zones knows — the trust, the communication gaps, the hoping someone is actually working when they say they are. The wanting to just do it yourself because you know you can do it faster.

I wrote about that years ago. Delegating and giving up control. I compared it to sitting in the passenger seat while my teenager learned to drive. Terrified. Wanting to grab the wheel.

Well… I grabbed the wheel. I just replaced the passenger.

I’ll be honest — when I first started using AI to code, I felt like a fraud. Again. Here I am, a developer with decades of experience, asking a machine to write my code. What does that make me? A developer? A manager? A guy who talks to robots?

But then I realised something. I’ve always been the guy who figured out how to get things done with whatever tools were available. When I was in the Army, I learned Mandarin — not because I had some natural gift for languages but because it was the path in front of me and I took it. When I got into IT, I didn’t have 12 years of experience like the junior developer assumed. I had two years of C# and a lot of confidence that I could figure it out. When I started making apps, I was starting from scratch. Again.

This is just the next version of that.

The funny thing is, my AI developers don’t go missing for a week. They don’t have five other jobs. They don’t need me to motivate them or chase them on Slack at odd hours. They just… work. And when they get something wrong, I fix it and move on. No awkward conversation. No guilt.

I miss some of it, though. I miss the camaraderie. I miss the trip to the Philippines with my team where we sat at a resort and talked about the future of the company. I miss having someone to bounce ideas off who could push back and say “Eric, that’s a terrible idea.” AI doesn’t do that. It’s very agreeable. Sometimes too agreeable.

There’s a loneliness to it that I didn’t expect. But then again, I’ve always been comfortable with loneliness. I used to go to the cinema by myself as a kid. I sit in cafés by myself now. I’ve built most of this company in rooms where I was the only person.

Maybe this was always where I was heading.

I get messages from other developers — usually the ones who watch the YouTube channel — asking me if AI is going to take their jobs. I understand the fear. I really do. But I think the question is wrong. The question isn’t whether AI will replace developers. It’s whether you can learn to work with it before someone else does. It’s the same thing I’ve been saying for years about technology skills being like currency. The value of what you know today is always dropping. You either learn the new currency or you go broke.

I’m 53. I’ve reinvented myself more times than I can count. Factory worker. Soldier. Linguist. Teacher. Banker. Developer. YouTuber. Stand-up comic. And now… whatever this is. A guy who runs a company where his entire team lives inside a terminal.

It sounds ridiculous when I write it down.

But so did everything else, at first.

“Are you one of the comics?” I was asked last Tuesday at my second-ever gig. It was at First Laughs in Cambridge.

Well, you could call it my first gig.  It was my first real one. One where I booked it myself.  One where I was alone with no friends (either as comics or in the audience).  I was putting myself out there.  

And our good old friend Imposter Syndrome paid a visit.

“Yes, I’m one of the comics.”

I’m 51, and I can still feel like an imposter.

I’ve made so many videos about imposter syndrome in the past, and every time, it resonates with people. They will leave comments or sometimes email me to say they feel this, too.   It’s as if we are kindred spirits with an affliction.  But I think everyone has this.  Or, at least, they should.

I’m a strong believer that if you don’t feel like a fraud once in a while, you aren’t pushing yourself hard enough.  You’ve become complacent. You’ve gotten soft.  You’ve unpacked your bags and settled into your comfort zone.  

We all do this from time to time.  We wake up and realise we are in a rut.  Or that life has lost its magic, and we need to do something to bring it back.

We have to embrace uncertainty.

To quote Gary John Bishop from his book “Unf*ck Yourself”, “Uncertainty is where new happens.”  I read that book last night.  It’s pretty good.

Yeah, we need to venture out into uncertainty sometimes. 

But that doesn’t make it easy.

It’s so much easier to say and put that quote on Instagram than it actually is to actually do it.

Do the things that terrify you.  Standing in front of a group of people (there were 30 at this gig, 250 at the last one) and telling jokes you hope they agree are funny… terrifies me.  What better reason to do it?

The gig went well.  A few people came up after and told me how much they enjoyed it.  

I kept focusing on a joke I left out— I totally skipped it. Accidentally. But no one would have noticed. It was one of my favourites.

When I released my first app, and no one downloaded it, I was disappointed. But I knew I was a beginner. It was either quit or accept that I sucked at it so I could improve.  I did.

It was the same when the first videos I did weren’t watched by anyone.  I persisted.

And it will be the same with this.  I loved people saying nice things to me.  I have a lot to improve on.  

But it was awesome. What a rush!  

My next gig is this Thursday.

I absolutely love this.