On November 3rd, I announced I had joined Hookdeck to lead Outpost. It looked like the perfect setup on paper: a founder-like role, a smart team, and a problem space (EDA) that I’ve spent the last 12 years mastering.
On November 24th, exactly three weeks later, I resigned.
I’ve spent the last month processing this. I’m sharing the story not because I like talking about my mistakes, but because I bet a lot of you are stuck in the exact same trap I fell into.
I spent over a decade in the internet’s boiler room. I built AsyncAPI. I worked on protocols, specs, and plumbing. I became an expert in the pipes that run the web.
When the Hookdeck opportunity showed up, I said “Yes” because it felt like the logical next step. I knew I could do the job. I knew I could be excellent at it.
But within days, I realized I had confused my Zone of Excellence with my Zone of Genius.
Zone of Excellence: Things you are incredibly good at, but they drain your energy.
Zone of Genius: Things you are naturally drawn to, and they actually give you energy.
4 zones of work — by Sydney Chamberlain (sydneychamberlain.com)
I was hiring myself out to build infrastructure plumbing just because I was good at it, not because I loved it. I tried to force an obsession with retry logic and delivery guarantees, but my heart just wasn’t in it.
I actually considered staying until we shipped the first stable version of Outpost. But let’s be honest, that was just me being a coward. I was simply trying to avoid a tough conversation with Alex.
And that’s not fair to them. They are a lovely team, and I really wish I had met them earlier in my life. Alex handled the news incredibly well, and I only have good words for them.
Hookdeck is an incredible company. They are currently in growth mode. They deserve a leader who thrives on that intensity and wants to be hands-on in the engine room, obsessing over every challenge.
I realized that staying wouldn’t help them. I would be blocking a seat that belongs to someone who wakes up every morning hungry to solve those specific technical problems.
I respected the team too much to fake it for a year, vest some equity, and pretend to be the leader they needed. So, I decided to fix the mistake early.
Leaving that role gave me the instant clarity I was missing.
I don’t want to build pipes anymore. I want to build for humans.
I missed the messy, emotional, creative side of software. I want to build tools for creators, writers, and communities. People who use software to express themselves, not just to route data.
So, for the last month, I’ve been going all-in on Commune, the headless Substack alternative I’m building (more on that next week 😉). For the first time in a long time, the work doesn’t feel like work.
A Reality Check in Paris
From December 8th to the 12th, I was in Paris for the Apidays conference (now FOST — Future of Software Technologies).
I didn’t go for the content. I went to hang out with friends. It’s hard to get everyone in a single place, so conferences make that easier. Plus, Paris in December seemed perfect.
But the vibe hit me hard. I was shocked by how many people are terrified of losing their jobs, struggling to find new ones, or just flat-out hating the work they do. It wasn’t just a few people, it was a lot of them.
The feeling I got was completely unexpected. I even had a co-founder of a company offer to join Commune as a founding engineer. WTF?
This trip really hammered home my decision to leave Hookdeck. It made me realize the massive privilege I have right now. I have the freedom to choose, to quit, to build my own life. A lot of people just can’t do that right now, or simply can’t see the path.
If you are sitting in a job right now because it is “safe”, the pay is great, or simply because you are good at it, but you feel bored or drained, pay attention to that feeling.
I know not everyone is in a position to just walk away. Bills are real and we all have responsibilities. But if you have the privilege to afford it, or if you can apply for a job that actually lights you up, don’t wait.
It is way better to endure 15 minutes of awkwardness by quitting early than to endure 15 months of mediocrity by staying too long.
Let’s go build something we love.
This week, I want to shine a spotlight on a newsletter: Start Data Engineering. If our conversations about Event-Driven Architecture resonate with you, I think you'll love their approach.
Start Data Engineering
Bringing software engineering best practices to data engineering.
Over the last decade, I've built highly scalable distributed data platforms and helped companies scale to processing multiple exabytes of data.
My mission is to bring software practices followed by top tech companies to data engineering and help data engineers level up.
I help data engineers land high paying tech jobs and significantly up skill themselves.
