The hard truth I will not ignore

Being intent-driven is now central to my story

💡 On this Substack I’ll write a lot about intent-driven development and the massive changes GenAI is bringing to authoring software. But first I wanted to share a personal story about intentionality.

---

I’ve long clung to a comforting lie: my career was accidental.

Success? Just a series of lucky breaks. A view that has shaped me for decades.

I grew up with privileges that I didn’t fully recognize.  At eight, I had a computer to tinker with—a rarity in the ’80s. I could touch type before I could write cursive. 

Each accomplishment in my life has felt like a happy accident.

I joined the cross-country team because I wasn't good enough at soccer. Yet somehow, our team won three state championships.

Never mind the pre-dawn runs, the blisters, the moments I pushed through when my lungs were on fire.

Easier to call it luck than acknowledge the work.

And then I made it through college, graduated with honors, landed an amazing job—all luck.

This mindset became my shield, my armor against my terrifying vulnerability of wanting something but failing to get it. If success was just luck, failure couldn't really hurt me.

But now I’m starting to see what I’ve had trouble admitting: success isn’t accidental.

Looking ahead may seem daunting because we fear failure, but looking back, the hard work and small decisions that shape us are easy to gloss over in a simplified narrative of luck.

For me, that narrative first started to shift with my choice to build products for software developers. Joining DigitalOcean was no accident. It was an intentional step towards a personal mission to help people realize they could build anything they want.

But old patterns die hard, and after a while I again started attributing successes to luck, leaving room for any failures to be accidents.

In May of this year, when I started to go deeper with AI assisted development tools, I was forced to confront this narrative head on. Accidents won’t get me where we’re going next. Even before software composition had a name and before Cursor’s release of the eponymous composer functionality, I could see clearly that the way we build software is forever changed.

From that moment, I couldn’t unsee it and every job opportunity that came my way felt rooted in the “traditional” way of developing software. I realized that I needed to start something new and intentional.

This realization was both terrifying and liberating. The thing I’ve feared for so long—setting clear goals and owning my choices— planted the seed for SpecStory.

A company not born out of luck, but deliberate choice, even if I could fail; hell maybe because I could fail!

With hindsight, the same skills that made me successful in my career as an "accidental technologist"—adaptability, curiosity, technical aptitude—were actually carefully cultivated traits.

My journey to intentional founder hasn't been linear. Some days, I still catch myself defaulting to that old narrative of luck. The path still twists and winds. I'm far from reaching its end.

But our stories are about more than where we end up— they’re about how we choose to get there.

What I now know: the eight-year-old me, typing away at that first computer, wasn’t just lucky.

He was building something.

He was building this. He was building me.