I never changed careers, only systems | Silvestri DOT Cloud

I never changed careers, only systems

Jul 9, 2026

min read

What a bass guitar, a Commodore 64, and a mixing desk taught me about becoming a CTO.

A few weeks ago I was cleaning up my Google Drive, which is the digital equivalent of finally opening that one drawer everyone has at home - the one with cables for devices you no longer own, warranties for things that died years ago, and a mysterious key you will never, under any circumstances, throw away, because what if, someday, against all statistical probability, it turns out to open something important?

Buried between old invoices and long-forgotten projects was a PDF called post-production_contract.pdf, and because I am constitutionally incapable of leaving a mystery unopened (this, incidentally, will become a running theme), I clicked on it.

Four pages. Formal language. Deliverables, payment schedules, governing law, and - I want you to sit with this - a royalty clause so ambitious that present-day me would read it, laugh once, and then quietly delete the file out of secondhand embarrassment. Except I didn’t delete it. I read the whole thing, because at the top of the first page, in big bold letters, was a title I hadn’t used in years:

Marco Silvestri – Producer.

I smiled. Partly because I had genuinely forgotten I’d ever branded myself like that, partly because I immediately started mentally correcting my own English from six-years-ago (some habits never leave), and partly because I realized this document belonged to someone who, at least on paper, doesn’t seem to have all that much in common with the person writing this post today. Back then I was living in Nairobi, spending my days recording bands, mixing songs, mastering albums, and teaching music production to aspiring engineers who were, in retrospect, probably as confused as I was. I distinctly remember once negotiating over a discount of one thousand Kenyan shillings (which was roughly the price of two mediocre pizzas!) with the kind of grim determination usually reserved for hostage negotiations. At the time it felt like a battle worth fighting. Today it’s just a story I tell at dinner parties to watch people’s faces do that polite-but-confused thing.

When people ask me about my career, that’s usually where chapter one ends: “and then I left music and became a software engineer.” It’s a perfectly reasonable summary. I just don’t think it’s true anymore, and I’m going to spend the rest of this post trying to convince you of that, so buckle up. This is not going to be a “10 Lessons I Learned Becoming a CTO” post, mostly because I don’t trust anyone, including myself, who can compress a career into a numbered list with a LinkedIn-friendly hook. Life doesn’t ship with bullet points . It ships with a four-page contract you forgot existed and a title that made you smile for reasons you didn’t fully understand until you sat down to write about it.

Here’s a piece of trivia that will do a lot of unearned work later in this post: my childhood babysitter wasn’t a person. It was a third-hand Commodore 64. If you’re old enough, you already know exactly what I mean - the several minutes spent waiting for a game to load off a cassette tape, only for it to fail at 98% and force you to start the whole ritual over, which I now realize was basically an early, unpaid course in resilience engineering. If you’re not old enough, I genuinely don’t know how to explain the specific flavor of despair involved, so just trust me.

The strange thing is that, despite having a computer practically raising me, I did not become a programmer.

Not even close.

Not because I wasn’t interested in technology - I just didn’t know yet that the thing I was interested in had a name. I, instead, picked up a bass. I learned how microphones worked, then became weirdly, obsessively fascinated by compressors and equalizers and the invisible plumbing of a signal chain - the sort of thing nobody at a date wants you to explain to them, and yet I did, repeatedly, to anyone who made the mistake of asking what I “did.” Eventually I ended up teaching those subjects professionally, which felt, at the time, like the whole story.

Then, in what still feels like an absurd plot twist someone else wrote for me, I re-discovered web development. And here’s the genuinely embarrassing part: in 2020 I barely understood how a website worked. Reverse proxies? No idea. Virtualization? Just dabbled in that. Containers? Something ships arrive in, surely. If you’d told me that six years later I’d be spending my evenings happily arguing with myself about storage architectures, monitoring pipelines, and backup strategies, I would have politely suggested you turn down the reverb on your headphones, because clearly...