Field Notes
Twenty Years In
Dan Hebert · September 12, 2026
Two jobs, same story
Before the healthcare software company, I spent over seven years at a manufacturer in the automotive supply chain. We were rewriting the systems for an entire plant. I had a project manager, another engineer, a junior engineer. A real team.
Then 2008 happened. The automotive industry took a dive, and the people who make parts for cars took it harder than the people who make cars. I kept my job. I lost everyone else. I stayed another four years, alone, building out the rest of the plant.
Then I moved to the software company, and within a couple of years the same thing happened. The team shrank until it was me, working in my own corner, the only person who knew how the application worked.
Put the two together: of the last thirteen years or so, most of it I spent in a silo.
What a silo does to you
Here's what nobody tells you about working alone for a long time. You keep getting better at the job you have. You just stop getting better at the job.
I switched from VB.NET to C# in that stretch, and later from ASP.NET to Node and React. I could jump between languages and platforms without much trouble. I thought of myself as someone who kept current. And in a narrow sense, I did.
But I never saw anyone else's code. Nobody reviewed mine. Our stack was on-prem, Docker, and Subversion. No git. No cloud. There was no one around to say "we don't do it that way anymore," because there was no one around.
So I kept using patterns I'd worked out on my own, without knowing the industry had names for them. I kept writing code that worked, without knowing it wasn't code a team could live in. I wasn't lazy about it. There was just nobody to compare against.
Why you can't feel it
Isolation doesn't feel like damage while it's happening. It feels like being trusted.
You're shipping. You're the person who knows how everything works. When something breaks at 2 a.m., they call you, and you fix it. Every signal you get from the inside says you're valuable. And you are.
It even protects you. When the layoffs come around, and they come around more than once, you're the one they can't let go, because nobody else knows how the thing works. I survived round after round that way. It felt like security. It was the silo getting deeper.
The damage only shows up when someone from the outside asks you a question and you can't answer it. Not because you don't know the thing. Because you've never had to say it out loud to a stranger.
If you're twenty years in
If you've been at one place a long time, and you're good at it, and the team around you has thinned out over the years, this is worth taking seriously before you need to. Not because your skills are gone. Because your vocabulary might be, and interviews are conducted in vocabulary.
I found this out the hard way, two years into a search. Next post: what I did about it.
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