Field Notes
Stale to Standout
Dan Hebert · September 6, 2026
"Good luck to you."
That's how my job search started. Not with a layoff. With a sentence.
I'd been at the same healthcare software company for about six years. Over four of those years I'd gotten a total of one raise: two percent. The company wasn't doing well, and then COVID hit, and it got worse.
During COVID, I was in the middle of rewriting one of our main products. The director had decided everything we'd built in ASP.NET had to become React, with Node on the back end instead of C#. No component libraries. No TypeScript. Pure vanilla. For training, they gave us a thirty-minute video.
Then the team disappeared. The other developer was junior and mostly did support. The support person went out on medical leave. The project manager's pay got cut and she left. Six months in, it was me and a nurse who was new and handling the customer. For about two years I carried that rewrite alone, during a pandemic, for no extra pay.
It shipped. The contract was a success.
So I went to the VP of Engineering and made the case: we were something like twenty percent below market for entry-level engineers, never mind senior ones. His answer was that if I thought I could find something that paid more, good luck to me.
Okay. I started looking.
Walking in confident
Here's the thing: I felt fine about it. I'd just rebuilt an entire application by myself and it was running in production. My website was up. I had every reason to think the market would be glad to see me.
Then I started doing interviews.
One of the first ones asked me a basic question about anonymous functions. I drew a complete blank. Couldn't answer it. Something that basic, and I had nothing.
I looked it up afterward. I'd been writing anonymous functions every day for the last two years. I just didn't know that's what they were called.
That kept happening. Interviewing for senior positions, I'd get asked to explain the mediator pattern, or chain of responsibility. I'd been building those things for years without ever learning they had names. I'd get a take-home project, build it, have it work, and then sit through a code review where it became clear my code wasn't something a team could live in.
I could do the work. I couldn't speak the language. And the language was what the interviews were testing.
Why I'm writing this
I'm not writing this because I have a system. I'm writing it because I was the guy who'd been in one place for years, whose skills had quietly gone stale, who had no idea how far behind he was until an interviewer asked him a question he couldn't answer.
If that's you, if you've been somewhere fifteen or twenty years and you're suddenly figuring out what's next, this blog is for you. Not "optimize your search." More like: you haven't interviewed in a long time, your identity is tied to one employer, and you don't know where to start.
I've been there. More than once, actually. That's the next post.
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