Field Notes
Look for the Plus Sign
Dan Hebert · September 22, 2026
Not every posting is for you
When you've been in one place for fifteen or twenty years, the first instinct is to apply to everything you're capable of doing. You're capable of a lot. That's the problem.
A big share of the postings out there aren't looking for you, and some of the ones that look easiest are the ones you'll never hear back from. Learning to tell the difference saved me weeks.
Startups are a different kind of people
A lot of startups are built to grow fast, sell, and move on to the next one. They know they'll have turnover, so they want workers, not twenty-year employees. The room tends to skew young.
If you walk into an interview and feel like the dad in the room, it's probably not going to work out, and that's got nothing to do with your skills. People don't want to go to work with their dad.
If you are that younger audience, hit the startups hard. Great money, great experience. If you're looking for the next fifteen years, they're mostly a detour.
Big tech is a different kind of people too
I've interviewed with a couple of the names you know. The loops are a full day. The environments can be cut-throat, and anything that looks like a greenfield project turns into a fight to get on it.
That's for a certain kind of person. If you just spent fifteen or twenty years somewhere you liked, it's probably not you, and there's no shame in that.
Overqualified is real
Here's the one that surprised me. You see a posting asking for two or three years of experience that pays more than you were making. You've got twenty. Easy, right?
You won't get a call.
From their side, the question is: why would someone with twenty years take an entry-level job? You're using us as a stepping stone. You're not here for us. They want someone who'll stay, and you look like someone who'll leave.
There's a second reason nobody says out loud. A lot of hiring managers have ten years in. Ten years is respectable, and they're proud of it. Are they going to hire someone with twenty to report to them? Some will. Many won't, because you'll make them look like they don't know what they're doing.
Read the posting for the plus sign
So here's what to look for: 7+, 10+, 15+. When a posting says "ten or more years," they're telling you they want experience and they've made peace with what that costs. Those are your postings.
"Three to five years" is a builder spot. They want someone who'll grow into it and stick around. You can still apply, and some will bring you in anyway. Just don't spend your best hours there.
Where you probably fit
If you were somewhere a long time and you're looking for somewhere to be a long time again, you're most likely looking for a smaller, established company in a market that isn't shifting under it. Not a startup. Not one of the giants. Somewhere that's been around, has stable customers, and needs someone who's seen a few things.
Read the reviews. Check how long they've been in business. Then aim there, and stop wasting days on the ones that were never going to fit.
When you find the right one, you'll know it in the interview. They've been looking for you as long as you've been looking for them.
Next: the résumé. Why I don't cut mine to one page, and what a standard résumé leaves out.
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