The Road

The unemployment journal. Unfiltered. Started January 2026.

Here’s the thing nobody tells you about job hunting as a senior professional: it’s a full-time job that pays nothing and occasionally makes you question every decision you’ve ever made. I’m 30+ years into a tech career and I’m getting ghosted by recruiters fresh out of college. It’s a trip.

So I’m writing it down. Not because I need the therapy (okay, maybe a little), but because I think there are a lot of people on this same road who aren’t talking about it. Let’s talk about it.

The Numbers (Updated Regularly)

  • Job search started: January 2026
  • Applications submitted: More than I want to count
  • Interviews that went somewhere: A few good ones
  • Rejections that stung: All of them, honestly
  • Times I considered just going all-in on crypto: Daily

What I’m Looking For

Technical Program Manager. Developer Relations. Content strategy with technical depth. AI/automation roles where someone who actually builds things would be an asset. Remote or San Diego. I speak both human and engineer — that combination is rarer than it sounds.

What I’ve Learned So Far

The job market rewards persistence more than perfection. LinkedIn is a full contact sport. Everyone says they want “senior leadership” until they see the salary expectations. Coffee helps. Poker helps more. The dogs are excellent co-workers.

More entries coming. Check back, or subscribe to the newsletter where I occasionally let this bleed in.

Have a role that might fit? Let’s talk.

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