Episode 527: I lost my job after 10 years and am I too old to switch to a security career?

In this episode, Dave and Jamison answer these questions:

1. Hello Dave and Jamison!

   I’m a longtime listener going back to the early days of the podcast, and I’ve listened to every episode since. When I started listening, I was beginning my career as a software engineer. Your advice has truly helped shape how I think about work, engineering, leadership, and all the weird human stuff that comes with building software.

   Now I’m more than 10 years into my career, and I’ve run into a problem that I suspect many experienced engineers are dealing with right now.

   In episode 521, you talked about how brutal the current job market is, and the question asker from that episode had been unemployed for a year. I’m thankfully not there yet, but I recently lost my job in a large layoff, and the first couple of months of searching have been pretty discouraging.

   I’m applying to roughly 10–20 jobs a day. I tailor my resume to each role, ensuring it accurately reflects the skills and terminology in the job description. I usually include a cover letter too; AI gets the privilege of writing the mediocre first draft, and then I rewrite it into something I would actually say.

   Despite all of that, I’ve only made it past the resume screen three times so far, one of those was through a referral, and several other referral applications have gone nowhere.

   The strange part is that I’ve tried applying across the whole spectrum:

   1. Roles that would be a step up, where I think I could do the job but haven’t held that exact title before
   2. Roles at roughly my current level, where I can honestly check almost every box in the job description
   3. Roles that would technically be a step down, but that I’d happily take and feel extremely confident I could do well

   So my question is: How do you get companies to actually interview you when you’re an experienced engineer in a market overwhelmed with qualified candidates?

   At this point, I’m starting to wonder whether there’s such a thing as an awkward career middle age: too experienced for some jobs, not obviously senior enough for others, and competing with hundreds of people for everything in between.

   If you were in this situation, what would you change? More networking? Fewer but more focused applications? Different positioning? Showing up at the hiring manager’s house with a fruit basket and a printed copy of my GitHub profile?

   Would love to hear how you’d approach it from the other side of the hiring table.

2. Dave and Jamison,

   Hit me with your dumbest, funniest, most brutally honest advice because I need it.

   So here’s the deal: I’m a software engineer with 30+ year in the industry, a dinosaur who’s already reinvented himself like a half-dozen times, network, dev, infra consultant, back to dev. Now I’m having a midlife-ish (okay, late-life) crisis and I’ve fallen in love with security and compliance. Like, actually excited about compliance, which I’m told is a red flag in itself.

   Problem is: I’m less than 10 years from retirement and my brain doesn’t bounce back from “starting over” the way it used to when I was a spry young whippersnapper.

   So, am I an idiot for even considering torching my comfy expertise to go be a security newbie this close to the finish line? Or is this exactly the kind of chaotic energy I need before retirement?