Episode 527: I lost my job after 10 years and am I too old to switch to a security career?
<p>In this episode, Dave and Jamison answer these questions:</p> <ol> <li> <p>Hello Dave and Jamison!</p> <p>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.</p> <p>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.</p> <p>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.</p> <p>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.</p> <p>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.</p> <p>The strange part is that I’ve tried applying across the whole spectrum:</p> <ol> <li>Roles that would be a step up, where I think I could do the job but haven’t held that exact title before</li> <li>Roles at roughly my current level, where I can honestly check almost every box in the job description</li> <li>Roles that would technically be a step down, but that I’d happily take and feel extremely confident I could do well</li> </ol> <p>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?</p> <p>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.</p> <p>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?</p> <p>Would love to hear how you’d approach it from the other side of the hiring table.</p> </li> <li> <p>Dave and Jamison,</p> <p>Hit me with your dumbest, funniest, most brutally honest advice because I need it.</p> <p>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.</p> <p>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.</p> <p>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?</p> </li> </ol>
