đ Hiya, job sneaker!
The senior leadership team was huddled around the latest five-alarm fire. The CEO shook his head, weary from weeks of acquisition negotiations and a seemingly endless stream of contractual red lines. He looked like he hadnât seen a pillow in three weeks. Tommy jumped in to take pointâhe was always the first into the flames.
After the meeting, he lingered by the window, watching the morning traffic thin out. The last four years had been a revelationâtrading the suffocation of enterprise bureaucracy for the beautiful chaos of building something from scratch.
When the acquisition papers were finally signed, champagne corks littered the floor. Tommy sat at his soon-to-be-someone-elseâs desk, facing an uncomfortable truth: heâd just orchestrated his own funeral. The parent company already had all its executive boxes thoroughly checked. His impressive collection of hats had suddenly gone out of style.
Late one night, nursing a scotch in the office speakeasy, he scrolled the job boards with the enthusiasm of someone shopping for a casket. The thought of being reincarnated as a corporate cog made him take an even bigger sip. Heâd gotten hooked on startup adrenalineâthat everythingâs-on-fire-but-isnât-it-thrilling energy. No way was he going back to a world where âthatâs not my jobâ was considered a core value.
His inbox buzzed. Outplacement services, courtesy of his severance package. The senderâs name looked familiarâof course it did. Many years ago, in a job far, far away, Tommy had spent two painful weeks calling everyone in his bossâs Rolodex to confirm their contact information. Those names had been popping up in his life ever since. He chuckled at how small the world still seemed.
With a heavy sigh and a little muscle memory, he began assembling his job search survival kit: LinkedIn alerts, tailored resumes, strategic outreach over coffee. The process hadnât changedâstill soul-crushing, just with a broader network. This time, though, he had Crunchbase. He could look up startup investors he knew and spot potential warm intros to founders.
His first promising leadâperfect on paper. It practically screamed you belong here. He ran his resume through the ATS checker included in the outplacement package.
Twenty percent match. TWENTY.
âSeriously?â he hissed at his laptop. Two decades of experience, reduced to a failing grade by an algorithm that probably couldnât tell a term sheet from a grocery list.
He word-smithed to match the keywords and got a better score, but it read like it belonged to some other guy named Tommy who wore beige. Not the first responder, he knew himself to be. Off it went anyway, into the voidâdozens more to follow.
Cold apps disappeared without a trace. Networking yielded mostly radio silence, with the occasional well-intended âIâll keep an eye out.â It felt like launching flares into a thunderstormâdesperately hoping someone would see them before he ran out of chances.
When a former investor emailed him about a startup that seemed like a perfect fit, it felt like the clouds might part. The founder took a meeting. Thirty rushed minutes later, the call endedâsurface barely scratched. The rejection hit his inbox before he could close Zoom. Apparently, thatâs all it takes these days.
His confidence smoldering like the last embers of a campfire, Tommy widened his search to includeâbig gulpâenterprise roles.
A director position at a major bank caught his eye. Not his dream, but at this point, worth a look. He noticed a former colleague on the team and reached out. One LinkedIn message later, they were catching up over a video call.
âRemember when you volunteered to update our old bossâs contact list?â she said. âI think I mysteriously got food poisoning that day and hid in the restroom.â
Tommy laughed. âHey, someone had to do it.â
âThatâs exactly what I need in this role,â she replied. âEveryone thinks enterprise means staying in your lane. I need someone who brings that get-it-done-no-matter-what energy.â
âWaitâyouâre the hiring manager?â Tommy blinked.
Now heâs back in a cubicle, sleeping with his eyes open while onboarding videos play: how to spot phishing emails, how to avoid injuries while sitting in an office chair, how to be a human that interacts with other humans. He wonders if heâs made a colossal mistake.
Then a shrill alarm pierces the quiet.
As he joins the procession to the stairwell, Tommy grins. Maybe this is just the fire drill before the real blaze. Maybe he wonât have to choose between job security and the thrill of putting out the flames after all.
The door prize? The job you land probably wonât come from a perfect resume or a flawless applicationâitâll come from the reputation you built when you thought no one was watching. Your value canât be measured by an algorithm, but it can be remembered by someone who saw you step up and deliver. Reach out to those people. Theyâre your best referrals, your strongest advocates.
And heyâif you ever find yourself staring down a severance package, try negotiating. Iâve talked to HR leadersâthereâs often more wiggle room than you think. Worst case, they say no. But you donât get what you donât ask for.
Onward through the smoke,
âď¸ Kirby