An Elder Millennial Walks into a Job Interview…

The last time I really looked for a job, Iron Man had just hit theaters, iPhones still had a home button, and Twitter was a place where we told each other what we had for lunch. I was a young millennial on the rise, powered by Monster.com, a fresh haircut, and a newly minted hotmail address that didn’t include the year I was born. Fast forward to 2025, and I’m once again back on the hunt — older, wiser, and significantly more dependent on ergonomic desk chairs.

Let me just say: the job market in 2025 is WILD.

Back in 2008, job applications felt like courting someone you met at a bar. A little charm, a solid resume, and boom — interview. Now it’s more like trying to get a date on a niche dating app for people who exclusively speak in “core competencies” and ATS-optimized PDFs. Everyone’s trying to be “a strategic storyteller with a data-first mindset who thrives in ambiguous environments.” I’m just trying to remember my LinkedIn password.

And let’s talk about LinkedIn. Oh, LinkedIn. It used to be the place you went once a year when your boss said something sketchy. Now it’s where people write emotional essays about how they once got rejected from an unpaid internship but learned so much about resilience they got hired as a VP three weeks later. Meanwhile, I’m over here trying to figure out whether it’s better to “demonstrate cross-functional leadership” or just say I’m good at working with people.

Here’s what hasn’t changed: I still love marketing. I still love storytelling. And I still believe that the best way to sell a product is to make someone feel something. That’s been true whether I was working with Windows PCs, launching Copilot+ PC campaigns, or convincing a youth flag football team that wearing eye black doesn’t help all that much when we aren’t playing under lights.

But what has changed — besides literally everything — is how you go about showing that.

I’ve spent the last decade at Microsoft, working at the intersection of hardware, software, and marketing strategy. I partnered with global OEMs, silicon partners, and brand teams to bring some of the most complex co-marketing campaigns to life. I helped position Windows against MacBooks, found ways to make AMD and Intel coexist peacefully (no small feat), and worked across time zones, verticals, and Teams threads that should’ve been emails. And now that chapter’s closed — through no fault of my own — and I’m embracing the chaos that is unemployment in 2025.

At first, it felt like a vacation. I reorganized the garage, learned what a berm is (and seriously considered building one), coached my kids’ baseball teams, and caught up on sleep I’ve owed myself since the Bush administration. But then the existential panic set in. My email signature was gone. My calendar was empty. My only “team meeting” was with my son to discuss whether Minecraft time counted as screen time or Create time. (I still say it’s screen time.)

So I did what any rational, recently laid-off millennial would do: I updated my résumé, added “strategic” to everything, and fired up the old LinkedIn. I started blogging again. I created baseball logos, dug into personal branding, and considered a side hustle involving custom wood-burned signs that say “Live, Laugh, Launch GTM Strategy.”

But mostly, I’ve been reconnecting — with the work I love, with people who inspire me, and with that version of myself who used to apply to jobs with a genuine sense of excitement instead of muted dread.

Look, the truth is, I’m good at what I do. And if you know me, you know that I’ve always been a mix of sarcasm, strategy, and good storytelling instincts. Whether I’m crafting value props for tech launches or coming up with ridiculous Lego projects for my kid, I know how to make things land. With humans.

And that’s the funny part of all this: in a world where AI can write emails, optimize campaigns, and draft blog posts (No AI was used to write this post… OR WAS IT?!?!), the one thing it still can’t do well is be human. It can’t coach a Little League team while brainstorming a tagline. It can’t understand the chaos of trying to launch a marketing campaign across six countries with two engineers, one designer, and an intern who’s allergic to email. It can’t sit across from a partner and ask, “What’s the real story here?” — and then make that story stick.

But I can.

So yeah, I’m back on the market. First time in a long time. My jeans are more comfortable, my vision is worse, and I now judge potential roles by whether the company’s perks include access to sitters. But I’m also sharper, more creative, and more passionate about great work than I’ve ever been.

Let’s build something — or at least complain about TikTok trends together.

I’m just a message away.

And yes, I’m still a Windows PC guy.

The below picture was my FB profile pic from 2008… Did I think I was auditioning for Fall Out Boy?