Career reboot

Issue 244: Re-thinking my approach during the AI Incursion

Every April I seem to take an unplanned creative spring break. It’s not a sabbatical or a formal PTO strategy—just a self-imposed ritual to step away from the chaos of work and reconnect with what inspires me. I’ve learned that if you’re not in a full-time IC role, making things—especially design—becomes a form of recovery from meeting fatigue and managerial overhead.

This year’s reboot took me to San Diego and Palm Springs, where I spent the week writing, vibe coding, updating my site, and binging content—not passively, but actively, taking notes like a student of inspiration. It’s a reminder that creative recovery isn’t idle time; it’s compost for what comes next.

One of the shows I caught up on was Daredevil: Born Again—a reboot of one of my all-time favorite comic book characters. After finishing it, I fell into one of my favorite internet rituals: watching YouTube breakdowns from New Rockstars, Screen Crush, and Heavy Spoilers. The algorithm did its thing, and suddenly I was watching clips from the original Daredevil series that aired on Netflix in 2015. Ten years ago. I was living in Capitol Hill, Seattle, designing mobile apps at Black Pixel, deep in my craft.

Pandora’s Box was open. From there, it spiraled into Secret Wars theory videos and MCU reboot rumors. It’s no secret that Marvel is plotting a reset. Though my heart still belongs to the 1984 Secret Wars, the upcoming cinematic version borrows heavily from Jonathan Hickman’s 2015 arc—the one where the multiverse collapses, Doctor Doom ascends, and the patchwork world of Battleworld emerges from the ruins.

As the Marvel multiverse collapses from a series of catastrophic incursions, Doctor Doom seizes godlike power and creates a new patchwork world called Battleworld, where fragments of destroyed realities are stitched together under his rule. Avengers: Secret Wars is set to release in 2027, which is fifteen years after the original Avengers film.

The AI incursion

I was sitting on our couch in Palm Springs, flipping through YouTube clips between the two Coachella weekends—an event I once flew across the country to attend (yes, I was there for Hologram 2Pac). Now, the bands that once headlined my youth are soundtracking ads for minivans and insurance, targeting geriatric millennials like me. Bryan Johnson might argue I’m not getting old, just aging. But let’s be honest—I’m losing my edge.

The hardest part of aging isn’t the number—it’s the creeping sense of irrelevance. That quiet panic when you realize you’re no longer fluent in the tools or jokes shaping the next era. For many of us, the AI incursion feels like that moment. Unlike past hype cycles—remember NFTs?—this one feels different. Real. Fast. Disruptive. Existential.

We’re not just navigating a new wave of tech; we’re dealing with two systemic shocks at once. The AI acceleration is colliding with what feels like the second Great Recession. Around 2023, tech hit a hard reset—blitzscaling gave way to layoffs, cautious capital, and a culture shift. And from that rubble, a new archetype emerged: the vibe coders. A term Andrej Karpathy used to describe the new generation building apps with generative AI—no traditional coding required, just vibes, vision, and a good prompt.

Using generative AI, I had Chat GPT write a satire of Losing My Edge about vibe coders and a millennial trying to keep up with the gen z kids:

I’m losing my edge…to the kids with ring lights and one-shot prompts, the ones who ship from Discord DMs and sleep in Notion.

I remember when we wrote our own auth, when you had to beg Heroku for more dynos.

I remember debugging IE6 in Starbucks on airport Wi-Fi.

I remember when product specs were PDFs, when A/B tests took weeks and no one said “vibes.”

I’m losing my edge…to the locked-in Gen Zs with Arc tabs like trading desks, shipping AI agents at 3AM while I’m still writing the brief.

Tech incursions equalize

Millennials, we’re losing our edge. The experience we once relied on—the war stories of scaling, shipping, and staying late to debug—no longer guarantees relevance. The Ruby on Rails apps we built with Twitter Bootstrap and deployed on Heroku? They can now be replicated in a single shot prompt with generative AI. Even Reid Hoffman, the founder of LinkedIn, used Replit to spin up a clone of the platform he originally built. Just because you can mimic something doesn’t mean you’ve matched its scale or impact—but using that as a reason to dismiss what’s happening is a mistake.

As General Eric Shinseki once said: “If you don’t like change, you’re going to like irrelevance even less.”

The upside of these tech incursions is that they act as great equalizers. They flatten the hierarchy. They don’t care how senior you are or how many portfolio pieces you’ve amassed—they care how quickly you can adapt. Whether you’re just starting out or decades into your career, everyone is trying to figure out how to design with AI while designing for AI.

I’ve seen this pattern before. In my 20s, during the mobile incursion, no one had experience designing for a piece of glass you touched with your fingers. I managed to break into tech because I had mastered Photoshop and could craft rich, skeuomorphic interfaces. In a landscape with no established veterans, everyone was new—and that opened doors.

It’s tempting to push back by saying, “But I have decades of experience.” And sure, experience matters. But relevant experience matters more. I remember a graphic design professor from college—someone who had written books, spoken at conferences, and built a career in print. He refused to teach web design, dismissing it as a fad. That mindset didn’t age well.

There are still strengths that tech incursions can’t displace—understanding customers, navigating complexity, and leading teams across disciplines. But we can’t ignore how the craft itself is changing. And if you’re a design leader, your job isn’t just to set direction—it’s to stay close enough to the work to guide your team through the shifts. Because when the ground moves, they’ll need you to be steady and skilled.

Career reboot

As my spring break wraps up, I’m not walking away feeling old—I’m walking away with a sense of clarity: it’s time for a career reboot. Two years ago, I called the tech factory reset. Now, I’m giving myself permission to do the same. A reboot doesn’t mean discarding everything. The valuable experiences, the hard-earned instincts—they re-install quickly. What I am letting go of are the dependencies and assumptions that no longer serve me. The ones that keep you comfortable but slowly make you obsolete.

I don’t need to be recast as the lead in someone else’s Marvel reboot. I want to play a different role: the bridge between generations, helping to pass the torch—not by clinging to the past, but by staying grounded in it while reaching toward what’s next.

To do that, I’m making a few commitments:

• Stay healthy and well. Don’t let burnout rob you of clarity or connection. Take care of your mind, body, and the people who matter.

• Keep the craft blade sharp. Return to your roots. Lead through craft. Understand the material of this new era—especially AI. As Nikunj Kothari put it: stop bookmarking, start building.

• Invest in the next generation. Mentor. Share your playbook. Let their perspective reshape yours, too.

I was an IC running my own studio when The Avengers hit theaters. Now, fifteen years later, I’m an operator and investor as Secret Wars looms. My 20s were shaped by the Mobile Incursion in Seattle. My 30s, the Blitzscaling Era in San Francisco. And now, in my 40s, I’m back in San Francisco, navigating the AI Incursion.

This isn’t the end of an era. It’s the beginning of another. I don’t feel irrelevant—I feel rebooted. And I’m working on the most relevant things in my career.

Let’s get back to work. See you at the reboot.

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Hyperlinks + notes

• Baseline #28 – Buying Back My Time (and What It’s Teaching Me) by Joey Banks

• What?! 108-Gigapixel Scan of Vermeer’s Girl with a Pearl Earring

• Raising money isn’t success by

  Sophia Amoruso

• Hope to catch you at Config in San Francisco!