Everyone is starting over

It’s a Tuesday afternoon on a Zoom call, and someone asks me a question that hangs in the air: “If you were to start over again today, what skills, tools, or frameworks would you focus on learning?”

I glance out the window. It’s getting brisk. The sun feels brighter and sharper, the warmth that once felt like a bath now stings like a knife to my pupils. The green in the leaves is decaying into bright orange, a loud gasp before the fall. Inside the call, everyone waits for my answer. Outside, everything is becoming something else.

Well, I've got good and bad news: we're all starting over.

I don’t hear that question as advice for some earlier version of me, stepping into the world after years of incubation in college. It’s the question rattling around in the head of every designer whose hair is now more gray than not. The careers that thrive now are the ones willing to become someone new, over and over.

That sounds like the kind of line you’d see on a LinkedIn carousel. The annoying part is: this time the LinkedIn influencers are right! The ground is moving fast enough that treating what you know as permanent is starting to feel like a liability. The tools we use, the expectations people have, the way teams are structured—all of it is shifting under our feet. The thing that made you valuable three years ago might not even register as a differentiator today. You either keep updating the way you see the world, or the world finds a way to update you into irrelevance.

Donald Glover’s career comes to mind. That may seem like a strange place to go in the middle of a conversation about tech, but bear with me! Donald started out doing the safest version of the job: punch‑up writer on a network sitcom, then goofball ensemble guy on Community. It’s funny, it’s clever, it’s high‑status in a very specific 2010-internet way. He could’ve ridden that lane for twenty years but instead, he pivots into music with the pseudonym Childish Gambino.

The early albums lean into internet‑era rap, then he burns that down and shows up with Awaken, My Love!, which sounds like it got beamed in from a different decade Somewhere in there he’s making Atlanta, a show that starts as a scruffy FX comedy and then keeps mutating: surreal bottle episodes, horror, European art film, online conspiracy creepypasta.

Each career move shows one person refusing to let a successful version of themselves become a permanent assignment. Writer, actor, comedian, director, rapper, pop star, producer—none of those titles ever fully stick, because he keeps treating each one as a temporary skin.

That’s the move I’m talking about: breaking out of the last thing that made sense and trusting that your curiosity will build another version of you that works. Of course, that sounds romantic right up until you’re actually in the middle of it. But this is no time for skeptics.

Being enthusiastic about change, instead of merely tolerating it, opens up possibilities that didn’t exist even a year ago. The careers that thrive will be the ones that embrace the blur—the awkward, in‑between state where your role, your tools, and your skills don’t have clean labels.

Shigeru Miyamoto, the creator of Super Mario, has been practicing that blur for decades. He keeps reinventing the mechanics of the game, despite it being probably the most famous game of all time. They could have coasted on the original side‑scroller forever, just reskinning levels and adding more enemies. Instead, they keep blowing up the rules of what a “Mario game” is supposed to be. One generation it’s tight 2D platforming, the next it’s full 3D exploration, then it’s gravity puzzles in space, then it’s possession mechanics with a sentient hat.

Every time players settle into a stable picture of what Mario means, they tilt the whole thing on its axis and ask, “What if the core verb changed?” They keep the spirit the same, but they’re ruthless about reinventing the container. That’s the kind of reinvention most of us are being asked to do now, just at a smaller scale and without an orchestra behind us.

Reinvention, up close, is mostly about tolerance for embarrassment. If everything is changing, you will be bad at more things, more often, in front of more people. You will ask questions that make you feel like you should already know the answer. You will ship work that doesn’t quite land because the ground shifted halfway through. You will watch younger people move faster on tools you barely understand. The people who can metabolize that discomfort and keep moving will feel strangely calm in the chaos.

David Bowie spent decades as one of the most famous people on the planet and still treated his own identity like something he was allowed to scrap and redo. Every time the world got comfortable with one version of him, he killed it and walked out in a new skin. He treated his career as a series of experiments instead of a single answer. The risk of looking ridiculous for one album was worth more to him than the safety of repeating himself for twenty.

If reinvention is enthusiastically saying yes to what’s new, critical thinking is having the spine to say, “not like that.” The world is not suffering from a lack of ideas, but a lack of discernment. We’re drowning in things that look right but fall apart the second you press on them.

It's a new kind of uncanny valley: work that feels polished but empty. You can sense when something has never been held up against reality, when no one has asked, “Does this actually make sense?” It’s like looking at a stock photo of an idea.

Critical thinking is the refusal to accept that surface-level coherence as proof of value. It asks annoying questions: What is this actually saying? What would make this false? What would I have to believe for this to be a good idea? Who benefits if we’re wrong?

It's like that game we played as kids, where you had to spot the seven differences between two drawings. Except now the drawings are CEO statements, and the differences are tiny seams where the bullshit starts to show through. Sentences that sounds generous but don't promise anything.

Critical thinking is the refusal to let that stuff glide by just because it’s been nicely typeset. It’s the opposite of the lazy eye-roll. Cynicism is easy; you just decide everything is bad and call it taste. Critical thinking takes more work. It requires that you engage, that you follow the thread all the way through to the boring details: the edge cases, the tradeoffs, and the failure modes.

You can be wildly optimistic about what’s possible and still be ruthless about what’s real. In fact, the optimism only matters if you’re willing to protect it from nonsense. Reinvention says, “I’m open to this new thing,” critical thinking follows up with, “okay, now let's prove it's valuable.” One opens the door; the other checks ID.

Back on the Zoom call, the question is still sitting there: if I were starting over today, what would I focus on? The honest answer is less about any specific tool or framework and more about building the habit of becoming someone new, without becoming easy to fool.