You’re Not Behind. You’re Just Early to a New Way of Working

Why AI isn’t a race — and how play, experimentation, and mindset matter more than mastery.

The other day, I spoke with someone studying artificial intelligence. About halfway through, he paused and said, “Honestly, I don’t feel like I know what I’m doing.”

Another friend built a successful startup. You’d think he’d feel ahead of the curve. Instead? “It feels impossible to keep up.”

I hear this kind of thing from founders, students, and senior leaders—intelligent, accomplished, and curious people who still feel like they’re falling behind in learning to leverage AI effectively. 

But here’s the shift that helps me most: You’re not behind. You’re early. 

It’s like 1995 and the internet. The infrastructure is clunky. The use cases are unclear. Most people are still poking around, trying to figure out what this thing is for. That doesn’t mean you’ve missed the moment — it means the moment hasn’t even arrived yet.

The myth of “falling behind”

We’re living in a time when everyone feels like they should be experts in something no one fully understands. The pace is dizzying. Social feeds offer curated AI workflows with no trace of the mess beneath. Most of us were taught to see our careers as ladders—neat, linear, measurable.

But AI isn’t a ladder. It’s a maze that keeps redrawing itself while you’re still inside.

In The Uncertainty Advantage, I argue that we must replace our obsession with knowing the answers with a mindset built on adaptability, curiosity, and self-compassion. And there may be no better testing ground for that than learning to navigate AI, especially when the tools and rules shift by the week.

What if you treated AI like play, not performance?

What if the best way to learn AI wasn’t to optimize, but to play?

Children don’t start by reading user manuals. They try stuff. Build towers, knock them over, build again. They’re not afraid of being wrong — because they’re not trying to be right. They’re just engaged.

Play does something important: it lowers the stakes and creates emotional safety. In a world moving at warp speed, play might be the antidote we need most.

We don’t need more AI experts. We need more people willing to tinker without shame.

Three ways to start (without feeling like you’re drowning)

1. Pick one small task and mess with it. 

   
   

Don’t start with anything important. Start with something mildly annoying: rewriting a Slack message, summarizing a long email, or organizing a to-do list. Ask ChatGPT to make it snappier. Or sillier. Or like it was written by a pirate. See what happens.

2. Block two hours a week for “play-time R&D.”

   
   

No goals. No outcomes. Just a recurring calendar block to explore a new tool or a prompt idea. Not to be productive — just to get your hands dirty.

3. Keep a “What I Tried” doc.

   
   

Each week, jot down what you played with: what worked, what didn’t, what surprised you. You’re not building a system. You’re building awareness.

It’s not about mastery. It’s about mindset.

We’re all beta users of the future of work. The people who thrive won’t be the ones who memorize the most prompts. They’ll be the ones who build comfort with not knowing.

And that’s what The Uncertainty Advantage is really about. Thriving in this moment isn’t about having the answers — it’s about staying grounded when the answers keep changing. It’s about being kind to yourself when the path feels unclear. And yes: it’s about learning to play, even when the stakes feel high.

You’re not falling behind. You’re just stepping into something new.

Most people are waiting for a map. But there’s no leaderboard in a maze — just people exploring different turns.

So let go of the guilt. Let go of the pressure to catch up. And let yourself be a beginner — again, and again.

Because you’re not late.

You’re early.

And that’s a powerful place to be.

If you enjoyed this, you might like my newsletter, Scott’s Monthly Musings. It’s a curated selection of thought-provoking ideas, tools, and resources I’ve been exploring lately—especially around AI and the future of work. You can subscribe here.