How to Learn
A few minutes after I finished giving a talk on AI trends last week, as the audience began to disperse and the noise in the room started to fade, a young man approached me.
He was quiet, maybe a little nervous, and had waited until the crowd had thinned before stepping forward. He was the only university student in the room—surrounded by professionals, founders, and technologists twice his age—but he had clearly been paying close attention.
He asked me, simply, “How do I learn AI?”
There was something innocent in his voice. Not the kind of question meant to impress, but the kind that carries the weight of genuine curiosity. The kind of question I might have asked when I was his age. The kind I don’t hear very often anymore.
I asked him what he had been doing so far.
He told me about a few online courses he had taken, some YouTube videos he liked, and a handful of small projects he had already started building. He was clearly excited—eager to show me what he was working on on his phone, proud of what he had created, even if it wasn’t polished. His enthusiasm was infectious. And it stirred something in me that I hadn’t felt in a long time.
When was the last time I was that excited to learn?
I used to love learning.
I learned to walk by watching others around me. I learned to speak by listening to the sounds that surrounded me. I learned to read and count and write not because I had to, but because it was all new, and I was ready.
I was open. I was unafraid. I was constantly observing, mimicking, trying. I failed all the time, but I didn’t even notice or label it as failures or mistakes. That’s just what learning looked like.
The first twenty years of my life were dedicated to learning. That was the purpose of life. Every environment I was in—from school to home to the playground—was designed around the idea that I didn’t know, and that not knowing was okay. In fact, it was expected.
I miss that.
Because the next twenty years, for me, were mostly about working. And sure, there was learning in that too—learning how to navigate teams, how to lead, how to manage complexity, how to solve problems. But it was a different kind of learning. It was linear. It was goal-oriented. It was focused on output, on performance, on mastery. The kind of learning that fits neatly into a spreadsheet or a resume.
Through working, I learned how to get things done efficiently, effectively, and reliably. But that kind of learning rarely felt playful. It didn’t feel free. There was always a deadline, always a deliverable, always someone expecting something from me.
Somewhere along the way, I also developed the belief that I should already know. That being new at something was a sign of failure. That asking questions revealed weakness. That unless I was good at something, it probably wasn’t worth doing. But that’s the lie.
The truth is that learning, by definition, begins with not knowing. And there’s a certain grace in that. A humility. A quiet strength in being able to say: this is new to me. I don’t know how to do it yet. And that’s okay. That’s the whole point.
The challenge, though, is that as adults we become attached to who we think we are.
I’ve noticed this in myself. I start to say things like “I’m a founder,” or “I’m an investor,” or “I’m a writer.” And each of those statements, while useful in certain contexts, begins to define the boundaries of what I allow myself to explore. If I’m a founder, then I should know how to build businesses. If I’m a writer, then I should be exceptional at expressing myself. There’s less room for surprise. Less room for play.
Back to the student who approached me after my talk. He began showing me a few of the projects he had built using AI—small tools, clever experiments, things he had thrown together using open-source models and APIs. Then he asked me, “Do you think any of these could make money?”
I stopped him. Not because it was a bad question. But because it wasn’t the right one for that moment.
“Why does it need to make money?” I asked.
He looked at me, unsure how to respond. “I guess… I thought that’s what I was supposed to do.”
There was a pause between us. I could see him thinking. I could also see him wondering if he had said something wrong. I filled the silence by reminding him of his original question. He had asked me how to learn AI. Not how to monetize it. Not how to build a company. Not how to become a success story.
I told him to keep building. To keep experimenting. To keep launching new projects—every single week, if he could. Not because one of them might work. But because the act of doing is the real learning. Not the videos. Not the podcasts. Not the reading. Not the articles or courses or conversations.
His face lit up. There was a visible shift in his posture. I could feel his excitement begin to return, maybe even deepen. “So,” he asked, “if I just keep trying ideas, one of them will eventually work?”
“No,” I said, again challenging him, without hesitation. “That’s not the point.”
The purpose isn’t to get one of your ideas to work. The purpose is to keep learning. To keep pulling the thread of your own curiosity, without needing to know where it leads.
And maybe that’s the hardest part.
As adults, we become so oriented around outcomes. We want results. We want validation. We want our time to feel productive, our effort to be justified. But learning doesn’t work that way. Not the kind of learning that expands us. Not the kind that lights us up. That kind of learning can’t be scheduled or measured
Play is a word I’ve been coming back to more often lately. Children learn through play not because it’s a strategy, but because it’s an instinct. It’s how they make sense of the world. And when I think back on the moments when I’ve learned the most in recent years, they haven’t been when I was trying to learn. They’ve been when I was trying something new just for the sake of it. When I allowed myself to experiment. To explore. To play.
Learning, I’m starting to remember, is not something to achieve. It’s something to return to. Something to remember. A part of myself I once knew well and, somewhere along the way, misplaced.
The student didn’t need a roadmap. He needed a reminder. And without meaning to, he gave one back to me.
And that is how I learned to learn.
