You can’t Connect the Dots you don’t have yet

A few weeks ago, I visited my alma mater and spent some time talking with the current students. At some point one of them, second year, asked me the question I keep hearing in different shapes. He’d been searching for internships. Mostly every listing mentioned the need of “AI skills,” most wanted experience for what was supposed to be an internship. He’s nineteen. He asked me, half joking but not really, “Sir, what am I actually supposed to do?”
I gave him an answer in the room. But the honest version of that answer is longer than what I could say between two classes, so let me write the rest of it here for anyone sitting where he’s sitting.
What I told him is more or less what I, and most of the other mentors there, tend to tell today’s youth. Upskill. Learn AI. Be a generalist. Then came his follow-up. What does “be a generalist” even mean? I told him in the moment that it’s about knowing a little about everything and being able to handle whatever comes your way. But the second the words left my mouth; something nagged at me. “Be a generalist” is the kind of thing you say to a person who already has range. I’ve spent more than twenty years in this industry now, and I got here by going deep in one or two things first, earning the right to wander between things only later. Telling a nineteen-year-old with a blank resume to go wander might not make much sense to him. He doesn’t have the dots to connect yet.
Then he asked the question everyone asks. Which field should he pick. Software, finance, design, the usual menu. And this is where I want to be careful, because I used to answer that like it was a question with an answer. Pick the one with scope. Pick the one that pays. Pick the one you’re good at.
I don’t believe that anymore, and this part is more for you, the reader, than it was for him in that moment. A beginner cannot pick well. Not because he’s lazy or indecisive. Because the information he’d need to choose doesn’t exist in his head yet. You don’t know whether you can stand finance until you’ve sat with a broken spreadsheet at one in the morning and noticed whether you feel dread or a strange kind of calm. You don’t know if design is yours until you’ve made something ugly and felt the itch to fix it instead of the urge to shut the laptop. None of that lives in your head before you start. You find it in your hands.
That’s the part the advice gets backwards. Everyone tells you to choose your specialty and then go deep. But a beginner doesn’t choose depth, he stumbles into it. The vertical gets discovered through the horizontal, by trying five small things and noticing which one you didn’t want to put down. The exploring isn’t a reward you unlock after specializing. For someone just starting, it’s the only way to figure out what to specialize in at all.
So, what I actually told the student was simple. Stop trying to decide and start trying to build. Small things. Slightly embarrassing things. A little site for a relative’s shop. A tool that helps the stationery store down the lane track what’s running out. A bot that answers the three questions your classmates keep asking you anyway. It does not matter what it is. What matters is crossing the line almost nobody in college crosses, the line between consuming and making.
Most students spend three years on the consuming side. Lectures, courses, videos, more courses. Watching is comfortable. Making is where you find out how much you actually know, which is usually a lot less than the certificate suggested. And that is exactly why it works.
Here’s what I want the readers to really sit with. Building gives you something a course never can. Proof. Right now, a student walks into a room and says, “I completed five AI courses,” and that sentence is worth almost nothing, because the ten people in the queue behind him say the same one. The student who says “I built a small billing tool for a shop near my house, and it’s been running since March” is in a completely different conversation. One of them is describing what he absorbed. The other is showing what he can do. The second one wins, and it isn’t close.
I told the student the same thing I’ll tell you. The ones who pull ahead aren’t smarter. I’ve watched enough of them to be sure. They just start earlier and they’re willing to make worse things in public. It breaks, they fix it, they put it where someone can see it. The ones who wait, for the right course or the right semester or placement season, are standing at the same line a year later while the builders have ten ugly projects and a real sense of what they’re good at.
By the time I left the campus that day, the thing I most wanted that student to keep was this, and I’ll leave you with it too. When someone asks me to know what they should learn, I don’t hand them a subject. I hand them a deadline. Build something small by Sunday and tell me what broke. It’s the only upskilling advice I still trust, because it’s the only kind that survives contact with a nervous nineteen-year-old who’s already sure he’s behind.
^{Disclaimer: The thoughts and views in this piece are entirely my own. AI was used only to help with grammar and proofreading.}