A few weeks ago a rising high school senior cold-emailed me. He was trying to build a network and get advice on breaking into finance.
I want to pause on that for a second, because it is impressive. He is seventeen. He wrote to a stranger to ask for guidance. He had already emailed a bunch of other people too. And he had landed a real internship at a large investment firm through a competitive city program he had applied to and won. That is ambition firing on every cylinder: he went and got the thing, and he was still hustling to learn more.
So I was rooting for this kid completely.
And then he said something that stopped me cold.
He told me the main lesson he had absorbed at this prestigious internship was: keep your head down, just do your job, and do not bother doing extra, because it will not get noticed.
Seventeen years old. In the building. And someone had already taught him to make himself small.
I told him, as directly as I could, that this was some of the worst career advice I had ever heard. He was genuinely shocked. I do not think anyone had ever pushed back on it.
So let me tell you what I told him, because if you have ever heard some version of “don’t make waves, just do your work,” I want you to hear this.
That advice is not neutral. It is poison, especially at the start of a career. Everything I have watched work over twenty years is the exact opposite of keeping your head down. The people who build real careers are the ones who do more than they are asked, who make themselves useful in ways nobody requested, who are a little too visible. I have told you about some of them already, the guy who taught himself Spanish because he saw customers nobody could serve, the swimmer who showed up early and helped with projects he did not even understand yet. Not one of them got ahead by blending in.
But here is the part I really want you to understand, because it is the deeper truth.
The reason that internship taught him to disappear probably has nothing to do with him. It is a symptom of the place.
Some companies quietly train the ambition out of people. Not on purpose, usually. It is just the culture. Do your task, do not rock the boat, wait your turn. And it works, in the worst way. I know people who spent years at exactly this kind of company. They kept their heads down. They did their jobs well. And they looked up ten years later still in more or less the same seat, having been rewarded the whole time for not standing out. They were trained into complacency, and by the time they noticed, a decade was gone.
A 17-year-old should be nowhere near that lesson. He should be out hustling, taking on more, making himself impossible to ignore. Instead he spent a summer at a desk being taught to watch the clock.
Now, I will be honest with you about something, because it complicates my own advice and I would rather be straight with you than tidy.
I usually tell high school students not to chase fancy internships at all. Go get a real job. Lifeguard. Wait tables. Bag groceries. Do landscaping. Learn what it means to show up, work hard, and deal with actual human beings, because that teaches you more at that age than sitting in a corporate office ever will. And honestly, this conversation kind of proved my point. Here was a kid who did land the impressive, prestigious thing, and the impressive prestigious thing taught him to make himself small. He might have learned more about drive from a summer of hard, unglamorous work than from a summer of meaningless tasks at a big-name firm.
So here is the principle that ties it all together, and it is one of the truest things I know about work:
Work somewhere you are always either learning something or making a meaningful contribution. Ideally both. If neither is true, you should not stick around, no matter how good the name looks on your resume.
That kid’s internship failed that test. He was not learning, and he was not contributing anything real. And instead of recognizing that as the problem, he had been taught to see it as normal, and to shrink himself to fit it.
Do not shrink yourself to fit a place that is not growing you.
Keep your head up. Do more than they ask. Be a little too visible. And if you find yourself somewhere that punishes that instead of rewarding it, take the real lesson, which is not “keep your head down.” It is “you are in the wrong room. Go find a better one.”
Talk soon,
Jeff
P.S. Hit reply and tell me: what is a piece of career advice you were given that never sat right with you? I am collecting these, and the ones that come up again and again might become a future issue.