Maybe It's Time to Stop Climbing Someone Else's Ladder?
Entrepreneur Office Hours - Issue #335
Inside the Office
Every spring, I watch my students stress about internships.
Applications. Interviews. Rejections. LinkedIn announcements. Comparisons. The pressure is immense. Internships have become a currency of college achievement, and the assumption is simple: the better the internship, the better your future.
Lately, though, I’ve found myself wondering whether we’ve become a little too focused on climbing someone else’s ladder.
Twenty years ago, I landed what felt like a dream internship with a large global organization in Washington, DC. Every morning, I walked down 17th Street straight past the White House on my way to the office. I remember feeling like I was on top of the world. I was working for important people doing important work in an important city. Isn’t this what it’s all about?
To put a cherry on top of the summer, the organization sent me to its flagship conference, basically the equivalent of that industry’s World Cup. High profile people were there from all over the world. This was it - the proverbial “room where it happens.” And I, the intern, had been given the privilege to be a fly on the wall, getting a sneak peek into what my future might hold.
And I remember sitting in the back of that room, looking around, and having a surprisingly clear thought:
If this is the view from the top of the mountain, this is not the mountain I want to be climbing.
Nothing was wrong with the organization or the people. Many of them were extraordinarily talented and successful.
I just couldn’t see myself there. It wasn’t “me.”
Looking back, I wish I had spent at least one summer working on a startup idea with friends instead.
Not because the startup would have succeeded. Most don’t.
But because I would have learned more by doing than waiting to be told what to do.
When you’re building something from scratch, you have to figure things out for yourself. You talk to customers. You test assumptions. You hear feedback you don’t want to hear. You discover whether the problem you’re solving actually matters to anyone besides you.
You learn how to navigate ambiguity rather than wait for instructions.
Most importantly, you learn how to learn.
When we’re young, we often assume knowledge lives somewhere “out there” and that our job is to find the right expert, company, or internship to give us the answers.
Entrepreneurship teaches a different lesson.
The answers are often uncovered through curiosity and directed action. You learn by taking a step, observing what happens, learning what you have to learn, and taking another. The skill isn’t already knowing. The skill is figuring things out.
As I think about today’s students, I wonder if this mindset is becoming even more important. AI is already reshaping entry-level work. Many of the jobs that once served as apprenticeships may look very different in the years ahead.
So perhaps the question isn’t only, “How do I get the most prestigious internship?”
Perhaps it’s also, “How do I become the kind of person who can create opportunities when they aren’t handed to me?”
Internships can be incredibly valuable. Mine certainly was. It taught me something I couldn’t have learned any other way: success isn’t about reaching the top of a mountain. It’s about discovering whether it’s your mountain in the first place.
And sometimes the fastest way to find your mountain is not by working for someone else’s dream, but by spending a summer exploring one of your own.
-Amy
Worth Your Time
In class last week I was chatting with a student who was a bit too focused on how much money he thought he could make building a Silicon-Valley-style venture-backed company. In response, I explained that if his primary goal was simply making money, he’d probably be better off spending five years learning the HVAC business and then starting his own repair company.
To be clear, that’s by no means an easy path to wealth. But people are always going to need air conditioning, and, right now, the world doesn’t have enough skilled humans to install and repair them. Simply put, it’s a safer bet than whatever brilliant app he might have been planning.
A few days later, the student sent me this article from Andreessen Horowitz, and I thought it did a great job explaining the underlying economics. The piece explores why things like air conditioners have become relatively inexpensive while the services required to install, maintain, and repair them have become increasingly valuable. The short version is that technology and globalization tend to drive down the cost of products, but local expertise remains stubbornly scarce.
It’s a good reminder of the underlying reasons why every opportunity doesn’t look like Silicon Valley and also why some of the best opportunities are hiding in plain sight inside industries most people ignore. Entrepreneurs often chase whatever is trendy because that’s where attention is. Meanwhile, enormous businesses are constantly being built around solving unglamorous problems for customers who desperately need help.