07. Coloring Outside the Lines | The Truth About Entrepreneurship
- Ben Steenstra
- Jul 16
- 4 min read
Society tells us to get good grades, to learn what’s expected, and to color neatly inside the lines. But here’s the truth they rarely tell you: entrepreneurship isn’t about following rules. It’s about breaking them, creating your own path, and learning by actually doing.
Let me show you exactly what I mean. I’ve always been kind of an autodidact. Honestly, school and I didn’t click at all. Early on, I realized the traditional education system just wasn’t my thing. I preferred football, tennis, hockey - or simply hanging out with friends. It’s not that I was lazy, far from it. I just felt school was wasting my time. Homework was a five-minute affair before class, until exam season came around.
I remember one surprise test vividly. I hadn’t studied at all, and this test was important. If I failed, I wouldn’t even be allowed to take the final exams. I still see the teacher’s face clearly: Mr. Hof. He knew exactly how badly I was messing up. So he calmly said, “You’ll get another completely unexpected test tomorrow. Be prepared.”
So what did I do? I went straight to the tennis court, hung out with friends afterward, learned absolutely nothing, and showed up again the next day completely unprepared, obviously. Another big, fat failure. Mr. Hof just shook his head and said, “Fine, I’ll just give you a passing grade. Honestly, the thought of having you in my class for another year is unbearable.”
Now, why am I telling you this? Because our society drills into us the idea that good grades matter most, that we need to color strictly inside the lines, and that we must learn exactly what the system tells us. As if we’re all identical robots without unique talents, skills, or interests.
Sure, some basic knowledge is useful. But beyond that? If I decide to learn Spanish or French, I’ll nail it in three months. Economics? Even the greatest economists in the world disagree constantly, so what’s the point of absorbing outdated theories from dusty textbooks?
When Richard Branson started his airline, Virgin Atlantic, he spent just three months getting to know how the industry worked. Even that felt like too much for him. He firmly believes—just like I do—that you can learn almost anything you really want within three months. Of course, I’m not talking about specialized fields like medicine, chemistry, or architecture. Those obviously require deeper study. But entrepreneurship? That’s different.
Too many people delay starting their own business because they think they lack knowledge. Another course here, another degree there—it’s endless. But the truth is, you learn the most by simply starting. By doing the work. By getting out there and figuring it out.
And here’s what’s really messed up: it’s not just that schools make you learn a ton of stuff you’ll never use again. The real issue is that they teach you to always color neatly inside the lines. And guess what? Entrepreneurship is exactly the opposite. It’s about coloring outside the lines. It’s about creating something of your own. Something original.
Think about it. If you always do exactly what you’re told, the results you get will always be exactly the same. You’ll never move forward. You’ll never innovate.
Imagine Richard Branson’s mother telling him, “No Richard, first get your diploma, then maybe—just maybe—you can start your little airline.” Or Elon Musk’s mom saying, “Elon, finish your technical university degree first, then we can talk about rockets.” No way. Whatever you might think of these guys, they never even saw the lines. They just started coloring. The educational system as it exists today? It would have crushed them before they even started.
Did you know that our educational system was actually developed to make us obedient? It was designed to train us to do exactly what’s said from above. This goes all the way back to the Industrial Revolution, when we were literally seen as extensions of machines—just replaceable parts that weren’t supposed to think for themselves. And honestly, since then, we haven’t made many changes.
Now, don’t get me wrong. I’m not against education. Not at all. But I am very much in favor of exploring new paths, of thinking independently, of learning through experience, and of not blindly trusting established knowledge. Because think about it: if everyone just followed the crowd, we’d still be riding around in horse-drawn carriages. At a time when people were busy figuring out how to make horses run faster and longer, someone had to imagine doing things smarter and quicker—without the horses at all.
Let me be clear: I’m not saying education is bad. Quite the opposite. For some people, the current system works perfectly fine. Some even choose to become teachers within that obedient system. That’s their choice. It’s just definitely not mine.
There’s a famous story about a great pianist who was asked to give lessons to a very talented, conservatory-trained student. He agreed. When the student arrived, the pianist was just finishing a lesson with a beginner. After the beginner left, he paid the pianist 15 euros. The conservatory student looked surprised and asked, “Excuse me, sir, you're charging me 100 euros per lesson, and I'm already advanced. Why did that beginner only pay 15 euros?” The pianist smiled and said, “That’s simple. I can teach that beginner everything he needs to know right away. But with you? For the first few months, I’ll have to spend all my energy helping you unlearn everything you’ve already been taught.”
In practice, this is exactly how it goes. Every time I hired people straight out of university, I spent the first weeks undoing outdated theories and explaining that what they’d learned just doesn’t work that way in real life.
So here’s the bottom line. Knowledge is useful, absolutely. But the real magic happens when you dare to step beyond what you already know. When you stop waiting for permission and start creating your own path. Don’t become just another extension of the machine. Be the one who builds a new one. Because true entrepreneurship isn’t about what you’ve learned. It’s about what you’re willing to discover.
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