The Most Successful Entrepreneurs Are Never Rule-Breakers

Entrepreneurs who think “rules are meant to be broken” are completely missing the point.

Photo by Mark Duffel on Unsplash

I came across a video on TikTok the other day where a woman was explaining the real secret to becoming successful. According to her, successful people all believe the rules don’t apply to them. The rest of us follow the rules like a bunch of suckers, she said, while the people who actually get ahead in the world just do whatever they want. So the takeaway was simple. If you want to be successful, stop caring so much about the rules.

I’ll admit she’s certainly noticing something real, and I say that as someone who spends most of his time around startup founders, where this exact philosophy is basically the house religion. Founders love the phrase “ask forgiveness, not permission.” They repeat it like a mantra. And there are plenty of famous examples that seem to prove them right. When Uber was expanding into new markets, for example, it often just started running what were essentially illegal taxi services, absorbed the fines as a cost of doing business, and kept going. They were betting that by the time regulators caught up, the company would be too popular to shut down. Rules be damned!

Because of examples like that, I understand why the “rules don’t apply to me” story is appealing. It turns success into an attitude anyone can adopt immediately in order to get ahead. The only problem is that it gets the actual mechanism almost exactly backward, and the clearest way I know to explain why involves a guy jumping over a bar in 1968.

The man who went over the bar backward

If you’ve ever watched the high jump during the Olympics, you’ve probably noticed how weird it looks. Competitors basically launch themselves over the bar backwards in a way that seems almost cartoonishly absurd.

It didn’t used to happen that way. If you watch old footage of the high jump, you’ll see that for most of the sport’s history, athletes went over the bar face-down or feet-first, using techniques with names like the straddle and the western roll. However, at the 1968 Olympics in Mexico City, a lanky engineering student from Oregon named Dick Fosbury went over the bar backward in the now standard way. However, at the time, it seemed crazy. One reporter described it as looking like a guy falling off the back of a truck.

But that craziness was so effective that Fosbury dominated the event and easily won gold. Naturally, before long, every serious high jumper on earth was using the same technique. Today it’s the only technique anyone uses, and it’s called the Fosbury Flop.

The story usually gets told as a triumph of the lone rebel — the weird kid who ignored a century of accepted wisdom, did his own thing, and revolutionized a sport. And while that’s a great story, it’s also not quite what happened.

The part that usually gets left out of the story of Fosbury’s triumphant Olympics is that going over the bar backward was never against the rules. The high jump rulebook didn’t care how you crossed the bar. It only required that you took off from one foot. Backward was always perfectly legal, and Fosbury wasn’t even the first person to think of it. The idea had floated around the sport for years.

So if it was allowed the whole time, why did nobody do it?

Because until Fosbury came along, high jumpers landed in pits of sand and sawdust. And landing on your neck from seven feet up onto packed sand is a fantastic way to end your athletic career… and probably your ability to walk.

Then, in the early 1960s, something changed. Schools and universities started replacing those sand pits with chunky foam matting. And when that happened, landing on your back stopped being dangerous and started being comfortable, which meant a technique that had been legal-but-suicidal for decades suddenly became legal-and-easy.

And the reason I’m explaining all of this isn’t because entrepreneurs need to understand the nuances of high jump. Instead, entrepreneurs need to understand that Fosbury’s success wasn’t an act of rebellion. It was an act of attention.

Fosbury didn’t break a rule, and he didn’t invent a secret move. He noticed that the ground underneath the sport had changed, realized that something previously impossible was now available, and got there before everyone else did.

What Fosbury teaches us about opportunity

The logistical evolution of his sport that Foxbury leveraged reflects a much more important pattern that powers the engine behind most of what we mistake for rule-breaking, and it shows up constantly in the business world.

The rules that govern what you’re allowed to do — laws, regulations, technologies, norms — are shifting all the time. And every time one of them moves, it opens a brief window where something that used to be impossible or illegal or simply too risky becomes viable, and most people haven’t caught up yet. That window is where opportunity lives.

Think about what happened in 2021, when the NCAA changed its rules and college athletes could suddenly get paid for the use of their name, image, and likeness. An entire industry of collectives, marketplaces, and agencies materialized almost immediately. The people who moved first weren’t outlaws flouting some sacred code. They were reading a rule that had just changed and moving faster than everyone still operating under the old one.

The same thing has played out, state by state, with the legalization of marijuana. The opportunity had nothing to do with defying drug laws and everything to do with watching which ones were about to change, then being ready the moment they did.

Even Uber, the supposed poster child for not caring about rules, doesn’t really fit the story people tell. Eating those fines looked like reckless defiance, but it was really a calculated read on where the rules were already heading and a bet that regulators would eventually catch up to a service people had decided they wanted. That’s a very different thing from simply not caring.

Which is why the woman in the TikTok video had it almost perfectly backward.

The people who look like rule-breakers from the outside are usually the ones paying the closest attention to the rules. In fact, they’re paying such close attention that they notice the exact moment a rule shifts and creates a big opportunity. So ignore anyone telling you “the rules are meant to be broken.” Focus, instead, on being the first person to notice when the rules are changing… and be ready to jump.

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