Rule Breakers Have More Fun And 10 Other Reasons To Cultivate Your Inner Rebel

Rules present a dichotomy. Without them, the systems we rely upon can become chaotic. Followed perfectly, however, systems can become stagnant, stale and boring.

I’m anti-stale, stagnant and boring. I like to mix things up a bit; cross the line. And for better or worse, I’ve been more than rewarded for it. So with that backdrop, here are some actually sound reasons for selectively fracturing a rule or two now and again:

1. Rules are established either to level the playing field, or to tilt it.
2. Given 1, odds are you didn’t make the rules, so that field, as it were, isn’t your field.
3. Level playing fields are boring. And if they’re tilted, I want them tilted in my direction.
4. People in power are the ones who create rules, and they’re to protect the status quo.
5. Rules evolve. And that evolution is driven by people who break the rules.
6. Rules are based on someone else’s theory of what’s best, in what situation, which may or may not correspond to yours.
7. Rules are written with language and will therefore always be subject to interpretation.
8. Too many rules needlessly complicate life, and far too often the way people deal with that one guy who just has to take things too far is to make everyone suffer under new rules.
9. Rules are, by their nature, approximations; one-size-fits-all pseudo-solutions to complex problems.
10. Most rules are better off as occasional guidelines, anyway.

Being Willing To Break The Rules Means You Have To Accept The Consequences

I’m not advocating for rule-breakage as a way of being in the world…that would mean creating a rule for oneself that says break all other rules, and sometimes it’s best to follow them. The issues with rule-breaking as one’s default setting pertain to the costs involved with undertaking effort to comply with something that doesn’t apply in a particular instance. In such a case, one has a choice to make, and as a rule breaker, one must accept the consequences, should the risks come to bear. That’s part of the deal.

But there’s an equation involved. Those consequences must be weighed in the context of the likelihood of getting caught, and the benefit of the breakage. That benefit is highly subjective.

Everyone Hates Self-Appointed Hall Monitors

There are some people, a great many, in fact, who think rules should be followed because they are there. I once saw a motorcyclist riding safely, though ‘illegally,’ on the shoulder of the highway, as the Houstonians who were ‘legally’ in the roadway had decided it was a parking lot for the time being and were going exactly nowhere. One motorist decided the motorcyclist was causing so much harm by passing them, that he was going to play hall monitor for everyone else. He pulled his car out into the shoulder (also possibly illegal) and attempted to block the motorcyclist. The guy on the bike stopped, said a few words to the guy in the car, then pulled out a pistol and shot out both the guy’s passenger side tires, put the gun away and went around him. Play stupid games, win stupid prizes. I still want to high five that guy.

Breaking Rules When It Harms No One

In creating too many rules, trying to handle every conceivable scenario, we muck up the works for everyone else. It really helps to be able to think your way around them. Ask yourself, ‘will anyone be harmed if I break this rule in this circumstance?’ If the answer is no (and usually it is) then you have to look at whether you’re going to have a likely consequence, weigh that consequence times the likelihood of a negative outcome, and then you have to evaluate your subjective notion of the benefit of going ahead. And that’s the tricky part.

I once crossed an empty downtown street against a ‘don’t walk’ sign as others waited at the corner for the sign’s blessed permission. A police officer yelled at me ‘wait for the sign, please.’ I looked back and said ‘it’s not the signs that get you…it’s the cars.’ He laughed, and as such, lost the right to do anything further, in accordance with the rules of dealing with police.

Sometimes It’s Better To Not Break The Rules

I see some of the absolute stupidest rules posted at stop lights. ‘No right turn on red’ is one of my favorites. There is never a reason not to turn right on red, as long as you employ good judgment. Too many times, someone didn’t, so the overlords decided this would be best for everyone. No, thanks. But then there are cameras at many intersections now, so that they can discover you in having committed your heinous crime, track you down and make you pay money to their employer. And this is where things get tricky vis a vis your subjective valuation of proceeding. To me, it’s extremely valuable to not be constrained by others’ idiocy; so I take measures most won’t. Usually, however, I just wait it out and find something to enjoy about the moment.

More Rules Won’t Work Unless We Address The Underlying Incentives

In my former career in finance, we had some of the most restrictive and cumbersome rules of any industry. I read once that only Nuclear power was more tightly regulated; and yet, we still had Bernie Madoff, we had Enron, we had Tyco and we had Worldcom. We had Barings Bank and we had Long Term Capital Management. Some of the smartest people in the world work in that industry, and they’re not going to be contained by easily-circumvented rules when their incentives to break them remain. Just wait until AI-powered traders begin layering and spoofing order books as a study in game theory. That’s how we find equilibria.

Cultivate Your Inner Rebel

There is still order when rules can be selectively broken. In fact, that’s what drives the evolution of the rules. And it’s ok to let your inner rebel come out on occasion, whether in business, driving around or just tweaking Google’s impossible-to-comply-with terms of service. You know who you are. Who dares doesn’t win every time, but fortune does favor the bold.