How to Decide Which Rules to Break: A 3-Step Guide – Brett Kelly

How to Decide Which Rules to Break: A 3-Step Guide

Recently, my good friend and honorary uncle to my kids asked if he could take them skiing. They’d never been and he wanted to teach them. I agreed to drive, but I’m no skier—I would bring my iPad and work at Starbucks down the street while they did their thing.

Per our lunchtime plan, I picked up sandwiches and brought them to the ski resort thing. Parking was horrendous, but I found a spot in the pickup/drop-off lot right near the entrance.

All around me were huge signs telling me unambiguously what would happen if I left my car unattended: I’d get towed away.

Trouble is, there was zero cell service on the mountain and I had no way to alert my friend that I had arrived with lunch. And, since I wasn’t allowed to leave my car to go find my friend and my kids, I was stuck. Standing at my car, I hoped my buddy would realize it was lunchtime and that I might be waiting in the parking lot for him.

Wherein I Get the Stoner’s Permission

After about 20 minutes waiting (with no sign of my buddy), I knew I had to do something.

I looked over to the driveway where I had entered the lot and saw a guy directing traffic. This young buck was straight out of a movie: lanky with bleached hair, snow garb, and a hat cocked to one side. Dude couldn’t have been older than 19.

Carrying the bag of food, I walked over to the guy and explained the situation.

“My buddy has my kids in there and I brought lunch for them. Can I step away from my car for a few minutes or will I get towed?”

His chortle all but confirmed my suspicion that this young fellow was an enthusiastic fan of the ol’ devil’s cabbage.

“Naw, dude. It’s cool. Handle your scandal, bro.”

I thanked him and walked away, heading into the crowded resort in search of my people.

“Handle your scandal…” I had to chuckle at that.

I eventually found my buddy and my kids, delivered the food, and headed back to find my car had not, in fact, been towed. I drove back to Starbucks and got back to work.

Scandal handled.

But this is one of a million experiences I’ve had that got me thinking about rules.

While I can’t swear to it, my firm belief is that a tow truck is rarely dispatched to the pickup/drop-off lot at the ski resort. Putting a 3-foot sign every 15 feet letting folks know what will happen if they leave their cars there is enough.

Many, many of the rules and constraints we encounter in our daily lives are based on this idea:

“If one person breaks the rule, it’s not an issue. The problem comes when everybody breaks the rule.”

The parking lot thing is a perfect example. With 100-ish spots in the lot, one car that’s parked unattended isn’t going to disrupt anything. If the lot is full of unattended cars, then it no longer serves its purpose as a place where you drop your friends off and pick them up.

You can use this to your advantage by making note a three-step process for evaluating a given rule or constraint.

Step 1: Determine Your Level of Idiocy

When driving on the freeway, I generally exceed the speed limit. Not a ton—maybe 5–10mph above what’s posted, assuming I think it’s safe to do so.

Two reasons:

  1. Everybody is pretty much doing the same thing. “Flow of traffic” and all that.
  2. I have a working understanding of the risks.

The faster I drive, the longer it will take me to stop. If I lose control of the car, I’m likely to do a lot more sliding, tipping, and bouncing than if I were going slower.

Most drivers with a few years under their belt can intuit how safe or dangerous a given manner of driving is, even if they can’t explain the physics behind it. All good there.

Contrast that with the now-defunct rules about using electronics on an airplane during takeoff and landing. The avionics engineers and physicists reading this could probably explain why operating an iPhone in this context might be unsafe somehow, but for the rest of us simpletons, it’s a mystery.

Campfire lore usually has folks assuming it was a technical reason. Could the cellular, Bluetooth, and wifi radios in the phones somehow mess with the computers used to control the plane?

Perhaps. 98% of me thought that was a pretty remote possibility, but I don’t understand the first damn thing about airplanes, flying, or the technology driving the whole process. So, I obeyed the rule—because, in that instance, I’m an idiot. Relatively speaking, anyway.

Survey your surrounding context. If a rule or constraint governing your behavior is informed by knowledge your dumb ass obviously lacks, consider complying.

Step 2: Get the Real Reason

If you get past step one, it’s time to sleuth a bit.

Often, a moment’s thought will help you understand why you can’t or shouldn’t do something you want to do.

Sometimes, that reason is complete BS, other times it’s not. That’s what you need to figure out.

Ask the dude or gal behind the counter. Ask Google. Don’t assume.

Often as not—as with the ski resort parking lot example—the rule exists to limit the ass pain of the rule-maker. Or it was handed down because of one jackass who ruined it for everybody—like how we must now remove our shoes during airport security screening because that one a-hole hid a bomb in his shoe that one time. It could also be that a given rule or constraint has just been in use for so long that its survival is due only to inertia.

Whatever the real reason is, do your best to find it. If you can’t find it, your analysis of your own idiocy from step one may be inaccurate.

Oh, and I’m not suggesting you badger anybody or complain about what you believe to be a dumb rule. You may not be a complete idiot in this scenario, but acting like a brat isn’t going to get you anywhere.

Step 3: Avoid, Bend, or Break

I guarantee you that, at some point, somebody said this:

“You can’t get married while skydiving!”

Guess what: not only can you, but apparently it happens rather frequently. There’s a place in Vegas that offers it as a service.

It’s not like a law restricting aerial weddings was repealed. It’s just that most people thought it was a bad idea, for some reason, until some intrepid couple decided to give it a whirl and it worked out.

The first couple to do this broke the “rule.”

Recently, a friend of mine went into a clothing store to buy a pair of pants. When he got to the cash register, the lady helping him out told him his total would be $60.

He asked, “can I have them for $50?”

She thought about it for a minute.

“Ok, but don’t go talking about it.”

He was able to bend the rule, with help. And I guess he broke the one about not talking about it.

I read a story once about an engineer at Google who some student loan debt and wasn’t interested in ponying up the absurd amount of money it would cost him to get an apartment in San Francisco.

So what did he do? He lived in a truck. A “box truck,” the kind you’d see hauling furniture or appliances for delivery.

His monthly cost was $121 (insurance for the truck). He parked it at Google and charged all of his devices at work during the day. And he made huge strides toward paying down his debt in a very short time.

He avoided the “rule” altogether.

Bottom line is this:

  • You can turn an extension cord into a clothesline.
  • You can use a screwdriver to open a beer.
  • You can build the next Facebook on a $500 piece of crap laptop.

You just have to get creative—and perhaps a bit bold—in pursuing the outcome you’re looking for. Chances are, there are fewer impediments and obstacles than you think.

Some Rules are Real

I’m not telling you to break every rule you come across. Many of them are in place for a good reason: your safety, the safety of others, and so forth. Also, breaking all of the rules doesn’t make you some kind of maverick—it makes you a dick.

But what I am telling you is not to assume that rules and constraints aren’t negotiable—because a whole lot of them are.

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