Break all the rules you can

Sometimes I forget how nuts I look. My partner and I went backpacking through the Rockies one winter, and the trail ran out. It turned into this thin squiggle alongside a vertical rockface.

He started to turn back. Not me. I hugged the crag and started inching around, jabbing my snow shoes into the frosty ledge. It must’ve been a hundred foot drop if you slipped, but that didn’t matter.

Here’s what did. The trail widened on the other side of the rock. I could see the path. And I wanted to reach the top of this fucking thing.

But my partner stood motionless. “Babe, this doesn’t look safe.” We argued a couple of minutes. Every time I tried to wave him toward me, he freaked out and asked me to “please keep your hands on the rock.”

Finally I gave up and we took another, less impressive route to a lower peak. At least a few times, I called him a coward.

But it’s fine. Because we had sex that night, and I apologized. And we drank hot chocolate.

I’d seen plenty of peaks by then. Despite my disappointment, I felt nice. We were on vacation, after all. We should both enjoy the hiking. Not just me. How selfless. Later, he actually said thanks. Such a sweetheart.

Rock climbing in my early 20s taught me one thing. Don’t fear the fall. Or the fail. Rock climbers fall a thousand times a year. You come to love the thrill of a 12-foot plunge. A bloody finger, the slight chance of death. All that just makes your final accomplishment all the more satisfying.

Sometimes, we climbed without ropes. The professionals call that free-soloing. But we were just college fuckheads. Once, we even climbed up the side of a hill during a hike because it looked easy. Maybe fifty feet.

We camped that night during a severe thunderstorm. Hunkered down in a tent. Lightning. Winds at 60 mph. Better than any rave.

Most of the time, rules keep us safe. But other times, they just hold us back. I’ve broken more rules than I can remember. I’ll do my best to recount the important ones. Breaking rules is good for you. Everyone breaks rules on their way to success.

When the cops showed up, my friends bolted. We’d spent the past hour exploring the ruins of an abandoned asylum. Why? Beats me. I’ve always felt a connection to forbidden, taboo places.

The officer cuffed and loaded me into the back of a patrol car. Trespassing carried a $500 fine. Prison didn’t worry me. The fine did.

Imagine my relief when he let me go with a warning. “If you ever come back here,” he warned, “You’ll spend a weekend in jail and lose your last paycheck. Understand?”

As if. Back then, I barely made $400 a week as a lowly TA.

Inspiration comes from the strangest places. Every visit to some lost, haunted location helped me find a little piece of myself. I’d spent almost a decade sneaking into old prisons, sanatoriums, factories, and haunted houses.

Sometimes I got arrested. Sometimes, I got lucky.

No regrets.

At least, that’s what you hope. Even your worst mistakes should have meaning.

I’m not advising anyone to live recklessly. You should always think through the consequences of your actions.

But sometimes, the risk is worth the reward. I’m not talking financial perks, a raise, a promotion, or Bitcoin. Sure, the same logic applies. But most fulfillment comes with a certain twinge of uncertainty. That girl at the gym you like? You have to risk rejection to ask her out. Whatever goal you’re eyeing, you have to commit if you really want it. You can’t shield yourself from danger and expect joy from life.

There’s this one episode of Star Trek. The best one, in my opinion. The prankster Q allows Captain Picard a chance to travel back in time and “correct” a mistake he made in his youth. Young Picard started a fight with some aliens and (spoiler) got stabbed in the chest. But after he “corrects” the “mistake,” Picard finds his new feature. He never became a captain. He never led any expectations. He just stayed safe. How sad.

Like others, I’ve felt my share of failure. Heartbreak. Shame. Remorse. But you can learn from the most from gut-wrenching mistakes. If I could rewind my life, I wouldn’t change anything. Sure, I wish some things might’ve turned out different. But enough things went right. So why fuck with it?

I’ve recently reached the age when other people start asking me for advice. It’s all the same shit. “Should I do X?” They all get the same answer. “If you feel compelled, then do it.”

Most of them want to know if they should write a novel. Or a memoir. Or if they should pursue a PhD. These have always been bad ideas. But people like me have done them anyway.

It wasn’t a matter of choice.

Big life decisions never require as much thought as you think.

You just have to imagine two scenarios — the best possible outcome, and the worst. If you can accept the latter, then live your dream.

Take drugs. I’ve smoked all the weed I ever cared to, because the worst that could happen was I got arrested. The best outcome happened: I spent a magical weekend with a guy in the woods and lost my virginity in a log cabin. Memories I’ll have when I die. Thanks, weed.

Cocaine? Different story. A handful of friends tried to get me to do coke. Worst scenario: you turn into a babbling lunatic and have a heart attack. Best scenario? You turn into a babbling lunatic and don’t. I’ve studied people on coke. It never looked like much fun.

A teacher once wrote me up for running in the hallway. Such bullshit. She sent me to the main office for hole punches. If you got 5 hole punches on your behavior card in a week, then you missed out on ice cream Friday or something. Anyway, I had three hole punches already.

Running in the hallway carried a sentence of one hole punch.

But the front desk lady didn’t like me. When I handed her my card and said, “I got caught running in the hallway.” Here’s how she responded:

“You mean you were running the hallway when you shouldn’t have been?”

Even at the age of 9, the bullshit wasn’t lost on me. This cross granny didn’t just want to punish me. She wanted to shame me for something that comes natural to most people: running when you need to get somewhere in a hurry. But that was the rule: no running.

It didn’t matter if the hallway was about 50 feet wide, built to accommodate dozens if not hundreds of people making their way from classroom to classroom.

When I was running, this vast hallway was empty.

I’d chosen to run precisely because of this reason. I’d been sent on an errand. I had to be back by a certain time. The errand had taken longer than expected. And I was late. The hallway was empty. The chances of me colliding with another human being or object was….slim.

You see, children can make these kinds of decisions.

So when this angry little woman corrected me, I didn’t respond well. I folded my arms and scowled. “You’re not a teacher,” I said. “Just a secretary. So give me my hole punch so I can go.”

So, three extra hole punches. And a phone call home.

It was Friday. So I definitely missed out on ice cream.

And I also got spanked pretty hard with a paddle. My mom did it right over the bedroom dresser so I could see my face scrunch up in the mirror with each crack. Yeah, parents still beat their kids in the 1990s.

But that changed nothing. I was all too glad to sit on a bench, anticipating my beating, and watch all the other kids lick chocolate off a stick for an hour. Fuckers, I thought. I held my hole punch card like a trophy and smirked to myself. One day, I knew, this would become a great story.