Risking Regret

Just north of Moab, Utah, a sandstone fin called The Lion’s Back rises about three hundred feet above the blowsand of the desert floor. It’s closed to the public now, because the public can’t be allowed to have nice things, but it used to be a famous Jeep trail. If you are a fan of scary youtube videos, you’ve probably seen the famous crash that happened there years ago (don’t worry, no one was hurt died). But back in the 1980’s, before the Jeepers really discovered it, it was just a big rock up behind the city dump.

When I was 14 I jumped off the top of it.

lions_back

You Wait What, Off The What of the What Now?

Oh, relax. I had a rope. I even had responsible adult supervision! Well, I had adult supervision at any rate.

My mom was pretty overprotective of me, and when my friend Kenn called and said “A big group of boys and girls from scouts and church are going rappelling today, do you want to come?” I was very excited but also pretty sure I wouldn’t be allowed to go. I remember asking my parents, and my mother making her “worried disapproval” face. But then Dad turned to her and said,

“If you don’t let him go now, when will you?”

Two hours later I was up past the dump near Lion’s Back learning how to rappel.

They chose a small fin next to Lion’s Back and set up practice stations for us. The first jump was maybe five feet high: just high enough to learn how to lean back into the harness. The next was ten or twelve feet: here we learned to work our way down the face. The final station was thirty feet high, enough to get a couple really good bounces off the rock as you came down the rope.

We had arrived in late afternoon, and there were enough of us there that by the time I had tried all three rappelling stations, the sun was starting to set. I figured that was the end of the day, and that it had been a lot of fun. I was really happy I’d come, and I really didn’t see what Mom had to worry about.

“All right,” hollered Kim, our rappelling instructor. “We’re running out of light, so anybody that wants to jump Lion’s Back, we’re going right now.”

Maybe Mom Was Right

I turned around from the tiny fin we had been practicing on. The Lion’s Back went straight up in front of me over 300 feet. I had a sudden attack of vertigo and I wasn’t even looking down. I remember thinking, “I’ll let the other kids go, and if it looks okay, then maybe I’ll try it.”

I think a bunch of us were thinking the same thing, and had the same looks on our faces, because Kim then said “It’s a half-hour hike to the top, and we only got time for one jump, so if you ain’t coming right now, you ain’t coming.”

I knew this was my one chance. I looked at the cliff again. So high, so impossibly, terribly high. The only thing a rational human could do from up there was fall instantly to their death. I mean, obviously. I sighed, and decided not to go, and looked down at my feet.

But then something happened. A tiny little voice in the back of my head piped up and said,

“If you don’t do this right now, you will regret not doing this for the rest. of. your. life.”

I looked back up at the cliff. Yep, still terrifying. But I looked over at Kim and said “I’m coming.”

Fear Is Intense, But Regret Is Forever

By the time we got to the top and anchored our rope, the sun was low over the horizon, starting to turn the desert flame red. Being the chivalrous young men that we were, we let the girls jump first. It was a long drop, and it took each person maybe ten minutes to get down the rope and the next person to get hooked in. By the time the boys could go, the sun was starting to dip beneath the horizon, bathing us in dusk. I was about third from the last, so as jump after jump happened in front of me, dusk came and went, and night settled upon us.

Remember, this was when Moab was a boom town gone bust: there was no light pollution. There was no moonlight to jump by because it was very close to New Moon, but just by starlight alone I could see for miles and miles, the once-red sandstone fins now blue and black but still clearly visible, marching off into the high desert as far as the eye could see.

I figured I could maybe just not jump and hike back down. Since it was dark and all, obviously I wouldn’t be expected to jump. But still that voice told me, convincingly, of the lifetime of regret I would have if I chickened out.

Kim had been bantering with us the whole time, making jokes about how it was such a lovely night for some rappelling, that sort of thing. And suddenly it was my turn. Kim could tell I was terrified, and was about to back out. He smiled kindly, and said in his soft cowboy drawl, “David, me’n your dad used to work at Rio together. We was on the mine rescue team together, and I took him rappelling, too. We’ve jumped some pretty crazy stuff, me’n your dad. But he ain’t never done a night jump. If you tell him you walked back down the trail with me, he’ll understand.”

He could have appealed to my pride, told me how jealous my dad would be if I jumped. He could have urged me to jump, pressuring me a dozen different ways. But all he did was show me what the choice to give up looked like, and reassure me that it would be okay. And it’s taken me nearly thirty years to figure out just how wise his words were: he put the full weight of the decision and the consequences on me, and took the fear away from the decision itself. This was exactly what I needed.

“I’ll never forgive myself,” I said as I straddled the rope.

Kim grinned from ear to ear as he started the safety check. “You’re right,” he said to me quietly. “You never would have. But now… here you are instead.”

Owning Choices Is The Only Way To Own Consequences

The rappelling rig was a friction-stop rig, which meant that to stop, all you had to do was pull down on the loose end of the rope. Unfortunately, this meant that for a stick-thin, 100-pound teenage boy, just the weight of 300 feet of rope hanging down from me was enough to lock up the rig. Kim laughed. “You’re literally gonna have to haul the rope up and pull yourself down the first twenty or thirty feet. It’s okay. Just start walking backwards, and remember not to sit down, just lean back.”

I hauled up on the rope, and it started letting me inch backwards over the edge. For the first twenty feet or so the slickrock curved away, and I was unable to resist the urge to keep my torso vertical. My descent became more and more difficult as my body slowly bent into a sitting position. Above me and now out of sight atop the fin, Kim called down: “David! Lean back!”

I leaned back.

Imagine for a minute that you are not leaning against a mountain, but standing on a wide, flat sandstone floor. Behind you, hundreds of feet away, the desert floor rises like a wall. People are walking around on the wall and if you could turn around, all you would see is the tops of their heads. But you can’t turn around. You can only stand there, hanging in free space, staring at what is directly in front of you:

Infinity.

The stars went on forever. The Milky Way blazed as brightly across the sky as I’ve ever seen. Outside the band marking our galaxy, blue-white dots pierced the utter blackness. And in the gaps between those stars, the inky void of space went on and on to eternity.

There was no up or down to it, just infinite thereness, right in front of me. I stared, openmouthed, at the night sky I had looked at thousands of times already… but somehow, never, ever, actually seen. It spread out before me with a beauty that still, thirty years later, takes my breath away.

And Owning Bad Consequences Is Easier When You Owned The Choice

The sound of a titanium anchor piton snapping is very distinct. To this very day, that single, sharp Tink!, so quiet yet somehow louder than a rifle shot, followed by the gentle feeling of weightlessness as the sandstone began to fly up past my feet, will always be a thing that never actually happened because gotcha.

In reality, I rappelled down Lion’s Back in fine form, had a blast, and formed a memory that will burn bright in my mind until I die (or get Alzheimer’s as karmic retribution for the previous paragraph). That day I swore to never back away from a choice if it would leave me with a lifetime of regret.

And I’ve had to own a lot of consequences as a result. I’ve made bad decisions. I’ve made bad calls. I’ve made bad estimates, done the wrong work, shipped the wrong product at the wrong time to the wrong people. I have permanently screwed up the lives of a few people. I have deeply hurt many others. And I have offended so many people that I’ve lost count. All because I made a choice and took a risk that didn’t work out. And you know what? I don’t feel good about any of those consequences.

But I don’t feel ashamed of the choices. I made the best call I could at the time with the knowledge and abilities I had. Don’t get me wrong–sometimes it takes me a long time to forgive myself when I say or do something hurtful or ignorant or blithe or just plain dumb. But it’s so much easier than forgiving myself for not making a choice and choosing to own it.

Of course I’m only talking about the bad choices I’ve made here. I’ve made lots of good ones, too, and owning the choice is the reason I don’t feel guilty or ashamed that I get to have the nice consequences. There are lots of great things that happen to me on accident, and sometimes I even feel good about them. But sometimes I was just in the right place at the right time with the right skin color or nationality or gender. I can accept those and appreciate those and be grateful for those, but I can’t really own those. And that’s what I’m talking about here: the kinds of choices you can own, and owning them, and owning the risk of choosing–regardless of which side of the choice you took. That’s how you own the consequences.

You Never Regret Taking The Risk

I want to clarify that sometimes the risk is to take the safe path instead of the path everyone expects you to take. I’m not talking about being reckless, or risking more than you can afford, or making a decision before you need to without gathering the information that you need. That’s knowingly making the wrong decision, and there’s no prize for that. That’s stupid at best, and evil at worst. When I say “taking the risk” I mean studying out the odds, calculating the costs of failure, and deciding if the decision is important enough to get wrong.

So you know the kind of risk I mean. The kind where you have the information you need, you know what success could look like, and you know what failure could look like, and you know exactly what living another day without choosing looks like. That decision. THAT risk.

I have never regretted taking that risk, success or fail.

Of course I don’t mean I’ve never regretted a bad decision. But having the chance to make that decision, and thinking I had enough of the right data, and then making the choice–taking the risk–to the best of my ability? Never. Not once. I’ve never cared for the question “what would you do if you knew you couldn’t fail?” It doesn’t motivate me because I can’t know that I can or cannot fail. But Brené Brown rephrased that question into something so much more beautiful that I now keep it on a post-it on my monitor: “What’s worth doing even if I fail?”

That’s the kind of risk I’m talking about here.

I just tried to think of the dumbest risk I’ve ever taken and I ended up spending over an hour writing and deleting and starting over with just the things I’ve failed at this month. I could be the poster child for failure. Not just because I’ve failed so much, so hard and so often, but because I would also look hilarious on that poster.

So What’s With All This Regret And Risk Stuff?

Dumb choices are not the enemy. Big risks are not the enemy. Crazy failures are not the enemy.

Paralysis is the real enemy here.

If you have a choice in front of you, and you don’t want to make it, there’s a hundred things I could say to you. I could remind you that every day you don’t decide, you slide closer to being stuck with the default choice. I could point out that success would be just so awesome. I could say that you miss 100% of the shots you don’t take.

But I’m not going to. I want you to look at that choice, and look at that failure. Just look for a moment. Look at walking down that mountain instead of jumping off of it. And remember: We’ll understand. Stop being afraid of that walk. If you can own that side of the choice, you’re halfway to owning the decision, and owning the risk.

And if it’s a risk that makes sense–I remind you again that I jumped off with a rope–maybe you can let yourself own that, too.

You might regret the consequences. But you’ll never regret taking the risk.

What’s worth doing even if you fail?

How long will you regret it if you don’t even try?

–David

P.S. I’m still writing the Job Replacement Guide, and this post was definitely inspired by my recent research. If there was one thing I could magically place in the book, it would be something that would wave a magic wand and help you get out of your paralysis. Whether you need to network with people you’re afraid of or ask a potential employer to negotiate your salary when you’re currently unemployed, or just put “I enjoy creating abominations of nature” in the interests section of your resumé (join the mailing right now if you want to hear the true story behind that quote, by the way, because it’s a story too good to not include in the book and I’m telling it on the mailing list today or tomorrow.)

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The Job Replacement Guide

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2 thoughts on “Risking Regret

  1. lalanikki

    Just wanted to leave a note that this post really spoke to me. I found your blog by accident Googling something about Ruby, and checked out this post and some others as well. I’m hooked now. Thanks for putting your work out here.

    Reply

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