The view of Pike’s Peak from the top of the climb. Credit: Jordan Hayes

My forearms are burning. I open and close my hands a few times, observing the frustrating sensation of having them respond at about half the speed that I’m requesting of them. Over my left shoulder is a spectacular view of Pike’s Peak, far below me a group of climbers – some onlookers, some stealing a moment of shelter in the shade – but the view that’s really capturing my attention is the rock formation six inches in front of my face.

My right hand – and by hand, I mean some portion of a few of my fingers – is gripping onto a rock just barely within my reach. My feet are resting on a natural shelf cut into the mountain, the route above me jutting out towards my torso, pushing me into a backwards-leaning posture that feels, well, about as unnatural as leaning backwards off the edge of a cliff.

It’s my first time sport climbing.

“You need three points of contact with the mountain!” shouts a voice below. “Reach your left hand up, plant your left foot, and pivot!”

I explore fruitlessly for a gripworthy spot for my left hand, though I am able to locate a two inch long, half-a-penny deep ledge about waist high where my left foot is supposed to go. Awesome. My size 13 shoe is better suited for use as a canoe than as a precise fulcrum while cliffhanging.

“I can’t!” I yell down, immediately regretting the words as I feel them leave my lips.

Taking a quick breather in between failed attempts at overtaking the top. Credit: Jordan Hayes

‘I can’t.’ Wow. When was the last time I let myself say that? It’s an outrageous statement, of course, as I’d seen a climber successfully scale the exact same area just moments before – but that knowledge didn’t make it feel any more possible.

My friends probably wouldn’t describe me as a cautious person – I take frequent risks in business without much of a second thought, the level of confidence derived from a track record of success topped off with a healthy dose of delusional naivety. When I pitch a prospective new client, I’m completely and unrealistically confident – the possibility of failure doesn’t enter my mind. Last week, that brazen ignorance landed me a contract with Amazon.com – the biggest client that I could dream of for my auto parts company.

But as I clung to the mountain yesterday afternoon, the prospect of failure lurking just around the corner, I realized just how unfamiliar the fear of failure had become. As a habitual risk-taker, how could that be?

Risk-taking, like all other things in this world, is relative. In 2008, freeclimber Alex Honnold became the first person in the world to climb a 2000 foot face in Yosemite without any sort of rope or safety gear. Most would call him fearless. But are his climbing habits really an accurate indicator of his tolerance for risk? As you approach mastery of your craft, the possibility of failure becomes lower and lower. Though there is no denying that death is a real danger, someone like Alex probably does not experience the terrifying thrill of failure each time he approaches a climb.

Without fear, they say, there can be no courage.

As we get older in life, we have a tendency to specialize – we become experts where we once were novices, growing deep knowledge repositories of narrow subjects. Building on an existing foundation is inherently less risky, as you’re leveraging previous experience and wisdom to propel yourself further into a skill. It’s the path of least resistance, the logical way of adult growth, and it manifests itself in nearly all facets of our lives.

When we’re planning our next move, we search for safety – pursuing choices that mitigate the chance of failure. We take Calculus 2 despite hating Calculus 1, we become a partner at the law firm although we hated being an associate. We’ll wait for someone to show interest in us before we pursue them – looking for any sign of a guaranteed “win” before putting ourselves out there.

Embracing an activity with a high probability of failure is the single most effective way to build character. It’s a gut check and an ego check, a way of being a child again as you approach a challenge knowing that you will likely get some bumps, bruises, and a healthy dose of embarrassment along the way. The late Tai Chi master Cheng Man-Ching called it “investing in loss,” and it’s an incredibly useful tool for disrupting the detrimental pattern of safety in our adult lives.

Take on challenges that will humble you – activities that are outside your area of expertise or outside your comfort zone. Enter a competition that you know you’ll lose, take singing lessons if you’re tone-deaf, learn to snowboard even if you’ll be relegated to the bunny slope while your friends shred double black diamonds.

Though it doesn’t feel that way from the bottom of the ladder, take comfort in knowing that every expert started in the exact same spot: as a beginner.

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And in case you’re wondering – on the final attempt, as my freshly chalked hands gripped the rock tightly and I planted my foot on the ledge, I desperately searched for the next suitable rock to reach for. There are precious few moments to advance to the next position before your grip fails you and you meet the mountain face first once again. A half dozen muscles protested in unison and the seconds ticked by furiously.

Jordan, a fellow climber, poked his head over the top and, for a fleeting moment, I imagined his hand reaching out to help me those last few inches. The hand never came, and I’m glad it didn’t. I made as controlled a movement as my body would allow, I gripped onto whatever I could find, and I clawed my way up over the top.

And in that moment, I was glad to be a beginner.

Here’s me tackling the last obstacle of the climb. Palma non sine pulvere (no victory without struggle). Credit: Jordan Hayes