Misery Loves Jackassery

“When a jackass flies, no one asks how far or how fast. When a jackass flies, people stand amazed.” –Tim Cahill

My little brother David has a recipe for perfect adventures. Principally, any adventure worth having, any adventure worth talking about, needs healthy percentages of both misery and jackassery. 

Misery is easy to identify. You’re miserable. Cold, hot, tired, wired, thirsty, bleeding. Come, Death, and welcome. You may find yourself bargaining with God, muttering oaths against yourself, or calling for your mother. Misery will find you if you’re committed to doing dangerous things outdoors. 

David, age 17: When a jackass flies…

Jackassery is a bit more elusive. It involves creating or doing something ridiculous in the midst of your dangerous activity. It’s not strictly for idiots: jackassery requires vision and improvisation. Don’t have a piece of essential equipment for your ridiculous idea? Who cares? Let’s do this!

David is annoyingly good at perfect adventures. By the time he was sixteen, I’d witnessed several of these. He turned a rainy weekend of beach-camping into a quest to make a perfect 40-foot rope swing out of flotsam. It remains the best swing I’ve ever been on. Another time he paused during a terrifying ascent of a remote Olympic peak to build a snow-slide into a glacial lake. It was a technical barefoot climb to the take-off point. His descent was executed in boxer shorts accessorized with an ice-ax. 

So in the spring of my 20th year, it was natural to turn to my brother for help. I was miserable. I had a broken heart and a black eye from my first big breakup. The guy put his fist into my face, which cracked my left maxilla and gave me a prize-winning shiner. I topped the look with a helmet and decided to take David’s advice and ride my bike across North America. He, of course, came along. 

For the first weeks of pedaling, I was too self-absorbed to appreciate the salve of my teen brother’s cheerful jackassery. But he soon won me over. He even shared his coveted Walkman, a gesture so touching I dared not criticize Zeppelin and Joe Walsh, the only two tapes he had. We rode side-by-side day after day on the wide shoulder of Canadian highways, an earphone each, the cord tight-roped between our helmets. It was good for pacing. The earphone would pop out if I fell behind. It was also good for my spirit. Somehow, joining my brother’s misery-loving jackass team – choosing to cross Alberta and Saskatchewan by pedaling 100 miles a day in 100-degree heat while yoked to “Life’s Been Good to Me” in mono on a Walkman with failing batteries – was an excellent cure. 

There must be some universal truth to my brother’s way of mitigating misery, because a few years after this bike trip someone handed me an essay by Tim Cahill in which he eloquently explains the “Tomfoolery Factor.” It reads like a how-to for David’s perfect adventures. 

Cue the metal at the Pandemic Disco

Fast forward thirty years. I’d become the de facto leader of a popular Tuesday night mountain bike ride. I still sported an occasional black eye, but from crashes not personal drama. A loose group of a dozen MTB devotees had quadrupled in just a few years. Locals and bike shops pointed people our way, saying “They’ll take care of you at the Tuesday night ride.” And we did. I’d give a short welcome and safety talk, then we rode in smaller groups based on speed and ability. Afterward, we reconvened for tailgating, true tailgating: when you’re too dirty, smelly, or bloody for even a food truck.

As these weekly rides grew, I still enjoyed them, though they didn’t make my brother’s cut for adventures worth talking about. Increasingly, they’d become less challenge and more crisis management. I could ride hard other nights of the week, so my Tuesdays became about helping people, like riders who hadn’t been on singletrack in 10 years or couples twinning for the first time on shiny new bikes. I got good at trailside fixes. Someone dubbed my group “tourist pace.” 

Enter our state’s Covid lockdown in the spring of 2020, a brand new flavor of misery. Goodbye, Tuesday nights. Goodbye, tailgating and group rides. Goodbye, poker runs, tours, enduros, fondos, and grinders. A few souls were going solo, fumbling with virtual race apps or Strava and waving uncertainly at each other from opposite ends of the parking area. I missed everyone, including the tourists. The isolation was agony. 

A few weeks into the lockdown, I got a text from a Tuesday nighter, a fast young guy I didn’t know well: “I’m going crazy. Who’s riding?” Me! Me! Let’s go! 

And so began a tiny, unlikely, unofficial weekly mountain bike ride, mostly that guy and his friends. There were some unspoken rules: No talking about politics or pandemic, and no cancelling for weather unless you’re a wuss. So we rode in downpours and when the trails were clogged with slush. We were determined to exchange one sort of misery for another. Our rides were definitely not tourist pace. And probably not safety-first. We tried ridiculous stunts in the dark, as though filming an episode of Friday Fails. I made ridiculous soundtracks, like Mastodon’s “Blood and Thunder” paired with Frozen’s “Let It Go.” The tailgating turned ridiculously gourmet.

Those rides were by far the best part of my pandemic, a perfect little adventure every week with bikers who have become true friends. I realize now that my brother’s formula depends on something I too-often ignore. Misery and ridiculousness aren’t enough. A perfect adventure also requires camaraderie. Someone to say, “Let’s ditch the bikes and climb the water tower” or “You could so huck those stairs.”  

How lucky am I that my little brother considers me his best friend? Or that a group of young riders invited someone their mom’s age into the hijinks? Like so much in life, perfect adventure is not really about where you go or what you do. It’s about who you’re willing to include. 

This piece and many, many others made possible by Shimano North America.

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