Biking up Vail Mountain, my pedals revolved in lowest gear at a pace that if videoed via Snapchat, recipient viewers might confuse what they watched with lag and a poor Wi-Fi connection. I pulled up the rear employing a distraction mechanism recalled from practice-long conditioning sessions in college: “Tonight, I will be in my bed. Tonight, I will be in my bed,” reciting on repeat. I’d catch up with the group at a stopping point before the next climb where my friend, Brandon, encouraged with an estimate of how much further. I appreciated his intentions, but “I’d rather not know, Brandon.”
Not knowing. Thoughts of not knowing became my new distraction mechanism along the remaining ascent. Still pedaling like a lag, a quote I heard in a podcast from my favorite writer, Ryan Holiday, pedaled it’s way to mind:
You will feel less pressure and less insecure if you just realize that everybody’s winging it. And the people who are pretending that they’re not winging it or are presenting it like it’s all been part of a brilliant plan are either insane or lucky or lying.
I’ve always felt a self-inflicted pressure to know. Certainty is envied and uncertainty evokes worry. If you know, you have it figured out. If you don’t know, you better start figuring it out. At least that became my self-talk.
In high school, the question I feared most was, “Where are you going to college? You need to start figuring that out.” I was quietly envious of friends who knew where they were going. I had to know too. I committed to the first college that recruited me. “Now I know.”
As a college sophomore, the question I feared most was, “What’s your major going to be? You need to start figuring that out.” I was quietly envious of friends who knew what they wanted to study. I had to know too. I declared a major in Economics. “Now I know.”
As a college senior, the questions I feared most were, “What’s next? What career are you going to go into? You need to start figuring that out.” I was quietly envious of friends who knew what was next. I had to know too. “I’m going to law school.” “Now I know.”
As the law school application period approached, the questions I feared most were, “What kind of law? Why do you want to be a lawyer? You need to start figuring that out.” When “I don’t know” continually evoked looks of suspicion, I crafted an answer to earn looks of satisfaction – “I want to be a sports agent. I want to be involved in contract negotiations and help athletes get the money they deserve.” “Now I know.”
What I liked about law school, what it really presented, was a few years removed from fearful questioning. My ego liked the thought of saying, “I’m in law school.” That sounded better than “I don’t know what the f*ck I’m doing.” I never applied to law school. Four years of my life just to appear on track? That scared the sh*t out of me. That I knew.
I graduated college and moved to Perth without doing any research on Australia. Had I, probably first search results would have steered me to Sydney or Melbourne. I went to Sydney. I’ve been to Melbourne, Brisbane, Byron Bay, Bondi, Coogi, Noosa, and Cairns. When I go back to Australia, I’ll take the additional 6-hour flight to Perth.
I left Perth to extinguish a burning desire for a full ski season. I accepted a ski-instructing job at Beaver Creek, a mountain I’d never been to nor heard of. One conversation with someone who has skied in Colorado probably would have steered me to Vail or Aspen. I’ve since skied Vail. I’ve skied Aspen, Breckenridge, Keystone, Steamboat, Heavenly, Squaw Valley, and Park City. I went back for a second season teaching at Beaver Creek.
I don’t think these were some carefully orchestrated backlashes against certainty, though it does admittedly appear to be. There was no premeditation, no brilliant plan, no certainty involved. I was winging it.
When I chose a college to convey certainty, I was unhappy and transferred after a year to a school without visiting. I walked into an unknown and found my great college experience.
When I chose a major to appear decisive, I was unhappy and switched after a year to English. I walked into an unknown and found my obsession for writing.
When I crafted a script for law school, carefully sculpted to relieve pressure, to buy some time, to appear certain, to say “now I know,” I was unhappy to be conveying what felt fabricated. I abandoned that four-year satisfactory answer to embrace uncertainty.
The Stoics call it Amor Fati – a love of fate, making the best out of anything that happens, not forcing but embracing. I like that.
Here I will selfishly seek comfort in another quote (big quote guy). This time from Mark Manson, author of The Subtle Art of Not Giving a F*ck, who says this about life:
It’s not about knowing everything, but becoming more comfortable in not knowing anything.
Or like I always say, When ascending a mountain, knowing where each switchback, steep section, or how much further does my pedals no good. I do know with certainty that’s not quite as ‘transcribe it to a beautiful sunset photo and post it to Pinterest’ as Holiday or Manson’s wisdom, but the foods coming from the same kitchen. I think that’s how that saying goes, but, I don’t know.