The Jester Precedes the King

In 2014, I made a critical error that haunts me – I didn’t do a local cyclocross race.

Both of my roommates were doing it. I had the money for the entry fee. I even had a cyclocross bike with Di2 (don’t ask how I swung that one on 30k/yr. Hint – shark loans)! Unlike now, I didn’t have kids to take care of, a dog to walk, or a lawn, so I had the most precious commodity of all – time.

But I skipped it. Why didn't I do it?

I’d never done a cyclocross race before. Back in ’14, I was roadie on a mission to go Pro, and my race results progression was promising enough to nurture that delusion. My athletic identity slowly calcified as a Road racer, and I was intent on following the traditional arc of a road racer in the fall after the race season was over- closing down the bars and eating whatever I wanted.

My roommates were also roadies, but neither were as interested in woofing beers as they were getting faster. At that time, online training forums began to buzz with what most road cyclists find self-evident now – Racing cyclocross makes you can animal on the Road. See Mathieu Van der Poel, Wout Van Aert, Tim Pidock, etc, etc.

So while I nursed hangover after hangover and chased a girl, they diligently ate salad, rejected my happy hour invitations, and spent the weekends getting destroyed by 97 pound 13-year-olds who started riding in the womb and could do backflips on the bike.

At first, I found this amusing. They’d come back from cyclocross races poorer, disheartened, and humiliated. While they sat around the house nursing their egos back to life, I regaled them with my debauchery from the night before.

After about a month of this, my amusement faded. They started doing better. They weren’t exactly blowing the fields away, but they were suddenly competitive because they were taking corners better, j-hopping over barriers, and their top-end power increased.

I, on the other hand, was going backward. My skills, if anything, had gotten worse. My power regressed because I wasn’t training as much, and I was constantly poisoning myself. The late-night raids at the local-calzone shop had finally overwhelmed my metabolism, and my medium bibs started to get too tight for wearing in public.

Still, I didn’t see any cause for alarm. Fall turned to winter, and training for the next season started in earnest. I cleaned up my act a little with that girl I chased by switching out less physically demanding activities like day-drinking for dates. My roommates finished out the cross-season, took a little break, and started mashing the cranks again with a vengeance for 2014.

When the roads started to clear in Boulder, we started riding outside together. Immediately, I noticed a sudden change in the way they rode. They always gapped me in corners. They braked less in general. When coming across random obstacles like curbs, they would jump it instead of clipping out of their bike.

And that was just on pavement. If we ventured off onto any mixed surface, this advantage magnified. To keep up with them on a relatively tame Z2 ride through gravel roads or tame single track, I had to throw down large surges to make up for the ground I lost, picking lines and negotiating corners.

I’m not sure how much they noticed these differences in our technical riding ability, but I did, and I knew precisely why they were suddenly superior bike handlers – cyclocross.

Unfortunately, the benefits to cyclocross to their riding didn’t end there. As we started to show up for group rides, the pattern of soul-crushing accelerations, echelons, and technical group riding left me shattered and dropped early. At the same time, they quickly closed gaps, found drafts, and slipped into the perfect position among the peloton.

Like any good bike racer, I processed these staggering disparities in performance with as much denial as possible. I figured my handling would come around, the acceleration I lacked would improve, and eventually, I’d feel comfortable riding in the middle of a pack pinned between two people’s handlebars.

I never did.

I mean, sure, I improved my acceleration. I got slightly better at braking less, sitting in a peloton, and generally steering my bike, but seven years later, I still haven’t achieved the same level of comfort on the bike as they did in three months. 

Yes, this deeply embarrasses me, and like any good bike racer, I harbor enormous reserves of self-loathing and certainty that my shortcomings and failures are unique. The truth, however, is that my weakness isn’t unusual specifically or generally – it’s ordinary.

Many cyclists’ progression stalls because of identity foreclosure – or the rigid formation of their identity not just as a cyclist but also as a particular type of cyclist. e.g., I’m a roadie, I’m ‘cross racer, I’m a gravel racer, I’m a MTBer, I’m a Trackie. Hell, their identity even forecloses within cycling disciplines into a particular type of racing format, e.g., I’m a Climber, I’m a Crit racer, I’m a Time trialist, etc.

Why is this a problem?

If you’re reading this and noticing that identity foreclosure has parallels in other domains of life, good – you’re awake. Widely shared life patterns amongst people eventually make their way into stories and manifest as characters who exhibit the characteristics of this pattern. Smart people call these characters archetypes, which is a typical example of a person or thing.

The pertinent archetype here is the Jester. In numerous story arcs, the common moral of the story is that the archetype of the Jester precedes the archetype of the King.


If you want to master something, you need to be willing to be humiliated first.

Anyone who tries something new is awful at it. Whether it’s a bike race, playing the piano, learning a new language – the beginning is ugly. Even ‘talented’ individuals look like a clown.

But here’s the thing, if you can endure humiliation and continue learning the new skill, you’ll improve quickly. You’ll go from embarrassing to bad, bad to OK, OK to average, and then maybe even average to good.

I could have continued in that progression and ended at ‘world-class,’ but attaining that level of mastery is both unlikely and unnecessary. Instead, aspire to ‘good.’

Why is trying to achieve ‘good’ better than ‘world-class’?

The reason? Most people are only good at a few things because they’re afraid of being humiliated in a new thing. By the time most people hit their mid-20s, most people’s identities have completely foreclosed, and they’re reluctant to invest time and energy into something new because they know humiliation is inevitable.

Fearing humiliation isn’t the only thing that prevents us from trying new things – social media is another culprit. Unfortunately, most of what we see on screens surfaces other’s highlight reels and complete outliers in a given activity, so we often frame our competence in a skill or activity not against the good but in contrast to world-class. Consequently, we misperceive the investment required to progress from bad to good.

Taken together, fearing humiliation and misperceiving the effort required to do new things causes most people to stop trying anything new, which isn’t just bad for your development as a bike racer (or as a person); it’s fatal.

In effect, you’re letting a month or two of embarrassment in a new skill prevent you from enjoying a lifetime of being good in another skill. Remember my example? 2014 was seven years ago, and here I am in 2021, still puckering when I have to jump a curb and reflexively grabbing handfuls of the brake when I don’t need to.


But consider If I smoked cigarettes and told you not to because they’re unhealthy, I might be a hypocrite, but I’m still right.

Besides, this year, I’m changing that. I’m going to do some cross races, and instead of pretending I’m not doing them, I’ll lean into the humiliation and loudly broadcast my failures.

In parting, it’s worth remembering this hack about humiliation – it’s funnier than success. People fall asleep when you tell them about the races you won. They die laughing when they hear how you face-planted into the sandpit during your first cyclocross race while a 12-year-old passed you and called you a clown. Embrace the humiliation

the Weekly grav'

Say no to slow!

Reader questions, stories, and guaranteed laughs every Thursday.