I have been a cyclist for almost 30 years now—longer than many of my cycling friends have been alive.

That hobby grew from a life-long quest to be the sort of athlete (and man) my father would respect. My father was a four-sport letterman in high school, captain of the first state championship football team in my home town. He was a small young man, but fierce and the sort of hard worker that made him a coach’s dream. By the time my father graduated high school in the 1950s, he had lost so many of his teeth that his dentist pulled the rest, and my father has had a full set of false teeth since his late teens.

I was never able to be more than a bench warmer on my school basketball teams, a marginally fair golfer, and briefly a triple jumper my senior year of high school. Mostly, though, I joke that I am a “try” athlete—and it is something I cannot let go, despite knowing without qualification that my father loves and respects me in the exact ways I have always wanted. Any perceptions of failure that exist between the two of us are entirely my insecurities.

My cycling life has had three stages—a beginning decade of learning to ride and race at a high level, a middle decade that was interrupted by my doctoral program and included years of mountain biking and a brief venture into running (a couple marathons and a half marathon), and then the most recent decade of yearly high mileage (7,000-10,000 miles per year) and my best performances as a cyclist despite my advancing age (for an athlete).

For more than half of the years of cycling, I have participated in the Assault on Mt. Mitchell, a 102-mile ride from Spartanburg, SC, to the top of Mt. Mitchell, the highest mountain peak east of the Mississippi. I had my best time, 5:57, at 46 and completed the event in the spring of 2013 as 86th out of 1100 starters.

Typically, in large amateur cycling events I place in the top 15% of entrants—and feel pretty good about these accomplishments.

As I sit writing this, I am on a cycling trip in Colorado, about to leave after a few days in Boulder for Frisco to ride the Copper Triangle ride this coming Saturday. The first half of this trip for me has been a brutal lesson in humility.

Although I have visited Colorado Springs several times in the past, this trip resulted in immediate altitude symptoms—a headache, lethargy, and the classic feeling of having the flu. The day after we arrived, we began riding around Boulder, and the symptoms have been pronounced on each ride.

The first ride was in chilly rain, and when the route turned up hill, I watched my two cycling friends ride away into the mist. The second ride headed to Flagstaff Mountain, resulting in yet another ride in rain and cold; but this time as my friends pedaled away from me I simply couldn’t continue up the climb. At the point when the Flagstaff climb turns to what locals call Super Flagstaff, with grades 15-20%, I shouted to one friend I wasn’t going farther up. I coasted back down to an overlook entrance and waited for them to finish the climb and roll my way.

I was angry, disappointed, exhausted, and most of all, embarrassed.

Yesterday, we headed to Estes Park for a 20-mile mountain climb to the highest point (over 12,000 feet) for a through road in the US. I wasn’t looking forward to yet another day of struggling, and possibly bailing out again.

As we neared the 12,000-feet mark, I was still lagging behind the other three riders, and my head ache returned along with dizziness. None of this boded well for over 2.5 hours of climbing at an altitude I had never experienced before.

It took a great deal of arguing with myself, but I finished the ride yesterday, although still slower than my friends. So far, then, this cycling trip to Colorado has been a series of lessons in humility.

And that has led me to think about the lack of humility found among public and political leadership focusing on schools in the US.

Those self-appointed leaders tend to embody a couple of characteristics: little or no experience or expertise in education and unwavering arrogance, an arrogance that they and the media flaunt.

Ben Folds has captured well the failure of such arrogance in his “Bastard”:

The old bastard left his ties and his suit
A brown box, mothballs and bowling shoes
And his opinion so you’d never have to choose
Pretty soon, you’ll be an old bastard too
You get smaller as the world gets big
The more you know you know you don’t know shit
“The Whiz Man” will never fit you like “The Whiz Kid” did

The refrain to this song speaks potentially to those edu-leaders and their arrogance, and thus failure to exhibit humility:

So why you gotta act like you know when you don’t know?
It’s OK if you don’t know everything

I am well past the 10,000-hour mark needed for expertise as a cyclist (popularized by Malcolm Gladwell). I have a great deal of skill and knowledge as a cyclist, although I also have a pretty low genetic ceiling in terms of how I can perform as a cyclist (a ceiling dropping in on me as I grow older each day).

The Cycling Gods and Altitude Gods have spoken loud and clear to me in the last few days. It is my duty to listen.

The list of what public schools need in the US is long and complex, but a great starting point would be lessons in humility for those who have decided they know best when all the evidence suggests otherwise.