Five School Leadership Lessons I Learned from the Seat of My Bicycle

"Only those who are willing to go too far will find out how far one can go." –T.S. Eliot

The leadership benefits that students derive from exploring their passions and building proficiency are well known and much celebrated. This is true for kids who excel in athletics, the arts, and academics. Mihaly Csíkszentmihályi describes the phenomenon of getting lost in one’s work as experiencing a state of “flow.” Each of us can likely identify specific children whose lives were transformed by the lessons they gained on the court, in the field, on the trail, or in the studio. Teamwork, cooperation, perseverance, the list goes on.
In addition, much has been written in recent years on the pedagogical value of failure and risk-taking. What about educators themselves, though? What can we learn about leading schools from our own experiences exploring our passions beyond the workplace?
Like so many others, I learned to ride a bike as a young child, but it was not until I reached middle age that I was introduced to endurance cycling. Instantly, I was hooked. I was initially drawn to this activity as an escape from the demands of both parenting young children and a high-pressure job, but also for the inherent physical and emotional benefits it provided. I was surprised, however, by how much I learned about myself and effective school leadership in the process. What follows are five lessons I’ve learned over the years from the seat of my bicycle.
1.     Set High Goals
In 2007, I discovered a form of ultra-distance cycling known as randonneuring, which involves participating in organized events of distances that at one time struck me as utterly incomprehensible. How could someone possibly ride a bicycle for 200, 300, 500 miles at a stretch? Through the night? Without stopping for more than a few short breaks? Curious, I set off to answer these questions and discovered over time that we are capable of far more than we realize as both athletes and leaders.
As a cyclist, I learned to manage extreme distances by mentally dividing individual rides into smaller segments and focusing on completing each one in succession. In other words, a ride of 375 miles can be mentally subdivided into seven 54-mile rides. The secret is to focus on the section of the ride you are currently completing, while not thinking about what comes next. This compartmentalization makes it possible to be fully attentive to and successful in the present while not becoming overwhelmed by the volume of road that lies ahead.
As a division head, I took inspiration from this experience to manage the tremendous volume of tasks I found in school. The hundreds of student reports to read, the countless 12-hour days, and the endless cycle of meetings all became not only manageable, but also enjoyable when I learned to focus more deliberately on the components rather than the totality of the experience. Leaders who remember this will be surprised by how much they can achieve.
2.     Pace Yourself
Anyone who works in schools knows that getting from September to June feels more like a marathon than a sprint. As in a marathon, success comes from careful and deliberate pacing rather than speed alone. Those who maintain stores of energy in reserve are far more likely to achieve their goals than those who shoot out of the starting block as if the race only lasts several minutes. Endurance training requires patience and foresight as well as an understanding that, with brief periods of rest and recovery, it’s possible to get back into the race and succeed.
As a randonneur, I remember times when I have been so tired, depleted, and sore that riding my bicycle one more mile seemed utterly impossible. At several low points during the 750-mile Paris-Brest-Paris event, for instance, I was convinced that failure was the only option and began doubting my abilities with each rotation of the cranks. After a series of brief stops to refuel and to sleep, however, I was able to return to this challenge with renewed energy and determination as if I had been magically granted a new set of legs.
As Tony Schwartz and his team at The Energy Project argue so persuasively,
leaders who are attuned to their own energy needs are far better positioned to address the dynamic challenges in their work. Taking frequent breaks, eating properly, and getting enough sleep all pay dramatic dividends over the long term. The techniques I’ve developed to enable me to complete endurance events successfully have been readily transferable to my work in schools.
3.     Solve Problems by NOT Thinking About Them
A central leadership paradox involves problem-solving. Why is it that the best solutions often come to us when we’re not trying to solve a problem directly? How often do we find our minds running down familiar tracks when we’re searching for solutions to complex problems? Sometimes, the best way to resolve this conundrum is to step away from the issue completely. Endurance cycling has provided me with a way to do this that is both productive and conducive to deep thinking and reflection.
Since preparing for endurance events requires significant training, many cyclists commute to work each day by bicycle to add volume while also accomplishing the necessary task of transportation.
The benefits of bike commuting are myriad, but this practice provides an especially good way to mentally prepare for the work day and decompress from it afterwards. Because cycling demands one’s full attention, it has a way of pushing the problem-solving part of the brain into creative territory. In other words, while focusing on the immediate demands of safety and navigation, it’s impossible to perseverate on other topics for very long. While the mind is at rest, it is free to make creative associations. Endurance cycling has provided me with countless hours of generative thinking and planning time. In fact, many of my better ideas over the years have come to me while riding.
4.     Sweat the Small Stuff
In his best-selling book, Richard Carlson argued that we shouldn’t “sweat the small stuff,” but endurance athletes (and good leaders) understand that by noticing and solving small problems before they become larger ones, we can eliminate a great deal of suffering and possible disaster. Long-distance cyclists need to engage certain muscles and organs in repetitive motions over significant periods of time in ways that can easily lead to blisters, sore muscles, intestinal distress and more. A slight irritation over a short distance has the potential to become debilitating if left unaddressed.
While it’s tempting to ignore small issues in the hope that they disappear, I soon discovered that successful randonneurs attended to minor issues before they became bigger problems. Time spent stretching, eating, resting, or investigating an odd noise coming from some corner of the bicycle is often more than made up for by not having to quit when the going gets rough. Many, sadly, learn this lesson the hard way by having to quit a race or abandon a challenge because they didn’t pay close enough attention to the warning signs.
Similarly, attentive school leaders are always on the lookout for small signs that something may not be quite right with the students, teachers, parents, and programs with which they work. By investigating and addressing small issues, we protect others and ourselves from the snowballing effect that often occurs when problems grow and become more serious. Taking the time to adjust and repair small issues is much more effective over the long term than trying to fix a situation that has completely gone off the rails as a result of benign neglect. 
5.     Pursue Your Passion
While pursuing one’s passion can feel self-indulgent, it’s possible that the benefits far outweigh the costs. In my case, endurance cycling has not only improved my health, it has also taught me how to become a better school leader. In what ways does your passion help you?


George Swain
George Swain

George Swain is associate director for evaluation and accreditation at the New York State Association of Independent Schools, where he also co-directs the Emerging Leaders Institute. Swain has been a teacher, department chair, and division director in several independent schools and writes about endurance cycling on his blog, The Hudson Valley Randonneur. He will lead the workshop “Leadership Lessons from the Seat of My Bicycle: On Becoming a More Authentic Leader” at the NAIS Annual Conference in Baltimore on March 3 from 1:15 to 2:15 p.m.


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