A few thoughts on failing (gloriously)

“[We] foster an environment where failing gloriously is just as honorable as succeeding greatly, where trying something new is just as respectable as setting a record, where the greatest thing we can accomplish isn’t necessarily winning at all costs, but instead feeling at the end of the day like we’ve done something that enriched our lives through effort and commitment. These moments pull us all closer together than any ribbon or medal.” — B.L. CA Class of 2017

It has been over two weeks, now, since CA Track and Field participated in the team’s final competition of the 2017 season, the New England Preparatory School Athletic Conference (NEPSAC) Division III Track and Field Championships, which this year took place on Saturday, May 20th at Cheshire Academy in Connecticut.

That meet might have been the end of the competitive season, but it was not the end of my coaching responsibilities. Over the next two weeks there were numerous wrap-up tasks, from handing out awards and senior tributes at the Spring Athletics assembly, to having my end-of-year meeting with CA’s Athletic Director, to submitting comments for the fifty or so students on the team to be included with their final academic reports. (Even with the help of my assistant coaches, who drafted comments for 80% of the kids, I still labored on writing and editing final versions of comments for three solid days, pleading for more time as I blew past multiple school-imposed deadlines for having them done.) And finally, there was graduation last Friday, and a last chance to say good-bye to departing seniors.

Squeezed in among these activities was a visit from Joni and her family, a trip to Amherst to visit my Mom, a flight to Baltimore and a drive back to retrieve Joni’s car before she and Dennis quit the country for two years, and finally, a “quick” drive to Burlington, Vermont, last weekend to be on hand for Tyler’s victory at the Vermont City Marathon.


If I had been counting on the absence of a full-time corporate job to kick off a life of leisure, I would have felt disappointed. But while I never expected to be idle, I’ve been surprised by how jam-packed these last few weeks have been. In fact, I wonder now how I ever managed to balance work in the office with work at the school. It seems crazy now. Maybe it always was.

Teachers and coaches will understand immediately how the task of working with student-athletes expands to occupy all available time. There is no obvious moment when you think, “I’ve done everything I can to prepare for practice,” or, “No kids need anything more from me today.” Instead, you find yourself fretting more or less constantly about what you’ve left undone, and your limited capacity for paying attention to what’s really going on with your students.

Some people try to convince me that my capacity for worry is what makes me a good coach. But I doubt that’s true. Merely worrying doesn’t help anyone, including the worrier, and too often leads to a cautious obsession with details that don’t matter. It seems to me that worry must be leavened with a willingness to take risks, to fail, to learn, and to trust the process before mere concern becomes actionable compassion. That’s what makes coaching so rewarding, and it flourishes as the season lasts.

But then we reach the end. Not only are coaches and athletes fatigued by the end of school, there is a melancholy in realizing that there are no more races to be run, no more meets in which to correct mistakes, no more ‘next times’ to redeem earlier failures. No matter how proud I am of the team’s achievements, final days of the season always prompt thoughts of how I’ve fallen far short of what I had hoped to accomplish. I want to be reassured that I have done a good job, but find it hard to accept that reassurance when it comes.


At our school, after every season, student-athletes are asked to fill out an anonymous survey about their experiences on their particular teams. Questions on the survey ask the students to evaluate the teaching of sport-specific skills, as well as the teaching of “life lessons” and sportsmanship. Despite daily urging from me and from the administrators for the students to complete the survey, roughly 60% of the kids never do. This makes me wonder whether those kids had a worthwhile experience, or whether being on the track team was just something to do during the spring.

But if I’m lucky, a few kids will write me notes after the season. I treasure these notes more than the feedback from my boss, and far more than any survey results. I value them so because not only do they offer some measure of reassurance that we were all involved in something worthwhile, and I wasn’t wasting my spring, they are amazingly specific about what that something was.

The quote at the beginning of this post is from a note I received from a senior on this year’s team. In addition to being remarkably generous, it puts into plain words what it is that we aspire to. It’s not winning at all costs or succeeding at every turn; it’s doing something that enriches our lives through effort and commitment: simple as that. And that’s what brings us closer together, not the medals, ribbons, and plaques – although I find those nice, too; I won’t lie.


Recently, I’ve had many reminders of how quickly time is passing. I’ve been at Concord Academy for ten years, now, which makes me one of the old-timers, subject to modest recognition for my decade of service. I’ve worked with three different athletic directors, seen legendary members of the faculty and heads of school retire, and watched buildings come down and go up. Ten years ago, we didn’t have a track team at the school, and I’ve seen that program grow from one athlete to a thriving hub of activity with fifty kids turning out each year.

I’m older and slower and approaching another one of those scary, round-number birthdays that usher me into a new age group, and remind me that I need to take my training more seriously.

In theory, I have time on my hands this summer, but I have countless projects that I want to pursue. I suspect the hardest question will be which of those projects gets highest priority. In that, I suppose, I’m not so different from the kids I coach. They, too, have enormous freedom, but also countless projects to pursue. They too, are struggling to decide what pursuits deserve their time, what will – at the end of the day – give them that sense of having enriched their lives through effort and commitment. And maybe, being young, they feel even more anxiety about choosing the wrong path.

I take comfort in the idea that the specific path is less important than the way you travel it, and I must remember to share that idea with next year’s team.

I take even more comfort from the idea that – as an athlete or as a coach — if we must fail, and it seems we must, we can at least fail gloriously.

About Jon Waldron

Running and Racing have been important parts of my life for as long as I can remember. I ran Track and Cross Country at Amherst HS, back in the day, and am proud to have been training and competing with the Cambridge Sports Union (CSU) for more than thirty years. If my bones hold out, I hope to continue for another thirty. Sixteen years ago, I began coaching, first as an Asst. Coach at Newton North HS in Newton, MA, and for the past ten years, as Head Track and Cross Country Coach at Concord Academy in Concord, Massachusetts. I've been writing about running for almost as long as I've been running, dating back to high school, when I would write meet summaries for the Amherst Record for about $0.33 per column inch. I've been blogging about running since 2005, and began blogging at "the runner eclectic" in 2014. Until recently I also had a day job, working full-time as a Technical Product Manager for Nuance Communications, based in Burlington, MA. But I am now on what might turn out to be a permanent sabbatical. Thank you for reading my blog, and please consider leaving a comment.
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2 Responses to A few thoughts on failing (gloriously)

  1. Marcia Boyle says:

    A timely reminder for my life as well. Great post.

  2. Jon Waldron says:

    Thank you, Marcia!

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