Fall 2018 | Features

The Value of Failure

That word — failure —prompts such a negative reaction, doesn’t it? After all, nobody got to Middlebury by failing. But without it, without failure, we could not be our best selves. Eleven essayists explain.

By Matthew Jennings

Illustrations by The Heads of State

November 7, 2018

The Struggle

By Molly Constanza-Robinson

Biochemistry and Environmental Studies Professor

I marvel at the "stairs of death" as I do the other engineering feats of Machu Picchu. The stairs are slabs of cantilevered granite that must be anchored deep within the stone block wall, but they appear to float on hundreds of feet of gaping freefall above the valley floor. Water courses sculpted in stone are banked precisely to contain the flow of the local spring. And like an iceberg, the marvels we can see aboveground are only a fraction of the achievement, most of which lies unseen below, humbly securing footings and draining water.

The beauty of science lies partly in the discovery itself, in bringing some small aspect of how the world works into focus. But there’s beauty in another part of discovery: the messy, human, and failure-littered part of how it came to be. The part where the Stairs of Death must have failed miserably in numerous and novel ways before the Inca found a way to make them hold fast. The part where granite slabs careened off the cliff, where anchoring systems pulled from the wall, where the wheels turned in the mind of the master engineer responding to each failure. I smile to imagine it all, because in considerably less grand ways, I’ve been there. All scientists have. Suppressing feelings of inadequacy, feeling ignorant but grasping anyway because you’re curious, you might be onto something. Because it feels important. In science, failing reflects your bravery in asking hard questions, your daring to venture into the unknown, and ultimately, your belonging in a community that sees beauty in the struggle.

Molly Costanza-Robinson has taught at Middlebury since 2005.

Live from New York… Nah, Just Kidding

By Lucas Kavner ’06

Actor, Writer, Comic

To embark on a career in show business is to embark on a career of comically constant failure. Themoment you leave college and call yourself a writer or an actor or a dancer or a mime or a dance-mime, you’re saying to yourself and the world, “Ninety-nine percent of the time this will not work, but I am going to proceed anyway because I am generally insane.” To be asked to remember a significant failure when you are constantly failing professionally is like asking a basketball player to remember a time they missed a shot. So unless you’re a basketball player who makes every single shot you have ever taken (I commend you, future LeBron), the failure thing is going to take up most of your time.

Early in my career I met an older actor who would always say, “Failure is the game, man.” The first time I heard him say it I thought, “Wow, sounds like a shitty game.” The second time I heard it I thought, “Wow, this guy is really overusing his catchphrase.” But now, years later, I think I know what he meant.

Like many other weird kids with a thing for comedy, I had a dream to be on Saturday Night Live. I loved “Wayne’s World” and Will Ferrell and the way Don Pardo said the words “musical guest” in the opening credits, stressing the “MU” part—“MYEW-sical guest.” I had a fantasy of sitting in the audience during the SNL dress rehearsal, watching Paul McCartney practice his set for the show, then after he was done I would walk up to him and say, “Nice set, Paul,” and he would nod and walk away. For some reason, he completely ignored me in my fantasy.

Anyway, I never really thought I’d get the chance to achieve that dream; it was one of those things you sort of tuck away, never expecting it to really happen. But about five years into performing improv comedy a million times a week in New York City, I was asked to make an audition tape for the show. I strung together a video of myself performing characters in front of a blank wall and sent it in. A few weeks later I was asked to make another tape, then about five or six more after that. I remember falling asleep next to my now-wife every night that summer, my Summer of Tapes, as one might call it if one were so inclined, constantly trying out new characters on her. “A Jewish gigolo. Like a Jewgolo. Is that funny? Are you asleep?”

After a few months of this back-and-forth I got word that I’d made it to the final round of the process, which meant I would perform my audition for all the producers and writers on the legendary SNL stage. I’ll never forget taking the elevator up to the studio, clutching my tote bag of wigs and props, being led to what I was told was Bill Murray’s old dressing room, where I drank too much coffee and heard the guy in the room next to me literally hyperventilating as he struggled to remember how to do a French accent. Finally it was my turn. I walked what felt like a mile to the stage and performed five minutes of characters to a surprising smattering of laughter—they never laugh, everyone is told beforehand—and then I walked off. I thought it went as well as it could have. I was happy.

The next day while riding my bike in the city, I got a phone call and pulled off to the side of the road. I was told, very simply, I “wasn’t going any further.” I remember just sort of nodding and quietly ending the call. Just like that, it was done. Twenty years of a dream over in barely 10 seconds. But then, something strange happened. I was OK. Yes, I was bummed, profoundly so, but it wasn’t earth-shattering, it didn’t knock me off my feet, because at that point I was already so used to this feeling, which may sound depressing but I promise it wasn’t.

Later that night I rode my bike over the bridge into Manhattan to perform in a show, knowing I had failed at a dream, but also sure that I would keep going, because what else can you do? Every day you will doubt some aspect of what you’re doing, you will question a piece of writing, a performance, a sentence, a thought. “Failure is the game, man.” You don’t ever win, but I guess the idea is that, over the course of a career, you get to stack those failures like bricks and make a tower that resembles a life spent trying, and one you can be proud of.

Lucas Kavner ’06 has authored five plays; written for the New York Times, New York magazine, Slate, and the New Yorker; appeared on Comedy Central, VH1, ABC, and Netflix; and costarred in the world premiere of Ghost Brothers of Darkland County, a musical written by John Mellencamp and Stephen King.

The Process

By Jillian Garber ’09

Software Engineer

EARLY IN MY CAREER AS A SOFTWARE ENGINEER, I often took my time analyzing a problem before I would begin work in earnest. I majored in physics, so I had spent years thinking about problems and working (in a fairly linear path) toward the right answer. That’s not to say that I didn’t learn about the value of experimentation; it’s just that I did not yet fully understand the power of this process, nor how to embrace—and even intentionally seek out—missteps along the way. I was so focused on fine-tuning my analysis that I lost sight of what I was gaining when my analysis and thinking went astray.

I was blind to the beauty of the process, fearful not of failing but of wasting time going down an incorrect path and having nothing to show for my efforts. As a result, I would spend time thinking about a problem from every angle before beginning to build a solution.

I’ve since discovered that failure is how we learn, how we refine. By analyzing each failure, by understanding how and why it happened, we can figure out when it is likely to happen again and plan for it, work around it, or use it to our advantage. Out of every failure comes a data point, a piece of evidence upon which to base a better hypothesis, and, eventually, a better solution.

Now when I approach a new problem, I am more apt to begin trying to work out a solution when I still have questions about how things work. It is through methodical attempts that I am able to fill in the gaps in my understanding. This form of trial and error is not merely trying things willy-nilly and hoping something sticks; it is experimenting with variables or options systematically with each one aimed at learning about a fundamental piece of the problem. I have found it is the willingness (and sometimes the intent) to fail that gets us to our goal.

I often end up doing this by only solving for the “happy path” first. Rather than trying to think through all the possible ways things could go awry, I solve for the 90 percent case. If I know the primary part of the problem, and understand it well, I can build a solution and then see where it falls down. It is through this discovery that I find the nuance of the problem and then refine the solution.

Don’t get me wrong; critical thinking and analysis are crucial, but allowing the fear of wasted time or an inefficient solution to prevent you from moving forward is counterproductive. Any idea is good enough to begin exploring its viability. It is through that exploration that you find things you did not previously consider.

In our society we are taught to strive for perfection, to do our best to do everything correctly. After almost 10 years as an engineer, I firmly believe this is to our detriment. Failure as a word seems to have such a negative connotation. No one wants to hear “you’ve failed.” It has a feeling of defeat, of shame. Trial and error, on the other hand, is a system, a process, a proven method to achieve success. If you can turn every failure into a gain, a piece of the greater process, then is it really a failure? Or is it merely an unexpected learning experience? Perhaps if we all reframe our “failures” as “trials” or “experimentations,” we can remove the negative connotation and learn to find value in the effort.

Jillian Garber ’09 is a senior software engineer for Sonos.

Us vs. Them


Three-Time Olympic Skier

It was the spring on 1988. In the past year, I’d graduated from Middlebury, made the U.S. Winter Olympic team, and had the best result of a North American Nordic skier at the Calgary Olympics with a 23rd place in the 20km skate race. No one had expected me to make it that far, that quickly; the U.S. team had put me on their P92 development team, to prepare us for the Olympics four years in the future.

Up to that point I’d been coached by Terry Aldrich, a coaching legend at Middlebury, and by the U.S. regional coach, Dick Taylor. Both approached training with positivity and enthusiasm, focusing on the joy of being outside every day. But now that I was at this next level, I decided I needed a coach who would make me work harder. Friends of mine told me of a new coach out in Colorado, one who thought that the U.S. Nordic team was a mess, so he created a rogue club, an “Us against the U.S.” team. Trusting my friends and entranced by the idea of training in Colorado, I moved west to live in a dorm and train at altitudes as high as 12,000 feet.

I loved the mountains, the sage, the pasque flowers. But as the fall progressed, I found myself crying at random moments—after skiing only a kilometer or while waiting for the pizza to be delivered—while counting the days until the end of the big-volume training period.

Finally, November arrived. I was back in New England for the early-season races, and former teammates passed me like I was standing still. One asked me kindly, “Did you lose some weight?” I was adamant that I had not; I’d not stepped on a scale since the spring, but when I did, I realized I’d lost 10 percent of my body weight. I had overtrained, undereaten, and failed to critically examine both the experience and true agenda of my new coach.

I never recovered. Not completely.

Even as I raced on another two Olympic and World Championship teams, I never performed as well as I once had. I was bitter and angry, and I blamed that “us vs. them” coach; I believed he had used me to achieve his own goals.

Over the years, though, I’ve accepted responsibility for making that choice to change coaches and move west. I had not appreciated the approach of those who had brought out the best in me; instead, I was looking over their shoulders for what I thought was something better.

Now, as a coach of young cross-country skiers and cross-country runners, I draw on that experience every day. I coach like Terry and Dick, coaching the whole person with the goal of helping them find the love of the outdoors, attain independence and self-reliance, and challenge themselves on the trail with their teammates and competitors, not against them.

And at the end of the race, the people around them are there to make them dig deep and find the best in themselves, for themselves. Not for others.

Dorcas DenHartog ’87 competed in the 1988, 1992, and 1994 Olympics. She now coaches high school cross-country in New Hampshire.

Failing Time

By Christal Brown

Associate Professor of Dance

So I'm a Scorpio, and that could mean many things to many people. Connotations, assumptions, and labels are often misrepresentative of the people we really are. A comprehensive view of a person can’t be foretold by an astrological sign.


Well, I’m also born on the 14th day of the month, and if you are into numerology (1+4=5) the number five is linked to the planet Mercury; the messenger with the quick feet.

I don’t live my life by astrology or numerology, but I am aware of who these methodologies say I am.

I am fast.

In high school this was most evident in my time as a local track star. But throughout my adult life, I have noticed that I think fast, plan fast, act quickly—and generally have a very distorted view of time.

In almost 40 years, I have lived about seven lives and hardly said no to anything. I have traveled to many countries, and I can’t tell you anything specific about most of them. No matter what methodology I use to rationalize my navigation of time, I realize I have failed at taking time with people, possibilities, and pursuits of deeper meaning.

As I approach my 40th birthday, I am inspired to course correct this failure not by slowing down but by sinking in and considering the time it may take to complete a vision rather than the time I have to offer the result. I will count the cost of my yes prior to giving it as a commitment of my time, energy, and talent.

I will no doubt fail to meet my own expectations of capacity and interests, but in my failure I hope to find the one thing that changes my concept of time.

Christal Brown is chair of the Dance Department at Middlebury and the faculty director of MiddCORE.

There and Back Again

By David David Gossens ’19

English and American Literatures Major

Let's be honest — we all want to succeed at everything we do. Unfortunately, life isn’t so simple that if we all adopt growth mindsets we’ll ultimately realize all of our dreams.

Success, I believe, relies upon opportunity and being ready to use it. Yet opportunities are not open-ended—and they can be cruelly selective, moving targets with varying degrees of attainability. Sure, it’s nice to encourage people to try new things and be open to failure in order to learn that you can get back up and try again.

But the hard truth is that a lot of the time, once the target has moved past, it won’t be back. This raises the stakes for many situations, and even means that failure, sometimes, is truly the end of the endeavor. The only redeeming quality of failure is that you can learn from your mistakes; eventually, one learns to live with failure itself. That sounds overwhelmingly negative, I know, but to be okay with failing is one of the central tenets of a growth mindset. The second is to begin to believe you can succeed.

When I was a child—and up until my early teens—I loved sports, but I was a benchwarmer. When I did get on the court or field (basketball and soccer were my organized sports of choice), I learned that if I were to contribute at all, it was on the defensive end. Defense was easier. You moved your arms and legs and stayed in front of the opponent. I actually became a pretty good defender—at my peak I earned the nickname “Stonewall”—but on offense I felt inept; I couldn’t pass the ball quickly enough for fear of making a mistake. My style of play was simple: receive ball, freeze, look for open teammate, resume defense.

Looking back on that time, I think this fear was largely self-imposed, but not entirely. I had coaches who wanted to win so badly that, yeah, I felt immense pressure not to screw up. And I had peers, friends even, who could be withering in their criticism.

Eventually I gave up on organized sports, my love of the games eclipsed by my ever-tightening fear of failing, of being the object of derision. And, to be honest, I hadn’t given any of this much thought until a couple of years ago when some Midd classmates casually asked if I wanted to go to the gym to play some hoops. No, I initially thought. I don’t do that. I can’t do that. I’m not good enough.

But I went, and I discovered that without the pressure of performing in front of teammates, without worrying about ruining the game… I enjoyed it. And I went back. Again. And again.

At first I thought I had discovered how to be gritty, how to persevere. I guess there’s some truth in that, but the greater lesson I learned is that failure, at least in this realm, does not have to portend doom. As a nine-year-old kid on the basketball team, all those missed shots were just a reinforcement of what I already believed: that I didn’t belong. Now, the missed shots tell me I’m doing something wrong. So, I keep missing until I make it, and once I do, I try again, just to taste that feeling again.

David Gossens ’19 writes for the Middlebury Campus. He’ll graduate in the spring.

0 for 37

By Stephen Kiernan ’82


In the spring of 1995 I attended a remarkable graduation. It took place at Guiding Eyes for the Blind in Yorktown, New York—a facility that teaches people with visual impairments how to put down their canes and learn to navigate with the aid of a dog. Each graduate spoke about the autonomy, mobility, and pride that a guide dog provided. The final graduate, a fierce-browed woman from Louisiana, spontaneously broke into song, and the whole crowd joined in.

I thought: This is a novel. Over the following year, I read about blindness, I interviewed dog trainers and breeders, I walked the streets blindfolded holding the arm of a woman who was led by her dog. Then I began to write.

It was not an easy time to embark. I had two sons under the age of three. I had a full-time job. But the story had a hold on me. I worked in the mornings, before the household awoke. I holed away in a rented cabin over long weekends. I spent a few weeks at the Yaddo artists’ colony but came home because it taxed my family too much. I remember mornings giving my infant son a bottle while he hung in a sling around my shoulders and I typed with my free hand.

When I finished Moonlight Sonata, there were encouraging signs: I landed an agent. I was named a finalist in a first-novel contest. Friends who read the manuscript cried at the right moments.

Then began the failure. I took the first few rejections in stride, as did my agent. We’re starting at the top, she said, don’t worry. But five rejections became 15. Then 25. Each submission took weeks or even months; always the answer was no.

In the end, Moonlight Sonata received 37 rejections. It’s an easy number to remember, because that’s how many commercial publishers there were in America at the time. They all said no.

As the last answer came in, I happened to be moving books onto a new bookshelf and came across Letters to a Young Poet by Rainer Marie Rilke. That slim volume was a gift, many years before, from now-deceased classmate Katy McGiff ’82. On a page with a corner folded over, I read this: “Ask yourself in your deepest heart if you must write… . . If the answer is yes, then build your life according to that necessity.”

I was inspired enough that I did the least logical thing. I wrote another book, What We Could Have Had. It was never published. Neither was The Wall of Silver. Nor Leaving the Country of My Birth. All of them were a strain to write because of life’s ordinary demands. All of them were rejected everywhere.

Also? Every one of those books taught me that publication was not the reward; the writing of them was. Each of those books educated me in what a novel was, and how to write one people might want to read. All of them schooled me in the reality that failure—whether a publisher’s rejection or simply a bad day of work—is a larger part of making art than success is.

These lessons have been my sustenance. My sixth book will be out soon. I won’t be able to believe it until I hold the hard cover in my hands.

Stephen Kiernan’s sixth book—and fourth novel—will be published in 2019.

To Teach

By John Elder

College Professor Emeritus

In the fall of 1973 I arrived 14 minutes early for my very first discussion class at Middlebury College. This offered me a chance to arrange the tablet-chairs in Munroe Hall 321 in a circle and gather my wits before the 18 students listed on the roster arrived.

After graduating from Pomona College I’d pursued a PhD in English at Yale. My goal in doing so was to find a position teaching at another fine liberal arts college. In Middlebury, which I’d visited a couple of times with a grad school friend who was an alumnus, I’d now found my dream job. The excitement about this initial meeting with students was intensified for me by the strong teaching ethic I’d encountered in colleagues here. In the corridors of Munroe as well as in preparatory department meetings, they were buzzing about the readings, paper assignments, and thematic frameworks of their own courses. I hoped to achieve and manifest a similar standard of commitment.

I had also met some fine teachers at Yale, especially my generous dissertation advisor, Charles Feidelson. But I realized now that we graduate students had never actually received any advice about how to teach. When we did lead discussion sections in large-enrollment courses, each of them was thoroughly framed by and related to the instructors’ previous two lectures. The conversations in Munroe, to which I listened with mounting anxiety, never seemed to touch on practical issues of pedagogy.

I ended up preparing for this class on the first Tuesday of the term by drawing up a carefully shaped sequence of two dozen questions that were intended to lead us into the heart of the Hawthorne story at the top of our syllabus. The discussion I was imagining would engage students in the tale’s main stylistic points and themes, as well as help them get a better sense of Hawthorne’s sly voice. My only concern was that we might not have time to explore all these terrific questions.

I needn’t have worried. Responses to my questions, when forthcoming at all, were often brief to the point of monosyllabic, and students rarely followed up on one another’s comments. Half an hour into this 75-minute class, I was, to quote a certain vice-presidential candidate in a memorable televised debate, “out of ammo.” I struggled to find something else to say or ask before finally falling mute. I felt devastated to have flopped so dismally at the outset of my teaching. Once the class and I had both subsided into total silence, my distress was such that I couldn’t trust myself to speak again.

The formidable Harris tweed coat I had bought the previous week at Farrell’s in downtown Middlebury sat much more stiffly on me than it would after I had taught in it for 37 years. Corduroy jeans and some cowboy boots I’d brought along from California were the other main features of my ensemble that day. Those boots gleamed dully in the fluorescent lights overhead as I gazed down, brokenhearted, at the linoleum floor in Munroe. The students were as immobile and quiet as I, and the remaining minutes limped painfully on until we could all finally retreat from this catastrophe.

The following Thursday’s class meeting was a revelation. Every student seemed prepared not only to participate vigorously but in fact to frame and teach the class in its entirety. Another Hawthorne story was on the syllabus, but first they had a few things to add about the assignment from Tuesday. Aristotle identifies pity and terror as being tragedy’s two main effects on an audience. The students’ pity (for me) and terror (for themselves) marvelously intensified our conversation that morning. Beyond their evident compassion for a clueless young professor, the contrast between these two sessions also showed me the value of a much more tentative, open-ended, and trusting approach to facilitating a discussion. Over my remaining 37 years of teaching at Middlebury, this meeting’s lively and surprising hubbub of discovery, in which the teacher was included as a participant, remained my criterion.

A related insight offered by this unforgettable first week of teaching was that a dynamic yet also coherent class discussion required practice and self-awareness by all participants. Our first, harrowing class, beyond galvanizing the attention of everyone in that room, comically modeled the need to reflect on and discuss what worked or failed following every class meeting. Through responding directly and creatively to such experiences, we could continue evolving from a collection of detached individuals into an authentic community of learners.

John Elder taught at Middlebury, including at the Bread Loaf School of English, for nearly 40 –years.

“I’d Prefer Not”

By Leah Fessler


These days, when I think about failure, I think about a quote from my favorite Herman Melville story, “Bartleby, the Scrivener.” First published in 1853, the story concerns Bartleby, a law clerk who’s been hired by a Wall Street lawyer. At first, he works really hard. He crushes it, as Silicon Valley evangelists would say.

Then, suddenly, Bartleby refuses to do anything he’s asked to. He won’t even make a copy. Instead, he simply replies, “I would prefer not to.” Bartleby gets moved to a new office, then to prison, where he dies.

Bartleby is a grim bastard. In his defiance, apparently unconcerned with impressing his fancy boss, he’s every high-achieving Middlebury alum’s worst nightmare.

He’s also the alter ego I’ve aspired to since reading the story at age 15. Desperate to get an A on my honors English essay, I clearly didn’t get the point of Melville’s antiestablishmentarianism.

And yet, the story is seared in my memory. Throughout my summa cum laude education, hedge fund job, and three years becoming an award-winning journalist, I’ve repeatedly asked myself:

What if I just said no? What if I just stopped?

Nah, I reply, my success addiction catching me. I rarely (if ever) slow down.

Until recently. Jogging in Prospect Park one steamy August morning, I felt my body depleting. I’d been running for 10 minutes but was already exhausted. I’d been working all hours to advance a gender-equality project I had created at the publication I write for. Part-time, I’d been scheduling as many networking chats as possible, plotting my next career move. I’d also been caring for my sick pug and sick grandparents while riding the waves of an emotional breakup and new romance. Plus it was summer, and I’m 25, so I was trying to have some “fun.”

Needless to say, at six a.m. that Wednesday, I didn’t need to be running. My body was saying no. But that nagging urge—to do more, and be more—kept boiling.

You need to stay fit, it told me. Your jeans are getting tight.

Exercising is self-care, it self-corrected.

This push-and-pull consumed my thoughts until an old man with a gray beard nearly ran me over. In Prospect Park, where I run, everyone circulates in the same direction, a spandex-clad herd fueled by one another’s productivity.

The bearded man didn’t give a shit. He was running in the opposite direction at a swift pace, weaving through runners who looked half his age. I didn’t see him because (#Millennial) I was looking at my phone, searching for some beats to keep me jogging.

“WAKE UP,” he shouted, his baritone cutting through my music.

I looked up, just quickly enough to catch a glimpse of his T-shirt. It read, in bold white letters, “I’d prefer not to.”

While a beautiful coincidence for sure, this incident didn’t tectonically shift my approach to work, relationships, and success. That’s not how life works.

It did, however, wake me up.

In 2018, life’s treadmill only seems to get faster. Despite my immense privilege, educational success, and professional accomplishments, I’ve been trained to believe that doing “enough” is bad, and “slowing down” means failure. As a woman, if you’re not exceeding expectations, you’re falling behind. And even if you are exceeding expectations, you can still be disparaged, abused, and ignored, as the #MeToo movement proves. For women of color and LGBTQ people, this injustice only intensifies.

But running faster doesn’t give you more energy, as I’ve repeatedly learned in the four years since graduating. It doesn’t make you happier, either. Because when your motivation is fear of failure—as demarcated by standards you didn’t set, and goalposts you’ll always move—success of any form—a quiet Sunday morning, a mile run unbridled, or even a big promotion—becomes ephemeral.

Failure, I’ve come to learn, is to be overwhelmed, unhappy, and unfulfilled. Which means that success, quite simply, means peace. To achieve peace, we don’t need to step off the treadmill. But we do need to slow it down. To leave situations, jobs, and relationships that cause us pain, or feel too heavy. To do less.

In making like Bartleby and occasionally stating, “I’d prefer not,” we do no spite to ourselves, or others—quite the opposite. In doing less, we preserve energy for what matters, a measure we can only set for ourselves.

I stopped running that day, after the old man nearly knocked me out. Thank you, I whispered to him, and myself.

Leah Fessler ’15 writes for Quartz, where she created the blockbuster multimedia project “How We’ll Win,” which focuses on the fight for gender equality in the workplace.

“What Am I Supposed to Do?”

By Will McDonough ’07

Secondary School Teacher

I still recall the first time someone gave me permission to fail,to admit that I couldn’t do it all.

It was an early spring day in 2006, my junior year at Middlebury. I had just sprinted across campus to catch the bus to a track meet at Williams. I’d been under significant stress in all areas of my life: socially, academically, and athletically. Like many of my classmates, I felt that doing anything less than my best was a failure.

I wanted to be the perfect boyfriend, the perfect student, the perfect athlete. I craved affirmation from everyone with whom I interacted. I didn’t believe I was enough unless I was great.

As I approached the bus, I saw assistant track coach Nicole Wilkerson.

“How’s it going, McDonough?”

I don’t remember what I said, but whatever it was, she must have sensed that the stress was mounting. I was crumbling under the pressure to be a good boyfriend and to meet the lofty expectations I had for myself as a recently declared history major, and I had failed to break four minutes in the 1,500-meter event, achieving a “failing” time of 4:00.84 the week prior.

And then she told me I couldn’t get on the bus.

I couldn’t believe it. I had to go. It was Williams. It was my weekend to break four minutes. My team depended on me. Did she think I was too weak? That I couldn’t handle it?

I protested, told her she was wrong, declared that I had to go.

But then, on the brink of tears, I conceded.

“So what am I supposed to do?”

“Go for a walk,” she said. “Watch the sunset. Relax. Do whatever you have to do for you. Take care of yourself. You can’t be the best of anything if you can’t care for yourself.”

That afternoon I cried tears of overwhelming exhaustion and relief as I walked the Trail Around Middlebury.

For three years, it felt like I hadn’t rested. I hadn’t hit pause. I was so out of touch with myself that I had no idea what I needed. I had made innumerable mistakes, but I still didn’t think I would recover if I was dumped, if I failed a history test, or if I couldn’t run fast.

I thought I’d be letting everyone down.

But at this moment, in an era before the mental health of college students had been pushed to the forefront of conversations in higher ed, I was confronting what it meant to be weak and vulnerable but simultaneously safe.

Twelve years later, I’m an eighth grade teacher, and I’m also a dad to three amazing little kids. In each of these settings, the young people with whom I interact need to be shown grace for their missteps. But most importantly, they need help having grace for themselves.

And the best way I’ve found to help them take care of themselves is to share that message I received that morning at the bus to Williamstown.

“You are enough.”

Sadly, I don’t think we’re ever out of the dark. I still struggle to believe that my worth is not the result of my performance. Now, though, as life humbles me more than ever, I try to use my failures and missteps to model imperfection and grace for both my students and my own children—as we all attempt to be the best versions of ourselves.

Will McDonough ’07 is a humanities teacher at New Canaan Country School.

The First Time

By Dan O'Brien ’96

Poet and Playwright

This past summer in New Hampshire I was feeling nostalgic for I don’t know what. Of course this was where I had first come to know my wife’s childhood. Where her parents had sat across from me at the country club and asked, “What have you got against capitalism?” Where after 10 years together, striving in our respective artistic careers, my wife and I had attended our engagement party in August just after my play had been panned in the New York Times.

Everybody had looked at me like I had accidentally killed a child. All I had ever wanted was to be a writer—that’s why I’d gone to Middlebury, where I’d fallen love with Jessica, and she loved me, I assumed, because of my words. Writing was how I believed I could right the wrongs of my parents, how they’d been abused and how they in turn abused us.

My parents had brought a dessert wine from Virginia. My usually logorrheic mother had huddled in a corner. My taciturn father had chatted aggressively with my fiancée’s family’s friends and neighbors as if trying to prove something. This place must have reminded him of his uncle’s lake house in the Catskills where he’d felt happy hunting and fishing as a boy. When his Uncle Marv died, my father’s father, a plumber who’d failed at opening and running a plumbing supply store in Scarsdale, New York, couldn’t buy it. And my father set out alone in the same town with his wife’s family’s money to be a corporation-of-one and failed. And he lived on that same money pretending to work. And his kids didn’t talk to him anymore and he didn’t care. He was up here in New Hampshire because he had to be, where he had to see my fiancée’s father, the corporate success with this lake-adjacent woodland house, the prestige cars, friends, and children who loved him. No wonder my father—and my mother, and most of my siblings—refused to come to our wedding here the following year.

For a long time, I also stayed away. I had success with my writing. We had a daughter. Then my wife got cancer, and six months later I did too. A little over a year ago we came back here for the first time since, feeling timorous, almost embarrassed, and now this past summer again too. What was I feeling then? Not nostalgia. Something like pride. As I watched our daughter in the lake suddenly swimming for the first time.

Dan O’Brien’s play The House in Scarsdale was recently named PEN America’s 2018 award-winner for drama