When Jack returned to school this year, he brought with him the news that his mother wasn’t well. She’d been sick all summer—lung cancer, I would later find out—and nothing was certain. She was in treatment, in the hospital, and things weren’t looking hopeful. Jack’s mom’s name was Mary, and she was his greatest support in life.
Jack came to our school during his sophomore year. He was admitted by my predecessor, and he came in with solid ninth grade grades: A’s mostly and nothing below a B. Still, he is quirky—enough so that someone early on would have asked some questions about his learning, poked around the topic as an invitation for Jack, or his parents, to share more about who he is. Whether those questions were ever asked or not, I don’t know. What I do know is that all we’ve had to work with is Jack, as is.
Jack’s arrival to campus coincided with my predecessor’s departure and my first year as Academic Director, a job that is, it turns out, mostly about helping people solve problems with other people. Jack is one of the people who has posed some challenges to teachers. He is somewhat withdrawn in classes, not particularly organized, not great at meeting deadlines, or following instructions, and when confronted by any of this, or anything else, he is often stubborn, a bit rigid, and defensive in a belligerent kind of way. In his 10th and 11th grade years, I had him in my office on a number of occasions—to discuss a cheating concern, to discuss a project that completely missed the mark of an assignment, and repeatedly to talk about his falling behind enough, and in enough classes, that his training had to be withheld until he caught up. In all of these conversations, one-on-one, I had the opportunity to see what the teachers were dealing with: the rigidity, the dismissiveness, the chronic lying and rationalizing. Still, I also had glimpses of a Jack who wasn’t entirely that way—there was some willingness to talk and take some ownership.
In those first two years I had a number of conversations with Jack’s parents as well—some over email, or on the phone, and some in person. In those conversations Jack’s father, Rob, always wanted to talk about Jack’s grades and his failure to meet their expectations. I would describe Rob, in all of those conversations, as flabbergasted and a bit volatile. And I will admit that his surprise and frustrated confusion over Jack’s struggles, always left me surprised and confused. It seemed so obvious, to all of us who worked with him, that Jack had some challenges.
On one of their visits to campus, Rob met with Jack’s chemistry teacher to gather materials from her class so that he could teach Jack what he hadn’t yet learned, on vacation when he would be at home. At the same time, Mary met with me; I had the easier job. I don’t remember what time of year it was, but I do remember it was a beautiful day and Mary and I sat outside in the gazebo next to my office. I want to say it was spring, and a Saturday. I was struck by her obvious love and caring concern for her son. Still, she shared her husband’s surprise that Jack was struggling, and seemed to have no idea why that would be. We discussed openly some of the challenges he’d had—the lapses in honesty, the rigidity, the refusal to ask for or accept help. Mary’s approach was a softer one—not the belligerent determination to set things right, once and for all, that her husband seemed to express, but instead a desire to understand Jack and help him understand the world.
What I saw was a mother’s love, to be sure, but it was also her own compassionate spirit. I know this because, while we were talking, a young and impatient Quinn was darting in and out of the gazebo interrupting our conversation. If I had been in Mary’s shoes, there to discuss my own child’s difficulties in a school far away from my home, and someone’s bratty kid was interrupting my fifteen minute window, I would have been annoyed. Instead, Mary lit up each time Quinn showed up. She engaged her in conversation and smiled at her antics. She was apologetic for taking me away from Quinn. In that experience, and in many moments after, I recall thinking how lucky Jack was to have Mary as his mom—someone with patience and understanding and such genuine kindness.
On another occasion, Sam, Quinn and I walked into the pizza place down the hill from school and were seated at a table near Jack and Mary who had come for a visit. They didn’t notice us come in, rapt as they were in their own conversation. I remember Mary’s beaming smile as she listened to her son on the other side of her table. I remember her leaning forward, toward him, her arms resting in front of her. I remember thinking how much she must have missed him. And thinking again how lucky Jack was to have her as his mom… someone who took clear joy in being with him, who could understand him and encourage him, even if no one else would. Mary is someone who would love him, unconditionally, and help him navigate the world.
And those are the things I thought about when we learned, at the beginning of the year, that Mary was likely dying. Of all the people in his life, why her? I couldn’t imagine Jack existing in this world without her.
Every day this fall was touch and go. Jack came to school in August, but his mind and heart were at home. When it was time to leave for Chile, a million miles away, his parents decided he should go—to stay with his peers, keep busy with school and skiing, try to live as normally as possible. But as soon as his two day journey to Chile was complete, Mary took a turn in the hospital and Jack’s dad called school and asked for help getting him home to Ontario. With no time in between trips, Jack made the long journey home by himself. He stayed home through October, but as November approached, they again made the decision to have him return to school, and to go with the group to train in Colorado. He had effectively missed the first quarter of school, and although his teachers were highly skeptical that he’d done any work while away, Jack told us he had, and that he was going to be able to get caught up.
I wasn’t confident that Jack would be able to recover academically, but I was certainly willing to let him try. When I was in his shoes, away at school while my mother was at home dying, I couldn’t have cared any less about my school work. And I remember the ways that my teachers’ reactions to that fact impacted me. I had some professors who seemed to think they knew what was best for me and told me what they thought I should do, and others who asked for my input. I remember the gratitude I felt for those few people who offered me the opportunity for some little shred of control, by letting me make some decisions for myself. My Russian Literature teacher was one example; he was entirely understanding when I wanted to read something other than The Cancer Ward, an assigned text for the class. And while Jack was at school, and his mother was dying at home, in spite of it being my job to focus on the integrity of the academic program, I really didn’t care much about his school work either. Whether he had done his work or not didn’t matter to me—all that mattered to me was his safe passage through each day. And given that Jack is a kid who doesn’t appear to confide in anyone, other than his mom, and is a kid who doesn’t ask for help, I didn’t feel safe assuming that was a given.
It was after the November trip to Colorado, when Jack was back on campus, that I started feeling a sense of urgency about his daily health. One day in mid-December I learned he hadn’t shown up to his morning classes. I went directly to his dorm and knocked on his door. My knock woke him up but only barely. When I told him it was me, and he told me to come in, I found him still in bed. He couldn’t fully open his eyes yet, and he told me he didn’t feel well—he couldn’t put his finger on what it was, but he just didn’t feel right. I encouraged him to get up, try to drink some water, see if he felt better getting some fresh air outside of his stale dorm room. A few days later, just before Christmas, while Jack was on the hill at training, his dad called school to say that Mary had died that morning. By the time Jack’s training session ended, his plane ticket was purchased, his ride to the airport arranged, his dorm parents and teachers informed. Jack’s coach, one of the few adults he seemed to trust, told him the news. He had a few minutes alone in his room and then he was whisked away to the airport for what would, inevitably, be the worst Christmas of his life.
In the months of winter that followed, Jack and I spent more time together. I got updates from his teachers weekly, and weekly I formed plans with him for how to get caught up. In spite of his initial reluctance at my suggestion, I convinced him to drop the Calculus class that was, by then, so far gone. And we put his fall electrical engineering class on the back burner as well. That left Physics, Mechanical Engineering and English to get through, and I was determined that he would get through them so as not to have the whole year be a complete loss. I knew I, and he, had to have something to show for the time and investment, and with graduation looming, he needed those credits. I was terrified, I will admit, of what his father’s reaction would be if we missed the mark. But more than that, I kept thinking of Mary. It is, of course, a parent’s greatest worry—to be separated too soon from your child. If it is me who goes too soon, I worry about who will care for Quinn, and who will help her navigate life. In the months after Mary’s death I had a mounting sense of purpose. Without his mom, I worried Jack had no one to help him navigate the work he had to do. And, whether Jack wanted my help or not, I was determined to help him get through the academic hurdles of the year—it was the one small thing I could do, for her.
To my surprise, Jack was willing to accept my help, and he had his own determination to get through the year, even if he struggled with execution. In the beginning, I saw my role as helping him identify and organize a few tangible goals for the week ahead. I imagined that was the main thing he needed—to be pointed in the right direction and told where to begin. He left my office, again and again, with a clear plan and good intentions. And again and again I learned from teachers that the targets weren’t met. No problem; we’d start again. And over the course of the many restarts we had, when I was willing to begin again, without judgment or disappointment—just as a matter of course—Jack began to trust me more and I began to understand him better.
In my three years, so far, in my role at school, I have worried a lot about whether my colleagues, or the students and their parents, will take me seriously as the director of an academic program. I’ve worried about whether or not I have the intellectual or academic credentials necessary to be credible and effective, or whether I’m a staunch enough defender of academic “rigor”—a favorite term of my predecessor and one that for some reason gets under my skin. I still don’t know if I have enough of those qualities. What I do know is that I have always been someone who stands up for the underdog—I have always been a staunch defender of those in need of defending. So this year, when I would learn that Jack didn’t show up for class, I would just go and wake him up. I slept for a year after my mom died. I had a job, which I went to, and I had friends I occasionally saw, but mostly I slept—in every free moment. I remember it like it was yesterday, even though it was twenty-six years ago. When Jack didn’t make it to a meeting we’d set, I would go and find him. And when I set up meetings for him with his teachers, and he didn’t show, I expected them to do the same. And, when they didn’t, I would. Any frustrations I had this spring were not with Jack—they were with the adults working with him who seemed to think he should be able, on his own, to do all the things they laid out for him to do—with no regard to how trivial or potentially meaningless they may have seemed to him. And of course all of those people are people who have loved ones to go home to at the end of the day, when Jack was going “home” to his dorm room alone.
On more than one occasion, Jack offered me apologies for falling behind. “I don’t mean to,” he told me, with sincere regret, “I just have such a hard time focussing.” And on each occasion I assured him it didn’t matter—and to me it honestly didn’t. Also on more than one occasion, Jack lied to me about work that was supposedly done but, in reality, wasn’t. I know he didn’t want to lie to me, he thanked me all the time for helping him, and he agreed to anything I asked of him—including working in my office first period every single day during his senior spring. And yet, I came to understand that he either didn’t see any alternatives to lying, or that he did so automatically out of long established habits. One day, late in the spring, when Jack said, “Oh, I must’ve just sent the wrong file! I have the paper done,” I finally, but gently, pressed him. I asked him to tell me the truth, just so we could make a plan, and I promised him that no matter his answer I wouldn’t be mad. Jack is much taller than I am. He is a big, strong guy. He’s eighteen years old. He paused, looked at me cautiously and asked, “You promise?” As a person in the world without my mother, even at forty-seven years old, I feel that way sometimes still—vulnerable, like little a kid.
I came to understand that Jack wouldn’t get anything done in his room, where there was no pressure to stay on track, so I suggested he work in my office and he agreed it was necessary. And I learned that he often had trouble figuring out where or how to begin his work, but if Jack had someone help him get started, he could take off and get the thing done. For his Film Studies homework, a class I once taught, this was pretty easy. I’d read the assignment and ask him his plan of attack. In that process, it would be clear which aspects of the assignment he didn’t understand. We’d find the answers together and then he’d be ready to go. A short paper that he had been struggling to complete for a week was done in an hour. With my back turned to him, as I worked on my own work, I listened in awe at the speed of his fingers on his keyboard.
In physics and engineering I was markedly less helpful, but even there, as I looked at assignments with him, I could see he would get lost in the details. I started to see assignments as I imagined he did, and I rewrote some to make the sequencing of the work more clear. One night I stayed late to help him get a physics test made up. He was up against a firm deadline—he had to complete two tests before leaving the next day for a ski race and trip home, and this was one of them. He worked for an hour and finally emerged from his study room looking frustrated and exhausted. He asked me if he could finish it the next morning, but once he’d seen the test, I couldn’t let him do that. I told him to leave his phone with me and take a break, to step outside into the winter night and get some fresh air to wake himself up.
As soon as he was gone, I started googling the terms from the problem he was stuck on. I never took a physics class and, even if I had, there’s no way I would’ve remembered it. I was searching for information that would help me ask him the right questions—questions that might jog his memory and point him in the right direction, without giving anything away. Just as I was starting to gain some ground, Jack burst back in through the door. “I have an idea!” he announced. “I don’t know how you’ll feel about this, but the thing is, I know this material, and if you were my teacher, you’d be able to ask me a question or something that would get me going, you know?” He was nervous, trying not to offend me, and I couldn’t help smile that we were having the same idea. “There are these videos from class, maybe you could watch one and that would help you help me…?” We logged into his class page and he pointed me toward the video files his teacher made, and then he left me alone in a study room while I tried to learn the physics he was trying to do. Fortunately, the content of that one question was addressed early in the video and I knew just the question to ask that would help him correct his mistake. He had it done in a matter of minutes and we were both so pumped. He figured out the problem and finished the test.
He had one more to complete the next morning. We agreed he would wake up early to review and then come to my office midmorning to take the test. I left campus that night feeling great confidence, but by morning I remembered what mornings were often like for Jack—he had a hard time waking up. Driving to work I started to panic—if he didn’t wake up on time, he wouldn’t get the test done, and he had to…I couldn’t let him leave without it being done, and I couldn’t not let him leave either. I called the campus phone from my car to ask the staff member on duty if he’d shown up for breakfast. He hadn’t. I asked her to go and wake him up in his dorm. I stopped at the gas station to buy him an egg sandwich and some juice and drove straight to his dorm. When I knocked on his door it was clear he’d fallen back to sleep. “Jack,” I said, “it’s me. I brought you some breakfast. I’m leaving it outside your door. I need you to get up, and review for that test. Okay?” I tried to sound confident. He tried to assure me he was too. I walked away, conscious of his privacy and conscious as well that time was ticking away. Thirty minutes later I sent him an email: Jack, are you up? I got no reply. Ten more minutes and I wrote another: I need you to tell me what was in the bag I left outside your door. In a minute I had a reply: "Breakfast sandwich and juice. Thank you.”
Jack made it to my office on time. He took the test. He thanked me. He made it home for his race and spring break after that. Winter had been a marathon—it was emotional and, for me, every interaction felt so high stakes. Every day I worried about him. Every day I thought about his mother and the worry she must have felt on her way out of this life. Every day I thought about the lost kid I was when my mother was dying. Helping Jack was like helping my former self. My motivations became selfish in this way.
After the break, the end was in sight and many other things were going on at school that took my attention. I checked in with Jack still, but the daily worry had lessened a bit. On Mother’s Day, I wasn’t thinking about Jack but instead was thinking about my own mom and about myself and Quinn. In the afternoon I saw an email from school—they were looking for someone to pick Jack up at the train station at nine o’clock in Waterbury. I hit reply and offered—the train station is close by and remembering that this was Jack’s first Mother’s Day without his mom, I wanted to be there for him. I was determined to be upbeat when I arrived, but my heart was aching for him.
When the train arrived, I watched as people got off until I saw Jack. He was looking fresh and happy. He had only a small backpack. “Hey Jack,” I waved, trying to seem casual, “where have you been?” He got in the car and we started toward school. “Oh, well, I was in Massachusetts. I just ran a half marathon,” he said, as if it was very run of the mill.
In the course of our drive I learned the whole story. The day before, anticipating Mother’s Day, he was looking around on the internet for something he could do. He found a Mother’s Day Half Marathon in western Mass that was a fundraiser for a local organization that supports cancer patients and their caregivers. He figured out where it was, figured out how to get there, figured out where to stay, asked at school if he could go, got permission from his dad. He took a cab to the train station and got on a train leaving Vermont at 8pm. He arrived in North Hampton in the late evening, and took another cab to the bed & breakfast he had called in advance. They were closed by the time he arrived, but the cooks were still cleaning the kitchen so they called the owner and got him checked in. In the morning he walked to a diner for breakfast before the race, but the diner was closed. He was worried about being late so he walked four miles to the start of the race, grabbed some fruit and bagel chunks from the finishers’ tent, and with that he started his first ever half marathon, having already walked four miles just to get there.
He was at the back of the pack to start, but he kept pushing his way toward the front. His goal, he told me, was to come in under 2 hrs, and to never stop running. He finished, I would learn later, in 1 hr 52 min. He was 96th out of 400 or so runners. When the race ended, he changed into dry clothes—it had been raining all morning. He had time to kill before his train back to VT. He watched as other runners finished, standing the whole time so his dry clothes wouldn’t get wet. He watched the spectators mostly disperse toward the tail end of the race, but he had nothing else to do, so he cheered in the final racers. He took a shuttle to North Hampton. Went to a burger place, enjoyed exploring the town. Eventually, he got on his train.
My conversation with Jack on the way back to school was outrageous. Every question he answered led me to more questions. I couldn’t believe what he had done—some days he can’t get himself out of bed, but on that first Mother’s Day, he got himself to a place he’d never been, without any help, and done something incredible he’d never done. I was so energized by his story, and at the same time he was increasingly desperate to lie down. He hadn’t eaten since midday. I told him he was going to be sore the next day, and he said, with a laugh, “Oh. I’m incredibly sore right now!” We cracked up again and again. I bought him a bag of ice, for his legs, at the gas station, and he grabbed some pizza before I dropped him off, as close to his dorm as I could drive my car.
When I looked up the race online the next day, I noticed Jack hadn’t shown up on the fundraiser’s page. I asked him about it and he told me that because he just paid his entry fee on arrival, he missed that boat. I emailed the race organizer and told her Jack’s story. She agreed to set up a fundraising page for him and said it would still be open for a week. Jack liked the idea of putting it out there, just in case anyone was interested. So, he set it up, wrote about why he had run the race, about how his mother loved to run and she ran every day. He welcomed contributions, thanked anyone who would be reading it, and then he forgot about it. Surreptitiously I sent the link to the staff at school and told them the short version of what Jack had done on his own. It was the story of a Jack that most of us had never known. The donations, of course, started pouring in. I asked Jack, a couple of days later, if he had checked his page. “What page?” he asked. By the time it was done, Jack succeeded in being the #1 fundraiser for event—for this year and in the history of the race. The race organizers asked if they could share his story and Jack was honored to help them write it. They couldn’t believe he hadn’t trained and couldn’t believe he’d never run that distance before. They’ve invited him to come back and run the event for free anytime he wants and, if he does, I have no doubt he’ll be treated like a celebrity.
There were only three weeks of school after the Mother’s Day race and Jack spent his remaining mornings in my office completing work, and his afternoons and evenings doing what all the other seniors were doing—enjoying time with his friends, reflecting on their years together, getting ready for graduation. He went on the senior trip, he asked an amazing girl to the prom and she said yes, and at graduation he stood up in front of everyone, as did each of his classmates, and he gave his graduation speech. He was wearing his mother’s identification badge from her job in the respiratory unit at the hospital where she had worked. He told us all he was carrying her with him. And in his speech, in his quirky and understated way, he said, “As some of you may know, I ran a half marathon this year…” and at that the audience erupted into cheering and applause. “This year,” he went on to say, “has been the worst year and the best year of my life…”
Working with Jack this spring reminded me that in working with students, teachers have to study them. We have to slow down and pay attention to the details, we have to ask questions and work to understand what they are trying to communicate. Jack’s capacity as a student is, of course, so much greater than what sometimes appears on the surface. His moments of struggle were not about him being lazy or stubborn, even though it may have looked that way on quick glance. And that is the work—to go beyond the quick glance. We have to figure out about the students what the mothers already know—we have to be willing to lean across the table, with genuine interest, and listen.
Teenagers are incredible people and they all go through their own metamorphosis. And still, each victorious arrival is amazing, and sometimes even breathtaking. At the graduation party later that night, I stood off to the side of the dance floor during karaoke with some other faculty—Jack’s teachers and coaches among them—and we watched as Jack took the mic and whirled around with his classmate Sophie, belting out the lyrics to their song: “I’m coming out of my cage and I’ve been feeling just fine!...Destiny is calling me, open up my eager eyes, cause I'm Mr. Brightside!” All the kids knew the song and were jumping up and down with the beat, screaming along with their friends. We old people were all amazed, and laughing, and I was crying, because what else could I do? What a privilege it is to watch people emerge, as their big colorful wings unfurl.
