There’s a famous story about a man named Dorian Gray, written by the fabulous Irish author Oscar Wilde. I first read “The Picture of Dorian Gray” in high school and to this day it remains one of my favourite books. You might not know the story, but the idea is unforgettable: Dorian maintains a perfect and flawless outward appearance while a hidden painting absorbs all the consequences of his choices and compromises. On the surface, everything looks beautiful, effortless, and controlled. But underneath, the painting darkens, twists, and decays, recording every selfish choice, every flaw, every hidden cost of keeping up the image.
As a kid, I didn’t have a portrait in the attic. But I did have something surprisingly similar. I had a label, a position of sorts in my school and friend group, and a set of expectations that I carried with me every single day. For a long time, it felt like I couldn’t let anyone see the wear and tear beneath the surface.
In my case, the label came from elementary school. They used to call me “IBM.” It actually started on Play Day, a day at the end of the school year in Ontario, Canada where it’s way too hot, the schedule goes out the window, and everyone’s outside rotating through games and stations. Water balloons, races, popsicles, and parachute are popular stations. It is the kind of day that feels more like summer than school. I think I was in grade three.
I remember that we were all sitting cross-legged in our class lines on the field, waiting for the next activity. Someone, I think one of my friends, started it as a joke, just saying “I… B… M…” like I was some kind of walking computer.
And then it spread. A couple kids joined in. And before I really understood what was happening, the kids were chanting in each of our class lines—“I-B-M, I-B-M.” The nickname stuck after that.
When it came to school, I seemed to have a knack for most subjects, and math and science just made sense to me. I got things quickly and usually finished my work early. Teachers complimented me and used me as a role model for the class, and my grades were high. Looking back at my old report cards, it’s kind of funny. This was back in the day when teachers actually provided hand-written comments that were completely personal to each student, and although they were positive, every single teacher mentioned, in big, bold letters, that I talked too much and often distracted the other kids once I was done my work. Their solution was to grant me a leadership position in the class as a “peer helper.”
It may have seemed like I had it all together, but school was the only place where I could feel capable and seen. I wasn’t athletic at all (still not coordinated to this day!). I wasn’t socially confident as a child, so making friends was not easy. And at home, things could be unpredictable, as my parents often fought or stayed away from each other in their separate rooms.
School made sense. It was structured. It gave me a pattern I could count on, a predictable set of rules where, when I did the right things, the rewards were visible and immediate. I got stickers, stars, and accolades for doing well. I got attention when I answered questions correctly, praise when my handwriting was neat and my papers were organized, and little nods of approval when I achieved high grades. Everything was measurable and tangible. I could see my value reflected in my report cards, in my teachers’ comments, and in the way my friends looked at me when I performed well.
Over time, it became easy to confuse my performance with my self-worth, as they started to blur together. The better I did, the more I felt I was on solid ground. The more recognition I received, the more I believed I had a place.
And the school system didn’t really challenge that belief. If anything, it kept reinforcing it.
As school went on, the rewards became bigger, more formal, and harder to miss. In high school, entire graduation and award ceremonies were built around recognizing “high achievers.” More time on stage. More applause. More attention. You could feel, even if no one said it out loud, that some accomplishments mattered more than others, and that some people did too.
Then came university applications, competitive scholarships, honour rolls, distinctions. The same pattern, just with higher stakes. Work hard, perform well, stand out, be rewarded. It all made sense. It all felt normal.
Until it didn’t.
I didn’t go to my high school graduation.
At the time, I had a simple explanation ready if anyone asked. I brushed it off, said it wasn’t a big deal, and that those things were kind of arbitrary anyway. The truth was much harder to admit. I had not been chosen as valedictorian, and somewhere along the way, that had come to mean more to me than I realized. It felt like my own personal ugly painting was out on display for everyone to see, like I had fallen short of the role I had built my entire identity around. And I could not bring myself to sit there and feel that.
So, I stayed away. Not because I didn’t care, but because I cared too much. Because somewhere deep down, I had learned to measure myself by how well I performed, and when that measure slipped, it did not feel like disappointment. It felt like intense shame.
This pattern isn’t just a personal quirk. As early as the 1960s, William H. Missildine described how children can tie their self-worth to being “good” or “right,” especially when approval feels conditional. He coined the term “successful failure,” where the student appears accomplished, but the cost is their personal well-being. Later, Patricia Marten DiBartolo expanded on this with the concept of activity-based self-worth, where your sense of worth becomes tied not just to performing well, but to consistently producing, achieving, and proving yourself. In this framework, worth is not something you have, it is something you have to keep earning. For many, this creates a relentless cycle: succeed to feel worthy, avoid failure at all costs, and protect your image at the expense of yourself.
In our work with teens, we find strikingly similar themes. Teens describe perfectionism not just as “high standards,” but as a compulsive need to be flawless along with an intense fear of judgment or failure. One young perfectionist summed it up seamlessly, “I need to be perfect or else the world’s gonna end”.” Rather than talking about achievement alone, many describe perfectionism in terms of self-worth, social comparison, and anxiety about being seen as anything less than adequate, as though any mistake or lack of productivity were evidence of a flawed self. Interestingly, our recent study shows that teachers see this too, noticing students who seem outwardly accomplished yet struggle silently with pressure, self-doubt, and the fear of being “not enough”.
Looking back, I now realize that my childhood self was carrying a little Dorian Gray portrait of my own. Mine was not hanging in some dusty attic. Instead, it was hidden inside me, recording every misstep, every near miss, and every panicked moment about not being enough. The IBM chants, the early successes, the careful avoidance of anything I might fail at were all brushstrokes on that hidden canvas.
Like Dorian, I thought my image had to be flawless. I believed that any imperfection would expose me or I would become completely unraveled. And even when things looked good on the surface, when I succeeded and everything seemed to line up, the feeling never quite settled. It was fragile, temporary, and always one step away from slipping.
But unlike Dorian, the story does not have to end there. The portrait we carry does not have to stay hidden, and it does not have to hold all the weight.
We all know the truth. A child cannot be good at everything! School should be a place where it is okay not to be good at every subject, where kids can take the time to explore, practice, and grow. A student who struggles with math might excel in storytelling, leadership, or art. The key is to discover where strengths lie, work to improve where possible, and understand weaknesses without shame. That is how direction and resilience are built. School should teach us how to bend without breaking, to find our own path, and to trust that struggling is part of becoming strong.
Parents, teachers, and school staff can help by recognizing the strain without judgment and reminding young people that their worth is not something they have to keep earning. They can focus on effort, curiosity, and persistence instead of just perfect results. They can rotate roles so leadership is not only for the top students. They can normalize mistakes, celebrate risk-taking, and reflect on what was learned rather than only what was achieved. They can point out value beyond performance, like kindness, creativity, teamwork, or curiosity, so students begin to see themselves as whole people, not just as the sum of their grades. In small but consistent ways, they can create spaces where it is safe to stumble, explore, and grow, helping young perfectionists discover that being human and learning is just as important as being right.
The challenge is that teachers and schools are constrained by the school system itself. Students are pushed along like items on a conveyor belt, grade to grade, award to award, with little room to struggle, explore, or fail safely. Pressure from parents, administrators, and policy emphasizes results, high success rates, and easily measured achievements. Even the most well-intentioned teachers can struggle to give students the time and space they need to discover their strengths, face challenges, and build resilience. The current school system rewards performance, but not always learning, growth, or the messy, human process of finding direction.
On paper, the conveyor belt looks like success. But underneath, it can produce students who never discover their real strengths, never learn to recognize their weaknesses, and never build the resilience that comes from facing challenges. School should be a place where it’s okay not to be good at everything, where kids can take the time to learn, and where the focus is on growth, skill development, and finding direction, not just performance. School should teach us how to bend without breaking, to find our own path, and to trust that struggling is part of becoming strong.
For those of us who learned early to measure ourselves by every grade and every accolade, there is a way forward too. Not by perfecting the image, but by loosening our grip on it. By allowing what has been hidden to be seen, not as failure, but as part of being whole.
Maybe that is the real lesson Dorian Gray leaves us with. It is not the image that defines us, but what we are willing to see and to hold with compassion, when the image begins to shift. And in that space, something more genuine forms. Not perfection, but something closer to freedom for students and for a system that stops locking them into a single image of success. Right now, the school system treats achievement like a portrait that must stay flawless, measuring kids only by what can be seen on the surface. If we let them stumble from time to time, we give them the chance to step out of that portrait so that they can see themselves as whole, evolving, and capable of more than any single grade or accolade can show.
Today’s cultural story about success often sounds like this: You are unlimited. You can do whatever you want. There are no boundaries. Push harder. Grind more. There’s no finish line. Celebrities, athletes, and business leaders amplify this message. Even in sports, when quarterbacks like Russell Wilson talk about being “unlimited,” it resonates because we’re trained from an early age to believe that grit and effort should always yield more.
At the table, phones often come out before the conversation really begins. Notifications pull us away. Photos get taken. Messages get answered. We sit beside one another, but not always with one another.
We’re not just talking about baseball. We’re talking about sport culture. When organizations treat performance like zero-error mode, they fuel perfectionism. They weaken trust, silence learning, and fracture teams. But when culture allows for growth, supports players after mistakes, and trusts the process, development happens. Teams become real teams. Players feel connected. Performance improves.
Cheer effort and resilience, not just results
Psychologically, being watched can alter how we see ourselves. When we know we’re being observed, we become more self-conscious, more controlled. We second-guess our choices, monitor our behaviour, and attempt to manage how we are perceived. For many young people, this constant awareness contributes to a growing need to be flawless in how they perform, and in who they appear to be.
Because kids aren’t born perfect, and they are not meant to be. Growth requires room for missteps, reflection, and second chances. Today’s teens are coming of age in a world where even small mistakes can be captured, shared, and permanently stored. However, that wasn’t the world most adults grew up in. Before smartphones and social media, us adults had the safety of forgetting. The freedom to make poor choices without an audience. The chance to learn who we were without being constantly observed.
