They'd nodded along every time we talked about ego. They could practically quote the lesson back to me. Stay humble, stay teachable, don't let your pride get in the way of your growth. They said all the right things.

But the moment the feedback landed on their work? The ego showed up like it had never left. Defensive. Deflective. A wall went up, and nothing I said after that point got through.

And that's when I realized: this wasn't their failure. It was mine.

I'd been so focused on mentoring my students, on saving them from the headaches and growing pains I went through as a young designer, that I'd been catching them before they ever hit the ground. Every time I saw a mistake coming, I'd step in. Every time a project was headed sideways, I'd course-correct before they felt the impact. I thought that was the job. I thought that's what good teaching looked like.

What I was actually doing was building students who had never failed. Who had been told they were doing good work so consistently that they had no practice sitting in the discomfort of falling short. They understood humility as a concept. They had never needed it as a survival skill.

That student, the one who couldn't hear the feedback, was a mirror. They showed me exactly what I'd been creating.

Seneca's Mistake

Around the same time, I'd been thinking about Seneca and Nero. It's a story that's always stuck with me, but it hit different this time.

Seneca was one of the greatest Stoic philosophers in history. And he was Nero's personal tutor. He taught the young emperor ethics, restraint, wisdom and for a while, it worked. Nero's early reign was actually considered promising. People credited Seneca's influence.

But Seneca was so present, so involved in Nero's decisions, that Nero never developed his own judgment. The wisdom was always borrowed. Performed. When Seneca was eventually pushed out, Nero didn't just stumble. He became one of the most destructive leaders Rome ever saw. The foundation wasn't his. It had been loaned to him, and when it was pulled away, there was nothing underneath.

I kept turning that over in my head. Because I saw myself in Seneca. Not the brilliance, obviously, but the mistake. The well-intentioned mentor who was so close, so protective, that the student never had to build something of their own. I was handing my students my judgment instead of helping them develop theirs.

The Video That Confirmed It

Then (and the timing felt almost too perfect) I watched a Ryan Holiday video about bad advice on the internet. He was breaking down ego, referencing a POTUS quote: "Show me someone without an ego and I'll show you a loser." And Holiday pushed back with Epictetus: it's impossible to learn that which you think you already know.

That line hit me right in the chest. Because that was my student. Sitting in my classroom, thinking they already knew. Not because they were arrogant people, but because I'd never given them a reason to question it.

Holiday talked about Marcus Aurelius writing Meditations as a daily discipline of fighting his own ego. Not because he'd conquered it, but because the fight never ends. Aurelius was the most powerful man in the world, and he still had to remind himself every single morning not to believe his own mythology. Humility wasn't something he achieved once. It was a practice.

And then Holiday drew this contrast between ego and confidence that crystallized everything for me. Confidence is knowing what you're capable of because you've been tested. It's paired with self-awareness, with an understanding of your weaknesses, with humility. Because humility is what allows you to keep getting better. Ego is the thing that gets between you and growth. Between you and other people. Between you and reality.

He referenced that Zen parable about the cup. If it's full, nothing more can be poured in. If it's empty, there's room.

I'd been filling my students' cups for them. And then wondering why they had no room left to receive.

What I'm Changing

I teach at JPCatholic, and everything I do in my classroom runs through truth, beauty, and goodness. That hasn't changed. I still tell my students on day one: you never have to figure this out alone. Find a mentor. Ask for help. Lean on people who've walked the road you're on. I still share my own story. The hard transitions, the self-doubt, the nights I cried wondering if I was cut out for this work. I share it so they know the struggle is normal, not a sign they're in the wrong place.

But I've stopped trying to prevent the struggle.

I'm leaving room now. Room for the project to go wrong. Room for the critique to sting. Room for them to sit with I thought this was good and it wasn't and have to figure out what to do next without me handing them the answer.

It's the hardest shift I've ever made as a teacher. Every instinct says step in. I know what's coming. I've been there. I can see the mistake before they make it. But I think about Seneca and Nero, and I hold back. Because if I keep catching them, they'll never learn to catch themselves. And worse, they'll think they already know how, because no one ever proved them wrong.

That student who couldn't hear my feedback? They weren't the problem. They were the lesson. They showed me that somewhere along the way, in my effort to be the mentor, I'd skipped the part that actually matters most.

You can teach someone everything you know. But if you never let them fail, they'll never know what any of it is for.