The year that almost broke me (and 4 things I learned from it)
In September of 2009, I had the surreal moment of opening a New York Magazine to see a full page picture of my face. At 27 years old, I was - supposedly - the youngest school principal in New York City. I was also (unmentioned in the short write-up) newly divorced, drinking too much, and wearing a brace under my clothes because of mysterious and acute back pain.
Though feeling all too special with my New York Magazine in hand, I was somewhat of a walking cliché. A young college-educated white man with a rather absurd amount of responsibility, an ego that was thriving, a heart that was full of repressed pain, and a body that was already paying the consequences.
And little did I know it was just the beginning.
At 27, I thought I knew what it meant to be a “great leader” within my high-performing charter school organization.
Great leaders worked around the clock. They took decisive action. They took responsibility. In fact, everything that happened on their watch was because of them. They moved with urgency. And perhaps most of all - aside from maybe optimism and enthusiasm - they felt nothing. Certainly not any kind of fear, pain, or uncertainty.
My first year as a principal nearly broke me. I ran a middle school in Brooklyn that served 100% Black and Brown students. Yet, I felt perfectly emboldened to immediately make sweeping changes with almost zero input from staff, students, or families. The backlash was enormous.
In a typical day I was up before the sun, having a pot of coffee for breakfast, and steadying myself for a day of putting out proverbial fires in my poorly run middle school – toggling between phone calls with (justifiably) angry parents, navigating tense, passive-aggressive conversations with staff, and futilely trying to keep a tidal wave of email at bay. But I held my ground. The bad press (NY Post: “Principal Rules with Iron Fist”), staff unionization efforts, distressed students and their families … nothing was going to fundamentally change my course.
I would typically leave the school around 7 p.m. only to go straight to a diner and get my “table for 1” where I would eat my first meal of the day and immediately open my laptop to continue working. Once home, I would drink so that I could get to sleep, and then start the whole thing over again.
By the spring, I had lost 25 pounds and my clothes didn’t fit. I was walking home from school one day when my 58-year-old mom called me to let me know that she had been diagnosed with breast cancer. For the first time all year, I lost it. Suddenly, I was just a human again. One that was scared and vulnerable. At the diner that night, I reached out to my manager to let her know that I might have to take some serious time off to go be with my mom. And she responded right away, supportively.
But by the next morning, I guess that human being had once again given way to the “leader.” I never took a day.
I look back at that 27-year-old with a heavy heart. If I could say anything to him now, I would tell him –
Slow. Down. Dial down the pressure. You think this is all so urgent. You think this is life and death and feel so certain about what must be done. WIth LOVE, I want to tell you from up here in 2026: 1) you will experience REAL life and death. And state tests ain’t it. And 2) your certainty is laughable.
It’s not about you (in a good way). You’re not special. Nor do you have anything to hide or to prove. You have a job that gives you a chance to do something caring and impactful. That’s it. Let the rest go.
No matter how important or high stakes work feels, it’s not the most important thing - and it’s temporary. Your body is not temporary. Your family is not temporary. Take care of what’s real and lasting.
Your head may help you “succeed,” but your heart will help you avoid regret. You don’t have to run away from the pain in your heart. Let it in, and it will guide you.
This advice wouldn’t have just made my life better and healthier, it would have made my school better and healthier. Of course, the 27-year-old me probably wouldn’t have been able to hear any of this. But that’s okay. It’s become my life’s work - and my own path to healing - to help leaders slow down, get in touch with what matters, and gain the kind of perspective that helps minimize regrets.
And even if 27-year-old me wouldn’t hear it, 44-year-old me can still use the reminder.
