I grew my hair long for the first time in my last year of high school. Rock and roll had a lot to do with it. Heavy metal did the rest. And underneath, maybe, a first small claim of independence, the kind you cannot put into words at eighteen but you can wear.
Those were the years of albums played on repeat and band posters studied like maps. Every singer and guitarist I admired had hair down to his elbows. Growing mine felt like joining something.
I was not as confident as I am today. At eighteen I had the long hair without the attitude, which is a bit like having a guitar without knowing how to play it.
Then some girls in my class asked me why I did not cut it.
I ran the numbers the way an eighteen-year-old runs them: if girls are asking, girls must prefer it short. So I cut it, expecting some return on the investment.
The only compliments came from my Latin and Greek teacher. Not exactly the audience I was aiming for. The girls, in the meantime, learned an important lesson: an interested man will do crazy things for you.
The hair stayed short for a long time after that. Then thirty arrived, and with it what I now call my first sabbatical: a few months in Scotland thanks to a scholarship, my first Camino de Santiago, my master’s at Harvard, and a love that would teach me more than I could have possibly imagined. New libraries, new roads, new weather, and a version of me under construction. It felt like the right season to let the hair grow again, so I started in March 2015. At graduation, it touched my shoulders.
Nobody had asked me anything this time. Maybe that is why it felt right.
From there I kept it long. Long hair on the Camino, long hair in lecture halls, long hair in meeting rooms and networking nights where everybody else seemed to share the same barber. You know, long hair in a suit is kind of cool. It is unexpected, and I like it. But it has a price: being acknowledged for your appearance before anything else. A lawyer with hair past his shoulders gets noticed before he says a word.
The good part is that people thought they were judging me, while I was the one judging them. When they looked at me the wrong way, or made a comment on my hair, I knew they were prejudiced. Which meant I should not spend much time with them. Years as a mediator taught me that changing someone’s principles is nearly impossible, so better not to waste energy sowing asphalt.
At thirty-three, the whole thing turned biblical. Thirty-three, long hair, a beard: history offers one very famous precedent.
My girlfriend at the time came from a totally different culture and had never set foot in a church. At some point, mostly because of my influence, I walked her into one. She studied the place in silence, then leaned toward me and asked, in complete seriousness, who was that man who looked like me, the one with pictures everywhere.
I have received worse compliments.
Then I went back to Big Law, and the hair became a topic. In a profession where even ties follow rules, hair past the shoulders reads like a manifesto. Mine was never meant as one. It was just mine. That, apparently, was hard to explain.
Here is the confession: at some point I was inclined to cut it. Really. I was ready. Life had funnier plans.
First came a chat with the Managing Partner. One day he asked me: “What image do you think you give to others?”
“Well,” I answered, “you should ask them.”
He took it well. Better than that: the exchange entered his repertoire. For years, whenever the conversation turned to diversity, he would tell the story and ask the room: “How can we speak about diversity if we cannot even accept a lawyer with long hair?”
With a couple of young partners, though, it went differently: “You have to cut your hair.”
Not advice. An order. And unless you have worked in Big Law without being an equity partner, you cannot know what hierarchy really means there. But orders trigger something older in me, some ancient stubbornness I have stopped apologizing for. I could have been fired, but there was no way I was going to cut my hair. So the scissors stayed in the drawer for years.
In the end, the only one with the authority to cut my hair turned out to be AC Milan.
Years before, somewhere in the middle of the lean seasons, I had made a promise: the day Milan returned to the Champions League, I would cut it. Every fan makes deals like this, and they feel cheap on the day you sign them. Then Milan went and did it.
So one morning I showed up at the office with short hair. Nobody saw it coming. Life changes like that, when nobody expects it.
Thank heaven Milan did not win the Champions League the year after. By the unwritten rules of these deals, I would have had to shave my head.
That is pretty much the whole story. Looking back, though, the hair was never really about the hair.
At eighteen I cut it because some girls asked. In Big Law I kept it because two partners ordered. Two opposite moves, same mistake: I was answering to everyone but myself.
The hair of the sabbatical belonged to another category. Nobody asked, nobody ordered, nobody bet. It grew at its own pace, from one spring to the next, while I walked, studied and slowly figured out who I really was.
These days I wear it kinda short. But “Mai dire mai”, as we say in Italy. Never say never. All it takes is another promise worth keeping…
P.S. Past a certain age, long hair can become complicated for a man. But while you’re young, I recommend wearing it long at least once in your life. Learn what it means to be judged by your appearance. Learn what it means to sleep on it the wrong way, fight the wind, lose twenty minutes after every shower, and occasionally wonder why you are doing any of this. You will never look at a woman drying her hair in quite the same way again. Sacrifice, like so many things, remains invisible until it crosses your own path.
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The hair may be shorter, but the attitude is pretty much the same….
