The Page 217 Mistake

“You’ve gotta live to learn. You’ve gotta crash and burn.” – Darius Rucker

Every career has moments where one mistake feels like it could end everything. This was mine.

We’d spent three straight weeks of all-nighters chasing a $1.2 billion deal for one of our best private equity clients. No sleep. Endless revisions. By the hour, terms shifted—rates, covenants, leverage, add-backs.

On judgment day, we walked into DLJ’s commitment committee. Picture the Wall Street Avengers wearing Hermes ties: Tony James, Bennett Goodman, Ken Moelis, and more, lined up in the boardroom. I was in my twenties, running on fumes, clutching the freshly printed 250 page books—so detailed our analysts had literally vacuumed the pages to remove stray paper chads.

I had five minutes. Five minutes to blitz through investment highlights, projected returns, why our client could drive value. Every word mattered. No wasted motion. We crushed it. The committee loved the deal.

As we left, Tony James put his arm around me. “Page 217,” he said. “The amortization schedule is wrong.”

My stomach dropped. Blood drained from my face. I felt like I was going to pass out. This was it—career over before it really began.

Then he continued: “Doesn’t change the returns. Fix it and get it back to me. Great job.”

Grace. That’s what he showed me. He could have wrecked me, but instead he built me up. That lesson stuck: people giving 100% don’t need punishment for mistakes – they need support to come back stronger. That is the test of true character.

That day, I learned the kind of leader I wanted to be.

He could have ended me. But then again… he didn’t.