The Slow Track To Success

A rant about my misadventures on the "management track"

When I was growing up there was nothing more I wanted than to be part of the establishment. I saw myself wearing a suit, perhaps in a boardroom or skyscraper somewhere, leading an important meeting. It just seemed like something I was meant to do.

I made a lot of choices when I was younger in pursuit of that goal. Yes, I wanted to be a trial lawyer, but more than that, I wanted to be someone polished and articulate. Who looked and acted like a leader. The grown up I envisioned becoming was someone who wore a nice suit and knew a lot about wine.

Somewhere along the way though, I realized that wasn’t me. I’m from an underdog family from an underdog culture. We have never been part of the establishment. Which might be why when I first stepped foot in the corporate world—first at IBM, and then at Sullivan & Cromwell—I just didn’t fit in.

At first I thought it was a race thing. Which it was, partly.¹ When you look at “the establishment” you can quickly see that it’s less about how capable you are, and more about how you fit in. The leaders of the establishment always find ways to jump through verbal gymnastics to justify their existence at the top.

But at the end of the day it’s obvious—they’re better at talking than doing.