When I was getting ready for law school, I watched The Firm. Tom Cruise, fresh-faced and full of promise, with all these big-name law firms throwing money at him like he was a first-round draft pick. A Mercedes. A Rolex. A house. All for signing on the dotted line. Of course, he picked the mob firm in Memphis, but that’s beside the point. I wasn’t dreaming of mob ties, I was dreaming of being wanted.
I thought, maybe they’ll throw money at me too. Spoiler alert: they didn’t.
Instead of Harvard or Yale, I went to American University Washington College of Law. A third-rate law school in a two-law school town. And when I graduated, after adding a cherry on top with an LL.M., no Mercedes was waiting for me. No Rolex. Just a job at a third-party administration (TPA) firm and a Toyota Camry. Starting salary? $35,000. Tom Cruise probably made that every time he blinked.
I spent nine years grinding at two TPA firms, learning the retirement business inside and out. Eventually, I thought it was time to try the law firm path. First stop: a union-side firm where they treated associates the way they thought the employers treated union members, badly. Then came a fakakta Long Island law firm. I stayed for two years, working hard, doing what I thought was the path to success.
That’s when I saw it. The “path to partnership” was a mirage. The first level of “partner” had no vote. No say. Just a different title and maybe a better parking spot. It was like a country club with two entrances, and I didn’t have the key to the one with power.
Worse than the structure was how I was treated. Like a necessary inconvenience. I realized I was never going to be that guy. The law firm golden boy, shaking hands at bar association events, billing hours like it was a religion, kissing the right rings, waiting 10 years to maybe become “non-equity partner.”
I was getting older. The longer I stayed, the more I felt like I was cosplaying a lawyer instead of living like one.
So I jumped. I started my own firm. No partners. No gatekeepers. No fake ladders. Just me, clients who needed help, and the belief that I could do it better. I wasn’t trying to win a corner office, I wanted to build something real. And I did.
Years later, I met Drew Brees and asked him about the Chargers giving up on him early in his career. He just smiled and said, “It all worked out in the end.” That stuck with me.
Because it did. It did all work out. I was never going to be that guy, and thank God for that.
