Escaping from Alcrataz

When I was sitting where you are, back in 1989, I would’ve told you that I wanted to be a lawyer. I didn’t really know what lawyers do all day, but I knew they first had to go to law school, and school was familiar to me.

I had been competitively tracked from middle school to high school to college, and by going straight to law school, I knew I would be competing at the same kinds of tests I’d been taking ever since I was a kid, but I could tell everyone that I was now doing it for the sake of becoming a professional adult.

I did well enough in law school to be hired by a big New York law firm, but it turned out to be a very strange place. From the outside, everybody wanted to get in, and from the inside, everybody wanted to get out.

When I left the firm, after seven months and three days, my co-workers were surprised. One of them told me that he hadn’t known it was possible to escape from Alcatraz. Now that might sound odd, because all you had to do to escape was walk through the front door and not come back. But people really did find it very hard to leave, because so much of their identity was wrapped up in having won the competitions to get there in the first place.

There’s a lot of wisdom in those sentences above. I took them from a transcript of a Commencement speech that Peter Thiel gave. He is a co-founder of PayPal.

I’m writing this for a few reasons, First, the speech made me think about the Jeff Bezos view that “we are our choices.” The road you don’t take, in Peter’s case, a high-powered law firm job, is often more important than what you do take.

Second, choices have costs. To “un-brainwash” yourself and get off a corporate track requires a great deal of inner strength. Some family members and friends will think you’ve lost your judgment, and some may even judge you for your lack of wisdom and being a quitter.

Third, it reminds me of my own choices, such as leaving my investment banking job, quitting Bain & Co., and starting Kepha. Those were excruciatingly difficult, but I no longer cared about what people thought.

Fourth, difficult choices can cover career topics, but, also, they can cover decisions about relationships. Has anyone ever agonized about initiating a break-up? Sometimes, relationships can be as suffocating as career choices that don’t mesh with one’s values.

There’s a lot there in Peter’s speech. I encourage you to read it. Here again is the link.


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