JoJo poses a good question in a request for a post:
Do you find having a J.D. in your back pocket allowed you to pursue other ventures like sailing and writing, both because it provides a financial safety net and because it is proof of your professional success? Do you think you could have been a sailing coach without having been a lawyer first?
As usual with my readers' good questions, I'm not sure I have a great answer. I think the best answer to this is sort of yes, and sort of no.
In high school we got something like 100 characters to go under our senior picture in the yearbook. I remember a lot of conversation and thinking about how to use those precious 100 characters. Which private jokes would go in? Capital or lowercase letters? Whose initials do I want in there? Did I want to put in a quotation or have all of the words my own? Eventually, I decided to include a quote, and that created a whole slew of additional questions. It may be dorky to admit this (or maybe it's cool -- I've never really known which) but I was a big Steely Dan fan in high school. They were my favorite band and I had all their albums. So I wanted to use a Steely Dan lyric. And after lots of concentrated listening and thinking the one I settled on was this, from Any Major Dude: "You can try to run but you can't hide from what's inside of you." That's under my yearbook picture, amidst the initials and the private high school jokes.
Now, in retrospect, I am kind of amazed by that decision. Because the older I get the more sense that little snippet of Steely Dan lyric makes. Was I really so wise back then? Of course not -- look at all the stupid things I did subsequently. Look at all the running I did. Still, I picked those words and I'm glad I did. I can imagine that my teenage self was an old soul.
So back to JoJo's question. Sailing and writing are inside of me, deep. There aren't many things I've loved for as long as I can remember. My family, being outside, Maine, learning about people, looking closely at things (especially bugs), reading, my best friend Autumn, sailing, and writing. I think in many ways I just gave up running away from the kind of life I most want.
But I really liked law school. I really liked practicing law. It's very interesting. It's fun. It's not how I want to live, and I never loved it with the kind of deep and permanent love I have for the things above. I think some of the things I liked about it aren't good for me. I'm already competitive by nature and I'm happier when I feed that carefully and don't let it run rampant. As a lawyer, you're rewarded for convincing people that you're smarter than the other people in the room. That's a bad incentive system for me -- I'm too inclined to do that already, and I don't like it about myself. I'm trying not to have it permeate the way I see the world. (We'll set aside for another day the comparison to coaching, which a friend pointed out may not be so different from some of things lawyers need to do....) As a lawyer, quickness and a specific kind of logical agility and verbal precision matter a lot. Those things are fun for me, too. But they're distancers. It's not necessarily the kind of sharpness I want to hone any further.
The ugly truth to JoJo's question is that there are things about having a law degree that make this life decision easier for me. I try to notice when I want to bring it up in conversation, and pay heed to what is driving that impulse. I didn't mention it for a long time when I sat on the book selection committee with a bunch of professors at the college, but finally in a meeting I found a particular professor so insipid and condescending that I made a gratuitious reference to law school. I feel ashamed and embarrassed about that. It was clumsy shorthand intended to convey, "I am not dumb, and you had better not condescend to me." But instead I felt immediately like I'd been caught up in a stupid kind of credentialism that irritated me about the professor I was trying to rejoin. To the extent I keep the law degree and time spent practicing law in my back pocket, it's for that purpose: as a golden ticket to people who I think of as equals, to show them I'm not "just" a sailing coach or "just" a writer. I hate that impulse. It stems from snobbery and low self esteem, and when I have the impulse to mention law school or practicing law I pay attention to whether it is really relevant before I open my mouth. But sometimes I do it anyway.
Last night I had dinner with a friend who's a serial entrepreneur and a very successful tech thinker. He said something about a venture fund he's involved with and started to explain an aspect of it to me, and then said, "oh, you know, you were a lawyer, I forgot," and went on with the point of his story with a wave of his hand. And in that moment I felt a tiny bit of pride. That's what having a law degree does for me -- it conveys to people that I know more about the world and have more kinds of competencies than the particular ones I'm using right now. Of course that's true of everyone. But there's something comforting about having something that other people respect and value, even if you discover it's not what you most deeply love or want to spend your time doing.