Thrillable Hours:
Michelle Dean, Writer

Thrillable Hours - Careers for Lawyers Q&AWelcome back to Thrillable Hours,  my interview series about alternative careers for lawyers

Unlike some of the other interviewees, Michelle Dean currently wears many hats and is in as relevant a state of transition as most of us who have moved from career to career. With an incredible array of projects on her plate and a seriously impressive lexicon of prior work, I am excited to feature her because she represents another category of former lawyers: she has used each new decision and writing as a stepping stone to somewhere else.

One of the more interesting and quirky writers I know, I first encountered her writing on the Awl (her “Canada! How Does it Work?” post remains the best synthesis of our current electoral climate that I’ve read), and have followed her Tumblr since. Finishing a thesis, writing controversial pieces about Bridesmaids and (successfully) applying to grad school. I’m sure you will also enjoy her great writing, photos from New York and Toronto and no-nonsense answers to the Thrillable Hours questions.

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Interview with Michelle Dean

What made you decide to leave the traditional practice of law and become a writer? Was there a particular moment that catalyzed the decision for you?

I talked about leaving practice for a long time before I actually did it, and I have to admit, even then the main catalyst I was stealth-laid-off. Which at the time was something of a blessing, as I’d been thinking of returning to school that fall anyway, and I really seemed to need someone to push me out the door. There’s a sort of comfort that attaches to working at one of the big firms; they act as a parent of sorts, they make life easy for you. Not just with money, but by providing a sort of scaffolding of success and value that makes you feel like you have made something of yourself, even if really what you do is correct typos on briefs and deal documents all day.

But from the moment I arrived at the law firm my first year I knew that a lot of the security and self-esteem attached to firm life was a facade. I really loved New York, and thought it could substitute for a while for doing work that I loved. And in some ways it did. I directed some (really bad) plays off-off-off-Broadway, I went to screenings at Lincoln Center, I made a ton of friends, I started writing, a bit. But I literally hated the entire routine of going to work in the morning. I didn’t mind doing work, per se, even a lot of work, in fact my major complaint was that I wasn’t kept sufficiently occupied – I minded having to wear business casual and sit in an office all day to get it done. I minded dealing with the subsection of lawyers who think that their bar membership is license to be as absolutely obnoxious as possible. I minded having people feel entitled to my time even when they had nothing they needed me to do – they just wanted me to wait in case they did. I minded that people seemed upset that I wasn’t interested in the firm as an exclusive social circle. I minded the occasional latent sexism of my peers, and the way in which the culture of the firm seemed to endorse it. I minded watching a lot of smart bright people become grey shadows of their former selves. And while not all of those things were deliberately a pat of the culture of my firm – my firm was run by some good people and I was well-treated there – they made me resent my life more than anyone making the ungodly amounts of money we were should. It didn’t make me a great employee, anyway.

Dylan Thomas' Under Milk Wood, directed by Michelle Dean

Dylan Thomas’ Under Milk Wood, the play that Michelle directed in NYC

I think I could have come around to like practice itself if I’d been allowed to do more of it. I had a couple of small cases that were fun, and I got to work on the Chrysler bankruptcy, that went from zero (i.e. no discovery) to trial in ten days in 2009. I really enjoyed that. But it wasn’t in the culture of the kind of place I was at to be doing that 24/7. So, I needed to go, I know. There was a lot of relief wrapped up in my layoff.

What do you find most fulfilling about your current job?

Well, at the moment, I don’t really have a job. I’m wrapping up one degree and heading on to the next. I freelance write a bit, and I’m going to school in the fall (again) to learn how to do it better, and try to make a career of that. We’ll see how that goes.

I do think it’s refreshing to spend as little time as I do, currently, doing things to please other people. I went to law school partially because I thought it would please others that I was there, not because I really dreamed of being a lawyer. I feel like this transition period is something of a second early-twenties, where I’m sort of feeling out how the phase of my life where I don’t hate what I do is going to go. Except now I have better furniture than I did then.

How does your continued legal education inform the way you see the world today?

I’ve puzzled over this question a bit. The truth is that the architecture of principled reasoning – which is I think the main thing one “learns” in law school – came to me from a career in (nerd alert) undergraduate debating. In some ways legal education left my worldview pretty much undisturbed, just helped me to organize it a little better. And that’s been helpful, of course – I like to joke that my life thus far has been an effort to monetize the fact that I don’t seem to think like everyone else, which usually gets me more trouble than money.

NYC, photo by Michelle Dean

New York’s skyline from the Brooklyn Promenade

You are currently pursuing an additional degree in constitutional law. What made you decide to take your law studies further, and what do plan to do once you obtain your degree?

I had always thought about going back to teach law. I taught legal methodology during my law degree, as well as a small tutorial section of McGill’s sort of “intro to legal theory” class taught to first years. And I loved it. I also do, even after the mixed experience of practice, like the substance of the law a great deal. I am mostly interested in feminist theory and constitutional law, so I just headed in that direction, and I’ve had a wonderful time at U of T, working with Jennifer Nedelsky on a thesis about freedom of expression, the internet, and the feminist blogosphere that I’m rather proud of, actually.

I had thought I’d do a doctorate next year, but then this opportunity at NYU’s Literary Reportage program came up, and I looked at the job market for legal academics, and I thought about the fact that I never clerked or did any of the standard law-prestige things that law professors seem expected to do (no Oxford, no Harvard), and I decided it might make sense to develop this writing sideline where I’d been having a lot of success. One of the things my LLM year has made me think about specifically is how over-specialized legal academic language, and even legal language itself, can get. It seems somehow fundamentally undemocratic to me that we’ve let our concern with maintaining professional boundaries make the law so inaccessible to regular people. And I’m interested in writing about the law in ways that sort of bring it back down to The People, whoever they may be. That’s sort of what appealed to me about teaching too – I like explaining things. And I think that I’m much better at explaining the ideas of others than I am at coming up with some of my own. So the academic career track has been shelved – for the moment.

Toronto's skyline at dusk, photo by Michelle Dean

Toronto’s skyline at dusk

What do you have to say to those who tell me lawyers can’t have fun?

I think there is this bizarre self-defeating myth that you have to put your nose to the grindstone in order to “pay your dues” to the profession, and once you’re all current with your account, so to speak, you’ll have this wonderful well-paying career and the fun can wait until then. Of the many things that were leading me out the door of my law firm, post-2008 election I came across a quote from Michelle Obama, where she was talking about choosing to leave her firm after a friend died. “If I died in four months,” she says she thought, “is this how I would have wanted to spend this time?” I think that’s how even lawyers have to look at it. All this waiting for some day when your house will be nice enough and your kids will be well enough all – well, I kind of think it’s bullshit, to be frank, and anyway that day is never coming. You have to try to live a life where you aren’t hating every second of it in service of some future goal. Which is both easier, and harder, than people think.

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Michelle Dean graduated from McGill Law in 2005, and spent the next five years practicing, in desultory fashion, at a gigantic anonymous law firm in midtown Manhattan. This past year she has been studying for an LLM at the University of Toronto. When not complaining about writing her thesis on Twitter or Tumblr, she’s been doing a fair bit of freelance writing at places like The Awl, Bitch, and The American Prospect. This fall she’ll be in school again, this time at NYU’s Arthur L. Carter Journalism Institute doing an MA in Journalism on their Literary Reportage track.