Welcome back to Thrillable Hours, my interview series about alternative jobs for lawyers.
I first came across Matt Levine’s writing over at Dealbreaker in 2012, as I was traveling and eating. While I wasn’t wistful for my former corporate law career, I still wanted to keep up with financial news. Matt’s writing style — funny, intelligent, and thoroughly able to see the forest through the trees — was why I started reading Dealbreaker. It’s also why I moved with him to Bloomberg when he started blogging for them in 2013.
His pieces are approachable and interesting while tackling extremely complex topics. A former lawyer and finance guy, he is able to provide important background to the current news. He delights in sarcastic footnotes. And he’s even got his own Twitter bot that someone created, who is learning to talk by reading everything Matt Levine writes. You know you’ve made it when…?
I realize that not all my readers enjoy reading about credit-default swaps or Argentina’s sovereign debt saga, but I think anyone can learn from the skill of taking complex problems and dissecting them to make them less opaque. This is what Matt Taibbi is known for with US politics and the financial crisis, and why I enjoy Matt Levine’s writing regardless of where he’s employed.
Per the New York Times, who ran a profile about Levine in October 2020, “there’s no other writer quite like Mr. Levine, a former Goldman Sachs banker whose deadpan style mixes technical elucidation and wit. And, to wit, the article gives an example: from a Citigroup lawsuit:
“He once took a term that appeared in a lawsuit — a “cash-settled forward purchase agreement for Citigroup shares with downside protection in the form of a put option at the same price as the forward” — and gave it the acronym CSFPAFCSWDPITFOAPOATSPATF. He makes readers feel in on the savage joke that is late capitalism.”
In that same article, the Times goes into Levine’s routine, noting that he gets up at 5am EST, looks at what’s going on in the markets, scrolls through his inbox and checks in with early-to-work traders before starting to write. His column, clocking in around 5,000 words usually, gets sent off to his editor and normally goes out around noon EST.
His answers about jobs for lawyers, leaving the law, and advice for those who want to do the same, all below.
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Alternative Jobs for Lawyers: Q&A with Matt Levine
What made you decide to follow a less conventional path than typical law school graduates? Was there a particular moment that catalyzed the decision for you?
It was all pretty path-dependent for me. I went to work as a corporate lawyer in 2005, and at the time corporate lawyers all wanted to be investment bankers. (Do they still?) So after about a year and a half, a former colleague who had left to be an investment banker called and asked if I wanted a job. And I said “is it better than this job?,” and he said “it’s a little better than that job,” so I took it. And I was an investment banker for four years. I guess that is actually a pretty typical path for a law school graduate, or was in 2007.
But then I got sick of investment banking too. I had always vaguely imagined myself as a writer, without doing anything about it. And a random combination of factors — I was trying to quit banking, the financial blog Dealbreaker had a job opening, and I knew some people there — led me to fall into financial blogging. And I turned out to be okay at it, and after about two years I was hired at Bloomberg View and have been here ever since.
So I am sort of a terrible story: A lot of luck was involved in each of my career moves, and honestly the “particular moment that catalyzed the decision for me” probably occurred months after I started at Dealbreaker. I went into that job thinking “well this will be a weird experiment and maybe it will work!” And my first weeks there were just abjectly terrifying. And then after a while I was like “oh wait this kind of does work,” and it became unbelievably fun.
What do you find most fulfilling about your current job?
I get to think and write about things that I think are fun! That’s the main thing. Unlike in law and banking, I don’t really get assignments or have tasks or whatever. I just wake up and try to find things that interest me, and that I think will interest my readers. In a weird way that feels more high-pressure than my law and banking jobs: I can never fall back on just checking off a list of tasks; I have to come up with something new every day. But it’s definitely the most fulfilling part of the job.
Also having readers — knowing that strangers are interested in what I have to say — is very fulfilling. I am constantly amazed when I write something that I think will amuse only me, that appeals only to my narrow weird combination of interests, and someone will email me to say “I loved that part.” I love when I find out that important financial-industry people read my column, but I also love when random people email to say “I don’t work in finance but I read your column every day because it’s fun.” It’s always incredibly gratifying to hear.
Do you have any advice for professionals who are interested in leaving conventional private practice but concerned about what is out there?
Honestly my first piece of advice is that if you want to leave law for something weird and risky, you should save a lot of money first. That’s what a law degree is (often) good for. I don’t really have regrets about working at a big corporate law firm and a big investment bank, in part because I learned a lot, but also because they provided some financial cushion that allowed me to take risks later on. I think that, for instance, if I had started in journalism in a more conventional way, I would have had a less fun and interesting career, because I’d have to be more conservative in my journalism career choices.
Otherwise, I don’t know. I talk to a lot of young people about questions like “should I go to law school” or “how can I transition from law to finance,” and the impossible question I always want to ask them is: well, what are you good at?
I think, for instance, that in the transition from law to finance, people who are good salespeople and people who are good confident analytical decision-makers, and people who are good creative issue-spotters, can all be very successful — but those are very different skills, and they should all be looking for very different roles in finance.
And you ask a 23-year-old “which one are you,” and they have no idea.
They’re good at school, and socialized into some standardized career paths, and trained to assume they can do anything they set their mind to. It is so hard to know this central fact about yourself until you have worked for a while and just gotten a sense of where your real skills are and what you are bad at and don’t want to do any more. That self-knowledge is also very easy to avoid: You have a job, and you just try to get good at the things that the job requires.
But — in my experience, having done both — it is much more fun to find a job that requires the things you are good at.
How did your legal education inform the way you see the world today? Do you still identify yourself as a lawyer?
I try to avoid “identifying myself as a lawyer,” in part because that was a weird and stigmatized thing in banking. People would introduce me to clients as “this is Matt, he’s a lawyer,” and I’d bristle: No, I was a banker with a law degree! Very, very different.
But deep down I’m a pretty lawyery lawyer. My work is very legally driven; I spend a lot of time writing about legal issues and reading legal documents, and I’m well aware that my legal training is part of what makes me able to do my job the way I do. Also my wife is a real lawyer so I get to talk to her about legal stuff sometimes.
One pet theory that I have is that law school tends to turn people into legal realists — that is, to make their thinking in some ways less legalistic. Investment bankers are always asking lawyers “can I do ____,” and the lawyers are always answering “well that’s a nuanced question.”
My old colleague Bess Levin, who is not a lawyer, would sometimes see weird lawsuits and ask me “wait, can you really sue someone for ___?” And I’d say “you can sue anyone for anything! But you might not win.” That is an obvious point, but that general sense of the law as a nuanced and human a system for handicapping the potential decisions of government officials, rather than a list of black-and-white rules, seems really useful in a lot of contexts, certainly in writing about finance. Also it still strikes me as accurate. And it’s a mindset you develop in law school, and in legal practice.
What do you have to say to those who tell me lawyers can’t have fun?
That strikes me as mostly accurate, yeah.
More on Matt Levine in this Billfold interview about how he handles money as a financial columnist, and in this Business Journalism interview about his transition from finance work to finance journalism.
Matt Levine is a Bloomberg View columnist writing about Wall Street and the financial world. He is a former investment banker, mergers and acquisitions lawyer, and high school Latin teacher. Levine was previously an editor of Dealbreaker. He has worked as an investment banker at Goldman Sachs and a mergers and acquisitions lawyer at Wachtell, Lipton, Rosen & Katz. He spent a year clerking for the U.S. Court of Appeals for the Third Circuit and taught high school Latin. Levine has a bachelor’s degree in classics from Harvard University and a law degree from Yale Law School. He lives in New York. You can find his columns on Bloomberg View here, and he is also very active on Twitter.