Asked And Answered: 4 Tips For Leaving The Law

Here’s some practical advice—from someone who left the practice of law and has no regrets.

(photo by Jacobs Stock Photography Ltd. via Getty Images)

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Twenty years ago this month, I wrote my first post as a legal blogger, which sent me on an unusual professional journey. A few months after revealing myself as the author of the pseudonymous Underneath Their Robes blog, I left behind a promising career in the law to become a full-time blogger. And that’s how I’ve been making a living ever since (aside from a two-year detour into legal recruiting).

As a current legal journalist and former legal recruiter, I have firsthand experience with what it’s like to transition out of law into a different but related career, one that draws on a legal education and experience but doesn’t involve billing hours. And I also know about the subject from having written about it. For years, I wrote and edited posts for the Career Alternatives column at Above the Law, and one of my first freelance piece for a print publication was an article for the New York Observer, Do You Believe In Life After Law? (profiling lawyers who left the profession for baking, banking, catering, fiction writing, and standup comedy).

Not surprisingly, I’m frequently asked for advice on how to transition out of law—sometimes by lawyers who are downright unhappy, and sometimes by lawyers who like but don’t love what they do (which is how I’d describe my former self). It’s also a common subject raised by founding members of Original Jurisdiction during their one-on-one calls or coffees with me.

Since I unfortunately don’t have the time to speak to every individual who asks me for my thoughts on this subject, I thought I’d write about it for my advice column here at Original Jurisdiction, Asked and Answered. If you have a question for a future edition of A&A, please email me at davidlat at substack dot com, subject line “Asked and Answered: [your topic].”

Here’s today’s question (a composite of inquiries I’ve received over the years):

Dear A&A,

I’m a junior associate in Biglaw. I haven’t been here that long, but I’m already pretty sure that I want to leave—not just my firm, which is fine as firms go, but the practice of law.

I realize that being a junior associate at a firm often involves a lot of drudgery. But when I look ahead to what midlevel or senior associates are doing, or even what partners are up to, their work doesn’t appeal to me either.

And there’s no other job within the law that cries out to me either. I’m not one of those people who went to law school with a plan like “work in Biglaw for two or three years, pay off loans, and become a [prosecutor/public defender/public-interest lawyer/law professor].”

To be honest, I went to law school without a clear sense of what I wanted to do with my J.D. degree. And maybe that explains my current predicament.

I feel a bit lost. And yes, I do have outstanding student loans. Please help!

Yours truly,
Bewildered in Biglaw

Thanks for your message, Bewildered. If it’s any consolation to you, you’re far from alone. Here are four steps I’d recommend to someone in your shoes.

1. Get yourself in good financial shape.

When law students or lawyers tell me that they’re interested in an alternative career and ask me for one piece of advice, I often quip, “Marry rich.”

It’s a joke, but there’s a grain of truth to it. Very few alternative careers will pay you as handsomely as practicing law—especially since you work in Biglaw, and especially when you’re just starting out in a new field. In 2006, my first full year as a blogger/writer, I earned less than $50,000. That’s less than what I earned as a law clerk or an assistant U.S. attorney, and far less than what I earned in 2002, my last full year at Wachtell Lipton (more than $270,000, in case you were wondering—I looked up my earnings history on the Social Security website, which can be fun to do).

I don’t know your financial situation—you mentioned student loans, but I don’t know if you have a mortgage, a spouse or kids to support, elderly parents who need help—so I’ll speak in generalities. What I’d recommend is that while you figure out what to do next, get your financial affairs in order. Pay off as much of your educational debt as possible, don’t on additional debt (like a mortgage), and save as much as you can.

When you’re working long hours in a stressful Biglaw job, it’s only natural to want to “treat yo’ self” when not toiling away—with gourmet meals at high-end restaurants, lavish vacations, and designer clothes. If you’re seriously thinking about leaving the law, though, do your best to avoid these temptations—and try to put yourself in a situation where you can get by with a modest income, or maybe even no income, for an extended period of time.

2. Figure out what you want to do next.

This is easier said than done, but there are multiple things you can try. For example, you can certainly take a career-aptitude test, which can be easily found online; I didn’t do this myself, but I have met others who found it helpful.

My path out of the law was fairly common: I had a hobby or side hustle that gained traction. I started a blog, it garnered traffic and notice, and that gave me the confidence to think that I could quit the law and make it as a writer. (It also helped that I had no student loans, plus savings from my years as a lawyer—see point #1, supra.)

So… just try stuff! If you’re interested in journalism, look into doing some freelance work (consistent with your firm’s policies about outside writing). If you enjoy baking, experiment with recipes on the weekends; maybe you’ll make treats for family and friends, and it will expand from there. If you aspire to a career as an artist, start taking some classes or producing some art, and see where it takes you.

If you want to become a novelist, join a fiction-writing workshop or begin working on a manuscript. Follow in the footsteps of Helen Wan, author of The Partner Track, and Allison Leotta, author of the Anna Curtis series of novels. They worked on novels while juggling demanding jobs as a corporate lawyer and federal prosecutor, respectively—and after encountering success, they became full-time writers.

You might say, “I bill 2500 hours a year—I don’t have time for hobbies!” I worked at Wachtell, so I feel your pain.

You might have to transition to a less time-consuming legal job, one that allows you to explore outside interests, as a way station en route to leaving the law entirely. That’s one reason I went to the U.S. Attorney’s Office in New Jersey: it offered better work-life balance than the S.D.N.Y. and E.D.N.Y., and I could focus on appellate work—which gave me ample control over my schedule.

3. Get some help.

In my recent podcast interview of Bryan Garner, the world’s leading legal lexicographer, his response to my closing question about advice was to remember these words: ”I need your help.” And don’t be afraid to use them.

Bryan’s wise advice definitely applies in the context of careers. If you don’t even know where to begin in thinking about your next act, there are professionals who are well-equipped to guide you.

It could be beneficial to speak with a career coach. Two coaches with expertise in the legal space specifically are Jordana Confino, a Yale Law grad and lawyer turned coach and consultant, and Keira Chassman, LCSW, who works as both a clinical therapist and legal recruiter. And I know there are many other excellent coaches; Keira and Jordana just happen to be two coaches I was in contact with recently (Jordana as a podcast guest). Feel free to mention other coaches in the comments to this post.

There are also online resources specifically aimed at lawyers who are thinking of moving on from the law. For example, check out the websites of Leave Law Behind and Ex Judicata—both of which also offer coaching, if you’re interested.

4. Don’t burn bridges as you leave the law.

During my time at Above the Law, I enjoyed reading and writing about bridge-burning departure memos. But while they might be fun to read—and fun to write, in the moment—they could turn out to be professionally problematic if you try to return to the law.

And yes, it might very well happen. Careers are long. If you’re disillusioned about practicing law right now and eager to leave, you might find the idea of returning to be impossible to imagine. But you might leave the law and discover that the grass on the other side is not, in fact, greener. You might change as a person, or your personal circumstances might evolve, in ways that could make returning the right decision.

Almost two decades removed from practice, I have no plans to return to the law—and I don’t know that anyone would have me if I did.¹ But I’ve met lawyers who have returned to practicing after leaving for careers in journalism, finance, and the entertainment industry, among other fields. And when they did, their good relationships and reputations in the legal community were enormously helpful.

So that’s my advice for lawyers who are thinking of making their great escape. Readers, anything you’d like to add?

[UPDATE (6/19/2024, 12:08 p.m.): For a fantastic follow-up discussion from Sarah Isgur and David French, check out the latest episode of Advisory Opinions (starting around 39:40). They offer their own advice, as former practicing lawyers, on how to transition from law to other endeavors.]

1. But I still keep my New York law license active—mainly to keep my mom honest when she tells people, “My son is a lawyer.”

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