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Thinking about leaving the law? Here are the top 6 hurdles, as explained by an ex-lawyer

Burned-out, unhappy, or disillusioned lawyers are often held back by their own self-doubt or the doubts of others. But career change is possible, no matter how long or how briefly you’ve been practicing. Read on to learn how to overcome these 6 blocks and pursue the career fulfillment that law school promised you.

Most people think lawyers have everything they could ever ask for—a steady job, a high salary, social status, vacations to Mexico. If you’re a lawyer with a conscientious disposition, you too might tell yourself that you have no cause to complain. But the truth is, if you’re waking up dreading the hours that you’ll bill, the colleagues and clients you’ll see, and the cases that will cross your desk that day, then you do not have everything you could ever ask for.

Something’s not right.

Unfortunately, the social esteem that attaches to lawyers makes it difficult for those in the profession to contemplate, let alone execute, a career change. This means countless lawyers stay in jobs that make them miserable, year after year, until retirement, and never explore a path that will bring them professional and personal fulfillment.

As an ex-lawyer who’s built a career as a paid travel blogger and life coach, I understand the obstacles, both internal and external, that can get in the way of leaving the law. We lawyers are overthinkers, after all, so it’s no wonder that we can talk ourselves out of leaving our comfort zone. I want to help dissatisfied lawyers push past these obstacles and fashion the life they truly desire and deserve. To that end, here I’m going to break down the top six hurdles you must first overcome if you’re thinking of quitting the legal profession.

1. The sunk cost fallacy

Blue notebook with 'sunk cost fallacy' written on the cover, i illustrating how many unhappy lawyers stay in the profession due to this fallacy

Many lawyers stay in the profession just because they’ve already spent so many years of their lives working towards a legal career and they feel that they can’t leave now. Time and time again, I meet with lawyers who are burnt out and disillusioned, but stay in a toxic work situation as a way to somehow justify their years of law school.

Let me give it to you straight: this is not rational.

In fact, if this logical fallacy were tested on the LSAT to begin with, I’m sure less lawyers would stay stuck in a career that doesn’t serve them. (Or maybe not. See the other 5 hurdles to leaving the law below.)

Why is this a fallacy? Let me share an example to show you what I mean.

Suppose your uncle, an avid DIY-er, spent years of blood, sweat, and tears building his own house, only to discover after it was built that the foundation rested on an underground tunnel system and was in danger of collapsing inwards. How would you react if he then said, “Well, I’ve worked so hard to build this place. I don’t care if there’s a whole gopher colony down there, I’m sure not moving out!” What would you have to say to him? Nothing that would validate his perspective, I bet.

Psychologists and philosophers call this pattern of thinking the “sunk cost fallacy.

It’s the idea that your effort spent working towards a goal itself justifies you holding on to that goal, even if it’s no longer serving your needs.

According to Christopher Olivola, author of The Interpersonal Sunk-Cost Effect, people commit the sunk cost fallacy to:

  1. Try to correct the cognitive dissonance between their efforts and expected rewards

  2. As a reaction to regret, or;

  3. To try to convince others and themselves that they’re not wasteful.

For regretful lawyers, there’s good news: you’re not wasteful, no amount of time spent practicing law is needed to justify your efforts, and you’re free to chart a path that works for you, now. Check out how other lawyers overcame this fallacy here.

2. Law school loans

A lawyer trapped by student loans, holding an umbrella with dollar signs falling from it.

Many lawyers take out astronomically high loans to finance their studies. The promise of the law school student debt regime is that your lucrative career as a lawyer will make it easy enough to pay off the debt later. It may seem like a lot now, but just wait till you land that cushy Wall Street job defending bankers from dispossessed homeowners, or that sweet Silicon Valley gig fighting for the rights of the latest tech bro grifter over their erstwhile fans.


Again, there’s good news: lawyers are a sharp and resourceful bunch, and there are plenty of ways for them to make good (and honest!) money aside from a legal career. I advise consulting with a financial advisor to see what your options are and how you can pay off your loans on a reasonable timeline while finding the right career for you. Switching to a new career may mean you’ll have to postpone or reduce your loan repayments for some time. But it’s more than worth it to do so if it means you’ll find a career that lets you form a healthy and happy lifestyle.

3. The golden handcuffs

Golden handcuffs that, ironically keep lawyers from pursuing even more lucrative careers.

It’s law school 101: minimize risk, minimize risk, minimize risk. That’s what you do when you protect your clients from liabilities and avoid longshot legal battles or charity cases. It’s what you chose to do when you entered the legal profession in the first place, rather than pursue another career that would put your mind to good use but without a certain payoff.

But I’m here to tell you something: it’s time to take a risk. If the low-risk life you’re living is eating at you from the inside, then the safety and material comfort it provides just isn’t worth it. I’ve seen client after client who feels hard-pressed to give up the sense of security (financial, never psychological) that their legal career provides.

But the fact is, you don’t need a legal career to make good money. In fact, many ex-lawyers make more money in their new careers than they ever did as lawyers.

The wealthiest among us are not lawyers, after all, but people who thought big and took a leap to achieve their own dreams. So ask yourself, who would you rather be? The entrepreneur running their own company, building varied revenue streams, and facing a new, interesting challenge every day? Or the lawyer processing the entrepreneur’s corporate registration documents? Check out how other lawyers made the transition without going homeless in my guide, here.

4. The identity crisis

Image portraying a businessperson with a question mark instead of their face, symbolizing how a lawyer's identity may hinder the pursuit of fulfilling careers and personal growth.

What’s the first thing you ask a first-time date, or someone you’ve just met at a bar or a networking event?

So, what do you do?

This is how our society defines people, working adults especially: by what they do to put food on the table. But that doesn’t mean it’s how you have to define yourself.

After all, this way of defining oneself was virtually unheard of in societies where there were fewer kinds of labor for people to perform, or where various unmonetized activities were valorized by society at large. The ancient Greeks celebrated Sophocles for his plays, not his work as treasurer of Athens. Scholars in traditional China idolized amateur painters, poets, and calligraphers, without giving a thought to what posts they held in the imperial bureaucracy. They even disdained those who engaged in artistic pursuits for a living!

Point is, this idea—the idea that how you make your money defines who you are and what makes you valuable—is a novel and historically contingent one. It doesn’t have any transcendent rational basis. And that means you, like people from many cultures in different places and times, can reject it in favor of another ideal.

With so many years in law school and the legal profession behind you, you may find it hard to conceive of yourself apart from your professional identity as a lawyer. If that’s the case, then ask yourself: who were you before you practiced law? What did you care about? What do you care about, apart from your work, in the here and now?

Chances are, if you’re already considering leaving the legal profession, you have values that don’t align with your present career. Think about what those values are, why they matter to you, and how you can live them out in your professional and everyday life. This takes some deep work, so feel free to reach out to me here if you have questions about the process.

5. Other people’s opinions

A row of lawyers, pointing and judging one colleague, depicting how others' opinions hinder lawyers' pursuit of fulfilling careers and personal growth.

Here’s one fact that applies to most lawyers, if not most human beings: whatever you think you should do in your life, your mother is going to have something to say about it. Or your father—especially if he is an (Asian) immigrant who struggled to “give you a better future” THAT YOU BETTER NOT THROW AWAY! (No one I know, of course.)

A lot of my clients have friends or family members who feel emotionally invested in their career as a lawyer and just can’t fathom a different life for them. If you float the idea of switching careers, your loved ones might be worried about your future or feel that you’re throwing away all those years working towards your current legal job. (But remember, that’s a case of sunk cost fallacy!) Mom’s heart might be in the right place, but that doesn’t mean she really knows what’s best for you. And it certainly doesn’t mean she, or anyone else, has a right to hold you to a life you don’t want. Especially if we DO have more options BECAUSE of our parents. We can honor our parents’ sacrifices by seizing those opportunities, right?

If you’re thinking about quitting the legal profession, then you need to think carefully about who will support you in your career change and who won’t. Seek support from those who are cheering you on, and limit what you share with the naysayers. And check out these “Tips for Dealing with Unsupportive Family Members,” an added, free bonus to this Guide that contains the same coaching techniques that my clients have used to pivot out of their legal jobs.

6. Not knowing what to do next

A lost lawyer holds a map, standing in an empty landscape with transcendent clouds in the background.

This is the crux of it, really: even if you’ve overcome the psychological, financial, and social barriers to starting a new career beyond the law, you may be at a loss as to what to do now. But the thing is, lawyers face uncertainty all the time in the work they already do each day, whether it’s a ruling that’s hard to predict or a boss or client who’s hard to please.

You don’t need to know exactly where your next steps will take you to know you need to take them. If you’re unsure of where to start, try listing what activities you enjoy each day, and which you’d rather do without. Set aside dedicated time for the activities that get you excited. And then think about—and better yet, ask people who do these things for a living—how you can turn your nascent or underexplored passions into a new career.

Plunging into the unknown can of course be scary, especially if you’re used to the stability and predictability of a law firm. But who knows what’s waiting for you after the plunge? When I first left the law for a Marketing career, I had no idea that I would eventually move to Taiwan, start a travel blog, and open my own career coaching business for lawyers and others. But everything worked out! And I tell my clients this all the time: Action leads to Clarity. Not the other way around. So what are you waiting for?

Final Thoughts about Quitting the Law

When I first contemplated leaving the law for another career, I didn’t know what to do, or who I even was anymore. But 10+ years out from my first post-law firm job, I couldn’t be happier that I took a chance on making that change; I’ve never once looked back.

Don’t let broken thinking patterns (the sunk cost fallacy, the identity crisis), poorly founded financial worries (student loans, the golden handcuffs), or social pressures (the opinions of others) stop you from finding the career that’s right for you.

Above all, don’t give yourself the excuse of not knowing what to do next—find out what you need to do next, and just do it! You’re smart, you can figure it out. You’re a lawyer, after all. For now, at least, that much is true. ;)

Need more support? Let’s connect over a call here.

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