The One Decision Unhappy Lawyers Must Make Before Changing Careers [TFLP291]

Most people who are thinking about leaving the law spend a long time in a familiar place. They know their job feels awful, they say it to themselves and to other people, and they imagine how much better things could be somewhere else. But imagining you’d like to leave is not the same thing as deciding that you want to. That shift sounds simple, but it’s tied up in identity, prestige, sunk costs, and everything you’ve been taught about what it means to be successful. It’s the first real hurdle for a lot of lawyers, and one that’s easy to avoid.

The Difference Between Wishing and Deciding

There’s a real difference between “I wish I could leave” and “I want to leave.” People often avoid the second statement because making it brings up fears about what it could mean. It’s not unusual for lawyers to keep their heads down and push through, especially if they’re the kind of person who has always taken pride in being responsible and getting the work done. But avoiding the question doesn’t make the dissatisfaction go away. It just keeps you stuck in the same place, hoping something external will make the decision for you.

A pattern shows up in a lot of the stories unhappy lawyers share. They don’t face the question until something in their life forces them to. A new baby. A second baby. A health scare. A major move. A divorce. A loss. These moments interrupt the usual routine and make it impossible to ignore what the work is costing them and what they are giving up to stay. It makes people look squarely at their values and whether their job lines up with what matters most to them.

When Being Good at Your Job Isn’t Enough

Values are one of the first things Sarah works through with lawyers, both in the Collab and in her one-on-one work. You can be good at the tasks of being a lawyer and still feel completely wrong in the job. That’s usually about values, not competence. If the job asks you to act in ways that conflict with what you care about, it won’t feel right, no matter how much positive feedback you get. This is why many lawyers feel like the work doesn’t fit even though, on paper, everything looks fine.

The important thing is that you don’t have to wait for something dramatic to push you into clarity. You can ask yourself the questions now. What am I giving up in order to stay? Are the things that matter to me present in the life I’m building, or am I setting them aside? Is this work compatible with what I want long-term?

These questions can be uncomfortable, and it’s normal to be afraid of the answers. But being honest with yourself is the only way to stop circling the same thoughts and start making choices rooted in what matters to you.If you’re sorting through these questions and trying to figure out what leaving the law might look like, Sarah’s free guide, First Steps to Leaving the Law, can help you take the next step.

Hi, and welcome to The Former Lawyer Podcast. I'm your host, Sarah Cottrell. I practiced law for 10 years and now I help unhappy lawyers ditch their soul-sucking jobs. On this show, I share advice and strategies for aspiring former lawyers, and interviews with former lawyers who have left the law behind to find careers and lives that they love.

So today we're going to talk about literally one of the most important things that you need to do if you are someone who's thinking about leaving the law to do something else. This is going to sound incredibly simple, and you're probably going to be like, “What are you saying, Sarah?” So I'm just going to say it, and then we'll go from there. Here's the thing. You actually have to decide whether you want to leave.

It is very easy to be like, “This job sucks,” and to talk a lot to others and to yourself about how much it sucks. But there is a difference between saying, “This sucks and I wish I could leave,” and saying to yourself, “This sucks and I want to leave. I actually want to leave.” I don't want to minimize it because it's actually a fairly large mental hurdle. Part of that is because it is attached to so many other things that people deal with, like sunk costs, identity, prestige, other people's opinions, and all of these things that come into play.

One of the things that I think is really interesting—and if you've listened to the podcast for a while, I'm sure you've noticed this—is that in a lot of people's stories, the thing that made them ultimately decide to do something else was something that was kind of a crisis. In some cases, an actual crisis, often a big life event. Either when someone has a kid, or when they have a second kid because they were juggling with the first, and then the second came along, and it was like, "This is not sustainable." Sometimes it's a health scare for the person or for a very close loved one. Sometimes it's a big move or another big life event like a divorce or a marriage. Or sometimes it is a death in the family or someone close to them.

If you listen to the stories that people share, there's often something that happens that makes people examine what their values are and whether the job that they're doing actually is consistent with those values. Now, you know if you've listened to the podcast, you know that I think values are incredibly important when you're thinking about what it is that you want to do career-wise. In fact, I think they're so important that they're basically the first thing that I have people work on, both in the Collab and when I'm working with lawyers one-on-one, for lots of different reasons.

One of the reasons is that you can have a perfectly matched job in terms of your skill set and your personality, but if it violates any of your important values, it's not going to be a match. For a lot of people, part of why being a lawyer is such a bad match for them is not that they're not good at the things. For many of you listening, you're like, “I am good at these things. I get lots of good feedback. I’m told I’m doing a good job,” yet it just doesn’t feel like a fit. The reason it doesn’t feel like a fit is, generally speaking, because you have a values mismatch.

To return to the point, the point was that you often will hear in these stories that people came to a point of crisis where they were forced by life to consider whether what they were doing was consistent with their values and whether it was something they wanted to continue doing. To be clear, I’m not like, “And that’s terrible, what a bad way to do it.” No, not at all.

But one of the things that I've observed is that, especially if you're a highly responsible person who's just like, “I just need to keep my head down and get this work done,” which describes most of the people who I work with, you probably are not spending a lot of time thinking about, “Is this truly compatible with my ultimate values and priorities? And what am I willing to give up in order to find something that is more compatible?”

The benefit of experiencing some life crisis and then asking yourself these questions is that often it's within the context of the crisis that you're really honest with yourself about what you're giving up in continuing to do this, or what it's costing you. I was thinking about this, and I was thinking about you who listen to the podcast, and I was thinking, what lesson is there in that? To me, the lesson for you—the thing that you can take away—is: don't wait for a crisis to push you to consider these questions.

I mean, you can, right? You can. But you do have the ability to think about those things apart from being forced to do it. If you're someone who's thinking about leaving the law and doing something else, then having that really frank talk with yourself, making a very frank assessment of, “What am I giving up? What values am I not honoring in order to continue doing this? And does that feel like something I want to continue to do?”—those are questions that you can ask yourself even apart from being forced to consider those questions.

I think that sometimes it's hard to think about those questions outside of basically being forced to by life because you are afraid of the answers. That is normal. This is not me being like, “I can’t believe you’re afraid of the answers.” No, that is normal. Something that might require you to make a big change, something that might cost you, something that might impact the way people see you—that’s a big deal. So it’s reasonable that you might try to avoid thinking about those questions because of that.

But until you are able to be honest with yourself about whether you want to leave and why, and what it is costing you to stay—and especially what it is costing you in things that might not seem as immediate, I'm not talking about money, I'm talking about like values and priorities and things that are of ultimate worth to you—being honest with yourself about those things can be very hard to do when you’re not being forced to do so. But being honest with yourself about that and about whether you want to leave is one of the most core things that you need to do to truly set yourself up for making a move, as opposed to just being stuck in this endless cycle of, “This sucks, but I feel trapped,” etc.

Whatever you need to do to be able to be honest with yourself about, “Do I actually want to leave? Is this compatible with my values? Are these the priorities that I want to know that I have lived my life according to? And if not, what are the values and priorities that are important to me? And how do I more closely match those with my work life/the structure of my life in general?”—asking those questions and answering them for yourself with honesty is one of the most foundational things that you can do in this process when you are thinking about doing something else.

Because it allows you to really know, “Yeah, I want to stay,” or, “Yeah, I want to go. And if I want to go, the reasons for it are these reasons, and they’re very compelling because they’re core to who I am as a person and very meaningful.” People's values are the things that are most important to them. It's time to be honest with yourself—ideally, not having to experience a crisis in order to do so—and letting yourself see the reality can be a very powerful catalyst for change in this area. Thanks so much for listening. I'll talk to you next week.

Thanks so much for listening. I absolutely love getting to share this podcast with you. If you haven't yet, I invite you to download my free guide: First Steps to Leaving the Law at formerlawyer.com/first. Until next time, have a great week.