The Mistake Lawyers Make When They Want to Leave the Law [TFLP287]

For years, the idea of leaving the law can sit quietly in the back of your mind. You tell yourself you’ll figure it out eventually, that one day you’ll know it’s time. But months turn into years, and the only thing that changes is how tired you feel saying, “I don’t want to do this forever.” The biggest mistake most lawyers make when they want to leave is assuming it will just happen on its own.

Why Waiting Feels Easier

Lawyers are trained to follow a path with clear markers: LSAT, law school, the bar, the first job. Each step tells you what comes next. That structure creates a sense of momentum that disappears once you’re actually practicing. Suddenly, there’s no next milestone waiting to signal that it’s time for something new. So you keep waiting, half-hoping the right opportunity or some external event will appear and make the decision for you.

That waiting can last decades. Sarah Cottrell sees it constantly with the lawyers she works with—people who knew within their first year of practice that this wasn’t the right fit but stayed because they expected clarity to arrive on its own. They scroll job boards late at night, looking for something that “feels right,” but nothing ever quite does. The problem isn’t a lack of options. It’s that they’re still waiting for permission to make a change.

Clarity Comes from Action

Recognizing you don’t want to be a lawyer forever doesn’t mean you need to quit tomorrow. You can decide to stay for now and still move toward something different. The key is doing it intentionally. Taking even small steps, such as reflecting on what parts of your work energize you, exploring other careers, or talking with a therapist, can start to shift how you think about what’s possible. Clarity follows action, not the other way around.

Stop Waiting for the “Right Time”

If you’ve been telling yourself that things will somehow change, consider this your reminder that they won’t—unless you do something different. Waiting for the “right time” usually means waiting forever. The truth is, there’s never a perfect moment to figure out what’s next. At some point, you decide to stop waiting and start paying attention to what you actually want.

If that’s where you are, download First Steps to Leaving the Law. It’s a short guide Sarah created to help you start sorting through your thoughts and identifying what might come next.

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.

Today, I want to talk about one of the big mistakes that I see lawyers making who want to leave the law. I'm very familiar with this particular mistake because it's definitely one that I made during my time as a lawyer. For those of you who've been listening for a while, you know I practiced law for 10 years. I was at a law firm, I was at a legal publishing company, and then I was a staff attorney at a state appellate court.

I knew that I wanted to leave law pretty early on. I knew within less than two years that there was a pretty good chance I would eventually want to leave permanently. I've talked before about how working at the Court of Appeals was like, if there was going to be a lawyer job for me that really was going to be the long-term, it was going to be that one. Ultimately, I just knew I didn't want to do it forever. And that's how I knew I didn’t want to be a lawyer. But one of the things that I see with clients and that I experienced myself is that it's one thing to have this idea that you want to leave, and it's another thing to actually take steps towards doing it.

Often, when people join the Collab, which is my program for lawyers who want to do something else and need help figuring it out, they fill out the intake survey. One of the questions asks about how they found Former Lawyer, etc. It's very common in those that people share something like, "I've been thinking about this for a long time." For some people, it's been a year or two, but for a lot of people, we're talking 5, 10, 15, 20 years plus. Then people are in the Collab, and we’ll have a group call, we'll talk about how things are going, and one of the things that I will often hear from people is that they wish they had started sooner.

That is especially true because even for people who aren’t making a move imminently, being in that position of actually thinking about what else it is that they might do and taking steps towards it really makes a difference in how they feel about their day-to-day. This relates to the mistake that I often see lawyers making, which is that it is very easy—and again, there’s zero judgment here because been there, done that—it is very easy to want to leave and have this sense that somehow it’s just going to happen.

I think a big part of that is what we talk about on the podcast often, about the nature of being a lawyer and having been someone who went through the process of becoming a lawyer means that for a really long time, you were on a very set path. You were in grade and secondary school, then you were in college, and then you were in law school. If you went to a firm, you were an associate—a first year, or second year, etc. Even if you didn’t go to a firm, there still was that progression: take the LSAT, go to law school, pass the bar, practice law.

There is this sense of almost inevitability that I think we can experience as lawyers because so much on the front end of the career is, “And then this happens, and then this happens, and then this happens.” It’s not to say that happens without us doing anything—obviously, we have to try—but the path is very clear. In a sense, the things that we are aiming towards, whether it's going to law school, there’s a very clear point at which it’s like, “And now you will figure out your job for after law school,” or, “And now you will take the LSAT to prepare to apply to law school.” There’s something outside of you that tells you, “Okay, now is the time.”

What often happens for lawyers when they’re thinking about leaving the law or they aren’t happy with their jobs and leaving the law is something that they think about, is that we inadvertently think that there’s going to be something external to us, like the things I’ve just talked about, that’s going to tell you, “Oh, now is the time to figure this out.” Or somehow, the fact that you want to leave will result in you finding something that is the right fit and leaving. That’s part of what fuels the doom scrolling of the LinkedIn job boards. It fuels that sense of, “If I’m just scrolling randomly, I might find the thing that I’m supposed to go to,” and then you’ll go, and it’ll be another step on the obvious path.

The reality is that if you assume it will just happen, it’s not going to happen. I work with a lot of people who are 15, 20, 25 years into practice, and they will tell me, “I literally knew I didn’t want to do this on the first day of law school,” or “the first year of practice,” or “by the end of year five.” But there are so many things about life that take up time. This is not me saying don’t make an intentional choice to stay in the law for some period for various reasons.

Because as I was talking about my story at the beginning of the episode, just because you’re like, “I don’t want to do this forever,” does not mean you need to leave tomorrow or this year or next year. You could choose to stay for years and make various tweaks to make that work for you. But what I have seen is that people can really detest what they’re doing—you can really dislike, you can hate what you’re doing and want to leave—but if you assume it will just happen, there is a very good chance that it isn’t going to happen, and you will find yourself 15, 20, 25 years down the line still practicing law.

Again, that is not judgment. That is not me saying you’re bad. But I think it’s that our profession conditions us to think that that won’t happen because of the way there are all of these external checkpoints that have moved us along that don’t really exist once you’re actually practicing. Because you’ve been going down this path, the legal practice path, for a really long time, the reality is that you do actually have to take some intentional steps to find a different path.

That can be starting really small. Again, as always, I’m not saying, “And that means you should quit tomorrow.” But I do think it’s helpful to ask yourself, “What active steps am I taking towards a different career reality for myself? Or am I just assuming that somehow things will change?” Maybe you’re assuming things will change because you’re in a really ridiculous period at work, and you do not have the energy to think about anything else other than, “Maybe hopefully one day this will be different.” And that’s fine.

I'm not like, “How dare you?” I think it’s very clear from the podcast that I am very aware of things like burnout, etc. But if you want to make a change, then you do need to take some intentional steps, and they can be as small as you want. It could just be going to therapy. It could just be thinking about what skills you want to exercise that you’re not getting to exercise as a lawyer, or lots of other things.

But if you’re someone who’s interested in leaving the law, definitely give some thought to, “Am I just assuming this is going to happen, or am I actually taking action?” The action is where the clarity happens, and that is how you end up getting out of law into something else that works better for you. Thanks so much for listening. I hope you have a great 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.