Know It’s the Right Time to Leave the Law with Two Questions [TFLP231]

In today’s podcast, Sarah discusses how to know it’s the right time to leave the law. Many people listening are grappling with this question, and often, when they ask it, they are looking for an external answer. There is no external answer. You are the only person that can decide when the time is right.

With summer approaching, Sarah was reminded of the normalcy of a school calendar. You always knew what was coming next, and there was structure. You would finish a semester and get a break before diving back in. Once Sarah started practicing law, it felt unnatural because she had the internal sense that there should be a break. Even when there was a professor or class she didn’t love, she knew there was an end date.

Once you start working in the real world, no structure is set up to push you to move on at any specific time. This can be surprising for people, and you don’t realize that you’ve come to rely on it as a natural push to move on. 

When people ask if it’s the right time, they look for a sign similar to that natural pause in a school calendar. The reality is that you need to ask yourself if you want to do something else and if you have the capacity to start that process right now. Both of these questions need to be answered with a yes. 

There are things you can control, and there are things out of your control. You might be waiting until you can guarantee a specific outcome. But you only know if you want to make a move and if you have the capacity to start thinking about that process. Nothing from the outside will tell you if this is the right time. 

Is it your right time to leave the law?

If you are ready, there are things you can do right now to prepare for making a move when you are ready, look at The First Steps to Leaving the Law to get started. And sign up for the Collab to get started with a community alongside you.

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 how do you know when the time is right to think about making a move out of the law into something else? The reality is that a lot of times when people ask this question, they are looking for some external marker, some external answer. There is a sense that there is a right answer of, “Is this the right time?”

Honestly, the most important thing that I think I can tell you if you're someone who's thinking about “Is now the time to start thinking about this?” is that there is no external answer. There's nothing outside of you that will tell you when the time is right.

I'm thinking about as we get towards summer, one of the things for me that was such a realization, especially as someone who went straight through from undergrad to law school, once I started practicing law, and I wasn't particularly happy, I still had this internal sense of expecting there to be something outside of me that would tell me, “Okay, now is the time to think about doing something else,” because I had, for so long, operated on a school schedule where it was like you had a semester and then you had a break, and then you had another semester and then you had a summer break.

Even if I was working and doing other things during the breaks, there was always going to be something outside of me that ultimately changed things up. If I was in a class that I didn't enjoy, had a professor who I didn't love, or whatever, it was like, “Okay, well, that's only going to last until X time. Then I will be doing something else,” by definition, the nature of the academic calendar.

Well, the thing is, once you start working as an adult, there is no external structure or system that is going to tell you, or not even tell you, just automatically move you on to something else.

That is something that I think, especially for people who have been very into school as many lawyers were, can be surprising. You don't really realize that you've come to rely on that as a natural shaker-upper. That's not a real word obviously, but you no longer have that external structure, that mechanism to shake things up, move things around without you having to generate it yourself.

So for you, as you're thinking about “Is now the time?” one of the things that I've noticed is that for many of us when we're asking that question, we're looking for, expecting, or wanting to see that something that's telling us, “Oh, now is the time to move on to something different,” in the same way that “It's a new semester so now I have new classes,” but the reality is that for you, the real question is one, do you want to do something else? Two, do you have the capacity right now to start that process?

Those are really the only two questions and both of those need to be true, you need to want to do something else and you also need to have the capacity to at least start the process. Sometimes you might start trying to figure something out and then put it to the side for various life reasons, work reasons, or whatever, pick it back up. But ultimately, you, you are the one who can tell you whether the time is right.

Even the idea that there is a "right time" I think can be something that really holds lawyers back from even starting to explore what their options might be because there's a sense of like, “I need to feel like it is the right time for me to do this.”

A couple of weeks ago, we talked about the struggles with looking at the economy and saying, “Oh, is now the time to make a move if the economy is not doing well, or if there are a lot of layoffs in my industry, etc?”

This is a similar or related idea or question. The idea that there is a right time to start thinking about what you want to do next or to start the process, moving the process forward is inherently bound up with this idea that you can control how the process goes, what the ultimate outcome is.

The reality is in this situation, there are things that you can control. They're the things that you do. But there are also things that you can't control. That includes the outcome and what the outcome is and how quickly the outcome comes about. Waiting to feel like it's the right time is partially about wanting to feel like you can guarantee a certain outcome.

What I'm saying is basically there is no "right time." There really is only do you want to make a move and do you have the capacity right now to start thinking about that process?

Because this is the other thing, and I know I mentioned this in the episode talking about the economics or thinking about the economic climate, you, in most cases, are not going to be walking out the door the day you decide to start figuring things out.

The question of timing is much more about “When should I literally walk out the door?” not “When should I start figuring things out?” I know I said this before, but basically, if you think you want to leave, the sooner you can start, the better because the more time you have and the less chance you have of getting into a situation where you're like, “No, I really want to walk out the door now because now is actually ‘the time,’ whatever that is but I don't know what I want to do,” or “I know what I want to do but I'm not ready to position myself for it or whatever.”

Nothing from outside of you will tell you that the time is right. You just need to decide that you want to do it and you want to start now. As we roll into the summer, the summer break, the summer break that you don't have as an adult with a job, and if you're anything like me, you might have sometimes a summer where you're like, “Oh for the days when there was a semester end and then there was a summer break.”

If that happens, let it remind you that there are things that you can be doing now to set yourself up for being able to make a move when you decide it's time to make a move. All you have to do is decide that you want to start figuring it out and start.

If you need help with that, of course, there are several ways that you can work with me. One is in the Collab, which is a self-paced program and then I have a couple of different ways you can work with me one-on-one.

One is coming into the Collab and then also working together one-on-one or working together one-on-one for 6 months with 12 sessions to figure out what it is that you want to do that is not practicing law.

If you're interested in any of those things, you can always go to the website,, and there's more information there under the Work With Me tab. Thanks for joining me. I'll talk to you next week.

Are you sick of just thinking about it and ready to take action towards leaving the law? Join us in the Former Lawyer Collab. The Collab is my entry-level program for lawyers who are wanting to make a change and leave the law for another career. You can join us at Until next time, have a great week.