Is the Grass Greener When You Leave the Law? (What Former Lawyers Say) [TFLP280]

The question comes up constantly – in podcast interviews, on Collab group calls, and in emails from listeners. “What if the grass isn’t greener on the other side?”

It’s tied to this idea that maybe being miserable at work is just what it means to be an adult with a job. Maybe every workplace is toxic. Maybe no one really likes what they do. You’ll even hear people outside the law say things like “Well, no one likes their job.”

There’s something almost protective about believing this. If you don’t believe it will be better elsewhere, it’s easier to keep doing the thing you’re doing, even if the thing that you’re doing is painful and not great for your mental and physical and emotional well-being.

But after six years of interviewing former lawyers, I can tell you the grass really is greener.

The Evidence From Hundreds Of Conversations

I’ve had several conversations on the podcast with people who are in non-practicing roles and who said repeatedly, “It is so much better.”

Dan, a member of the Collab, ended up moving to a different type of legal work. He talked quite a bit about his experience of thinking it was going to be the same no matter where he went, and in fact, it wasn’t. When I talked with Tiffany Obeng – she’s been in non-practicing roles, she’s been in practicing roles – I asked her if it’s actually better. She was like, “Of course, yes, it’s better in so many ways.”

That has happened in many interviews on the podcast. Yet when you’re still working as a lawyer, it’s often hard to believe that, because I think there are two things. One, a lot of us don’t really trust ourselves very much, especially when we’ve ended up in a role that isn’t a good fit for us. We start to really question our ability to actually make an assessment about what is a good choice.

Related to that, there’s this fear – “What if I go do something else and it is worse? Then I’m just in an even worse position.”

Listen, I am not someone who’s going to be unrealistic or not live in reality. That’s not my personality. That’s just not who I am. So is there some possibility that you might end up in something that is an even worse fit for you than your current job? Yes, of course, there’s always a possibility.

That said, it’s highly unlikely for lots of different reasons. One of the main reasons is that for most people who ended up as a lawyer, they have more information now than they did when they were making the original decision. Back when they were making the original decision, they weren’t considering all the things that they are able to take into account now.

Your experience working in a job that isn’t a great fit and going through a process to figure out a job that is a good fit actually increases significantly the likelihood that the move is going to be into something that is a better fit for you, even if it’s not the thing that you do forever.

What Six Years Of Data Shows

Even if you were to make a move and it wasn’t the right one, ultimately the skills that you develop in making that move allow you to make the next move and the next move and the next move to get closer and closer to the thing that really is the right fit for you.

Statistically, observably, the podcast has been going for six years now. If you’re someone who feels about the legal profession the way that the former lawyers who’ve been on the podcast feel and felt about the profession, you have also heard, or can hear from if you’ve not listened yet, too many people sharing that, yes, it really, really is better.

The grass really is greener on the other side in almost all circumstances. It can be hard to remember, especially if you’re in the real grind of it all, it can feel like this is the only way that a job could be, and it’s just not true.

The great thing is, even if you were to make a move and it wasn’t the right one, ultimately the skills that you develop in making that move allow you to make the next move and the next move and the next move to get closer and closer to the thing that really is the right fit for you.

If you need help going through that process, that is why the Collab exists. It’s a self-paced group program for lawyers who want to figure out what it is that they want to do that isn’t practicing law. There’s a framework you follow, there are panel discussions with former lawyers, and there’s a monthly group call so you can check in and get support.

Ready to start believing the grass can be greener for you too? Download the free guide First Steps to Leaving the Law and begin exploring what’s possible.

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 I want to talk about something that has come up in many of the interviews in the podcast. It comes up with my clients all the time. It comes up on group calls for the Collab. It's in emails that I get from people. The question or the idea that tends to often plague people when they're thinking about leaving the law to do something else is, "But what if the grass isn't greener on the other side?"

This is related to something we've talked about before, which is this idea of, "Well, what if this is just what it is to be an adult with a job? I'm miserable doing this work. This organization seems super toxic. But no one really likes their job/it's a job." You often will even hear from people in your life outside of the law who say things like, "Well, no one likes their job," these sorts of things.

So people have this sense that surely it must be better elsewhere, but at the same time, they're afraid to believe that it actually is better elsewhere. Does that make sense? And it's interesting because I think that part of it is almost a self-protection thing. If you don't believe it will be better elsewhere, it's easier to keep doing the thing you're doing, even if the thing that you're doing is painful and not great for your mental and physical and emotional well-being.

I think there is a degree to which it can be helpful in a certain way to believe this if you're in a position where you aren't yet prepared to leave or think about leaving. The problem is that beyond that point, it is a very unhelpful thing to think. Also, the more important thing is that it's just not accurate. By that, I mean we've had several conversations on the podcast with people who are in non-practicing roles and who said repeatedly, "It is so much better."

We even had someone, Dan, who's a member of the Collab, who ended up moving to a different type of legal work. He also talked quite a bit about his experience of thinking it was going to be the same no matter where he went, and in fact, it wasn't. I know that it comes up on the podcast over and over and over. When I was talking with Tiffany Obeng, I asked her—she's been in non-practicing roles, she's been in practicing roles—I asked her, "Do you actually think it's better?" And she was like, "Of course, yes, it's better in so many ways."

That has happened in many interviews on the podcast. Yet for us as lawyers, when we're still working as a lawyer, it's often hard to believe that, because I think there are two things. One, a lot of us don't really trust ourselves very much, especially when we've ended up in a role that isn't a good fit for us. We start to really question our ability to actually make an assessment about what is a good choice.

Related to that, I think there is this fear of, "What if I go do something else and it is worse? Then I'm just in an even worse position." Listen, I am not someone who's going to be unrealistic or not live in reality. That's not my personality. That's just not who I am. So is there some possibility that you might end up in something that is an even worse fit for you than your current job? Yes, of course, there's always a possibility.

That said, it's highly, highly unlikely for lots of different reasons. One of the main reasons is that for most people who ended up as a lawyer, they have more information now than they did when they were making the original decision. Back when they were making the original decision, they weren't taking into account all of the things that they are able to take into account now.

Your experience working in a job that isn't a great fit and going through a process to figure out a job that is a good fit actually increases significantly the likelihood that the move is going to be into something that is a better fit for you, even if it's not the thing that you do forever. I just wanted to have an episode where I reiterate that the grass really is greener on the other side.

Statistically, observably, the podcast has been going for six years now. If you're someone who feels about the legal profession the way that the former lawyers who've been on the podcast feel and felt about the profession, you have also heard, or can hear from if you've not listened yet, too many people sharing that, yes, it really, really is better. I just wanted to remind you of that today because it can be hard to remember, especially if you're in the real grind of it all, it can feel like this is the only way that a job could be, and it's just not true.

The grass really is greener on the other side in almost all circumstances. The great thing is, even if you were to make a move and it wasn't the right one, ultimately the skills that you develop in making that move allow you to make the next move and the next move and the next move to get closer and closer to the thing that really is the right fit for you.

If you need help going through that process, that is why the Collab exists. The Collab, as you know, I'm sure, if you listen to the podcast for any length of time, is my self-paced group program for lawyers who want to figure out what it is that they want to do that isn't practicing law. You can join anytime. Just go to formerlawyer.com/collab.

There's a framework you follow. There are a bunch of panels recorded with former lawyers who've gone on to do other things. There's a monthly group call so you can check in and get support, and your questions answered, and all of those things, to get into a position where you can move to something where the grass is, in fact, greener. Again, that's formerlawyer.com/collab.

I would love to see you in there. It has been a really exciting time in the Collab. There are a lot of people making a lot of moves. So if you need support, join us. Thank you 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.