How to Work Through Conflicting Emotions as You Transition Out of the Law [TFLP162]

In this episode, Sarah talks about lawyers and former lawyers feeling conflicted about transitioning out of law for fear of missing out or underachieving in their new field. These lawyers think that those who are practicing are more “successful.”

Here, you will learn how to overcome the fear of failing and how joining the Former Lawyer Collaborative can help you to ditch regret and fear. Let’s get into it!

Do you feel conflicted about leaving the law?

It is not impossible that when you are traveling home for holidays or seeing people that you don’t see often, you find yourself struggling with the thought that maybe leaving the law isn’t the right choice. 

That confusion worsens when you meet up with friends or acquaintances who are still practicing and look “successful” in their careers based on the metrics discussed on the podcast. Many of these lawyers have great-paying jobs and enjoy the practice’s prestige.

Most clients who join the collaborative feel conflicted about transitioning out of law when they talk to friends, especially law school classmates or former coworkers at law firms. On the one hand, they are happy that they left. On the other hand, they feel like they are underachieving compared to their friends who can afford vacations and expensive things. 

They don’t necessarily feel jealous. Sometimes, it’s just the fact that they are not getting paid as much in their new career path and cannot afford the things they want. For others, it is a more critical feeling where they feel left behind or think they have done something wrong to not get the same results as their former colleagues. 

Just know that whatever you feel right now is an expected part of making a major decision, like transitioning out of the law. 

Why you are worried about your achievements

Usually, transitioning lawyers feel conflicted about transitioning out of law because of a sense of grief. 

This grief is around the idea of who you thought you were going to be and that younger version of yourself who thought that achieving that particular archetype was going to be the point where you had arrived, and that’s no longer the case for you.

Even if you feel good and your values align with this different path, you may still feel guilty, especially when you encounter other lawyers who have not taken one of your paths.

Another way that former lawyers grieve their former career paths is through the longing to remain part of the spaces they created. They go from feeling like a part of the group in their former workplace to wondering if there is space for them in their new endeavor. They feel like they’ve been displaced from familiar territory and the lifestyle they were used to.

Both expressions of grief are valid, and you should not feel guilty for feeling that way.

What to do when you feel conflicted about transitioning out of law

The first thing for everyone to do is to remember that there is probably grief and see if that is coming up. 

If you are torn between settling into the familiar at your law firm or following a new course, it is important to recognize that a change is happening. You should also ask questions about your former workplace, like “Do these people seem to have space for my now different lived experience, and I just need to adjust to the fact that I am fitting a different shape in this group?” Or is this a group of people who can’t necessarily hold that space for someone who has a very different lived experience?”

In all of these things, it is important to honor your feelings and recognize that just because you’re feeling grief is not a reason to think that you’ve done anything wrong or a sign that you’ve made a wrong choice. Be sure to explore your feelings and not pretend they don’t exist. 

Remember that feeling this grief, awkwardness, lack of confidence, or surety around people in these various contexts doesn’t necessarily mean, “Oh, you made some horrible choice, or something is wrong.” It’s sometimes just that feeling of things being different.

You can find more details about some ways to work through grieving your legal career in episode 156 of this podcast. Of course, therapy is a great option to help you overcome the grief of embarking on a new career path.

Embrace your new normal

Recognizing that change isn’t bad and allowing yourself to feel all the emotions that come with leaving the law is the most important thing to do when you’re in situations where you’re encountering a friend or former colleague who appears more “successful” than you.

However, it is certainly easier said than done.

That is why joining the Former Lawyer Collaborative offers you the kind of support and handholding that you need to help you process the emotions that come with transition. You will find a community of lawyers that have experienced this phase and are willing to connect with you.  

If you prefer a one-on-one approach, Sarah also works with lawyers who want a personalized approach to getting the support and guidance necessary to advance in their new careers.

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.

Hello everyone. Today I want to talk about a topic that is going to be really relevant for a lot of you as we roll into the next couple of months here. This episode is releasing just a couple of weeks before the Thanksgiving holiday in the US.

As we roll into this part of the year with lots of holidays and lots of people traveling to their homes, or seeing people who they might not see the rest of the year, one of the things that often comes up in these situations when I'm talking with people is that they find themselves struggling, either they've left the law, and they're happy, they're happy that they did, or they're thinking about it or they're in the process of it and they know that it's the right choice for them, but they encounter people who are still in, like friends or acquaintances who are still in the law and are more “successful” than them and by that, I mean more successful by the metrics that we often talk about on the podcast in terms of the legal profession and the ways that the legal profession values prestige and jobs that pay a lot of money.

What I have seen my clients and friends encounter, sometimes when they're in these situations where they are interacting with, in particular, classmates from law school, or maybe there's some holiday thing at a former firm that they are invited to as an alum of the firm, so they go back, there can be somewhat conflicting feelings.

Because on the one hand, people are really happy that they've left, but on the other hand, they look at these friends or these acquaintances, these former colleagues who have more of the trappings of what the legal profession sees as success, whether that's super fancy car, their kids are in a really fancy school, particular watches or bags, or the fact that they are going on really lovely and elaborate vacations, all kinds of different things that in and of themselves, the friends or clients who I'm thinking of aren't necessarily like, “Oh, I'm jealous,” although some of that might come up, there might be like, “Oh, I left this job that paid x,” and in some cases people leave for something that doesn't pay as much so they aren't necessarily as financially able to do the same number of things.

There can be that feeling of working through the internal conflict of feeling some of that jealousy, and then at the same time also knowing that you feel the trade offs are worth it. That conflict can make former lawyers feel like, “Well, I'm feeling this, does that mean something?” I'm happy where I am having left but I'm going to say like a classic lawyer, an emotional tailspin. If you don't resonate with it, that's totally fine. I'll just take that on for myself.

But apart from the jealousy piece, which can come up for some people, there's often a more common thing that happens, where people look at their former colleagues or law school friends who are still at a big firm making the big bucks and they feel like “There's something wrong with me that I don't have what that person has. I have somehow been left behind or opted out in some way that was wrong,” that can feel really strange and it can feel confusing, because a lot of times, we as lawyers and former lawyers, who often have developed certain types of personalities and ways of being in the world can see that discomfort, that discomfort that we feel as like, “Oh, maybe that's trying to tell me something. Maybe I've done something wrong.”

I mean, I think that it's probably not unfair to say that for most lawyers, it is very easy to push them into, “Maybe I've done something wrong. Maybe I'm not doing the right thing,” question spiral. Again, if that's not you, totally cool. I will just take that off myself or take that on as a descriptor of myself.

If this is you, if you're someone who has experienced, you go to a firm alum event, and you're like, “Oh, my goodness, I'm so glad not to be here anymore,” but at the same time, you are talking with someone and they're talking about various things that they're doing, whether it's professionally, certain achievements professionally that are happening or facilitated because they are still at a big firm, or whether it's something like they're sending their kids to some particular school, and it makes you feel some way, the first thing that I would say is go back and listen to the episode that I released a bit ago about grief and grieving your legal career and some of your ideas of what things were going to be like.

Because honestly, I think the biggest thing that is coming up in these situations where people are like, “Wow, I felt this way about seeing this person doing the thing that I thought that I was going to do or at one time I thought I should be doing, and even though I no longer think is what I should be doing. But seeing this person doing the thing is making me feel like did I make a wrong choice?”

Often, what's coming up there, the core emotion that's coming up is actually this grief, this grief around the idea of who you thought you were going to be, who at one point you maybe thought you should be, grieving that younger version of yourself who thought that achieving that particular archetype, embodying that particular archetype was going to be the thing where you have arrived and that's no longer the case for you.

Even if that's good and feels in alignment with your values to be on this different path, there is still that grief there that is going to come up, especially when you encounter other lawyers who have taken one of your paths not taken. I think the first thing for everyone to do is to remember that there is probably grief, see if that is coming up. I talked more in detail in the grief episode about some ways to work through that or think about working through that. Of course, I will always tell you, have you considered therapy? Because that is also a great option.

Hey, it's Sarah. I want to remind you that I am now working with a very limited number of lawyers one-on-one who are trying to figure out what it is that they want to do that isn't practicing law. What we'll do when we work together one-on-one is we will meet for 12 weeks and you and I will walk through the framework that I've created to help lawyers do exactly that. On top of personalizing that and making individualized choices about which pieces of that you need to focus on, spend more time on, spend less time on, I also have the capacity to lend my brain to your situation.

When we're working together one-on-one, I'm able to look at cover letters, resumes, and other things that you may be putting together, cold outreach emails, figuring out who you might want to reach out to, figuring out, “Okay, I have all this information about who I am, values, personality, strengths, etc., from these various assessments, but how do I put that together into a picture of what it is that I actually want to be doing? How do I figure out what I actually want my life and career to look like?” all of those things.

If that sounds like something that would be helpful to you, I would love to talk with you about whether or not working with me one-on-one is the right fit for you. Go to the website, the Work With Me drop-down, there's a link to information about working with me one-on-one. You can see more details and the price as well as the button to book a free consult with me so that we can talk through whether working with me in this capacity would be the right fit for you. I onboard one new one-on-one client per month so if this is something that you're interested in, definitely schedule that call as soon as you can because I fill the spots on a first-come-first-served basis. I look forward to talking with you about whether working together one-on-one could be a good fit.

There's also another piece though that I think is really helpful and it is related to the idea of grief. For example, I'm thinking of situations where, let's say you're meeting up with friends from law school who are former colleagues, other people who you've worked with as an associate at a law firm, and you're meeting up somewhere fancy. You're talking, you're having conversation, and you're realizing like, “Wow, their lifestyle is a lot fancier than mine.”

Again, for many people, it's not that this is coming up as jealousy of like “I want their specific lifestyle,” but there is this sense of like, “Oh, am I supposed to be one of those people like this person who's having that lifestyle and the fact that I'm not because of the decisions that I've made, does that mean something?” It can bring up a lot of feelings around belonging, about like, “Well, I used to feel like I was a part of this group,” you still are, but in some cases, maybe some of the ways that you bonded with these people, especially when you're talking about former colleagues, may have been around some of the things that are facilitated by having a large law firm salary that you may or may not have in whatever role or career you've ended up moving to.

Again, there's a grief piece there, but there's also the recognition of seeing that for you in that situation, you are experiencing this sense of like, “Is there still space for me here?” I think when that happens, recognizing that, “Oh, hey, this is happening,” and like, “Is this a real question, or is this just a question that I'm creating? Do these people actually really seem to have space for my now different lived experience and I just need to adjust to the fact that I am fitting a different shape in this group? Or is this a group of people who don't necessarily have the capacity to hold that space for someone who has a very different lived experience?”

Then of course, I think, if that is what you ultimately conclude, then it takes you back to the questions of grief and being able to grieve what once was and isn't now. Also, in all of these things, I think it's so important to honor the feelings that you have, and also to recognize that just because you're feeling grief by itself is not a reason to think that you've done anything wrong, you've made a wrong choice, it's some sign.

It could be, so explore those feelings. I would not recommend just tamping them down and pretending they don't exist. That doesn't tend to go well, although that’s something that we lawyers can be very good at. But I do think it's important to remember that you feeling this grief or you feeling this awkwardness, you feeling some lack of confidence or lack of surety around people in these various contexts doesn't necessarily mean like, “Oh, you made some horrible choice or something is wrong,” it sometimes just is that feeling of things being different.

For all of us, our brains, we are creatures of habit, and we'd like things to feel the same. When something feels different, that makes us think often that there must be something wrong, something must be wrong. It may not be that anything's wrong, it may just be you adjusting to the fact that that environment doesn't feel the same, that group of friends doesn't feel exactly the same.

You're not exactly the same, things have changed and maybe most likely not in fundamental ways, maybe most likely not in like we're not really friends anymore, or something like that, it's not that that's totally impossible, but most of the time, it's just “Oh, the way in which I now connect to and fit in with this group or this person is different than it was before,” and different isn't bad, but it is different. Recognizing, seeing that, and allowing yourself to feel it, I think is the most important thing that you can do when you're in these situations where you're encountering a friend or former colleague who is more “successful” than you in these legal profession metrics of success.

It's certainly easier said than done. But having this awareness and having this compassion for yourself, curiosity about your experience is going to really help you as you move through these situations to do so in a way that honors both your experience and other’s experience, and provides a path forward through situations that can sometimes feel a little bit awkward. I appreciate you listening. I hope you have a great week and 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 Until next time, have a great week.