Transitioning Out of the Law: The Former Lawyer Story Part 1 (TFLP 100)

To celebrate the 100th episode of The Former Lawyer Podcast, I’m sharing something a little different than usual, an interview with me about how transitioning out of the law and began Former Lawyer. 

I first shared my story on the very first episode of the podcast two years ago, but I didn’t go into a ton of detail around how I transitioned out of the law and that was a long time ago, so I wanted to share a little bit more of my story. 

To help with this, Jessica Medina, a former Biglaw lawyer turned financial coach and accredited financial counselor, is going to interview me. This is going to be the first half of our conversation because we had so much to talk about. This is basically my story in the same format that you typically hear other people’s stories. 

I’m really excited for you to enjoy this episode, we talked about some things about transitioning out of the law that I haven’t talked about before. 

Before Transitioning Out of the Law: Law School 

The truth is that my life as a lawyer started almost by accident.  I sincerely knew almost nothing about what it was to practice as a lawyer. There weren’t any lawyers in my family, I hadn’t really grown up around lawyers. I had no idea what Biglaw was. I had no idea what starting salaries were for lawyers. 

Looking back on my 21 year old self, I now think, “Wow, those seem like questions that would have been really good to have answers to before you made this choice.” So I share that because I know that there are lots of people who had a similar experience in how they decided to go to law school, it wasn’t always the plan for most of us. 

Beginning A Legal Career 

There were signs in law school and my first job that a legal career wasn’t for me. There were classes I took because I thought I should want to take them, not because I was interested in them. I didn’t enjoy many of my courses, but thought I just hadn’t found my area yet. 

And at my first firm, I was put on a massive case, one with 40 lawyers, it was very stressful. In fact, it was the first time I’d ever pulled all-nighters, I hadn’t even had to do that in college. 

I quickly realized a few things about a legal career from this experience. One, I did not have good boundaries with work. I had always been someone who did well in school. I was a high achiever, I was valedictorian of my high school class. I had worked hard in undergrad and in law school, but I also derived a lot of my identity from being that person who is the go-to person who works hard and you can rely on, and you know that they’re going to produce good work. 

I think that’s what is so tricky for many of us as lawyers, it’s not bad to be reliable, to work hard, to produce good work – but when your identity is wrapped up in that and you’re in an environment that is so lacking in boundaries, like Biglaw is, it can very quickly become very toxic.

Two, I wasn’t able to disconnect and compartmentalize like many are able to do. Some people can roll with the punches, but for me, I felt like I was constantly walking around with this sense of foreboding and doom that work would never end and always pop up, which it did, many times on nights and weekends. 

And part of the problem was that it was rewarded to always be on and not have boundaries. I observed that people who had better boundaries than I did were perceived as not a team player, as lazy, as not reliable. It was a toxic combination of my own boundary issues and the environment itself rewarding a lack of boundaries.

The Traditional Progression Before Transitioning Out of the Law

Like many lawyers who eventually transition out of the law, I went through thoughts like, “Oh, I don’t really love what I’m doing.” but convinced myself it was maybe just litigation or the area I was in. I thought about moving to corporate, about moving within the firm, then I figured that Biglaw was the same everywhere, and that wouldn’t be enough. 

But at that point, I was not thinking about leaving the practice of law or significantly changing what I was doing, I had only been practicing for maybe 18 months at this point. It just didn’t even occur to me that all these feelings could mean something more than that I should just go to a different firm.

Instead, I started looking at smaller firms, thinking I’d be happier with more hands-on cases. I got some interviews, and I remember driving to the interview for the first one and having this moment where I realized, “I don’t want to do any of the things that I’m going to have to tell them I want to do in order to get this job.” 

I realized I had been approaching things from the mindset of, “Okay, this is the thing that I’m supposed to do. The goal of this is to get interviews, get callbacks, get on a case, whatever the goal was.” That was what I was focused on, not “do I genuinely want to be doing this?”

That realization changed my path. I began looking at Indeed just to see what other types of jobs would spark my interest. I spoke to my husband about leaving. He worked in Biglaw as well and understood the dynamics at play. 

Transitioning Out of the Law to Legal Publishing and Beyond

I ended up leaving my firm for a legal publishing company, a change that felt like I went from 90 miles per hour to 10. That was a bit too much of a change, so after a short period of time, I ended up changing jobs again, moving to a Court of Appeals. 

That role was a much better fit, both substantively in terms of the work but also, I found it to be a much better situation in terms of work-life balance. The work was interesting, it didn’t spill into my nights and weekends, it was definitely a better fit, but I still had these feelings of, “But I still don’t want to do this forever.” It was these feelings that brought me to the point of being able to finally say, “This just isn’t for me. I don’t want to be a lawyer for the rest of my life.” 

That, mixed with changes in our circumstances, I was pregnant with our second child, we were about to pay off our student loans, I decided I wasn’t going to return to the law after my maternity leave. 

Who Are You If You Aren’t A Lawyer

After making the decision that I was going to transition out of the law, I had to come to grips with my identity. Who was I if I wasn’t a lawyer? 

This is something that comes up so often with the people who I’m working with in The Collaborative, they are also asking things like “Who am I if I’m not the person who is the highest achiever? Who am I if I’m not in law? Who am I if I’m not just the gold star getter?” 

I had to really work through this questioning before officially transitioning out of the law, which you can hear more about in Part 2!


Sarah Cottrell: Hi, and welcome to The Former Lawyer Podcast. I'm your host, Sarah Cottrell. On this show, I interview former lawyers to hear their inspiring stories about how they left law behind to find careers and lives that they love. Let's get right to the show.

Hello everyone and welcome to the 100th Episode of The Former Lawyer Podcast. I am so excited that this is the 100th Episode. We decided to do something a little bit different for this episode. I first shared my story on the very, very, very first episode of the podcast two years ago when the podcast started. I didn't go into a ton of detail. Also, it was a long time ago, so I wanted to share a little bit more of my story. I wanted to do that, not on my own because that would be a very long monologue. So Jessica Medina, you may remember her, she is a former Biglaw, then SEC. She now is a financial coach or accredited financial counselor. She works with Biglaw lawyers. She was on Episodes 59 and 60 talking about being a single mom of twins, having twins in law school, then going into Biglaw. I definitely recommend you check out those episodes. But she came on the podcast and she interviewed me. This is going to be the first half of our conversation because, of course, we had so much to talk about. Essentially, you're going to be hearing my story in the same format that you typically hear other people's stories. I'm really excited for you to hear this. We talked about some things that I haven't talked about before. I am excited to get into it. Without further ado, let's get into the 100th Episode.

Jessica Medina: Hello Former Lawyer Podcast listeners, this is Jessica Medina. Yes, I am here taking over Sarah's podcast for today. Why? Because we want to hear her story. I get to ask the questions, Sarah is going to be in the hot seat, and you're going to hear her amazing story. Sarah, are you ready?

Sarah Cottrell: I'm super excited. Thank you for doing this.

Jessica Medina: All right. This is The Former Lawyer Podcast but tell us how did you end up in law school?

Sarah Cottrell: I think the thing about how I ended up in law school is that, and for anyone who's listened to the podcast for a while, both know so many of our stories sound very similar and mine really is no different. I went to undergrad, not really thinking specifically that I would be a lawyer but it had been just like something that was floating out there because I liked reading, I liked writing. The real truth of it, I was an International Studies and Leadership Studies double major. Originally, I went to undergrad in Virginia and I thought that I wanted to go to DC and do policy work or maybe work in politics. I fortunately developed enough self-awareness in college to realize that probably is not going to be the path for me.

The problem was that I really didn't have any other ideas of what I could do with the degrees that I was getting, so one thing led to another. I took some classes at the law school at my undergrad that were cross listed. I really liked them and decided, “Oh, research and writing, I like that. I should go to law school,” which again, I think some variation of that story is super common. I actually thought that I wanted to teach law, which really I think is just because I like the idea of teaching, but then I got to law school and I was like, “Oh, legal scholarship is terrible.” Like people writing about random arcane things that don't really seem to have a lot of impact in actual life or the actual practice of law, then other people who are trying to get tenure writing about those things, I realize this is a very particular characterization but that's how it felt to me. It was very much like, “Oh, this is definitely not what I want to do. Then I was in law school and it never really occurred to me to not continue. I just was like, “Oh, I'm here. I'm going to have student loans. I probably should get a job. I like research and writing. Litigation, that seems like a great plan.”

That's the story of how I ended up in law school. I know I've mentioned this in many episodes before but I sincerely knew almost nothing about what it was to practice as a lawyer. There weren't any lawyers in my family. I hadn't really grown up around lawyers. I had no idea what Biglaw was. I had no idea what starting salaries were for lawyers. Looking back on my 21 year old self, I just think, “Wow, those seem like questions that would have been really good to have answers to before you made this choice.” I share that just because I know that there are lots of people who had a similar experience in terms of deciding to go to law school.

Jessica Medina: Yeah, I think law school is a very natural default selection for people. We hear that all the time. It's not even like you majored in underwater basket weaving and weren't sure what to do. You had a real major in a real field of study and it was still a difficult decision to see, “Wow, what is the next step here? I guess it's law school.” So many people fall into that as just kind of a default. You made it through law school, now learning a little bit more, “These are all questions we would have asked now that we have our lawyer brain.” What information do we have before we make these big huge decisions? But you went into litigation, what were your first years of practice like?

Sarah Cottrell: I look back on it now. First of all, I graduated law school in 2008. That was just as the great recession was starting. When I was interviewing the previous year, there were lots of jobs available. I can remember going through OCI, I didn't even know at that point like, “Oh, I want to do litigation versus I want to do court.” I had genuinely almost no idea of what I wanted to do. I summered at a firm and did projects in a bunch of different departments. That was the point where I decided, “Oh, research and writing, litigation, that seems like a good point.” But even in law school, I think it was my third year, I took a trial advocacy class because I was like, “Well, I'm going to be a litigator, this is the class that people who want to be litigators take.”

Looking back, I realized it's very telling. It wasn't like, “Oh, I genuinely want to take this class because I want to do this.” It was like, “Well, I should want to take this class, so I'm going to do it.” I did fine in the class but I did not enjoy it at all, which granted, the experience of doing trial advocacy, and essentially, a faux trial, like a NITA style trial, is different than the experience of being a first-year litigation associate at a Biglaw firm. But even so, looking back, I think there were already indicators before I even started that like, “Is this really a match for me?” So I started at the firm. Almost immediately, I got put on this case. This was a huge massive case with 40 lawyers and a whole deal, and very stressful. It was the first time I'd ever pulled all-nighters because I have been a grandma since a young age. I didn't ever pull an all-nighter in college or law school but once I started to forget the firm, that started happening.

I pretty quickly realized a couple of things. One, I did not have good boundaries with work. I had always been someone who did well in school. I was a high achiever. I was valedictorian of my high school class. I had worked hard for sure in undergrad and in law school but I also think that I derived a lot of my identity from being that person who is the go-to person who works hard and you can rely on, and you know that they're going to produce good work. I think that what is so tricky for so many of us to become lawyers is that it's not bad to be reliable, to work hard, to produce good work. But when your identity is wrapped up in that and you're in an environment that is so lacking in boundaries, like Biglaw is, it can very quickly become very toxic. That was certainly my experience.

My first year, because I was in this big case and everyone was saying like, “Oh my goodness, this is a once in a lifetime situation. For all these various reasons, yes, this is terrible but you'll never experience anything like this again in your career. This is truly exceptional.” I can remember, we were in the location where the case was being tried. It was in Texas, which is where I was practicing at the time. I remember walking outside of the building where our offices were set up and it being super warm, I can't remember going from the air conditioning, which was super cold, walking outside, it was super warm, just standing there in the sun, sweating and thinking like, “This is horrible. Is this what it's going to be like?” Then being like, “Well, people say that this is normal and this is not how it is all the time. I just need to survive. I just need to make it through and it will get better.” I have a very distinct memory of having a moment like that. Then that case settled as many cases do when you work at a Biglaw firm after a couple weeks of trial and to be clear, I was the lowest of the lowest of the low lawyers, obviously, in this case, like just a complete cog in the giant machine. That case settled and I was like, “Okay, things are going to get better.”

Jessica Medina: I love this, Sarah, a once in a lifetime opportunity to be on a case that settles. That is not a once in a lifetime opportunity.

Sarah Cottrell: It was some kind of opportunity. I think at a certain point—and again I'm speaking specifically about my experience in Biglaw but I'm sure that this happens in other types of practice as well—when someone's like, “Oh, I have this case and it's really unique. It's going to be just a really great opportunity.” You start to realize like, “Oh, let's go for something else. Let's go for something that I actually don't want.”

Jessica Medina: Let's go for a work that’s all-nighters. That's great. So your case settled, then there's more work, “Hey, look at that.”

Sarah Cottrell: Yeah. That was the point that I really started to recognize that my inability to disconnect from the work was really challenging. It wasn't in a workaholic sense. I think that there's workaholism and that's one thing but for me, even when I wasn't working, this was back in the BlackBerry days before everyone got iPhones, but at any moment, I knew something could come in to my phone and the little red light would blink on the BlackBerry, and it would just be like, “Oh, I thought I was going to have a normal evening and now, I'm working until the wee hours” Or it's Friday at 4:55 and an email comes into my inbox, and it's like, “Oh, your whole weekend is blown up.”

Some people I think have the ability to compartmentalize when they don't have something, where they're like under the gun, they can just be like, “Okay, it's fine.” Then when something comes up, they can roll with the punches. But for me, I felt like I was constantly walking around with this sense of foreboding and doom. One, based on reality, I had many, many experiences where I had plans to meet friends, then had to be like, “Sorry, I have to go do this thing.” Or my husband and I, we both worked in Biglaw, so many times, we had plans to take a trip over the weekend or whatever, then it ended up getting canceled because one or the other of us had something come up. Part of the problem I think for me was not just that I had not great boundaries with work because of my identity as that person who achieves, works hard, and is available. It wasn't just that. It was also that it was rewarded. I observed that people who had better boundaries than I did were perceived as they're not a team player, they're lazy, they're not reliable. It was this toxic combination of my own boundary issues with work but then also, the environment itself rewarding and holding up a lack of boundaries as like the model to aspire to.

Jessica Medina: Yeah. I can't think of the word, what is it when you fall in love with your captor?

Sarah Cottrell: It's Stockholm syndrome.

Jessica Medina: Yes, Stockholm syndrome. All of us are captive and we hate the people who want to escape. Don’t worship our captors who don't worship the system that we exist in. I totally agree with you. I think that there is this theme that if you are not 100% devoted to your clients, the work, and the practice of law, which is equated with basically self-flagellation all day long, flagellation by others, and just like punishment and overwork, if you are not bought in on that, if you don't value that, you are not a valuable associate. There's something wrong with you. Only people who are outside can see how twisted this all is. But when you're inside, you're surrounded by other people who've all drunk the Kool-Aid. I can totally resonate with that.

But tell me, it sounds like you had this moment in the sun but then that moment passed and you went back to work, you kept doing your stuff. Was it like a slow burn? When did you consider, at least, this firm might not be the experience for you and you might need to do something else?

Sarah Cottrell: One thing I just want to mention before I move on that came to mind when you were just talking just now is that I also think that there is this narrative of this is the way you work as a lawyer if you really care about excellence. This is the way that anyone who cares about being a truly excellent lawyer, this is how they work. Any other thing that you go and do that's different from this way of working is, in some way, beneath you. You'll be bored. That's often an idea that's floated around like if you go and do something that's less demanding on your time, you just couldn't possibly be fulfilled in that role. I think that it's so pervasive, that you don't necessarily question it because it's just the belief of everyone in that environment. I think that there was a period of time early on where I just absorbed those ideas. But then pretty quickly and honestly for me, what saved me was how miserable I was.

I've shared this many, many times at this point on the podcast but, fast forward, after I ended up leaving Biglaw, I was diagnosed with generalized anxiety and panic disorder. Looking back now on my experience when I was still at the firm, I can see how that level of misery was definitely exacerbated by my clinical anxiety. I just didn't have language to even know that's what was going on.

I went through what I think of as the traditional progression that many lawyers go through mentally when they're like, “Oh, I don't really love what I'm doing.” I was like, “Oh okay, maybe it's just litigation.” Because of course, there are many things about litigation that I didn't like. I'm very conflict averse, so litigation is a terrible field to be in if you don't enjoy conflict and if conflict is draining to you. I was like, “Should I think about going into corporate?” I had a friend who was similar to me in a lot of ways and I thought, “Well, she seems less miserable than I do, maybe that would work for me.”

First, I contemplated like, “Maybe, I need to go somewhere else inside of this firm.” Then I was like, “No, I think Biglaw is more or less the same everywhere, maybe slightly different on the margins but I think I definitely want to get out of Biglaw.” But at that point, I was not thinking about leaving the practice of law or significantly changing what I was doing. I think a big part of that was I'd just gone to law school, graduated, passed the bar, and had only been practicing at that point for maybe 18 months. It just didn't even occur to me like, “Maybe, this means something more than just I should go to a different firm.” I started looking at smaller firms because of course, at least as a litigator, there's this like, “Oh well, maybe I'll be happier if I'm more hands-on and can be more involved in the individual cases, etc.”

I applied for some jobs at smaller boutiques. I got some interviews. Again, I know I've told the story before but I was driving to the very first interview at this boutique firm. It was for a trial associate position with some appellate work involved, which is something I was interested in because, again, research and writing. I'm driving down the highway in Houston like, “Okay, I'm going to this interview,” thinking through what I'm going to say to the various questions. I just had this moment where I realized, “I don't want to do any of the things that I'm going to have to tell them I want to do in order to get this job,” like, “Oh, I really want to do more depositions, no. “Oh, I really want to be able to argue more in a trial or stand up in front of a judge,” no. None of those things were remote, not only was I not interested in them, I actively was like, “That sounds terrible.”

I had this realization five minutes away from the interview, I wasn't going to cancel, but I'm sure it was the worst interview ever because I basically had this seismic world rocking realization of like, “Oh yeah, no, I don't want to do this and I don't even want to pretend that I want to do this.” I can remember looking back, even on OCI, for me, there was an element of it where it was like a game and I don't mean a game like I wasn't being myself but I just felt like, “Okay, this is a thing.” I approached it like I approached everything else in my life at that point, which was like, “Okay, this is the thing that I'm supposed to do, I'm supposed to go, and I'm supposed to get callbacks. The goal of this is to get callbacks.” That was what I was focused on, not “do I genuinely want to be doing the job that ultimately could result from me getting a callback to this firm?”

I was very successful at achieving the goal but the goal was getting the callback, it was not like thinking about the broader picture of like, “Is this actually something I want to actually be doing?” Anyway, I went to this interview, had this realization, and at that point basically, everything shifted because I realized like, “Oh, I actually don't want to be looking for any job that is like a traditional practicing job.” This was about two years into my career in Biglaw. That was really scary because I have student loans and I have no idea what I want to do. I went straight through from undergrad. If you asked me what I liked, “What do you like to do?” I'd be like, “I don't know because my entire life is work, being a lawyer, and making sure my life doesn't totally fall apart,” like picking up dry cleaning and just basic life maintenance stuff.

I know I talked about this a lot but I just remember scrolling—at that point, job boards were not as popular, it was more like Indeed—it was just like scrolling, hoping that some job would magically appear and I'd be like, “Oh, that is my answer.” Clearly, that is the thing for me. Spoiler alert, that didn't happen. But through a completely random set of circumstances, we had a friend who was going to law school in Houston. We had dinner with them and they mentioned that they were interning at this legal publishing company, which is based in Houston, which publishes these books that I used all the time in my practice. I went on their website and they had positions open for legal editorial assistance, which was literally like one-sixth of what I was making as a Biglaw associate at that point. But at that point, I was so miserable. I was in the realm where I would get an email with some work. It wasn't even super stressful. It wasn't necessarily like, “Oh, you're going to be up all night working on this.” It was literally just an email with something that needed to be done and I would start crying. Just things like that.

My husband and I had many conversations, he also was in Biglaw, like I said, so he understood the dynamics and we both came to the conclusion that, “This is just not good for me.” At the time, I couldn't completely articulate why that was but it was like I just needed to get out. I will pretty much take anything to remove myself from this situation, which I just want to say that there are a lot of people, and I talk to a lot of people now who say like, “I don't think I'm depressed. My job is just really horrible and makes me feel depressed.” That's definitely what I would have said at the time. I think there is some truth to that but I also think there is a point at which the environment that you're in can be so toxic for you and for your mental health. I mean yes, this idea of like I wasn't actually depressed, that my job was just making me feel depressed was true but that doesn't mean like, “Oh, you should just keep doing the thing you're doing,” like experiencing misery and not finding a way to free yourself from it. Anyway, that's a bit of a tangent but I ended up getting the legal editorial assistant position. I gave notice. I'm quite confident that most of the people I work with thought that I had absolutely lost my mind.

Jessica Medina: That is often the reaction. I want to touch on something that you mentioned. I think law has this particular aspect to it, and a couple of professions do, where just the idea of being a lawyer has this value in and of itself, you can call it prestige, you can call it whatever you want, but there's something about that intrinsic value that you get just from thinking of yourself as a lawyer that helps you gloss over so much of the actual practice. I didn't like taking depositions either. I was a litigator but I liked calling myself a lawyer. I liked being a litigator at a major firm. I think some of that creates this very high tolerance for pain that you would never accept or be willing to take in a different industry if it weren't balanced by this innate thing that you think is really important and is providing you some “fulfillment” even if it is feeding into your own achievement-oriented self-worth stuff. But it does create this weird combination of like, “I just want to be a lawyer,” and “Oh yeah, it doesn't matter if I actually like the job,” versus if I were in a different industry, I'd be like, “Oh no, I don't like this work. Let me do something else.”

Sarah Cottrell: I think the other thing that comes up a lot is that there is this level of misery that is normalized in the legal profession in general and in Biglaw in particular, in my experience, where you don't even consider like, “Oh, the fact that I'm crying all the time or the fact that I just feel emotionally crushed or the fact that I truly feel like I hate this job and everyone else around me basically feels the same, that doesn't really mean anything.” It's just like yeah, everyone feels that way but that shouldn't prompt any different decision making. I think for me, there was some element of that as well where early on, it was like, “Oh, I guess we all just feel this way and that's just what we do.” You do have to do a little bit of work to be like, “Oh wait, no, I actually don't have to just accept this as this is just what we all do.”

Jessica Medina: A lot of people I think, it takes getting to a really serious breaking point to actually release yourself from whatever the situation is. For you, the idea of just getting an email regardless of the tone, regardless of the request, regardless of what the email had to do with, just that being enough of an event to cause a huge emotional reaction, big sign, big sign, and your body is just like screaming at you.

Sarah Cottrell: Yeah. I will say this is also the time, the point at which right before I left to take the job in legal publishing was when I had the idea for The Former Lawyer Podcast. My husband and I would walk around our neighborhood at 10:00 at night because it was the only time that we both were more or less free and could be outside, and would talk about all sorts of things. But of course, one of the things we were talking about was how I felt about the job. I was going through this process of realizing, “Okay, people say you can do anything with a law degree but what does that actually mean?” Because I actually want to do something else with my law degree. I have no idea what that looks like. I'm looking for information about what people do. It's just like there isn't a lot of practical information. There might be an article with a list that’s like, “You could do compliance.” It's like, “Okay, but what does that mean? Is that actually something I even want to do?”

So I had gotten into listening to podcasts at the time. We were talking, it was like, “There needs to be a podcast called The Former Lawyer Podcast where people who have left and done other things talk about what it was like, and how they got there because this is information that people need.” That was in 2011, we bought The Former Lawyer domain, so I knew I wasn't going to be leaving law most likely anytime soon, primarily because we wanted to pay off our student loans, which is a whole separate discussion, but it was like, “This needs to exist. I know that this needs to exist in the world. Someday, it will happen.”

Jessica Medina: Oh, I love the foreshadowing. I also love that you bought the domain. That's a really important action to say that this is going to happen in the future. Of course, I was going to ask you something like, “Hey, tell us how you got the idea of the Former Lawyer?” I like that it happened while you're still in the legal publishing world. You still have a foot in law, just not in the same way that you were practicing before. You obviously are no longer practicing or working for a legal publishing company, but tell us about the rest of that journey to actually leave being a lawyer.

Sarah Cottrell: I went to the legal publishing company from Biglaw and it was wonderful. I was there for a year. I call it my year of vacation. It was just that I really needed something that was completely opposite from the work environment of Biglaw. That's what I had there. To be honest, what happened was that I've recovered. Towards the end of that year, I was like, “This is actually a little bit too mellow for me. Yes, I'm really working on the whole idea of boundaries with work. For me, it needed to be that my work itself had better boundaries.” It wasn't constantly trying to push my boundaries. I felt like I'd gone from 90 miles an hour to 10 miles an hour and I was like, “Can we get in the 50-mile per hour range?”

Jessica Medina: Oh no, you were bored. It happened, oh no.

Sarah Cottrell: Yes, I was bored, which was amazing, then eventually was like, “Okay, I need to slightly do this a little bit snappier.” I had some friends and some former coworkers who worked at the First Court of Appeals in Houston, state Court of Appeals and there was a job opening there. I ended up getting hired at that Court of Appeals, which was, in many ways, the thing that I had always thought I would like the most in the whole world of lawyering because working at an appellate court, there's tons of research, reading, and writing. That's basically all that you're doing. You're not so much taking a position, you're just looking at all of the arguments and trying to come to the right conclusion based on what the law says, and the standard of review and all of those sorts of things.

It just really, for me, was a much better fit, both substantively in terms of the substantive work but also, I found it to be just a much better situation in terms of work-life balance, which I hate that phrase. But basically, I would go to work, I would work hard but I would leave work around 5:00 PM. Once I was not at work, I wasn't doing work at home, I wasn't working at night, I wasn't working on the weekends. But I had to work hard when I was there. The work itself was interesting but it didn't spill over into the non-work time in my week. I thought that it would be a good fit for me and it definitely was. I was in Biglaw for almost three years, I was at the legal publishing company for a year, then I was at the Court of Appeals for six years. The Court of Appeals job for me was like there was not going to be a better job as a lawyer, for me, Sarah Cottrell, for this person, who she was, what she liked, and all of that stuff.

I think knowing that, having that experience, and realizing like, “Oh, but I still don't want to do this forever,” was what really brought me to the point of being able to say, “This just isn't for me. I don't want to be a lawyer for the rest of my life.” I think not everyone has to take that many years to figure that out. I was doing a lot of things on parallel tracks. I was finding a type of work that fit me better. I was also working on some of the issues of my identity being wrapped up in being a certain type of person, like working in a certain type of way so I got into therapy when I was 30. I'm 38 now, so that was a big piece of it for me, then also discovering that I had clinical anxiety, what that meant, how did that play out, and how did that intersect with my work life.

Also, really sincerely for the first time, being able to figure out like, “What do I actually like to do? How do I like to work?” just all of that stuff that I hadn't really ever dug into when I was coming out of undergrad was not even part of the equation. All of those things together were things that I had to work through in order to get to the point where in 2018, we paid off our student loans, our combined student loans. I was pregnant with our second daughter, she was due in July and I had originally planned to go back to my job at the Court of Appeals, then in late spring, we were looking at our finances and realized, “Oh, we're going to pay off these loans.” This was before I went out on maternity leave. This was the point at which I had told myself in my mind like, “I could do something else.” It was like, “Oh, that point is here. I can do something else.” So I decided I wasn't going to go back.

Jessica Medina: You know I want to ask you about the money, but let me sprinkle in a question from one of your audience members. You've talked about starting therapy. I know that this is something that you talk about on the podcast and basically, all respects about how important it was about your journey and how really everybody should have it, which I totally agree, but tell us a little bit about what is your advice for folks who are looking for a therapist and want somebody who understands what it's like in the legal field to be a practicing attorney, and to not have to explain why billable hours are what they are and why they are soul crushing. How did you go about finding a good person for you? Do you have advice for people who are looking for a good therapist for themselves?

Sarah Cottrell: I was extremely fortunate that the first therapist who I got a recommendation for—I actually got a recommendation from my pastor—just so happened to be a really great fit for me and all the various things that I was working through. She did not have past corporate experience. I think that you don't have to find someone who has that to have someone who can empathize. I think the concern people have is that they're going to go in and a therapist is going to be like, “Well, you should just tell them you're not going to work after 5:00 PM or whatever.” At least for someone who is in a position like I was when I was in Biglaw, there are boundaries that will work, then there are boundaries that are like, “Okay, but if I want that, I literally need to find another job.”

The general advice with therapists is like you just have to pick one, go, and see. In fact, the research shows us that it doesn't even necessarily matter what methods or theories your particular therapist is working from. The most important thing is your connection with that therapist. Because it's not something you can just research and be like, “Oh, this is a person who I’ll have a great connection with,” it is a matter of just “Get some recommendations from people who are local to you, go see someone, and see if you click.” There are some therapists who were previously lawyers. I'm actually interviewing someone in a couple of weeks who went back and got her master's degree in counseling, and is now a therapist. I think you certainly can. There certainly are former lawyers who now are therapists and specialize in working with people who are lawyers. That's definitely a possibility but I don't think it's in any way necessary. I think that you can trust your gut when you're making that decision. You just have to get in a room with someone or get on Zoom depending on what your situation is. That's what I would say to people who are thinking about finding a therapist.

Jessica Medina: Sometimes, you gotta rip off the band-aid and get in there, try it out. It's always nice when somebody understands your shorthand but many therapists know how to work with high achieving, highly paid, highly stressed out individuals. As much as we love to think of lawyers as this special snowflake case, there actually are people in the world who have similar issues in different industries. Therapists are trained to work with all kinds of people. But I think your point about just finding someone that you connect with, that's the most important part. If you feel uncomfortable sitting on the couch, go find somebody else. It's okay. Just make sure that discomfort is actually coming from your relationship with a therapist, not your own issues and having to look at your own issues.

Sarah Cottrell: Yes, it's so true.

Jessica Medina: Okay, 2018 paid off the student loans. As a financial counselor who works with lawyers, this is a watershed moment in most people's whole career. Were you waiting for that moment specifically? Did you guys ever discuss, “Hey, we could do this even sooner,” because maybe you were in so much pain or was the fact that you were in basically, your dream lawyer job enough to sustain you until you got to that point. Tell us a little bit about that decision-making process.

Sarah Cottrell: One of the things I always try to be clear about is I do not think that was the only acceptable choice and there weren't a lot of other options. I think even now, some years on from that, I realized that there were probably even more options. But part of it was like for me and for us as a family, our oldest was born in the spring of 2015, then like I said, our youngest, she was born in the summer of 2018. I think that if we weren't having kids in that period, then maybe in that 2014, 2015, 2016 time frame, I might have started thinking about things like, “Oh, can I move on and do something else at this point?” But one, for me, I was a little bit too tunnel vision on paying off the loans. I know you and I have talked about this before. Once you reach a certain point, there really are other options beyond just being like, “I just have to pay off the loans.”

One, I think there was a level of tunnel vision but then also, I was having my first kid and going through the first year of being a parent, which I love my kids and I love being a mom, but I am not the person who's like, “Oh, the baby face is so easy . They just sleep everywhere.” Whatever the opposite of that is me. For me, that first year in particular was just like a get through. I personally just didn't have the bandwidth to be in which I might further self-actualize. It was more like, how do we keep the ship on course. I think the combination of that plus, like I said, for me, I was a bit of tunnel vision, I'm paying off the loans. It was like I didn't even really think about, “Do I have other options at this point?”

Jessica Medina: Let's not underestimate. Children are about as expensive as a law degree.

Sarah Cottrell: Yes.

Jessica Medina: That is a real expense. The second one might not be as expensive as the first, but certainly, children are not an immaterial addition to your budget, especially not really knowing. So 2018 came along, you did make the decision to leave the law entirely. I imagine there were a myriad of emotions that were going on, but you had been doing some of this work, walk us through what that felt like and some of the things that you butted up against while you were making that decision or even soon after.

Sarah Cottrell: For me, I had practiced law for 10 years. I had at that point spent many years in therapy, many years contemplating the ultimate goal, which was to leave legal practice. I think the point at which I made the decision like, “This is happening now,” I think a lot of that internal wrestling had already occurred. Working through these issues that we talk about on the podcast all the time that come up so often with the people who I'm working with in The Collaborative, things like “Who am I if I'm not a lawyer? Who am I if I'm not the person who is the highest achiever? Who am I if I'm not just the gold star getter?” Those were things that I think I had worked through, especially for me, learning more about the experience of clinical anxiety and just understanding the role of limits. The fact that I'm a human being who has limits, that's not a failure, that's not a problem. That's just a part of being human, and that my limits are going to be different than any other person. Everyone has their own individual set of limits, not just a fact that that's good. Our individual limits are part of who we each individually are as unique human beings. It's not something to feel ashamed about or to be like, “Well, I wish I had that other person's particular set of limitations.” It's just part of who we are.

I think for me honestly, I'm forced by my anxiety disorder to accept that we all have weaknesses. We all have areas in which we fail—and I don't mean fail like negative, we are by definition imperfect—I think for me, the process of coming to some of those realizations in a very real way as a result of my diagnosis, then just learning how to live with an anxiety disorder, that for me is what really brought me to the place where I was able to feel confident in myself like, “I am Sarah. Who I am as a person is not dependent on various facts about me. My value comes from my inner self.” That is why I say every lawyer should go to therapy because that stuff is way beyond like, “What do I like? What tasks do I enjoy?” But also, I think that's what enabled me to be able to say, “I'm walking away from this thing. I'm not feeling guilty about it. I'm not hiding. I don't need anyone to approve. If someone disapproves, I don't need external approval to feel okay about this choice.”

Jessica Medina: Yeah, I think some people think that it should go quickly, that you should just be able to drop the lawyer title and step into something else. But you had six years working with a professional.

Sarah Cottrell: Yes.

Jessica Medina: Thank goodness you're here now to make the path faster for other people.

Sarah Cottrell: This is why I say, “Please, let me help you.“ I do not regret any part of my story or the path that I walked but looking back, I can see how some guidance, some structure, just some understanding of where I am going and why, would have been very helpful.

Thank you for listening to this episode. That is the first half of my conversation with Jessica. We are going to pick up next week in the second half where I share more about how I actually ended up leaving law and all sorts of other things. Stay tuned, until then. As always, thank you 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 Until next time, have a great week.