The Long Process Of Leaving A Legal Career with Ed Cottrell [TFLP150]

Lawyers are under constant stress and pressure yet always have a “this is fine” mentality. “Everything will be fine,” we keep telling ourselves. But, is it really fine? And, is “fine” good enough? 

This week, you’ll read about Ed Cottrell, a former lawyer and most importantly, Sarah’s husband. Ed had a legal career for 13 years before leaving the law for a job in legal tech. You’ll notice the ever-present theme of “just fine” in Ed’s legal career journey. 

During their conversation, Sarah and Ed spoke about the positives and negatives of his legal career, how his experience intersected with Sarah’s, and ultimately, how Former Lawyer came to be. 

Sarah and Ed had so much to discuss that this article is divided into two parts. So, without further ado, let’s get into it! 

Starting The Journey To A Legal Career

Ed and Sarah began their conversation by talking about how they met. In 2005, they began law school at the University of Chicago and were in the same writing section. They also lived in the same apartment building and regularly ran into each other, which began a great friendship. 

He asked her out, but she refused because he had done it incompetently. So, he made another attempt, and this time, she said yes. Of course, they hit it off, eventually getting engaged and married. And here they are, over 15 years later. 

Years before that, Ed was just out of college, and the only thing on his mind was finding a job. He funded his way through college doing freelance software and website development, so decided to pursue that for a couple of years.  

Ed wasn’t sure where his career path was heading. He thought about multiple options like teaching, getting a Ph.D., and being a financial advisor. But, none of these seemed like tantalizing options.

At the same time, Ed was working on some software for lawyers. He became interested in the legal side of things, especially contracts. That experience made him think that law school would be the perfect solution. He’d practice for a few years and become a law professor. 

Law School Experience

Ed had fun in law school for the most part. He enjoyed what he was learning but quickly realized that what he hated about the law was legal academia. In his Elements of Law class, Ed read The Crystalline Structure of Legal Thought by Jack Balkin. This article boils down to making a decision, which presents a new decision, and then a new decision based on that, etc. Basically, everything in life is a decision based on previous decisions. 

This article struck Ed as the most obvious piece of writing he had ever read, but it was a long read. And during that read, Ed realized that a legal career was not what he wanted. But, he decided to stick it out and continue his journey on the conveyor belt to a legal career. “It’ll be fine,” he said.  Little did Ed know how much the phrase “it’s fine” would appear during his legal career. 

He also quickly realized that his grades, while not bad, weren’t high enough to get court clerkships. So, he started thinking of a legal career within a firm. He had a good setting for a career without all the brass rings, and it was fine with him. 

After Law School

After law school, Sarah and Ed moved down to Houston, and both got positions working at Baker Botts. Ed got a lot of responsibility for some big cases and got to work with people around the world at this new job. 

A year in, an associate abruptly left the firm just as Ed started on a new case. The partners couldn’t find anyone to replace the senior associate, so they presented it to Ed, displaying it as a huge opportunity. 

Ed took the chance and went through a series of trials and related proceedings, which were disillusioning. He realized how difficult and exhausting it was to bring a case like that to trial and the ridiculous hours he had to work to achieve that. 

There were some enjoyable parts about Ed’s trial work. He enjoyed the problem-solving experience and learning how the legal system worked. Lacking experience, he saw a new motion or deposition as an interesting nut to crack. 

Intersection Of Opposite Experiences In A Legal Career

While Ed had enjoyable moments in his legal career, his wife, Sarah, wasn’t sharing the same experience. Even though they were working at the same place, for the same partners, Ed and Sarah did different types of work and experienced two sides of the law. 

Eventually, those two experiences intersected. Sarah had a difficult time with her legal career and ultimately decided to leave. Over time, Ed started to have the same realization. 

It was a challenging time for both of them, but it became increasingly apparent that a legal career was not the right path for Sarah or Ed. Again, Sarah left. But, Ed decided to stay for a bit longer. 

Just as Sarah was starting the process of leaving a legal career, Ed was getting ready to take a long-term case to trial. He focused on this case with better opportunities for the future in mind. Again, it was fine. He even went into the office on Saturdays. He thought of this as the same dedication as the retired partners showed when they came in to do pro-bono cases. 

But, Ed soon realized that they only did that because they didn’t know how else to spend their time. Ed decided that this wasn’t the life he wanted to live. He wanted something more than just “fine.”

Trying To Find “More Than Fine” In A New Firm

He ended up at another firm, which wasn’t the original goal, but it gave him some great opportunities. The firm had a “no screamers” policy which, as any lawyer knows, sounds great after being in a large law firm. So, Ed joined. 

It was a slower pace, which he liked. Ed also liked the people he worked with and the work he was doing. It was great…for about nine months. A partner called Ed into his office for a few minutes of assistance, which turned into more than 900 billable hours in three months. 

While working for this partner, Ed experienced a lot of workplace abuse, even getting insulting midnight phone calls followed by phone calls praising his competence. It was completely insane. Ed wasn’t allowed to delegate anything, so he carried a heavy burden for this time. 

Ed went to the other partners about this abuse, but they gave him no support or accommodations. He knew that a case like this would last five years at the least, and he wouldn’t be able to withstand this partner for that long. 

But, at the same time, Ed felt that leaving would jeopardize his career, so he needed to get through it, at least until the first trial was over. That was his end goal, so he put his head down and focused on that. 

The Long Process Of Leaving A Legal Career

While he made the plan to leave, Ed wasn’t ready to completely give up his legal career. But he was at the point where he couldn’t practice like that anymore. So, he searched for and found a new job at the Court of Appeals, again getting to work at the same place as Sarah. 

He stayed there for a few years, working with judges and helping to advise on how cases were considered. Then, Ed and Sarah welcomed their first child, and Ed decided to take some time away from his legal career. 

At the same time, Ed had ongoing relationships with his former software and web development clients. So, he worked in that area for some time. Then, he thought about doing that as a post-legal career. He had an idea to work with, so he decided to work on that for several months. 

Unfortunately, the idea did get the legs Ed hoped for, so he went back to work for the Court of Appeals. This time, his priority was for him and Sarah to pay their school loans. While looking around for a new firm, he heard of an opportunity in a Biglaw firm. 

It was around three years after his negative experience in Biglaw, so he decided it would be alright to go back. The role was a legal tech role, where he’d work on software development. 

Stay Tuned For Part Two Of Leaving A “Fine” Legal Career For Legal Tech With Ed Cottrell

Again, since Sarah and Ed had so much to talk about, the conversation has been split into two parts. To get notified when part two is available, you can subscribe to the podcast and blog! You can also subscribe to updates by downloading Sarah’s free guide “First Steps To Leaving The Law.”

And, if you’re looking for a better support network for as you begin your process of leaving a legal career, the Former Lawyer Guided Track is coming back this fall. This program takes you through the framework of the Former Lawyer Collaborative within a small cohort of people. 

In the Guided Track, there is a week-by-week action plan designed to take you through the framework in 10 weeks. There are weekly calls with Sarah and the group. Calls are at 8:00 PM EST  on Tuesdays, where the group gives progress updates, discusses any issues, and gets answers to any questions.

Also, as part of the Guided Track, Sarah is bringing in a GALLUP Certified Strengths Coach to run a half-day virtual interactive workshop. You will get a free Clifton Strengths Assessment and 34 Report. You will also get custom analytics that elaborates on how your talents drive your motivation. Plus, there will be hands-on exercises for gaining additional insight into how your strengths relate to your potential career path.

In addition to that, your enrollment also grants you membership in The Former Lawyer Collaborative so that you are supported beyond the 10 weeks of the Guided Track. When you enroll in the Guided Track, you get access to the Collaborative immediately.

If you’ve thought about working with Sarah, and you need support but are not ready for one-on-one coaching, this is the perfect package for you. And if you have any questions, you can email Sarah at [email protected].

Mentioned In This Article:

The Crystalline Structure of Legal Thought by Jack Balkin

First Steps To Leaving The Law

Former Lawyer Collaborative 


Clifton Strengths

34 Report

Connect With Ed:




Sarah Cottrell: 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, I am super excited to share this conversation with you today. This conversation is with my favorite person, my husband, Ed Cottrell. We'll talk about this more as we get into the conversation. But Ed and I met in law school. He practiced law for 13 years and just this past spring, he left the law for a job in the legal tech space and he is now a former lawyer. We talk about his process and also how his process intersected with my process and also the building of Former Lawyer. We had so many things to say that this conversation is going to be split into two parts. So please enjoy the first half of my conversation with Ed.

Hi, Ed, welcome to The Former Lawyer Podcast.

Ed Cottrell: Hi, Sarah. Glad to be here.

Sarah Cottrell: Oh, sorry. It makes me laugh. So you're my husband, I know lots about you, but why don't you introduce yourself to the listeners?

Ed Cottrell: Hi, everyone. I am at Ed Cottrell. As Sarah said, I am her husband. I met her in 2005 when we had both just showed up at the University of Chicago Law School to get started there. We were in the same writing section. We lived in the same apartment building. We just generally were crossing paths a lot and got to be good friends. I asked her out. She very wisely turned me down because I asked her out incompetently so I asked her out again. She said yes. It went pretty well. We got engaged. We got married. Here we are almost 15 years later.

Sarah Cottrell: Yeah. It's The Former Lawyer Podcast, and we met in law school. You were a lawyer. Are you a lawyer now?

Ed Cottrell: No, thank goodness.

Sarah Cottrell: All right. We're going to go back to the beginning, the way that we do with pretty much everyone on this podcast and I would love for you to tell the listeners what made you decide to go to law school.

Ed Cottrell: Well, back after college, I needed to find a job. I had partially funded my way through college by doing some freelance software development and website development. That's what I did after college for a couple of years. I helped my dad to get a business up and running. That was going to be his project going forward.

But I wasn't sure exactly where I was headed. I thought about teaching and I thought about going for a PhD so I applied for some PhD programs, rethought that a little bit along the way as I talked to some financial advisors and looked at different departments, wasn't sure that was quite right. But I started working at the same time on some software for some lawyers.

I got really interested in the legal side of things and the contracts we were working on with our own customers and clients. That made me think, “Law school sounds like a great idea. I'll teach law.” I went off to law school with the idea of “I'll probably practice a year or two and then I'll find myself at some law school as a professor, and life will be grand.”

That was almost all the thought I put into it. I had a little bit of an idea of what lawyers did, but only certain types of lawyers and I had a little bit of an idea of the salary escape and I went off a little more equipped than the average student I think, but not fully equipped.

Sarah Cottrell: Okay. Let's have you tell the good people how your law school experience was. First of all, we both went to law school thinking we wanted to teach so can you talk a little bit about what happened for you with that once you got to law school?

Ed Cottrell: Yeah. I had fun in law school for the most part, and I enjoyed a lot of what I was learning, but I realized very rapidly that what I hated about it was the legal academia piece of it, that the things I thought I wanted to do with my career were just important to me. One of the classes you take when you go to University of Chicago is called Elements of the Law, which is kind of a basic intro to how lawyers think and how our legal system works.

It's like, “Here's a Supreme Court and below that are these other courts,” all the really basic stuff that you hopefully kind of have a sense of, but really don't. Along the way in there, we read this article by I think it was Jack Balkin, this article about The Crystalline Structure of Legal Thought, which boils down to you make a decision, and then that presents you new decisions, and you make decisions based on that and you make new decisions based on that.

It struck me as one of the dumbest, most obvious pieces of writing I'd ever read, but it was I think 120-pages or something awful and I realized, “I do not want to do this.” So I very rapidly just said, “Okay, lawyers are big firms that make lots of money, and that seems to be the conveyor belt here. I'll just hop on the conveyor belt and it will all be fine.”

Sarah Cottrell: So tell me what happened next.

Ed Cottrell: Well, law school happened next. My 1L year was pretty good. My grades were fine. I've never been obsessed with grades but I realized how important 1L grades were. I also realized that they were not going to be the kinds of grades that got me like put in court clerkships or something like that. So I started to think, “Okay, well, like I said, this law firm thing doesn't sound so terrible,” but I did fine.

I ended up working for a professor my first summer and at the end of the first summer when you start doing OCI and all that, I got offers from pretty much anywhere I thought I might even be open to working. That went well enough, and I had made it onto a journal and I was signed up to do moot court and I thought, “I've got the settings for a good legal career here that's not going for all the brass rings that people might sometimes go for but this is fine.”

Sarah Cottrell: Ah, this is fine.

Ed Cottrell: This is fine.

Sarah Cottrell: Always what you're hoping to feel as you embark on your career. Let's fast forward a little bit to graduating from law school and tell me, you graduated, you started working, how was that for you?

Ed Cottrell: As you obviously know, Sarah, we both ended up at Baker Botts down in Houston, which is and was one of the more prestigious firms in Houston. So that sounded great to me. We had to pick between Chicago and Houston because those were the two cities we’re really open to living in. We liked Chicago, but it was cold. We liked Houston but it's hot, and it's cheaper was largely what tipped the scales because we were coming out with two pretty large loads of student loan debt and looking for somewhere that pays well and it's cheap to live.

Of course, I've been in Houston for undergrad so at least I had a pretty good sense what it was like. You only visited during thunderstorm weekends as I recall so you got the worst taste of the weather in the world. I don't know how you get that in there. But anyway, that's where we ended up and I thought it was pretty good at first.

I got staffed on a couple of interesting things. I got a lot of responsibility for some very large cases in terms of dollar value. I was working with people all over the world at first and I thought this is really interesting. A year in, a seventh-year associate left the firm pretty abruptly and I had just started out on this case as a rising second year, providing some basic grunt research type support, just doing some memos and things like that.

The partners couldn't really staff anybody on that, they couldn't find anybody to replace the senior associate that left, but they presented it as this big opportunity for me and they're like, “Why don't you just run with it for a while and we'll see what happens,” which turned out great because I got a ton of experience and I loved what I was doing for the first couple of years.

Then we had a series of trials and similar proceedings related to that, that were a little disillusioning to say the least. They were not the most confidence inspiring in the entire system. I realized just how hard it is to get to trial with one of those big cases. It was exhausting. I was working ridiculous hours, doing the thing where you're in court for eight-plus hours and then come home, or go to the office more accurately and work another eight hours, and then come home for real and work another two hours and try to sleep for four hours and go do it again. Did not love that.

Sarah Cottrell: Okay. Let's circle back briefly to what you said before you were talking about the trials which was like that it was great. Because when you say it was great, I mean, I know what you mean, because I know you and I know your experience. But, for example, doing depositions, not everyone would describe that as great. I, for example, would be like, “That is my nightmare.” One of the many reasons I probably should not have been a litigator. Can you talk a little bit more about what it was about that experience that was enjoyable for you?

Ed Cottrell: Yeah, sure. I actually enjoyed a lot of the problem solving and learning how the system worked aspects of it. Having never done something before, I was presented with a new motion or a new type of deposition or something, I thought that was a really interesting nut to crack, a problem to solve, and a thing to figure out.

I loved working with witnesses. We had a lot of opportunities to work with witnesses, including a lot of the experts and I loved it, especially adversarial witnesses because I really enjoyed the process of just getting people to open up and give away the farm as it were, by being a nice guy, not by being a jerk and yelling at the witness but just trying to get things out of them.

At first, I thought that was a lot of fun. I was getting to do a lot more of that than was normal for a junior associate just because of staffing issues and the fact that I knew the case so they were letting me do it. But it was not fun in the sense of lifestyle or something like that. My first full fiscal year at the firm, I think I had 2,400 hours. Right after that my pace picked up so much that I build more than 2,600 hours in a 12-month period even though, of course, it got split in such a way I think you credit for that within one year. But it was intense.

I know you've shared this story before on the podcast, Sarah, but when we bought our first home a year after we started practicing, the senior associate who was working on your case didn't even want to let you come send the paperwork with me.

Sarah Cottrell: Yes, because I was off at trial.

Ed Cottrell: Yeah, 20 minutes away.

Sarah Cottrell: Yeah. I was the lowest of the lowest associate in the massive conglomeration of 40-plus lawyers. That actually brings up something that I think would be interesting for people to hear. Can we talk a little bit about as your experience of this was going on, how my experience of it was intersecting?

To start, I just want to say to listeners, when Ed says, for example, he likes doing depositions, this was something that I was seeing very close up because we’re married, and we would talk about things, and it was one of the things that for me really illustrated, “Oh, I do not like this,” because some of these things are interesting to him and energizing in a certain way. For me, it's like, “If I could never do that, that would be amazing and I would really rather not.”

Having this experience of being in a close relationship with someone who just felt so differently about certain aspects of the work really made me see that it's possible to enjoy some of this and I'm just not someone who enjoys it.

Ed Cottrell: Yeah. I think we had just parallel experiences in certain ways in that I was getting to do a lot of “on-your-feet” stuff. I was going to court. I wasn't getting a lot of argument experience that first year or so but I started to, in my second and third year when you were still there too, I was getting a lot of the depo experience and doing tons of time actually first sharing, sometimes for other important depos, sometimes really minor ones, but I was in the stuff for like I’d get up in the morning and catch a flight out of Houston Hobby—which was not close to where we're living. Houston is big for anyone who hasn't been there—but I’d drive down to Hobby, catch an airplane at 5:30, fly to Denver, be there all day, and catch a flight back, that kind of thing.

There was one week in particular I remember where I flew to, if I recall it was Denver, and back, Atlanta and back, Denver, and back, I want to say somewhere in West Texas and back in a week. But I was kind of eating it up because I was getting to do all these contact things where I was in front of the client, I was in front of the opposing counsel, I was in front of the witnesses. I was the face of this huge corporation as far as these people were concerned. That was great.

You, meanwhile, were doing a lot more administrative type stuff where you had these dockets of cases and you were trying to coordinate five different cases that'd be filed on the same day and all that kind of stuff. I just wasn't getting that. I was doing motions but I had a motion for summary judgment or a whatever.

Even though we were at the same place and even working with the same partners and same other associates, a lot of times, we just didn't have the same experience those first couple of years. You were looking at what I was doing thinking, “Oh, that sounds terrible. I don't want to have to deal with that.” I was looking at what you're doing thinking, “Thank goodness I'm out on that docket.” Eventually the streams crossed and I think you were realizing this is not going to go well through the things I want to do in my life. I started to have that same realization a bit too.

Sarah Cottrell: Yeah. I think one significant part of the story is that we've already mentioned buying our first house, that was right at the end of our first year working at the law firm and it was not that long after that, that I sort of had the realization of like, “Oh, it's not just this one big case that I was on that I don't like, it's not just your first year is a trial by fire or whatever people say.” I really had the realization very soon after that we close on the house that I actually think I don't want to do this.

But it definitely took some time to get there. I would love to hear from your perspective what that process looks like for me from your perspective because I'm sure there are a lot of people who either are listening who have a significant other who is watching them go through that process or maybe is a significant other who's listening. Can you share a little bit about that?

Ed Cottrell: Yeah. I think part of it is if you're going to succeed at getting into law school or getting through to law school, navigating the interview process with law firms, which frankly is weird and nothing like any other interviews I've ever done, but anyway, if you're going to get through all that kind of stuff, then you're going to practice and you're going to manage the appearances of “How do I present myself in this moment so I don't give something away? How do I sit in court with a straight face where I know somebody just lie on the stand or said something I'm going to nail them to the wall with later or whatever? How do you do all that?”

Well, to do that, you have to learn to roll with the punches really well and put on a can-do attitude at all moments. For me, your dawning disillusionment looked like saying things like, “Oh, well, I don't know if I'm going to make it to this thing. You go and have fun, but I've got to work on this motion. It'll be fine. I'll see if I can catch up later.”

Or we had friends over one time and something came out on a Sunday evening. I think it was six o'clock or something. It allegedly had to be turned around very quickly. You're just like, “It'll be fine.” Anytime you said that phrase “It'll be fine”, I know it's not and it won't be. It's kind of an impending doom, but that's what it looked like for you.

I was going through moments like that on my own where I'd have something come up and ruin my plans and tell myself, “It's fine. It's paying my dues,” whatever. But the more phrases like that start to come up for you, the more I knew there was a problem. It got to a point where you were obviously struggling. I would know that you had cried at the office or I would know that you're crying at home.

I would watch you just kind of break down at the end of every day. You'd have to try to pull yourself back together and go do it again tomorrow. Because you'd say, “Well, I just don't know if I can keep doing this but I've got these motions that are due or I've got this whatever this due,” so you just do what lawyers do and you pick yourself back up and you put your shiny happy lawyer face or dour lawyer face back on, whatever the case maybe calls for. You go back and you crank out the work.

But it became very untenable because literally every night was becoming a process of pick yourself back up and put yourself back together. I know we talked about it a bunch of times, I didn't want to tell you of course “You have to leave. This unhealthy for you,” but it got to a point where I was trying very hard to nudge you that way. When you were finally like, “I don't know if I can do this,” I was like, “I think you're right. Do something different because this is killing both of us.”

To be clear, it wasn't an easy period for me either, for those listening I don’t want to misunderstand here. It was a challenging time for both of us, independently of how you felt about your job. But it was increasingly apparent that whatever happened going forward, a two-firm lawyer household was not going to be an option. That was just not going to work.

Sarah Cottrell: Yeah. I think one of the things that is important for people to hear is you were seeing the breakdown, but it wasn't like it was affecting my work. The people who I worked with, I mean I just don't think anyone really thought there was any sort of issue. Because like I’d said, through all of the years of becoming a lawyer, I had learned how to like, “Okay, this is what I'm going to do. It's mind over matter. This is my job. Whatever needs to get done, I will get done.” What you were seeing in terms of the toll that it was taking on me mentally, emotionally physically, was very different from I think what it would have looked like to most people.

Ed Cottrell: Oh, absolutely, absolutely. You were the quintessential compartmentalizer. You were able to put on your game face at work and compartmentalize all this until later when you couldn’t deal with it we’d go for a walk around the neighborhood or some couch and talk or whatever.

I know when you left, again, I was working with a lot of the same partners and a lot of the same associates and you've gotten all of the standard, “Why would you leave? Why would you give this up? You were ‘on track’?” all this stuff where it took a lot of people by surprise, and I think frankly shocked, maybe rocked a little bit some of the partners and associates in question who were women, and they were trying to have it all and do what you had been trying to do and found to be a little bit insane, they were unsettled, I think, frankly, by the fact that you admitted, “This is not for me, this does not work.”

Sarah Cottrell: Yeah. That's a conversation that we had a lot because, I know it's come up on the podcast before, but as a woman in Biglaw, you feel this kind of obligation to not quit, to show that you can do it because we all know what the stats are with respect to women and minorities in Biglaw, they're not good.

I very much had this sense of “I can do it so I should do it.” I think this whole process that you're describing really brought me to the point of saying, “I can do it but I don't have to. I'm allowed to make a choice that feels better for me,” which was pretty revolutionary at the time. But anyway, enough about me, let's get back to your experience. When I was in the process of “I have to get out of here. I will literally take anything,” what were you thinking about your legal career at that point?

Ed Cottrell: At the moment that you were getting ready to leave, I was getting ready for the big trial that I've been working towards almost my entire time in the law at that point. I mentioned a minute ago, I got put on this big case where I got to take over a lot of senior associate type roles and it had ramped up to a related trial-like proceeding that I can't get too much into, but that had happened already and our piece, my client’s piece was up.

I was just focused on that really. I was playing this big role in it. I wasn't going to have a big role at trial necessarily because there were so many eyes on this that there was going to be partners who did most of the lifting for various reasons. But I was very much going to be in the courtroom, working behind the scenes with all these witnesses and so on. So I was just really focused on that.

Part of that was things were going well for me at the firm. We were both on track but it wasn't miserable for me in the same way at the time. I had a goal I was working towards on your thing that just seemed to be a hydrant that never was going to die. But I had to leave something I was working towards and so it seemed like, “Hey, this is a little intense, but I'm building a good name for myself and I'm going to have lots of doors open for me and lots of opportunities so we'll see.” I don't know if I'll be here forever. I never really intended to be in Biglaw forever but at the time, I was thinking, “This is okay. We need to figure out where Sarah is and stabilize all that and we'll see what happens with me but right now it's fine.”

Sarah Cottrell: Yeah. Just for the listeners’ benefit, I would say that, at that point, I would say you thought Biglaw was terrible in the way that anyone sane thinks Biglaw is terrible, but it was not like we were not equally miserable, you were not in the “I need to get out of here” space.

Ed Cottrell: Yeah. I was doing the thing that you do where you go into the office on Saturday because why? I don't know. But we needed to be there for something even though it could have been done remotely. There were a number of retired partners I would see kind of wander around the office and based on what I've been told, I thought a few of them had some little pro-bono matters and so on. I started to realize a lot of them just didn't know what else to do with their time. They really didn't know where else to be on Saturday morning.

So I made the decision that I don't want to live that life. That's not for me. I knew that I didn't want the life or lifestyle of some of the people I've gotten to know best and worked with the most at the firm because okay, one week of wake up, go to the city, go to the city, go to the city is not so bad, but doing it three weeks out of the month, that no, I knew I didn't want that.

I was definitely trying to plot the path that didn't look like certain people, including certain people who could be called my mentors, but at the same time I wasn't like, “Okay, this is impossible. I gotta go.”

Sarah Cottrell: Yeah. Tell the people what happened next.

Ed Cottrell: That big case wound up and I did get a few other interesting opportunities and by the standards of big firm litigation, I was getting good work. I was working on this huge arbitration and I was getting into the first year of this and I was getting to do that. I was getting experience actually trying little cases for this little program we had set up for that kind of thing.

I was getting lots of great experience. But I realized also at the same time that those experiences were drying up, they were becoming fewer and fewer due to some firm politics considerations based on people with whom I was associated and where I thought their careers were going, due to the simple lack of real on-your-feet opportunities for most associates in a big firm context, etcetera., I realized this is probably not the place for me for much longer.

I started to interview and look around. At one point, I had an interview with a nearby firm that had some connections and the word got back somehow to the firm I was working at and that kind of blew up and the results are so weird. Confrontations about conversations people weren't even supposed to have known about because they were within an interview context, and it just was very awkward.

I ended up taking a job at another big firm, which was not my original goal, but I was looking for somewhere that would give me some opportunities. They seemed impressed by what I'd done. They seemed willing to give me opportunities. They had a no-screamers and no-assholes rule so I thought, “I've talked to much people, I've got some experience with this, at this point, I can see that hunted and haunted look in associate’s eyes. I don't see too much of it here. Okay.” So I went and joined another big firm.

Sarah Cottrell: Just to go back to the whole interviewing with the other firm experience, it was definitely one of those classic Biglaw things where when the powers that be realized that you were clearly thinking about moving on and looking for other opportunities, it was like they wanted to convince you not to go but they didn't actually want to do anything in order to do that. It was like what I think of as the classic Biglaw like “We really want to look like we're trying and even though we're probably not really trying.”

Ed Cottrell: Oh, yeah. I had been asked what could make your experience here better and I said, “Well, I'd like to work more IP cases, they wouldn't put me on any IP cases, because even though I have a math background, and I'm a computer programmer by experience, I couldn’t get patent bar admitted. So therefore, they weren't interested in that even though I didn't need to be patent bar admitted for 99% of the work that I would have been working on.” But they wouldn’t do that.

I kept getting random people throw things in my way because they thought I could handle it whether or not it made sense or it was something I wanted to do. I remember walking out of court one day on July 3rd, looking forward to a wonderful 4th of July weekend because I had nothing else on the calendar and it was only two o'clock in the afternoon. I thought, “This is going to be great.”

I got a phone call from a very senior partner asking, “Hey, what are you doing this weekend?” and I hadn't talked to him since I was a summer associate so I was like, “Well, I guess I'm working for you.” There was no interest in accommodating anything commensurate with a life. It just wasn't there.

There was no interest in what I really wanted to do within the firm or what types of cases I wanted, even frankly, in the expertise I’d spent years building up at that point because I was among the most knowledgeable people in the firm at that moment around Texas Trade Secrets Law just because that's what I lived and breathed for 9,000 billable hours or something. There was really no interest in that. It was like, “Okay, let's move on and do this completely disjointed set of things that don't happen to your interest or skills.”

Sarah Cottrell: Yes. Also like, “Here's something that no one else will touch because this person is a screamer. But we know that you are a solid person to handle it.”

Ed Cottrell: Yeah. I got three to four of those in a row.

Sarah Cottrell: I am super excited to let you know that I am bringing back the Guided Track this fall. The Guided Track is a live 10-week small-group intensive for lawyers who want to jumpstart their search for an alternative career. As you know, I have a group program called The Former Lawyer Collaborative which is self-paced that you can join at any time. But the Guided Track is a little different. It builds on the curriculum with The Former Lawyer Collaborative and adds on to it this experience of a small group that you meet with, with me for 10 weeks, where you can get weekly coaching as you move through The Former Lawyer Collaborative which is the curriculum that forms the backbone of both the Collab and the work that I do with all of my clients, including my one-on-one clients.

The next session of the Guided Track is going to be kicking off this fall. The orientation call is going to be on September 13th, and then it's going to run through November 22nd. Tuesday evenings at 8:00 PM, Eastern. There are nine spots available. This is a small-group experience where you're going to be able to get a lot of personal feedback from me. That's why I capped the number of people who can enroll.

What is involved in the Guided Track? You have a week-by-week Guided Track action plan, which is designed to take you through the framework in 10 weeks. We'll have weekly coaching calls. Typically, they're about an hour and a half, starting at 8:00 PM on Tuesdays where we can check in on your progress that week, the questions that have come up, the issues that are arising.

Also, as part of the Guided Track, I will be bringing in a GALLUP Certified Strengths Coach to run a half-day virtual interactive workshop. You will get a free Clifton Strengths Assessment and 34 Report. You will also get custom analytics that elaborate on how your talents drive your motivation. Plus, we'll be doing some hands-on exercises for gaining additional insight into how your strengths relate to your potential career path. That's included when you join the Guided Track.

In addition to that, included in your enrollment in the Guided Track is also membership in The Former Lawyer Collaborative so that you are supported beyond the 10 weeks of the Guided Track. When you enroll in the Guided Track, you get access to the Collaborative immediately.

If you've thought about working with me, you want more support than what you get in the self-paced collaborative but you're not quite wanting to do a full-blown one-on-one coaching package, this is a perfect opportunity for you. Again, there are nine spots available. Go to I am really excited to kick this off in a couple of weeks. If you have any questions, always feel free to reach out. You can email me at [email protected]. Back to the episode.

Sarah Cottrell: Talk to me about the next firm that you went to and sort of what happened there.

Ed Cottrell: Yeah. The next firm, it felt at first like going from 100 miles an hour to about 70, which was nice. I was working with good, really nice people that I actually genuinely liked and still like to this day. I was working on interesting stuff. I was given the opportunity to plaintiff depos in some pretty big cases. I was given the opportunity to basically devise a strategy for, draft and submit, file a summary judgment motion and a nine-figure case that we won and that basically took the door on that the whole way.

I got a lot of great, great opportunities for nine months. Then a particular partner who had a practice I was not at all interested in called me down to his office on a Wednesday afternoon around 4:45 and asked if I had a few minutes, which turned into more than 900 billable hours in three months.

This was a guy who would call you at two in the morning and I got phone calls that consisted of nothing but F bombs and the word mother. I got phone calls that would tell me that I was utterly incompetent and I shouldn't be thinking of X,Y, and Z, doing all these things, followed literally two minutes later by a phone call from the same guy telling me “I'm so glad that you were on top of X,Y, and Z and I don't know how we'd be doing this without you.”

It was just completely insane, and I mean that literally, it was an insane work environment that was just intolerable because I was getting home at three in the morning and being back at the office at seven. I was worried I was going to drive my truck off a bridge at that point because I just wasn't sleeping and did the same kind of thing, tried to talk to the firm and said, “Hey, this is a little bit nuts. I'm working around the clock.”

This partner doesn't believe in delegation except to one person who then is not allowed to delegate further and so I'm shouldering the burden for all of the filings, all of the hearings, and everything that needs to be done for this case, and I can't do it on my own. It's not a one-person case. They got, “Well, why don't you see how this case goes and then we'll talk about reassigning once it's over?”

I knew from experience, these cases lasted 5 to 10 years. Sadly, that's the norm and this one ended up being about that. So I got no accommodations. I said, “Okay, well, I'm going to quit,” and they're like, “Well, we don't want you to do that. Why don't you just hold on?” I'm like, “But I'm going to quit unless you change something.” So yeah, I found a job where, conveniently, you worked.

Sarah Cottrell: This is the part of the story where we tell people we don't try to work together. It just kind of happens that way. We started at the same firm that was not really intentional. It just happened and then this next part of the story as well, but I want to go back really quickly just to the experience with this particular partner because I know I've shared on the podcast before that I wasn't diagnosed with generalized anxiety until after I left Biglaw.

The thing that actually originally made me realize I should see a therapist was actually when Ed was going through this experience, because it was so awful, this person was so terrible to him. But my anxiety about the situation was disproportionate. I was more stressed out about it than you were and you were definitely stressed.

Sometimes people ask me, “How do I know or what do I go and talk to a therapist about?” For me, the thing that originally got me into therapy was I was like, “This thing is happening and it sucks, but the way I feel about it is just over the top anxiety and that feels like that shouldn't be happening.”

The other thing I was going to mention is that we did not have kids at this time. We had decided, for sure, we didn't want to have kids when we were both in Biglaw. Then I left Biglaw, went to the legal publishing company, and then took a job at the Court of Appeals in Houston. But then at that point, once I was at the Court of Appeals, Ed was at the new firm, and then this whole situation was happening. I don't know how you would describe it, but I felt like there's no way we can bring a kid into this mix.

Ed Cottrell: Yeah. It was completely unlivable. I won't say I was worried about my safety around this person. That would be a bit of a stretch, but it was the most bizarre form of gaslighting, straight-up abuse, alternate reality. I don't know what I experienced at that point in my life because it makes you feel like you'd lost your mind.

I talked a minute ago about this two to three phone calls. There was one morning in particular where I got five interactions like that in about a 15-minute period. I think three of them were phone calls, two of them emails, something like that, but it was the same person. It was like, “Hey, why haven't you filed this thing? You need to have a draft of this on my desk by two o'clock today or you're fired.”

Ten minutes later, or two minutes later, whatever, like, “Hey, are you working on XYZ?” I'm like, “You literally just asked me. You told me I had to do it by the day, so yes.” He's like, “Can we do it by Thursday?” “Okay.” Then a minute later like, “Why are we still thinking about this? Why haven't you already done this? I shouldn’t have to tell you these things. You're incompetent,” and just screaming at me. Then it would end up with a phone call like, “Hey, I'm so glad you're the one doing this because I trust you. Next week's fine.” It was insane.

I felt like I had lost my mind. But I also felt like I was in this place where I have to get through this little piece of it because there were various factors around that particular case that made it feel like I just couldn't leave at that moment without jeopardizing my own career. By that I mean, I couldn't ethically find a way to just walk out right then so I needed to get through the end of it. I think that helped me to focus on what is the end goal here.

In my mind, the end goal was to get through this one hearing, and be done. Don't come back to work after that was really my intent. That made it possible for me to heads down just get through it. But you didn't have that advantage so I think it was just all of my, and of course, I didn't have time to talk to anybody else because nobody else wants to talk to me at four in the morning so you got all of my angst, frustration, and exhaustion, which I'm sorry, but it also really highlighted how completely unlivable that was for us. It was just not sustainable at all.

Sarah Cottrell: I think this is the important thing that I think people need to hear because I know there are people out there in similar situations like the one that you're in, it's like everyone at the firm knew, it wasn't like, “Oh, this is happening and you're just suffering in silence. This has never happened to anyone before you with this person or whatever.”

These experiences that we have had, and that other people I know have had, these are what inform the way that I talk about, think about, share about the dynamics in Biglaw firms because I have seen so many similar situations like yes, this was a particular situation with you, but we've seen so many that are exactly the same and it's not like, “Oh, people don't know.”

People know that the person has a large book of business and it's like, “Well, we're just not willing to jeopardize that so we'll just keep throwing associate fodder to this person because that's just a series of necessary casualties in support of the ultimate goal, which is making money.”

Ed Cottrell: Everybody knew. Again, I made sure that there were no screamers in this particular office because it was a smaller office and so it seemed plausible. But a few people straight up lied to me. A few people explicitly said, “We don't have anybody here who is abusive.” Most people, I mean, they lied. But everybody knew.

This guy, I was right next to a corner office partner and he was diagonally opposite from that one so I could hear him coming from his office on the other side of the building. The moment he walked out of his office door, he was walking down the hall, yelling at people along the way. He would walk by and yell at some associate about something, yell at equity partners about things. He yelled at everybody.

He yelled at the managing partner in the office, and he would just tell people how incompetent they were and whatever. But I knew he was coming because I had about 20 people he had to yell at on the way to me. Everyone knew. He burned through an associate every six months before I got there. So it wasn't like this was news to anybody.

Sarah Cottrell: Yeah. We're not saying every single partner at every firm is like this, but this is why when people are like, “Oh, but aren't you exaggerating about how bad it can be?” I'm like, “No. There are many lawyers having experiences like this right now.” It's being normalized and they're basically being told, “Well, this is just what you put up with in order to work at this illustrious place.”

Ed Cottrell: Yeah. You put up with being in a conference room at 5:00 AM that yelled out like, “You need to find the guide to the English language that will tell you how to format these headings.” I’m like, “What guide to the English language?” “Well, there's a book in the library called The Guide to the English Language.” “That is not a book.” “Yes, it is. You go look it up. You're incompetent, you don’t know how to write.”

Fortunately, I knew that was the day I was giving my notice. But that's normalized, that kind of nonsense where it's like, “I'm going to tell you that you're an idiot, despite the fact that you've gone to law school, passed the bar, and probably know more about my case in the moment than I do. But I’m going to tell you that you have no idea what you're doing.” We tell ourselves that’s just paying our dues or something.

Sarah Cottrell: Yeah. It was terrible so we made a plan for you to get out. Can you talk a bit about that?

Ed Cottrell: Yeah. I was not at the point where I just said “I can't be a lawyer at all.” But I was at the point where I said, “I cannot practice like this. I don't have the emotional or mental energy to practice in a traditional role, or to go look for some boutique that's a great fit for me or something.” At that moment, I needed something calmer and I wanted to just use my skills, not all of them even necessarily, but use some skills and experience I had, but in a way that was constructive and not exhausting.

I worked at the Court of Appeals with you for about three years. There was a little hiatus in there where I did an entrepreneurial thing that we can talk about in a minute, but for about three years, I was working with at first several judges and then one of the judges, helping to pull together opinions and think about how cases should be considered, what the issues might be. They've came up with a briefing or whatever, you're digging down to see like, “Is this a fair representation on the record?” all that kind of stuff, and just working with the judges to help them decide the cases at the Court of Appeals.

Sarah Cottrell: Tell everyone what the process was in terms of, you mentioned, taking some time off. Can you situate that in terms of when our oldest was born and then how things progressed?

Ed Cottrell: Yeah. I've been at the court for about two years when our oldest was born, almost. We had some leave we could take but it was basically burning through your vacation time and so on. I took what I could, but we knew it'd be great if we could have a parent at home with our oldest while she was really little.

We did have good childcare, but it was a question of “What do we do to really enjoy this period?” At the same time, you know, Sarah, for years, I had ongoing relationships with some of the people, I had done some software development, web development for years earlier so there was a little project that came out of that where existing piece of software I had, I had rewritten and rebuilt and I thought, “I want to see if this can actually be marketed in a more scalable kind of way. So I'm going to take some time to do that.”

We had just moved because we wanted to change where we lived and so on, once we started having kids, we're having kids, we just moved so we had a little bit of proceeds from that sale, and we said, “Okay, we got a little runway here. I can see if this idea has legs. Worst case, I guess I'll stay home with our daughters and we can survive. Best case, maybe it takes off and it does something.” That's what we did for about seven months.

Sarah Cottrell: Then what happened?

Ed Cottrell: I actually went back to the court because my idea had not gotten the legs I'd hoped it would for various reasons, and spent a little while on the court and realized that this is actually challenging to do what we want to do with two government salaries. I had about three years at this point to recover from my awful Biglaw experience or the second one anyway, and it was a question of like, “What are our priorities?”

We knew we wanted to pay off student loans. That was important to us. We prioritized that over savings because we just really wanted to be free of that forced payment or set of payments every month, which when we started with two, two law degrees was larger than any mortgage we've ever had. It was a lot so we were ready to retire that and that was just not going to happen on two government lawyer salaries anytime soon.

I started looking around and happens to hear from someone at the court actually about a possibility to go work at a big firm but not in a traditional lawyer-type role, in a role where I would be mostly working on a software project and bringing some of my software development and project management and also actual lawyering skills all into the mix to build out some in-house software that the firm had developed. So I did that.

Sarah Cottrell: Okay. That is the first half of my conversation with Ed Cottrell. Tune in next week for the second half of our conversation, and I will 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.