Life After Biglaw in a new Hybrid Role with Ed Cottrell [TFLP151]

This week, we’re sharing the second part of Sarah’s conversation with her husband and former lawyer, Ed Cottrell to talk about life after Biglaw and his new hybrid role. 

Last week, Ed and Sarah talked about the beginning of his journey into law and some of the events earlier in his legal career. This week, you’ll read about the later half of Ed’s legal career, when he left, and where he is now. 

They also talked about what Ed has seen and experienced being a part of the whole Former Lawyer journey. So, let’s get to the second part of how Ed Cotrell left a “fine” legal career for a much better and actually enjoyable hybrid role. 

Concerns About Going Back To Biglaw

Ed’s new role seemed perfect for his non-legal and legal skills. But, Sarah and Ed were both apprehensive about him going back to Biglaw. Ed was concerned about whether his employer would understand what he was doing all day or the urgency (or lack thereof) of the results he was working towards. 

He also had concerns around certain personalities that he’d heard about the Biglaw machine just staffing him where they wanted, not where he was most useful. Ed had a “let’s see” approach, but it was worth a shot. If it didn’t work out, there were always other options. 

He knew a traditional legal career wouldn’t be appealing for much longer. He still enjoyed pro-bono work, even if it included some of his most stressful cases.

Setting Boundaries

Ed was trying to avoid traditional practice. In fact, he was encouraged to do so during his interviews. That was why he considered this legal hybrid role in the first place. He wasn’t interested until he learned more about the job. It didn’t seem like he’d be much of a lawyer, even if the title featured “attorney.” 

Just a few weeks into his new role, Ed’s new employers asked him to go to Scandinavia for an undetermined amount of time to do some due diligence. They never considered that he had never done that before and had a toddler at home.  

He turned it down, setting that boundary even if it put him in hot water for a while. But the next few years were calm, and Ed did as he expected when he started. 

When Fine Isn’t Good Enough Anymore

It was fine for a while. But, around the two-and-a-half-year mark, for various reasons, it became very clear that the partners Ed was working for didn’t get the vision of what they were working on anymore. Also, things were beginning to change around the firm. There were expectation changes. 

Ed’s role became much more of a traditional legal role, which was the opposite of what he wanted. It came to the point where he thought about quitting. However, events conspired to keep him there for a while. The plan was to relocate to Philly and work from the firm’s office there, flying back out when he needed to. When the pandemic hit, Ed was just thankful that he had a job that he could do remotely. 

So, he decided to stick with “fine” for a little longer. His legal career had stabilized a bit, but the unrealistic expectations of his employers didn’t. Ed’s employers expected him to make things happen without being able to work on them. 

Again, working in Biglaw became unlivable for Ed, and it became clear that Ed’s employers didn’t (and wouldn’t) see his role as they had described it. And they weren’t willing to make any adjustments to their expectations either. That’s when Ed decided that fine wasn’t good enough anymore. He was getting off this train. 

Life After Biglaw and a New Hybrid Role

Around a year and a half ago, Sarah interviewed a couple of people in the contract lifecycle management space. Through her conversations with these people, Ed got to know the industry and his future employer and decided this would be something he could do. 

After all, contracts were what started his legal journey in the first place. And the technical aspects interested him. He heard about a hybrid role with his current employer, and how they described it sounded perfect, so he applied. As soon as he got the job, Ed gave the Biglaw firm his notice and wrapped up his practice.

Life after Biglaw didn’t bring Ed instantaneous joy. He described it as progressive loads falling off his shoulders. At first, he didn’t realize he felt that way. He was numb. But after every passing hour, he breathed a little easier. 

When he realized that he never had to deal with Biglaw again, a little excitement sparked inside Ed. For years, he suppressed his abilities and turned off things. His brain was wired to automate and simplify, but he had been told not to do it for so long. 

Finally, a month after leaving the firm, Ed could breathe, he could be himself. After so long, things would be more than “fine.” It would be great!  In his life after Biglaw and his new hybrid role, Ed worked with people he really liked, was given interesting opportunities, and got to use his skills and delve into his own interests. 

This new role, while requiring a legal degree and experience, was more of a business-coach type role with heavy software components. It’s been so fascinating that Ed’s been there ever since. 

Watching Former Lawyer Come To Fruition 

Just as Ed realized that working in Biglaw wasn’t as “fine” as he thought, Sarah was bringing Former Lawyer to fruition. So, Ed got to see everything from a unique behind-the-scenes point of view. 

During their time working in Biglaw, Ed and Sarah watched people experience life after Biglaw (or trying) in so many different ways, but there was no structure for anyone. There was no safety net, no support network. 

Ed said that watching people participate in the Former Lawyer Collaborative has been really inspirational. Those who participate come from different parts of the legal profession, they’ve been practicing for different amounts of time, but they all come together with the same problems. 

Another thing that they both saw was how many different directions people in the Collab go after leaving the law. A legal career gives you so many skills that you can use. There are always opportunities in life after Biglaw. 

The Collaborative and Former Lawyer Podcast have changed lives, and Ed has seen the proof. He’s seen the messages sent and feedback given. And he’s proud to be a part of it. 

Start Your Life After Biglaw So That You’re More Than “Just Fine”

Again, the Former Lawyer has been a catalyst for change in many lives. If you’re interested in finding a “more than fine” post-legal career, you should definitely check out the Guided Track. The Guided Track builds on the curriculum with The Former Lawyer Collaborative and adds to it. 

In this small group, you can get weekly coaching as you move through the curriculum that forms the backbone of the Collab. Inside the Track is an action plan created to take you through the framework in 10 weeks. We’ll have weekly coaching calls at 8:00 PM on Tuesdays, where we can check in on your progress, questions, and any issues.

Sarah is also bringing in a GALLUP Certified Strengths Coach to run a half-day virtual interactive workshop. You’ll get an assessment, custom analytics, and hands-on exercises for gaining additional insight into how your strengths relate to your potential post-legal career path. In addition, you’ll also get membership in The Former Lawyer Collaborative so that you get support beyond the Guided Track. 

If you’ve thought about working with Sarah and want more support than in the self-paced Collaborative, but you don’t want a full-blown one-on-one coaching package, this is a perfect opportunity for you. The Guided Track is kicking off this fall. There are nine spots available. Grab your spot now!

Mentioned In This Article

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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 really excited to share with you this week the second half of my conversation with my husband, Ed Cottrell. Last week, we talked about what made Ed decide to go to law school in the first place and some of the earlier events in his legal career. Today, we're going to talk about more about that and also lots more about some of the observations that we've been able to make with both of us having a perspective on what it's like to work in Biglaw as well as some of his thoughts about Former Lawyer. Without further ado, let's get to the second half of my conversation with Ed.

In a lot of ways, it seemed like a pretty perfect role in terms of matching both your non-legal skills, the things that you did before law school, plus of course your law experience. First of all, let me back up, we were both skeptical about you going back to Biglaw. Can you talk a little bit about that?

Ed Cottrell: Yeah. I should have learned a lesson about all this years and years earlier because I had worked with lawyers on software-type projects and I’d known how that tends to go. But anyway, I had some concerns about whether the person I was working for would really understand what it was I was doing all day, would really understand the immediacy, or lack thereof, of certain types of results that if you want to build out something that does something new, that's not magic button stuff.

I dealt with that before where people want a button that does X and they think it's a question of adding a button and they don't understand the X is where 99.9% of the work goes. I had some concerns around that. I had some concerns around certain personalities that I'd heard a little bit about and I had concerns about just the Biglaw machine that tends to staff foreign bodies without necessarily thinking about who those warm bodies are or what's a better and higher use of them. Does it make sense to shuffle somebody off of this other thing? Instead, it's just like, “We need warm bodies, here you go.”

I had concerns about that for sure but I think I remember that we both had a very “Let's see what happens approach to it” like, this is worth a shot, it's such an unusual sounding opportunity, we gotta at least give it a try. If it works, great. If it doesn't, well, there are other options.

Sarah Cottrell: Yeah. I think at that point, and you can correct me if I'm wrong, but at that point, you, for different reasons than me, had come to a similar point of “I don't think I want to be a practicing lawyer forever.”

Ed Cottrell: Yeah. Pretty much. I knew that certainly not a traditional for-profit type practice was going to be appealing to me for much longer. I still enjoyed pro-bono type stuff even though those have been some of the most stressful cases I've ever done and that's still true.

I still enjoyed some of that but I was definitely done with the “There are nine, ten, whatever figure is on the line and we've got a filing deadline of 5:00 PM because the judge freaked out even though it's only 3:30 PM and we've been given 90 minutes to file a seven-page document that we have to draft from scratch.” I was over that. I was done.

I was very much intending to avoid a traditional practice. The particular role I was going to be working in was associated with a docket that was not as traditional anyway where there weren't the same kinds of scrambles and things to move at a more predictable pace. That gave me some hope but I was definitely not interested in getting back into the legal side of things.

I was actually encouraged when I interviewed, I was asked, “Do you want to be on a partner-track role or how do you envision this playing out?” I said, “I don't want to be on a partner-track role.” I was really blunt about that. The response was, “Great. Because that actually makes it easier. We don't really envision you doing this. What do you think about depos and stuff? Are you wanting to come get like 200 depos a year?”

I was like, “I don't know if I can help it. I really don't want to do that.” I was told, “Good, good, good. We don't feel like that's the best use of what you're bringing to the table and why we're interested in you. We don't really want to have you do that.” That was part of why I was wanting to consider this. I was absolutely not interested in the Biglaw job until I heard about this particular role that didn't really sound like I'd be much of a lawyer even though I'd have attorney in my title.

Sarah Cottrell: Tell me what happened next.

Ed Cottrell: I got there and first of all, the partner who'd hired me, I swear I don't know if he remembered why he hired me, but about two and a half three weeks later, I was asked to go do due diligence in some warehouse in Scandinavia for some open-ended amount of time. At this point, we had a toddler and I was being told to go do due diligence, which is literally I've never done before in my life and still have never done.

They were like, “We need somebody relatively senior to go do this due diligence project.” I was like, “Why did you find me?” I turned that down. I said, “I don't want to do that,” which I think nearly got me fired but I was willing to risk it even knowing that was a possibility because I was like, “If that's what they want me to do, then I guess this was going to be my shortest job ever.” Because no way. This was in the dead of winter too so I really didn't want to go free somewhere to do something I didn't know how to do anyway.

But the next couple of years were actually pretty calm and I actually was doing a lot of the kind of stuff that I thought I'd been hired to do, not perfectly but it wasn't radically different from how I'd envisioned it for about two and a half years. It was okay for a while. Around that two and a half year mark, for various reasons, it became very clear that the partners, through whom I reported, didn't really get the vision of what we were working on anymore or maybe at all and so things started to change.

There were some expectation changes including some that were retroactive that completely contradicted what I and others had been told to do with our time and how we managed some things internally. It was like, “Well, you should never have been doing that,” even though we were doing what we were told to do. My role started to become much, much more traditional. I started to do a lot more depos than I'd been doing.

I've been pinch hitting here and there like somebody's out or something, I would cover a depo or something. I'd pick up like 25 a year or something, they were one-day deal so it was like 10% of my time. But I started to do depos every week and it started to be half my time at times and started to be all week sometimes. It started to mean I couldn't really take on any of these other things I've been hired for.

Before you know it, I'm starting to work on expert witnesses, summary judgment motions, and all the standard stuff for these massive multi-state 100-case, 1000-case dockets that I was very much playing a traditional role in. It was like, “Hey, we may have you fly to this state and present this witness or take this witness,” or whatever. It was like, “Nope. Nope.”

Sarah Cottrell: We should also mention that it was a perfect storm because we decided to move from Houston to where we live down in Pennsylvania right around the same time that it became apparent that the person who hired you, who told you that they literally didn't understand what you would be doing but they knew that you understood it and the other person who would be supervising you did, had decided they still didn't know but also wanted to change what you were doing, that was happening and we were moving. It was the summer of 2019, and then 2020 happens and pandemic. There were a lot of moving pieces that created a situation where you couldn't really make a move necessarily.

Ed Cottrell: Yeah. We had just signed with a realtor to list our house. It wasn't listed yet but we just signed with a realtor to list our house in Houston to move up here and a whole bunch of things changed really fast in just a couple days at my job to the point that I started to really question, “Do I want this job? Do I need to quit it?” Maybe even quit it without having something lined up, except that wasn't really an option because we're selling our house and we got to move somewhere. We got all these things in motion now that we got to figure out.

Events conspired to keep me in place because for clarity, I was staying at the same firm even after the move, it had offices in Houston and in Philly so it made sense to do it that way, or it had made sense. But yeah, things conspired to keep me in the same spot and then once we got up here and just started to get settled, the pandemic hit and it was like, “Well, thank goodness, I at least have a job and I can do it remotely. What I'm doing is actually, at this moment, not that interesting really but it's actually very, very helpful in light of the pandemic and keeping the wheels on at certain places, so okay.”

It was fine for a little while longer, it stabilized a bit but every time the thing I had been hired to do came up, it got ratcheted back further and further to the point that I was being asked to make certain things happen without working on the things that made those things happen. I was being asked to produce certain reports or produce certain information but not do any of the things that made that possible without 500 hours of work each month as opposed to a couple hours of work.

It became completely untenable and it became very clear to me that the people with whom I needed to work were never going to see my role the way they had themselves described it or the way I described it, or the way I wanted it to be, nor were they willing or interested to accommodate that in any way and adjust their expectations at all.

It was very much a “We don't like what we hired you to do. We don't think that's a good use of your time. You shouldn't have been doing it for the last five years even though that's what we told you to do. Now you're going to do something else.” That something else is potentially fly all over the country and deal with a series of cases that was going to have something like, I think it was a combined 53 weeks of trial in 8 months or something like that.

I was working on pieces of all of them so I was potentially going to be flying from state to state even though they promised that wasn't going to happen. They started saying, “Well, maybe that'll happen, but not much, maybe it'll happen but only a couple times.” I was like, “Nope. I know where this train goes. I'm getting off.”

Sarah Cottrell: Oh, Biglaw. Tell me what happened next.

Ed Cottrell: A year and a half ago I guess, you had interviewed a couple people in the contract lifecycle management space. One of whom now works where I work. One of whom did work where I work, although she's recently left us, we're all very sad. But I knew of that space and of my current employer through the conversations you were having and I thought, “Contract lifecycle management actually sounds like something that would interest me,” because I'm weird.

Contracts were what got me into the law in the first place, those issues got me into the law. At the same time, I'm a nerd, I like playing with computers, I like messing with things to analyze and pick apart text, I like messing with things to generate text. This is how I roll.

I heard about an opportunity at my current employer that was to bring in, ideally you’d be somebody who is bringing legal experience as in working at a law firm or actually having a JD in having practiced and ideally you'd be somebody who knew how to code or was open to learning how to code, and ideally you'd be somebody who'd managed projects before, etc. There was this list of things I looked at and I was like, “I think this is me.”

So I applied and through a series of interviews and all that stuff, I ended up getting a job. I had to hesitate for approximately as long as it took me to type the email to tell my firm that I was out and that was the last time I practiced. I gave them two weeks to wrap up my practice and be responsible.

I went to the office for the first time in two years because of the pandemic and was like, “Wow, I did not realize I had so many paper files still floating around here in 2022,” but had to clean all that stuff up and I quit. I was out, got a new job, went inactive in both the states were I’m barred and here I am.

Sarah Cottrell: Okay. Let's just talk briefly, I want to talk a little bit about my perspective. A big part of why you took this hybrid role that you just talked about leaving was because it specifically was presented to you as this is something where you will be using a lot of your software development coding, etc. skills.

It's definitely true that the lawyer whom you worked with most closely, who had the most knowledge about the actual technology that you were working on, understood that you had those skills and appreciated them and gave you as many opportunities to use those skills as you could. That's my impression.

But the problem was that pretty much every other more senior lawyer, it appeared, did not have the capacity to even know what it was that someone—and not just you, also others—with technical expertise, something that was not legal, to even see what they were bringing to the table.

Ed Cottrell: Yeah. It's the problem that you run across in all different industries. I don't think this is unique to law but I think there's a particular problem with it in the law. Lawyers, especially litigators, want to take a fact, ideally put it in some context but then take that fact and use it in some way.

You want to put it in a letter to the client or a letter to an insurer, or filing with a court or a closing argument, or whatever it is, and there's not always a lot of appreciation for where those facts come from because so often, I think as a litigator, you're looking at some spreadsheet or some report that some company had put together in 2015 and is now the subject of some litigation.

You find the magic number in there, 1,230 and you think, “Okay, that goes in my brief,” and there's a blindness to the effort that went into collecting the 1,230 whatevers and reporting on it. I would get these requests like, “Can we do the following thing? Can we provide this report, pull these numbers, add this analysis, or whatever it is we're doing, can you tell me whatever pieces of information I need to know by noon?”

I'd be sitting there thinking, “Well, I can because of what I've done over the last two months but if you'd asked me two months ago, the answer would be no, and if you ask anybody else two months ago or even today, the answer would be no because I've been building this tooling that allows us to do this.”

Then I'd get complaints about why did it take you 15 minutes? I'm like, “You don't understand. It should have taken me 200 hours but I could do it in 15 minutes the morning you asked me for it because I'd spent all this time preparing to do that because piece by piece, these things were starting to come into view and you asked me for this so I built a tool to do that. You asked me for this, I built a tool to do that,” and now every month I can generate X in 20 minutes as opposed to hours and hours and hours of number crunching.

That was one of the more frustrating pieces for sure because there was just a total blindness to what we were doing. There was also this impression that we were blind to the economics of the group that we worked with even though in reality, 90% of what we were doing was focused on saving time and saving money.

I knew very much that I was not billing out in a traditional way for most of my hours, at least at first, and so I knew that I was a call center. But I also could look at what I had done and could present coherently what I had done as “This is why we were able to do this. This is why we were able to sell this client on this idea or the service. This is why we were able to produce this report. This is why we were able to answer when the insurers wanted to know XYZ.”

I was able to present myself as a cost saver where I was saving the practice significantly more than it was costing. But it wasn't understood that way because “Well, why would we need all that? You just need to give me the number” without any understanding of “That's literally what I spent my whole job doing is making that number a thing.”

Sarah Cottrell: Wait, are you telling me that there's a decision maker in Biglaw who's bad at long-range planning?

Ed Cottrell: I am in fact saying that.

Sarah Cottrell: I'm shocked. This is shocking news.

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 how you felt when you were able to leave that job.

Ed Cottrell: Honestly, I felt numb for days. It was this weird like elated but only very briefly. Then it was not even like a constant joy at first. I described it as progressively taking off different loads. I didn't even realize I felt this way at first, but I felt, when I gave my notice, like I had been living underneath a Volkswagen, not like in the space under a Volkswagen, like someone dropped one on my head that had another Volkswagen on top of it, that had a bus on top of it and a train on top of that and maybe a plane or two crashed into it, and a building sitting on top of all that.

It felt every passing hour after I gave my notice like a little bit of that rubble got pulled off and I felt like I could breathe just a little bit more and get just a little bit more oxygen into my system. It would be sparked with little moments of joy where I'd think, “Oh goodness, I don't have to deal with X or do Y or whatever ever again.”

But it took a solid four weeks or so, longer than I had between jobs. I was into this to the next job before I could really feel this but it took a while to be like, “Oh, thank goodness, I feel like I'm myself again. I feel like I have been bottled up and suppressing how I want to interact with the world and what my personality is even like. I've been suppressing my abilities. I've been having to turn off certain things.”

Because I had learned from my experience that if I could automate and save something, save some time, save some money, etc. on something but I hadn't explicitly been told to do it, well, you can't do it, it's going to come back and bite you. Somebody's going to want to know why you did that.

Even if you don't bill for it, even if it's faster to do it than it is to do the email you're writing right now, like I can automate this email in the future in two minutes or I can write it in five, even in those scenarios, it wasn't something I could do. That's just completely inimical to who I am. I'm wired to find automation something. That's just how my brain works. It took a month really before I felt fully like I could breathe again, fully like I could be myself, fully like I just could honestly enjoy life. It sounds melodramatic but that's really where it was.

Sarah Cottrell: It's interesting, I feel like probably there are some people who are like, “Well, but your wife, she basically just sits around all day talking about how terrible Biglaw is for her job, so maybe that just made you feel this way,” what would you say to those people?

Ed Cottrell: I would say why do you think she thinks Biglaw is terrible? Aside from having spent three years in it, she watched me spend 10 years in it. I didn't leave Biglaw because my wife thinks Biglaw is terrible, I left Biglaw because my experience of Biglaw was terrible. My wife, I say, was the smarter one and figured it out seven years faster than I did.

Even though I was in the law for 13 years and only 10 of those were in Biglaw, I somehow managed to make three different stops in Biglaw before I realized this is not for me at all under any circumstances, no matter what the configuration of titles, hour, expectations, and salaries and so on. It just didn't work.

Sarah Cottrell: Yeah. I actually think one of the points that you made just a bit ago is something that comes up for so many people, it was certainly true for me, like different skills, but I, observing you, know that there are certain things that are real strengths of yours and I think one of the most difficult things about many Biglaw roles, especially if you are just not a match for that role, if you're not a glutton for punishment, it's like the things that were your strengths, there's no appreciation for anything outside of a very small box of what is perceived as the skills that Biglaw needs, wants, requires, which is mostly like just billing.

Ed Cottrell: Yeah. Even on fixed-fee engagements, which I did a lot of during my last rotation there, even there, there was just not an appreciation for ways that you could do things other than the traditional way of doing things, which is a lawyer sitting by himself/herself in a room with a laptop, printout, or whatever pouring over something, looking for minutia, and trying to figure out if all the I’s are dotted and all that kind of stuff.

There was no appreciation in any of the places I worked really as a lawyer, for “Hey, we could automate this and never have this be a thing again. So rather than having the same sets of eyeballs look at the same phrasing hundreds of times a year, we can just do it once and then nobody ever has to look at it again because we will know that it's correct. There will be no typos in this sentence, full stop.”

There was no appreciation for that, which blew my brain because I just don't know how else to practice or how to think about practicing. I've got enough to worry about in practice with I got all the deadlines and all that stuff without worrying about “Did I transpose a couple of numbers here and make some misrepresentation that way?” I'd much rather just focus on the big stuff.

But yeah, it was completely at odds with who I was and how I understood what I could bring to my clients, and for that matter, what my clients had thanked me for in the past. The kinds of things that got me to where I was and gave me the opportunities I had, including that one big case and working with all those experts and all that stuff, the things that got me there were a certain set of abilities, and the things that got me praised from clients were a certain set of abilities, and those abilities just didn't work for people in the law firms.

They worked fine in terms of actually getting outcomes in cases typically, but it didn't mean anybody I worked with, except for again a very small number of people, saw it or understood that might actually be helpful somehow, which was extremely frustrating.

Sarah Cottrell: Yeah. I would say demoralizing.

Ed Cottrell: Oh absolutely.

Sarah Cottrell: Okay. Tell me a little bit about what it's been like working in this new role, this non-lawyer role.

Ed Cottrell: My current job is great because I work with people I really like as people. I work with people I respect. One of the things I heard, and I know you heard over and over from lawyers, is “If you leave here (insert firm name), you will never work with the same caliber of clients or customers again. You will never work with the same caliber of leaders again. Here, we work with the C-suite people and you're in these meetings with CFOs, and that'll never happen again. You just won't have interesting problems. The interesting problems land at such and such firm and everybody else has the leftovers.”

That's just not true at all. I work with, in some cases, the same companies, certainly the same types of people, certainly the same titles on the same kinds of problems, I'm not advising them in a legal role but I'm working on making their business better and functional, and exactly the kinds of ways I had envisioned doing as a lawyer and sometimes at my best moments got to do as a lawyer, but I don't have to deal with all the garbage.

I get to interact with people, which I enjoy, I get to solve their problems in a real concrete way, not in a “Let's file this motion and see what happens and its grounds for appeal if it doesn't work in four years,” I actually get to really concretely move things forward. I get to bring the project-management type skills that I learned from running large cases and large doc reviews and all that kind of fun stuff, the budget management skills I learned from doing those things and from being in business for myself for a while, I get to take all the stuff I've learned and apply it to a real-world problem for big important entities, some of which people have heard of, most of which honestly.

That makes it a really enjoyable space to work in and I just work with fun interesting people who like to solve problems. About a third of us on my team are former lawyers or at least have a JD. The rest come from consulting backgrounds or banking backgrounds, in some cases, more technical like software development type backgrounds, but it's an interesting mix of people that just get stuff done and is, believe it or not, able to understand the legal side of things.

Even if they don't have a JD, they're able to understand what's at stake in a lot of these contracts. I know that's shocking to some lawyers out there but we're able to do that kind of stuff and actually counsel and coach our customers in helpful ways in terms of how they think about the product and how they think about their contracting process, again, without giving them legal advice but to help them think through “Is this actually what you want to get the business results you want?”

It's almost a business-coach type role with a very heavy software component to it sometimes. It's fascinating and it's fun. I keep track of my time because I do professional services within the company. That's part of what my description is. But not in the billing tenths of an hour sense, morning like we have a certain pool of hours that you've contracted for and we're going to work against that. It's just how many hours did you spend on this customer and ballpark what was it, were you implementing on the phone, what was it?

Sarah Cottrell: I think I would say what I've observed one of the biggest difference is, which I knew would be the case but I feel like it's really pronounced, is that I feel like the things that are your strengths, like one, you're actually allowed to use them and people actually see them as strengths and you get actual encouragement, and people say positive things about your work as opposed to I would say some places, some firms, there's the sense of “Basically, are you just billing but not doing anything?” I don't even know, I don't know how people's brains work but I just feel like your strengths are actually your strengths.

Ed Cottrell: Yeah. It's really a lot of fun when you see a problem that you know how to solve, and not just solve in a one-off way, but solve in a “I will put this to bed for all time” way. You are not only free to do it but appreciated for doing it.

Because the company I work at, so I'm just going to throw it out there, I work at Ironclad, which as I mentioned is contract lifecycle management, it is still a startup and so we are growing and adapting at a very fast pace, the product is constantly evolving and getting better. But there are problems that people will come up with that drive that development, drive that process.

That means by definition that we don't have a solution just yet that meets exactly whatever it is we're trying to get to. When I can come up with an opportunity to fill a gap or find a clever hack that makes something work or just find a way to steer a customer towards something that actually works better for their business that they maybe hadn't considered, that's appreciated.

That scene is doing the job and doing it well and making all of our lives easier and making us a better and better company, which is fantastic as opposed to “Remind me what it is you did for a 1,850 hours last year?” It's nice to actually be able to do the things that I've always enjoyed in a way that uses my skills, uses my experience, and is not seen as me freelancing in some irresponsible way even if it actually is in fact driving the ball down the field.

Sarah Cottrell: Yeah. I think this is more of an organizational health thing and less of something that only happens in law firms but I get this sense that your experience now is the people who are senior to you, they own their stuff as opposed to trying to put the blame on everyone else who's more junior to them when something doesn't go as they would prefer.

Ed Cottrell: Yeah. I think it's the difference too in terms of how you think about a team. People do own their stuff but if your company or your entity has a real “we're a team” mentality and really truly means that like, “Yes, okay, we do need certain people to sign certain documents and that should be the CEO and not whoever's available at the moment,” but if you have a team mentality where everybody can pitch in and everybody can ask everybody for help, I don't have to go through some formal process or something to staff somebody on something, I can just say, “Hey, I know you know something about this, can we get on Zoom for 15 minutes?” that kind of flexibility and so on leads to a culture where everybody owns the problem.

Even if they're expected to spend most of their time on a certain piece of it, we all own sales, we all own product, we all own implementation, we all have a piece of all of this in some way which is very different from the way firms talk about ownership where like, “Oh, we're all a big team,” and all this stuff.

Of course, everybody knows, first of all, only a very small percentage of people actually have a true equity stake that's actual equity in the firm, and secondly, it's not like that at all, it's more like, I nerd out on medieval history sometimes, it's like an ancient or medieval kingdom where ostensibly, you've got a country here but really, you just have a whole bunch of feuding Barons and little occasional dukes or somebody who gets fired up about things that are constantly at war with each other in little tiny wars but yes, they're literally at war, like taking castles from each other and stuff, that is what I've seen play out over and over and over, not just in firms I've worked at but other firms too where “We're all a big team but don't you dare touch my client.”

It's not nearly as constructive or healthy and you miss the opportunity to deliver some really quality solutions sometimes because there's so much fear and so much control just for a better way to put it.

Sarah Cottrell: Yeah, and just a lot more punching down.

Ed Cottrell: Oh, yes, so much punching down.

Sarah Cottrell: Yeah, which like, “Hey, you should go to therapy.” Go to therapy. If you're listening to this and you are a person, but especially if you're a lawyer, especially if you're a Biglaw, especially if you're a partner, you should go to therapy, I am 100% confident in this fact.

That pretty much brings us up to present day with your story but I also think that it would be interesting to hear a little bit about you describe the point where you realize that your most recent Biglaw job was going in a direction that was not going to be a good fit for you, and that was right around the time that I was starting Former Lawyer. I would love to have you share just a little bit about of what you have observed in terms of the experience of me building Former Lawyer while you are in this process of ultimately getting ready to leave, what do you think that people need to know about that?

Ed Cottrell: I think the thing that stands out to me the most is our suspicion from our own experiences in Biglaw, that all Biglaw lawyers could benefit from some serious soul-searching has been borne out again and again and again. I want to caveat that with I think everybody could benefit from serious soul-searching. A lot of people probably have never taken a close look at how they got to where they are and really thought “Did that make sense retrospectively?” I think that's good for everybody and I'm not saying that as a like, “Oh, I had it all together,” we ended up going into careers we did not love.

Sarah Cottrell: Spoiler alert, she did not have it all together.

Ed Cottrell: It's a question of, every now and then, around life's big bends, it's helpful to look back and say, “Was that the right turn? Are we on the highway we want to be on right now? Are we on a highway at all or are we in a ditch? What's going on?” I think we had both noticed as we started out, our cohort of lawyers, people from our graduating class in law school, or the classes immediately adjacent to it, people we started with at the firm or we started right after we did, that kind of thing, we watched so many of them struggle with the realization that they did not want to do what they were doing.

Even if they couldn't put words on it, even if they weren't prepared to say “I don't want to be a lawyer anymore”, we watched a couple people flame out hard and just disappear, they vanished professionally. We watched some people who would tell themselves the lies that you hear of “Oh, it's just this case, it's not usually like this. It's just this motion, it's just this whatever. Oh, it's just because we have this case and that other case going on. It'll be fine after those are gone.” Spoiler alert, it wasn't.

But we watched people go through all the different almost stages of grief trying to talk themselves into it, denial, and all this kind of stuff and then getting into acceptance, in some cases accepting it by saying, “Well, I guess this is how life is. Everybody's miserable. I got to suck it up and do it for another however many decades.” We watched other people who just did something completely different.

But I think we both had this sense pretty early on that there was no structure there for anyone, not only was there no safety net, not only could you not talk about these things publicly around the firm or something because people would be like, “Oh, that person's weak. Don't give them anything because they'll probably be gone in 18 months,” not only were those problems but there was nothing out there other than Google.

I know you and I talked repeatedly about how it was almost confessional, we would be on one of our evening walks or something and be like, “Sarah, I got to tell you, I looked for alternative careers for lawyers again today and I didn't find anything,” and she'd be like, “I did too.” It became almost comedic because we were just doing it all the time.

I think our suspicion has been validated that actually this is a thing because it's been so inspiring to watch people in the Collaborative, which I am a part of and participate in, to watch people from such different parts of the profession come together with the same problems. It doesn't matter if you were in Biglaw for 3 minutes or 30 years, or in private practice for 15 years or a mix of government, nonprofit, and in-house or whatever, it doesn't matter what you did, you hear the same things from people about the inhumanities of the billable hour, the always-on aspects of our culture, the fact that legal organizations of any variety, whether that's in-house, firms, or in the government, whatever, they just don't really select for management skill when they promote people to management positions, you hear the same stories over and over.

It could be everything from actual harassment of some sort, discrimination of some sort to the stupid thing like, “Hey, are you leaving? Oh good. I'm glad I caught you. I don't need this right now but do you think you can get it to me by eight in the morning?” “It's like it's six hours of work so yes, but I guess I'm not sleeping.” That happens in all different types of jobs.

Not all the stories are the same but I was encouraged personally to not think I was nuts or weak by watching people from so many different perspectives telling the same stories. I was realizing, “Oh, it's not me, it's not that I didn't try the right legal job or whatever.” To be clear, I think we both loved our court job. That was a fun job in many ways and really interesting. It just doesn't pay well. But all the same stresses and anxieties are still there even in a job like that that's actually very collegial and very interesting and more laid-back because you're literally holding people's lives in your hands sometimes.

You're not the one making the decision if you're not the judge, true, but you're sitting there trying to analyze evidence that could determine on appeal whether somebody is behind bars for 30 years or walks free. Even if you're working with great people who are nice and the hours are reasonable and so on, that's stressful and you carry those things home with you and you have these cases that replay in your head.

I can still remember, without getting into the details of which cases I worked on obviously, I can still remember some of the more heinous facts and photos and other types of evidence from some truly horrific crimes. I can't get some stupid commercial disputes out of my head either. You've got all this stuff rattling around in there and you carry it with you. These other people's stresses become your stresses. I think that's fundamental to the legal profession.

If you're in a helping profession that's like counseling, if you're a doctor, or many other types of roles, you help people with their problems. You enter into their problems for a moment and you help them figure out what's next. You tell them maybe what's next, you tell them like, “You have X condition, here are your options.” Being a lawyer is one of the very few things out there where you step into their shoes.

No matter how high you build the walls emotionally, you're going to carry some of their emotional burden, you're going to realize this person I'm working with is being slandered, they're being accused of having done X, Y, and Z and I know what they did, I have the receipts to prove it. It's not just that I trust them. I can back this up and they are being slandered. It is hard not to let that get to you.

Or for example, this person I represent is being, like in a pro bono case or something, being threatened with an eviction or being threatened with extradition out of the country or something like this and you know the facts don't back that up, or at least not the way that somebody's saying it. Like, “Okay, whether it's commercial or whatever, maybe my client's not perfect but this argument is crazy.” It's very hard not to internalize that and become bound up with all these things and to feel responsible for it.

No matter how well you did your job, I'm going to feel horrible if this person is sent back to this country where they're in mortal peril. I'm going to feel horrible if this company has to pay out for something they didn't do. That kind of thing, it's a drain.

Hearing from so many people around the profession, “I've carried this burden. I've had this. I've dealt with this type of personality. I've dealt with this discrimination. I've dealt with this just stupidity or awfulness,” whatever it is, I think it's been really encouraging, not only to me but I've also had the privilege of hearing some of the feedback that people have had about it and I'm glad it exists. I wish it existed 10 years ago but that's how I feel about it.

Sarah Cottrell: I think one of the things that's so interesting, and I know you and I have talked about this some, is like we're talking about in many cases, a lot of the people who I work with are in year 5, 10, 15, but a lot of the people I work with are 20 years in and 25 years in and the experience of one, I find that people in that tenure tend to be more likely to be at the point where they're like, “Is it too late for me to make a change?” Then having the experience of realizing that it's not too late and then also relating their experiences and someone who's five years in saying something and someone who's 20 years in being able to say like, “What you are saying right now is how I felt five years in and you are doing the right thing” I think that's just super powerful.

Ed Cottrell: Yeah. It really became, like I said, almost comical how you hear the same things over and over. You know who I'm talking about here, we each worked with somebody who more than once said something like, “I don't know if I want to do this forever. Sometimes I think maybe I just want to open a flower shop.” We're both sitting here thinking like, “Maybe you should open a flower shop. You've been doing this long enough, you can probably afford it. Maybe go do that rather than whatever this misery that we're seeing right here is.”

It really is remarkable how I think most of us know pretty quickly that something's off with this kind of thing. I'm not going to say I knew I didn't want to be a lawyer 10 minutes in, like I said, I actually loved the first couple of years at least despite the hours were awful, but I thought that was mostly a management problem on my part, like managing up better or something. But I actually loved a lot of what I was doing at first and thought it was interesting so I'm not going to say I had it all figured out.

But I knew even before I went to law school that I didn't think practicing in a big firm would be for me for an extended period of time and yet I've spent a decade there. It makes you wonder what was I thinking. But I think all of us have this experience of there have been some realizations along the way, some aha moments, some sun piercing through the clouds type moments where you realize, “Oh, this isn't quite right.”

What we've seen over and over, you and I have seen over and over is it's never too late to latch onto one of those. It may be too late to realistically and sanely say, “Oh, I want to do this other thing that's going to require another 10 years of education.” If you're 35 years into your legal career, that may or may not be the best move for you to do that. But if you are somewhere along the way, most doors are still open. There are a lot more opportunities.

I always joke that people say you can do anything with a law degree, I joke you can do anything with your gas receipt in your pocket as well. You can do a lot of things that the law degree per se does not pertain to.

But the flip side of that is being a lawyer, being someone who has gotten into law school, passed a bar exam (if not several), gotten barred, practiced without getting disbarred, and managed to keep all the different plates spinning, to manage partner expectations and colleague expectations, to delegate responsibilities downward or laterally when needed, and even delegate up, to run a budget, to do all the different things that most lawyers have done by their first three or four years of practice at the latest, you have so many skills that no doors are really, really close to you. It's not too late to do whatever it is.

Both with the podcast and with the Collaborative, I've just loved seeing people branch off in a hundred different directions and do the thing. The thing that they “Maybe I'll talk about this” and then five years later they make the leap and they're like, “Oh, it wasn't that bad.” It's actually quite encouraging to know that most people who make those leaps don't actually just fall straight into the river. It actually works.

Sarah Cottrell: Metaphors. This is the last question that I have for you, which is I'm notoriously terrible at self-promotion, so is there anything that you think people should know about me and/or Former Lawyer, and by that I mean me with respect to Former Lawyer, that I don't talk about enough?

Ed Cottrell: I, again, get the privilege of seeing some of the behind-the-scenes stuff. I see your own experiences of wrestling with “How do I make this better? How do I know that I'm really serving people? Is what I'm doing a good fit for what people want?” But I also have the experience of knowing some of the feedback you get and knowing that on average, once to twice per week, you get an email, a DM, or something out of the blue often from someone you've never even directly worked with telling you that you've changed their life.

Some of the people I know, and some of them are more public and they're posted in the Collaborative or something, or occasionally even out on LinkedIn or something, and so I know exactly what your connection was with those people, but a lot of times it's somebody who's just listened to a few podcast episodes, read something you've written, or was a member of the Collaborative and set it to the side because some big case came up or deal or whatever and then came back to it.

People write you and say, “This changed my life” or “You're the reason I had the courage to do X” or “I never even thought of X, Y, or Z” or “I never realized I needed to take the following steps. I never realized I needed to tell somebody and that was so liberating to tell someone I don't want to be a lawyer forever.” Those kinds of feedback, people won't see them but that's I think the most compelling evidence for why the Collaborative and your coaching process works so well for people is people say things like “This was the best decision I ever made” or “This changed my life” or “I'm only here because of the Collaborative, because of the coaching, or whatever.”

There's no way to really appreciate it until you've done it. I think that, again, being lawyers, we’re just so siloed. You talked about the conveyor belt in law school and all this, you get in this mindset of “This is how it is,” and then when you get in your job, people tell you, “Well, you're not a product manager, you're a lawyer. Lawyers think differently and therefore, you should stick with this because it's what you're good at. You'd be throwing away your education and all this stuff.”

It's so easy to start believing some of that and think, “Well, I would be throwing things away,” which is almost never really true. Yeah, I have thrown away some of my knowledge of The Federal Rules of Civil Procedure and I don't care, I don't need to know about the Texas Rules of Appellate Procedure anymore, that's true, I've thrown away those things but the actual what makes you an interesting, good, competent person, employee, colleague, manager, business owner, whatever, those things are only enhanced by all that experience. There's no loss there.

What the Collaborative offers is a process of figuring out “Who am I? What are those things about me that are so valuable? How did I get here? What do I do with that, the fact that I am here and have these skills? How do I take the next step towards whatever it is want to do, whether it's a floor shop, project management, compliance, or some academic position, whatever it is, how do I get from point A to point B?”

It's a process of removing the barriers one step at a time so you can do the next right thing, figure out what you're doing with your life in a way that points you somewhere you want to be in a deliberative way rather than, “Oops, how did I get here?” way that I think describes so many of us in law.

Sarah Cottrell: Ah. Thank you. Well, Ed Cottrell, you're my favorite person and I really appreciate you sharing your story with me today.

Ed Cottrell: It's great to talk to you, Sarah. Love you.

Sarah Cottrell: 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.