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.

I'm delighted to bring you another conversation with one of my clients on the podcast this week. This conversation is with Read. He is a member of the Collab. We talk about how he decided that the Collab was the right fit for him and some of his experiences in the Collab and then just overall his experience of becoming a lawyer and then realizing that he did not actually want to be a practicing lawyer. Without further ado, let's get to my conversation with Read.

Hey, Read, welcome to The Former Lawyer Podcast.

Read: Hi. Thank you.

Sarah Cottrell: I am excited to hear your story but let's start with you introducing yourself to the listeners.

Read: My name is Read. I live in New York City. I've been out of law school for I guess two and a half years basically. I've been a member of the Collab for several months now, I'm not sure exactly how long.

Sarah Cottrell: Time flies when you're having fun obviously. Okay, so we're going to start where we start typically on the podcast in general and then we'll get to where our stories intersect. Why don't you start by just telling the listeners what made you decide to go to law school?

Read: Yeah. I think I was the typical cliche of a person with a liberal arts undergrad degree who was unsure what to do. After college, I had a job at a nonprofit in New Orleans which is where I grew up and I think I had an assumption that I would get some kind of graduate degree just because school had always been my thing.

Like a lot of people with my academic background, I was a history major and a Spanish minor, I think I thought that law school would be a good fit for my skill set because it was very research and writing-oriented and involved thinking about social issues and I thought those aspects would be interesting.

When I was applying to law schools, I was just trying that out as an option to see how I felt about it throughout the process and then I ended up getting a bunch of scholarship options. I felt like even though I was unsure about actually practicing law in the future, it was going to be a good deal for me and the stakes were relatively low because I was just interested to learn what law school had to offer and I had those scholarship options.

Sarah Cottrell: Okay. Tell me when you got to law school, what did you think of it?

Read: I actually would say I enjoyed law school overall. There are definitely some classes that I found drier, mainly like contracts and more businessy type things in tax, things like that. But i really enjoyed topics like torts or criminal law that were more focused on a juicy story that happened to someone and how they might get justice for that I guess.

I definitely found the academic experience of law school to be overall positive although also obviously, it was extremely draining at times with finals, all the reading, and all of the exhausting things that go into it. But I would say that my time in law school actually, I questioned whether I was on the right path a lot less than I did after I actually started working in the law just because I enjoyed being a student, which had always been what I was used to up until that point.

Sarah Cottrell: Yeah. I think that's a common experience for those of us who went to law school because we had some liberal arts undergrad major and weren't exactly sure what to do and had always been good at school. Often, the law school experience feels like more of the same like, “Okay, yeah, this is what I'm familiar with,” and then we start practicing, and for, at least, some of us it's like, “Okay, maybe this is not the thing.” Tell me how did you decide what you’re going to do after you graduated?

Read: I was really interested in the idea of a judicial clerkship because that was something that was very promoted at my law school. I went to Tulane. I just remember at the beginning of 1L year, there was a session or something about the benefit of doing clerkship.

I paid close attention to that because I thought a clerkship would be great for me since it was very research and writing-focused which were some of the things that drew me to law school, like I said, and also just the opportunity to build connections with the judge, get to see a variety of different types of cases, and things like that.

I applied for a bunch of clerkships in my 2L year, I guess, and ended up getting one with a district judge, which was a good experience. That was how I got my start actually working in the law.

Sarah Cottrell: Yeah. It's interesting, especially for those of us who went to law school because we like research and writing. If you end up going onto a clerkship post law school, in a lot of ways, it can extend that, “Okay, this feels like a good fit or at least a decent fit because research and writing and I like that and that's part of why I went to law school.” Okay, tell me what happened next.

Read: During my district court clerkship my first year out of law school, I think I started to pick up on the fact that actually practicing law at a law firm specifically probably wasn't going to be right for me. I encountered lawyers in private practice through everything I was doing as a law clerk, having status conferences, trials with them, and all that and just writing memos on the types of motions they were bringing to the court and I just couldn't really see myself doing what they did.

Hearing about all the discovery disputes they had and just the nitty-gritty of litigation, I definitely started to realize that it was not very appealing to me. For my next job, I really wanted to just keep working in the courts because I had enjoyed my clerkship and as a way to postpone actually being in private practice or any type of active legal practice.

I got another job as a staff attorney at a federal court of appeals which is also very research and writing-focused. That started off pretty well. I felt very comfortable with the tasks I was doing since I was mainly just writing memos and researching the facts of the cases and a lot of things I got used to doing as a district court clerk.

But then I gradually started to feel frustrated with that job because my district court clerkship had been a lot more varied in what I did every day because we would have trials or status conferences or even criminal sentencings and actual court proceedings that I would have to brief the judge for and attend and take notes which broke up the day nicely and made me feel like I was interacting with a wider range of people since I was having to talk to the parties often and things like that.

When I was at the court of appeals, the job was mainly focused on just writing memos and reviewing the documents in the record. It felt drier and less varied I would say. That's when I really started feeling frustrated with the law as a whole because I still had that sense that I wasn't that interested in practicing. Even the appellate cases I was now working with, I couldn't imagine myself actually going through all the grind of litigation that it took to get a case to the court of appeals and the minute details that go into filing motions, writing a brief, and all that.

I found myself very grateful that I was on the other side and only responsible for reviewing what the attorneys had to prepare but I couldn't see myself doing what they did. Also, just the fact that I was getting bored with the job when it was the one type of legal job that I thought I would enjoy, I think that's when I got the most disillusioned with being a lawyer as a whole and started to think about branching out into other things.

Sarah Cottrell: Yeah. First of all, I was just having a conversation with someone else for the podcast about the fact that a lot of people who go to law school, in part because they like research and writing, end up going the litigation path because that's the path you go if you're interested in research and writing and how much of litigation is not in fact research and writing, or if it is, to your point, it's wrapped up in a particularly frustrating framework.

I find that a lot of lawyers who chose to become lawyers, in part because of the fact that they are interested in research and writing, being a trial lawyer is actually not a great fit.

Also, you were describing working at the appellate court and being like, “I don't really think I want to be on the flip side, actually the parties doing this,” and I know people who listen to the podcast will know this about me but I took the opposite path where I was a litigator and then ultimately went and worked as a staff attorney at a state appellate court, and one can confirm in my opinion that working at the court is much better than being one of the parties but also, to your point about having the experience of “Hey, I'm basically doing the job that I thought or that I think is going to be the closest to a match for me as a lawyer and it's still not a great fit,” that can be a moment that's very illuminating. But also, for some people, it can create some panic.

Can you tell me what was it like to realize, “Actually, maybe I don't want to be doing this?”

Read: Yeah. It was definitely stressful. I think I went through a period where for a couple of months, I was going back and forth and feeling like my feelings were different every week about whether I still wanted to try to find a niche area of the law that might be fulfilling for me or if I should just move on and make a plan to branch out to other things.

I struggled with that for several months and then I think finally I just have the sense that if I've been dealing with these feelings of dissatisfaction for so long, then it probably means I just need to branch out and do something else.

I also think it helped that I had never been all that enthusiastic about practicing law even when I was preparing to go to law school. I was just viewing it as a way to expand my options and not necessarily committing myself in my mind to a career as a lawyer.

I think I looked back and realized I never actually wanted this all that much so there's no reason I should force myself to stay in this field that I've now been feeling for a while doesn't really fit my personality.

Sarah Cottrell: Yeah. It's interesting because you mentioned part of that calculus was getting scholarships, these scholarships. Many people who are listening will relate to having similar realizations but the challenge for many people comes when they're like, “Oh, I don't actually think this is what I want to be doing but also I've gone into a bunch of debt for this,” which side note, if anyone is listening and they are still thinking about going to law school because I know some people that do listen, the path that Read took with scholarships is yes, okay, do that because it does create a situation where I think you do feel a little bit more flexibility in terms of what you can do next.

It sounds like for you as well, do you think it's fair to say you didn't have that same sense of “Who am I if I'm not a lawyer?” or was there still some of that?

Read: Yeah, totally. Yeah, I'm very grateful for the scholarship I had. I think that definitely removed a lot of the pressure from that period when I was spiraling about whether I really wanted to leave the law. I think that having that freedom of knowing that I hadn't sunk a ton of cost into the whole thing, I would have been a lot more stressed if that had been an element so I'm very grateful for that.

Yeah, I never really fully identified as a lawyer deeply. I think I was willing to try on being a lawyer as a profession but I don't think I'm one of the people who always felt like that was who I was meant to be or that my job defined my whole lifestyle. I think that benefited me being relatively open-minded about moving on to something else.

Sarah Cottrell: Yeah, okay, tell me, you decided, “This is not for me,” or “I'm pretty sure this is not for me,” can you talk a little bit about how you started to go about the process of figuring out what you did want to do and then where the Collab played into all of that?

Read: Yeah, totally. I was very concerned with figuring out exactly what I didn't like about the law and how I could take those insights to find something that would be more fulfilling. I was just reflecting a lot. I think when I joined the Collab, the first things I did were some of the personality tests and values tests that you recommended on there.

I also just started posting open-ended questions in the Collab and just hearing people's responses definitely got my juices flowing and were helpful, a helpful way to find new perspectives on what types of things I should be looking for.

I think my takeaways were that what I didn't like about the law was that it didn't really allow me to use creative thinking and I don't really mean creative in the narrow sense of designing something, writing a story, or whatever although I enjoy doing things like that on my own time but I think in my career, I just really want to be able to find my own way of doing things and have a little bit of wiggle room and my own input into how I accomplish my task.

Because I think in the law, it can be so rigid. You're always operating under a system of established rules and having to follow a certain approach to something usually whether it's literally following the Federal Rules of Civil Procedure or whatever the judge has ordered you to do. In the case your senior partner is telling you to do, there are always some really clear requirements that you have to follow.

I think I was really craving the type of work where I would just be able to figure things out on my own and come up with new ways of doing things. That's what I mean by creative thinking. I think that was my main priority when I was thinking about other types of roles that I might enjoy more.

Sarah Cottrell: Yeah. It's interesting. Creativity or not being able to engage or think creatively in the way they want to is one of the, I'd say top three meta-main reasons that lawyers who I work with mention in terms of why lawyering isn’t a great fit. Like you said, it's not necessarily that people are like, “Because I want to be an artist or because I want to be a writer,” it's more the fact that the law, because of how it is structured, to your point in just how it works, is not necessarily a place where you can engage creatively but the parameters are very fixed.

I think there are a lot of people who go to law school not realizing how important that creativity piece is for them because, for example, they don't think of themselves as an artist or wanting to pursue something that's stereotypically creative but then once they're in their lawyering job, they realize, “Oh, there's this whole aspect of my personality and also my strengths and skills that aren't being used in this lawyer role.”

Read: Yeah. That's very much how I felt.

Sarah Cottrell: I'm curious, you mentioned the different assessments that you took as part of the framework. Was there one in particular that stands out to you as either a result or the entire assessment that you found to be particularly helpful or there was something in it that helped you see something new?

Read: Yeah. I did them all a while ago at this point. I remember the CliftonStrengths being helpful. I think it identified creative thinking and autonomy as things that were important to me. I don't remember exactly what the more general personality tests that are on there is but I think that was one of the first ones I did.

That also of helped point out aspects of my personality and skill set that I realized were not being taken advantage of at all in the law like creativity and I guess I said autonomy, being able to make my own contributions in terms of setting my own priorities and strategizing my own way to accomplish something.

But also, I remember it really emphasized that I enjoy being on a team too and doing my own thing while also contributing to a team, which I think is very true. I think that was another thing that I realized wasn't really clicking, at least with the jobs I had had in the law so far because it can feel very individual sometimes, legal work I think because you're assigned a discrete issue to research or write a memo about.

Even if you're part of a team that's working on a case or something, the tasks that you're actually doing are not all that collaborative. I think that was something I was craving too.

Sarah Cottrell: I think that is such an under recognized aspect of why some people don't like legal work because to your point, I'm thinking as a litigator, you're part of for example a trial team and so you don't think of it as being as individualized as it is. But the reality is that yes, there are ways in which you work with other people obviously when you're at a law firm.

But in particular, if you're at a law firm, the overall way that the firm is structured, it's almost hard to describe, especially for someone who hasn't worked in another type of company but because you have partners who are all owners but they're not owners in the normal sense and also they're supervisors but they're not your supervisor in a very structured sense, you end up with this situation where you might work with a lot of people, you might even be part of particular teams but you don't necessarily have that same sense of we're all working towards a common goal, not just in the individual team but in the overall organization in the way that you can and do in other types of companies.

If you're someone who cares a lot about that aspect of things, which many lawyers do actually want to be part of a team, I think that is something that can be hard to recognize because you're being told you're part of a team and so recognizing I am but also not in the way that I'm looking for can be a little bit tricky.

Read: Yeah. Totally.

Sarah Cottrell: Okay. Can we just go back slightly because I'm curious to know when you found the Collab, came across it, or whatever, what was it that you were looking for help with or looking to figure out that you hadn't been able to yet? Does that make sense?

Read: Yeah. I think I was mainly just looking for other people to bounce my ideas off of. I had all these thoughts in my mind about why the law wasn't right for me, what type of thing I should be looking for, and how exactly do you pull off the logistics of leaving the law and entering another field.

I think I was mainly just looking for I wanted to see how it was going for other people who are trying to do the same thing, have somewhere that I could ask questions or even just vent or something, and have other people who would understand where I was coming from.

Sarah Cottrell: Yeah. To your point about everything often feeling so individualized, there's also I think this element for lawyers where if you aren't happy with what you're doing, it can feel very isolating because even if you're in an environment where everyone talks about how much the job sucks, there's a difference between that and being like, “No, really, but I actually I don't want to be doing this anymore.”

Tell me more about your process where you are now and how the Collab has played into that.

Read: Yeah. Ever since I officially decided that I was going to start planning leaving the law, I've definitely still had a lot of different phases of my thinking about what I want to do next. I think I've cycled through a couple of different options of potential careers that I was considering and for a couple weeks, I felt like really interested in each of them and then I ended up finding reasons to question them and going back and forth.

I posted in the Collab a few times about questions I was having about, whether I should look for some kind of bridge job practicing law that would be slightly more interesting than what I've done in the past that would allow me to pay my bills while continuing to figure out what exactly I wanted to do next or whether I should just take the dive into finding something in a completely different field.

That was something that I debated for a while and now I think I've pretty firmly decided that I would rather just go into another field as soon as my current job wraps up rather than do some kind of bridge job and prolong my experience in the law now that I have the knowledge that it doesn't really fit my priorities for my career. It's definitely been a winding process of figuring out what exactly I want. But I do think I have over time become more confident in what exactly I should do next.

Sarah Cottrell: I think that's so important. I've had several conversations just this week with people, it's like the threshold question, it's not even like, “What do I want to do that isn't the law?” it's like, “Do I actually want to do something else or do I just want to try something else legal?” That is a question that most lawyers deal with and struggle with at least for some period for lots of different reasons.

I think even just resolving that question is so helpful because, like you said and you're describing, then you know, “Okay, this is the direction that my thinking and exploration needs to take,” as opposed to ping-ponging. I mean, there's always some ping-ponging, let's be real because that's just part of the process.

What else would you like to share about where you are, your experience in the Collab, or anything else?

Read: Where I am currently is I've started doing informational interviews with people I found who have left the law and gone into fields that I'm interested in, which is a concept that I think I gained from the Collab because it really is so helpful to talk to other people who have been there.

I found that people generally are pretty open to just having a phone call with you and talking about the industry they're currently working in and their process of leaving the law because I think everyone who's done this is pretty eager to help other people going through the same thing.

I finally just recently actually scheduled some phone calls and started talking to people. I just browsed LinkedIn looking for people from my law school who are now doing other things and have just been picking their brains about what they do now.

I've been mainly focused on nonprofit development jobs because that's what I did briefly for a year before law school and I was always interested in the field. I just, at the time, believed that I needed to go to grad school and build some other kind of career for whatever reasons I was thinking back then. But I think I realized that that type of work would be a much better fit for me so that's my focus area right now and those are the types of people that I've been talking to.

I've already found, even in the couple informational interviews that I've had, people in that field especially are very open to just mentioning opportunities they've heard about or sharing resources. I found that to be extremely helpful so far.

Sarah Cottrell: Yeah. It's interesting I think, in part because of how the legal profession often is when I'm working with lawyers and talking with them about reaching out to people, especially doing cold emails or whatnot, there's the sense of “Would anyone really want to talk to me?”

The reality is that in many cases, they do, especially if they're former lawyers. But also no one is excited for the most part when we get to the point where it's like, “Okay, it's time for informational interviews,” but the thing is, and as you said, it truly is one of the fastest ways to get tons of clarity and I've seen it happen so many times where people are like, “Uhh,” and then they start to do it and they're like, “Oh, okay, I actually see what kind of value I'm getting from this.”

Read: Yeah, totally.

Sarah Cottrell: That's just a plug in general for informational interviews and also a recognition that I know that for most of us, it isn't the thing that we would necessarily choose to do otherwise. Okay, anything else?

Read: I think yeah, I would again say I honestly wish I had started doing informational interviews earlier in the process because it really has been clarifying, like you said, to just talk to people who have successfully pulled off this kind of transition. I think it only solidified my feelings that I was on the right path by leaving the law.

I would encourage everyone to do that even if you feel unsure about it still, I think talking to people who have done it will help you figure out what your real feelings are faster.

Sarah Cottrell: Yeah. If you have questions about how to do informational interviews and whatnot and you're not in the Collab, if you are in the Collab, there's a whole lesson about that, some workshopy stuff, and whatnot because, especially when you're doing cold outreach, I recognize that can be like, “What do I even say?” but if you're not in the Collab, come join us in the Collab.

The one other thing I wanted to say that I think is really instructive from the story that you shared is it is not uncommon for lawyers to start to go through this process and to realize that either something they did before law school career-wise or something they did previously in a volunteer role or something like that maybe even that they had thought about going into as a field but ultimately ended up going to law school, it's pretty common that people realize, “Oh, actually, that thing that I decided not to pursue actually is something that is a good fit for me.”

I think that's really important for people to hear because sometimes, it can feel particularly hard to realize that depending on how long you've been practicing law, etc., because it can feel like, “Oh, I was going to do this thing and then I did this other thing,” it magnifies that lawyerly sense of “Oh, it was a mistake.”

I just think it's really important for people to hear that one, that's very common and two, in pretty much every story that I have heard of, you have to go through what you go through to get the clarity that you need.

Read, I think your story is a really clear example of that. Is there anything else that you would like to share either about your experience in the Collab or the process that you're going through now?

Read: Just another thing that I've gained from informational interviews I think is the realization that there are a lot of jobs out there that people are enjoying. I feel like there's a culture in the legal profession of complaining about your work and not liking it but there are a lot of people out there who feel neutral to positive about the work they do every day, which is refreshing to realize.

Sarah Cottrell: I think that's so important because I can't tell you the number of lawyers who have basically either straight up been told, “Well, you don't like your job but that's just how it is for everyone,” or even if they haven't been told that have this sense of “This really isn't a good fit and everyone seems to be unhappy, but isn't this just how it's supposed to be?”

To your point, it's really not like that in all industries, roles, and jobs. It just isn't. We see such a skewed view of it within the legal profession. That is a really helpful thing to remind people of. To your point, informational interviews can help you see that so this is just like a yay informational interviews segment of the podcast.

Read: Yeah, pretty much.

Sarah Cottrell: Okay, cool. Well, Read, I really appreciate you coming on and sharing your story, both your process and also your experience in the Collab. Is there anything else that you would like to say as we wrap this up?

Read: I don't think so. I think I pretty much shared everything.

Sarah Cottrell: Okay, well, thank you so much for joining me and sharing your story. I really appreciate it.

Read: Yeah. Thank 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 formerlawyer.com/first. Until next time, have a great week.