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.

This week I'm sharing my conversation with Dan Lemon. Dan is a lawyer who is also a member of the Collab, and he is someone who joined the Collab and ultimately decided that he still wanted to practice law but in a very different way.

So this is for anyone who's like, "I don't like what I'm doing, but maybe I still want to practice, but I'm not sure." If that's you, then this is going to be a great episode.

I also just want to give a content warning on the front end of the episode. One of the things that we talk about—Dan talks about his experience with suicidality and suicidal ideation—and so that is a significant part of our conversation.

I think it's a really important conversation, but if that is something that would be sensitive or triggering for you, I want to let you know so that you can use your discretion in listening to this episode. With that, let's get to my conversation with Dan.

Hey, Dan. Welcome to The Former Lawyer Podcast.

Dan Lemon: Hey, Sarah. Thanks so much for having me on. Glad to be here.

Sarah Cottrell: I am excited for you to share your story. Let's start where we usually start, which is can you just briefly introduce yourself to the listeners?

Dan Lemon: Sure. My name is Dan Lemon and I'm not a former lawyer—spoiler alert—I still practice law, but I practice law in a very different capacity than I did when I was a practicing lawyer at a Biglaw firm, which I did for eight years.

I just wanted to come on, I remember being in the space that I presume a lot of your listeners are in, where I felt very sort of lost. And it helped me a lot to hear the stories of people who had kind of stood where I had stood and how they sort of navigated the various issues that they navigated as they were trying to leave or trying to figure out what was next for them.

So even though I didn't wind up leaving the law entirely, I did make a big transition, and I thought it might be helpful for someone out there to sort of hear my story and how I wound up where I am.

Sarah Cottrell: Yes, and also for listeners, the reason that I know Dan is that he is in the Collab, which is relevant because often people will ask me, basically, "Does anyone who you've ever worked with not end up leaving the law?" Basically, "Are you like, 'You must leave if you work with me?'"

I say, no. My goal is that people figure out what it is that they actually want to be doing, and that can be anything, including staying in the law, if that's what works for them. So I'm excited for you to tell us more about what that process looked like.

Why don’t we start like we typically start on an episode, which is, do you want to tell us a little bit about why you decided to become a lawyer in the first place?

Dan Lemon: Yeah, I love hearing people's answers to this question because it's such a simple question, and the answer is always like 15 minutes long.

Sarah Cottrell: It's true. "Let me unpack my entire lived experience for you."

Dan Lemon: Exactly. So I was the kid who always wanted to be a lawyer, and question why, answer, I have no idea. I'm sure someone put the idea in my head at some point in time. But yeah, I didn't have any lawyers in my family. I didn't even know really what practicing law was all about aside from obviously what I had seen on television, Law & Order, and Boston Legal when I was growing up.

So yeah, I had kind of always had this idea in my head that I wanted to be a lawyer. I remember when I graduated from high school, we opened up these time capsules that we had made for ourselves in second grade, and I was probably the only second grader who wrote that he wanted to be a lawyer when he grew up.

When I went off to college, interestingly enough, I kind of allowed myself to be talked out of that. I had actually gotten some good advice from various people who said, "Being a lawyer is kind of a hard road. You work a lot. Most lawyers don't make as much money as people think that they do."

So when I was in college, I wound up going and majoring in business administration, which was in retrospect a terrible decision. But that was what I thought at the time was sort of the path to an easy life, if you will.

I didn't really know what I wanted to do. So I thought, "Oh, well, business people make money. Why don't I try and be a business person?"

Sarah Cottrell: Solid logic.

Dan Lemon: Yes. I think that what you find when you are in business school is that being in business school and studying business as sort of its own independent field puts the cart before the horse. Like, business is almost an emergent property of the thing that you are providing, the goods and services that are being provided to people.

In the economy, it is generally a bad idea and unproductive to engage in business for the sake of business. But anyway, I digress.

So anyway, I graduate from a large state university with my degree in general business administration—I kid you not, that was the name of the degree—and I didn't have a job lined up, and I didn't really know what I wanted to do when I got out and wound up sort of in this space where I was like, "I'm very confused. I don't know what I want to do. I don't have a grand plan for where I want to wind up with my career."

So after doing some exploring, I had kind of reignited this idea that, "Oh, I'm going to go to law school." So I did all the work of applying, and I got in a bunch of places and wound up going to UVA, which I loved.

I was one of the rare people that loved law school, but I think a lot of people at Virginia do because they do a very good job.

Sarah Cottrell: Yeah, it's interesting because so many people who come on the podcast—and just so many lawyers in general—have some kind of experience of like, "Yeah, I got this undergrad degree, which I didn't totally know what I wanted. I didn't really have a clear idea of what I would do with it."

Then essentially, getting on the path to law school gives you a direction. It feels very definitive, like, "I am going in this direction," and that feels accurate. I don't know, or—not even accurate, just like, "That feels like I'm moving in a direction."

Dan Lemon: 100%, yeah. And it helped for me that I was moving in the direction that I had kind of always wanted to move in as a kid. So it felt very clarified for me to be like, "Okay, I'm pursuing this—as the song goes—a lucrative and prestigious vocation," or however the "Don't Be a Lawyer" song goes.

Sarah Cottrell: Such a good song.

Dan Lemon: Yes. But yeah, I mean, you get out of college and you're 22 or 23 and like, what do you know? You discover that maybe the idea you had about what you wanted to do when you were 18 wasn't such a good idea. What do you do?

Sarah Cottrell: In a shocking turn of events, who could have predicted such a thing?

Dan Lemon: So now you have to go and figure it out. Yet to your point, law school is one of those things where it feels very clarifying. Because there's a very defined path for what you do after you get out of law school.

Sarah Cottrell: Yeah, yeah, for sure. I mean, I also think so many people who've been on the podcast who decided at a really young age they wanted to be a lawyer, it does become, I mean, adults when you're a young kid, and you're like, "I want to be a lawyer," in general are like, "Ooh, that's a great life choice." Do you know what I mean?

So you just get all this sort of affirmation that isn't really tied to whether it's truly a good idea for you. It's just this like, "Oh yeah, that would be a good idea," kind of generically. But it gets really internalized when you're someone who's been talking about it since you were very young.

Dan Lemon: Exactly. And also, for me in particular—and this is going to become kind of a theme, I think, as I discuss sort of my story and the path that I took to get where I am today—I was virtually, I would guess, like all of your listeners are, I was a bright and gifted child academically.

When you are a bright and gifted child academically, the messaging that gets pushed to you by your parents and by your teachers and by everybody is that you are exceptional and you are destined for great things. You are going to become the CEO. You are going to become the astronaut, whatever it is, whatever field you are going to pursue, the expectation is that you are going to excel at it. You're going to be very, very good, and you're going to reach sort of the pinnacle of that field.

That was messaging that was really drilled into my brain from a very young age. And what wound up happening, especially when you graduate from college and then you feel kind of lost, and you have to put food on the table—so maybe you take a job that doesn't feel particularly prestigious, and you're just kind of doing what you can to get by—it really feels like you are not living up to your sort of potential and what other people have expected from you.

So going to law school also sort of alleviates that shame—at least it did for me a little bit—that you feel that you're letting other people down because you're not being the excellent person that they all thought you could be. Not that—and again, this is going to become a theme—but not that doing sort of normal, work-a-day, run-of-the-mill jobs is not being an excellent person.

But that's what they mean when they say that you're going to be excellent, is that you’re not going to become a carpenter.

Sarah Cottrell: 100%. Yeah, 100%. I mean, as a gifted kid, I think you get this sense of "Just being a person with a job is not okay."

So it's very easy to have this sense of like, "I have to justify my existence by achieving in a particular sort of way." I think especially if you are someone who is bright and was targeted for a gifted program or whatever, there is this sense of, "And the way in which you excel in life should be in some way academic." Like it can't be being a compassionate person or being a really good community member.

I mean, not that that's bad. But it's like, those are nice, but these are the things that you're supposed to really be good at. And if you're not doing those things, then, "What are you doing?" Like that's what you bring to the table, basically.

Dan Lemon: Yeah. Also, when people are talking about excelling in life, being an American, and I presume most of your listeners are American, but it sounds like not all of them, but being an American, that is very coded to mean that you're going to make a lot of money.

You're going to take some job that's very, very lucrative, and you'll make a lot of money because that is the primary metric by which we define career success in this country. So that is also part of it, frankly.

Sarah Cottrell: Yeah, I think that's so true. I think it is one of those things where you're like, "Oh, huh, yeah." Maybe if that is the criteria that we're using to choose whether to do something, like it's not that surprising if maybe it delivers there and not in a lot of other...

Dan Lemon: Exactly. Exactly.

Sarah Cottrell: But again, it's sort of held out as, "This is..." It's not just like, "Oh, you're going to get a job." It's, "You're going to get a certain type of life."

Dan Lemon: Right. Also, you're going to get the job, you're going to get the money, you're going to get the prestige, all of these things that people in our society think are very valuable. But what gets sort of left on the wayside, as virtually all of your listeners can probably identify with, is whether you're going to be happy. Are you going to be fulfilled in doing what you're doing?

Those things don't matter to those people. What matters is whether you're living up to your potential or not.

Sarah Cottrell: Yeah, I mean, I can remember having a very distinct sense—and I think this is true, I mean, I know it's just true for so many of the people who I work with and so many people who have been on the podcast—of like, "It doesn't really matter if I'm happy."

In fact, worrying about whether I'll be happy is "for other people who are not as equipped to achieve," which is a real gross way of thinking about it when you actually think about it. But it was also very much this, I mean, I definitely had no sense that whether I was happy was a relevant question for what I should be doing career-wise.

Dan Lemon: Yeah. "Happy" is a difficult word because there's no job that you can take where you're going to be elated every single day and just feel great. But it's a question of whether you feel fulfilled and whether you find your work meaningful. These are important things to think about.

It is very prestigious—again, as the song goes, "Help a pharmaceutical company merge with another pharmaceutical company."

Sarah Cottrell: So many lessons you learned.

Dan Lemon: Truly. But is that fulfilling? Is it fulfilling? Do you find that meaningful in your life? When you are doing that day to day, is that something that, when you go home at the end of the day, you're going to feel proud of what you did? These are important things to consider, and not aspects of your career development that are encouraged, certainly in law, but also in a lot of other fields.

Sarah Cottrell: Yeah, it's so true. I think it really is a trap. It's a trap because often what happens is people are say, "Oh well, to your point, it's a job."

You are unlikely to be happy and thrilled with every single moment of any job. It's a job. But so often I see lawyers who are extremely unfulfilled, for whom lawyering is a really, really bad fit. They kind of feel like, "Well, if a job is a job, then every job is going to feel the way this job feels to me," basically.

Dan Lemon: Yes. Yeah, I thought that for a long time.

Sarah Cottrell: Yeah. That's not actually true. Well, would you like to talk about how you felt like that?

Dan Lemon: Yeah, I would. So, yeah, I mean, it was—for a long time, I kid you not—just quick side note. So when I first started practicing, I practiced at a big firm in Ohio and then wound up moving home to Michigan.

So right after I moved home to Michigan and took a job at the largest corporate law firm in Michigan—I'm a litigator, by the way, and I'll always have that, but my—

Sarah Cottrell: Condolences.

Dan Lemon: Yeah. But I wanted to clarify, I'm not on the corporate side. I wasn't helping pharmaceutical companies merge with other pharmaceutical companies. It was genuinely about two rich guys suing each other over ownership of a private jet. I was like, "Yeah, this is why I went to law school was to remedy private jet-related justice."

Sarah Cottrell: So many of us just find it very inspiring.

Dan Lemon: Yes, truly, truly, this is really helping. This is the people that I wanted to help. So, yeah, it was those kinds of cases where it was like giant conglomerates fighting each other over breaches of contract, very rich clients suing each other over petty nonsense.

I did do some cases that are important in sort of the big picture sense in the way that like Apple v. Samsung or whatever is important and shapes the fabric of our society and those sorts of things. But when you're in that day to day, nothing that you're doing ever feels like it matters.

It's so funny because the amount of effort that I was putting into my work versus the amount of impact that I felt that my work had sort of on the world, there was such a mismatch.

It was so all-consuming for me. By the way, I have a family. I had a family when I went to law school. So I was kind of sacrificing a lot.

I was sacrificing a lot of time with my kids, a lot of time with my wife, and I was making money. Yeah. I was grateful for that part of it, that I was able to support my family with the money that I was getting from being a lawyer. But it's like, "What is all of this for? What am I doing?"

I really felt, though, that this is just what it's like to be an adult with a job, is to sort of toil away at something that you don't find particularly meaningful. Because you talk to any other sort of professional, right? An accountant, a financial advisor.

I don’t presume that those people go to work every day and feel real jazzed up about the work that they're doing. I mean, I don't know, maybe they do. Maybe they get really excited when they look at spreadsheets.

But realistically, for me, it was like, okay. But my dad was an accountant. He reinforced that message big time. He said, "This is just what it is. This is just what it looks like to have a job, you go to work and you make your money, and then you go home at the end of the day."

It was so difficult to communicate to people. On one hand, I get that. But on the other hand, there is something about this that feels like it is uniquely miserable.

It was difficult to sort of put that into words or to really communicate that concept to people. Frankly, your podcast and being in the Collab helped, because it gave me words to sort of express why, despite the fact that I was in this prestigious position and I was making so much money, I felt so miserable and depressed and felt like my work was meaningless.

I will tell you—again, spoiler alert—that I've struggled for a long time with the question of, "Could the grass really be greener on the other side of the fence, or am I just going to exchange one bad job for another bad job or make less money?"

I think a lot of people who are in the Biglaw scene think about that a lot. I will tell you that in my case, I think you have to wait for the right opportunity. But I think in my case, the grass really has been greener on the other side.

My quality of life has improved dramatically. Frankly, I haven't taken as much of a pay cut as I thought I was going to. But I'm sort of getting out ahead of myself in the story now. You go ahead.

Sarah Cottrell: Oh, I was just going to say, it's so interesting that you say that because I think it is so true. I mean, so many people have this sense of, it's almost like it's defeatist.

And I don't mean that in a personal, "What's wrong with you?" that's defeatist. I just mean it is a defeating way of thinking, which is this sense of, "Well, this sucks, but everything else is also going to suck, and also I'll make less money. So I might as well stay here where it sucks and make the money that I'm making."

There are so many assumptions—and I think really many false narratives—that are embedded just in that little sort of snippet of thinking. But it's so powerful when you also are someone who got on the path to law school because you were like, "I'm supposed to achieve. This is what I'm supposed to do."

I think it can be hard to see that this really actually is not a good fit for me. I'm wondering for you, at what point, so you graduated from law school and you're practicing, you were at the one firm and then you were at the other large firm, at what point did you start to think, "Maybe this isn't for me"? Was it before or after you were like, "This is making me miserable"? What was that realization process like for you?

Dan Lemon: Yeah, and just to give you sort of the 30,000-foot view. So I graduated law school in 2017. I went to the law firm in Ohio, and I remember at that time really being just so grateful to have a job finally, like a job that paid well. Because I had been in law school, and we had, like I said, I went to law school with a one-year-old. That's a whole story in and of itself. You know, how much time do you have? But you know, I got out, and so we had kind of struggled financially.

So it felt like such a big weight off to be sort of able to afford sort of the basic necessities of life and to be able to buy groceries and not have to worry about it. All of the things that come with sort of a six-figure salary when you're first starting out.

Now, of course, entry-level salaries are even higher than they were then. But at the time, it felt like a king's ransom. So I was so grateful and excited when I first got out of law school.

I really felt like, for the first year or so, that I was kind of on the path. I was doing the thing. I was excelling at the law firm. I was putting in my hours. I was learning everything. I was working my butt off. Everybody loved me.

It wasn't really until sort of right before COVID hit that I was—at that point I had been in for about three years—and I was going, “At what point do I start to feel like I know what I'm doing?”

I would just be honest. “At what point does this start to feel better? At what point does this start to feel meaningful to me?” It just never happened.

So for me, I was just grinding away, grinding away at the billable hours and had another kid during that sort of interim. I would say, it was right before COVID hit where I started thinking to myself, “Boy, maybe this is not the path. Maybe I screwed up.”

Which is a very defeating thought for somebody who—to your point about being defeatist—for somebody who spent their whole life training for this moment and putting in so much work to get to where you are.

And so much money, too, by the way, with the student loans and everything. You put in so much work and so much money to get to where you are, and it is this very stark and dark place to be to realize that maybe this isn't really what I wanted.

“Maybe this isn't really where I belong.” And to sort of, “Now what? Do I start over? Do I go back to school for something? Do I just stick it out and try and make it work? I could just be miserable.”

When I hit that sort of like three, four year mark—by the way, intruder warning, I don't know how trigger warnings work on this podcast—but I was feeling actively suicidal. Me with the two kids.

Sarah Cottrell: I'll say something at the front end on the intro of the episode, so people...

Dan Lemon: Yeah. So yeah, I was feeling actively suicidal. Trying to see a therapist to manage that situation, that didn't really work out for me.

I saw a therapist that was connected with my law firm's lawyer resource program or whatever, and I didn’t have a great experience.

And now, sort of fast forward a year or so, and it’s 2020. I have a baby in May of 2020. And you have to imagine, so I’m at home, I’m learning to work remotely. I’m putting my oldest into virtual first grade.

I have a two-year-old and I have an infant at home in my 1,400 square foot house. And I was like, “This is crazy. I cannot do this.”

So I wound up moving home, in large part to be closer to my family and sort of a support system, because I didn’t have any support system in Ohio. I’m from West Michigan.

So I move home and take a job at a new firm. At first, it is kind of better. But it was—and it’s so up and down, as you know, and as you talk about on the podcast all the time—the experience is so up and down when you’re working at law, or working at a Biglaw firm.

So the feeling that, “Oh my God, this is not the path for me,” would kind of come and go and was influenced by a lot of factors. But I would say it was kind of a slow build over time.

It sort of got worse and worse and worse, and then got better for a while, and then left me in a place where I was like, “Okay, I could do this for 30 more years if I had to, but I wanted to explore other options.”

Sarah Cottrell: Yeah, okay, so literally so many things that you said, I'm like—so first of all, I think I've talked about on the podcast before, but I absolutely love my kids. But the baby and toddler stage for me was not in any way an easy stage.

I have a lot of sensory sensitivities, and just being a parent of young kids and working—especially working in a job that’s super demanding, like a Biglaw job—is just like... it is a recipe for truly horrendous mental health.

So I just want to say that if you’re someone listening and that’s your experience, it’s not because you’re uniquely weak, which of course is how most of us tend to think of ourselves often. It’s because that is just like a cocktail of all of the worst possible things for mental health.

So first there’s that. And also I think, it is sometimes talked about but certainly not as frequently as it should be, but suicidality is such a common experience for so many lawyers.

And it is very often, in part—obviously there are lots of factors—but it's very often, in part, the symptom of just feeling so trapped in what you described as the unique misery of being a lawyer when it’s a really bad fit.

And I think that it’s just important for people to know that how you feel matters. I don’t know. Does that make sense?

Dan Lemon: Yeah. Let me jump in for just a second too, because I just feel like I want to make a clear statement for the listeners.

If you are someone who is in the mental space that I was in, in circa 2019, 2020, where suicide feels, you’re having what is known in the literature as suicidal ideation and what that looks like takes various forms. But you think about it a lot. It dominates a lot of your mental space.

Whether that’s actively planning, or whether it’s daydreaming about it, or what have you, that is not normal. You should really prioritize your own mental health and your own ability to make it in the world over whatever thing it is that is causing you to stay at your job.

Because if you are in Biglaw and you are feeling suicidal, I will tell you that your job is contributing to that. Just full stop. I mean, it just is.

Sarah Cottrell: 100%. 200%. I literally cannot agree with you more.

Dan Lemon: Yeah. Whatever the thing is that you need to change—whether that’s you need to take a break, you need to leave, quit entirely, you need to find something else that’s for you, you should do that.

This is your message that you should do that. Because the suicidal ideology does not stop on its own. It does not get better. You have to change something.

It will help to get on—if you haven’t seen a GP—and gotten on medication to help manage that. Getting on the right medicine does help.

I can testify to that. But also, I can testify that changing the sort of trajectory of your career can be a tremendous help as well. Whatever the messaging is that you have internalized to suggest that it is acceptable to stay in a job that is making you suicidal, if it means making enough money or having enough prestige or whatever, it would be better for you to wait tables or drive for Uber than it would be for you to kill yourself.

Sarah Cottrell: Yes, co-sign. Also, I also want to co-sign mental health medication. We are pro-mental health medication here at The Former Lawyer Podcast. It does actually help.

I think a lot of people, especially if you haven't had experience with mental health medication or have even sometimes, in a lot of cases, sort of been told things that maybe aren't completely accurate about it, have this sense of, "Oh, it can't really help," yeah, it is sometimes trial and error but it can really help, it does really help, and you matter more than any job. You as a person matter more than any job you could possibly do.

Dan Lemon: Yeah, to your point, I had tried different ones. If your first one doesn't work, if you're in this headspace, I tried a couple of them, and the first couple didn’t really work for me. But the third one really helped a lot. So just co-signing that statement too.

Sarah Cottrell: All of these things, I think, are super important. I think one of the reasons why I try to talk so clearly about the kind of misery that these types of workplaces can engender is that people often feel like there's something wrong with them. Like they shouldn't feel the way they feel, and "It's actually not that bad," and "Maybe it's kind of normal." None of those things are true.

Dan Lemon: Yeah, and also, again, if you're sort of actively in that headspace, whether or not you have an entitlement to feel the way that you feel—again, to your point about the internalization of, "Oh, this is just because I can't hack it. This is just what it feels like to be an adult with a job. Maybe there's something wrong with me. That's why I feel this way. I just need to buck up," it doesn't matter. It doesn't matter why you feel the way you do. It doesn't matter whether you're entitled to it or not. That's the way that you feel.

By the way, I would like to add that if you are in a job that is so high pressure, where you have absolutely no control over your own schedule, where stuff is falling out of the sky on you all day, when you're cranking out 60, 70, 80 hours a week, working under tight deadlines with people who are often difficult personalities—and we throw around the word "abusive," but I'm going to use coded language there.

The one thing that I have always championed is this idea that there is no amount of self-care, there is no amount of yoga that you can do, no amount of spa treatments or massages or whatever, that is going to allow you to thrive as a human being in that environment. There's just not. Everybody pays for it one way or the other.

Sarah Cottrell: Yeah. You cannot pay someone to not be human.

Dan Lemon: Exactly.

Sarah Cottrell: Even though all of us gifted kids were basically told that somehow we could achieve and not be human. But anyway. Okay, so Dan, can we talk about at what point, so you said you started thinking, "Oh wait, maybe this really is actually not the thing." Can you talk about that process for you and what you did next?

Dan Lemon: Yeah, so I didn’t really know what to do. What wound up happening was I kind of fell backwards into the career path that I ultimately took.

When I was at my second law firm, the one in Michigan, at one point in time, I was asked to help out with a family law matter. We had a big-name client who was going through a contested divorce issue. One of the first-year associates had written something that the senior partner did not think was particularly good, and I had a reputation at the firm as being a very good writer.

So I was asked to essentially redo the memo that was going to go to the client. What I wound up finding was that I was so fascinated by the concept. I talked to the client, and unlike the nature of my normal work, where you are almost a nuisance to your clients day to day, you know what I mean? If your client is Walmart or something, you’re talking to some employee at Walmart who doesn’t want to deal with whatever the thing is that you’re putting on their desk. Whatever the phone call with you is just a chore that they have to get through before they can go home for the day.

So you're at sword points with everybody all the time. Everything you're doing feels very transactional. One of the things that immediately drew me to family law as a practice is that it's so personal for people.

They're so deeply, personally, and emotionally invested in what it is they're talking to you about. They really care about the results of your analysis. It's not just some abstract, "Oh, the company posts a few more millions of dollars of profit if we settle this lawsuit favorably." It's, "This is the amount of time I get to spend with my kids."

It's, "I've spent my working years building this business empire and I would like to figure out a way to keep it despite my divorce." Things like that, that are so deeply personal and important to people in their day-to-day lives.

So I expressed to this partner, "I really like the family law work. I'd like to do more of it." Over the next couple of years, I built up the practice more and more. But I discovered along the way, as I was thinking, "Boy, I really like this. I think I'd like to make this a niche for myself," or niche, depending on who you are.

I was looking at it thinking, "I don't know how I can do that." I had a chicken and egg problem. The firm I was at was a huge law firm, and its billable rate was so high. How do I build a practice in an area of law that I don’t know very well when my billable rate is higher than any other practitioner in that field in the locality where I’m located?

I was struggling. I think a lot of people, whether it's family law or whatever, if you're at a Biglaw firm and you have this feeling that you're stuck, because there's an area of law you're really interested in, but there's no one willing and able to teach it to you at the billable rate that you would need to charge per your law firm, there are a lot of options that are open. I wound up going to a lot of local bar association events. I met a woman who owned a family law practice here in town, and she expressed, "Well, if ever your current law firm isn’t working out, why don’t you think about coming over here?"

So that's very cool to have somebody express interest in that kind of thing to you. But also, the concept of doing that is terrifying, because when you go to a small law firm, it is much more of an eat-what-you-kill environment, right?

They don't have the money to really absorb a lot of downtime or whatever. You kind of have to maybe take a big pay cut. I don't know. I had no idea what to expect with that kind of a thing. I'm the main breadwinner for a family of five.

I don't have somebody who can sort of pay the bills in the interim. If I'm going to take a jump and not make a lot of money for a while, then I have to really be willing to dip into my savings in order to do that, whatever savings I had managed to build up over the course of eight years practicing law, but also supporting a family of five.

I flirted with this idea, this idea that maybe I should leave and go to a small law firm, for years, but it took me a long time to work up the gumption to do it. Both for the financial reasons that I just mentioned, to get to a financial spot where I was able to, but also psychologically, and this is kind of where I was going at the top of the episode, psychologically, I think that family law is seen among Biglaw firm lawyers as not being particularly prestigious. It is sort of the legal equivalent of becoming a carpenter and just going and building houses for a living or whatever.

There's a recognition that this is important work. It needs to be done by somebody. But that’s sort of for those “other, lesser people,” the people who graduated from law schools that weren't top 14 law schools that don’t have the pedigree that Biglaw firm lawyers have.

And having it drilled into my head from a very early age, as I mentioned, that “what excellence looks like is being at the pinnacle of your profession.” Whatever the most prestigious thing is, that’s the thing that you're going to do.

That made it very difficult for me to make that jump—mentally and emotionally—because it was almost embarrassing for me to tell people that I was considering just moving to a small law firm and becoming a family lawyer.

You sort of imagine that people are going to look at you and go, “Really? You're going to do divorces?”

Sarah Cottrell: Totally. I mean, I think there is very much this attitude, especially if you're a lawyer in Biglaw, of, like, “It doesn't get better than this. Everything else is worse than this. Why would you ever...?”

You would only do something else if you didn’t have a choice. Which is just completely, patently false on so many levels. But I think when you are already someone who got on the path to law school because you were like, “I'm supposed to achieve. I'm supposed to be prestigious,” it's the trap of prestige. You're like, “I'm in this job that is perceived as prestigious.” Then you have this sense of, like, “If I leave, it’s a failure.”

Dan Lemon: Yes.

Sarah Cottrell: Everyone around you is kind of reinforcing that way of thinking.

Dan Lemon: Yes. 100%. So yeah, it was difficult at that point for me to leave, because it took a lot of work. And frankly, as I said, I had sort of mixed results with therapy. One thing that really helped me a lot was journaling.

And I would highly recommend that to listeners, whether you are attending therapy or not, journaling was very helpful for me in working through a lot of this stuff.

One of the conclusions that I came to after a lot of that process—and also going through your program—as you're sort of identifying: What are the things that are important to you? What are your strengths? What are your weaknesses? If you were to think of your ideal job, what does that look like?

I came to realize that the whole concept of prestige—at least as I was raised to interpret it—is really just false. There's just not a lot of substance to it.

If you think about, as I said, I've been comparing this move to just becoming a carpenter and building houses all day, the idea that that is not only not okay, but somehow shameful, to just put in an honest day's work and have a job that helps ordinary people, that that is somehow unacceptable is so crazy to me.

Because who are you. You're just an ordinary person. You too are just here trying to make it in the world. And it is okay to get by just having a job where you do an honest day’s work, receive an honest day’s pay, and go home at the end of the day.

That's acceptable. That's a fine thing. You don't have to be the CEO. You don’t have to be the named partner at your Biglaw firm. It’s okay. It’s okay for you to not have those things.

Just to touch one more side on the economic side of things—I think I said this one more time—but I've been at the job for a few months now. If I’m even going to take a pay cut—and that is up in the air—it certainly is not going to be as big as the paycut I was anticipating.

If you are honest, and you are passionate, and you are good at your job, I think that you can make it. You can make it as a human.

If you’re the kind of person who’s listening to this podcast because you got into a Biglaw firm, you made it all the way through law school, you passed the bar, you are in a position at a very prestigious and very difficult workplace, you can figure out how to make money doing the thing that you want to do.

That was something that really surprised me, frankly. I had to talk a lot with the owner of the firm because everything she was telling me really sounded too good to be true. So my BS detector was kind of going off. But it really has been—I mean, it’s really been great. Truly.

Sarah Cottrell: Yeah, it’s interesting. So I think you used the term “false” when you were talking about prestige. I think that’s such an accurate observation.

Also, I think another important piece of it for people to just be aware of is—if you're in an environment where this idea of prestige is manufactured, right? It's only created and sustained by people continuing to believe that it is true.

And so, when you do or say or make a decision that is in some way contrary to that—something that might disassemble that idea of prestige or show it to be false—you are going to get a very strong reaction from those who are invested in that being the reality.

Because there is a level of security in having a very distinct idea of “this is how things should be,” and “this is what is good and this is what is bad.”

So I think that is also something that is helpful to keep in mind, especially if you're in one of these environments that is high prestige. There is a degree to which it becomes this kind of self-sustaining hologram.

Dan Lemon: Yeah, right? The serpent eating its own tail. At some point in time, you're just doing it to do it, right? You're not reaping benefits from it. I mean, like I said, you make decent money. But if the rest of your life is all in ruins, what's your life worth?

And I always used to joke when I was in the Biglaw firm—and I was talking to other associates—and later, when I was promoted to partner, I became an equity partner at the law firm—I always used to joke that the reason Biglaw is such a toxic environment to work in is because all the people who aren't terrible leave. I think there's some truth to that. Truly.

Sarah Cottrell: Yeah, I don't think that's a joke. I feel like this podcast is sort of like a thesis statement for, “That’s not a joke.” But I mean, it could be a joke. You know, we leave open the possibility for that to not be true.

Dan Lemon: Yeah. Well, the reason I say it was a joke is because there were a lot of good and compassionate people that I worked with day to day.

I think there is some truth to that statement, that all the people who aren’t crazy kind of leave. I think you have to have a level of crazy to spend 30, 40 years at a Biglaw firm.

But also, I don’t want to cast dispersions. You know, there were a lot of people at both firms that I worked with who were good.

Sarah Cottrell: We all contain multitudes.

Dan Lemon: Exactly.

Sarah Cottrell: Can you talk a little bit—I know you mentioned this—but where in the process of all of this did you end up joining The Collab again? Can you talk a little bit about that and what role that might have been?

Dan Lemon: Yeah, gosh, I don’t really remember.

I mean, I started listening to the podcast a long time ago, probably also during the pandemic because, as most of your listeners do at some point in time, I was Googling alternative careers for lawyers, and your podcast came up. So I started listening and I took the plunge and joined the Collab.

Actually, I know exactly when I did it. I think it was 2022 that I actually, or maybe 2023, I don't remember. But anyway, to put that sort of in the context of the process, I was sort of just starting in with the family law stuff, but I had come to the conclusion that I didn't want to spend my career doing what I was doing at the time.

The reason for that at the time wasn't because I had identified family law as a particular area of interest. I kind of was maybe slowly building toward that at the time, but it was because I was looking ahead of me at people who were five, six, seven years ahead of me on the conveyor belt that is Biglaw, and I was seeing them going on vacation with their family, and they would be waking up at four in the morning to respond to emails.

I was just like, "That's nuts. That's not what I want for myself." So I was like, "Boy, I think that I need to find something else one way or the other." But I had no idea what that is. I didn't know what that looked like.

So after listening to the podcast for a while, I wound up joining the Collab. The Collab was very clarifying. Also, certain episodes of the podcast in connection with journaling were also very clarifying.

One thing—one shout-out I will make—was, I don't remember what guest it was you had on that did the hot or cold game. Do you remember that? She talked to you about that. She would ask you, "Do you like it hot or do you like it cold? Do you like mountains or do you like a lake?"

It was a way of reconnecting with yourself, like who you are, because when you're in the Biglaw environment that's all-consuming, it's like you lose yourself almost. You're like, "Who am I if not a lawyer? Who am I if not this gold star-getter?"

Sort of reconnecting with that part of yourself, that was so important for me to just explore. "What do I even like? Who am I outside of work?" And sort of reconnecting with myself on that was a crucial part of my process.

Also, it may have been your husband who was on the podcast at one point in time and said something to the effect of, "You know, it dawned on me that I didn’t like it and I was never going to like it," which is a funny thing to say, that that would be a revelation. But it's like, "Yeah, this isn't actually going to get better." It was a revelation for me that, "Oh, I think that’s true for me too, that I don’t like doing this and I’m never going to like doing this."

So I need to find something that’s better. Being part of the Collab was very clarifying for me. It took a while. I will say it's a process. The Collab is just one part of a larger process, but it is helpful to have the tools and the structure to think through what it is that appeals to you in terms of a profession. It was very helpful for me to be in that environment and with other people who understood what I was going through.

Sarah Cottrell: Yeah, it is a process. And I think it is important for people to—how do I put this—like, if someone tells you there is one answer and they can give you the answer, then I would be very skeptical of that personally. Because to your point, there is so much about it that just has to be taken step by step.

Of course, with the Collab, I try to take some of the guesswork out of that with the framework, because we all know lawyers love a framework, just like, "What direction should I go?"

Okay, Dan, as we’re getting to the end of our conversation, is there anything else that you would like to share with the listeners that we haven’t talked about yet?

Dan Lemon: You know, I would just like to reiterate that your mental health is important. If you are struggling with that, if you're in this place that is kind of dark, that's what I like about my job now as a family lawyer, I get to take people who are in a place that is often very dark and uncertain and guide them to a place that is better and where they can move forward with their lives.

If you are someone who is struggling in Biglaw and you're wondering, "Is this really for me? Is this really what I want to do for the next 20, 30, 40 years?" then just listen to yourself and really take the time to do some real exploration of those feelings and whether your job is actively causing you to be miserable.

Because if it is—and I know I’ve said this already—but if it is, the grass really can be greener on the other side of the fence. That was the strict thing that I struggled with for a long time.

One more story. I know we're getting towards the end of our time, Sarah, but one more story for you. The biggest moment of culture shock that I had when I moved to the new firm was I was the last one there one night because I was kind of trying to get everything set up for my new practice or whatever, and it was probably two weeks in.

I was walking down the hallway, and I realized as I was walking down the hallway that all of the other attorneys at the firm had left their computers in their offices. Nobody had brought their computer home because nobody was checking email after work.

I was so blown away by that because it was always drilled into my head that this is just what it is to be a lawyer. You have to be on all the time, always ready to respond to anything, right?

Having gone to a place where there is a much better work-life balance and where the expectation is not that you are going to respond to every email you get within 30 minutes, it really has improved my mental health and my quality of life. And my ability to do things like attend my son’s Boy Scout events and go to my youngest son’s preschool graduation, it has improved dramatically.

I can’t stress enough how important that is to me and how much of a change you made. So I just wanted to emphasize the grass really can be greener.

Sarah Cottrell: Yeah, it can feel like it is not true. So if you're listening and it feels like that isn’t true, just listen to what Dan is saying and believe him because it is true.

Dan Lemon: It is true.

Sarah Cottrell: It is true. Okay, well, I really appreciate you coming on, Dan, and sharing your story. I think we talked about some things that are super, super important for people to hear. And I'm really glad that you found the podcast and the Collab.

Dan Lemon: Yeah, me too. It was an integral part of my sort of journey. So thank you, Sarah, for starting this.

I think there’s a lot of similarity when you think about it between what you do and what I do, in terms of, you’re divorcing people from their careers, not their spouses, but a little different. We’re both helping people find something better. You certainly were helpful for me.

Sarah Cottrell: Thank you. Thank you again for sharing your story.

Dan Lemon: You bet.

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.