Embrace Your Passion and Leave Your Legal Career Behind with Cary Simowitz [TFLP169]

This episode features Cary Simowitz. Cary met Sarah by email in the summer of 2020 while he was still working as a lawyer.

Before then, he had done a detour and bagged a MFA degree in California, right out of law school. Now, Cary works as the head of legal marketing at a law firm in the Midwest. 

His story is proof that taking a detour as a lawyer is not necessarily a death knell like most people believe. When you follow your heart and ditch the soul-sucking legal practice, you can live the life of your dreams. 

You can start by arming yourself with the necessary information that you need on your journey. This is what the Guided Track with Sarah offers. The Guided Track gives you access to resources on how to leave the law and a community of former lawyers and aspiring former lawyers like you who are ready to walk the journey with you.

From a Family of Lawyers to Law School

Although he came from a family of lawyers, Cary didn’t always dream of being a lawyer or going to law school. 

In college, he was an English and Psychology major and his dad used to gently encourage him by saying that he could use that to become a great lawyer. After college, becoming a lawyer seemed like the responsible thing to do, so he decided to do just that. 

He went to college at Washington University and stuck around for law school afterward. Cary thought that for a few small payments more, he could make a career out of his love for British and Victorian literature.

Toward the end of his undergrad, he sat for LSAT and let the sea of education carry him.  

Dealing with Pressure in Law School

Law school stress began on the first day. 

He was told that if he didn’t spend five hours a night working on his outlines, he’d fail law school. However, he spent his entire time at law school realizing that a lot of the fear-mongering and scare tactics are actually just meant to cause anxiety attacks, leading to failure.

From the first day of law school, Cary wondered if he made the right decision. 

It was extremely challenging because it felt like he was a small fish in a big pond, instead of a big fish in a small pond. Everyone in law school was an A-plus student, so he needed to adjust to that immediately. He called home a few times to report that going to law school felt like a mistake, but his parents and sister encouraged him to give it a year. 

By the second and third years, he had more control over his schedule and could curate his learning around what was interesting to him. For him, the interest was criminal defense. While at law school, Cary externed with the Federal Public Defender’s Office in St. Louis. 

He thinks that his parents’ advice was actually fairly good. Any first-year law student who thinks the world is collapsing on them should simply take a breath. However, if it feels like it’s still collapsing on them by their second year, then maybe that is their gut telling them to look at other options.

Cary learned that if he kept a cool head and approached everything in law with a smirk, he would be fine.

Getting Admitted for an MFA 

Prior to law school, Cary was always interested in creative writing and has a sister, a former lawyer, who is enmeshed in the world of theater. He used to go to her productions and was inspired to start writing plays around the time he started law school. 

Writing plays helped him merge his love for creative writing and theater. 

After finishing all his credits in his last semester of college, he decided to take a playwriting course and started writing. In law school, he wrote legal dramas and comedies as a form of stress release. 

While everyone was doing law reviews, Cary would sit at home writing plays. Going into his third year of law school, he started getting some national attention for his work. Soon, he was offered one of the two available seats at UCLA in their MFA program for theater.

Since he had not started his legal career at the time, it seemed like a once-in-a-lifetime opportunity. So, he moved to LA, where he didn’t know anyone or have been there before to study theater. 

There, he picked up playwriting and ran with it. Later, he was invited to develop a play at the Kennedy Center in DC. He also got an extraordinary chance to develop a play at the Alliance Theater in Atlanta, Georgia. 

All of these successes came with him winning small awards here and there. Those awards were positive motivators to keep going. 

The Risk of Pivoting After Law School

Cary understands the risk of pivoting.

In his third year, he had an exit meeting with the dean of his law school because she wanted him to be aware of the risks. She told him that if he decided to go to theater school before practicing law, he would have a hard time applying for jobs because Biglaw firms would see it as him running away from the law.

She basically told him that he was never going to become a lawyer, so he should have fun. 

At the time, Cary was worried that he was making a catastrophic choice. Now, he wishes that future Cary could go back to past Cary and save him from the anxiety attack. 

Now, he knows that it is possible to get a job after taking an educational left turn. Anyone who says otherwise is simply telling half-truths because there are a lot of understaffed law firms that burn through associates. 

In his case, he returned to St. Louis after his shot at the theater and got a legal associate within two weeks of searching.

Taking on a Legal Associate Position

After graduating with his MFA, Cary was disappointed to see that there was no immediate employment path in the theater. 

He felt trapped because he was underqualified to work in a legal career; even though he had a law degree, he wasn’t licensed. He was also overqualified for positions that would allow him to break into Hollywood.

After three years in LA, his bank account had taken a heavy beating, so he packed everything up and moved back to Missouri, where he had taken and passed the bar before leaving. 

That turned out to be one of the best choices he could have made, even though it was depressing at the time. Three months later, the world was hit with a global pandemic. As a first-year associate at his first legal job, he was working from home.

Experience at the Biglaw Firm

Starting out as a first-year associate was jarring for two reasons: Cary only had three months of in-office experience before the pandemic hit, and he was now required to do work that had little to do with the dream he had spent three years chasing. 

He went from a high-stress, rigorous law school experience to a little more than a fluffy educational experience, only to return to the fires of the legal profession. Unlike those who leapfrogged into their first legal job after law school, Cary didn’t find the transition easy. 

It didn’t help that the firm was notorious for running through first-year associates first. It was a kind of pump-and-dump place, so associates often quit after a year. 

The culture at the firm was so pervasive that his fellow first-year associates were miserable. Soon, he started watching TV in his office during lunch breaks to avoid the negativity going around. 

The firm was simply toxic. Cary felt like he needed to be careful because he was constantly at risk of discovering another missed deadline that could end his career if he didn’t find a solution fast. 

He knew that he couldn’t last long in that space, as he acquired his first therapist during that year. Every day he felt like he was carrying an anxiety creature on his back, and he was constantly unhappy. 

Cary quickly discovered that, unlike when he finished law school exams and passed his bar exam, there was no time to celebrate accomplishments or regroup in the world of Biglaw. Instead, there was enough time to sue for every mistake. That wasn’t what he wanted for himself in the long run. 

Moving into Legal Marketing

Transitioning out of the law was terribly difficult. It felt like he was battling a lot of external forces that were telling him to stay. Those include the heavy investment that went into getting the degree and the confused look that he got from people.

When he started listening to the Former Lawyer podcast in the summer of 2020, he knew that he was itching to make some kind of change, but he wasn’t sure if he should leave the law or not. As a result, he didn’t join any of the programs offered by Sarah Cottrell. 

It was while dealing with that uncertainty that Cary connected with an old law school classmate on LinkedIn. He noticed that she had spun their law degree into a career in legal marketing, essentially working as the director of marketing for a law firm—the firm where he now works.

He just sent her an inquiry message to know what that transition was like and what her day-to-day activities were like. In her response, she told him that she could tell him that or that they were hiring. Since she remembered him from law school and knew of his creative background, she convinced him that he would be a great fit at the firm’s legal marketing department.

At the time, he knew almost nothing about legal marketing or that it was a career open to former lawyers. She had him interview with partners at the firm, and although it was scary, Cary decided to take a leap of faith. 

Three months after he got the job, he got into the director of marketing position because his former classmate left the firm. He got the job at the firm with no marketing experience under his belt.

Leave Your Legal Career and Focusing on Legal Marketing

If, like Cary, you want to make a shift and leave the law behind while hoping that your plans do not fail, know that your decision cannot ruin your life. It only takes a big mental shift from a doom and gloom mindset to an adventure mindset. 

If you think of it as an adventure, you will have more success transitioning out of the law. 

This is why it is important to reach out to people who are doing what you find interesting and talk to them about what they do. Instead of Googling information and trying to figure things out on your own, talking to people will give you better clarity. 

To help you gain clarity and get started with leaving the law behind, Sarah offers you her free guide that shows you the First Steps to Leaving the Law.

However, if you’re looking for a more hands-on experience with accountability and support, you can join the new round of the Guided Track that starts in February.

In the Guided Track, you get access to every resource in the Former Lawyer Collaborative and a small group of lawyers who will meet weekly for 10 weeks. During the 10 weeks, you will follow an action plan created to help you move through the Former Lawyer Framework in those 10 weeks. 

There will also be weekly calls where the group will meet and talk through what they’ve worked on that week. Sarah will be on hand to answer any question that comes up. As a member of the Guided Track, you also get a free 30-minute one-on-one call with Sarah that you can use whenever you want during the Guided Track.

By the end of the sessions, you would have gotten an understanding of what you bring to the table, in terms of both soft skills and talents. You will also know the appropriate language to talk about who you are, the way that you work, and why a non-legal employer should think about hiring you for their role.

Enrollment closes on Friday, February 17th, and sessions start on Monday, February 20th. Sessions will run from February 20th until Monday, May 8th. So, if you want one of the six spots open, be sure to enroll now.

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.

Today I'm sharing my conversation with Cary Simowitz. I am really excited to share this conversation with you because Cary and I first met by email in probably the summer of 2020. We talked about it on the episode when he was still working as a lawyer and he started listening to the podcast, got on my email list, and responded to one of the questions that I send out via my email provider, which we talk a bit about how people are always shocked when I respond to their emails. So just FYI, if you get on my email list and respond to my questions, I will respond to you because I am a human being.

Anyway, Cary has a really interesting story because he went to law school and then he went directly from law school into an MFA program in California because during law school, he started writing plays and it's a very interesting story about how taking a detour as a lawyer isn't necessarily like the death knell that we often are made to believe it is. Cary went from law school to MFA, spent three years out in California, moved back to the Midwest, took a job as an associate at a law firm, and now is the head of legal marketing at a law firm, not practicing as a lawyer.

I'm really excited for you to hear this conversation. I think it illustrates so many important things we talk about on this podcast so let's get right into my conversation with Cary Simowitz.

I am super excited to let you know that a new round of the Guided Track is going to be kicking off in February. So if you've been thinking about working with me to figure out what it is that you want to do that isn't practicing law, now is a great time. First of all, what is the Guided Track? The Guided Track basically takes the Collab and everything that you have in the Collab, the community on Circle, the curriculum The Former Lawyer Framework, all of the replays of the various events, panels, workshops that we have had in the Collab, etc., so it takes all of that. In addition to that, what you are doing is you are going to be working with a small group of lawyers.

This round is capped at six lawyers. What we're going to be doing is we will meet weekly for 10 weeks. We’ll first have an orientation call, then we'll meet weekly for 10 weeks, and you will be following an action plan that I've created to help you move through the Former Lawyer Framework in those 10 weeks. We'll have weekly calls where we will meet and talk through what you've worked on that week, what questions have come up. As a member of the Guided Track, you also get a 30-minute one-on-one call with me to use it whenever you want during the Guided Track.

You also get some free personality assessments that I recommend in the framework. You also get a free CliftonStrengths 34 Report and a half-day virtual workshop with a certified CliftonStrengths coach. This workshop is a favorite of past participants of the Guided Tracks. It is incredibly helpful in terms of understanding what you bring to the table, in terms of both soft skills and talents. It also provides you with a lot of language and ways to talk about who you are, the way that you work, and why a non-legal employer should think about hiring you for their role.

If you're someone who wants that weekly accountability, that small group support, the ability to get on live calls with me and a small group of other lawyers to talk through all of these things as you're working through them, what you are looking for is the Guided Track. Go to formerlawyer.com/guidedtrack and you can sign up there. Enrollment closes on Friday, February 17th, and we get started on Monday, February 20th. The calls will be at 8:00 PM Eastern on Mondays starting February 20th and will run through Monday, May 8th. If you want one of these six spots, go to formerlawyer.com/guidedtrack.

Hi, Cary. Welcome to The Former Lawyer Podcast.

Cary Simowitz: Hey there. It's great to be here.

Sarah Cottrell: I am really excited to chat. We were saying before we started recording that this particular conversation has been a long time coming, so why don't we start with you introducing yourself to the listeners?

Cary Simowitz: Yeah, absolutely. My name is Cary Simowitz. I was born and raised in Florida and then I went to college at WashU and stuck around for law school. It was like the seven-year deal. When I was in college, I was an English major. Specifically, I was looking at British and Victorian literature and I thought to myself, “Hey, I'm glad I have this vast knowledge about the complete canon of Jane Austen but what the hell do I do with that?” So while she was like, “Don't worry about it. For just a few small gigantic tuition payments more, we can make you find a career for that.”

Sarah Cottrell: “We can this way all of your concerns about your future.”

Cary Simowitz: Yes, exactly. But no, in all seriousness, I applied to law schools around the country and felt most comfortable at home. The program obviously at WashU is phenomenal and so it was a very easy choice for me.

Then my life took a very, very strong left turn. I was always interested in creative writing and my sister is heavily enmeshed in the world of theater. She is a former lawyer herself so you might catch up with her one day as well. But she's about seven years older than me and she had the theater bug from the time she was little. I used to go see her productions. She went to an elite theater boarding school for high school called Interlochen. I was bit by the feeder bug as I visited her and somewhere around late college, early law school, I actually began writing plays, marrying my interests in creative writing and theater.

My last semester of college, I had actually finished all of my credits. I was ready to go to law school, I could have graduated a semester early but I thought at the time, “Hahaha, I'm only going to be a student for a short period of time, might as well take advantage of that bonus semester.” That's when I took a playwriting course and started writing. I wrote legal dramas throughout law school as well as a bunch of other dramas and comedies on other topics as a stress release.

While everybody else was doing law review, I was busy sitting at home writing plays. About two-thirds of the way through my law school career, so going into my 3L year, I started getting some national attention for my work and before I knew it, I was offered one of two available seats at UCLA in their MFA program for theater and so I thought, “Well, I haven't started the legal career yet, this seems like a once in a lifetime opportunity,” and so I took the plunge, moved out to LA, did not know a soul there, had never stepped foot in LA, finished the theater program.

I had some extraordinary experiences there, which I'm of course super happy to fill you in about as well, but to make a very long story short, at the end of the day, I graduated with my MFA. There wasn't an immediate path for employment after that, which was a bit of a disappointing, although some might argue, obvious discovery. I found myself trapped. I was underqualified to work in a legal career out there because even though I had the law degree, I wasn't licensed.

I found myself overqualified for the positions that if you want to break into Hollywood, you need to take. Essentially like being a receptionist for a film studio, nobody wanted to hire somebody with a law degree to be their receptionist probably for good reason. So I was stuck. After three years in LA, my bank account hurting a little bit, I packed everything up and moved back to Missouri where I had taken and passed the bar before I left. It turns out that was probably one of the best choices I could have made even though I was a bit depressed at the time making it because three months later, we were hit with the global pandemic.

I moved back to St. Louis, took my first legal job, and then I became a first-year associate working from home which was a beast. But there you go, in 4 minutes and 30 seconds, so very long story.

Sarah Cottrell: Okay, I have so many questions probably unsurprisingly. It sounds like from what you described that when you went to law school, it wasn't like, “I've always dreamed of being a lawyer,” it was much more something that I relate to, and I know many people who've been on the podcast also relate to, which is like, “I don't really know what I'm going to do with this liberal arts degree but becoming a lawyer seems like a thing that responsible adults do so I'm going to go in that direction.”

It sounds like you didn't necessarily expect to start law school and just think, “This is just amazing and I love every moment.” But as you were going through law school and you were doing the law school thing but then also writing these plays on the side, was there ever a point, and if so, when was it, where you were like, “Do I actually want to be a lawyer?”

Cary Simowitz: You hit the nail on the head. I come from a family of lawyers. My dad was an attorney. My sister who, as I mentioned, is significantly older than me—although not significantly old, she'd kill me if she heard me say that—was also at that point in law school throughout my college career as I was obtaining my English major and also I was a psychology major as well. My dad was constantly gently saying, “Hey, you could use all this to be a really great lawyer,” so I was in that exact position that you described.

I was reaching the end of my undergraduate career, I didn't quite know what to do with the degrees that I had obtained, and so I sat for the LSAT, it felt like the most responsible decision at the time, and I let the sea of education just carry me along if that makes sense.

Sarah Cottrell: Totally.

Cary Simowitz: I believe your question was was there any point during the journey when I thought, “Oh, my God, what am I doing? I need to get off of this feeding train while I was in law school”?

Sarah Cottrell: In particular in law school.

Cary Simowitz: Yeah. About maybe the first day, the third day, the first week, the second week at the end of first-year exams, oh my God. I will tell you the first year of law school, especially if you don't know much going into it, is extremely challenging. I was a very high-achieving undergraduate student and I had to get very used to being surrounded by high-achieving students.

What's the expression I'm looking for? it's like small fish, big pond instead of big fish, small pond. Everyone was an A-plus student and so I immediately had to get used to some Bs and recognizing that that's okay and that the journey is a challenging one. I will say that the few times that I called home basically saying, “This is a mistake. I don't know what I'm doing here,” my parents, and eventually, my sister kept saying, “Just give it a year. Give it one year and then at the end of it if you're not feeling it, then you can consider other life paths and there's no shame in it.”

To WashU's credit, it was a fantastic experience being a WashU law student. That was another strong incentive to stay despite that deep feeling that, “Hey, something about this doesn't necessarily feel like me,” and I will say the doubt that crept in crept back out again for second and third year. I felt much more comfortable. First year was a roller coaster. I described it to a lot of folks as a repeat of high school. If you had a less-than-amazing high school experience, you get ready for some not-fun flashbacks.

But second and third year of law school feel a little bit like a repeat of college where rather than being in the same five classes with the same 30 people all day every day, now you have choice over your schedule, you can cater your path to something that you're more distinctly interested in, and for me, that was criminal defense so I could take as many criminal defense classes as I could find. I externed with the Federal Public Defender's Office in St. Louis and I was very much reassured throughout my second and third year.

I think my parents’ advice was actually fairly good. I think if any first-year law students are listening to this right now and they think the world is collapsing on them, take a breath. If it feels like it's still collapsing on you into your second year, then maybe that is your gut telling you might be time to think about other things, if that makes sense.

Sarah Cottrell: Yeah. It's interesting because ultimately, from what I understood from what you said, you went straight from graduating law school into the MFA program in California, is that right?

Cary Simowitz: Yep, that's correct.

Sarah Cottrell: Okay, can we just talk for a minute about how that's a very unlawyerly move? By that, I mean the risk, the sunk costs, and all of those things. I feel like there are many people who would just be like, “Well, clearly, that's not a thing to do. I wonder, based on what you've talked about, whether for you it was just you just loved the playwriting so much that it overrode any of that, what was the dynamic there for you?

Cary Simowitz: Yeah. It's funny that you mentioned that because I'll never forget I had an exit meeting at the end of my third year. I had already committed to UCLA, I knew that's where I was going. I had an exit meeting with, I believe it was the dean at WashU Law and she had said to me at the time, “Hey, I just want you to be aware that if you take this path, if you decide to go to theater school, and then you decide you want to practice law after that, you're going to have an impossible time applying for jobs. Biglaw firms will look at you like you were running away from the law. You're never going to get to become a lawyer so good luck, have fun. Goodbye.”

Sarah Cottrell: “You're making a terrible choice.”

Cary Simowitz: Exactly. That was the spark notes of that meeting. At the time, that scared me. I felt petrified going home. At the end of that meeting, at the end of the day, I was worried that I was making a catastrophic choice. I wish future Cary could go back to past Cary and save me the anxiety attack but I will say that three years later when I came back to St. Louis and I had been away from the law and I needed a job in a hurry, I got a job within two weeks.

Whatever that sentiment was, maybe my first legal position is not going to be for $150,000 at the most prestigious law firm in the country, but anyone who tells you that you can't find a job as an associate even if you take an educational left turn is selling you a bit of good because there are plenty of understaffed law firms all around the country that burn through associates, as I'm sure you've talked about with other folks who need some associates to replace those associates they just burn through.

Sarah Cottrell: You paint such a beautiful picture.

Cary Simowitz: I appreciate that.

Sarah Cottrell: Yes, and I think there is also that element of the way in which the legal profession can be extremely, what is the word that I want to use?

Cary Simowitz: This makes me think of there’s a script to all of this. You encounter it as soon as you start law school. Folks will tell you that if you don't spend five hours a night working on your outlines every single day, you will fail at law school. I feel like I spent my entire law school career realizing that a lot of the fear-mongering, the scare tactics are actually just meant to give folks anxiety attacks and have those cause them to fail.

Whereas if you keep a cool head, if you approach law school and even life as a lawyer with a little bit of a smirk, not too much of a smirk but just a small smirk, find a way to smile, you can get through it. It depends on what kind of a law student you want to be. If you want to be the absolute top of your class working at Greenberg Traurig or any one of the other gigantic law firms, Bryan Cave, sure, then yes, you probably do need to put in an exorbitant amount of time and take all of the fear-mongering seriously.

But for the other 99% of us, which there is nothing wrong with the other 99% of us, we will all still have wonderful careers as lawyers if we so choose and make an excellent living, sometimes I think that these scare tactics are more for the psychological game of being a lawyer, which I think isn't healthy.

Sarah Cottrell: Whoa, whoa, whoa, wait, are you saying someone isn't a morally better person because they don't go to work in Biglaw?

Cary Simowitz: Oh, man. I can't say that. I feel like the law police will come after me.

Sarah Cottrell: I know it's so true.

Cary Simowitz: I think if I didn't torpedo my Biglaw career six years ago when I went to UCLA, I think I just torpedoed it now.

Sarah Cottrell: It’s all over.

Cary Simowitz: Yeah, absolutely. I'm done.

Sarah Cottrell: Okay. Let's talk about, so you move back to the Midwest.

Cary Simowitz: Actually, I just realized I didn't answer your question about the choice to actually go off to UCLA. Did you want me to touch on that at all?

Sarah Cottrell: Oh yes, please do.

Cary Simowitz: Yeah. I have an unbelievable love of theater, and as I said, creative writing and it marries the two and that's wonderful. I also was deeply interested in writing for film and television as well, which I obtained those skills at UCLA as well. What I will say is that I'm very fortunate in that it was a skill that I just tripped into success with a little bit. I had been writing short stories and poetry all throughout my undergraduate experience and so I learned the conventions of story and what goes into making strong fiction and creative literature.

But when I picked up playwriting, I just flew with it. I feel like everyone has a secret hidden talent that if only they try enough things, they'll find it. It's like if you pick up every single musical instrument, who knows? You might be a prodigy at one of them. But at the risk of tooting my own horn and staying with the instrument metaphor, I got a lot of really great positive reinforcement early on.

I was invited to develop a play at the Kennedy Center in DC, which was extraordinary. I was invited to develop a play at the Alliance Theater in Atlanta Georgia, which is also an absolutely extraordinary opportunity. All of these successes actually came shortly into the program but I was winning small awards here and there before I made the decision. But all of these were positive encouragement, keep going, you might have something here. I think that's what really helped me take the leap.

Sarah Cottrell: Okay. Let's talk about when you moved back to the Midwest and took this associate job that was basically starting remote because of the pandemic, can you talk to me about one, what that was like being in your first formal legal job after this detour?

Then related to that, can you also share a little bit about I think a lot of lawyers, one of the reasons that they wouldn't take a detour like the one that you did is there is a lot of concern about needing to succeed and a lot of lawyers place a lot of like, “Well, if I do this thing which is slightly out of the norm or maybe very out of the norm and it isn't wildly successful in one particular way, then my whole world will come crashing down so I'm just not even going to entertain the possibility of doing such a thing”? Can you talk a little bit about that piece of things and how that worked for you?

Cary Simowitz: Yeah, absolutely. Beginning work as a first-year associate was a jarring experience for two very big reasons. One was the pandemic that we've talked about. I began at that firm in December, the pandemic hit in March so I had a solid three months in the office for whatever that's worth. The other jarring aspect of it that's probably more unique to me than anybody else is the fact that I had just spent three years living a pretty great Bohemian life in LA chasing a dream that had very little to do with the law aside from the fact that many scripts that I wrote were legal in nature.

I went from a very high-stress rigorous law school educational experience into what I'm going to call generously a little bit more of a fluffy educational experience and then right back into the fire. I think folks who leapfrog straight from law school into their first associate job, which is the traditional path, might find that transition a little bit easier, more easily achievable. I had to retrain my brain to think, “Okay, now I have an enormous amount of work to do, a lot of responsibilities, a lot of deadlines. Vacation is over. Time to get back to work.”

I think there were hints of sadness and all of that because I had become very focused on achieving the dream of becoming a staff writer for a television show out in LA, which I discovered about three months into living in LA. It’s a little bit like saying that you want to pitch for a major league baseball team. Good luck. I gave it the old three-year try but I was carrying a little bit of a taste of defeat into this role, which is crazy if you think about it.

A lot of people around the world dream of becoming a lawyer, so how odd that becoming a lawyer felt a little bit like being defeated. Especially the language in LA that I was frequently combated with was, “Oh, well, you're a lawyer. So if this doesn't work out for you, you're fine.” When I was working at production companies, they were like, “Why are you even here? Are you allergic to money?” as soon as they would find out that I was an attorney.

There was this sense amongst the Hollywood community that like, there's this stupid expression, I'm sure you've heard that, I think it's honestly in every field, if you can think of yourself doing anything else, then you shouldn't do the thing that you're in right now.

Sarah Cottrell: Yeah, it's the worst.

Cary Simowitz: Yeah. I faced that a lot in LA with proof that I could think of myself doing something else. I was talking before about the difficulties that I was having breaking into the industry. One of the weirdest hurdles I faced was that people would find out I was a lawyer and roll their eyes and be like, “Who is this guy?” But anyway, then I carried that back into becoming an attorney and the firm that I worked for is notorious in being a first-year associate, for lack of a better term, pump and dump kind of place, which I'm sure you've encountered and I've heard from your podcast other folks talk about.

It was an insurance defense firm. The idea of that law firm was we're going to work you to the ground, you're probably going to quit after a year, but don't worry about it because we have 100 other first-year associates we can replace you with when we're done with you.

Sarah Cottrell: Inspiring.

Cary Simowitz: Yeah, exactly. That culture was pervasive. The first-year associates who I was working with, I had this extroverted fun Hollywood personality and my fellow first-year associates were miserable. I remember I used to get lunch with them the first couple of months because there was a cafeteria on the ground floor of the office building and I stopped going after a couple of weeks, not because I didn't feel like I didn't fit in but because they were all talking about how much they hated their lives constantly. Instead, I just watched TV in my office with the door closed and ate lunch there because I was like, “Well, at least Brooklyn Nine-Nine won't give me depression.”

Sarah Cottrell: I was going to say depress you. It's so interesting because right now when we're recording this, I'm in the middle of running a Guided Track, which is a more intensive smaller group where we meet more often, people are working through The Former Lawyer Framework, and the conversation we just had last night was in part about how humor, really any kind of humor is not valued particularly in the law firm context.

If you are a person for whom that is either a very high value or it's one of your strengths, you're made to feel like “Why are you here?” basically. Just having a more enthusiastic personality, law firms are like, “Can we just stomp that out of you, please? Thank you.”

Cary Simowitz: Yeah, absolutely. I can relate to that a lot. I feel like often, my extroversion and my humor, people can interpret that as either “This guy isn't serious, or frankly, this guy's dumb.” But then they see my work product and hopefully, that changes their mind. I'll never forget the first week of law school, in one of our orientation sessions, they made us go around the room and say “what we wanted to be when we grew up,” and everyone in that large lecture hall was saying, “Oh, I want to be a public defender,” “Oh, I want to work for the gigantic Biglaw firm,” etc., and just to break the mood I said, “I'm Cary and I want to be a famous actor,” and nobody laughed. I was like, “Okay, this is not the crowd. This is not the room.”

Sarah Cottrell: Oh, the crickets. It's a special kind of law crickets. They're extra crickety.

Cary Simowitz: Exactly. It's just wild. I thought at least maybe I'd get a chuckle but I was like, “Oh, sh*t. This is great a new world I just stepped into.”

Sarah Cottrell: We’re very serious here. Okay. You started in December of 2019, the pandemic hits a couple of months later, you already basically know like, “Oh, this is not the place.” It doesn't sound like you necessarily went into it thinking, “Well, this thing in California didn't work out but now I'm going to do this other thing, which I'm definitely 100% excited about and think this is going to be the thing.” It doesn't sound like that was necessarily your mindset. Talk to me about your thought process about where you were, what you were planning to do, and all of that.

Cary Simowitz: Yeah, absolutely. I think I'm the type of person in life that tries to put my best foot forward no matter the situation. I don't want to say that I 100% did not want to be an attorney. That's not true. I was intimidated by the amount of work that hit me right at the gate, although I knew to expect it. I was worried that I might become, especially at a lot of these large pump-and-dump insurance defense firms, they just tossed first-year associates out there and say, “Good luck, don't lose your bar license,” and there was a little bit of a similar feel.

But the partner that I was working for, I actually really, really liked. He was phenomenal. He actually just took the entire floor of that firm that I worked at and built his own practice. I'm really excited for him, I thought that was great. He was just very patient with me. He was very enthusiastic about me. He was the kind of guy who enjoys movies and motorcycles so I think he thought I was cool having come from Hollywood.

I think in some small ways, it's just great if you start out and your partner, who a lot of people are intimidated by, just likes you for no real quantifiable reason. I think that's great. Don't fight it. If your boss likes you going in, that's a great place to start. I enjoyed the experience, it just was constantly triggering my anxiety. I'm a perfectionist, as you mentioned earlier, I was handed something 40 or 50 case files right off the bat all of which were in various states of disarray.

I'll never forget I received one case file that I had to write a motion for summary judgment for, which I think most folks, well now comes midway to later in the pre-trial process. So I wrote this motion for summary judgment, was very proud of it, threw in a couple of references to my favorite TV shows because why not, didn't feel too bad when they were all edited out because of course that's going to happen, and then about a month or so, or six actually later, the motion for summary judgment was denied.

It's like, “Okay, great. Oh, well, that's a bummer. Now we have to prepare for trial.” So I turned back to my materials and I realized that the first-year associate who had the file before me never performed discovery at all, not at all. Those deadlines had all elapsed like a year or more ago, no interrogatory set, no requests for anything, barely answered the discovery that we were served.

I remember going to one of the senior associates and saying, “Oh, my God, how are we going to go to trial on this? We have absolutely no discovery.” The senior associate said to me, “Well, that sounds like a lot of excuses.” I was like, “What? What?”

Sarah Cottrell: Tell me you're in a toxic workplace without telling me you're in a toxic workplace.

Cary Simowitz: Exactly. I was like, “Well, this is my bar license on the line here. This is very, very bad.” I think I had the everything is on fire feeling all the time, which may be indicative of other law firms, it may not, but I could not go for much longer than a year with waking up every single day riddled with anxiety, and that everything is on fire feeling. It was affecting everything.

If you went on a date with me during 2020, which you probably almost didn't do because we were in a global pandemic, but let's say we went on a picnic with a six-foot-long picnic blanket, I wasn't super fun. I was glancing at my phone. I was worried about emails I might get. I was worried about making another discovery of another blown deadline that would be career-ending if I didn't find my way out of it.

It just didn't feel like a scenario in which I could thrive long-term. I also acquired my first therapist during that year. He's a great guy. I'm still with him several years later even though I'm not a lawyer anymore. I think he's just thrilled that I'm not coming in to complain about being a lawyer these days. Now you can get down to the real stuff like my relationship with my parents.

But that's what I think made me the most anxious and unhappy. I felt like I was carrying an anxiety creature on my back every day for a year plus. It wasn't necessarily that I was being mistreated. I tried not to let the toxic culture that my immediate supervisor, my boss really wasn't that engaged in. This is a law firm where there were hundreds of partners who treated their associates hundreds of different ways.

If you landed with my particular partner, you'd have a decent experience, to a good experience, a great experience. But there were other first-year associates there who had chairs thrown at them. I think what I'm trying to say is that it wasn't necessarily the circumstances of the fact that I was working at that firm that made me get really excited to leave. I wasn't being mistreated. The work was insanely hard but I was doing the absolute best I could. I think it was that feeling that everything's on fire all the time and there's no way to dig your way out of it.

One of the things that you do in law school is you take final exams at set periods of time every year, you study like crazy for them, then you finish them, and you get about three weeks if it's fall term, an entire summer if it's the end of spring term to just recoup and celebrate the accomplishment of having achieved that exam. When you take the bar exam and you finish it, you have a minute to breathe out and celebrate the fact that you finished the bar exam before panicking about whether or not you passed it.

But what you quickly discover in the world of a large law firm is that every day is the final exam and there is no time to celebrate accomplishments but there is endless time to sue in all of your mistakes.

Sarah Cottrell: Yeah, it's interesting because I think what you're describing in terms of your experience of how anxiety-provoking it was, I think often people feel like they must be the anomaly because it's like, “Well, it just isn't reasonable that an entire company or profession would basically have everyone more or less feeling this way or some variety of this way. That would just be ridiculous so I must be some outlier,” when in reality I think what you're describing is the natural nervous system response of humans to stressful/ridiculous situations.

I think part of what can create such a terrible culture in these firms especially is the fact that people are basically, in many cases, denying the reality of how the experience makes them feel, particularly people who are in positions of leadership and authority within the firm, and then all of that unacknowledged anxiety is just like spewing out with no awareness onto everyone around them.

Cary Simowitz: Oh, absolutely. I think that's part of the reason why I tried to isolate myself from the other first-year associates. I tended to even gravitate towards some of the senior associates if I could because at least they were in the day-to-day grind of it. But the overwhelming anxiety, and people adopt all sorts of different defense mechanisms to combat anxiety, some folks become holier than thou, some folks dissolve into a puddle of tears. There were a couple of first-year associates who cried every single day and didn't last much longer than a couple of months because there's only so many times you can cry in front of your boss.

By the way, I'm also speaking to you from the position of being a straight white male. My law firm was overwhelmingly white but it definitely did employ a sizable number of women, non-white folks, and non-straight folks and their experience was probably twice to three times as hard as mine because a lot of the people in positions of power reflected more of what I brought to the table.

I cannot say for certain, I really can't, again because I was not in this experience. But it's my understanding to the grapevine that most of the women that I knew who were working, really just at any firm, I don't even want to pin this on any specific firm I've worked at, have two to three times more challenges than anyone else. Actually, that's probably any industry. Look at me.

Sarah Cottrell: I was literally just about to say before you said, “This is probably any law firm,” I was about to say that yeah, basically at every law firm, which is a truly problematic indictment of, again, many systemic things within our profession, and not even necessarily individual places, although individual places also that have their own individual special brands of toxicity.

Cary Simowitz: Absolutely, no doubt. I do believe this law firm employed a good deal of women, there were not too many folks of color. If you were a person of color at this law firm, oh my God, even if you're treated phenomenally well, I imagine it's a difficult situation to be the only person who looks like you in a gigantic building. I'm sure it is.

Sarah Cottrell: Yeah, not speaking about your specific law firm, just law firms in general, especially doing this work, I have the stories that I have heard, there are no words. Okay, you've already alluded to this but you decided, “This is not going to work for me. This is not an emotionally and mentally healthy situation for me to continue in.” What was that decision like and what did you decide to do next?

Cary Simowitz: It was terribly difficult. I know folks have talked to you about this before but you're battling a lot of external forces that are telling you not to leave or not to deviate from the path. You're battling the investment that you put into a law degree. You're battling another round of people giving me confused looks. People in Hollywood were like, “What the heck are you doing being a lawyer?” People in other contexts are now saying, “Wait, could you just not crack it in the legal industry? You're a lawyer but you're doing something else, what's that?”

Not only that. As I mentioned before, I was very lucky in that I enjoyed working for the partner that I was working for. I actually thought that I was getting, slowly but surely, better at what I was doing. It wasn't necessarily a five-alarm fire at the time but I knew that I was itching to make some kind of a change and that's when I first started listening to your podcast back in, I want to say summer of 2020 I think is when I stumbled upon you.

I wasn't sure whether or not to take the leave. That's part of the reason why I didn't immediately join any of the programs that you are offering that I'm sure are phenomenal because I was like, “Well, do I want to leave? Really I'm not sure.” How I found my way to this new position was through an old law school classmate. I connected with them on LinkedIn because I noticed that they had spun their law degree into a career in legal marketing essentially working as the director of marketing for a law firm, the firm that I am now working in.

I just sent her an inquiry, an in message saying, “Hey, that's an interesting career left turn. I feel like I'm the prince of career of left turns. What's that like? What do you actually do in your day-to-day?” Basically, how she responded was, “I could tell you or we're hiring. I remember you from law school. I could just show you.” She was very encouraging from the minute that I first reached out to her and she started to actually convince me, she knew of my creative background, she worked to convince me that I would actually be a great fit at this firm in this particular area of legal marketing, which is something that I knew almost nothing about.

I had no idea that was a career even open to folks who got their law degrees because they don't have a whole branch in your law school's career services on alternate career paths or legal marketing. It's just not a thing. Maybe if the U.S. News & World Report gave schools boosts for churning on some alternate students, there might be, but we're not there yet. But anyway, I talked to her, I had many, many phone calls with her.

She had me interview with many of the partners at my current firm, and again, this was another opportunity in life where I took a leap of faith. It turned out to be a very scary leap of faith because I remember talking to her back at the time, the way that she was describing the job, the way that she was describing how she now had all these upward career options and how she longed to move to a big city—because, again, we're still in St. Louis, which is very nice, it's a wonderful town but it's smaller than Chicago, New York, or LA—I remember saying to her at some point, “This feels like you've got two feet out the door. Are you trying to recruit me so that you can accept another offer and get out of there?” and she was like, “Oh, no, definitely not. I'm at this firm for life.”

Smash cut to three months after I took the job, I'm now the director of marketing at this law firm because she peaced out, which I'm so grateful to this law firm for taking a leap of faith on me considering I had basically no marketing experience entering this job. It has been an insane year ever since she left. I've basically had to give myself a master course in what it even means to be a marketer in real-time, which it’s been an interesting year.

Sarah Cottrell: Well, and marketing often is not something that comes naturally to people who train to be lawyers. Even if it comes naturally to you, it is a completely different skill set in many ways. Although I can see how with your particular background, there might be more overlaps than with the typical person coming from a law school background from a law background.

There are two particular reasons that I had in mind in terms of wanting to have you on the show. One was just for people to hear that you can make these changes and it doesn't have to be into something where you're like, “Oh, yes. I am 100% prepared for that role in the sense of that's what I've been training to do all my life.” That's one. Then the other was when people get on my email list, I send a question or occasional questions like, “Well, how long have you been thinking about doing something else?” and people are always very shocked that I actually respond when they respond to me. They're like, “Wait, you're not a robot?”

Anyway, for anyone who is not on the email list, if you wonder if do I actually respond, I do actually respond. But I remember us talking some about you potentially joining one of my programs and ultimately, you did not. You also made this change and I think that's so important for people to hear because obviously, I create these programs to help support people and I love doing it but also there are many different ways to go about making this change and I always want people to know they're available but I never want to project this idea of there's some secret that I have and no one else has, and if you don't have access to this secret, then too bad for you, basically. Can you just a little bit about either of those things?

Cary Simowitz: Yeah, absolutely. I can tell you that the fact that I didn't join your collective is partially based on the serendipity of this circumstance. I think that had I not stumbled into my friend on LinkedIn and had she not directly recruited me for this role, if another three to six months had gone by, and I was still struggling with this feeling of anxiety, which also can't be mentioned enough, we're in the middle of a global pandemic where I was wiping down my groceries every day, that also might have been a huge amplifier of that anxiety.

I always wonder, “Well, if I would have had a typical first-year experience, maybe I'd still be a lawyer. Who knows?” But anyway, all that is to say if another three or six months had gone by and nothing had changed, I would absolutely see myself committing to one of your programs. It seemed like a great resource. It's almost like I didn't discover it in time. I had it in my back pocket for a couple of months while I was having these conversations with myself about a legal career and whether or not I wanted to stay or go, and then an opportunity just presented itself.

I almost feel like I'm telling a story of a person's life where opportunities just presented themselves. I had the ability to go to UCLA out of nowhere. I had the ability to go to WashU Law. Obviously, I studied for the LSAT. Obviously, I wrote a bunch of plays but other folks can do the same things and not have the luck and the preparation to have those results. I think it's just been a case of me saying yes to a lot of things and hoping against hope that I don't regret any of the decisions that I make.

If you're the type of person, I think that's a big mentality shift, if you're willing to leave the world of law to pursue something else, I think you can either get stuck in the mire of “Oh my God, I'm making a decision that's going to ruin my life,” which, spoiler alert, you're not, you're still living and breathing no matter what choice you make. If you can get out of that doom and gloom mindset and into the, “Okay, this is going to be an adventure that I'm going to say yes to,” I think you'll have more success.

Sarah Cottrell: Well, and that's something that I wanted to mention that I think is really important from your story about how you ended up in your current role. It seems small but you saw someone doing something that you thought was interesting and you reached out and said, “Hey, can we talk and can you just tell me a little bit about what that's like?” You didn't immediately reach out and say, “Can you get me a job?” or “This is interesting, here's a bunch of details about me. Can you tell me whether you think I'd be a good fit for this role?”

Just showing curiosity in what someone else is doing that is something that you're interested in is a huge part of what is necessary to really get clarity. I think for many of us lawyers, it can be very easy to feel like we can think our way to clarity on that. You see someone doing something you think is interesting and you think about it, you think about it, and you think about it and you research it by Googling stuff.” I'm not saying that stuff is bad but the way you ultimately get clarity in like 99.9% of cases is you make that contact, you ask that question, you talk to that person. They connect you with someone else or they give you some piece of information that you didn't have before. That is really where it happens.

Cary Simowitz: Yeah. That's absolutely correct. I think you hit the nail on the head. I think showing genuine curiosity can often start conversations more quickly. It's like negotiation tactics. If you show up and say, “Hey, I want this thing. What can you do to help me get it?” and the person that you're speaking to doesn't know you or has had no significant contact with you, they're like, “Alright, I know you need some help and I'll try to get to you eventually. But I've got my own life with my own wants and needs. Maybe we'll see. You never know.”

But people love to talk about themselves as evidenced by this podcast so if you come to somebody and say, “Hey, your job seems super cool. What exactly do you do every day?” I guarantee you you're going to start a conversation.

Sarah Cottrell: Yeah, 100%. Okay, Cary, as we're getting to the end of our conversation, is there anything that you would like to share that we haven't had a chance to talk through yet?

Cary Simowitz: The only other thing that I can think of is that, I'm not sure, have you spoken to anybody else on this podcast who has gotten a legal adjacent career in a law firm that is no longer practicing law? Has anybody you've spoken to had that experience?

Sarah Cottrell: I'm trying to think. Rachael Philbin was on the podcast a while back. She does like a knowledge management-type role. That is the only person who comes to mind immediately.

Cary Simowitz: Yeah, absolutely. The only other thing that I can say in general, and I'm not ascribing anything really positive or negative to what I'm about to say, it's just that if you decide to leave the practice of law but still work in a law firm, whether or not you're working in their HR office, in marketing, or in any other way, shape, or form, it can be a little bit of a mental adjustment to realize, “I am not here as a lawyer anymore.”

I think that is an adjustment that takes some time to figure out because you will see legal meetings. If you're in marketing, you'll be in a mass torts meeting where a bunch of lawyers are talking about, “Oh, I think this tort would be great,” etc., and you have to remind yourself every once in a while, “I'm not a lawyer anymore. I'm going to contribute to the extent that I'm a marketer but I also need to remember that I am in a completely different lane now.”

That lane comes with positives and negatives. If you work for a law firm in a higher up capacity, you can still make a very wonderful living, you get to go home at five o'clock every day, shut your brain off for the night, and go on dates, enjoy time with your significant other, or catch up on House of the Dragon and not have to worry too much on what your phone is doing.

At the same time, you may or may not, most likely will not, be invited to the attorney baseball game that everybody gets tickets to and goes to. You have to be like, “Alright, my ego isn't going to be wounded by that. I understand that I'm no longer a lawyer anymore.” It's a little bit of a trade-off, if that makes sense.

Totally. I have had clients who have gone into legal adjacent roles in law firms. I was going to say, which you basically said this, I might say it slightly more directly, lawyers can be real a-holes to people who they don't perceive as lawyers because many lawyers believe that to be a lawyer is to be the pinnacle of all humanity. If you go into a role in a law firm where you are interacting with a lot of lawyers, the chances that you interact with some humans who have that perspective is much higher than if you go into a different type of role.

That's just something to be aware of because I do think there is a level of personal development work, therapy, etc., that you want to have done/be doing because encountering that can be, let's just say, like grading.

Cary Simowitz: Yeah. I definitely understand that. Even taking it outside the context of my law firm, I just attended last week a huge convention that folks listening to this may or may not know about, it's called Mass Torts Made Perfect, it's held in Las Vegas every year, a huge amount of lawyers gather and talk about what's trending in the world of mass torts. You get all of the giant law firms there that are in this space.

My co-workers wore name badges that said attorney on them and I wore a badge that said legal professional on it. I would have conversations with attorneys from other law firms who would speak to me in one tone of voice when I was a legal professional and then when I would find a way to sneak in, “Oh, yeah, actually I have a super unique perspective on all this because I'm actually also a lawyer and how great that my law firm actually took me on as a lawyer as well.” The tone of voice changes, the way that I'm addressed changes. It's a little bit like a class shift that I was interestingly keeping track of, if that makes sense.

Sarah Cottrell: Yes, 100%. Just like forewarned is forearmed. Okay, if people would like to connect with you, Cary, where can they find you on the internet?

Cary Simowitz: Yeah, absolutely. I'm on pretty much every form of social media. I'm on LinkedIn. I'm on Facebook and Instagram. Also, if people are interested in my theater career, I'm on the LinkedIn of playwrights which is called New Play Exchange. If you do a Google search of my name, I think it's one of the first links that pops up. If you feel like reading some of my legal dramas or leaving me reviews, that's always fun. But yes, anybody who wants to learn more about my experience is more than welcome to reach out to me on any one of the social media channels.

Sarah Cottrell: Awesome. Thank you so much for sharing your story. This was really fun.

Cary Simowitz: I agree. This was great. Thanks for what you do.

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.