Finding an Influential Career in Coaching After Being Let Down by Biglaw with Erin Conlon [TFLP027]

Welcome back to Former Lawyer! This week, you’ll learn about Erin Conlin, who had a job practicing law for almost 15 years before finding a much more influential career in coaching. 

Erin graduated from law school and landed her dream job, only to get laid off because of the recession in the late 2000s. Then, she spent almost a decade as a discovery counsel before making the leap to coaching. 

In this article, you’ll learn about Erin’s transition from her original pursuit of litigation to discovery counsel. And, of course, you’ll also learn about why she decided to leave the law and how she did it. Let’s go!

How Erin Made Her Way To Practicing Law

Like many future lawyers, Erin was smart with a creative streak. Many people told her those skills would be great in a legal career. She was also inspired by her father, who spent his nights in law school to make a jump into the business world. 

That was a unique view of what you can do with a law degree besides actually practicing law, and it inspired Erin to pursue law as a career. Even as early as high school, that was Erin’s “destination.” She took all the prelaw classes, and after college, she took the LSAT. After a move to Chicago, Erin returned to Michigan to attend law school in her home state.  

Although her grades weren’t the best, Erin had fun and law school and made a lot of friends. After graduation, she thought she would become a commercial litigator, working plaintiff-side class-action cases, and that’s precisely the job she got. 

It was as good as it was said to be, but there wasn’t a lot of work because of the recession. Eventually, they laid Erin off, and she spent the next two ad a half years unemployed, doing document reviews and volunteering for the Obama campaign. She even explored comedy as a possible career option. 

Then, in 2010, a Chicago firm started a staff tourney program, where many of Erin’s friends worked, so she applied. She applied for an in-house contract attorney position in a Biglaw firm. 

Let Down By Biglaw 

After ten years, that position turned out to be something entirely different. Essentially, Erin was let down by Biglaw. The firm that Erin was working at made a lot of changes, and those changes were a disappointment. She thought she would be a plaintiff-side class-action attorney, but she became an e-discovery counsel for a Biglaw firm. 

Erin thought practicing law in a Biglaw firm would stabilize her life while she found a way to get back to litigation. But over time, she found the legal industry tells you where to go, not the other way around. 

And because she was doing e-discovery and not litigation, it was hard for her to be taken seriously as a prospective litigator. After a few years, she spent more time working with technology and doing a lot of project management. And the more time she spent doing that, the harder it was to go back to litigation. 

And then, her job changed again. Although she was called a discovery counsel, Erin’s job shifted towards process creation and e-discovery. Her specialty became basically making discovery miracles happen. 

Erin hated her work as a discovery counsel and was always looking for a way out. For a while, she thought that her out would be writing comedy. But there just wasn’t enough passion for it to uproot her life to move to LA. 

Discovering A Career In Coaching

At the time, Erin was in a relationship with a man going through a contentious divorce. Even when he was agitated, Erin walked him through the litigation process. That’s when it dawned on her. She thought about becoming a coach for people going through the litigation process.

Although the relationship didn’t work out, the idea stuck. After a long time of trying to heal a broken heart, Erin realized there was no hope in it if she was unhappy with how she spent most of her time. She just didn’t want to be a discovery counsel anymore- or ever, really. 

So, that was the moment she decided that she needed a career change. After weeding out other options like becoming a therapist, Erin started looking into coaching training programs. She loved that coaching is future-oriented, creative, and creation-based, which appealed to her more than any other option.  

Erin spent the next ten months building her career in coaching while working as a discovery counsel. But, there was a tipping point where she couldn’t spare more time between developing a clientele and working a full-time job. She had also lost any spark she had for her work. 

The Struggle With The “Lawyer” Identity Entanglement 

One of Erin’s biggest struggles with leaving her job, even after being let down by Biglaw is one that is so present here at Former Lawyer. That is the struggle lawyers experience with being entangled in the lawyer identity. 

From not knowing what to do after leaving the law to not being to imagine life without practicing law, this struggle keeps lawyers in unhappy situations. Even after leaving the law, many keep quiet because it’s so hard to answer the question you could once answer with a simple, “I’m a lawyer.” Trying to explain that you used to be a lawyer, but now you do something else is too complex. 

Again, this is a common struggle. In Episode 20, Catherine Zack talked about the transition of explaining her career. She introduced herself as a former lawyer, didn’t mention practicing law at all, and now she’s back in the middle space. 

But, there’s also a lot of inner pushback against that feeling. The healthiest way to go about it is not to push it away but to exist with it. Erin still identifies as a lawyer. Even though she doesn’t practice law, she does work with lawyers, it exists within her life, and she is at peace with it. 

A Career in Coaching Executives 

Erin now works as an executive and life coach. Most of her clients come to her with career issues, but it’s really about who they are and what they want to have in their lives. 

She says that high-functioning executives and lawyers will mostly find ways to ask for help throughout their careers because that’s where they find the most value in themselves. What inevitably happens is that they start talking about what they want out of their career. 

The conversation soon shifts from that to the experience that they want to have in their life. The reason is that Erin’s an ontologically-trained coach, which means she can coach both what you’re doing and how you are about what you’re doing. 

Advice From An Executive & Life Coach

As an executive and life coach, Erin is always open to giving advice. Her wisdom for Former Lawyer listeners was to think about the framework you’re looking through. Are you looking at things in your lawyer framework or your new-life framework? Is it actually limiting, or are you seeing the whole landscape? 

Usually, when you think, “If I do this or this, then this or this will happen,” you’re limiting yourself. There’s an experience of freedom on the other side, where it doesn’t have that either-or heaviness. Just get out of that mindset, and have an open mind. 

If you want to learn more about Erin and how she helps lawyers make their way out of the law, check out her website or book a 30-minute conversation to see if her coaching style is a good fit for you. You can also join the Former Lawyer community to get the support and resources you need to leave the law for good!

Connect With Erin:




Sarah Cottrell: Hi, and welcome to The Former Lawyer Podcast. I'm your host, Sarah Cottrell. On this show, I interview former lawyers to hear their inspiring stories about how they left law behind to find careers and lives that they love. Let's get right to the show.

Hello everyone. This week on the podcast, I'm sharing my conversation with Erin Conlon. Erin graduated from law school and landed her dream job with a plaintiff-side class action firm only to lose her job as a result of the recession in the late 2000s. She worked in a political campaign, started performing comedy, and ultimately landed in Biglaw doing electronic-discovery work. She spent almost a decade as discovery council before making the leap to life and executive coaching. Erin describes herself as a recovering lawyer, comedian life and executive coach, and a warrior for possibility.

We'll get right to our conversation in just a minute but I wanted to take just a moment to talk with you about my small-group program because if you're listening to this episode the day that it comes out, enrollment for the group program is closing on Wednesday.

I know that there are people listening who are working as lawyers who aren't happy in their job and are thinking that they want to leave or maybe they want to leave but have all kinds of questions like “What am I supposed to do next? Isn't this just a huge waste of all the money and time that I've put into becoming a lawyer? How do I deal with the fact that I feel like my whole identity is wrapped up in being a lawyer?” and so much more. Not to mention the logistics and nuts and bolts questions that you might have.

This group program is designed to help you work through all of those things. You can check out to see more details about all that we're going to be covering. I really hope to see you in the group. I think that we're going to be able to do some great work together. Again, enrollment closes Wednesday so just a couple more days, Now, on to my conversation with Erin.

Hi, Erin. Welcome to the Former Lawyer Podcast.

Erin Conlon: Hi. Thanks for having me.

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

Erin Conlon: Yeah. I'm a former lawyer and now I'm an executive and life coach. I have my own private practice based out of Chicago. I also have been a comedian, a traveler, and all sorts of other fun things. That's the short version of me.

Sarah Cottrell: Let's go all the way back and talk about how you decided to go to law school in the first place.

Erin Conlon: Yeah. I don't know if this is true for you, but for me, I was a smart person who had a creative streak that people told me it would be great to be a lawyer because it would fit my skills and I would get to write. Even as early as high school, people were like, “Oh, you should go to law school,” and it just became that thing that I would probably end up doing.

I took all the pre-law classes and I graduated from college, took the LSAT, and then moved to Chicago for a year. I was like, “I'll find a job and that way, I won't have to go to law school.” Then I didn't. I grew up in Michigan and I went to Michigan for undergrad and then I was substitute teaching and working waitressing jobs and just being a 21-year-old in the city of Chicago. I ended up getting into Michigan and it was like, “Well, this is an amazing school and it probably will give me a really great future,” so onward I go, and that's how I ended up in law school.

Sarah Cottrell: Yeah. I think some variation of that story is extremely common amongst most of us who went to law school. I'm wondering if the people who told you that you should be a lawyer, were they lawyers or were they just people who thought they knew what a lawyer was?

Erin Conlon: Yes. Both, all of it. There's a certain level of success that generationally people expect. My family, my dad and mom were pharmacists. Then when I was really young, when I was eight, my dad went to law school at night for four years and so it was like his jump in the business world came because of law school. I think that idea from my dad and also what you could do with a law degree “afterwards” was the seed that just kept growing and kept growing and kept growing for my decision, oh, and money.

Sarah Cottrell: Yes. You said something like “What you can do with a law degree.” I'm fairly certain I know why you said that, but for anyone who's listening who might not be totally sure what you mean by that, can you just explain why you put it that particular way?

Erin Conlon: Oh, because around the time that I went to law school and before, people would be like, “You can do anything with a law degree,” and it had some weight to it prior to the recession, or at least it seemed to, I don't believe that's necessarily true now.

Sarah Cottrell: One of the things that I often say to people is there are lots of people doing lots of things with law degrees which is not exactly the same thing as you can do anything with a law degree, which I know we've unpacked that on the show a couple of times, but let's get back to your story and talk about you get to law school, it sounds like you were in this like, “Well, I got into a good school and not really sure exactly what I would do otherwise, so I'm going to go.” When you got there, were you like, “Wow, this was a great life choice,” or “Wow, this was a terrible life choice,” or just somewhere in between?

Erin Conlon: I was totally in the in-between. I really liked the people I went to school with. I had a lot of fun being in school and school was natural to me. I was not the best law student though, it just wasn't my best three years of academic performance.

Sarah Cottrell: When you got to the end of law school, what were you thinking about what your future would be after you graduated?

Erin Conlon: Well, what I thought is that I would go be a commercial litigator and do plaintiff-side class action stuff. That's the job that I got right out of law school. It was really cool that who I thought I would be, I would get to be, and then there just wasn't a lot of work at the firm for me. I was 25 and I didn't know how to create my own cases or that they expected that of me. I didn't really get it, so partly my fault, partly they didn't have the work. I got laid off right at the beginning of the recession.

When I got laid off at the beginning of the recession, the law firms were still doing fairly okay but they weren't hiring anybody. I spent two and a half years unemployed or underemployed doing document review and volunteering for the Obama campaign. That's how I got started in comedy and all of that other stuff. That was the first three years of my legal career.

Then sometime in 2010, one of the firms in Chicago started a staff attorney program and I had a lot of friends that worked at this firm so I ended up applying for this job that was intended to be an in-house contract attorney more or less and turned out to be, after 10 years, something entirely different. That's what my legal career was in that. I went from commercial litigation to electronic discovery, which was a big disappointment for me.

Sarah Cottrell: I want to go back and talk about the comedy piece, but first I want to just talk a little bit more about what you said over the 10 years, that it changed quite a bit. Are you just referring to the fact that you went from doing the plaintiff-side work that you had imagined to the e-discovery piece, or do you mean specifically at the firm where you took the staff attorney position?

Erin Conlon: I mean specifically at the firm where I took the staff attorney position.

Sarah Cottrell: Okay, so tell me a little bit more about what happened there and what changes you saw over the time that you were there.

Erin Conlon: Well, the firm itself never pretended that this job would be anything other than what it was. The disappointment, just to be clear, was on my end because I thought I would be this plaintiff-side class action attorney and then becoming an e-discovery attorney for a huge law firm, two totally different career paths. I thought that the big firm job would be a nice way to stabilize my life and then find a way to get back to what I was doing.

What I found was that the legal industry had decided that that's what I wanted to do and because I had been doing discovery and not the whole spectrum of litigation, it was really hard for me to get interviews or be taken seriously as somebody who intended to and wanted to be a litigator. Then after a few years, I was spending a lot of time working with technology and doing a lot of project management.

In that project management realm, it was less of legal skills and more of business skills and just basic non-legal stuff. The more time I spent at that job, the harder it became to go back to what I wanted to go to. I think that's fairly natural. If you're 22 and you decide you want to do something and then it gets taken away from you, then you do whatever you can to fight to get it back. I think that was a mistake for me. I probably could have just accepted what was and built upon it in a different way so that I didn't carry through some of this, “Oh, I have to fix this feeling.”

Sarah Cottrell: Yes. I think that is such a good insight and it's definitely something that I've heard or observed from a lot of other lawyers which is it's very easy, especially if you went to law school straight out of undergrad or close to when you graduated from undergrad, to have this idea in your mind of what you want to do or “should” be doing as a lawyer and then go for literally years and years and years basically pursuing that goal without necessarily thinking about “Is that really what I want to be doing now given my life circumstances?”

I think there's almost this sense of “Oh, well, if I change my mind, readjust, or my priorities shift because of my life circumstances, I'm somehow ‘giving up’ on myself,” is that what you're talking about?

Erin Conlon: Well, I think in part there's a little bit of that “Oh, I would have given up on myself,” and then the other part of it, the e-discovery world, in the legal world, is not necessarily looked at as real lawyers, we're service providers and so there was a huge part of me that was like, “Take me seriously as a lawyer” that I had a really hard time giving up.

Sarah Cottrell: Which I think is totally understandable. It's so interesting because especially if you're working at a big firm like a big firm doing litigation, e-discovery has a huge role to play. Your case is not actually going to end up going to trial, it's eventually going to settle.

You were talking about, for example, the project management that you were doing and those types of things. I think increasingly, that is the work that lawyers are doing, at least when you're talking about very large cases that are being handled by larger firms, and so it's a little bit strange that there is this attitude about e-discovery work. Where do you think that comes from?

Erin Conlon: Well, I went to law school 15 years ago so I think—and I don't know if this is true now—but I think a lot of it is that the way I was taught was that discovery was a thing you had to do in order to get to the arguments and it wasn't a practical conversation. What we're talking about is the reality of how the law is practiced, especially in the Biglaw world where you have to have a certain budget in order to even consider going to litigation. That budget is going to include data management and everyone's going to try and squeeze that budget.

Sarah Cottrell: Yes, 100%. Oh, my goodness. So many thoughts. You're at this large firm in this staff attorney role, is that the role that you just left or did you go to another lawyer role after that? Talk to me about at what point you start to think “Hey, maybe I don't want to be doing this lawyer thing anymore.”

Erin Conlon: The job I left is not the job I started. I had a different title and it was an entirely different job. The title I ended with was discovery counsel but it was at the same firm and the shift was a lot more towards actually creating the process, using the technology, and being the go-to person for all discovery needs for all of these massive litigation cases, and sometimes FTC or DOJ, antitrust investigations, second requests, or whatever.

But any time that there was a massive amount of information that needed to be collected in a short amount of time and then produced, that was more or less my specialty. It's like making miracles happen in the discovery world. Seriously, before I left the firm—and this was one of the things that made me decide it was time to leave—let me just back up real quick, I had never wanted to do this work and so I had always been looking for outs.

For a while I thought that comedy would be my out, that I would move to LA, be a comedy writer, and go find good on that path. There was something about that path that wasn't enough to make me want to throw up my life and say “F*ck it, let's go.” I was in Chicago and I had been working, doing comedy, and dating. I was in a relationship with a man who was going through a divorce and it was a contentious divorce.

We talked a lot about the litigation process. He would get upset about something, I would be like, “Dude, it's just the process. Chill.” One day I was standing in his kitchen and I was like, “I should be a coach for people who are going through litigation, just be available to talk them through some of this stuff that is not what lawyers talk to their clients about but is super important for clients to know.” He was like, “You should.”

I just got goosebumps and I was like, “Okay.” Then he and I broke up and it really hurt a lot. I spent a lot of time trying to feel better. I went to South Africa. I bought a motorcycle. I learned to paint. I did all of this stuff to try and feel better in the moment. I was sitting on my deck one day and I had this realization like, “Oh, I am not going to find a way to feel better because I don't like how I'm spending 50 hours a week, if not more. I just don't like it. Nothing that I do on the outside will make me feel better unless I find a way to enjoy my life more.”

So I decided that I needed to change careers and I looked into becoming a counselor or a therapist. There's something about that path for me that one, it was really expensive and the opportunity cost was really a lot, especially since at the time I was in my mid-30s and I didn't want to lose five years of income to go back to school because I'm also single so this is all me all the time.

I started looking at the coach's training programs. The thing that I loved about coaching was that it was future-oriented and creative, creation-based. That appealed to me more than healing, probably because of my creative streak anyway. So I joined a coach's training program, I got trained, and now here I am, training other coaches and I have my own coaching practice. I diverted from something I can’t remember what it was.

Sarah Cottrell: I was just asking where in that 10-year process you started to think, “Hey, maybe I don't want to be a lawyer.” The whole time. When you started coaching, were you still working that job or did you leave that job and then start coaching? How did you make that transition?

Erin Conlon: I did the training program. Coaches don't get degrees, there's no degree to be a coach the way there is for a law degree, therapy, or whatever. It's a self-regulated profession. Most of the coaches that I work with regulate themselves with the ICF which is the International Coaches Federation. I decided that I needed an ICF accredited training program, that it needed to be in-person, that I didn't want to spend a lot of money to travel to go to it, and it had to be rigorous but also teach you how to build a business. That's how I ended up with accomplishment coaching because they had all of those requirements like my personal requirements.

As I was getting trained, I was still working my job and building my business. Then I spent another 10 months building my business while I was still at the firm. Then I realized that there was a tipping point where I just couldn't spend the time I needed to develop my client pipeline and work full-time at this job, and more importantly, I had a couple of big moments where I was like, “I can't do this anymore.”

Maybe four, three weeks before I quit, two weeks before I quit, I managed the process of having people in our firm review and produce over 600,000 text and MMS messages in four days which is insane that that got done in that short amount of time. It is miraculously insane and everyone was like, “Oh, my god. This is so amazing.” I was like, “Yeah. This is great.” I don't have any joy from this. It doesn't feel as joyful to me as it did when one of my clients had a successful first date, it just didn't hit me in the same way.

Then I went on a retreat with some other coaches and I was getting coffee for them. We went to Starbucks and I was like, “Oh, I would rather be a glorified intern getting coffee with other coaches than play this game of being a lawyer anymore.” I couldn't do it so I went back to Chicago after that retreat and I quit my job.

Sarah Cottrell: I love that. Honestly, when you're talking about that, even though I didn't have that exact experience, I feel it in my soul, but for sure there would be many lawyers who would hear that and just not be able to connect with it at all. Why do you think that is?

Erin Conlon: Well, I don't know if this is true for you but for me, there was a lot of value in the identity of being a lawyer, the ego, and the instant validity that other people gave me. It took a lot of internal work to be able to even consider breaking that up.

Sarah Cottrell: Yes, 100%. I know we've talked about that on the podcast multiple times but I think that is a huge part of what holds people in the law even if they aren't happy there. What keeps people from even being willing to see that they're not happy is that identity piece feeling like basically, to leave the law would be to leave themselves. They don't know who they are apart from the identity that they get from being a lawyer. To be clear, I'm not saying those people have such issues. This was an issue that I worked through myself so I completely agree.

Erin Conlon: Yeah, and I don't know about you but I still identify as a lawyer.

Sarah Cottrell: Yeah. It's a little bit tricky because now I'm doing for example this podcast and so I still identify as a lawyer, but I guess very strongly as I used to be a lawyer. We just recently moved to a different city and that's been a really interesting experience for me because I practiced as a lawyer for over 10 years and so you meet new people, one of the first couple of things that comes up is “What do you do?” and everyone knows what a lawyer is so it's a very easy straightforward conversation, I don't have that anymore. I'm not unhappy about it but it is much more complex.

Erin Conlon: Yeah. I just had this, I don't know if this is your experience, but one of the things that I've noticed about lawyers is that we like to have the answer and so when somebody asks us what we do and you're like “I'm a lawyer,” you have this very easy simple answer that other people will make inferences from. It doesn't matter if they're right or wrong, the tapestry is more or less understood. When you're like, “Well, I was a lawyer and now I’m a…” people have to work a little bit harder to understand you, which is not that I think lawyers and former lawyers are used to swimming in.

Sarah Cottrell: Yes. I think that is 100% correct.

Hey, it's me again popping in one last time to remind you that my group program is closing enrollment on Wednesday, February the 12th. So if you are someone who hates your lawyer job and you're ready to get out, in these eight weeks, we're going to work through some of the biggest obstacles to leaving the law including who you are outside of being a lawyer, what you want to do next, and how to figure these things out even if you have no idea.

I realize many of you may have no idea because I've been there and that was my experience. If you're not totally sure that you want out but you're sure you need to make some change, the program, although it's primarily geared towards people who want out of the law, will also work really well for people who are wanting to try to figure out their next steps outside of the law or inside of it. If you're interested and you haven't yet signed up, you can go to, get all the information, and enroll to secure your place. I hope to see you in the group, Okay, back to the episode.

Sarah Cottrell: When you say that you still identify as a lawyer, what do you mean by that?

Erin Conlon: I think I'll always be a lawyer. It so happens that a bunch of my clients are currently lawyers and I think it's because, one, if somebody gets to the point where they want to hire an executive coach or a life coach, they want somebody who gets them, and lawyers get other lawyers. It's part of this rosetta stone of what life is like so I think there's that piece for who my client base currently is.

Then the other piece of it is that I went to law school, I practiced law for almost 15 years, it's the same thing as me being a comedian. I don't currently do a lot of stand up but I will probably always call myself a comedian because I have that skill set. I know how to do it. If somebody put me on stage with a microphone, I could probably entertain people for a solid 10 minutes in the same way that if somebody calls me up and they're like, “Hey, I have this thing with my neighbor,” I could probably give them more or less reliable advice. I just don't think it's something that will ever disappear completely from me. It's just not all of me or only me.

Sarah Cottrell: Yeah. An episode that released a couple of weeks ago was an episode with Catherine Zack. She left the law to teach yoga and meditation. One of the things that we talked about was this idea of your identity as a lawyer and she talked about how, when she first left, she was constantly introducing herself like, “Oh, I used to be a lawyer and then blah-blah-blah.”

Then she got away from that to the point where she was not even mentioning or talking at all about the fact that she had been a lawyer and now has moved back into more of a middle space again, which I think is really interesting. I think it's been really true for my experience. In some ways, there's this holding on to the idea of being a lawyer because, like you said, there's some element of it being wrapped up in your identity. But then there's almost like the inverse of pushing it away and reacting against it.

But I think that probably the healthiest place is what you're describing where it becomes a part of who you are, it's a part of your story, it's a part of what you bring to whatever you do after you leave the law, but it's not this thing that you're reacting against, either pulling super close to you even though you've left, or pushing it away. You're able to exist with it and not have it affect so much how you present yourself or how you think about yourself.

Erin Conlon: Yeah. I think that the denying part of it is part of the process. You have to get into this “Who can I be if I am not what I was?” You don't have to, but I think that there is value in going through that entire process of the push-pull. It just so happens that I picked a profession where that process happens way faster because it's intentional for me to integrate all areas of my identity and my life.

Sarah Cottrell: Let's talk a little bit more about your business and the type of coaching that you do. I know you mentioned the idea of coaching people through litigation but it sounds like, from what you've described, what you're doing is a little bit broader than that. What type of coaching are you doing? What types of clients do you typically see? Just tell me a little bit about that.

Erin Conlon: Yeah. I am more or less a life coach who works with executives. People who come to me come to me a lot of times because they have a career issue, but really it's mostly about who they are in their lives and what they want to have in their life.

With people who are high-functioning executives and lawyers, the way that they can ask for help or think about their lives is through their careers because that's where they find a lot of value for themselves. That's where they've put a lot of energy and focus for themselves. What inevitably happens is that we start talking about what they want out of their career. The conversation shifts from that to the experience that they want to have in their life.

The reason the conversation shifts is because I'm an ontologically-trained coach which means I coach both to what you're doing and to how you are about what you're doing because, Sarah, if you decided that you wanted to turn this Former Lawyer Podcast into a television show, you could probably do that and you could do it one of two ways.

You could do it the “I'm going to get this done because I said I would get it done” way or you could do it from the “Oh, this is so creative and amazing. I can't believe I get to have this experience. Look at what we're all doing together” way, and it's the same outcome but it's an entirely different experience in the process. That's really what coaching with me is like.

Sarah Cottrell: I think it's so true to what you're saying about, in particular, high-achieving people and career. I would say it's socially acceptable to express certain types of dissatisfaction so like, “Oh, I want to achieve more in my career,” or “Something's missing from my career path,” that I think is a lot easier for people to admit or even realize, have that thought, than “I think there's something missing from my life or my life is not what I want it to be.”

But like you said—and I know we've talked about this in the podcast before—your job is not just your job, and the way you think about your career is not just compartmentalized to your career. It's the thing that you spend a lot of hours on every week and it touches everything.

I think it's super common, like you said, that people go into something with the intent of working on the career piece, and in reality, what they're really wanting to do or needing to do is some inner work, some work on what they want their life to look like.

Erin Conlon: What's so funny is for the longest time, I looked around at my life and I was like, “Oh, my life looks exactly the same. I'm going to the same job. I have the same hobbies. I'm still dating similar people,” but my experience in 12 months of my life had shifted from a victim state of “Ugh! This is happening to me” to “Oh, this is what I'm doing. I'm choosing this. Here are my choices and here are my choices resulting.” That experience of having my life look the same but be totally different is I think the dissatisfaction that people don't know how to fix or even address.

Sarah Cottrell: Yes. Actually, the episode that released this week, the podcast episode was with Sam Vander Wielen. She talked about this exact thing, how she felt like she very much was in this what she described as a victim mentality, and would express things about basically how her job as a lawyer, what she did not like was happening to her. She had an experience of someone telling her that she was choosing it and was very upset.

Then she says now as she looks back on that, she realizes that was much more true than she was willing to admit at the time. I am not trying to downplay the various factors that people have to consider when they're looking at what they are doing with their career but I think sometimes we need help having an imagination for what is possible. It sounds like that's part of what you do with your clients.

Erin Conlon: Oh, that's the bread and butter of what I do because generally, the people who relate to me and who want to work with me are all probability masters, they know what's probable, they know what they can probably do, and they've been living in that realm of “Yeah, I could get that done” for their whole lives. But what they're not talking about is what they really want and how to do it without disappointing their family or their spouses, changing their total identity, or any of those things. This “what is possible” piece is the most fun place I have ever lived in my entire life.

Sarah Cottrell: Yeah. I think sometimes just realizing there are all these possibilities even if you end up doing more or less the “same” thing, at least from the outside, can fundamentally change how you approach everything. I know I've mentioned this in the podcast before but even with doing this podcast and having to learn various things like sound editing, whatever, which I had never done a day in my life previously, I had this like “Oh, I can still learn really different things from what I've ever done before. I think living into the possibility helps you see even more possibility.

Erin Conlon: Yeah, it's a compounding effect.

Sarah Cottrell: Yes, for sure. Let's go back, I know this was forever ago, but talk to me about how you got into comedy and that whole experience because I am definitely not a comedian so I am super interested to know more.

Erin Conlon: What's so funny, when I lost my job back in 2007 and 2008, I was just really depressed, because that shook up my identity, it was the first big thing to happen to me as an adult, it was my first real adult job so I became a huge victim to that and also got succumbed into what it meant about me.

In that process, there was one day where I was unemployed, probably watching TV, and I had this realization like, “Oh, people write these shows. Scrubs does not just magically show up on my TV. Somebody writes it. That would be a fun way to live making people laugh. Who wouldn't want to do that?”

I happen to live in one of the greatest comedy cities that has ever existed and so I started taking comedy-writing classes and I did that for a couple of years, put on some stage sketch shows here in the city. Then I was starting to get into pilot writing and script writing. The person that I was learning from unexpectedly passed away, so that really threw me. I was like, “I don't know what to do.”

That got me into improv and performing because I just didn't have the heart to sit down and write anymore so I did performing for a couple of years. Then I realized I really, really hated performing improv because it was a lot of acting and I don't like acting. I'm not good at it. I have a very hard time not being me. That's how I got into stand-up. That's one of my major hobbies, stand-up comedy. That's how I did it.

Sarah Cottrell: Do you still live in Chicago? I guess you said that you aren't necessarily doing a ton of comedy-writing now.

Erin Conlon: Yeah. I do live in Chicago and I was running an open mic up until last April. I got to the point where I was like, “This is not working for me anymore.” It was just a lot of work and it felt like a huge drain because at the same time, I was still working full-time as a lawyer, still exercising regularly, trying to eat healthy, keep my sh*t together, and also build a business.

Sarah Cottrell: Just a few things.

Erin Conlon: It’s just a few things. Just like 15 million things. I was like, “I'm just going to let this go for a little while.” I intend to go back to doing it in some way. I have an idea for a pilot that I think will be amazing, so that is one of my 2020 plans is to write this pilot and get back into my creative life in a different way.

Sarah Cottrell: I love that. I think one of the hardest things to learn as a human, but generally it's something people don't learn until sometime in adulthood, at least fully, is that we have limits. Even if there are lots of good things that you want to do, you can't necessarily do every single one of those things. No matter how much you want to do them, we are finite.

I think that is especially for people who were lawyers or had that high-achieving or school-grades focused sort of personality. I think that's a really difficult lesson to learn. I know for me it's been one of the most valuable, and I know this is so cliche and people say it all the time, but the idea that saying yes to something, one thing is saying no to another thing, I think that's something that is particularly hard for certain lawyer-personality types to accept. I speak from experience.

Erin Conlon: That just reminded me of something that one of the first partners I ever worked with told me. She said that the reward of being a good lawyer is like winning a pie-eating contest and getting more pie. To your point, saying no to something is, at least for me, like saying “I can't win this pie-eating contest,” and I never want to say that.

Sarah Cottrell: Yes, which goes back to something we talk about on the podcast all the time, which is that some things that we think are just surfacy like, “Oh, I don't necessarily like my job,” or “I'm not totally happy with it,” or whatever, what we've talked about earlier, are so often connected to so many things, so many deeper things in our personality.

Erin Conlon: One of the things that as a coach I get the experience of is a little bit of elevation from “personality traits.” Sometimes it's just as simple as, “Oh, these are the glasses that I'm wearing and I'm looking through it through this particular evaluative lens.”

Those skills that we learn as lawyers then become ingrained or like the snake that eats its tail, because you're good at this, then you go into being a lawyer, which means that you become more good at it, which means it becomes who you are, and it's really hard to break up what is more or less like it doesn't have to go that way. Did that make any sense?

Sarah Cottrell: Yes, it totally makes sense. I think it's so true. Erin, as we're getting towards the end of our conversation, is there anything else from your story that you would like to share that we haven't touched on yet or any advice that you have for people who are listening who are lawyers and don't want to be?

Erin Conlon: That was a compound question so I'm like, “Where do I start?” I think the thing that I have in terms of advice or big realizations for people who are considering not being lawyers or just aren't lawyers anymore, but I'm assuming if people are listening to this podcast, it's because they have something to relate to and want something to build upon.

I don't think that I have all the answers, but the advice that I have is just consider what framework you're looking at things through. Is this your lawyer framework or is it your new life? Is it actually limiting or are you seeing the whole landscape? Because my guess is when we have a feeling of “If I do this or this, then this or this will happen,” you're limiting yourself and there's an experience of freedom on the other side of really choosing possibility where it doesn't have that either-or heaviness.

Sarah Cottrell: I think that is so, so good, so true, and just really good advice. As we're wrapping up, I'd love to know where people can find you online if they're interested in connecting with you.

Erin Conlon: Oh, yeah. Just go to my website at The cool thing about my website is that you can book a 30-minute conversation with me just to talk about what's going on in your life and there's no charge to it. It's just a way to see if maybe we could be a match, if what you need is coaching, or if you just want to learn more about what it means to become a coach. I'm happy to have all of those conversations. Also, I just really love talking to smart capable people who are interested in possibility in what's next for them.

Sarah Cottrell: That is great. I will put that link in the show notes. For people who are listening, if you didn't catch it, you can always just head to the website and it will be at the bottom of the episode page so that you can find Erin and connect with her. Thank you so much, Erin, for sharing your story. I think we talked about some really important things and it was great to get to know more about you and what you're doing in the world.

Erin Conlon: I love that you have this podcast. Sarah, thanks for having me and also thanks for introducing possibility to an audience that might not live there all the time. You guys, I'm not really trashing lawyers.

Sarah Cottrell: No, yes, 100% where this podcast grew from was me working as a lawyer thinking “I need something like this. Where is this? Because I need a podcast and this is what I want to hear because I need help developing an imagination about what's possible.” So I really appreciate that because that is where this all grew from.

Erin Conlon: Yeah, it's so cool. It's like the informational interview process for a bunch of potential non-lawyers.

Sarah Cottrell: Yes. I'm like, “Here, people, hear these stories.” Thanks so much for coming on.

Erin Conlon: Thanks for having me.

Sarah Cottrell: Thanks so much for listening today. I absolutely love getting to share these stories with you. If you haven't yet, subscribe to the show, and come on over to and join our community to get even more support and resources in your journey out of the law. Until next time. Have a great week.