Transitioning From a Legal Career: The Former Lawyer Story Part 2 (TFLP 101)

For those who may be new, Former Lawyer is run by me, Sarah Cottrell. Through my work with Former Lawyer, I help those that are trying to transition from a legal career and into something that’s really meaningful for them. This is part two of the story of my journey transitioning from a legal career and into starting Former Lawyer, as interviewed by Jessica Medina.

For more information on the first part of the conversation, click here

Transitioning From A Legal Career

In 2018, after having my second child and coming to grips with who I may be if not a lawyer, I decided to transition from a legal career for good. I said, “I’ll give myself a year,” and made a promise to myself to focus on getting through the first year of being a mom to two children.

While having a second child made the decision of transitioning from a legal career easier, giving myself a full year was an overestimation of my restraint to keep busy! I started exploring options, including writing and eventually considered starting a podcast.

Originally, the podcast started as a hobby. But then people came to me constantly asking more questions and wanting more information about how to transition from a legal career. My vision became that I wanted to provide a place for these individuals where they would not only have someone who felt similar things, but also some new options about what the next steps could be.

Creating Former Lawyer LLC

By July 2019, I had already done the first handful of interviews for the podcast and was getting ready for its debut. During this process, I found a new business coach that helped me to scale my online business and create a workshop. 

This new business coach put a heavy emphasis on me connecting with my target audience and making the business model a true service to others. I worked on that and in time, the podcast got bigger and bigger, eventually transforming into a multi-platform business to help people to transition from a legal career.

Then, in early 2020, I ran an eight-week program for transitioning lawyers, with many of the same questions others had been asking me and what I asked my guests on the podcast. Something sparked with this program and I decided to create The Former Lawyer Collaborative.  

Working With The Collaborative

I truly believe that you have to do internal work to find the right career path for you. You have to go deeper into yourself to find your values, your genuine passions. I created The Collaborative as a place to guide you through that process and realizing that you really aren’t alone.

There are so many others that are feeling the same things you are. It’s a great support network and how-to guide for leaving the law. It starts with the basic questions of how you became a lawyer and what you like and dislike about it. Afterward, it moves into deeper questions surrounding your personality, values, and interests.

For example, if you were interested in becoming a recruiter, the framework would involve questions like: What is the life of a recruiter like? Is it something that would fit well with your personality? After that, you will move into working on tailoring your resume to your interests.

It’s a space for all of us, in the law or transitioned out, to connect, commiserate, and learn from each other. 

What You Can Gain With Former Lawyer

I created Former Lawyer to show you that you’re not alone in leaving the law. Having a network of like-minded people, like with The Collaborative, is greatly beneficial to helping you transition from your legal career.

There’s nothing wrong with you or the way you work. When you can see that others are struggling with the same issues, you realize it isn’t you at all. It’s the combination of you and the system you’re in.

When you have this realization, Former Lawyer helps you to find the right system for you through their many facets including a weekly Podcast and Blog,  YouTube Channel, and The Collaborative Group Program.

My Advice To Future Former Lawyers

My transition from lawyer to entrepreneur did not come without its own obstacles. I’m very transparent in what I still struggle with today, including withholding my perfectionism, accepting that we are all limited and that taking action is the only thing that truly matters.

Here is some advice that I like to give for people that are just starting to approach the idea of leaving the law:

When you’re leaving the law, there will be a lot of doubt in yourself and what you can do. It’s not just about finding something you’re good at. It’s finding something that really fits your personality and values. Choose something that you’re truly passionate about, otherwise, you’ll never be happy.

Additionally, you will need to realize that the world beyond law is imperfect. It’s the complete opposite of your past career, and you will have to relearn a lot of things like acceptance, learning from failures, and always trying new things. 

How To Start Your Transition From A Legal Career

If my story or the stories of others here in Former Lawyer have you thinking about leaving the law or you’re new around here, start with my free guide: “First Steps to Leaving The Law”.  These are carefully crafted steps for those who are looking to leave the legal field or are still undecided and would like a good look at what it would be like. 

You can also subscribe to the email list, where you get more tips and advice from me, and if you have any questions, I will actually connect with you and answer all of your questions. 

Remember that only you have the right answers for you, but Former Lawyer is here to help you find those answers and to support you through your transition from a legal career. 


Mentioned In This Blog:

The Former Lawyer Collaborative

First Steps to Leaving The Law

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, I'm sharing the second half of my conversation with Jessica Medina—or I guess I should say the second half of the interview that Jessica Medina did of me about my experience of becoming a lawyer and leaving law. Again, I just want to remind you that Jessica was on the podcast previously. If you want to hear more about her story, you can listen to Episodes 59 and 60.

Last week, we talked a lot about the internal work that has happened for me as I was moving through the process of becoming a lawyer and then realizing I didn't like it, and also how I ended up being a lawyer. In this half of the conversation, we talk more about the process of me actually becoming a former lawyer, and then of course, the creation of the business that is Former Lawyer LLC. I had such a good time talking with Jessica about all of this stuff and just reflecting on the things that I've been able to do with Former Lawyer. I'm really excited for the next hundred episodes and I hope you enjoy this last bit of my conversation with Jessica.

Jessica Medina: Okay, so you had done all this internal work, so making the decision in 2018 to not go back to what was basically, for all intents and purposes, the dream lawyer job for Sarah—which I think is such a great test of whether you actually want to be a lawyer, if you don't like your dream lawyer job, it's probably the law that you don't like and I hear that. It comes up a lot because that's what it takes to get us out of our rut—What was your first day like, I guess you were going to be a new mom again so maybe that was part of it but tell us about what you got into, did you start something right away? Was it weird not having this thing that you've been doing for 10 years still as part of your daily thoughts? Tell us a little bit about those immediate days, weeks, and months right after your transition-out.

Sarah Cottrell: I think the fact that I was leaving because I was having a baby was it made it feel, I don't want to say made it easier, and again, for me, that first year of my kids’ life, with both of my kids has just been like I just need to make it through. Even if I had been returning to my job, I would have been out for some weeks of maternity leave and also, my husband at the time still works at a large law firm that has a great family leave policy and he took 12 weeks of leave and so I literally cannot overstate how helpful that was in terms of making it through the early month. I had told myself, “Okay, I'm going to give myself a year.” Our youngest was born in July of 2018 so I was like, “Okay, I'm going to just do what I need to do to make it through this year. I'm not going to think about what's specifically next until July of 2019,” which probably was an overestimation of my ability to restrain myself from doing things.

Around the spring of 2018, so April, May, maybe even March, I mentioned I'd had this idea for the podcast years and years before and I started thinking about, “Okay, I think I actually want to do that.” I also started doing some writing, as I said it's something that I like to do, not in the legal arena, more in faith, mental health, body image realm, which we didn't touch on this but in high school, I had an undiagnosed anorexia and so that's also been a big part of my story related to my clinical anxiety. Anyway, I started doing writing like that and I had a piece published in the spring of that year and then I was also working on the podcast. It sounds ridiculous now but it was just like, “Oh, I'm just going to start doing some things.” You don't start a weekly podcast just on a whim. It wasn't that it was on a whim but I backed into the whole thing in like, “Oh, I'm just going to do this,” and then it was like, “Oh, I'm running a weekly podcast,” and all of these people are coming to me wanting help or more advice, like, “What can I do to provide that?” and all of a sudden I'm running an online business part-time because running a weekly podcast is a lot of work.

For me, in the beginning, the whole first year of the podcast, which was August 2019 to August 2020, I did literally everything myself. I learned how to edit audio, I learned how to make graphics, all of the things that need to happen in order for that to occur, I did all those things. It makes me laugh now just to look back because I feel like at the time, I know for sure I had no idea what I was getting into but basically, what that means is by July of 2019, I'd already done the first five or six interviews for the podcast. I was in the process of getting them ready to release and I was just doing all of the various Former Lawyer stuff. I was also doing some writing and I actually have had to put down that non-related to Former Lawyer writing for a time because I still work part-time. I'm with my kids the rest of the time and there's only so many things that can happen in three days a week of work. I think that answers your question.

Jessica Medina: So you got right into something, something that was much bigger than you ever anticipated and it just got bigger from there. Yes, we are on the podcast right now but this is only one piece of all the things that you offer. Give us the high level, quick chronology of Former Lawyer. It started with a podcast, it has so many different pieces, now you provide so many services, but just for people who are thinking about, I think especially transitioning from the legal profession, which is very structured and it's very easy to see what's around the corner, online business, service-oriented businesses, and all the space that you're in, is I think very different from practice of law.

Sarah Cottrell: Oh, my goodness. Yes, you know. Being a lawyer is the opposite of “just do things and see if they work” and really so much of online business is you just have to do things and see if they work, iterate, and be willing to just fail and be like, “Okay, let's try something else,” and that is so contrary to one, everything you are taught to do as a lawyer and two, my personality, which I think is the personality of many, many lawyers which is very risk-averse, very perfectionistic, so it's been extremely good for me and for my personality because it has forced me to develop some underdeveloped parts of my personality and just myself.

The podcast started and I was like, “I know I want to provide something for people but I don't really know what it is,” well let me backup, actually, even from the time that I originally thought of the podcast, my husband and I were having these conversations where we were talking about the podcast, The Former Lawyer Podcast, and how helpful that would be. We also talked about how lonely the experience can be as a lawyer when you really sincerely are like, “No, I don't actually want to do this,” because so many people complain about their jobs—and I'm not saying there's anything wrong with complaining about your job to be clear—but not everyone is actually in that place where they're ready to do something about it. Bizarrely, even though we know so many lawyers dislike their jobs, people still feel like, “Oh, I don't like my job. There must be something wrong with me,” or “I don't like being a lawyer and I don't know what I would do next. Am I the only one?” That was something that I was very, very much experiencing in those early years.

We had these conversations about how wouldn't it be great for there to be a place where people who feel this way, who are genuinely like “I really do actually want to do something else,” could talk to other lawyers who are in the same place so that they would know that they're not alone and get information about what other careers actually look so you're not just scrolling the job boards, hoping that something would show up? Anyway, this is a conversation that had grown up at the same time that the idea for the podcast had grown up.

My very first business coaches, I talked about this idea with them and basically they said, “Oh, I don't think that will work.” To be fair to them, this is a very early baby stage in terms of the details. Because I was so new to online business and because I was still in the process of really learning to trust that I did know my audience, I did know lawyers, and let's be real, I think we can all agree, we know that we're weird and squirrely in certain ways, not just that but as a lawyer or having had that experience of working as a lawyer for 10 years, I really did understand what people really needed, and I think sometimes—and Jessica, I know you've probably had this experience too—but some of the mainstream online business advice is not helpful when it comes to lawyers, and I completely understand this because I'm the same way, lawyers are very skeptical, they are very risk-averse. If you're telling them things about a program that you have or whatever, there's going to be some sense of “But are you trying to rip me off?” or whatever.

Anyway, all of that to say, I set that whole idea that had grown up with the idea for the podcast back in 2011 aside because I was like, “Oh, well they say that it won't work,” even though I think in my heart of hearts, that because that's what I had wanted or felt would have been helpful for me, it was what I wanted to create but I was like, “Oh, I guess that won't work,” so we'll circle back around to that. Anyway, the podcast was chugging along and then in very early 2020, I ran a small group program where I worked with people for eight weeks and we worked through a lot of these questions that we've talked about and then some practical stuff like “how do I rework my resume so that it's not so legal and that it's more targeted towards the specific types of jobs that I'm interested in?”

We did all those things, but during that process, I had found a different business coach who had helped me understand the framework of how to run a small group program. Jessica and I both work with her, her name is Steph Crowder, and she's wonderful. One of the things that I really, really liked about her, specifically was that she really emphasizes and focuses on like, “You need to talk to the people you want to help,” and also, she focuses a lot on your business model being something that serves the people, who you want to help, which for me was very important because—and I know, Jessica, you've experienced this too—but there's a lot of online businessy stuff that's very like, “Do this thing and these funnels and these whatever,” and just stuff that is very not at all aligned with the way that I want to do business. Frankly, even if I did want to do business that way, I don't think it would be something that would be appealing to lawyers.

All that to say, I started talking with people just like, “Hey, I'm doing this small group program but here are some other things that I’ve considered. What would be helpful to you?” Out of that, essentially people kept coming back to something what I had originally first wanted to create that I had set aside. That for me was like, “Okay, this is what I really want to do because this is what I think will really be helpful,” and basically, people are telling me that is what they want. Why don't I just try it? If people aren't into it, then that's cool, but I won't know unless I try. You can see some of the evolution from the lawyer brain to the entrepreneur brain of one, being able to trust my own gut more and two, just be willing to try it and see how it goes.

April 2020 actually, I betaed The Collaborative, and at that point, it was specifically for women lawyers who were in somewhat similar positions to where I had been in my practice. It just grew from there. I had 18 people join that beta and then I opened it up to just lawyers in general in the summer once I'd had a little bit of time to build out the internal structure. One of the things that was really helpful about that is, you're mentioning structure, people having some idea of where they're going. Working with that initial group helped me to refine how to articulate some of those things that I had walked through in terms of the process to end up where I had ended up ultimately. That now is a framework called The Former Lawyer Framework—I know, very creative—and it's five stages and it walks people through all of this stuff that I talked about from “How did you end up in this job as a lawyer? Why? What is it that you like about it? What is it that you don't like about it?”

Then moving into things like, “What are your values? What do you like? What is your personality?” Then more into the research phase of like, “Okay, what things are you interested in?” Get some information about them. Figure out like, “Okay, I like the idea of recruiting but what is the life of a recruiter like? Do I actually think that it would be a good fit for my personality?” et cetera, et cetera. Then the more practical stuff like, “How do you put together a resume first and gear it towards a specific job and whatnot?” That produced the Framework and then here we are and now there's the whole Framework, we have monthly calls where people can ask questions.

In terms of what people talk about is just being amazing, that is the thing that people love the most because this experience of being like, “I am not the only one and I feel this particular struggle that I'm having is because I'm just doing things wrong or I'm weak,” and then seeing like, “Oh, there are all these other people who are having very similar experiences,” I cannot overstate how important that is in terms of being able to keep making forward progress, not getting just mired down into “everything sucks and there's something wrong with me”.

In terms of where things are, we have the podcast, which is still weekly and this is the 100th episode, then I just started a YouTube Channel in June which is just another way to give people free information that can help them if they are wanting to figure out what's next, and then The Collaborative is my program that I run. We currently have 80 people in there and everyone is working at different stages but I just love it so much.

Then I do sometimes work with people who are already in The Collaborative on a one-on-one basis. It's not a significant part of The Former Lawyer business model, it's just something that I like to offer for people who are looking for that. Then we also have lots of people who are in The Collaborative and then work with a life coach one-on-one, or Jessica, work with you, specifically about their finances. That's one of the things that I really like about it. It's very important to me that people don't feel like I am the person who has all the answers and that I will give you the magical answer that is right for you. It's really important for me that lawyers know that this is something that will help you, this will provide you structure, this will help you make the connections that you need to make, but you are the one who ultimately has the answers for what is the right thing for you and I just want to help you get there.

Jessica Medina: Now I love that you create both a support network and also are a curator for all things that future former lawyers may be interested in because it isn't a one-stop shop, it never is, it's not a one-stop journey. There really are a lot of things going on. But something that you said about the value of being able to do this work in a community is so different from doing it by yourself, even if you're doing it with a professional, I think part of it is what you touched on and seeing the difference between there being something wrong with you versus there being something wrong with you in a particular system.

If all kinds of people have similar problems in a similar system, then maybe it’s not you, maybe it's just something about the combination that is a problem and that means that you can get into a new system and not feel the same things, not feel like there's something wrong. I think that the weight of that, like you said, it cannot be overstated how important it is to not feel alone in this process. Because it hinders you from being able to feel confident that you could excel somewhere else and feel good, but when you can see that, “Oh, maybe it’s not me, maybe there’s something wrong at a more fundamental level and it's just not a good fit for me. It's a good fit for some people. Not a good fit for me. But there might be a good fit for me somewhere else.”

Sarah Cottrell: Yes. Honestly, I think one of the biggest hurdles people have to overcome in order to say, “Oh, yes, The Collaborative is going to be a good fit for me, this will be helpful for me,” is that recognition like you said. I know for you and me, having now left legal practice, we've had this experience where you get outside of it and you're like, “Oh, there's this whole world of people doing all of these things and operating according to a completely different set of rules.”

I thought the world worked the way that everyone who was a lawyer like me thought it worked, and that's just not accurate. It's very much this lawyer bubble and just getting to that point of recognizing the things that the people around me, and again, not like they're individual people trying to indoctrinate you in this way, it's just the water you swim in when you're practicing law, just getting to that point of being able to believe that I may not feel like this is a system that isn't the whole universe but I believe that there is something else that's possible and I'm going to step out in that, I think that is one of the things that can be the most challenging for people because it feels so real, it feels everyone thinks the way that I think or that my colleagues think about all of the things around career. Just believing that isn't actually true and taking action in accordance with that, I think is so important and it can be really hard for lawyers because you're in that system that if you care about doing good work, this is the only thing you could possibly do, and that's actually not true.

Jessica Medina: Yeah. No, I think it's such an important point. We talked a little bit about how vastly different your work is from what you used to do, but what things about running The Former Lawyer, your life now are actually similar to when you got into the workforce as a lawyer, are there lawyer skills that are really helpful now that you are a business owner?

Sarah Cottrell: Oh, yeah. I think these are things that so many of my guests touch on but just things like being able to communicate something in a concise way that other people understand what you are trying to say. I think as lawyers, we grossly underestimate that skill that we've developed and it's like, “Well, surely everyone can do that,” and then you get out into the world and realize, “I don't know that's a skill.” That's a skill that you've developed and that is going to be helpful for you.

I can't remember who it was but someone mentioned to me recently that as a lawyer, you do develop this ability to just do things even when they're not pleasant and you're like, “I don't want to do this thing but it has to get done for the client,” so you do it. That level of persistence and stick-to-itiveness is something that I think is very helpful, not just in this particular role that I'm in now, but just in general. I also think that being able to synthesize large amounts of information and pick out the things that are truly important, that is another thing, especially as an entrepreneur, where you just have so much all the time, so many things you could be doing, so many different ideas.

As lawyers, your job is to be able to identify what is important and what's not important. Again, I think these are things that, especially if you're working in an environment where you're working with all lawyers or mostly lawyers, you don't see those things as unique skills because you're like, “Well, everyone does that.” Everyone doesn't do that. That's something that I think is really helpful as well. Even just for me, the research and writing, just being able to take in a lot of information and then communicate it in some way that people will understand, all that stuff has been really helpful.

Jessica Medina: Oh, I think that is so poignant. We are constantly comparing ourselves to other lawyers. Yeah, we all need to be good at research and writing. It's a basic necessity of our job. We went to school for it. Not everyone in the world is a good writer, and I have found this as well. I believe on the spectrum of lawyers, I'm a mediocre writer but in the spectrum of the global population, I am a phenomenal writer.

Sarah Cottrell: Yes, totally, 100%. Again, to be clear—this is one of the things that I think is problematic with the legal profession, people who aren't good at writing, there are other things that they are good at that I am not good at, and I know you would agree—we're not saying, “Oh, I'm better at writing than the general population and therefore I'm better than that,” but you think that everything you can do is normal because the people around you can also do that thing but when you are out in the world of non-lawyers, those skills are actually skills that you can use that set you apart. So many people come to me and they're like, “I don't have any transferable skills. I'm not qualified to do anything else,” and I'm like, “Just please, stop saying that because that's so not true.” I completely understand where that's coming from because I literally can remember saying those words so many times. It's just not true.

Jessica Medina: All right. We talked a little bit about how being an entrepreneur requires a lot of experimentation, a lot of what we like to call failing forward, which is basically nightmare in the legal world, but what is the hardest part for you about being in this entrepreneurial space of being a business owner, what are the things that you continue to struggle with as you are embarking on this new life?

Sarah Cottrell: By far, the hardest part for me is just basically being okay with the fact that I can't do everything, because there are so many more things that you could be doing as an entrepreneur at any given time than you literally are capable of doing like there are not enough hours in the day. That for me, and I'm sure there are many lawyers, like I said, who would relate to that just being okay, like I was mentioning limits earlier, just being okay with the fact that I am a limited person and can only do what I can do.

Related to that, I think the other piece of entrepreneurship that has been, and still continues to be very difficult for me, is just like you said, the failing forward, the perfectionist tendency. Because I feel so strongly about getting The Former Lawyer message out and just helping as many people as possible, there is this “But I also want it to all be perfect and I want to do things in the way that is exactly the best possible way.” If you listen to my early podcast episodes, I was doing all the editing or on the YouTube Channel right now, I'm doing all the editing, I am not a professional video editor and so I am sure that there are things that could be done so much better but if I wait until I can do it in the “perfect way”, it will literally never happen.

The YouTube Channel for example is a perfect example of that because if I waited until I could have a full-time video editor, it would be another who knows how long and in the meantime, I wouldn't be getting the videos out and they wouldn't be helping people. I've already been hearing from people who have been watching them and it's been helpful for them and so just being okay with massive quantities of imperfection, that is a constant part of entrepreneurship that I am learning from every day.

Jessica Medina: Oh, my goodness. I think Big Law is the worst training ground for us. There is a level of the standard that from the time that you enter those doors and there are years and years of people and years and years of hours that go into perfecting that work product and when that is what you believe is what is required in order to call something done or to call something ready for the client, you're never ever going to get anything done. The majority of the world just doesn't operate that way. It's an amazing standard and yes, it isn't a standard of excellence but if we all did that for everything, our children wouldn't eat. The human population would starve to death for a lack of a perfect meal being prepared. It is an artificial environment I think.

The fact that you can go from that, Sarah, to this new way of existing, I think is such a tantamount to your own growth and to the way that you have maneuvered this journey, and to the continued exploration that you are embarking on and just finding out more about yourself, about your audience, and about this thing that you're creating that is really, really serving people. Of course, I have to ask this question, if you could go back and give yourself advice, what would you say?

Sarah Cottrell: Oh, gosh, so many things. There are so many ideas in my brain, I'm like, “All the ideas are going to come out at once,” but I think if I could go back, I think I would probably tell myself when the podcast was releasing in August 2019, I would say, “You're not behind and things are going to take the time that they take.” I think as someone who comes from a profession that does have a very linear path and a very regimented and clear path, just experiencing the “I don't really know what's going to happen next. I don't really know if this thing I'm doing is helpful or not helpful,” the answers are revealed in time but it's so easy to feel like I'm not doing enough, I'm not where I want to be, et cetera, et cetera.

I have learned, although I'm not sure that even now I'm applying that incredibly well, that is wasted energy and emotion because if you're taking action and you're moving forward, that is what matters. I think that for me, when I first started this whole deal, I just didn't have a good sense of that. My tendency is to always notice all the things that I think I'm not doing enough of as opposed to all of the things that I am doing. I imagine there are many lawyers who might relate to having that experience.

Jessica Medina: Oh, for sure. I do think your point about that for many, the practice of law is a very structured linear experience. You can see eight years in the future what the gold point is and what you need to do to get there. Yes, partnership can be a black box but you gotta work hard, you gotta sacrifice everything in your life, you have to do excellent work, you have to connect with particular partners, all of that is pretty clear and the timing is very clear. In this space, being a business owner, it's Wild, Wild West, you have no idea what's going on. Am I going toward what I think I am? Like you said, if you're taking action, then yeah, you are because everything that you do will get you closer to where you're supposed to be, but trusting that is so hard when you're used to having the map laid out for you.

Sarah Cottrell: Yeah, and I think for me, having to do that with this business has also helped me to be able to communicate that and articulate that to the people who I'm working with, to the lawyers that I'm working with because in many ways, it's the same in the sense of you aren't going to know exactly what the final destination is, you just need to be taking action. I think for me, having to go through my own experience of that in a different context, at the same time gives me a lot of empathy and understanding for lawyers who are feeling that in their process of figuring out what's next.

Jessica Medina: That actually leads us to our last audience question. Somebody asked basically, “How do you not give up on the search for another career option when you are constantly getting pulled back into the law?” We've talked about journeys are not linear, even out of the law, you might get out and maybe go dip back in for a bit, how do you respond to folks that are in The Collab or that just reach out to you that say, “I feel like I keep getting pulled back into the law,” how do you continue this search?

Sarah Cottrell: Yeah. I think there are a couple of things, and this probably is no surprise to people but one, I really feel very strongly that some community piece is important, and I don't just say that because I run a program that is partially community based, the reason there is this community component is because I think it is so essential. Like you were saying earlier, Jessica, that even if you're working with someone one-on-one, there is a difference between that and just seeing and having the experience of, “Oh, here are all these other people who are doing the same thing,” and seeing in real time that I'm not failing if it's not just going forward in this very obvious linear and super fast way. I think that's one thing.

Another thing is I do find that people who go into the process of making a change with like, “Well, I'm just going to figure out what skills I have and then find another job that matches those,” and who don't do some of this deeper internal work in terms of “What do I like. What are my values? How did I end up here and why don't I like what I'm doing now?” and all of those kinds of things, “What do I actually want my life to look like?” you feel like you're working towards something new but the reality is you're probably not that enthusiastic about those options because they aren't really solving the problem that you're having and so it's much more likely that you're going to lose motivation because you just feel meh, it's like, “Okay, this is another job that might pay similar to what I'm doing now and it's different,” but you're not actually excited about it and there is an element of the known feels safer than the unknown, especially if you're not very excited about the unknown. I think that's another thing to examine if you're finding yourself in this place where you feel like you keep trying.

I think the other piece is, and I know I touched on this a couple weeks ago in a podcast episode about what to look for in a lawyer career coach, but I think you can feel you're doing a lot of work if you're just thinking a lot about how you don't like what you're doing and want to do something else. Thinking about something and actually taking action towards it are two very different things. I feel personally attacked by this statement because as a lawyer and with my personality, I don't like to hear that at all. But thinking about it, I'm coming up with these amazing plans. I think what I've learned more and more in doing this work is if you're doing a lot of thinking and not taking a lot of action, you're going to exhaust yourself and you're actually not going to make a lot of progress and you might find yourself in that cycle of, “I keep trying to get out but I'm not getting out.” Those are just some things to look out for if that's an experience that you're having.

Then also just recognizing that everything you do gives you more information. Even if you're feeling like, “I thought I was making progress but now I don't feel like I am,” just make sure to take the time to reflect on “What have I learned here that I maybe didn't know before?” I often encourage my clients to think about the different things that they're doing in their career as a series of experiments instead of a pass-fail, like “I either did the right thing or I did the wrong thing.” It's so much more helpful to just think of it as “What information am I looking for that I need to be able to make a better decision on the back end of whatever this is?” That is what I would say to someone who is asking me a question like that.

Jessica Medina: Yeah. I love that. You know that I deal with a lot of people through the lens of finances and through the lens of money. I think for lawyers in particular, even when we are doing the lowest level lawyer work, it is still often better paid than the highest level in other industries and so it is easy, it's kind of an easy money. If money is a stressor for you, figuring out what you really need so that you have comfort and safety to explore something else is such an important exercise so that you're not just staying in law out of fear and you can start doing some of these experiments. You can start taking action from a place of comfort and security rather than thinking, “Well of course, I can't do anything else because I have to make this amount of money or law is the only place where I can really make a living the way that I want to,” just pulling back the covers on that a little bit and seeing what's actually true.

Finally, Sarah, what can we expect from you and Former Lawyer?

Sarah Cottrell: I think the thing that I am most excited about this year that's coming up is I am planning to run a guided track in The Collaborative starting in September. What that means is typically when people come in, we've talked about the framework that they work through and people are doing that at their own pace, and so what I'm experimenting with starting in September is seeing if people having a little bit more structured like, “Okay, this week we're going to do this, next week we're going to do this, and we're going to be having most likely weekly calls where we're checking in on those small pieces of stepping through the framework in a group way.” That is something that's coming up this fall that I'm super excited about.

Other than that, I think that for me at this point, I literally hear from people every week who are like, “I found your podcast and oh my goodness, it made me feel less alone,” or “I came across your website and literally you're saying the things that are in my brain. Thank you for saying these things,” or people on LinkedIn who are like, “You posted about this and I am having this exact problem and it just gave voice to something that I felt I was experiencing by myself.”

My goal for this next year, at least, is to just make sure that more people hear about these things that are available, whether it's the podcast or the YouTube Channel, or if they are needing more specific help, my program The Collaborative, just getting the word out more because I hear from people all the time that it is so helpful and I just envision the person who I was and how much this would have helped me, I just really want to be able to do that for as many lawyers as possible.

Jessica Medina: Oh, well, you're already doing it for more lawyers than it's ever been done for before. Thank you, Sarah. If this is the first time that someone is listening to your podcast—congratulations, listener, you picked a good one—where should they get started with you other than listening to the first 99 episodes of your podcast?

Sarah Cottrell: You can definitely do that. I have this free guide, it's called First Steps To Leaving The Law and it's literally I sat down and thought, “What are the very first things that I think anyone who even wants to think about leaving legal practice, what things should they be doing?” That's what is in that guide. You can get it at When you do that, you end up on my email list, which email is probably my favorite part of what I do in my business and it's because it involves writing. I read and respond to every email so when you're on my email list, you hear from me every week, multiple times a week most likely, and that's where I correspond with people the most in terms of you can reply to any email and let me know what you think or what questions you have, so, that's the place to go.

Jessica Medina: Awesome. This has been so amazing. Thank you, Sarah, for everything you are bringing into this space. I have worked with some folks from The Former Lawyer Collab and they rave about it that it is life-changing and I'm just so excited to know you, to be friends with you, to be business buddies with you and to be just seeing what everything you're doing here because it's awesome and it's amazing. Thank you.

Sarah Cottrell: Thank you so much and thank you for doing this.

Thanks so much for listening. I absolutely love getting to share this podcast with you. If you haven't yet, I invite you to download my free guide: First Steps to Leaving the Law at Until next time, have a great week.