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, hello, everyone. I'm super excited to share this week's conversation with you. It's my conversation with Matt Maxwell. Matt and I went to law school together in Chicago and we graduated in 2008 as I'm sure you know about me from previous episodes if you've listened. You'll hear some of that in this episode.

Matt has a lot of great wisdom to share. He is currently a leadership coach and facilitator. You will hear all about how he ended up there in this conversation. Here's a quick word from our sponsor and then it'll be right into the episode.

This episode of The Former Lawyer Podcast is sponsored by my free guide: First Steps to Leaving the Law. Look, I know that there are a lot of unhappy lawyers out there who are overwhelmed at the thought of leaving the law and literally don't know where to start. You can grab this guide and take the guesswork out of it. Go to formerlawyer.com/guide and start your journey out of the law today. Seriously, you can get it and start today.

Back to the conversation.

Hi, Matt. Welcome to the show.

Matt Maxwell: Thank you. Glad to be here.

Sarah Cottrell: Why don't we just start out for the listeners with you explaining a little bit about how you decided to go to law school?

Matt Maxwell: Okay, wow. Looking back I'm like, “When did I even decide to go to law school?” It was more like I started off as a music major in undergrad and then I was a history major. I got married during my undergrad really young and wanted to have a family and it was like, “How am I actually going to support a family?” I was like, “Oh, maybe law school.” I didn't have any law school family members or lawyer family members so I didn't really know much about it.

I just talked to a few lawyers and was like, “Oh, maybe I'll look into it.” Then I took a practice LSAT and got a ridiculous score. Then I started going, “Oh, maybe I should look into this a little more.” I was like, “Well, maybe I'll just take an LSAT class.” Then I just took an LSAT class and I was like, “Well, maybe I should just take the LSAT and see what I really get on it.”

I took the real thing and then it was like, “Well, maybe I should just apply the possibles and see where I get into.” I got into some. I was like, “Well, maybe I should just go visit them and just choose one.” Then it was first month of law school and I'm like, “When did I actually choose to do this?”

Sarah Cottrell: Yes. I totally understand that. I had a not dissimilar experience.

Matt Maxwell: There was clearly the “It could be a good career.” I had also known some lawyers who did really cool public service stuff so I was like, “Oh, it could be a great way to help people and get to have a well-paying career and provide for my family.” I thought about it, but I really don't remember ever being like, “Yes, this is what I want.” It was just like I was on this track and then all of a sudden I was there.

Sarah Cottrell: Yeah. I ask this because for me, I had not really, had you done any serious thinking about specifically what you would do or was it more just these amorphous categories of like, “Well, I could be this type of lawyer or that type of lawyer”? Does that question make sense?

Matt Maxwell: Yeah, not really, no. Our first year of law school, it was like, “I don't know.” As an American history major, I had taken a Constitutional History of the United States class as an undergrad so I had delved enough into Khan Law that I was like, “Oh, that's interesting to me.”

Sarah Cottrell: Oh, yes, of course.

Matt Maxwell: Of course, as an actor, being a trial lawyer was appealing in some ways but really I had no clue. I talked to some lawyers, family friends, and stuff, but really no idea what I would want my day-to-day life to be like as a lawyer or how I would create that.

Sarah Cottrell: Yeah. When you say you realized in your first month this “When did I actually decide this?” does that mean that you are still in law school and thinking like, “Maybe this isn't right for me”? Or was it more like, “I'm here now, let's just carry on”?

Matt Maxwell: Oh, no. After I took the LSAT, I started teaching it and I loved that. It turns out, it's disappointing, but taking the LSAT was my favorite part of my entire legal journey.

Sarah Cottrell: You just love those logic games.

Matt Maxwell: Yeah, I did. I liked teaching it and this full-time LSAT teaching gig opened up and I got a notice about it I think about a month into law school. I sent a message to my wife at the time and was like, “What would you think about us leaving?” because yeah, that was about when I was like, “I don't actually know if this is what I want to do,” but there was totally the sunk-cost fallacy or whatever it's called where I was like, “But I'm already $10,000 in debt, I got to go through with this now.”

Sarah Cottrell: I might as well go for the 100 or the 200.

Matt Maxwell: Yes. That was when I started having those. There were things about law school I hated, there were things about how it’s structured that I hated, but there were topics that I enjoyed so there were definitely doubts and there was definitely like, “What am I doing?” and there was still hope that I would land in something that I enjoyed.

Sarah Cottrell: Yeah. Where did you end up going after you graduated?

Matt Maxwell: I really loved corporate law so by our second year I was pretty sure I wanted to do transactional law. I went to a firm called Brownstein Hyatt Farber Schreck which is in Denver which is my hometown. I went from UChicago to Denver. As you know, we started practicing law in the fall of ‘08.

Sarah Cottrell: Yeah, of an excellent time, if ever there was one.

Matt Maxwell: Yeah, especially to do mergers and acquisitions which is what I was supposed to be doing. I spent basically two years not working, always being totally stressed out about how little work there was and ended up doing a bunch of different [work]; there was bankruptcy work, basically our group had very little, there was a month where I think I billed 19 hours the entire month. It was awful. They did a couple rounds of layoffs and I survived for a while and then finally, it was like, “We don't have work. This isn't working.” No kidding, it was awful. It was really miserable.

Sarah Cottrell: Yeah. I did notice that.

Matt Maxwell: I can do the math. I got really, really lucky because I just started applying for other stuff and I ended up getting an in-house gig at a financial services company in Denver and ended up specializing in mutual fund securities law. They call us 40 Act lawyers because we're specialists in the Investment Company Act of 1940.

That ended up being my niche, which I really liked, it really was a good mix for my personality. It's not very adversarial, it's mostly regulatory but there's also in-house. You get to work with a lot of financial folks that are creating financial products and that was fun for me. It turns out that when I decided to go back into Biglaw, it was a really great niche to have, it was really easy to go back when I went back.

Sarah Cottrell: How long were you in-house before you decided to go back? What made you make that decision?

Matt Maxwell: I spent three years in-house doing mutual fund law. During that period, I went through some major life transitions. I was a devout Mormon and I left Mormonism and that led to my divorce. In all of that, part of my spiritual journey was realizing that when we die, that might be it. I'd always lived with this really great assurance of an afterlife based on my religious upbringing.

When I started confronting the possibility that maybe we just live and we die and then that's it, this is our one moment to experience things, when I started getting present to that, it became really clear that I didn't want to spend that moment drafting mutual fund perspectives.

Sarah Cottrell: I was going to say you didn't want to spend that one moment in Biglaw or I guess in-house is when that happened, this revelation.

Matt Maxwell: Yeah. For a lawyer, I had a really nice setup because when I was in-house, I liked the work I did. I worked nine-to-five, I almost never worked more than eight hours a day, I think probably three times in three years I stayed late. For the first couple years I was there, we couldn't get email access on our phones, so literally, I walked out the door and had no work until the next morning.

Sarah Cottrell: Which was fantastic.

Matt Maxwell: It was amazing, it really was.

Sarah Cottrell: Incredibly rare.

Matt Maxwell: Yeah, so rare. I wasn't passionate about the work I did but the people were good people and it was a nice company. I wasn't making top Biglaw salary but it was very comfortable living and nine-to-five, 40 hours a week. That allowed me to act, which is one of the other things that I really love.

When I was in Denver in-house, I started doing a ton of acting, nights and weekends. My schedule was predictable enough that that was fine. In some ways, I had a really great setup; comfortable living, nine-to-five, doing work I didn't hate. But when I went through this transition, I just was like, “I don't hate this.” Part of it was I didn't have children. If I had family responsibilities, I probably would have kept doing it, but I was like, “It's just me and I don't hate this but I do not love it. If this is our only chance to live, there's all kinds of other things I want to do.”

I took this really scary choice because I had such a comfortable gig and I went back to Chicago and went back into Biglaw primarily so that I could pay off my loans and leave. The rate I was going in-house, it was going to take another seven or eight years until I had all my loans paid off, and by going back to Biglaw, I paid them off in a year.

Sarah Cottrell: That is amazing.

Matt Maxwell: Yeah. Then I worked one more year after that saving money so that I had a cushion before I jumped out of the law plane.

Sarah Cottrell: When you went back to Biglaw, are you saying you already knew “I want out of this so I basically want to accelerate my exit strategy”, is that what you're saying?

Matt Maxwell: Exactly. I dove in and I worked my ass off for a couple years. Basically, I set aside acting, mostly set aside acting, all kinds of other stuff that I would have been doing. It was a really scary choice because man, I've got such a cushy spot here in Denver with this in-house position but I was just like, “No, I don't want to spend my life doing this so I'm going to dive in.” I just worked my ass off for a couple of years so that I could create the financial space.

Sarah Cottrell: What year was it that you left that Biglaw job?

Matt Maxwell: Beginning of 2016. It's now been three and a half years.

Sarah Cottrell: Okay. You knew you wanted to leave the law by the time you went back to Biglaw. Did you know what you wanted to do specifically or was it just like, “I don't want to be doing this”?

Matt Maxwell: Well, there was definitely “I don't want to be doing this”, but I feel really fortunate, I liked the 40 Act and when I went back into Biglaw doing it, I worked with boards of directors and I really enjoyed our clients. All in all, I was like, “If circumstances were different and I really had to do this, this would be okay.”

But there were other things I definitely wanted to do; one was pursue acting at a higher level. When I left, the plan for my first year was I had an agent, it was like I'm going to pursue more professional acting opportunities and I got a job teaching LSAT at a great company that pays really well. Between the acting and teaching, I could cover my expenses.

Sarah Cottrell: Were you still in Chicago when you were doing that?

Matt Maxwell: I was. That was kind of the short term. I didn't think either of those were long-term, what my soul yearned for. I really love acting and it's super fun but I knew even then that it's fun but it's not my calling, it's not where I find the most fulfillment and meaning. I really took some time as I was leaving law and that first year where I was just like, “Okay, for a year, I'm going to give myself the freedom to just teach, act, and explore.”

I just really want to make a difference in people's lives. I want to make a fundamental difference for them in a way that leaves them feeling joy, happiness, more love, and better relationships. I wanted to do what I was doing teaching the LSAT only instead of teaching, leading, or presenting things that made a more fundamental impact for people.

I was like, “I want to be Stephen Covey.” I was like, “I don't know exactly how this looks or what I would be doing or to be teaching but it's something Stephen Covey who's one of my personal development favorites.” That's when I started exploring coaching, talked to a bunch of coaches, started exploring coach-training programs, and then ended up doing a year-long intensive life-coach training program which I loved, it was awesome.

Since then, I still teach and I still act, but my main career has been in coaching which I really like. I've started doing more workshops and organizational work in addition to working with one-on-one clients.

Sarah Cottrell: Tell me more about that work and maybe we can go back and you can talk a little bit more about what the training was like and then how that translates to what you're doing now.

Matt Maxwell: Yeah, sure. The training was year long. We did one weekend a month in person for a year and then had a bunch of assignments and other things to practice. The coaching that I'm trained in is called ontological coaching. If anybody wants to look it up, I trained with Accomplishment Coaching which I highly recommend. I now actually help train coaches that are doing that program.

I spend time in New York doing that now. Anyways, it's an ontological coach-training program. Coaching's challenging because there's no license required to call yourself a coach, a life coach, or an executive coach. There are people that are just like, “I really want to give advice to people and I've got a lot of good advice so I'm going to call myself a coach.” That's fine. They may have lots of good advice and they may add a lot of value, but that's really not what I would call professional coaching.

Professional coaching is not advice giving. It's really partnering with your client to engage in an inquiry that has them reveal what they really want to do in their life and how to get there. It's not you just telling them what to do. People often wonder like, “What is the difference between coaching and therapy, and what is the difference between coaching and consulting?”

One of the ways that I look at that is that coaching is always a future-oriented conversation. It's always about what someone wants to create in their life. What is the future that you really desire in your career, your relationships, artistic projects, or health? That can be in any area but it's like, “What is the future that you really, really want?”

Some of my work with clients is clarifying that. Then it's “How do we get you from here to there?” The coaching conversations are all oriented towards the future and how to create it. Oftentimes, what we end up looking at is what we're doing to get in our own way and getting ourselves out of our way.

Sarah Cottrell: Yeah. We are all doing that. I was going to say on the coaching piece, I definitely have observed what you described which is there seems to be a wide vast array of people who are coaches, or in some cases, call themselves coaches. When I think of coaching, you said something about therapy, I think of it as in a certain way doing what a therapist does but less so on the mental-health piece and more so just on the what thoughts are in your brain, like you said, what do you actually want, and breaking that down in a way that is structured as opposed to just floating around in your subconscious.

Matt Maxwell: Yeah, exactly. It's pretty tell-tale. Sometimes my clients will have these conversations where it's like, “I have all these problems” and I'm just like, “What are we creating with this conversation? If it's not directed towards some future that you really want, then I'm just going to listen to you for a while but it's not a coaching conversation.” Sometimes they just need to be listened to or they just need to have someone listen to them.

But anyway, for me, coaching can have a really deep impact but it's a different kind of impact than therapy where the past comes up a lot more. In my coaching, we rarely look at anybody's past. It's not like, “How did you get to be this way?” I'm not licensed or qualified in any way to explore traumatic recovery, addiction recovery, or mental health issues.

We do have great conversations and they can be really meaningful, powerful conversations but they're not oriented towards healing in the way that a therapist might and in the way that an untrained coach might. If people are interested in coaching, my training program is accredited by the International Coaching Federation and I recommend that people look there because there are certain standards and competencies of professional coaching that we are working as professional coaches to really have that be what people, when they hear of a coach, that's what they think of, not the random person who's just like, “I'm going to give you advice and tell you how to do things and think,” whatever, they're kind of loose cannons.

Sarah Cottrell: Right. Less like “Let me tell you what to do” and more like “Let's have some actual structure and standards” and less of “I'm going to tell you what to think”. I'm going to help you create the structure for you to think these things as opposed to telling you what things you actually need to be thinking.

Matt Maxwell: Yeah, exactly.

Sarah Cottrell: Yeah. I am very pro therapy. I've had a lot of it, so listeners, therapy, yay for sure.

Matt Maxwell: Yeah. I do too. I work with a therapist and a coach so it's not to denigrate therapy at all. It's important for me to clarify the distinctions. It’s one, just so people understand what coaching is, but also there really is an ethical component of it to me. I am not qualified to treat certain things that a therapist is and I want people to get therapy for those things.

Sarah Cottrell: Yes, and this is what I was just going to say, I think if you are a lawyer and you're unhappy, I personally would recommend that you look for both because there are things that you will get in therapy that I think are very important, and especially if you're in that really miserable place are necessary and they're different than what you can get from coaching, and coaching can also be helpful because a coach is bringing something different to the table. It's not like a coach just provides a subset of what a therapist provides.

Matt Maxwell: Exactly. It’s entirely a different skillset.

Sarah Cottrell: Right. It’s a completely different focus. Therapy and coaching, both very good ideas. Do you specialize in a particular, because I know some people who coach, they specialize in people who are a particular subset of person or a particular series of goals or whatever, do you do that or do you have a particular type of person that you coach?

Then also how do you find the people that you coach? Does that come to you through the organization that you train with or are those people that you are going out and finding on your own? How does that work?

Matt Maxwell: Man, there's a lot there.

Sarah Cottrell: Sorry, yeah. I was like, “And then I just asked four questions.”

Matt Maxwell: I'll get through and stop me whenever you want. The style of coaching that I'm trained in is called ontological coaching. Any coaching, any professional coaching is about your future, where you’re at, and how do you bridge the gap, how do you get from here to there.

For some coaches, there's a facilitative aspect of coaching that's just like, “What are your goals? Why wouldn't we accomplish them? What are you going to do this week? What accountability structure will you put into place?” There's a lot of just really structured facilitating of that future creation. That can be super valuable.

Ontological coaching goes beyond that. We do facilitate but there's also a deeper look at not just what would you need to do in order to create that future but how do you need to be to create that and how are you being that's getting in your way now. There's just a deeper level in ontological coaching.

One of the really cool things about it is that once you're well trained in it, you can apply it to any area of anyone's life. Again, it's part of the difference of being a coach versus a specialist or something, you're not giving advice, you're asking questions in a way that helps clients clarify what they want and how to create it, and what's in their way and how to get it out of their way. That can apply across anything.

It's been really cool because as I started coaching, I just had clients doing all kinds of different things. Some of my clients, our work together is a little bit more focused on their careers. I'd say mostly it's oriented towards careers, but some of them it's been major relationship transitions like divorces or newly single people with big artistic projects. I'm currently coaching a screenwriter who's in LA working towards the dream of having a movie produced. All kinds of really amazing things that people are up to that coaching can be a real powerful boost in helping them create it.

I've coached some transitioning lawyers. A really ripe time for coaching is when people are nearing retirement, which for most people doesn't mean like going to play golf, it means like, “What am I going to do next with my life?” That's really a cool place for coaching. Then over time, my coaching has gotten more and more geared towards organizations.

I'm just launching, the website's going to be done this week, I'm launching a new company called Hearthstone which will be coaching but all oriented towards organizational coaching and culture transformation. Working with leaders of companies to transform the culture of their organization is where I've been like, “Oh, this is what I really love,” because it allows me to do coaching and also workshops, retreats, and broader group work too which I really love.

Sarah Cottrell: That's so interesting. When you're talking about in the organizational context, you're not saying just working with the leadership, you're talking about also working with everyone in the organization?

Matt Maxwell: Yeah. It depends on how we're hired because generally speaking, this is just my own paradigm of transformation, but it has to start internally. I've done some workshops for organizations where I haven't really done a lot of one-on-one coaching yet but if somebody was going to hire us to really transform their organization's culture, there would probably need to be at least some one-on-one coaching of leadership because there's some way they're creating that culture or generating it that they've got a shift if they want things to change on a fundamental level.

What I really love is doing workshops, group workshops, retreats, bigger stuff. So much of coaching is about, I mean there are so many topics that are just so fun. I do this workshop that's called Creating from the Future which presents a particular way of creating goals, envisioning your future, and then from there creating where you're going to go. I've done workshops on powerful listening. Part of coaching is being a really, really great listener and so I've brought some of what I've been trained in there to organizations. Doing that kind of broader group work, I love that.

Sarah Cottrell: You mentioned that you work with a coach and I was just wondering where in the whole lawyer to non-lawyer process did you start working with a coach, was it before you decided to leave or was it after it?

Matt Maxwell: No, it was after. It was when I started my coach training program. As part of my program, we were assigned a coach, a mentor coach that I worked with for a year. In addition to all my other training activities, I had my own coach that I worked with for a year. That was awesome. There were also many times when I was like, “Oh, man, I wish I had started working with a coach sooner.” There were so many ways that I could have been happier.

Sarah Cottrell: Yes, that was part of what I was wondering. I was like, “Oh.”

Matt Maxwell: It was great. Everything's fine and life works out but there's a lot of things that I can imagine I would have enjoyed a lot more and been a lot more prepared for if I had started working with a coach sooner.

Sarah Cottrell: Yeah. I can definitely see that. Do you feel like there are specific things that you bring to your coaching work drawing from your experience working as a lawyer?

Matt Maxwell: Yeah. That's such a good question. It's funny because I think there are some ways that experience has really benefited how I can be as a coach and in some ways I've had to really undo a bunch of my lawyer training to be a good coach.

I think what helps is that basically, my breadth of experience as a lawyer in-house and at firms in the financial services industry, I got enough exposure to organizational dynamics and what it's like to have a really high-power job. I can actually really relate to my clients who have very demanding careers because I've been there and so there's just an ease of empathy with my clients who have just really demanding careers, whether they're in law or anything else.

I think it's really helpful for me to have that. Also just because I can speak the language of corporate world. I think that really is helpful. I worked with a founder CEO who had just major business questions going on and I wasn't consulting on those issues or telling her what she should do but I could understand what she was looking at because I did M&A work. Having some of that background with some of my clients is really helpful just because I get their world and I get the language. That's helpful.

What is not as helpful from our training as lawyers is that for most of us, the things that we really want are outside of our comfort zone and require some degree of risk. As a coach, so much of my work is actually having people stand in the possibility of what could happen outside of their comfort zone, the good things, and actually letting go of the past and how it went.

For a lot of people, it's like what I really want, for example, in a relationship project. Somebody's like, “I really want to have a long-term relationship but the last eight went horribly.” If they're going off of precedent, they're no longer going to work towards what they really, really desire. The lawyer, our common law training of deferring to precedent and what happened and making what happened very important and also thinking about all the ways things can go wrong, which is what lawyers are trained to do, all of that is helpful if we're trying not to be eaten by bears.

Our caveman ancestors had reasons to always be concerned about what could go wrong. For most of us, the things we really want, they have some risk and so actually letting go of the past and letting go of all the ways that we're trained to protect ourselves is such a huge important part of creating the life you really love. My background as a history major and a lawyer, I've had to really, really step out, intentionally step out of a lot of that training of fear, protection, and self-defense because for most of us, that's what's in the way of what we really want.

Sarah Cottrell: I think it's pretty obvious from the fact that I created this podcast that I'm really excited about helping unhappy lawyers figure out a way to get out of their lawyer job. I shared this on my social media recently, but I was driving down the road and literally this idea came to me totally out of the blue. I ran home, I outlined the whole thing, and now I want to share it with you.

Here's the deal. I already have a free guide that sets up the very first steps that you need to take and think about when you want to leave the law and I wanted to figure out a way that I could help people move through it faster, have some accountability, really accelerate their progress, and I am creating a mini course, it's called The First Steps to Leaving the Law Jumpstart, and essentially, that's what it will do. It will get you moving through those steps as quickly as possible because I know that you want to get out of the law and I want to help you do that.

You can go to formerlawyer.com/jumpstart to find out all of the details about that course. The course will release on October 9th, it'll be $97. However, if you pre-order it between now and when it releases, you can get it for only $47, which is a ridiculous deal, so formerlawyer.com/jumpstart and you can see all the details about the Jumpstart course and you can snag it for $47 which is $50 off the price that it will be when it releases in a couple of weeks. I hope you check it out. If you have any questions, shoot me a note on the socials and I'd love to answer it for you.

Sarah Cottrell: I think that's so true. In fact, I think a lot of lawyers by personality, not all, but I know certainly I'm this way and there are a lot of other lawyers who are also this way, are naturally somewhat risk-averse, and then you go through three years of schooling that is basically designed to help you think about every possible risk and how things can go horribly awry.

You're essentially trained up into a certain level of paranoia and being incredibly risk-averse, which then of course, if you're working, for my listeners, you're working as a lawyer, you're incredibly unhappy, you want to make a change but your training as a lawyer is literally diametrically opposed to you actually doing the things that you need to do to get to a place that is better for you because it inherently involves risk which you have been trained to avoid.

Matt Maxwell: I think the thing to add to that is that is it most lawyers stop there and that's why they get stuck? Because they're just like, “It's too scary to even look at,” but it's like if your heart's calling you, there are ways to actually have that experience of fear not control you. There's like we create these glass walls of fear without really looking.

For me it was like when I really looked at it, I had lots of savings when I left, but it was like the worst-case scenario is I run out of money and basically have to go back to being a lawyer, which is already what I'm doing. My worst case scenario is basically the life I'm living and I'm living it out of fear that I might have to live it. When I really got present to it, it was like, “Oh, dude.” And what if I couldn't get a job as a lawyer again? Well, I would live with my parents.

Maybe when people don't have parents, they'd literally be on the street but we probably have somebody in our life that could feed us and give us a place to stay. We create all these nightmare scenarios and they're actually not that bad when you really look at them. But it is tough for lawyers who are in that spot having been trained to avoid risk.

Sarah Cottrell: Yeah. I think facing it, like you said, and actually thinking through, “Okay, what would actually happen in this scenario if it turned into the absolute worst-case scenario?” is very helpful I think. I think that it's important to just actually let yourself think about what you want, which is part of what you were saying essentially, not what you think you should want. Because I think another piece that tends to hold a lot of people back is almost like, “Well, what will other people think if I'm not a lawyer?”

That for me was not too much of a hang up, but anytime a thought like that crept in, I was like, “Am I going to do this thing that I don't want to do for the rest of my life because someone else, in many cases, someone who's not particularly close to me or maybe someone who I don't know that well maybe thinks it's a bad idea?”

When you actually think about what the stories your brain is telling you, you realize, “That would be a terrible reason to make a choice about how I'm going to spend the majority of my waking hours.”

Matt Maxwell: Yeah, and yet it's our default for a lot of us and there's a lot of theory in standing outside of others’ expectations. Hearing you say that, I feel like it can be a really great time if you're in that place, if you're listening, you're in that place where you're like, “I hate this but I'm scared to death to do anything else” to just really consider what is your life for. What do you want your life to be about? What do you want your life to be about?

Sarah Cottrell: Yeah. What do you, you yourself you, and not what do you think you should want your life to be about.

Matt Maxwell: The other thing I want to add to that idea of the other people's judgment or that identity of being a lawyer, one of the things that I didn't expect when I left—because I enjoyed people seeing me as a successful lawyer and it was fun to be that and I got a nice little ego boost out of that, but it wasn't what I thought my sense of self-worth was based off of and I had these other pursuits and I was a good actor—when I left, I didn't know how hard it was going to be for me to give up that ego boost.

It actually really surprised me because I hadn't identified myself very strongly as “I'm a lawyer. That's what gives me value or worth.” I hadn't thought of myself that way and it turns out that I was thinking about myself that way, and that when I left, even though I left purely of my own choice, I was in a great place at a firm, I left in good standing on my way to partner, it was like, “I'm leaving of my own volition”, there were several months where I felt pretty lost.

It was actually hard for me because I realized, “Oh, I really was getting a lot of egoic pleasure from being a successful lawyer.” Even though I chose myself to leave it, losing that felt like I lost a foundation or something. I think it's something for people to just be prepared for and just be with yourself through that and love yourself up. Ultimately, in any career, it’s not where I want to have my sense of self-worth, but that was definitely part of my transition.

Sarah Cottrell: Yeah. I think that's an incredibly important thing for people to hear because I think sometimes, there's this idea of something like, “Well, if this is the thing that I'm supposed to be doing, leaving the law, then I should feel great about it all the time. If I feel doubt or experience negative emotion associated with it, then that must mean I've done the wrong thing.” I think that's just not true. There are things that you're going to have to work through.

For me, I've actually had a similar experience because my previous lawyer job, the most recent one, the one that I left when I left the law, I was working as a staff attorney at appellate court and sort of similar, was doing really well, I left on really good terms, and I never really identified that much with being a lawyer I think especially because for many of the years that I was a lawyer, I knew it wasn't what I really wanted to be doing in the long term.

But for me now, what I'm doing in my days is some combination of freelance writing and editing and then staying home with my kids. I think I underestimated when I would meet people in the last 10 years and they'd say, “What do you do?” I'd say, “I'm a lawyer,” and I didn't necessarily say that and think “This is so amazing. They should be so impressed by me” but I've definitely had to work through some stuff because first of all, if you tell people you're a writer, then they're immediately like, “Well, oh, tell me what have you written that I can read,” and they have a very specific idea of what that looks.

Then also for me, staying home with my kids part time, people have a very specific idea of what a stay-at-home parent, and in particular a stay-at-home mom, is like. It is a big identity shift even though it is the shift that I wanted. You don't really realize necessarily that it's there until you move into it, but it doesn't mean that it's not what you're supposed to be doing.

Matt Maxwell: Exactly. I think we mentioned before, if you want to create what you want, you probably have to go outside of your comfort zone because if it was comfortable to you, you probably would have already had it, basically anything we really want that we still don't have is outside of our comfort zone and that's probably why we don't have it yet. But it's like we go for it, we take those steps, those bold courageous moves towards what we know we really want and it's uncomfortable. It is uncomfortable.

That feeling of like, “Oh, crap, do I really want to do this? Oh, I don't feel so good.” It's like, yeah, don't listen to that because yeah, of course, it's uncomfortable, there's risk, there's unknown, there are things you don't know how it's going to go, there's change of identity, whatever it is, but it's okay to feel scared, uncomfortable, or even crappy and still have it be going towards the thing you really want.

Sarah Cottrell: Yes, totally. Do you ever miss working as a lawyer?

Matt Maxwell: No. Let's see. I do sometimes. I really liked a few. I would go to these big board meetings and I loved seeing our clients and sometimes there were intense things going on in our little lawyer world. Sometimes I miss that. Honestly, for me, the thing that I'm wanting to create with Hearthstone is a team. I really liked the teams that I worked with, generally, I liked the teams I worked with as a lawyer and I just liked working on projects together.

There was a lot of junior associates doing this and gotta respond to the partner on that and keep this thing moving. I liked that team aspect of my work. Even just showing up in an office, my work now, all my clients I work with remotely and I'm on a training team so I have some different teams that I work with but nobody that I'm day-in and day-out working with. I miss that and that's something that I'm wanting to create through Hearthstone is a team of coaches that then goes into work with organizations because I miss that just day-to-day interacting with the people I was around.

Sarah Cottrell: Humans.

Matt Maxwell: Yeah. It's funny because I didn't really appreciate the water-cooler talk when I was in Biglaw just to like, “How was your day and how was your weekend?” and whatever, just the simple stuff that we talked to humans about, and then after I left and was doing a lot more independent things, I was like, “Oh, I really miss that.” Maybe that's in part because I'm single and depending on my relationship life, I may or may not have someone that I just see every day and so I do miss that from my lawyer days.

Sarah Cottrell: Are you introverted or extroverted?

Matt Maxwell: I think it depends. When I've done Myers-Briggs, I'm right on the border. I've gone I and E. I think it depends on what I've had less of. If I have too many people, I score I and if I haven't had enough people, then I score E because I'm thirsting for that. I really am a person that wants and needs both.

Sarah Cottrell: Yeah. Because I was just asking because I am definitely introverted, and I realize most people know this, which means that you find being around people to be more draining than energizing and you need to be by yourself to get energy. But even so for me too, that rhythm of seeing people every day and just talking about your life, going from that to not having that is a big transition even if you're someone for whom that is somewhat draining like me.

For people who are listening and they're lawyers, and they are not happy and they know they don't want to be a lawyer but they're not really sure where to start, what is your best piece of advice for those people?

Matt Maxwell: Can I give a few?

Sarah Cottrell: Yes, please do. I know I was like, “Oh, maybe I should ask for what is your advice generally?”

Matt Maxwell: Well, one is talk to me, or talk to a coach or talk to somebody who's been through it at least. But as a professional coach, I'm really a huge advocate for what that can bring to people who are looking at and daunted by big transitions. That's one thing. I wish I had talked to a coach. I would have designed my exit differently and I think had a more enjoyable path. That's one thing.

But that aside, I think one thing I would go back and tell myself is if you want to leave, do it. Work towards it. Create it. Maybe it'll take a little time and maybe there is getting your financial stuff in order or maybe there are different things that you want to complete before you leave, but there are a lot of really great careers, other types of experiences, there are all kinds of awesome things.

From my perspective too, it's just like, depending on your religious beliefs, this is it and so if you hate what you're doing, your life's not about hating what you're doing. On the other hand, the other thing that I would go back and tell me is that getting through this is not a great way to go through life either. As long as you are a lawyer, doing whatever you're doing, look for ways to enjoy what you're doing because there are some ways in which we think our circumstances are the problem and they're not.

Sarah Cottrell: You’re saying that leaving the law will not completely fix everything about your life and will not immediately be.

Matt Maxwell: Yeah. There are so many lawyers that put all of their energy on “If only my boss were different. If only my work were different, and it's not and so it's their fault and that's why I'm unhappy. But there's nothing I can do about it and so I'm just stuck getting through this.”

I think that's the trap for most people of law and a lot of careers is just like, “Get through the LSAT and then I just got to get through my 1L year. I just got to get through law school and just get through the bar and then just get through my first few years as an associate. I just get through to partner and then with my partner, just got to get through these first years and get my clients. Then I'm just getting on with my senior partners. Maybe I have a little bit more fun but then you just gotta get through this until retirement.” It's like all you've known is getting through this.

If you left the law, if that's what you've been practicing, you're still probably going to be getting through stuff, it's just going to be other stuff. But that's what you've been practicing, that's what you've been getting good at is suffering through stuff. Maybe the law is contributing to your unhappiness, but my advice to people would be see what there is to enjoy now and practice enjoying whatever that is.

Are there relationships you care about where you're at, connection with other people, maybe there are other kinds of meaningful things you're doing outside of work or maybe within work, mentoring? Whatever it is, see what is meaningful to you in life, in what you enjoy, and find ways to create that now even as you're transitioning out. That's not necessarily that you need to stay, but I think looking back now, I see all kinds of ways I could have taken responsibility for my happiness if I hadn't put it so much on my circumstances.

Sarah Cottrell: Yes. Two things came to mind while you're talking; one was to your point about what someone's religious views, whether you don't believe there's life after death or you're not sure, or you're like me and you believe that there is, regardless, to stay in a place where you are not happy and you could be doing something else simply because you think, “Well, eventually, things won't be terrible,” I'm trying to think of a way to say this, I don't want to be rude, but that doesn't make sense.

If you believe there's some greater meaning to life, then go after that. Just being like “Well, this is terrible but someday eventually, it might not be so bad” is not even necessarily consistent with what you think about how the world and the universe works. That was one of the things I thought of when you were talking.

The other one, you were talking about being unhappy as a lawyer and putting everything on, like once I leave the law, then everything will be amazing as opposed to “I will still be a human person in the world with a life who has challenges and struggles.”

You were saying learn to enjoy where you are or the pieces of where you are that you can enjoy, I think part of that is, or at least for me, my experience was once I realized that I don't want to do this forever and I want to make a plan to not be doing this forever, not just be thinking I don't want to do this forever but through some magic of whatever, I will someday not be doing this, once I had felt that I had an actual plan, I found that it was much easier to enjoy the pieces that were enjoyable, and not in like “Because one day, everything will be so perfect because I will not be a lawyer anymore,” but more so because it was like, “I knew that I was doing everything that I could be doing where I was to eventually get to a life that would fit me better,” as opposed to focusing on the parts that were least suited for me or made me most miserable.

To another point you made, I think, that is the value of having a plan and potentially having a coach, having some structure as opposed to just feeling like “I'm in a cesspool of misery and I don't want to do this and maybe magically someday, my circumstances will change.”

Matt Maxwell: Yeah, totally. It makes so much sense. The other thing it gave me, it's great, it's so true, just being on the path that you know is aligned with what you really want, it's like you can almost be with any part of the path if you know you're on it, where you're aligned and you're actually taking action aligned with that.

That's definitely some of what I experienced during those couple of years I went back to Biglaw. Sometimes it was pretty rough and there were lots of crazy nights, weekends, or whatever, but still I know this is aligned, I'm on the path of creating the life I really want.

The other thing it gave me was a little superpower. I felt I had this just supreme advantage over other more junior lawyers, which is I didn't care. I mean I did. I wanted to do a good job and I did a good job but also I could be with mean partners more or somebody giving me really harsh feedback and I just can be like, “Oh, okay, cool, thanks.” I would just listen and take it and I just didn't care as much in a way that actually made it a lot more fun. It wasn't like that was a resigned to poor quality work, I still did great work but it was just like I didn't take it all so seriously. For some reason that made it more fun for me.

Sarah Cottrell: Yeah. Not so emotionally wrapped up in everything.

Matt Maxwell: Yeah, not so much fear of like, “Oh, what if they don't like me?” Well, whatever, I'm leaving anyway.

Sarah Cottrell: Yes. It's like, “Eventually I'm going to leave this and do something that 99% of these people think is crazy, so how much can I really let their opinion of me structure how I feel about myself?” which, again, like you said, it's not to say, “Oh, don't do good work,” you still do good work, you just don't have that emotional knot of stuff tied up in the work that you're doing.

Matt Maxwell: Exactly. There's not that attachment and fear.

Sarah Cottrell: Yeah. So good, so true. Just a couple more questions for you. One of them is is there anything that you wish you had done differently in your path out of the law other than that you wish you had had a coach earlier?

Matt Maxwell: Yeah, let's see. It took me about a year and a half to finally get there. When I left, I left with a lot of lawyer mindsets. One of those was fear around money. I had saved up, I got a big bonus before I left, and I had this savings, and I was like, “I'm not going to spend any of it. I'll invest it. I'll use some of the investment earnings but basically I can't spend it. It's sacred.” It scared me to think of using any of it.

I was like, “I've gotta find a way to make it all work.” I went quite a while, it was just really pinching pennies and afraid of losing any of the savings. I finally reached this point where I just realized that the worst-case scenario if I used all of my savings, which I was not anywhere close to, was that I would go back to a law job. I didn't really want to do that but it wouldn't be the end of the world.

I'd even gone back part-time into law, for a little while, I went back part-time because I was so afraid of losing any of my savings. Anyways, I just had this epiphany where I was like, “I worked so hard to give myself the gift of a free life,” and part of that was saving up and I was like, “I'm going to actually receive that gift.” I left that part-time job, I traveled a bunch, I actually allowed myself to experience the enjoyment of the freedom that I had gotten. It took me a year and a half to actually really enjoy it, not worry so much, and just enjoy the freedom.

Anyways, for me, I think that the biggest thing I would do differently is right off the bat, I would have been like, “Dude, you worked so hard, you deserve to relax and enjoy.” I probably would have traveled more up front. I just would have allowed myself to use more of the savings and just enjoyed the gift.

Sarah Cottrell: I think that is a great thing for people to consider as they're thinking about getting out of the law and not being a lawyer anymore. If people have questions about your experience or about coaching, or even if they're interested in working with you, where can they find you?

Matt Maxwell: Great question. They can find me anywhere, LinkedIn, Facebook, Instagram. My website which is about to launch is thisishearthstone.com where they can learn more about coaching services. They can also hear me on my podcast, which is the Cultivating Courage Podcast that I run with another coach. They could follow that.

My book is almost published. We haven't even talked about my book, that's the other thing I've been up to. It's called How to Hold a Cockroach: A Book for Those Who Are Free and Don't Know It.

Sarah Cottrell: Interesting.

Matt Maxwell: That'll be published within, depending on when you release this, it may already be done but that's coming pretty soon.

Sarah Cottrell: Yeah. I was going to say for our listeners, we're in the first week of August and this will probably be coming out probably the first week of September, second week of September-ish, so all of those things should be available and I will put links to all of that in the show notes so that it would be easy for them to find.

Matt Maxwell: The other thing I want to mention is that if you're listening to this and you're like, “Oh, maybe it would be really great for me to work with a coach,” I happily do free hour-long initial sessions so that people get a feel for whether or not they want to be coached, what coaching is like, and if it's a good fit. It's really important if you want a coach to have a great fit.

Myself and most coaches that I know are willing to do some initial session for free. If you're interested in exploring it at all, I really recommend that because it can give you a feel for whether or not it would be helpful for you.

Sarah Cottrell: I think that is great. Listeners, get on it. Is there anything else, as we're wrapping up here, that you would like to share with our listeners before we say goodbye?

Matt Maxwell: I think we've covered it. I think just returning to that point of just really looking at what you want your life to be about and whatever fear is there, being willing to move through that fear in service of what you really, really want for your life, whether that's in law or in anything.

Sarah Cottrell: I think that is a great place to end this. Thank you so much, Matt, for being with me on the show today.

Matt Maxwell: Sure. You're welcome. 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 formerlawyer.com 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.