How to Leave Litigation and a Legal Career for Consulting with Stinson Mundy [TFLP 128]

Today I’m excited to share my conversation with Stinson Mundy with you. Stinson started as a litigator and eventually decided to leave litigation to open her own solo practice. Now, she is a director at a company called Envoy Portfolio. 

We talked about her legal career journey and later, her decision to leave the law. And we also touched on many common themes that come up on the podcast. I just know that everyone reading will get something of value out of this. So without further ado, let’s get to my conversation with Stinson.

A Bit About Stinson Mundy

Stinson Mundy is a former litigator and corporate attorney, turned consultant. Today, she is a director at a consulting firm called Envoy Portfolio. Her legal career journey has been filled with transitions and refiguring.  

When I asked Stinson how she started her legal career path, she confessed that she really never thought she would be a lawyer. In fact, she always thought she’d be a history professor. 

But when she realized that this wasn’t the right path, a legal career was suggested to her. It sounded like a good idea, so Stinson decided to pursue a legal career.

Stinson loved law school, especially the intellectual and problem-solving parts. She never thought she would end up being a litigator. In fact, she was more interested in corporate law. From a young age, she was intrigued by how businesses operate. 

Her first summer was spent doing an internship for a Justice of The Supreme Court of Virginia. After law school, Stinson actually went on to clerk for her. The summers after that were spent working and doing internships in-house. ‘

After law school, Stinson went on to start applying for jobs. But every corporate firm that she applied to only focused on her clerkship. Oddly enough, this was looked at negatively. 

So, she found herself applying to litigation jobs because those were the firms that were excited to have her. Her clerkship made her marketable, so Stinson ended up at a boutique litigation firm. 

Another familiar sentiment was that Stinson said that she was not ready for what a legal career really is. As many of you know, law school doesn’t prepare you for a legal career. 

Stinson was in a small firm. She described the beginning of her legal career as “trial by fire,” meaning she gained experience very quickly. It was fun for the first couple of years. But after 6 years and becoming a mother, she began to rethink this legal career path. 

Time For A Change 

In 2015, Stinson decided it was time for a change in her legal career path. After two kids, the unpredictability of her litigation job became too much. She needed a better work-life balance.  

She moved from litigation into in-house. Unfortunately, she still didn’t feel comfortable in this new legal career path. She struggled with the feeling that she wanted to leave the law. She had already struggled with this before moving in-house.

Having A Solo Practice

Stinson also confessed that instead of reflecting on whether or not to leave the law, she convinced herself to make another transition. She decided to open her own practice.  

Stinson reflected on her time in her solo practice being the most enjoyable part of her legal career. But after a while, she just realized it wasn’t the type of law that she was practicing. As much as she liked her clients, she just didn’t like being a lawyer.  

Deciding To Leave Litigation And The Law For Consulting 

In the end, Stinson knew she had to give it one more shot. But this time, she was going to do it her way. She had this love of business and the non-legal side of business. She decided to go into general consulting. There, she would be able to combine her legal skills and that love of business. 

Instead of the normal firm, she wanted to figure out how to mirror that without billable hours. Stinson was adamant that her firm would not go by the normal billable model. 

Losing The Billable Hour Model

The reason why Stinson felt so strongly about losing the billable hour moment is because of the stigma it has with clients. Many clients have a nagging sense that lawyers make things more complicated to get paid more. It’s not about trust or ethics, it’s the nature of the billable hour model. Clients are afraid of it. 

So, Stinson opened a firm with a subscription-based model with two types of clients. On one side was the low monthly fee for a moderate level of consultation. On the other side was an all-inclusive package for a higher fee.

With the subscription-based model, those fears were extinguished for Stinson’s clients. They could pick up the phone and talk about what they need to without worrying about excess fees.  

Finding Envoy Portfolio

Along the way, Stinson had a client called the Envoy Portfolio. In 2019, she had the opportunity to join that firm. Envoy Portfolio is a negotiation facilitation firm that helps clients like corporations have difficult conversations. 

Stinson noted that this new role mirrors the work she did as a lawyer. Plus, it has new layers of strategy, business, and communication. She also enjoys bringing people together and solving problems to the benefit of both parties.  

Are You Looking To Leave The Law? Remember This:

If you’re looking to leave your legal career in the past, it can be hard. You may convince yourself to stay multiple times as Stinson did. But, when you finally decide to leave the law, Stinson has a few words of advice for you. 

Stinson encourages those looking to leave the law to reach out to your network of non-lawyer friends. It’s very tricky to get an objective view of the legal industry from someone who’s inside it. Go talk to your friends and family. 

Let them help you figure this out. They may also be able to give you ideas about your next career move. Being able to shift the way that you’re viewing your options is huge. And, having those outside views is really helpful. 

Get Help With Your First Steps To Leaving The Law 

If you’re ready to leave the law for good, I have created a free guide, First Steps to Leaving the Law. This guide is for anyone out there who wants to leave but doesn’t know where to start. This is exactly where I was when I was ready to leave the law.

Hit the link to get the free guide in your inbox today. If you are ready to figure out what’s next for you, download the free guide, and get started today.

Mentioned In This Article

Envoy Portfolio

First Steps to Leaving the Law

Connect With Stinson 



Envoy Portfolio Website

Sarah Cottrell: Hi, and welcome to The Former Lawyer Podcast. I'm your host, Sarah Cottrell. I practiced law for 10 years and now I help unhappy lawyers ditch their soul-sucking jobs. On this show, I share advice and strategies for aspiring former lawyers, and interviews with former lawyers who have left the law behind to find careers and lives that they love.

Today I'm excited to share my conversation with Stinson Mundy with you. Stinson started out as a litigator and eventually she opened her own solo practice, and now she is a director at a company called Envoy Portfolio. She'll share more about what that means and the transition. We also talked quite a bit about the problems with the billable hour model, which is a favorite topic around here. I'm really excited for you to hear this conversation so let's get to my conversation with Stinson.

Hi, Stinson. Welcome to The Former Lawyer Podcast.

Stinson Mundy: Hi, Sarah. I'm glad to be here.

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

Stinson Mundy: Hi. I'm Stinson Mundy. I am a former litigator and corporate attorney now turned consultant. I am a director at a consulting firm based out of Richmond, Virginia.

Sarah Cottrell: Awesome. Let's talk about why you decided to go to law school.

Stinson Mundy: That's a great question. I am of the pre-recession era where when you weren't quite sure what you wanted to do in life, you went to law school. I thought I was going to be a history professor and then realized that really wasn't the path that I was destined to go on and wasn't quite sure what to do with my life, so my friends and family said, “Why don’t you go try law school?” I said, “Okay.” I'm not one of those people that always grew up wanting to go to law school, to be a lawyer, or really have any idea what that meant, but at the time, it sounded like a really great idea.

Sarah Cottrell: Yes. I relate very much. I think you went to law school around the time that I did. I graduated in 2008 and you were in law school in 2004-ish time, is that right?

Stinson Mundy: I was. I graduated in ‘05.

Sarah Cottrell: Yeah. Okay. I very much relate to that story that there are lots of people who say, “I thought I was going to be a lawyer forever,” but for me, it was one of the options that existed but it was not particularly like, “Oh, yes, I'm on that path.” I was an international studies and leadership studies double major and was like, “I don't really know what I want to do. Oh, law school, that seems like a good plan.” Of course, everyone's like, “Yeah, that's a great plan.” I'm interested to know for you, you go to law school because you're like, “Okay, I'm not going to teach history. This seems like a good path,” so when you got to law school, were you like, “Wow, this is great,” or were you like, “I don't really know what I'm doing but I'm here now,” or did you not try to think about it because you were like, “I'm in denial about the fact that--” whatever? Tell me about what your thought process was through those years of law school.

Stinson Mundy: I'm a nerd and I come from the liberal arts world. I have a master's degree in history. So coming from that world of just consuming books and getting lost in the literature, etc., was fascinating to me. I loved law school. I am one of those people that got lost in the case law and I thought the problem solving and the intellectual piece of it was just fascinating. I never thought I was going to be a litigator. I always thought I was going to do some corporate law and so I just loved three years of being able to nerd out and read everything I could and apply it to problems.

Sarah Cottrell: I think there are a lot of people who go to law school who just really like school, really like thinking about complex issues, and law school can definitely be a good place for that, but then when you end up ultimately in legal practice, it's a very different thing.

Stinson Mundy: It's a very different thing.

Sarah Cottrell: You said you thought you wanted to go to corporate law, so can you tell me a little bit about why you thought that and then how you ended up in litigation?

Stinson Mundy: Yeah. It's sort of a funny story. I was always intrigued by how businesses operate from a very young age. I'm not really quite sure why but I’ve just always been fascinated by business, the business world, and entrepreneurs. When I went to law school, I thought it was going to be really cool to get inside these companies and to help them solve these problems that you follow from the outside. I didn't really know what that meant when I was in law school, but that was just this image that I had. All of my summers were spent working in-house and doing internships in-house, except that I met one of the justices of The Supreme Court of Virginia my first year in law school. She did an unpaid internship for first year law students to just learn more about her work and the role.

That summer, between my first and second year, I interned with her, and I loved it. She's one of the best legal minds that I've ever been around. She went on to be the first female Chief Justice of the Virginia Supreme Court. I then, after that, had the opportunity to go and clerk for her after law school; in a normal clerkship, not just a short summer stint. Because I had worked in-house during the summers that I was in law school, and then I went to clerk, I spent the second half of my clerkship looking for a job. At this point, we are in ‘06 or so, and I'm looking for jobs. Every corporate firm that I applied with all looked at my resume and the only thing that they honed in on was the fact that I had clerked for a justice of the supreme court in a negative way. They couldn't understand why I would have gone and done a clerkship if I wanted to do corporate law. My story, my very true story of “Well, this was an opportunity that I was not going to pass up” fell flat.

I found myself having to apply to litigation jobs because those were the firms who were really excited to have me. They were really excited that I had this clerkship. They seemed to overlook the fact that I hadn't done moot court or done anything else that you would do in law school that would prepare you for a litigation role, but because I had clerked, I was marketable. I ended up with a small boutique litigation firm that was a spin-off of a Biglaw firm doing really cool commercial litigation to start.

Sarah Cottrell: It's so interesting because I think the legal field in particular tends to pigeonhole people very quickly. I've noticed that it poses a challenge for a lot of my clients because you're describing your experience where you did a clerkship, which people can have multiple interests, there can be reasons to do this, that doesn't mean you're like, “Never, I never want to do corporate law,” but yet there's this perspective of “Well, you did this, so obviously you can't also want to do this other thing, or obviously, you're not suited for this other thing.” I think lawyers who are in that position of thinking about leaving the law and wanting to do something else sometimes think that in the wider world out there, there's that same pigeonholing where there is this feeling of “Well, I'm a lawyer, would anyone ever want to give me an opportunity to do anything else?”

But it’s this false sense that's created by the fact that the legal industry does tend to put people in very small boxes quite quickly and then it can be very hard to break out of it. I think this is a really interesting piece of your story because I see that dynamic and how existing in a profession that operates in that way has impacts on people in other ways, including when they are thinking about not practicing law anymore.

Stinson Mundy: I agree completely, and I think that lawyers pigeonholed more than any other profession that I've ever seen. It's to our detriment.

Sarah Cottrell: Yeah, 100%. I think some of it is the prestige focus of, “Well, you do this, this, and this. That means that you're aiming for this thing. You do this, this, and this. That means you're aiming for this other thing. You do this but you don't have this. That means you're not ‘good enough’ for blah-blah-blah.” There's so much of that type of dynamic, which is yet another part of the profession that I think makes people feel like being a multi-faceted human being is a problem and they need to be a law robot.

You were ending this clerkship, basically litigation firms or departments. Those are the places that were excited about hiring you so you take this job. You said that there were some cool cases. In the beginning when you first started, were you going into this job thinking “I'm going to love this”? Or did you already have the sense of “I'm not sure this will be the thing”? What was your perspective going into it and then was that bored out in your experience?

Stinson Mundy: Yeah. I think the expectation going in was really just unknown. I had no idea what I was getting into. I don't think law school really prepares you for being a lawyer, and so I went in bright-eyed into this litigation. I will say the first couple years were really fun. I was traveling all the time. My clients were national. We were a small firm. It was trial by fire so I got a ton of experience really quick. I really did, those first couple years, have a lot of fun. It was only I think after that honeymoon period, it wore off that I really started looking around and was like, “What am I doing? Yes, I'll give it another year or so.”

When I look back now, it was funny as I was thinking about my story before coming on this, it was amazing to me as I was recalling that time, how many every couple years I applied for new jobs and I hadn't really thought about that in a long time, but I think that the disillusion came probably about a year, two, or three, and I just convinced myself to stick it out. “Well, it'll change when you become more of a senior associate. It'll change when this happens,” when really I just don't think that I was ever made to be a litigator.

Sarah Cottrell: It's so interesting, people have shared similar stories so many times in the podcast. There are so many similar stories for the people who I work with and even for myself. I really believe that a large number of lawyers in years one to three pretty much know “This is for me or it's not for me,” but there's so much of that experience of, “Well, but maybe there's this other thing that could be a thing. Or maybe I could do it this way. Or maybe it's just this job or this firm, or I should go in-house.” Ultimately, people generally come back to, “Hey, that gut feeling I had in the first year, two, three years, that was right.” But I think as lawyers, the idea of, “Oh, I should just go with my gut,” is like, “No, I need to construct a logical, rational palace of an argument that would support me making a different decision,” so there ends up being a bit of all winding paths.

You said you eventually hit a point where you were like, “Oh, wait, actually, yeah, this really isn't it and maybe I'm going to try to stick it out for another year but something needs to change.” Was there something specific that caused you to have that realization or was it just everything building up over time?

Stinson Mundy: I think it was a combination of everything building up over time and becoming a mom. It took me a long time as well to reconcile the two, but being a litigator with the travel schedule that I had and the unpredictability of it was just hard. I see with friends now that there's been a lot of really positive movement in the work-life balance and support for women who are trying to raise families as well as have that crazy litigation life. But at the time, I was the only female senior associate in my firm, there were no female partners. I was the only one with a brand new baby. It got to the point where I wasn't going to do it anymore.

Sarah Cottrell: It's interesting because when you were talking about your first couple years and you said it was really fun, you were doing all this traveling, I was thinking, “I'm sure there are some people listening who think, ‘Oh, yes, that sounds super fun,’” but for someone like me, business travel, no; which is again, I think as lawyers, we often tend to feel like we have to examine our feelings to see if they're valid. I was even thinking that there could be people listening who are like, “Oh, my job requires a lot of travel but I don't think it's fun, I think it's super draining and not good. But Stinson's saying that was fun so I should feel like it's fun. Why don't I feel like it's fun? What's wrong with me?” I think that there's that piece of thing that definitely comes into play and then also I think there are a lot of lawyers who find it so hard to accept that what they want, and even what they enjoy, can change over time.

Like you said for you, you did enjoy some of it in the beginning, but then through various things and then with the life change of becoming a parent—which I have a three-year-old and six-year-old—I think sometimes, people feel like they're not allowed to want something different. Can you talk to me about that a little bit? How was that for you? Did you feel you struggled against that? Was that very easy for you? What was your experience with that?

Stinson Mundy: I think what I struggled against was I had this feeling that I didn't really like being a lawyer. Instead of processing that feeling and exploring it, I kept telling myself that it was just because I was doing it the wrong way, that it wasn't that I didn't want to be a lawyer, it was that I didn't want to be a litigator so I went in-house. Then I realized that I didn't like that any much more than I liked being a litigator. Then I went from being in-house to starting my own firm. I will say that was the most enjoyable of the three pockets of my legal career. But still, realizing that as much as I liked my clients and their problems and being able to solve things, I just didn't like being a lawyer.

Sarah Cottrell: Talk to me about the timeline. You started at the boutique firm around ‘06. Talk to me about your progression through that when you became a mom and then the point at which you started your own firm.

Stinson Mundy: I started there, I think it was ‘06, and my son would have been born in 2012, six years into that. I left after my daughter was born and went in-house in January of 2015. Then I started my own firm in July of 2016. I officially closed the door on it in December of 2020.

Sarah Cottrell: Let's briefly talk about the in-house thing because in the Collab, we had a panel—this was a year ago now—but the title was Is In-House The Answer? Because for so many lawyers, if they're working for a firm, there's this idea of like, “Well, if I go in-house, there won't be billables and it will be so much better.” There's a degree to which that can be true, but one, there's so much variability in in-house jobs. To just think of in-house as this monolith is not actually very helpful. But can you talk a little bit about, for you, why it was that it was ultimately not the magical cure-all that many of us think that it might be?

Stinson Mundy: Yeah. I feel like I agree with you completely that there's no one-off for in-house. There are some major in-house law departments that run just Biglaw. There might not be billable hours but there's definitely the same expectations. For me, I went to a client who had never had a general counsel before. I went from having a firm with support to a solo office of me. It wasn't what I thought it was going to be. I liked the work, I liked the problem problem-solving piece of it, but there's a lot of pressure when you are the sole one making decisions now and making recommendations now, and just a lot of different expectations in terms of what you can and cannot do when you have a whole company that is relying on your advice in terms of the company trying to understand what the role is.

At this point, I now had two little kids under the age of three at home and just realized that pressure of “Am I making the right decision? Am I making the right call? Am I giving you the right advice?” was untenable when I was a party of one as opposed to a firm where there were people to bounce off things with.

Sarah Cottrell: I think one of the things too that people often don't think about when they're thinking about going into an in-house role, like the one that you're talking about where it's just you or maybe just a handful of lawyers, is you're often going from a work environment where it's all lawyers so everyone's on the same page, at least to some extent, about how things work and what you prioritize, and then you go into an environment where pretty much everyone else is a non-lawyer and they have a very different set of priorities. Especially when you're talking about a small department or a solo general counsel, that is a very different and differently stressful situation, but very stressful nonetheless.

I really appreciate you sharing that because I think that is an extremely common situation that people find themselves in. Especially when you've been embedded in a work environment where it's all lawyers all the time, you don't even realize what norms—I don't mean that everyone else is unethical and you're super ethical, it's not even that, it's just even just the baseline assumptions you make, the baseline knowledge that you have, it's very different and you don't even realize how much that is playing a role in your work environment until you're in a different environment.

Stinson Mundy: Yeah. I was having this conversation with somebody else the other day too. It's the assumption in a small or a solo general counsel office that you know everything because why wouldn't you know everything? You're a lawyer; questions that would pop up about areas of law that I have no idea about, never touched in my life, and it's like, “Well, I don't understand. You're a lawyer. You went to law school, don't you know these things?” Then the experience with the colleagues that you used to call and banter back and forth, you would call and banter back and forth, and I learned the hard way really early on, I started getting some bills. I was like, “What is happening?” Well because I was now seen as a client. It was a funny experience. The colleague wrote off the time but then I found myself having to ask people, “Okay, can we just talk? I just want to talk through this problem. I'm not looking for advice. Don't open a file on this, but I don't even know where to start.”

Sarah Cottrell: Okay. Talk to me about your experience of opening your own practice, because I know that's something that a lot of people who are listening have considered just because I talk with lots of people who mention that as something that they, in theory, would like to do but there are lots of things that hold them back. Can you talk a little bit about what you said that for you, it was the most enjoyable of your jobs as a practicing lawyer, but then ultimately of course, you said you ended up deciding to close the practice in December 2020? Can you talk a little bit about why it was more enjoyable for you than the other things and then what made you ultimately decide to step away from it?

Stinson Mundy: When I was trying to figure out what I was going to do when I decided that I needed to make a change around 2016, I thought about lots of different things. At that point I thought about leaving the law entirely, doing something completely different. At the end, where I landed at that point was that I needed to give it one more shot, but I wanted to do it my way. I wanted to do it in a way that made me feel fulfilled and that I could sleep at night. I still had this love of business and I still loved the strategy conversations that I had in-house and loved being part of the non-legal side of running a business, and as the GC to a company where you are an office of one, you get brought into lots of things that aren't necessarily legal and people have lots of questions that they want your take on because they like the way that you process information that's different than how they do. It's not necessarily legal advice or a legal question.

I wanted to figure out how to mirror that without billable hours. Really thinking through a flat fee, and I called it value-based billing, so fees commensurate with the value that you were providing the client, not necessarily the time that it took you to complete the project. I decided to open a firm where I was going to create the model that I always wanted to operate. I ended up creating a subscription-based model where I had two kinds of clients. I had one side that were businesses that paid a fairly low monthly fee to have access to me, to ask me the questions that they needed to strategize; and then I had others that then paid a much higher fee to have all-inclusive outside general counsel services.

What I found and loved at that point was that I was really combining this love of business and the strategy side with helping clients figure out how to use legal and my talents to help their businesses grow. But I always knew when I opened the firm that it was probably going to be the catalyst for me to figure out what I wanted to do next, but it was the way that I knew how to make money. As long as I could do that in a way that I felt fulfilled, then I would do it as long as I could until I figured out what that next thing was going to be. I had in the back of my head at that point that that next thing was going to be some sort of consulting, but I didn't know what or how at that point. I loved it. I loved my clients. I loved the model that I had. It defies all logic in how attorneys are taught to bill or to think about the money of a firm, but it was profitable and it was easy bookkeeping in my head, and my clients loved it because they had access to me and they had the ability to talk through those problems.

Then along the way, I had a client called the Envoy Portfolio, which is where I am now. In 2019, I had the opportunity to join that firm. I did a hybrid of testing out the waters as I was part-time-ish in my firm at that point and part-time with Envoy, and then was supposed to start shutting down in early 2020 but there was this whole pandemic thing that put a wrinkle in this place, and so it took about a year for me to put my legal clients to a place where I felt comfortable passing them off. I was not about to abandon them when the pandemic hit. I have been full-time with Envoy since 2020.

Sarah Cottrell: Hey, it's Sarah. I'm popping in here to remind you that I have created a free guide, First Steps to Leaving the Law for anyone out there who is just like, “Ugh! This job is the worst. I need out. Where do I start?” Which is exactly where I was when I realized that I didn't want to be a lawyer. You can go to, sign up, and get the guide in your inbox today. When you grab that guide, you get on my email list, which is the way I keep everyone the most up to date about everything that's happening with Former Lawyer. It's also the best way to get in contact with me because I read and respond to every email. If you are ready to figure out what's next for you, go to, download the free guide, First Steps to Leaving the Law, and get started today.

Sarah Cottrell: Tell me a little bit more about Envoy and what you specifically do there.

Stinson Mundy: We are a negotiation facilitation firm. We help clients which are typically corporations, boards, NGOs, nonprofits, have difficult conversations to communicate better to build partnerships, to exert influence in the spheres in which they need to. I have a love and passion for helping women with self-advocacy skills and negotiating for themselves. It's a nice mirror of the work that I did as a lawyer, and some of the strategy and the love of business and bringing parties together and really working through difficult problems and difficult situations in a way that is mutually beneficial to all parties that are involved.

Sarah Cottrell: When you say that, are you talking about, for example, severance negotiations or things like that, or something else?

Stinson Mundy: Let's see. We might get called in because the board of a company is grappling with some big decisions. They may not have all stakeholders on the same page in terms of how to move forward with those decisions. We help them to facilitate those conversations and to work through their differences so that they come to some sort of mutual agreement among themselves. It's not so much an employment agreement, a severance agreement, or a sale type agreement, but it's building partnerships. It is teaching mutual interest negotiation to companies and groups how to communicate better, how to build partnerships both within and outside your organization. It really is the most fulfilling work that I've ever done because we are helping—especially in this very polarized world that we live in right now—we're helping people move past the need to be right and work towards making progress in whatever it is that the situation that they're dealing with calls for.

Sarah Cottrell: It definitely sounds like something that many lawyers are probably listening to and think, “Oh, that sounds interesting and also quite close to the skill set you might develop as a lawyer.” Are other people who are involved in the company also lawyers? Tell me how about that because I imagine some people might be listening and thinking, “Well, is that something I could do? What would that look like?”

Stinson Mundy: We have three directors here. One is a former diplomat and the other is a former entrepreneur. Among the three of us, we all come at problems very differently and very uniquely, which makes it interesting and exciting and gives our clients just a broad based approach to how to solve problems. I think that from a lawyer perspective, it's interesting because yes, a lot of what I do mirrors some of the stuff that I did when I was actually practicing, but what my clients love is not so much the fact that I was a lawyer, they could care less about that piece of my background, but it's the way that I approach problems and the way that I think through problems is just different than the way that a lot of other professions are taught to think through problems.

I find it a lot with friends who either have also left the law, who are thinking of leaving the law, that the skill set that we discredit the most but is one of our most valuable, is that we just look at problems differently. In the business world, that is such a valued skill set because there is so much groupthink and so much “Let's just follow what the latest leadership book is telling us about how we should think about things”, and lawyers just approach the world differently. That's a really good thing.

Sarah Cottrell: Let's talk a little bit more about the details of that because one of the things, of course, that I hear all the time that I felt myself that my clients are always dealing with is this feeling of “Do I have any skills to bring to the table? Do I have any transferable skills?” Again, to go back to what we were talking about earlier in the conversation about how, if you're in an environment that's all lawyers, you almost can't see the things that you bring to the table because you're like, “Well, everyone's like this,” but that's not actually true. Can you talk a little bit more about the specifics of that way of thinking and how it plays out in terms of having a background as a lawyer versus not having that background?

Stinson Mundy: Yeah. We are taught, from the time we start law school, to poke holes and problems, to think about things from various different directions, and to really think critically about every problem that comes across our desk. I know that that's not the way that the rest of the world thinks. Where I find value in this is that a problem comes across and people think that there's a solution, and it's like, “Oh, hey, that sounds great,” and the lawyer always raises their hand usually and says, “Hey, well, have we thought about this? What about looking at it this way?” Those questions that tend to get raised from our perspective are questions that nobody would have ever thought about. Some of them have to do with risk, some of them just have to do with our natural curiosity to figure out all the different pieces that are going to come together in any given situation, but that we just have this ability to look at situations differently than the rest of the world does.

When you're advising a business or you're advising a leadership team, having that critical lens on can just be invaluable because it can stop and prevent issues down the road because they're things that you have thought about. The flip side to that though is the stereotype of a lawyer who's always saying “No, no, no,” because we found all these potential risks, but that then becomes a business decision as to whether that risk is something that's worth taking. But actually knowing that something exists and thinking through critically then how we solve for that thing that we found that exists, is fascinating to me and just a skill set that we bring to the table that I don't think that we realize is actually a great skill set.

Sarah Cottrell: I'm interested to know for you what the things are that you get to do now in this role that you didn't have the opportunity to do in your various practicing roles, and if there's anything that you specifically miss or if there's anything that was particularly surprising, any of those things I'd love to hear about.

Stinson Mundy: I think the one that continually surprises me, and has surprised me as I've transitioned out of each role, is the willingness for clients to talk and engage with me. When I went in-house, obviously, I was there and clients could talk to me all the time because they were just paying me a salary, they weren't playing billable hours. Then when I went out on my own and people were now paying these flat fees and these subscriptions, they were more willing to talk. But there was still that “Okay, well, you're an attorney. What's coming out of here? Where's the big aha, I think you've got me?” It's just that fear because as a society, business owners are just so ingrained to think that attorneys are just out for their money. I think that is a direct correlation of the billable hour and how we bill, or how most attorneys bill is that there's that tension between “Do I need this advice? Do I not need this advice?”

Being on the outside, some of the stuff, some of the conversations I have with clients now are very similar to conversations that I might have had with them with my lawyer hat on. But I find when there's no lawyer hat there, clients are far more willing to talk to me, they're willing to pay more for the time that they spend with me because they don't have that stigma of “what's the lawyer getting out of it” attached to the conversations that they have with me. Even to this day, it still surprises me that stigma exists and how, when you're on the other side of it, you can see, you're like, “Wow, you could have handled this a different way if you talk to an attorney about it,” or something like that, but that they won't because they just have that fear of the cost or what's coming out of it.

Sarah Cottrell: There really is, I think, one, this sense of “Well, is it really bad enough that I need to talk to a lawyer?” which is actually something you probably should find out from a lawyer but you don't because you're trying to assess whether you really actually need the legal help. There's that piece of it. Then we could have a whole separate conversation about billables and the super problematic incentives. Actually, when we're interviewing this in a couple of weeks, I have a YouTube video releasing that's basically all about billables and the billable hour and why it's a trash system, but anyway, part of it is I think that it is rational that, at least on a subconscious level, clients feel like, “Okay, you're helping me but also every moment that you spend with me or on my case is also time that I have to pay for,” which is true in other circumstances with other professionals and whatnot, but you don't have this nagging sense of, “Well, maybe they're making it seem more complicated than it is because that means that they can get paid more.”

I don't think it's about whether someone even trusts you or thinks you're an ethical person, it's just the nature of the system that is set up. Literally, the way it's designed creates this distrust. We can go into all sorts of other things about what it does on the lawyer side, but the top three things that people talk about when they're talking about “I don't want to do this anymore,” billable hours are hands down. It just creates a bad work environment.

Stinson Mundy: Even in the world that I'm in now, we don't bill by the hour for all those reasons. When I started my firm, I was adamant that I didn't care if anybody told me it couldn't be done. I was coming up with an alternative fee arrangement that did not require me to bill by the hour because I wanted my clients to pick up the phone and call me.

Sarah Cottrell: It's interesting, I do think things are slowly microscopically shifting but I also think that lawyers need to train themselves into a new way of thinking because I think a lot of lawyers, if you operate in a billable hour model, you essentially train yourself to believe that your work is only valuable in terms of its quantity. That's not actually true, but it's the framework that we operate in that defines what is and is not valuable.

Stinson Mundy: Right, when actually, it's the knowledge that's in your head that is valuable. It shouldn't matter how much time it takes you to impart that knowledge.

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

Stinson Mundy: Just encouragement that if you're thinking about leaving or you are about to leave, go talk to as many people as you can who are not lawyers. Reach out to your network. Reach out to your friends. Set up coffees and meetings with people who do things that you don't even understand what they do or don't even think that you would be interested in, and there are so many. I've been blown away, still, about all the different types of work, jobs, professions, and companies that there are out there. Without exploring and without having those conversations with people, we tend to get into that siloed world of “Here are the four things that I think an attorney can do if they decide to stop practicing law,” when in reality, there's so much out there, and so many different industries and companies that can use our skill sets and that we can have a lot of fun with and still be intellectually stimulated and feel like we're providing value just outside of what it is that we do now.

Sarah Cottrell: I think that's so true. Honestly, I find the majority of people who come to me to work with me, they start out in “I feel like I have no options. I feel like I have super limited options space,” and then eventually, they get to the point where it's like, “Oh, I have so many options. I actually need to develop criteria in order to be able to narrow down what my options are.” I think that being able to shift the way that you're viewing your options is huge, and like you said, I think part of it is interacting with non-lawyers and recognizing, “Hey, the legal world and the actual world are not the same thing. The legal world is a small part of the whole world.”

Stinson, I really appreciate you joining me today. If people want to connect with you, where can they find you online?

Stinson Mundy: They can find me online at LinkedIn, Stinson Mundy; Instagram @stinsonmundy, or through the Envoy Portfolio website, which is

Sarah Cottrell: Awesome. Thank you so much, Stinson. It was really fun to talk to you today.

Stinson Mundy: Yes. Thank you.

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