The Sunk Cost Fallacy, Leaving the Law, and the Power of Storytelling with Shaun Bernstein

Welcome to Studying Law Around the World. I'm Claudio Claus. In each episode, I talk with lawyers, law students, and professors from different parts of the world to talk about legal education, careers, and what the profession looks like in real life. We talk about the hard parts, the surprises, and the decisions that shaped their paths. Whether you're planning to study abroad, thinking about working in another legal system, or just curious about how law works around the world, this podcast is for you. Today I have the opportunity to interview Sean Bernstein. He has an incredible story and quite an interesting business that he works on and has developed and grown. He started his career as A journalist and describes himself as a journalist turned lawyer turned storyteller. So excited to hear from you today. Thank you so much for making the time, Sean. Thanks for having me. This is, this is fun. I'm excited we get to do this. Absolutely. It's been a long time coming since we first talked about doing this. So I'm so excited to get to hear from you today. And let's dive right into that. I love the describes himself into journalist turned lawyer turned storyteller. Tell me more about this. journey of yours, you know, starting in journalism, moving into law, and then building your own storytelling agency. Yeah, I can give you kind of the quick version of it. So the time I was a little kid, I really, I had kind of 2 career paths that I was thinking about. One was journalism, one was law. And I'm lucky that I got the chance to do both. Journalism was always my first love. I started with it in school. I was doing it in high school and even elementary school. I used to go around interviewing people. I've always kind of loved, you know, playing the reporter. And I left my first try at journalism school because I took ill and I did an undergrad in English. And, you know, a little bit different. But when I was trying to figure out what to do next for graduate school, I was like contemplating law school, but I wasn't ready at that age. And so I went back, I did a journalism graduate program and I loved it. I loved every second of it. I did print and broadcast and I fell in love with radio and I just had the best time. Unfortunately, at the time I worked a lot of jobs. I wound up working outside of the field while I was figuring out my life, but I could not get anything in media. And so I used that plan B and I went to law school. And I, which, you know, people laugh. I said, how is law school your plan B, what's wrong with you? But in my case, it was. And I went to law school. I found an interest in employment law because I had a bit of an HR background and I liked people and I came from employers and I was working with employees as well. So I learned to do both sides. I did articles at a full-service firm, which was the best experience I could recommend because I was speaking about this the other day with somebody. I got a really broad-based training that a lot of people who do one sole focus don't get. So I'm grateful that I had that and I learned a little bit of a lot of things, but I always loved the employment work for a number of different reasons. I practiced for a couple of years on and off. I had kind of 2 varying stints in practice. My first one really didn't go so well. And so I had left and I was working on Bay Street in marketing of all places. And I got a call from a firm that I had always wanted to join saying, you know, if you still want us, this is the time to do it. I wound up going to them for almost a year. And I'm grateful for that experience because it really taught me that law is not for me. And I never want to practice again a day in my life. And so I left. Law really did a number on me. And so I left practice and I said, okay, that's it. I've tried this. I'm done. I was not sure what to do next. And I have always been a writer. My, I joke that my wife elbowed me in the ribs and said, you know, you're a writer, go and write. And so I didn't know if there was a business to be made out of what I was doing, but I said, hey, let's give this a shot. And that's really what it stemmed from was just putting myself out there as a ghostwriter. People knew that I could write, they knew my background. I started taking on some projects while in full disclosure, I was doing doc review, which I'm always a fan of as a way to make income if you need it. I did a lot of eDiscovery for about the first year and a half of my business. I kept doing it, but I was building this up. And now 7 years later, I have this writing business that I am as happy as I've ever been and ever thought I could possibly be. For you, was it a very difficult decision, personally speaking? I feel like for a lot of lawyers, being a lawyer becomes part of your identity and not only, you know, part of your professional sense. So that makes this transition really hard. And then when you add in the sunk cost and maybe benefits from practice salary and all those things, it makes it really a hard decision. How did you weigh in all those factors? So it's a great question that you ask, and I'm actually going to jump on one of those points first, the identity piece, because I do think that I was lucky in that sense. There are certainly people for whom being a lawyer is their whole identity. They were the kid banging the plastic gavel on their toy set, you know, wanting to be a judge. And, you know, that smart-mouthed, you know, kid who likes to argue about everything and someone says to them, you're going to be a lawyer someday. That wasn't me. Law was never my— and I joke that it was my plan B, but it was, it was never how I defined or saw myself. I came from a family where my mother had practiced for a couple of years and she left when I was born. A lot of her friends were classmates place from school who had gone on to do other things very quickly. I have an uncle who's still a partner on Bay Street in his 70s and is working harder than people a quarter of his age. And he's, you know, an absolute whirlwind and a noted figure. But for me, law was always viewed as an option of, you know, you can use this as a path to doing something else. So I'm grateful in the sense that it was never kind of how I saw myself in the mirror. And I think that made things easier. The truth is, and I spoke about this on another podcast, I had a mental health crisis. I really did not fare well. And I don't want to, you know, scare anyone or dissuade them in the early days of practice, but for me, it just was not a fit. The business of law did not do well with me. Some of the client pressures did not do well with me. The billable hour model, et cetera. I'll never blame any individual for it. This really was a situation that, you know, had happened to me. And when I left my firm and, you know, they were very good with me when I left my firm. I had kind of had that moment of, I could look to go somewhere else, but I can almost bet that this would happen again. I was not well. And, you know, as I took the time to recover, I said, you know, do I want to try this again? And I realized, no. I worked at a pretty great place. I still have some lawyers I'm very close with, but I don't think that I would have fared any better, if not much worse, at any other shop. And so it was that recognition of, wait a second, this is the time to do this. The sunken costs is an interesting one. I think if you lose sleep over that, then you'll just never get out. What I've come to show people, and we can talk more about this, but I'll say this for, you know, the newer calls who are listening, is it's a tough job. And I don't think I'm, you know, telling tales. It's a difficult job. There's hard days. There's hard weeks. Someone years ago taught me the 3-week rule that if you're really miserable for 3 weeks in a row, it's time to look in the mirror and assess. For me and what I've sort of come to, you know, symbolize and shown other people is that there is a way out. There is, you know, if you are that miserable and if it is really injurious to your mental health, it's not the only thing you can do with your life. There is a way out. There is a path forward. There are other ways to use your degree. And that's not saying to quit when it gets hard. It's going to be hard, period. But if you really are in a bad place and you think that there's no other path for you career-wise, I'm here to tell you that your brain is lying to you. And that's just wrong. And I'm happy to talk to you about it anytime. Reach out to me, please. Thank you. Thank you so much for sharing that. I've seen also some of your writing where you would encourage lawyers who are struggling to seek professional support. Kind of finish up on this subject, I wanted to ask you, is there something you wish law firms and the profession as a whole understood better about, you know, the lawyer's mental health? It's tricky. So I had gone through 2 different rounds of counseling. What you all need to know, number one, is that you have access to professional support through EAP, through the Law Society. The Law Society has the Employee Assistance Program. You know, we talk about it kind of in whisper tones because they will deal with addiction issues. And I'm grateful that I avoided those. But if you do have a problem there, those are people you can call and, you know, they'll guide you to some professional resources. But they also just have access to therapy and social workers and counselors who can do some psychotherapy. And it gets you a couple sessions, but it is a start at something. And so I did use that. Also, if you have any firm benefits, if your firm has any benefits plan, you'd likely have access to that as well. And I use both. I did 2 different rounds of counseling. The first person I saw said to me, you're not depressed, you just need a new job. And it really, you know, something to chew on because here I am, you know, 6, 7 months into working and I already have a professional telling me you need a new job. And I went, you're probably right. I don't know that I'm ready for it just yet, but in the end, that was, that was the case. I, in terms of what firms could do differently, it's very frustrating to me and still is. I was the workplace mental health lawyer who went through a workplace mental health crisis. I was an employment lawyer. I was a person who dealt with everybody's workplace mental health leaves for my clients or those clients that were really struggling. And I was someone who struggled to compartmentalize. So I'm dealing with other people's, you know, very significant workplace mental health issues. And it's starting to impact my own because I'm taking on that stress. In the profession, I still worry that it's a lip service conversation. It is something that is now more open to being discussed. There's some great pioneers who have really tried to bring it into the forefront, but I still don't think the culture of law is changing fast enough to deal with the problem head on. We recognize that it's there. We see the stats. I don't think things are really changing. I think there's still an expectation of, you know, from senior members of the bar, I suffered through it, so you should as well. I worked 20 hours a day, so you need to as well. There is some change for sure going on amongst younger members of the profession. But not nearly fast enough. We're still losing people. You know, I still see reports of young lawyers who are not making it out of, you know, their 30s, 40s, what have you. Is law exclusively to blame? No, I can't say that. I don't know these individuals, you know, stories, but I can tell you it certainly does not help when people are really struggling. So to make this long-winded answer, look at concrete actions. What can you, if you're running a firm, what can you actually do? How are you checking in with people? What resources are you providing? How are you showing that this is not just, oh, here's a number you can call, but don't ever say anything about it. How can you take this seriously? My commitment is I'm not shutting up. I'm not blaming anybody. I'm not out here to make any trouble, but I'm not staying quiet either. I, people ask me about what happened to me and I will, you know, laughingly say I lost my mind because I try to make levity out of everything, but that's exactly what happened. I had a significant mental health crisis and I'm very frank about the fact that if I had to, you know, stay 6 more months, I don't know that I would have lived. That's a bleak thing to say, but I'm also not shy about it because the silence is going to kill people faster than anything else. Why do you think so many professionals, including lawyers, will struggle to communicate in a way that actually connects with people? And how have you been using your, you know, talents and gifts to make that happen? It's a great question. Most dangerous tool you give a lawyer is a keyboard. Because if you're in a consult with a new client, in your face-to-face, you can really see them and you can really evaluate their level of sophistication. You know where that person is at. And if you're dealing with somebody who doesn't have much education or does not have, you know, formal training, you adjust your speech accordingly. You make sure you're breaking down concepts. You can gauge their facial reactions and their body language to see if they're understanding you. Lawyers are very good at that. Give them a keyboard and all bets are off. You know, we are so used to writing for opposing counsel who have predominantly the same training and backgrounds that we do. That's great. The public doesn't. The public does not. Most people who read your work, you know, especially when you read a newspaper today, newspapers once upon a time used to write to a grade 8 level, and that was sort of high sophistication. Now the common standard is grade 4 or 5. So if you're writing for the public, you're writing so that a 9 or 10-year-old can understand what the heck you're talking about. Most lawyers are not very good at that. So they wind up being too wordy, too lengthy, too complex, too opaque in their ideas. And it's really very frustrating. And lawyers are not the only culprits. I mean, it sounds like I'm picking on them, but there are other professionals as well. You know, we're used to dealing with your colleagues all the time. That's one thing. But you don't realize that for marketing purposes, you're not dealing with your colleagues. Usually you're dealing with the public. Unless you have a practice that is exclusively referral-based from other clients. And, you know, you have no website because no one else— from other lawyers, forgive me, other practitioners. And you have no website because no one else in the public is ever going to find you. And that's okay. That's fine. But that's a small handful of people. By and large, you have the public checking you out. You might have some sophisticated clients and that's great. But the reality is that busy people are busy. So even though you have, you know, a CEO, for example, who might be highly educated, who's someone you're courting as a client, they don't usually have time to read your 3,000-word blog post. Like they just don't have the time. They're skimming quickly. There is a beautiful art to clear and simple communication. How to get your point across simply. It's not dumb. It's not showing a lack of intelligence. It's actually showing a great intelligence. And how can you make the point that you want to make simply and clearly in a way that people understand? For me, I found the secret sauce of that is storytelling. You know, because stories are what sticks with us. They stick in our brain. We remember them. We relate to them. We see ourselves in those stories and we can really visualize something, especially for someone who learns visually, you can see it playing out. And so if you can use something like that as an example, you know, talking about a practice area that you serve, for example, you're probably dealing with somebody who has no idea what you're talking about. You know, if you are trying to explain, let's say M&A. I had actually a great conversation. I'm going to sidetrack for a moment with a family lawyer. And one of the pieces of feedback that she got, I think from her own relatives was, I don't need a family lawyer. I need a divorce lawyer. I'm getting divorced. I'm ending my family. That's not a family law issue. Family law is something that, you know, we think of as, oh, that's such a no-brainer, but it's not to everybody. So the things that we even, we think are simple are not always so clear-cut and straightforward. Finding the really easiest way to explain what we do and how we help people is where I come into shine. Because at the end of the day, law is so much a sales business for most of us in building that pipeline and getting clients. How do you explain to people, just because someone does not have a lot of money does not make them the wrong client or a bad client, might be one of your best referral partners. But how do you explain what the heck you actually do, how you can help people, and when? Doing that clearly Using something like storytelling is a great way to communicate in a broad audience. I love that. I really appreciate you explaining, and it's clear that stories really play a big role in your life and you're so great at telling them. I love hearing it. As someone who understands, you know, both law and marketing, then are there a few specific points that you believe lawyers often misunderstand on being wordy, but when talking about branding, when talking about networking, when talking about building Yeah, it's interesting. It really depends on sort of where you're practicing and such. I have, I've worked on Bay Street. I've worked at, you know, 2 and 3 person shops. When I've dealt with larger firms, historically, there's been a real disdain for marketing amongst some of the lawyers. Some get it and some get it completely, but some people really sort of see it as this dumbed down, watered down version of, you know, the brilliance they have to offer. And that's just not what it is. It's such a misconception that stings me when I hear that because it's not at all. If it is, it's completely intentional. And so when I am working and I do this and, you know, I have what the law degree gives me is some credibility when I'm working, you know, with lawyer clients of, oh yes, I understand the work that you do, but I also understand your clients enough to know that most people don't understand the work that you do. And so how do we explain this in ways that are really comprehensible? Your clients don't need to know everything you're doing. They're not, you don't ever want anybody to be reading your blog and then go out and think they can self-rep. That's not what that is. It's not about teaching them, you know, the secret sauce of the work. It's about teaching them enough to issue spot so that they know when they have to call you. It's the same thing we learned in school. It's that basic issue spotting. So, you know, they've got the fact pattern, except they're the ones living it out in real life. And they have to realize, wait a second. This is not okay. This is a problem. This is when I really need to call somebody. Whether they are a business owner looking for, you know, some small business advice, whether they are looking for real estate advice because they're trying to navigate a complicated issue, or they have a commercial issue or construction issue. I used to see it in employment all the time. You know, how many times have people tried to solve their own problem and then make it much worse and go, oh, I really should have called somebody. That's the nature of so many different areas of practice. And, you know, while that might pay the bills, it's not always the most enjoyable way for us to do things either. We'd much rather somebody called us for good advice early on and then acted on it versus us trying to unscramble an egg that's already fried and sticking to the pan. It's not an enjoyable way to do things. So, you know, thinking in those terms of, okay, how do I explain what I do and when someone needs to find me in ways that are really going to stick with them. It's not about what they know is one thing, but that if they're in conversation with their neighbor the next day while they're both washing their cars and their neighbor says something about, I just went through this, they say, hey, I know someone you can call. That's what a great referral partner looks like. But they're never going to say that if they don't know what the heck you do. Amazing. That's really so cool. And it's definitely, you know, giving a lot of food for thought on, you know, how you conduct yourself and how you go about keeping that image publicly. So such like an actionable way to look at it, because it's easy to say, you know, everybody gets it wrong, or, you know, many people don't understand how to do it, but rarely I hear, you know, this is why, or this is what you'd expect of it. So I really appreciate you bringing that up on the show. And I understand that The Write Stuff agency came from, you know, starting with a website, a willingness to say yes. Are there a few, you know, lessons that you learned as well from growing a business from scratch? The best lesson and the ones that I passed on, and I wish I remember who taught this to me, because the person that I always think it is says, no, that wasn't me, but thanks for the credit. I said, no, I thought it was him. It was a friend of mine, but someone said to me, from the day you start your business, 6, and I think this is true in any industry, 6 months from that day, your business will be unrecognizable from where it was on day 1. And then 6 months from that point later, it'll be unrecognizable again from where it was at the 6-month mark. And then 6 months later, it'll be unrecognizable once again. And this is true of anybody starting a new business. Things grow and change. As we just talked about before we started recording, things grow and change and pivot and opportunities arise and you learn to say yes. And suddenly 18 months in, you don't even recognize where you were at your starting point. My wife is exceptional, thankfully not a lawyer, but is, you know, a brilliant mind. She has the MBA. So she's been, you know, the one who understands business of the two of us. But she launched her own business a little over a year ago, and it's been a treat to watch Because I, she's heard me say this, but I watched it kind of play out with her in real time is that, you know, a year and a half in and she's grown leaps and bounds, but so much has changed that it's hard to recognize where you are on day one as it should be. So keeping an open mind, saying yes, figuring out really where your clients are, no matter what industry you're looking at, whether it's legal or otherwise, you know, where are your clients at and how can you communicate with them in a way they're going to understand? Connect with and relate to. That's not one initiative. That's not one medium. That's a multiple, multi-pronged effort across multiple social media channels, across multiple traditional media channels, across however you plan on doing things. How are you going to reach your audience and how are you going to keep them connected and engaged with what you're doing so they know where they need to find you? That's true if you're selling a service, selling a product, It doesn't matter. How are you going to keep people connected to what you're doing and what makes you special? Beautiful. Well, let me ask you here as well. Was that your plan from the get-go? Is it something that you're hoping to expand or knowing yourself as you do these days, you believe that this kind of business can work for a lot of people who want to have their own thing? I'm just curious because it sounds like a lot of it has to do with your personal ability, your storytelling capability, and Not everyone just is just kind of looking to expand what they got. So I'm just curious to hear your side on that as well. No, exactly. I'll tell you sort of take it back to the legal bit is the one thing that I did not want to be was a legal marketing agency. And I have great respect for them, but I've seen them, I've seen them in action and they're businesses and they usually have, you know, multiple different people under one roof and they can race to the bottom on pricing because, you know, they can pay out salaries and, you know, undercut the competition. And I just didn't want to do that. I didn't want to be in a position where I was managing multiple people. I really have done well in my career sticking to the things that I'm good at. And this is no exception for me. It's about sort of staying with where my talents are. And so for me, that's words. So all I do is words. I don't handle your social media. I don't handle your graphic design. It'll look like it was done in KidPix. I don't, you know, handle the backend of your website because I swear I'll break the internet. I'm not super tech savvy in that regard. So I'm very clear on what I don't do. What I have done is I never wanted anybody to have to go without. I don't want my client to have, you know, a great piece of content that is going onto a website that needs a new coat of paint yesterday. You know, it definitely needs a refresh or really needs new headshots, et cetera. So I have brought on a lot of partners and they're not any sort of formal partnerships. I don't have exclusivity with anybody, but I have a lot of people in my network who do the things that I don't do. Who handle web design and photography and graphic design and brand strategy and social media and PR, et cetera, et cetera, et cetera. And so I will bring them on. I had coffee with someone today who does web. I'll bring them onto projects or they'll bring me onto projects likewise. So that way, and I'm happy to make introductions and it's all always à la carte. So if you like me, but don't like them or vice versa, that's fine. You can pick and choose who you want to work with, but I'll always make sure you have a suite of Talented people at your disposal, at your availability to make sure that you can do the work that you need to do. I will digress very quickly. I had at one point considered, you know, do I want to bring on other writers? And because I was over my personal capacity and I tried to do that, I thought that my style was very easy to duplicate. Turns out not so much. So I tried bringing other writers, didn't really work. And I said, you know what, this is me. What you are paying for is the 10 fingers and my brain. That is, you know, I don't use any AI and we can talk about that another time, but it's, you're paying for me and my experience and my knowledge and my creativity. And that's what you get with The Write Stuff. I just love that you, that you have that mindset and have that clarity. I understand too that, you know, through public speaking, writing, through a podcast of yourself as well, you've become a storyteller in a very broad sense as well. And as you talk with other people and have been about your business for a few What stories do you think professionals are still afraid to tell publicly? I think professionals still, and, you know, certainly see it in the legal world, but you see it in other professions, still hide behind this sort of veneer of don't let anybody in. Don't let anybody in. You know, the top collar is always still buttoned up and personal is personal and business is business. And we've seen that that's not true. That's even in the legal world and everything else, that's just simply not true anymore. You know, legal, you had litigators litigating from their bedrooms. And I had a friend of mine who was a criminal defense lawyer who is known as the defense guy with a messy bedroom because he had his computer in his bedroom and his unmade bed made it into half of his hearings. It's like, dude, come on. That's not how you want to be known. Bless him. He's a great lawyer, but that's not how you want to be known. But truly, you know, what you realize during that, when we all suddenly moved from home, is that people are real. And they have real lives. And, you know, the kids do get sick and the dog does bark during the day. And, you know, we have other things that are priorities and interests for us. I don't think, you know, we're putting Pandora back in that box. I think, you know, we now realize that professionals are people too. So that little bit of personal business to me is never B2B or B2C. It's human to human. And we need to connect with each other because we do business with people who we know. Who we like and who we trust. Lawyers, I talk about this all the time with, because if you're at a large firm, who are they calling? Are they calling the firm or are they calling you? And when you hit the point where you're expected to start doing some biz dev, you know, at a larger firm, it comes later, smaller firm, it's probably earlier. People are going to call you. They're not going to call the brand name and expect to get someone faceless. No one's calling to ask for someone faceless. They don't call, hey, give me someone I've never heard of before. No, they're calling because they want to speak to X, Y, or Z. The relationship is with you. So letting people in a little bit as to, you know, who are you and what makes you special? Don't just bark that you're the best. No one wants to hear that. It's not about just saying you're the best. It's about showing why are you going to connect with somebody? And that comes into that personal branding work that I do. You know, why is someone going to understand what you have to offer in this? I have a financial advisor client who, you know, does the work that he does because he went through a family tragedy of losing his father young, who had no savings and he wound up having to, you know, work to support a family that he never expected to at that age. And he realized the importance of, you know, good financial management. Well, there's his superhero origin story. Doesn't make him only better at what he does. I would say it doesn't, you know, initiate any weakness, but it really gives some color as to, okay, this is why he understands this. I just spoke yesterday with a lawyer who works with a lot of immigrant populations, partially from when she was one herself. And couldn't get a job and was having trouble getting settled. And, you know, had this incredible education, but was struggling to settle in Canada and learn the legal system here. And that spurred, you know, a lot of the work. It's 30 years, but it spurred a lot of the work that she's done since. All of us have these stories as to why we do what we do. And I think they only serve to make us stronger and they make us more relatable to who we're looking to reach. Beautiful. To wrap up today's episode, I wanted to ask you, you know, for law students, young lawyers listening into this episode today, Especially those questioning whether the traditional legal practice is right for them. Is there a piece of advice that you'd like, that you could share, maybe you wish you had heard early in your career? The first one I would say is say yes to opportunities. Like we were talking about, you know, literally just before we turned the mics on, you're going to find opportunities within your career that come knocking for you. Say yes, whether it's working for, you know, a partner you didn't expect to get some work from and the ability to have a training or mentorship opportunity. My wife used to work for somebody who was a Bay Street partner that wound up buying a client's business and transformed it into this software company. Wound up leaving law and running this massive enterprise, did very well in the end because he had an opportunity that came up and he said yes to it. I've had other success stories that I've known, you know, with my personal life of people who, yes, they have the law degree and maybe they practiced. But something crazy happened where they wound up in a situation or opportunity to work somewhere or do something. And they said yes. So when opportunity knocks, say yes. The other is the piece that I'll come back to is that if it really isn't for you, and again, hard days, hard weeks, they're going to happen. If you're where you're meant to be, there's going to be some light. There's going to be some bright spots that come through. But remember, if you're not, there is a way out. And this is not the be-all end-all. It's not the only thing you could do with a law degree. There are other careers besides practice where you can make a living, which is something I didn't realize until I started getting in there. You can make a very nice living in some places and be truly happy and use your brain and your skills. That can look like a million different things, but start investigating because those opportunities exist. And if you want to chat about it, like I said, feel free to reach me anytime. I'm happy to talk. Thank you so much for making the time to come on the show. And thank you all for tuning into today's episode.