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The Wellness Docket is a podcast for lawyers and legal professionals ready to prioritize their mental health. Through honest conversations with guests from inside and outside the legal world, we explore burnout, balance, and the pressures of practice—creating space for reflection, recovery, and resilience in the profession. This is a space where your wellness is always on the docket.
Tim: [00:00:02] Okay, so I am here with Dylan Gibbs. Dylan clerked at the Supreme Court of Canada, litigated at Canada's largest law firms, and prosecuted criminal cases. He left the traditional path behind after burning out and watching too many other talented lawyers suffer the same fate. He now runs Inn Laws, a national community for lawyers, rethinking how they practice. So Dylan, thanks so much for joining me on The Wellness Docket.
Dylan: [00:00:31] Thanks for having me. I'm excited to be here.
Tim: [00:00:33] So I guess to start off, you've had quite, in your young career, you know, I would be not incorrect to say that, you know, you've worked at some prestigious legal environments. You clerked at the Supreme Court of Canada, worked at some large law firms. And then I noticed on some of your social media posts related to kind of your in-laws project, that you had talked a lot about burning out. And so I'm wondering, can you tell me kind of when that might have occurred for you? And then when did you first kind of see the signs of that kind of thing happening?
Dylan: [00:01:10] Yeah, I think as early as law school. I mean, I've struggled with anxiety my whole life since I was 17. Mental health issues and I don't think I recognized it or dealt with it properly. I know at points in my life I thought, this is… this is great. This is my superpower. This is the only reason I get stuff done, is because this anxiety demon compels me to work really hard. So, you know, in law school, I started to see some consequences. Late nights in the library. And, you know, just thought it's what everyone does. It's fine. I wouldn't have called it burnout. I was just kind of getting tired and burning the candle at both ends, in a way that probably wasn't healthy. Truly felt like there are some real signs here when I was clerking at the Supreme Court. I had my first panic attack at that time. I remember going and sitting in a doctor's office and just really not doing well with the weight of the work and how I was handling my anxiety. And again, thought, you know, with treatment and handling this, it wasn't so much burnout as much as it was really coming to a head the mental health challenges I had faced throughout my life. And then when I got into practice in kind of a big firm environment, commercial litigation, doing that sort of work. I'm not very good at setting boundaries. I take on a lot and didn't improve it at that while I was in a private practice setting. So there the amount of work just really piled up, you know, paired with some perfectionism and drive to do things really well. I also wasn't turning down work, and I was taking on too much. And I'd say that's where the burnout really came of this feeling. You know, before I was anxious, but feeling, okay, I can do this work. I'm capable of doing it. I'm just quite stressed and in a big firm environment that turned to, I can't do this anymore. I don't feel like I'm even capable of getting out of bed. Some days like this is, has become too much, so I'd say it turned to burnout around that time.
Tim: [00:03:27] Do you think it was obvious to people around you as that kind of thing was happening? Or were you kind of one of those people that hides it well?
Dylan: [00:03:38] Yeah, it's tough to say because it was also Covid. Things were, I mean, I was in environments where there was still quite a few people in office, but it was different. It was different than it was when everyone was in the office five days a week. And there's people coming around door to door all the time and seeing you. There was a lot more room to be isolated. You're not seeing people face-to-face. You don't necessarily show it as well. And everyone I think was facing challenges at that time. And so there was also this, I think, willingness to excuse of, you know, it's the unprecedented times. No one's doing well. We're all not feeling good. And so it wasn't that out of the norm for any one person to be in kind of rough shape. So, you know, I am an only child. I'm relatively introverted. I think I live in my own bubble. But there were some other factors too there where it probably wasn't as noticeable. I know for my now wife, we weren't married at the time, but she certainly would have seen the things I was going through and thought, this is not normal. This has become… this isn't regular work stress. This has gone into something that needs to be addressed. But beyond that, I don't know that anyone would have been aware, not because I was hiding it, but for a number of factors.
Tim: [00:05:03] And what kind of things did you do at that time to address it and what was most helpful?
Dylan: [00:05:10] Yeah, I mean, nothing is probably the honest answer. I, you know, I started taking medication when I was clerking at the Supreme Court, and that was very helpful. One of the things that really compounded when I started back as an associate in a big law firm environment, was that I changed doctors, and there was this thought from my new doctor that, oh, well, we'll just take you off the medication. You're doing great now. And that… It was not the play, I'll say that. That was.
Tim: [00:05:44] Was it cold turkey?
Dylan: [00:05:47] There was, I mean, some attempt to do things properly and titrated, I guess, or however it is in reverse. But yeah, there were some negative effects there, but more so I think just the, the whole sentiment, I don't know if I agree with. It was like, well, you're doing really good now, so we'll take you off the medication. But from my perspective, the reason I was doing well was at least partly attributable to the medication. So yeah, back to your question. I didn't do much at the time. I took some medication, I hoped for the best, and it wasn't until I… I think it's hard when you're in that environment where you're working a lot and lawyers work a lot. It's hard to carve out the time to make things better and to set aside the time and say, okay, I'm going to put in this upfront work now, I'm going to change these behaviours, and there's going to be some payoff down the road. And so I didn't do that. Now that I've had space as an entrepreneur to design my day how I want to fit in exercise. I think, you know, reading a few books on the subject, and making sure that I exercise way more than I ever have in my life. That's been the real game-changer. I'm now exercising, you know, 6 or 7 days a week, no exceptions. And again, there's a lot of factors going on. I can't say it's exclusively that, but boy, do I feel better when I'm exercising.
Tim: [00:07:22] Oh. That's amazing. So why don't we jump right into here? I'm interested in talking about your current project. And, you know, just to start off with this group that you've started and this idea that you've started. Community, I guess I'd call it. I saw on… I can't recall whether it's on the website or maybe on LinkedIn, where it says authentic connection with, and zero ego, right? And that really spoke to me. That's really something that I think we're lacking in the profession generally across the board. And I just why don't you tell us, how did you come to the idea to kind of ditch the private practice and move into this entrepreneurial path and then tell me kind of how that all laid out from there?
Dylan: [00:08:20] Yeah, I think paired with I mean, burnout was one thing. I left Big Law because, yeah, there were a lot of challenges there, and I didn't… I couldn't see myself doing that long-term. Went and worked as a Crown Prosecutor in Ottawa. And that came with different challenges. The workload, it was a lot, but I think it was more manageable than a big firm environment. And, but there were other aspects of it I didn't like. And so the initial thought of, I'm going to go be an entrepreneur, I'll be honest, it was. I'm not enjoying what I'm doing. I can't see myself doing any of this for the rest of my life, and I need to go do something different. And it wasn't until a process of kind of trial-and-error and testing the waters on some things that I found and identified this need for community and that, you know, now that I'm back in that… There was a point when I was, you know, at the lowest in burnt out where I thought, I don't want anything to do with the law. I don't want… I want to be an entrepreneur in something that is unrelated to law. And now I'm lucky. I'm fortunate I found this group of people who kind of think like me and who get it and who don't want the profession to operate in the way that it's always operated. And that's, it's given me a really renewed faith in the profession and excitement to be a part of it and doing something where I'm connected but not practicing.
Dylan: [00:09:54] So I think part of that, you know, part of why I didn't do well with the model or status quo is I'm a first generation lawyer. My family, you know, not a lot of post-secondary education at all. Some, you know, diploma programs, but no undergraduate degrees until my generation. And I just felt like I'm a down to earth person. I talk in a pretty informal way. You may have noticed that already on this podcast. This was how I talked in court. This was how I made submissions in court. And it just didn't. It went over well with judges, I'm not saying that didn't work, but it made me feel like an outsider in the profession, I think, in a lot of ways. This… I'm not stuffy, I don't like stuffiness, and I'm looking for that sort of human. Hey, we're lawyers, but we're humans first. And so that was one of the things that I think pushed me away from practice. And, you know, I started just writing a newsletter and the thought was, I can write about what's happening in the law at the Supreme Court, at Courts of Appeal, and I can just write about it my way. A little bit of humour, some plain language, distill things down. And, you know, maybe no one out there wants that.
Dylan: [00:11:22] But if people do want it, I'll at least get the reassurance. Hey, I'm not the only one that thinks the way we talk about the law, the way we talk to one another is odd in this profession. Overly formal in an unnecessary way, and in a way that kind of separates us from one another as humans. And so, I started writing that newsletter and it grew to 6500 people or something like that, where there was just a real indication of, okay, I'm not the only one. There's a bunch of people out there who want to talk to each other in a more human way, and that's what led to this community concept of, well, why don't we bring these people together? Why don't we give them the tools to help one another through practice to, you know, talk openly about issues like burnout and mental health and, you know, on a business ownership side for firm owners, bring them together. Talk about how to operate your firm. Do all of the things really that law school doesn't teach you and that you might want to connect with peers about. And so I was able to see that from the newsletter audience. And now I'm just excited to be a part of it and connected to those people who see things the same way that I do and who get it that we're humans, then lawyers and not the other way around.
Tim: [00:12:39] Yeah. And it's kind of like something that resonated with me. My last guest basically said, I'm the same person, when I'm walking my dog as I am when I'm at my office. Right? And that kind of, you know, not to be, not to say that the law is not a serious thing because the subject matters we deal with and the clients that we deal with are serious, but we should have some ability to be ourselves and be human beings as well. And sometimes I felt like, that it doesn't always allow for that. Right? And, and I think that's maybe that's one of the big reasons why we're seeing some of the struggles that we have, because why are people going to work every day and being somebody that they're not. Right? Like, and it just doesn't make any sense.
Dylan: [00:13:30] Yeah. No, I completely agree. And I think there's, you put that kind of facade up. And I agree with you that it has to be done in certain contexts. You know, I was writing a newsletter with some like jokey humour and quips in it. I would never suggest that people write a demand letter or to a judge like that, right? But sometimes you're emailing opposing counsel, and it's not the sort of email that's going to end up in the motion record and be used against you. And is there any harm in saying, hey Doug, you know, hey Jane, here's what I'm thinking. Can we hop on a quick call as opposed to the Jane, comma, you are being unreasonable. Like, it just… it sets a certain sort of tone that we don't behave like… We don't talk to anyone in our lives like that. And I agree with you that to some extent, that adds to the situation and the crisis we're in mental health-wise, when you it's so, kind of, not how you operate in your day-to-day life. You have to be someone completely different in that office setting.
Tim: [00:14:40] Right. And I think some of it comes from expectations. I mean, there are there are massive expectations, possibly because of what people see on TV and possibly just the way they expect things, that they think that well, if you make that polite phone call to that other lawyer, I'm not getting my money's worth because you're not, you know, being a pitbull at that very moment. When in fact, what you realize is it's actually the complete opposite. It is so much more productive. But… so let's… I want to get into the, first of all, just to go back to the concept of Inn Laws, because it certainly got me thinking here. Tell me about like, when you first came up with this idea and was it… did you pitch it to your then wife and a couple of your friends? And how did that go? Because, like, for me, like anybody who's doing anything, you're even doing this podcast, you know, you're there's a moment where you're like, I think I kind of like this idea, but I'm kind of scared to communicate that to somebody. And then what were the first reactions?
Dylan: [00:15:49] Really fortunate. I went to a conference earlier this year for people who have newsletter businesses, and there's kind of a pioneer in this space. His name is Sam Parr, and he runs a podcast now called My First Million. It's a great podcast for people who are business-minded and entrepreneurial. And my wife turned me on to that years ago. I had been listening to it a lot, and it was one of the reasons why I quit my job to write a newsletter, because I saw, okay, this is a model that's been done in other spaces. You can write about things in a casual way and find a way to turn that into a full-blown business. So I went to this conference and it's at a time in February where I was struggling to write the newsletter. Honestly, I had kind of started burning out again, but in entrepreneurship. And I think a lot of that was because I was really isolated. I was working on my own to produce this work product that was now being read by thousands of lawyers and judges, and the weight of that, in my mind, started to become way overblown, just overthinking every piece of work that I put out. And with no one to talk to about it, right? Completely operating on my own. So I was struggling a bit. I went to this conference and, and Sam was one of the speakers there. And what Sam is doing now is a community called Hampton, which is for high-net-worth CEOs, founder types. Very high-net-worth.
Dylan: [00:17:23] It's a very prestige sort of community. But he talked a lot at the conference about the value of community, why people are looking for community now and the importance of it. And something really clicked for me of, you know, yeah, that's right. And I think lawyers would want a lot of this stuff too, and it would give me an opportunity to solve a lot of the challenges for me personally, the isolation of writing a newsletter by myself. This is a chance to really connect with my audience and, you know, do something for them that is not just bring a smile to their face. It was rewarding. I like writing a newsletter and get the feedback from people, but there's only so much you can do by putting an email in someone's inbox, and there's a lot more you can do when you're connecting them and having peer groups and hosting events for them. There's a lot more you can do. So I heard his words at the conference. It was great. And then my wife and I happened to be waiting for our Uber outside the hotel, and Sam comes out and he's also waiting for his Uber. And so we ended up, the Ubers took forever. We ended up having a 15-minute long conversation with him just saying, hey, look, this is the situation. I have this audience of lawyers and I think the community thing could be really neat. I'm intrigued by what you said. I told him I have all these beliefs about it. Lawyers aren't going to set aside the time to gather in a community and to chat with one another.
Dylan: [00:18:48] This is a tough audience. And, you know, like I said, I was really fortunate. He just, he looked at me and said, that's a limiting belief. You have to go out there and try it. And what I would do is, if I was you, is pick up the phone and call, you know, ten, 20 lawyers and do some investigating. Ask them some questions and figure out whether this is something they would use. And, you know, if they, if the answers aren't good, then there's your answer. But if you start hearing things that suggest people would like this, then you're off to the races. And so that's exactly what I did. My wife and I put together a set of questions that I could ask people that weekend, that trip. We were in Austin, which is where the conference was put together, a list of questions. I emailed some of my most engaged newsletter subscribers, people who read it every, I mean, by that time I wasn't putting it out as consistently as I was when I started. But the people who read it the most emailed them and said, you know, would you hop on a call and just chat about stuff? I was very vague. I didn't tell them, I'm starting this community. I just got them on a call and said, how are you networking? How are you connecting with other lawyers? What's missing for you? And I heard so many of the same things. Covid has kind of shattered in-person networking. A lot of it hasn't come back, and I'm missing that.
Dylan: [00:20:06] The education events I go to feel very stiff and not practical. I'm getting a lot of lectures about stuff that I can't take away and use in my practice. And I love some of these forums. There's Facebook groups for lawyers. I love aspects of that. But the, hey everyone, come on in, this is free, leads to not the best high-quality discussion. And so that really shaped the model here, where it's a community of people that I interview beforehand, talk to, make sure we're aligned, and there's some buy-in to the values of what we're building. We have in-person events that bring people together in a more casual way, where I'm doing the job of facilitating discussion and connecting people to one another. And we do education events that are really rooted in my now two years of experience being a content creator. It's practical to the point, you know, I go on YouTube. I can spend hours learning stuff about sales or any other topic. Why shouldn't lawyers be able to find that same content? Right? And so that's what drives a lot of our content. And yeah, I'm really fortunate. I'm fortunate that I ran into Sam in Austin. I'm fortunate that my wife works in tech and knows so much about interviewing the users of a product and shaping a vision for a product before you just throw it out to the market and say, hey, does anybody like this? And because of that, I was able to really take a deliberate approach, and it's paid off.
Tim: [00:21:45] Here's, just I have to ask this question because it came into my mind, not to get hokey, but do you think that was a coincidence?
Dylan: [00:21:56] Yeah. My...
Tim: [00:21:58] I’m sure you've heard I'm sure you've had that same question before.
Dylan: [00:22:01] Yeah. Well, so, I'm a very non-spiritual person, I would say. And I don't look for signs or identify signs in anything. But if there ever was in my life, that was the moment. And, you know, my wife sure does. Her takeaway from that. Now, it's funny because we went to that conference and, you know, we'll say it was life changing. For me, it was life-changing. And earlier, you know, later this year, it's all the same year. But in October we went to a conference for her work and we joke... She said, well, how is this going to change my life? And at first it was…
Tim: [00:22:39] You set the bar too high.
Dylan: [00:22:41] Yeah. Is that the bar for professional events? Now it has to be life changing. But it's amazing what happens when you go in with that mindset. Because we went to this conference. I mean, she went, I was just hanging out in Vermont, enjoying the scenery. But she went and she went with that mindset of, how can this conference change my life? Her takeaway from it was that the people speaking at the conference, you know, are going through a lot of the same things she is, but they have a social media following. And so her takeaway is I'm going to post on LinkedIn more, I'm going to be active and I'm going to see what comes from that. And she's blown up. She's like a certified marketing influencer these days. And so I think it's really neat that going in with that mindset allowed that outcome. I mean, I'm going to approach more things like that now, and I know she is, of how can this change my life?
Tim: [00:23:39] Yeah. And like, when you.. I kind of got goosebumps when you said the line about the limiting beliefs, because haven't we all thought that at some point in time? Where we've spoken and we've said something and before we've even taken the first step, we've already convinced ourselves that, you know, why should I do this? And how is this a good idea? And I don't know about you, but I've just learned to stop doing that. Like, just start… Keep taking the next step. Keep, keep... If it sounds like a good idea, as long as your family and your friends aren't telling you it's a terrible idea. Keep going.
Dylan: [00:24:16] Yeah. I mean, I think that's a great way to do it. Easier said than done. I don't think I'm all the way there yet on perfect, but a book I recommend to people is The Courage to Be Disliked. It's a pretty easy read. It's about a school of philosophy, Adlerian psychology and philosophy, psychology. I don't know. It's kind of both. And it just talks about stuff being not your task. There's things that are your task and there's things that are everyone else's task. And your tasks are the stuff that is within your control. You can show up, you can put in all the effort, but how other people perceive it, and certainly you thinking in advance, how are they going to perceive this? That's not your task. And so that's become another kind of common phrase in our household is, that's not your task. And just a reminder, exactly like you said, to keep going and not talk yourself out of things or do that mind-reading exercise before you've even gotten off the ground.
Tim: [00:25:21] Right. And so tell me a little bit about, how long? First of all, how long has Inn Laws, this group been going and then after that, not to do a compound question here, but after that, what are some things that have really surprised you or have stuck out to you during your time managing this community?
Dylan: [00:25:47] Yeah. So we've been officially launched since the start of July. So it's… I mean, we're coming up on six months here, and so it's new. It's relatively new, and it's been exciting to see how it grows and what people want from it. That’s changed the initial vision a lot. And because it's new, it's been really exciting to just go with the flow and see what people want out of it and, and make it so. I think one of the most surprising things for me has been the breadth of appeal in terms of different practice settings. I had a vision when I was starting this that it would appeal most to people who are business owners or in a small firm environment. And, you know, kind of a, we're banding together. We're giving ourselves the resources of a large firm by working together, talking to one another and sharing things. And that's true. I mean, definitely those people have been some of, like one of the largest segments of our membership.. I’d say firm owners especially. But it was one of the first conversations I had after I announced, hey, I'm doing this was with a partner that I worked for when I was articling and then as an early associate. And I think my email tour was kind of dumbfounded, like, hey, why would… why are you interested in this? Like you work at a big law firm.
Dylan: [00:27:32] What does this do for you? And it was really interesting hearing, like look, you get to this point where, yeah, you have partner in front of your name, but no one teaches you or talks about, hey, how much detail are you giving to associates when you delegate work? How are you dealing with these difficult client challenges? How are you managing the conversations around the partnership table about compensation and all the non-billable stuff you're doing on top of your hours? And so that was really eye-opening for me, that really, no matter where you're at and what you're doing, there's value in coming together with people who are going through the same stuff, people who get your challenges. And discussing that with them, as opposed to trying to solve that all on your own. And I think the mind-reading thing we just talked about, you're so much more likely to do that when you are working in isolation and living in your own head. It's easy to spiral and let the thoughts kind of build up of like, should I be doing this? Should I not be doing it? What will other people think? What are they going to say? And it's amazing how much of a shortcut it is to talk to someone who's in the exact same spot as you, or roughly the same spot, who's been through those challenges and say, hey, what do you think about this? I see you've run a podcast before.
Dylan: [00:28:59] How's that working out for you? Do you think I should do it this way or that way? Right? As opposed to all of the thoughts that go through your mind when you're working that out on your own. So that's been one of the coolest things for me to see. We have a peer group meeting next week that is a bunch of Big Law partners and people who are kind of at that, either on the cusp of a partnership or are partners, just coming together to talk about those issues. And then we have a group of junior associates on the other end of the spectrum, coming together mostly to commiserate, but to say, you know, how are you guys dealing with, how are you handling this in your firm? And it's been cool because for that group, you know, I don't know that I have much to offer the partners other than the occasional book recommendation. It's more just sitting back and watching them share with each other. But for the junior lawyers, I do have some stuff I can offer from my experience, and that's been fun too.
Tim: [00:29:51] Yeah, it's pretty neat to hear how those different ranges of people in their careers are taking to that. And I wonder what your thoughts are like, does it have anything to do with the fact that maybe we're more willing to talk with some of those people that we don't know as well, right? Like you get a community group, as long as it's safe, I would put it that way. And I think that's the risk of the online Facebook group or just posting in a random group is because you don't want to be singled out and can't believe Culbert asked that question, for example. Right? Like, that's... And I think that going into that kind of group and knowing that it's vetted that way gives people that confidence that, hey, I can just speak my mind here. Because I'm sure it's hard for for some of those partners to admit. Even they weren't taught certain skills in law school. Right? And, and we're all just kind of learning, and I, I know it sounds cheesy, but that's why they call it a practice.
Dylan: [00:30:59] Yeah. No, it's true. I think it's funny. I'm just this is my Sam Parr hype podcast, but he literally posted about this yesterday because he's doing kind of a similar thing. And he talked about how it's important to have the three C's and to be explicit about it. So there's a commitment to the group, there's confidentiality, and there's candor. And that's what really drives, kind of, the good conversations. And the way you do that is through a vetting mechanism, through shared values. And I think part of it, I was lucky that I had this newsletter audience to launch the community on. People had been reading my writing for a year and a half. They knew my vibe. And a lot of the people who joined the community early on just said, if this is other people who like your writing, I think I'm probably going to like them. And they were right. It was just a bunch of people coming together where that human approach to legal information was kind of the unifying thread. And those all, it turns out, are pretty good people. So that helped. And then another thing we do in the community, we have community guidelines that everyone agrees to when they come in. You know, it's not a place for political discussion. It's meant to make people better at practicing law and enjoy their careers more.
Dylan: [00:32:26] So there's rules around moderation. There's rules around confidentiality. You know, nothing leaves the group. Information leaves the group. Nothing that would identify anyone who said it leaves the group. And it does create that safety. I think, look, as far as the vetting goes, I'll be honest, most people who read the website, if it appeals to them and they get on a call with me, I tend to like that person and realize they would be a good fit. I think the way the community is described and the benefits that are offered, there's only a certain type of person that even wants that, and that tends to make it a good fit. So the screening, a lot of the heavy lifting on that is done by the description of the community. There's, you know, there's been a few calls where people, it just doesn't work out for one reason or the other. But, a lot of the hard work on, okay, these are a group of like minded people coming together is done by just being very explicit about what the community is and what it isn't. It's not an open place to chat about anything and everything. It's a place to, you know, be open and have those candid discussions that don't happen elsewhere and help each other become better and happier lawyers.
Tim: [00:33:44] Thank goodness, because I don't know about you, but we don't need more political conversations in this world, right?
Dylan: [00:33:50] There's plenty of room for that. I know a lot of people would say LinkedIn isn't the space for it, but people seem to have no problem doing it there. So yeah, we don't need another one of those spaces. And, you know, it's… I think people would say this about when you're putting any product out. And it's something that I lost sight of when I was writing the newsletter. You can't be everything for everyone. And so being explicit about what you are not doing is just as important as thinking about what you are doing. At some point I'm writing a newsletter. I thought, I'm writing a newsletter that has to appeal to every lawyer in Canada, which is ridiculous. It's an impossible task, and that's how you're going to spin yourself into like, just a nightmare situation every time you go to press send. Okay, will all 6000 of these people enjoy reading this? No, they won't, and that's not a problem. And so with the community, I've been a lot more explicit of, you know, this is what it is. It's for a certain type of person. That's not everybody. And by the time people make it to the point of joining the community, they know they're going to be welcomed by a bunch of other people who feel the same way about practicing law.
Tim: [00:35:04] It's interesting. I was thinking, my analogy when I was hearing you talk about this and writing the newsletter. I'm, for example, I'm a music nerd. And when you were talking about that, I was thinking, oh, well, Dylan did really well on his first record, and now he's trying to capture the magic of the first record. And you, you often fail when you're trying to do that, right? Like, you cannot, if you're just not being authentic and being yourself and you're thinking about what everybody else wants or thinks, you're never going to communicate to those people that you want. And I don't know about you, but I've had to come to that conclusion, even in doing this podcast, even in practicing law and in life in general, that, you know, you're definitely not going to please everybody and there's no point in even trying. So you just do what you got to do and, and hopefully people enjoy it and get something out of it.
Dylan: [00:35:59] Yeah. No, that's exactly right. You know, at some point in newsletter writing, I would get some negative feedback and I would adjust and change things that I'm doing. And, you know, when I step back and I think about it, do I need those people reading the newsletter? Were they ever like… Obviously writing a newsletter was meant to be a business. There was some way I had to monetize the audience, whether it's by selling advertisements or by selling a product, or by creating a community that is then, you know, shown to the audience. And so those people who gave negative feedback, which was rare, but those people would have never… they're not the sort that would have bought anything I had to offer. And so why? Why adjust for that? Right? It's better to attract the people who are on your team, who are part of your tribe, and see the world the way you do. I'm so happy now. The people I spend time with who are part of the community. You know, I just got off... We did our first monthly tech session where we just talk about, I do a demo on AI and tech, and then we stick around and chit chat about what our problems are people are facing.
Dylan: [00:37:16] And it was just awesome. It's just great people who are thinking so intentionally about the law and practice and it's conversations I was never a part of. In fairness, you know, it's not like I was practicing for years and years and years, but I wasn't a part of this sort of conversation when I was practicing. And I think it's so important. And I get so much energy from being around people who are… who view it the same way I do, that there's a better way to be doing this, that we should think intentionally about how to make our practices better. And it's awesome when you're surrounded by people who… I don't know. It's weird because it sounds like I'm saying find yourself an echo chamber and just live in it. But it's not about that. There's a diversity of views, but there's a shared value of, we should think intentionally about how we practice, and we should be kind to one another. Stuff that for me is, I don't think should be up for debate and I don't care to associate with the people who put those things up for debate. And I'm fine with that.
Tim: [00:38:24] Right. And that must have… Was it something at University of Alberta Law School? Was that something that you had to worry about? I, you know, I've heard the nightmares about students. I don't… it… the law school changes, but the students who rip the pages out of the books, they don't. They don't. So the other students can't… Like, was that something that you worried about at that time?
Tim: [00:38:45] No. Definitely not. There was, it was almost as much of a joke as the unprecedented times comment that U of A was the collegiality school, and it's so collegial. But it did feel like that my whole time at law school. Everyone was friends. I'm still close with virtually everyone in my law school class. It was like 180 people. I feel like I could reach out and ask most of those people for anything. Several of them are members of the community, part of Inn Laws. And so, yeah, very collegial place. Never felt that way. And… I don't know, I've never really felt that overly competitive sense. Honestly, I've felt that some lawyers are more prickly than I want to associate with, and some lawyers aren't willing to set aside the time to make things better, to work on themselves and their practice. They’re content just plodding away and being overwhelmed by the day-to-day work of being a lawyer. And that's fine. I mean, it's… there's challenges, but that's not my sort of people. My sort of people are the systems thinking, I want to improve. I want to be better. How can we do this with, whether it's technology or workplace policies that make things more balanced and healthy? How can we think about things a little bit differently so that we don't have a profession where the majority of people, when asked, would tell you they've thought about quitting being a lawyer entirely and that they're stressed out a majority of the time. Like, how do we make this a profession where that's not true?
Tim: [00:40:27] Yeah. And the scary part about that is that's not a small number. That's not a small percentage. And it's surprising when you have candid conversations with certain people and you kind of think, well, you thought that too? Yeah. Yeah, I thought that. And then you kind of realized, well, we're not all alone in that regard. We've all had that kind of thinking. And I think that's the inflection point that we've been at for a while. To say that there's some things that we're really doing wrong in the profession. And how do we get that right? Now I don't want to go all doom and gloom on it, because there's a lot of, it's a good gig, but there's some parts that are very difficult.
Dylan: [00:41:08] Yeah, yeah, it is, it is tough to manage. There's a lot of aspects and I think there's a lot of things that make things worse than it needs to be. And so, coming together and talking about things is kind of the least you can do as a step forward. You know, it's not going to get better if we don't talk about it. And there's very few places where lawyers are coming together and talking about things really openly and candidly. I think another benefit I have now is that I'm not practicing. I might be doing some freelance work soon working for other lawyers, but I can be a lot more candid. I don't have to worry about the regulator or going and appearing in front of boards. I don't… I'm not applying to be a judge, ever. So I don't have to worry about being disqualified for mental health reasons. But it's an unfortunate reality that a lot of the pressures that are put on this profession prevent people from being open and candid and having those discussions. And so I think the more we can create spaces where people can open up and talk about things and not feel like there's sort of a sword of Damocles hanging over them at every moment. I think that's what we should be doing.
Tim: [00:42:24] And so I ask this of all people, if there was one thing that you could change about the legal profession regarding mental health, what would that be?
Dylan: [00:42:39] I do think if it was one thing, it would be the open discussion about these issues. And it's progressing. We're getting more and more of it. There's books on it and people are talking. But I still think there's an overwhelming stigma there and a thought that if I open up about these things, I'm limiting my career in any number of ways. Right? I think someone posted about this recently. I saw it within the past year year. So think about the judicial application and screening form expressly asking about mental health challenges. And you just wonder, like what does… what is the effect of that? If people are thinking, I need to hide depression, anxiety, things that an overwhelming number of lawyers suffer from, how can we improve? How can we look out for one another if we can't talk about those things? So that's probably the biggest thing. I think, you know, if I went down to number two, it would have to be something about just the pricing and the way we structure our work. The billable hour model is… I know it's tough to get away from, especially in a litigation context, but the incentives don't make sense. And it creates a situation where people have to just work more hours to make more money, and that contributes to burn out, I think. Significantly. That you have to… There's really no escaping the fact that you're trading your time for money unless you bill using a different model. And how can you feel like you're financially free and independent if you are just working more and more in order to earn more?
Tim: [00:44:29] Yeah. And sometimes I've found with that model, I found some of the best work and the most happiness when I step outside it. And especially when it's appropriate if you can do a file for a flat fee, as long as client and lawyer both agree to that and you understand what the what the what the scope is and you've, you know, you know what your engagement is, within that, you… it gives you the freedom to do some of the deep thinking and the work that you need to do. And I find the work product would be better in that, in that regard. Or it often is better because you're not so strapped to say, like, you know, I have to get this done within this period of time. I've got to follow this billable model because, you know. But I think the hard part is there seems to be that perception of what a lawyer is. And in order to be what the perception is, you've got to build all kinds of hours all year and make a ton of money. And it's flashy and it's whatever. And I've really found more happiness stepping away from that as much as possible. Doesn't mean you still don't do it, but it's certainly something that I think we're finding more ways to be creative.
Dylan: [00:45:46] Yeah, I think that's one end of the spectrum, you know, earning a lot of money and being flashy. I think the other end of the spectrum is almost just as harmful. And that's this idea that we are purely servants of the justice system and making things fair and equitable, and that it would be unfair to sort of profit for your services or run an efficient business. And I think that we do not only ourselves a disservice by looking at it that way, that okay, you charge a flat fee and maybe you work less hours than what you would have in some alternative reality, and so you make a profit. We're not only doing ourselves a disservice, but we end up doing clients a disservice because those innovative models make things more affordable. And, you know, on average, it's not like you're out there gouging people. Like, that's not the recommendation, but there needs to be some view of like, this is a… it's a business. It's an occupation. You are… you have to earn a living. And of course, we all know we're part of the justice system and that comes with ethical obligations and unique constraints. But at the end of the day, it's, you need to earn. And there's ways to do that ethically while still recognizing, okay, this is this is a commercial enterprise.
Tim: [00:47:14] Absolutely. Well, I just want to thank you Dylan, for joining me on this podcast. And I guess I'd put it back to you. Do you have any last words that you kind of want to leave with the audience and viewers about your group and the work that you're doing?
DYlan: [00:47:32] I think the only thing I'd say is if you're the sort of person who's thinking about things a bit differently, if you're wondering, hey, where can I go to talk about tough challenges like burnout, how to manage the work of being a lawyer, how to run a business, how to do all of the things that they don't teach you in law school. If you consider yourself a human first and then a lawyer, check it out. We should connect. I'd love to chat with you, because there's a whole world of people like you out there. Sometimes it feels like they don't exist. You know, I've talked to people ready to walk away from practice because they just feel so alienated from the stuffiness and the contention of practice. But there's a whole world of people who are doing things differently and approaching things really intentionally. They get it. And they're banding together to do something really cool and fun. So yeah, connect. I'm on LinkedIn. We're at InnLaws.ca with two N's. Check it out.
Tim: [00:48:40] Yeah, I'm actually likely going to do that sometime soon.
Dylan: [00:48:44] Cool. Well, I appreciate you having me on, Tim. It’s been a lot of fun chatting with you.
Dylan: [00:48:49] Thank you.