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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] So I am here with Erin Cowling from Flex Legal Network, and I'm really appreciative, Erin, that you've joined me today on what will be this episode of The Wellness Docket. And I'm hoping that we have a good conversation about your past history in the legal field and why you decided to do what you're doing. So, first of all, as a point of introduction, why don't you just tell us a little bit about your backstory and what led you into Flex Legal, which is a freelance lawyer company? I assume there's some stories there that are important for our listeners and viewers to hear.
Erin: [00:00:39] Yeah, for sure. I'll try and condense it. So I left law school thinking, like a lot of people, I should go to Bay Street and work at a big firm. So that's where I started off as a corporate commercial litigator at a large firm. I was there for about seven years, and then I decided, I thought maybe a smaller boutique place would be a little more suited for me, and I decided to go from corporate commercial litigation into a state litigation, not really thinking of the ramifications of the switch in practice. I was doing estate litigation for about seven months, and I tell people it's probably about six months too long, till I found myself one day walking to work and this sports car came speeding around the corner. And as I was crossing the street and I thought, the first thought that went in my head was, I hope this car hits me. Doesn't kill me, but injures me enough so I don't have to go to work today. And that was kind of the alarm bell that started my whole career change.
Tim: [00:01:44] And what year? What year was that?
Erin: [00:01:46] This was 2012. So I'd been in practice since 2005, so it was a while ago, but it also, it wasn't the first time. Like the week before or a couple weeks before my toddler had an awful, you know, stomach flu. And I was getting him to, like, kiss me and breathe on me because I thought, oh, if I'm vomiting, at least I don't have to go to work. Like, these were not healthy thoughts, but at the time I just thought, I'm not a quitter. I was kind of taught, once you commit to something, you have to see it through. And I'd only been at this job for a few months. And, you know, A-type personality, like, I'm a tough lawyer. I can make my way through this. I can just cope and go through. But then about a week later, I found myself in bed and I just could not get up. I was just crying. And I called my family physician and I just said, I don't know what's wrong with me, I need an appointment. And the receptionist was very kind. She's like, I'm going to fit you in today. And I remember just bawling in my doctor's office going, I don't know what's wrong with me. I have no idea. Like, this isn't me. And she looked at me and she said, Erin, this is what anxiety and depression looks like. And it wasn't until I had the permission from another person to get out of the situation, and I quit my job the next day, and I haven't been a traditional litigator since.
Tim: [00:03:16] So how long did you take between quitting that job and kind of deciding to go out on your own, and then tell us a little bit about the steps that you took. Because it's pretty incredible to to kind of start this niche business that is so impactful. You know, I'm sure you were pretty scared at the time, though.
Erin: [00:03:36] Yeah. So I didn't wake up the next day going, oh, I'll start a freelance lawyer business. The way this all came about was I had two young kids at home. I found out I was pregnant with my third and I thought, well, no one's going to hire a pregnant lady, so I'm going to be home for a little bit. But I just, I needed something to keep my brain active. And, I realized it wasn't the law that was causing the depression. It wasn't the work. I'm a litigator who hates conflict. And so, being at home, I thought maybe I can help other lawyers that I know, just for, you know, a few months, until I have my baby and I can go back to working full time, maybe I can help them write a factum if they need help or something. And the whole point was this going to be a stop gap measure. And I thought, well, if I'm at home writing, I don't have to deal with the conflict of the clients. I can just kind of work when I want to work. So I sent out, because at that point I'd been practicing for about seven years and some of my friends had started their own practice. So I just said, look, I'm home. I've got seven years of big law experience. Do you need help with anything? And so I helped one write a conference paper. I helped one with blog posts for her website.
Erin: [00:04:42] Another one I did help with researching and writing a factum, and so, it really was just supposed to keep me busy while I was pregnant. But then my daughter was born, and after a few months, every time I went to apply back true to a traditional law firm job, my stomach just would like go into knots and I just… I would miss deadlines for applications and I never miss deadlines. I am not a person who misses deadlines, so I saw that as a sign that I wasn't meant to go back to traditional law. And then I just said to my husband one day, I said, I wonder if I can just do this as a career, like just keep helping other lawyers. And this was 2013. So at the time, freelance lawyer wasn't really a thing in Canada. Yeah, we had, you know, research lawyers who would help kind of, but not that term wasn't really well known. It was really big in the US, Australia, and UK. So I did some research and I thought, you know, people are doing this and people have been doing it for a while. So I just called myself a freelancer, put up a website, Cowling Legal Freelance was the original solo practice that I had. And then I just hit the pavement and started going to where the lawyers were and just explaining what I did.
Tim: [00:05:59] Right. And then I'm sure at that time you were probably overwhelmed with the amount of people that said I could use that service, right? Like...
Erin: [00:06:08] Well, I gave myself a goal of finding one new law firm a month to work with as a client. And by the end of the first year, I had 12 law firms I was working with on a regular basis, which was plenty for me because it was constant work, like, some would give me, you know, a few… I call them projects. A few projects a month, and others would be regular stuff that was coming in all the time. So yeah, it wasn't… the biggest hurdle was just explaining how I could help and that it was okay by the Law Society. I think some people thought, oh, but you're not an employee. And I'm like, I'm an independent contractor. You can, everything's fine. I'm a licensed lawyer. I'm insured. I'm covered under all of the, you know, professional responsibility. And so, once I explained all that, it was fine.
Tim: [00:06:56] And so do you recall what year that was when you started the, just the Erin Cowling? Yeah.
Erin: [00:07:02] 2014. 2014. Yeah.
Tim: [00:07:04] Okay. And then how long did it take for you to move that into Flex Legal?
Erin: [00:07:09] Not very long. As of 2015 I was kind of drowning in the work and I need more help. And so I decided to take it away from a solo practice into Flex Legal. So Flex Legal started in 2015. More of a kind of a side hustle. I would, still 90% of me was… my time was working on Cowling Legal stuff and then Flex Legal was kind of growing, adding a few more freelancers, getting them work, thinking of it as kind of a separate business from what I was doing. And then just over the last ten years, it's slowly morphed from like 80% me, 20% Flex Legal to 50/50, 80/20. And now it's, I'm not even practicing anymore. I'm just running the platform.
Tim: [00:07:53] I mean, that's that's incredible. And so can you tell us a little bit about what kind of services Flex Legal offers, and then maybe some of the responses you've heard from lawyers on how big a deal that is to help them in their day-to-day practice.
Erin: [00:08:09] Yeah. So, majority of our freelancers are lawyers. We do have law clerks and paralegals as well. Because I'm a litigator, it was easier to build up the litigation practice. So about 80% of our work is litigation-based. The other part is about 20% is corporate commercial. We help solo, small, large law firms, in-house legal departments with anything that a traditional lawyer can do. And I think there's a bit of a misunderstanding that freelance lawyers only do like document review or research work. That's not it at all. We do anything that… so coming from the Bay Street firm or coming from actual practice for many years, we know how to do everything. So we help with trials. We help with litigation strategy, factum writing. We do do the research and factum writing, but I feel like the research may be going a little more the way of AI if, as things move ahead. Witness prep, anything that a traditional lawyer can help with. Sorry, I forget the second half of your question.
Tim: [00:09:11] Yeah. And just what were some of the responses? Or have been like, what do you hear from people on the ground? Because I think that's really where one of the biggest connections comes from.
Erin: [00:09:20] Yeah. I feel like my day is always made when I have a lawyer who's used one of our freelancers. Just say, something like, I was able to go to my daughter's holiday concert that's in the middle of the afternoon, and maybe people don't normally can take the afternoon off because your freelancer did this for me. Or I was actually able to take an entire week off on vacation, which I haven't been able to do for years, because maybe they're a sole practitioner who, their clients are very demanding. So things like that, just those. That's the reason why I do this. And this is what one of the reasons why I do this and one of the reasons why I think Flex Legal has been so successful for ten years is not only do we provide a flexible way to practice law for the freelancers who join us, but it's also very flexible help for the law firms who hire our freelancers as well.
Tim: [00:10:13] Yeah, I mean, I can speak from personal experience with it. It's just been an incredible resource at the times when you've got certain things that need to be done right now. You don't necessarily want to hire someone full-time for it, because it's not that way all the time at the year, but it's an amazing kind of release valve, if you will, to get certain things finished in a timely manner without burning yourself out.
Erin: [00:10:40] Exactly. And there's there's some sole practitioners who have no desire of growing a law firm, but they just get too much work, like surges in work. And so that's where we come in. Or there's people who do plan on building their practice, but they don't have enough work right now for a full-time lawyer. So what they'll do is they'll use our freelancers until they get enough work, then they'll hire a full-time associate, and then we might not hear from them for a few years until their work gets really busy again. And then they hire one of our freelancers. But it used to be, I think, as a sole practitioner who didn't want to hire, you either had to turn the work down or just work constantly if you had those kind of surges in work.
Tim: [00:11:24] Yeah. And there's no shortage of work. That's the hard part in this business that I, and I don't know if anybody could ever have prepared me personally for how busy the practice can be. Right? I mean, it can, if you're not careful, it just kind of takes over and you have to really manage your time effectively. And obviously you've got all these competing pressures. And so, it's just incredible. How have things changed for you, first of all, with your own mental health, what you're doing? And then have you seen the similar change for some of the employees that work for you?
Erin: [00:12:05] Mhm. Definitely. So for me, like I said, I am a litigator who hates conflict. So I was kind of, I made maybe the wrong career choice, but I absolutely loved and love the legal aspect of it all. So finding that case that's going to help your client, writing that perfect, well, close to perfect factum, getting up in court and arguing all those things I just really love, and I think I'm good at it. So when I was practicing as a freelance lawyer, it just, when you get to do something you love every day, but also have the control over when you're working and how you're working and who you're working with, it's like the best outcome that you can have. I think there's some people who may work very, very long hours but still love their job because they love what they're doing. So even as a freelance lawyer, there were some nights when I was helping with a trial, like behind the scenes, I'd be up until like 1 a.m. whatever, doing this. But these would come in like kind of spurts, not constantly up to 1 a.m. Right? And because I loved what I was doing, it was great. Like, so I think with law, there will be times, especially depending on which practice area you're in, you may have to work weekends. But if you have the flexibility and control to take some time off to recover from that, I think that's kind of the key there. So to answer your question, yeah, now I think I… when you're your own boss and have your own company or practice, you can say yes to a few things you couldn't as an associate.
Erin: [00:13:40] So for example, I don't have work email on my phone. So if I'm looking at work email, I have to be in front of my computer at my desk. For the longest time, I had it on there, but it'd be like, I would be checking whether before bed and an email would pop up with someone, even in the like the freelance context. I need a freelancer first thing tomorrow morning, and then I would just stress all night going, oh no, because I wasn't going to find a freelancer at midnight for them, so it just needed to wait till tomorrow morning anyways. So for me, setting that kind of restriction has really helped with my mental health. Just keeping work and life a little more separate. I also, when I was freelancing, I told myself I'm not going to answer the phone after a certain time as well. I wasn't going to answer emails or phone. And it's funny when you set those kind of, I would say boundaries, your clients, or at least because my clients were other lawyers, totally respected it. I said, I don't answer phone calls after 6 p.m. and one time I accidentally answered it because I didn't know what time it was. It was like seven, and my lawyer client was like, oh, I'm so sorry. I was just going to leave you a message. Why are you answering? And I'm like, it's okay, it's okay. Like, so when you enforce that and respect, those other people will too.
Tim: [00:14:58] Right. And it's, it seems to be that the system itself now, I mean, everybody expects everything yesterday. And I think those boundaries are extremely important. The way I always explain it, I don't know if this resonates with you is, I often say, listen, like you don't want me burning the candle at both ends 24 hours a day, seven days a week. Because if I don't get that rest and I don't do the things that I need to do, I'm coming in, you know, not 100%. And I'd much rather take that time and to block that off than not do that and not do a good job for somebody. Right? And I think that that's hopefully that's something that… do you think that we're making some changes? Have you seen any changes in the legal profession where those things are getting more, I guess less prevalent, that we're letting those things invade our personal space?
Erin: [00:15:58] I think so. I think, well, it's an individual or firm by firm kind of culture, I want to say. It's all about managing client expectations and setting those upfront. Sounds like you have that conversation with your clients upfront. Yeah. So you're not disappointing them down the line. A lot of law firms don't and then they expect a certain level of accessibility to their lawyers. And then there's no coming back from that. Like if you're available 24/7 to your client, it's really hard to crawl, like claw that back. But if you start the retainer agreement from the very beginning with those expectations. So definitely I see people who have started their own firms and smaller firms who respect those boundaries of their associates and partners definitely are managing their client expectations a lot better. And I think the clients are understanding. But some you know, it's expected some firms you're expected to be available 24/7. So I think in some places, yes, we've seen definitely an increase in that. I think it comes down to competition, especially at the larger firms. If one firm's available 24/7, then the other firms are like, we have to be available 24/7 to our clients. It's just that kind of attitude, that business competition there.
Tim: [00:17:17] Yeah, it must be hard to retain talent in that case, right? Because I think, I just see that people don't seem to be putting up with that anymore. They just don't.
Erin: [00:17:28] Yeah. I think it's a generational thing too, where people are more, they respect their own boundaries and their own downtime and their need. Which makes sense. We all like no one. Like you said, no one wants a burnt out lawyer. They're not going to do well. And really, it's a business case too, because if you're a big firm and your associates are all going out on leave for burnout and mental health issues, that's going to cost you money, too. So….
Tim: [00:17:54] Yeah, absolutely. What kind of things do you see in the profession itself that have led to kind of burnout that you experienced? And maybe you can reflect on some of your experiences, without kind of naming names sort of thing, but what are some of the things that were the hardest on you?
Erin: [00:18:11] Yeah, I know, so for me personally, it wasn't necessarily the long hours. It was the conflict between… the conflict in litigation. And I think lawyers have a tough job depending on which practice. Well, even all, most practice areas, people are coming to you at their worst time in their life. I think if, maybe if you're a real estate lawyer, people are excited because they're buying their first house, or maybe wills and estates because they're maybe getting married and drafting a will for the first time. But I, especially in litigation, people are coming to you at their worst and you are dealing with sad, angry, upset people who have had their whole lives probably turned upside down. And I don't… and I think law schools are getting better at this. But just teaching, like the trauma-informed lawyering and all that, all that kind of just keeping in mind that… I had a bad time of taking on my clients’ feelings and taking on their problems as if they're my own. And I remember, like, bathing my children at night, and I just could not get a certain file out of my head, and I could just feel how upset the client was. And there was no separation between work and home for me. I couldn't enjoy those precious moments with my children because I was still so emotionally caught up in my files, and I just was not good at separating the two. And maybe if I had some counseling or therapy or courses on how to do that. But I think a lot of lawyers struggle with that because we, most of us go into this profession wanting to help people and make the world a better place, at least somehow, right? And when you're faced with this all day long with people in crisis, it can affect you personally too, and lead to burnout and depression and anxiety and all the stuff that comes along with it.
Tim: [00:20:06] Yeah, I think what's really interesting about it, and I have not… don't have a psychological, psychology degree and, and whatnot, is it's, it's creeping sometimes like you don't even. I think the example was you and I were supposed to do this recording last week, and that didn't work out. And you don't even feel it till it kind of gets like knocking on your door and you're like, oh, wait a second. Like, I'm feeling that burnout. And it could be from a file you did five, you know, five files before, you know, weeks and weeks ago. And all of a sudden you realize, like, you, you know… and we're human. There's things that the trauma part that hits you that you don't even realize. And for you, it was the wills and estates work. For me, it's some of the family law work. Most of it, you know, doesn't bother me, but there's, every once in a while, there's certainly something that kind of creeps in where your, similar situation, where you're trying to enjoy a family moment and you're just not there.
Erin: [00:21:09] Yeah, yeah, yeah. It was definitely, for me, like corporate commercial litigation. There was disputes and there was, you know, angry emails and stuff. But going to estate litigation and you got to understand like it's most often brothers and sisters fighting over their dead parents’ money. And oftentimes it has nothing to do at all with the money or the house or whatever. It's because mommy loved you more than me or, you know, and I was not equipped to be on the phone all day with crying clients and people with deep emotional scars. And then when, when you take the person who had caused those deep emotional scars away because they've died, there's no like kind of closure for them. And so just all came out and I would take all of that on. I was not good at separating the two.
Tim: [00:21:59] Because it's hard to come to a result in that kind of litigation that you'd ever consider a win. Right? Like it's probably very similar to family law. You get through it. And sometimes I kind of, I get done a trial and I go, I think we did really well on this, but I have no idea. If somebody said, who won, I don't know. Yeah. Nobody, I guess.
Erin: [00:22:23] Exactly. But there's great estate litigators out there who have somehow figured it out and know how to do it. Just I was not, I was not the right fit.
Tim: [00:22:33] How many people do you have working for you now as freelance lawyers and assistants?
Erin: [00:22:40] Yeah. So we have about 80 freelance lawyers across Canada and about 20 law clerks/paralegals. They all don't work full-time. We have a very flexible, we send out projects and if they're busy doing something else, then they don't have to take on the work. But on the flip side, we can't guarantee them the number of hours that they want, which is great. Like it's a flexible way to do things. But from a business standpoint, sometimes it's a little hard when a law firm reaches out and they want X type of lawyer and we're like, oh, they're busy, or they're on vacation, but it's constantly trying to balance the supply and demand of this type of platform.
Tim: [00:23:17] And do you get good feedback from those people? Like what kind of things do you hear from, from them as far as how this style of lawyering has helped their practices?
Erin: [00:23:30] From the freelancers or from the law firms?
Tim: [00:23:32] Yeah, from the freelancers.
Erin: [00:23:33] Freelancers? Oh yes, for sure. There's some... They get so excited when they discover that something like this exists. We've helped people, for example, one woman, her spouse, had to leave the country and, for whatever, his job. And she's like, I don't want to have to give up practicing, and I don't want to be requalified here and wherever they moved to. And so she was able to freelance where she was and pick up some work and not give up her, you know, her whole degree. And then there's others who, you know, they have small children at home and they might want to step back from full-time practice, but it's hard to find, like a part-time job in law. There's really no part-time, there's few and far between. So this way they can pick up as much work or as little work as they want, while they're kind of balancing being at home. Or there's others who have, sick parents that they're dealing with a lot, and so they would rather just work fewer hours. Or even, we had, when we first started out, we had a couple of people who were doing like a tech startup, and so they didn't want to work full-time law jobs, but they didn't, in case the tech startup didn't go anywhere, they didn't want to give up all their legal skills. So, they were freelancing with us as well. So it's a real variety of people who find the flexibility of just being able to be in control of how much or how little work they take on. That's a bonus for them.
Tim: [00:25:01] Yeah. And so from a business side, how do you see the freelance lawyering market as compared to the legal market? You know, as far as demand goes, what kind of demand are you seeing?
Erin: [00:25:18] Yeah. So it fluctuates, I think how kind of things fluctuate in the real world, too. So, some months we'll have nothing but requests for litigation lawyers and we're like, oh, we don't have enough litigators. And then the next few months, it's all corporate work. And then things will slow down in some months altogether. And then other months it's going to be crazy busy. In the ten years we've been in business, I've been trying to find some kind of pattern. I thought maybe, will things slow down in the summer? But no. We had our busiest summer ever. And then things slowed down in December. And sometimes they do, but sometimes they pick up in December because everyone's like, I need to finish this up before year end. So I don't really have, it just really fluctuates. And it depends. Is my final answer on that one. I may plop in some of these statistics into ChatGPT, and maybe it can pick out the trends I seem to be missing.
Tim: [00:26:10] Right? So I guess, for… what do you see as for the future of freelance lawyering, and have you seen other similar businesses pop up kind of since you started this?
Erin: [00:26:25] Yeah. So there are, there's lots of freelance lawyer companies in the US and the UK and Australia. They've all kind of come and gone and some have stuck around, since like the early 1980s. I actually did a deep dive into this. I wrote a book this year called The Modern Freelance Lawyer: A Guide to the Business Ethics and Evolution of Freelance Legal Work. So one whole chapter is about the history of freelancing, like the early 70s up till now, and how things have changed. And really in the beginning it was mostly document review and kind of what you would call low-level work. A book was actually even published in 2011 called…. what's it called? Temporary Lawyers in the Deprofessionalization of Law or something. And it was a real critique of freelance lawyers saying that it was, we were bringing down the professional identity of lawyers, because of the work that we were doing was like low-level. I disagreed with most of what this book talked about, because I think it was focusing mostly on work that they call temporary lawyers or freelance lawyers were doing in the 80s. But now it's evolved to, because of technology and the safety of sharing documents and all that kind of stuff, we really can do anything a traditional lawyer can do. Like we can securely have access to the law firm's file to work on. We can work from home. So there's a lot of things that have evolved since freelance lawyering started. For the future, I think just like lawyers aren't going anywhere, I don't think freelance lawyers are going anywhere. But lawyers who don't use AI may be going away, and freelance lawyers who don't responsibly and ethically use AI. I should say that for lawyers as well. I think we need to stay up to date on this as well. But I don't think as long as there's lawyers around, I think there will always be freelance lawyers too.
Tim: [00:28:30] Yeah. No fair, I will out myself. I haven't read the book yet. I've got a list and it's on my list and I need to, I need to check it out because I think that's… it's, honestly as a small firm practitioner, it opened my eyes. I didn't even know that there was such an option available for times when you need it. And it's just been an incredible resource, you know, there you go. My shameless, my shameless plug.
Erin: [00:29:00] I will take all plugs.
Tim: [00:29:02] In closing on this, I always ask everybody the same question. Is that if there was one thing in the legal profession that you would change with reflection on mental health, what would it be?
Erin: [00:29:15] Oh, that's a good question. I think just recognizing we're not all one type of person. So if something works for one person and practicing a certain way, that may not work for someone else. And I think sometimes people think, oh, well, that person's weak because they couldn't handle this type of practice or that person's… yeah, mentally weak because they could. But no, but they're thriving in other ways and there's ways to think outside of the box when it comes to practicing law. And I think defining success is also helpful as well. Stop comparing yourself to other quote/unquote “successful lawyers”. If you are happy doing the work you're doing, you feel challenged and you're getting paid for the work you're doing in a meaningful way, that is successful to me.
Tim: [00:30:11] Right. Well, very good. And did you have anything else to add from that? I think that's a good way to finish up today.
Erin: [00:30:18] No, other than just saying thank you so much for having me on here. I think it's a very important topic and an important podcast for sure.
Tim: [00:30:25] Yeah. Thanks so much for being a part. I really appreciate it.
Erin: [00:30:28] Thank you.