Vivene Salmon: Hello, welcome to Conversations with the President. I’m your host Vivene Salmon. Recently a tweet from a participant at a CBA even sparked a small but intense Twitter storm and exposed a generational divide in the approach to practicing law. The tweet quoted a judge who said that the way to get noticed was to, “Arrive early, stay late and work hard”.

It seemed like wise advice from a senior lawyer to a more junior colleague but to a younger generation, it sounded like bad advice emblematic of an out of date law firm culture that they wanted no part of. The need to rack up face time and billable hours is often blamed for driving people, particularly women, out of firms and into solo practice, or to inhouse or government positions, but sometimes this approach drives lawyers out of the practice of law altogether.

Today I’m talking with two young lawyers who are blazing their own paths outside of the big law. These two lawyers have founded their own firms and forged a new way to provide legal services.

Erin Cowling started out on the traditional career path. After being called to the Bar in 2005, she worked as a corporate litigator at McMillan in Toronto, the same firm where she articled. Six years later she started her own firm, Cowling Legal, and in 2015 she founded Flex Legal, a network of experienced freelance litigators providing outsourced legal services.

Kim Gale is an estate litigation lawyer. She wanted to be a barrister from an early age but took a roundabout route to her JD. Like me, she started out working in communications and media, then she worked in shipping and logistics, and as an assistant to an estate litigator before going back to school for her law degree. After that, she hit the ground running. She was called to the Bar in 2018 and in 2019 she opened Gale Law. She’s also the author of the popular blog, Law for Millennials, and founder of a network of internationally trained lawyers.

Welcome to the podcast, Erin, and Kim.

Erin Cowling: Thanks, Vivene, for having us.

Kim Gale: I’m really excited to be here.

Vivene Salmon: Erin, you stayed in big law for six years before heading out on your own. What was the impetus for starting Cowling Legal?

Erin Cowling: It sort of came out of a necessity rather than me waking up one morning thinking I’m going to start my own business. Upon return from my second maternity leave, I found I was looking for a new job and I sort of panicked because I was a seventh year associated without a book of business. So I accepted the first job that came my way and that was in an estate litigation boutique and previously I had worked as a corporate litigator and I felt like a bit of a fish out of water.

And it was a very emotional practice with a lot of brothers and sisters fighting over their dead parents’ money and it just didn’t sit with me right, with my personality to practice that area of law and I found it very difficult and I took home the emotion every day and, at the same time, I found I was pregnant with my third child and I didn’t want to be in that job anymore so I quit without another job lined up.

But I didn’t want to be just at home with my children, I missed the law and I wanted to be a lawyer so I started picking up projects from other lawyers that I knew who needed help with either a factum or a statement of claim, so when I was at home I was drafting blog posts, any kind of little bits that came in.

And this was really going to be a stop-gap measure until I went back to work for either a large firm or a small firm and then I realized I really enjoyed doing my own thing and being my own boss, so I said I’m going to give myself a year and see if I can make a practice out of being a freelance lawyer.

So I put up a website, printed off some business cards and I got really busy helping other lawyers with their overflow legal work, and in 2015 I started Flex Legal Network to assist me with all that extra work that was coming in and so now I have – we have 25 freelance lawyers with our network doing overflow legal work.

Vivene Salmon: That’s amazing. So to me, it sounded like you took a very challenging situation and made it work for you strategically. Kim, you started your own law firm too, so what inspired you to do that so early in your legal career?

Kim Gale: Well it’s funny that Erin mentions the difficulty she had with estate litigation because that’s actually the area of law that I practice, exclusively estate litigation.

And I really – I think I started my firm because I had two other entities that I began; one was a fun blog called Law for Millennials, which I started while I was an associate at another firm, and it was just because I found that everyone including most of my friends who aren’t lawyers thought that law was really boring but they would ask me questions and I would explain to them in a way and they’d say, “that’s interesting, I never thought about that”.

So I started a blog that was basic, free, easy to understand legal information based on issues millennials faced and I had a lot of success in that. A lot of people seemed very responsive and they really liked my blog and I thought OK this is interesting; I have a bit of a following here.

Then I started a group which I was really more passionate about called NCA Network, which is a young professional group to help students that went to law school outside of Canada because I went to law school in the UK and when I returned to Canada I found it was extremely difficult to have a network, to find jobs, to tell people that I’m willing to work hard and give me a chance, and we have now almost 500 members and we’re going really strong and we appreciate all our partners and sponsors.

And between the success between those two I thought if I could get clients and start my own firm, that is what I would love to do because I am very entrepreneurial and I’d love to be my own boss and I also was running out of time between Law for Millennials and NCA Network to build the expected, you know, huge billing hours that a firm expects of you and I thought I really enjoy these things, I want time to dedicate to them.

Vivene Salmon: So speaking about the billable hour, you just mentioned that, how do you both feel about the billable hour? Maybe, Erin, we’ll start with you.

Erin Cowling: It’s funny, in my I think third or fourth year of practice at the large law firm all the women lawyers received a questionnaire about how to improve practice for women lawyers at the firm. And one of the things was do you have any suggestions and I said get rid of the billable hour, and it was kind of received with a bit of a laugh because they thought I was joking.

But really, having become a mother, I am the most efficient person out there and the billable hour is actually to my detriment because I can get a really good statement of claim out the door quicker than someone who may not be as efficient as me but I get penalized at the end of the day because I didn’t bill the how many hours that other people might.

But the funny thing is when I started freelancing in my own firm and company I thought you know what, I’m going to offer alternative fee, I’m going to offer flat rates, I’m going to offer everything but the billable hour, 99.9% of our clients want the billable hour because our clients are all other lawyers and that’s all they know. So I’ve only had one – one lawyer reach out and ask for a flat fee because they had offered their client a flat fee.

But then, with that being said, we do litigation which I think is a lot harder to get away from the billable hour than like a real estate transaction or a corporate document might be a lot easier to deal with in a non-billable hour way.

Vivene Salmon: So Kim, let’s hear how you feel about the billable hour?

Kim Gale: I mean it’s the easiest way to determine … billable hour comes from two veins; one is the employee, and one is the employer. From an employer perspective, and Erin and I both have people that we employ, it’s the easiest way to dictate what someone’s spending their time in and how much – from a business standpoint how much money they’re bringing in.

From an employee perspective, you know, it has to be attainable and I also recall sometimes I just wasn’t getting enough work and it’s hard to meet your billable target if the people around you aren’t giving you the chance to actually work. So you’re kind of making work and doing non-billable work and I think – I mean I don’t think that anything is going to change from the billable hours.

I think we all bill per hour and that’s how we make money. I think that the problem arises when the politics come into play, when certain people aren’t given certain work, so they’re not given the opportunity to bill and kind of like the complications around just looking at someone’s just billable hours and not anything else.

Erin Cowling: I think until there’s a pushback from the client end of things, billable hour is not going away, and I haven’t seen that pushback yet. There’s still firms out there making money hand over fist with the billable hour model. Even though we’ve been told for how many hours now by, you know, the legal innovators out there that the billable hour is dead, it’s still alive and kicking, I think.

Kim Gale: The heartbeat is there.

Erin Cowling: Yeah.

Vivene Salmon: So let’s switch gears a little bit and talk a little bit more outside the billable hour but about the business of law. Erin, where did you learn how to run a private practice.

Erin Cowling: Through trial and error and through necessity. I started my business just by printing off some business cards, doing my own website and getting out there and hustling, and then just reading as much as possible. I didn’t have the money to go hire fancy business coaches and do anything extravagant with my marketing. I had to do it all on my own and it was really, yeah, just day to day stuff trying to figure out how to collect from the clients, how to market myself, how to get my brand out there. It was really a lot of work and trial and error.

Vivene Salmon: So, Kim, how long did it take you to feel secure that you really knew what you were doing?

Kim Gale: I mean does anyone ever really know what they’re doing [laughs]. To be honest, I think for me the reality was I felt very comfortable in my area of estate litigation and I chose to specialize for a reason – because I know this area, I understand the sibling dispute, I understand the overarching process, it’s a very niche area.

So I can take a file and run with it from start to finish without kind of second-guessing myself but there is definitely aspects, the business aspect is a whole other side to it. You’re a lawyer and a business owner and an employer and you are dealing with so many other aspects that take away from the lawyering. And we’re really just in a client-facing industry, we’re no different than any other – we’re no different than working at a store and facing clients every day.

I mean our job is to service our clients in the end and have happy clients so that requires a certain personality and I always felt like I had the personality and the hustle. I also built my own website and networked and got out there. When I moved here in 2016 I didn’t know anybody, I really tried to utilize social media the same way as Erin did and really lean on the support of the community.

Vivene Salmon: So you’re both in Toronto, a city with a pretty large population. What would you say are the important considerations for someone looking to start a solo practice outside a major city, and so what are your biggest challenges, to provide that advice to people?

Erin Cowling: I think if you were looking to start a solo practice outside of Toronto you have to look at the needs of the community. There will always be a need for real estate and wills and there’ll be property disputes, there’ll be some type of civil litigation. So if you look at the community and what those – you might not need someone who’s got a niche area of like international relation law in small-town Ontario.

If you have an interest in those areas of law, I think there’s lots of opportunities in lots of different areas outside of Toronto. I think it’s the same thing, you have to build a practice and build your brand and get out in the community. Think about where your clients are and market yourself and network.

Vivene Salmon: Why is there a need for firms like Flex Legal?

Erin Cowling: I started Flex because before when I was working at a large firm, like a lot of lawyers, I felt like law was either an all or nothing game, we either had to work 100 hours a week or quit law altogether. And as a freelance lawyer and with Flex Legal we offer a flexible practice of law; we can take on as many projects as you want, or as little work as you want.

Our freelance lawyers do a variety of things, some work full-time, some have kids with disabilities so they’re at SickKids a couple of times a week, some – we’ve got a couple of guys who are doing a tech start-up but they don’t want to give up law completely, so they’re taking on some projects here and there.

And then on the flip side for our clients, personal practitioners or small firms who are a majority of our clients, sometimes they just get so overwhelmed with work but they don’t have the overhead or the resources to hire a full-time associate or bring on another partner, then they can just reach out to us to fill in for a trial or help with some drafting or even if they want to take a vacation, help with their work-life balance as well.

Vivene Salmon: So Kim, you don’t have maybe the stress that comes with working for a big firm but you do have a lot of stress, I think, and pressure just the same generating your own clients, managing a small business and ensuring you get number one paid by your clients. So how do you do it and still have a life?

Kim Gale: Do I have a life? I mean it’s all – a lot of it is you have to protect yourself as a lawyer, you have to be very forward with your clients. When I do my initial, I do a 20-minute free consultation, I set out the terms of the phone call before it even starts. I get their full name, their contact information, I tell them that this is a 20-minute phone call, they won’t be charged for it, only time after will be charged.

I tell them my – I listen to, you know, what it is that they have to say, sometimes it’s not an area I practice, sometimes it is and if it sounds like it’s a good fit for something that I would do and it fits the parameters, I tell them exactly what my fees are. I tell them what the retainer is, I make sure to, you know, receive my retainer in a certified cheque or if it is a regular cheque, I wait the 10 business days for it to clear.

I send my invoices every month, I follow up. I’m very diligent in that aspect because, you know, I don’t think anyone should work for free and as a lawyer, we’re taking on a lot of liability and, you know, if we’re not getting paid then I could just stay home and sleep in that morning. So I think the business aspect should not be overlooked.

And I get a lot of lawyers who ask me about running a business and being entrepreneurial, but they don’t want to discuss money or there are certain aspects of their personality that it makes them feel uncomfortable, then maybe I would recommend that they would go in business with somebody else who has the more business sense or they may want to rethink it because you’re doing every aspect of your business.

Vivene Salmon: What are some of the day to day obstacles of running your own firm?

Kim Gale: Well I would say every day is different. That’s why I love being a lawyer and most lawyers like this job because no day is the same; one day you can be in court, another day you can just be drafting, another day you’re on the phones, something blows up.

 But general obstacles, I mean last week or two weeks ago my system just crashed and then I had to hire an IT person, get that person in and redo my entire system. So, you know, an assistant is sick one day and you really relied on them to come in. Probably similar issues to what anybody faces in any business …

Erin Cowling: The buck stops with you, I find. Like you can’t throw the crap up the – because there’s no one above you –

Kim Gale: – Yeah, there’s no –

Erin Cowling: – there’s no IT person. –

Kim Gale: – It stops with you, yeah.

Erin Cowling: So anything that goes wrong it’s your problem, that’s my major kind of …

Kim Gale: I agree, that would be my – that’s always a stumbling block. I’m the one who has to be the HR, I’m the IT, I am the one on the phone. We all have assistants and people to help us but, in the end, they come to me for the answers and I do my best to address any problems that come up.

Vivene Salmon: So Kim, as you know this podcast goes across the country, is there anything you’d like to tell other lawyers that are listening that we may not have touched on, what is one piece of advice that you have?

Kim Gale: So my advice would be to know yourself and assess the situation at hand. If you’re extremely unhappy where you’re working or circumstances in your life lead you to the point where you don’t have a work-life balance and, you know, you’re miserable, then don’t – I know some people feel as though it’s big firm or no firm, there are so many options out there where you can still practice law and have a fulfilling career.

So I would definitely say to kind of deep within your soul, as cheesy as that sounds, figure out what kind of works for you and if it’s not law that’s fine, there’s so many other positions and jobs available for someone with a law degree and with legal experience and legal background. But if it is law and it’s something that you enjoy, you know, is the practice area, is it working in a big firm, would a smaller firm suit you better. Some people go from smaller firm to big firm because they like the structure.

I mean big firm is good for certain personalities and small firm is better for others and some people have the entrepreneurship and the ability to go out on their own and then hustle.

Vivene Salmon: And for you, Erin, is there anything that you’d like to add or one piece of advice you’d like to give other senior lawyers and younger lawyers across the country?

Erin Cowling: I’m a bit biased, but I really love being my own boss and having my own business and I didn’t think I was an entrepreneurial person when I was at a large law firm, I liked having the paycheque every two weeks and the security but then, you know, live happens and you realize you can do this on your own but you do need to have a little bit of a business sense.

I know some lawyers who have started their own practice and they hated the business side. They hated going out and getting clients, they hated doing the accounting or looking … you know, they just wanted to be lawyers, they just wanted to put their head down and do the law, being a sole practitioner might not be the perfect job for you.

But if you do … I love, I have a 50/50 – like 50% of my practice is running Flex and being an entrepreneur and 50% is actually doing the law and I love that balance because I get to flex both sides of my brain. So I think along the lines of what Kim was saying, you really have to know yourself and whether you think you can be a businessperson as well as a lawyer.

Vivene Salmon: So Erin, maybe we’ll end with you. What can the Canadian Bar Association do to help people who want to hang out their own shingle like you?

Erin Cowling: I think mentorship helps a lot and I know there are mentors available to help with questions, available for people who want to start their own business as a lawyer. I get so excited when I have coffees with young women who are at large firms and like, “I really want to start my own practice but I am nervous” and I’m like, “Let me help you because you will not regret being your own boss and taking back the power of what you’re doing as a lawyer”.

Instead of lining the pockets of other people, you can take this and decide how you want to practice law and how you want to make a difference in the legal profession. So mentorship would be very helpful and, you know, other resources like articles that I know the CBA provides and just having someone to reach out to with questions.

Vivene Salmon: Young lawyers like Erin Cowling and Kim Gale are increasingly rejecting the traditional law firm and forging their own path with the risk and rewards that brings.

We want to hear your stories about the changes you’ve seen in the legal profession or think the profession needs to make, where do you see generational conflict and how do you suggest we overcome it. Let us know on Twitter at @CBA_News, on Facebook and on Instagram at @canadianbarassociation.

You can hear this podcast and others on our CBA channel The Every Lawyer, on Spotify, Apple Podcast and Stitcher. Wherever you listen to podcasts, subscribe to receive notification for new episodes, and to hear us in French, listen to our Juriste branché podcasts.