Episode 2. Living Authentically at Work With Tom Stephenson

Tom Stephenson: For those that are about to get on the journey, know that all of us experience this at some point in our careers. It's not just unique to-

(Tom burps. Kate Bridal laughs.)

Josey Hoff: Perfect.

Tom: We're gonna do that again. (Laughter.) Should we pivot to a final thought?

(Loud laughter. Musical introduction starts.)

Introduction

Kate: I'm Kate Bridal, the former attorney who never cared that much for the law. 

Josey: And I'm Josey Hoff, a former paralegal who loves it. 

Kate: And this is our podcast where we talk about all the stuff that leads to burnout in the legal industry, try to offer some solutions, and maybe occasionally live up to our title. Welcome to the Legal Burnouts.

Episode 2

Kate: Honey, honey? 

Josey: Yes, darling?

Kate: You wanna do a podcast?

Josey: Today? Yes, I do. Yes, I do.

Kate: Oh, fantastic. I'm so glad to hear it. 

Josey: Because we have a great guest today. 

Kate: We do. And one of the only people who knows the story behind our little shtick at the beginning, our “honey honey” shtick, because he was there—

Tom: Oooo, dun dun dun!

Kate: --the infamous night that this podcast was born. 

Tom: The night the lights went out in San Francisco.

(Kate laughs.)

Josey: Yes. And Josey agreed to do something she never thought she would do. 

Kate: And now here we are. Yes. 

Josey: Mhmm. 

Kate: Today we are joined by Tom Stephenson, the Vice President of Community and Legal Operations at Legal.io. Prior to Legal.io, Tom served as Director of Legal Operations at Credit Karma and played a pivotal role as Teledoc Health’s first legal operations executives, so he's all about the ops.

Josey: Woo woo!

Kate: Yes! Additionally, Tom's extensive experience includes over a decade of service in various law firms in Chicago. I love Chicago. I'm very jealous. And beyond those corporate roles, Tom is also the cofounder and host of the nationally syndicated Dear Legal Ops podcast, which I love, which is now in its second season, which is crazy because I feel like I was just talking to you about it coming out, Tom.

But it's- it's fantastic. If you don't subscribe, if you haven't listened, please go do that right now. You can turn this off, take a break, go listen to a couple of episodes, come back to us. (Josey laughs.) The podcast is renowned for its fresh bold approach to addressing challenge topics impacting today's legal operations community through the innovative medium of anonymous letters, which I love.

Tom: Mhmm. 

Kate: And yeah. So he's got this blend of practical experience. He's got a passion for education and community building. Tom Stephenson, you driving force in the evolution of the legal ecosystem you, we're so happy to have you here. 

Tom: Ladies, I am super happy to be on the legal burnouts because this is where the real talk is, and these are the fun conversations I love having with the community and friends, and those that kind of blur the lines between the two. 

Kate: Yes. 

Josey: You know, blurred the lines is a very accurate way to- to describe all of us. So…

Tom: (Laughing) Yes.

Josey: I love- I love that for this group.

Kate: We started as professional associates, and now here we are. I would say we're definitely friends at this point. Thank you so much for being here, Tom. We're so excited to have you. You're gonna be the first guest episode.

Tom: Oh, the first. I like this. 

Josey: We saved it purely for you, Tom. 

Tom: Oh, well.

Josey: Regardless of the topic, we had to have you first. 

Tom: I would like to say thank you to all those that come after me because I- you only can go up from here. So let's- let's just rip this band aid right off.

(Laughter.)

Kate: Please. Please. No. You're fantastic.

We'd love to hear, just like as a starter, a little bit of- of your story, Tom, and- and any points where you experienced burn out yourself in the legal industry and kind of, you know, where you were, where you are, what… Tell us all about the story of Tom. 

Tom: Oh, let me go ahead and-

Josey: Yeah. Let's get real here.

Kate: You were born on a cold night… 

Tom: Yeah. I was born at 4:44 PM, and as my father likes to say, he used to walk uphill both ways in the snow without boots, all da da da da.

Kate: Wait, were you actually born at 4:44 PM? Because I was born at like four thirty-something PM. 

Tom: I was, and four is my favorite number. So…

Josey: You guys. I was born at 4:32. 

Tom: Well, this is—

Josey: What on earth? 

Tom: Welcome to the four- Actually, it is 4:27 in California right now. So.

Kate: It is, and for us as well.

Tom: Welcome to- Yes. Welcome to the four PM legal burnout episode. 

I think I definitely started burnout before I started working. And I've always just been this creative individual going a hundred miles an hour trying to paint with all the colors, you know. 

Kate: Mmhmm.

Tom: And in college, I really didn't know what I wanted to do and kinda just fumbled my way through and ended up at a law firm starting off as a receptionist.

It really, I think, has shaped who I am and my love for the industry, but it hasn't been without burnout along the way. I mean, I worked in Amlaw firms in Chicago, and then most recently for two Fortune 500 in-house legal teams. And now I'm, you know, vice president of community and legal operations for a startup. 

So burnout can be in any industry. Right? Big, small, law firm, corporate in house. And for me, it's really just about how do I figure out how to overcome it, how to recognize it, and really figure out if I can't change it, how do I actually cope with it?

Kate: Absolutely. What were you studying in college? 

Tom: Oh, gosh. Which- which time I changed my major?

So – 

Kate: Oh!

Tom: -- the official record is psychology, and then after that, it- Oh, and then I did the tour of education. And so we then went and got the associate's degree in paralegal studies, and then we got the masters in legal studies. And so – 

Kate: Oo!

Tom: -- I've got the I've got the ABC's of education up in here. 

Josey: I love it. I love it.

Kate: I'm technically supposed to have an associate's degree, but my drama school never gave it to me. I never- never received the paperwork.

Tom: We could do a whole episode on why I went that route because education was needed as a pre-qualification in the legal industry at some point. Right? And so it was like, oh, well, you don't have legal certificate? Well okay, so I will just go get associates degree in paralegal studies because I already have a bachelor's—

Josey: Mmhmm. 

Kate: Mmhmm.

Tom: --and I'll just take the classes. And so, yeah. That- that could be a whole episode. But 

Josey: Yeah.

Tom: Yeah. I mean, where did you guys think that you first were hit in the face with burnout. Right? Was- At what point in your legal career was it? Because for me, it was working at a national burn and churn law firm and knowing that I probably didn't have any place sitting in that seat, but I was sure as hell gonna do whatever I needed to do to make sure that I continue to climb up the career path. And that always said yes to, like, sixteen hours? Cool. Let's do that. Right? 

Kate: Yeah. Josey, you wanna go fir-? I feel like your story is similar- similar to Tom's. 

Josey: Sure.

Kate: I'm the- I'm the little weirdo off in nonprofit land over here.

Josey: (Laughing) I'll piggyback off of that. That's fine. So kind of similarly, I had a similar experience in that I didn't know what I wanted to do initially when I started college. I then took a year off. I worked for a publishing company, which I don't know if I mentioned before to you, Kate--

Kate: I didn’t know that! 

Josey: -- but I did.

Kate: No!

Josey: Yeah. And then I worked- I worked for- I saved this for Tom. 

Tom: The Legal Burnouts: Connecting podcast hosts since 2023. 

(Kate and Josey laugh.)

Josey: Right? And I- I did work for a publishing company for a year when I just decided to fuck around because I didn't know what I wanted to study. And I loved it. Ended up going back, and that's kind of when I stumbled into legal. I always loved it, but I hadn't really committed to studying it. I was gonna go the policy and the politics route before.

I was legal secretary at first, so I was the receptionist, the legal secretary at a little firm when I was in college, and then went to a very large law firm in DC by chance. And I say this all the time because I was not… In -in my view, and if I were hiring someone, I was not qualified at that point. I was this, you know, young recent graduate. 

I was there for three years. It was towards the end of the time that we were working on a lot of abortion band cases because we did a lot of pro bono work. And watching those go through, all the- the sixteen hour days that you put into those, and then knowing at any point they could be overturned, and they were often and, you know, even more so now. I think that's when I started to kind of experience burnout because it was the long days and then knowing that the work may not even stand or may not even go very far. And that was kinda – 

Kate: The futility.

Josey: -- the initial. Yeah. And I mean, there's several elements of burnout. I think through all of our stories, I mean, you – 

Kate: Yeah.

-- consistently kinda can experience burnout, but that was the first time. 

Tom: So what about you, Kare, like, when did you first experience it? 

Kate: You know, it's funny. Like, I I would have thought that I would have burned out basically in law school, and I definitely wasn't that into law school… I didn't wanna be an attorney. Right? Like, I went to join the FBI, and then that just went out the window for reasons that you can listen to in our first episode if you haven't listened to it yet. 

(Josey and Kate laugh.)

But so I was just like, okay, shit, now, I have to be an attorney. And sort of found some things that I liked to do, really landed in kind of the criminal defense/prisoner advocacy kind of camp that I really liked. I had no interest in going to a firm or doing anything corporate. And then I got out of school and bar exam study was the first time I started experiencing severe physical anxiety. But, you know, that's- You're like, “Well, I'm gonna get through it and then it'll be done.” And then it was.

And then it was when I started practicing finally as an attorney, arguing with landlords all day and- and starting to feel like I was beating my head against the wall. I was also terrible at boundaries at first and by the time I put them in place, it was kind of too little too late. I had already burned myself out, and so that's another thing that I love to kind of talk about on here is- is folks who have good boundary practices. And then I- I burned out and I just I- I left. I peaced out of practice of law completely.

I-I found a job in legal tech and that… I only practiced for two years and- and that was enough. I burned out after six months, I think. And was basically looking for everything else from that point forward. 

Tom: For me and I think for a lot of us, it's how do you maintain that healthy work-life balance? Right? It's – 

Kate: Yeah. 

Tom: -- it's not beneficial. It's actually essential. Right? It's like not a plus that you get, you know. And so challenging this culture of overwork and being able to navigate that as you climb up the career ladder at whatever stage you're in, I- I it's- it's very hard to do because you either say yes to everything, you know, you're the --

Kate: Mhmm. 

Tom: -- House of Yaaass and you- Everything is yes, right? But then you're not saying yes to yourself. And so, do you recognize what your worth is? 

Josey: Mmhmm.

Tom: And that's a lesson, I think, some of us- most of us learned by falling flat on our face. Right? 

Kate: Yeah. 

Josey: Yeah. Your point about it not being a bonus, but essential: To have that work-life balance, even when you look at a- a job posting, oftentimes, you know, the balance aspect of it is listed as perk. When I was burned out, I was searching for that as a perk. And it's like, it doesn't start with searching for a job that can offer you that, the balance really starts with you having those boundaries or you choosing it and saying it's essential for me to have that work life balance. 

Kate: Yeah. And some people work is their life, and that's okay, and they like that. And- and I thought I was that person. Until I realized that I was not. And it was extra hard for me to recognize too because my husband was also deployed. So he was gone, and that's another source of burnout. And so I was like, oh, well, that's probably it too, right? I don't have my support system here, it's COVID, I'm not seeing anyone, all of this- Even though I'm an introvert and I loved not seeing anyone.

And then he got back and then I was still burned out and I was like, oh, maybe it is the work. (Kate and Josey laugh.) Not that I'm being gone helped, but yeah, I had to eventually realize, yeah, no, I just can't do this…job.

Tom: Yeah. I think it's interesting, this recognizing your self-worth, if you will, and how that kind of is tied to your identity in the work place. Right? And – 

Kate: Yeah. 

Tom: -- today, sitting in this seat right here in my role as Vice President of Community and Legal Operations at Legal.io, I am obsessed with what I do. Right? I'm obsessed with this community. I'm obsessed with the different layers of the onion here, right, whether it's from the how do we help people in their career level it up, to how do you be authentic as a friend, to how do you form friends that are in the community but keep those boundaries? Like, there's a lot of these things that you kind of have to figure out as you go along the journey. 

And like, true talk, it was never really easy for me being a male paralegal as part of the LGBT community, growing up in Ohio and going to college, and then as soon as I was done saying, like, I have put in my time. Right? Like, I have put in my time in this state that I am not – 

Josey: Middle America.

Tom: -- identifying with, you know, in doing the check the box things. Let me go to Chicago and live my best life. Right? And that was fun until I got into law firms, and it was like, “No way you have to be the buttoned-up paralegal and you can't bring any color or any flair to the- to your job” for fear of corporate clients may wanna take you off their case, right?

And then- yeah. So, I just- I really think it's an interesting dynamic, but struggle that I myself have tons of years of, you know, this- What was trauma that I've now worked through over you know, over time, but really --

Kate: Mhmm. 

Tom: -- what's your identity in the workplace and how do you realize your self-worth? 

Kate: Like, “Don't bring your color to work,” like, was that told to you, Tom, in so many words, or was it more kind of a vibe?

Tom: Yes. I mean, it was told on a couple occasions I guess you could say maybe inappropriately. Right? But the culture of working for a, you know, large law firm in a big city- and I primarily focused on this weird intersection with I which I'm also in my paralegal life, I was obsessed with and I still am to this day of… I did corporate bankruptcy, so chapter eleven bankruptcies, but I did the litigation side of it.

Josey: What?!

Tom: So I would represent companies or corporations and adversary proceedings. So it was this intersection of corporate and litigation. So when I would go to trial, right, when I would go you know, I- You've seen Tom probably in the sparkly shoes, right, at the conferences. 

Kate: Mmhmm!

Josey: My favorite.

Tom: And that- that's fun to me because, you know, I'm an- I'm actually an- an introvert extrovert. So I thrive on those situations and that opportunity, and that was never there. And that- Although it's a very specific example, you see that throughout law firms in which you have to wear very shirt and tie every day and it needs to be, you know, not colorful at times. Right? Or if you're representing a client and- and that can then also transcend into how you may talk. Right? Or the-

Kate:  Mhmm. 

Tom: I've now gotten this y'all thing when I moved to Texas for Teledoc. I don't know where it came from, but it stood with me, but I know that when I was in a Chicago law firm, like, things would be said about people that had Southern drawls too. And so, it's just, it's such an issue.

Yeah. What- what are your guys' experiences?

Josey: I will say, I was very, very fortunate with the- the first law firm that I worked with outside of college. It was a great law firm. It was, you know, as far as Biglaw goes, very progressive.

But just because an organization or a firm, their principles can be one thing, doesn't mean every attorney is going to have those same principles, or every partner is going to operate the same. And so there were things throughout my career where… I always made sure that I wore long sleeves because I have tattoos on my arms, and I- they looked professional, as some would say. I did have those elements, whether it was implied, whether it was the environment that kinda made you feel you needed to stay in a certain lane, or it was comments and- and things that were made directly.

Kate: And I feel like anyone who's, like, part of a historically marginalized community gets very good at picking up on what the vibe is. You can start sensing like, “Oh, okay, this is the person I need to be in this scenario,” you know. And I think especially in a traditionally very kind of stuffy industry like legal. 

I got lucky because I was, again, in nonprofit and in public interest it’s a lot of female leadership, a lot of women, which is actually its own kind of problematic thing, it’s a lot of white women in nonprofit especially. Which I was just actually reading an article about stuff that I was guilty of, you know, going in and being like, “I want to save the world!” And you're like, that’s a condescending place to start from when you're going into nonprofit.

(Tom and Josey laugh.)

But I got really fortunate in that I wasn't in, you know, I wasn't in that kind of stuffier environment, nonprofit is a lot more… A lot more chill. And I worked, I think, exclusively for women, basically, my whole career in legal. 

Tom: And what's- what's interesting about being in that step is and- and Josey, I would love to hear if your experience was different. But for me, it was a point where you know, you… it happens. Right?

You- you're identifying it. Sometimes you are letting it get to you. And then when you finally have had enough, that's when you're like, “Okay, I'm gonna take control now, and this burnout or this whatever is eating me alive, I have to kind of push past.” Right?

That for me was also concurrent with me realizing that I had also hit the end of my career path in law firms because I wouldn't go to law school. 

Kate: Mm.

Tom: And while being, you know, head of a litigation department, you know, as a non-attorney in a senior paralegal role and then law firm administration, kind of going up that route, it was… It- it didn't feel enriching or rewarding. 

And so when I- I think when I said, “Hey, I'm at the end of my career as a legal professional in the law firm environment. And I'm also over this shit elsewhere, that's the law firm culture.” That's when I was like, okay, cool. We're gonna not lose sight of this worth and potential we built up, right? And honestly, I used it really for this motivation to push for change. Like, in the workplace and within the wider legal ecosystem.

Josey: Mhmm. 

Kate: Did you have like an aha moment? 

Josey: Yeah. 

Kate: Where- where you made that decision and you were like, I'm not taking it anymore, I'm gonna be me and I'm gonna, you know, make this difference?

Tom: Yeah, it actually was… I moved to a smaller law firm in size, and so was the last law firm that I was at. They were a innovative start-up mentality law firm that we're taking on big cases, and it was when I was one of the first paralegals, which then hired a group of paralegals and kind of built out that support staff to grow them. I still was the only one who would be tasked with filing a motion in California while I lived in Chicago, (Kate sighs.) so it was two in the morning because it was a twelve AM deadline, and my ex at the time was not happy that I was at two in the morning doing real work, right? I wasn't loving the work that I was doing. 

And I was like, on year ten, we're over it. We are O-V-E-R it. And that's when I was like, okay, what- what can I do next? And then that's when I started shifting into the “what is next?” Going through that phase in my life and figuring out, oh, actually love legal ops. It's what I've been doing for the last decade. And then I started just busting through the doors, Tom Stephenson-style here and being like, “Hi, can I learn more?”

And then that just metamorphised into this amazing job where I get to be a community representative, be a part of the community in actually legal operations for a startup, and so it's- it's this, it's, yeah, it's… For those listening, I guess I would say, is it sucks at times, right? And it sometimes doesn't feel good, but I think the piece of advice I would give is, you know, you have to understand when you can be able to go through that resilience and trusting your own instincts, and sometimes you create that role for yourself. And oftentimes, the first iteration isn't what you envisioned, but stay focused, Right? Stay- stay hungry and learn from the experience and don't let it get you down. 

Kate: Put on your sparkly shoes and kick the door down. 

Tom: Yes.

Josey: Tom Stephenson-style. I love that. To your question, it was-

Tom: Oh, wait. I asked a question? I totally forgot.

(Kate and Josey laugh.)

Josey: You asked me how I got out, like, what I did when I experienced that. And if it was explicit. It, like-

Tom: Ten minutes later. 

Kate: It's okay.

Josey: No. I love that because it give- The way that you dealt kinda with the burnout, like, once you hit that that aha moment and the fact that you were, like, alright, how else can I do, you know, something that I'm interested in and in- in a way that's more authentic to- to me and my interest and all of those things? I had a really hard time with that because I didn't know where to go from traditional law. And when I decided I didn't wanna go to law school, because that's the trajectory I'd been on, and every lawyer I worked with is, like, oh, you're working towards that step of going to law school…

I hit the point where I was like, well, I'm not gonna do that. So then my career in law firm is also over. I either stay like this or I move out. And I did not think of other like, corporate law was not something I'd ever even about are considered because when I thought of being a paralegal, being, you know, a legal professional that wasn't an attorney, it was in law firms. Legal ops wasn't even something I'd heard of in all honesty.

Kate: Me either. And I kept thinking, “Why did no one tell me about this in law school? Why did no one tell us?”

Josey: Right?

Kate: Because there are so many folks in law school- or not in law school, folks in other legal careers- who just don't get told about it and who are looking for that thing that's not quite the practice of law…But-

Josey: Yeah. 

Kate: It's, like, the kind of organizational stuff that people love to do, keeping people's shit together.

Tom: How we're here today is literally because a group of people were like, hey, we should standardize this, and we should follow this and grow it. 

Kate: Mhmm. 

Tom: And I guarantee you it was probably because of some burnout, right?

Josey: Probably.

Tom: -of the of the similar situation. And It's the most fascinating thing I think about the legal operations sector of the legal ecosystem, but you're also starting to see it with next generation attorneys, right? 

Kate: Yes. 

Tom: You'll see these attorneys that come in and they're working for these large, mammoth-size, you know, Apples or even- even some startup companies. Right? And they're the first legal hire internally and they're like, “Yeah, we should get, like, an ebilling system and a CLM immediately,” and you're like, “I'm sorry, go again, what?” (Kate laughs.) I love you so much, and it’s only Day 1. 

Kate: Excuse me? Yes. Will you give us a little rundown of the magic that is legal ops? 

Tom: Oh my gosh. Yes. 

Kate: The look on your face, you were so happy. Tom just looked like I told him he won the lottery.

(Josey laughs.)

Tom: Let me tell you, children, here. Legal operations is the solution for running your legal team or department like a business. And this has generally been corporate in-house. But at times, we are now seeing it spread throughout the law firm ecosystem. It may not be called legal operations, but you're starting to see these legal change management roles within law firms or these legal innovation roles, and it's really starting to…

It's running legal like a business, and so you are… Those who wanna go to law school, go to law school, they take an exam, they pass the exam, They're licensed to practice law, and so they should, first and foremost, be focused on that. Right? And too often, we've seen in the legal history, this, “Oh, we're legal. We don't have a budget.”

Right? Or, “We're legal, like, everything takes long because it's legal.” Right? And when CEOs and corporations started realizing that no legal is actually just another business group, like every other business group within a corporation -- 

Josey: Mhmm.

Tom: -- combined with the fact of economic hardships and things like that, this booming career called legal operations just took off. And it's always been there, but I think it's now starting to not just- It's even past, like, starting to, like, walk. It's running, and it's running fast. And what's great about it is you're finding these dynamic, passionate, educational, inspirational individuals who… It’s the land of misfit toys, right? (Kate laughs.) You bring something to it that is this business savvy, legal, knowledge expert, change management, tied in with being a legal tech nerd. Right? And- and that spawns this- this amazing profession that you have people entering, you have people that are mentoring, and everything in between.

Kate: Yeah. And it's all about efficiency. And, like, helping attorneys do their jobs more – 

Tom: Running legal like a business. 

Kate: -- easily and, like, not having to do all of that nitty gritty administrative crap that gets in the way of practicing law that I do think contributes to burnout. When you're practicing law and- It's not just getting to do your legal research, which is something I think a lot of folks in legal like to do, including me, I always liked that. Or getting to argue a case. A lot of the work is like tracking your time and figuring out where you have to file something and when and what size paper and all of that fun nitty gritty shit that you just-

Josey: Unless you have a legal assistant or paralegal to do it for you and then they have to do it. 

Kate: Right, which you stick on the paralegals.

But I have also heard about folks in the ops function burning out because it is so new, I think, and- and a lot gets thrown on you.

Tom: I- I will tell you that, you know, in my in-house legal roles that I've had before, it's often told like, “Hey, burnout is just a part of corporate America.” Right? Like, you swap not having billable hours for working a, quote, “in-house life” and I have experienced it myself.

I will say, I was much quicker to know that I was experiencing it, addressing it, and then being like, nope, time out. Like, this is not the path we should go down. It would have taken me a lot longer, I think, if it wasn't for the law firm burnout before. But it happens.

And I think it happens for a lot of us because we are trying to level up our own of careers. Right? We are in the midst of what is booming professional expansion, right? It's taking on more. I will say it was a lot of fun last couple of years when we had Daddy's credit card to spend all day long. Right? (Kate and Josey laugh.) Not so much when it, you know, restricts a little bit. So – 

Josey: Yeah. 

Tom: -- so yeah. I don't think it's specific to law firms, and I don't think it's specific to whether you are one to three years in the legal profession, whether you're fifteen to twenty, you experience your own metamorphosis sometimes in your career. And I think – 

Kate: Mhmm. 

Tom: -- for me, it was really important to identify that when I was in a role that didn't align with it, that I first talked with my manager or talked with, you know, whomever I needed to do to have a safe space, and then most often the time it worked out. Right? And sometime- And then when it didn't, understanding that this wasn't the end of the world either, right? And knowing there's that fluidity in the burnout stage too of addressing it but not letting it get the best of you. Right? Of we're all gonna have struggles in life, and how do you take the temperature of yourself and address that and pivot when you need to sometimes have more me time? Right? 

And then sometimes you're like, nope, actually, I wanna go give more to work, and then they're like, cometh. Come on back. You know?

Kate: Yeah. It can be transformational burnout.

Josey: Really is. And you said that the last one that you worked at was a small firm, right, Tom? 

Tom: Yeah. So the last firm that I was at, they… they hadn't even celebrated their fifth birthday. So they were newer in formation, and I mean, I love a startup life. I really love building things, and so that was great. Right? I but I think, to our point earlier of why was it transformational? It was because it was the last, like, stick in the basket of, “Nope. We're done with this.” Right? We're done with this burnout of personal work lifestyle choices.

Kate: Yeah. 

Josey: And how did you get into like, how did you find legal ops? I think that is the question that I know I because I didn't know about it, and I think so many people in our positions, especially wanting to stay in it, but not knowing how. I kinda found my – 

Kate: Yeah. 

Josey: -- I found my own little avenue, but it's… Legal ops, it wasn't even something I knew about. 

Kate: And you don't need a law degree! You don't need, like, any kind of degree really—

Josey: Exactly!

Kate: --for legal ops. Like, you can be come from wherever you want and just, like, bridge the gap.

Josey: Which is huge! Because as Tom said, as a paralegal, you feel like you hit your limit if you aren't gonna go to law school. You've-

Kate: I wanna hear more about that from both of you, by the way. Like, where- How did you find that spot, like, where was that spot for you? Where you were like, “This is it. This is the wall.”

Tom: It was in the burnout stage of knowing what my self-worth was, knowing what I wanted to ultimately do, what I'd worked so hard for but not knowing what it was. And so at that point, that's when I- this is gonna sound a little cheesy, right?- It was the community! It was me putting my head down and going, okay, let me research this. Let me, like, look into it. Let me dabble over here, dabble over there. Right? I-

I thought I was gonna go get an MBA. Because I thought that's what I maybe needed to do to level up to actually make the break from law firm in a senior role to an in-house role that wasn't – 

Kate: Mhmm. 

Tom: -- you know, I had over a decade of experience, so I wanted to be able to find a career also that I didn't have to start over with. Right? And so I thought I was gonna get an MBA and then talked with some people, and they were like, “No, that's not the route to go.”

And then that's when I started getting involved in associations and going to conferences and just trying to make time for webinars and when I couldn’t I would sign up for them and listen to them and my ex said I was really obsessed with this profession, and so yeah! And so I just totally fell into it, but not on accident. Right? I fell into it by saying, “I know I wanna be something adjacent and let me just keep scratching more and- and scratching more.”

And finally, when I got closer to the legal ops bubble, I realized these are my people. Like…

Kate: Here she is. 

Tom: This- this brings me so much joy. She's loud and proud, and it's warm and welcoming. 

Kate: It’s so true.

Tom: And it was because of the community, of going to one thing, and they'd be like, “Will you come back next time?” And I was like, “I've been always waiting for that question. Thank you.” Right?

And from there, just yeah. It- it just blossomed into the community- me falling in love with the community, me falling in love with the professional community, and then me realizing, “Oh, I'm actually really good at this too.” Right? Because- because of the background in law firm litigation and law firm corporate reorganization. And I was like, oh, this is fun. This is amazing. This is awesome. 

Kate: That's what's bananas to me about that attorney-paralegal divide and kind of the segmentation of law that I do think also contributes to burnout, is that you can have five years as Josey had, ten years of experience like you had, and hit a wall, and hit the end of that and then not know where to go. That is absolutely ridiculous. Any professional who's been in a career for a decade should have opportunities to continue to go further. 

And I've said it before, I’m sure I'll say it ninety thousand times: Paralegals know more about the law than any attorney walking out of law school. Like, it blows my mind that you can hit a wall after that amount of time and not know where to go. And not even know what your options are outside of going to law school or getting another degree.

Tom: And what's really fascinating is, yes, while some of the shit is absolutely deserved upon some people who look at title and hierarchy. Right? 

Josey: Mhmm. 

Tom: I will say it's really cool to see the next generation of attorneys walk into these in house roles, and they're like, “Okay, we don't believe what just was said. So what can I do to help you?” (Kate and Josey laugh.) Right? And I experienced that when I was at Credit Karma, I had the- it was an amazing it was an amazing culture and opportunity. And I was working at this, you know, emerging fintech company. right? And so the caliber of the attorneys that were there were often the ones that I was like, “Oh my gosh. You guys know about legal operations as well too? This is crazy!” And it didn't seem like it was forced. It actually was genuine.

Kate: I do want to get back to you because in the first episode, Josey talks about how she was called the secretary, and I'm very interested to hear if you had any of that experience as a man in the paralegal world? 

Tom: This is where I think the diversity issue comes into the overall burnout. Right? So for some people, there's more triggers than others.

Kate: Mhmm. 

Tom: And that's a real temperature gauge for how often you bubble over or when you bubble over. Right? 

Kate: Yeah.

Tom: For me, it's always been very difficult because I've had to either go all in or all out. Right? And so if I'm all in, I am this,  (Speaks in a low voice) “Hi, my name is Tom Stephenson, and I'm a paralegal and…” Right? And so I, like, I retract all of the goods of Tom. 

And then there are times in which I get to be my truly authentic self, and it…It has taken me a really long time to be that person, and I will admit that I've only started to become that person well-rounded in the last two to two-and-a-half years, in the prime of being way past burnt out, but then also now being at the point of… I wanna work hard, play hard, be rewarded for what I do, put my head down, help inspire change, do all of these things at once. And if I bake it right and I’m my most authentic self, then hopefully burnout won't ever happen.

I was always the person to say yes to so many things. And – 

Kate: Yeah. 

Tom: -- a lot of it was my profession. I'm I was a yes, ma'am, all day long.

And then that then blended into my personal life too, and that wasn't great either. And I think I experienced more times in the later half of my life, having that convergence, whether it's a friendship that was no longer working for me. Right? Or a personal relationship that was way past its expiration date, or family member that you need to make a difficult decision to maybe no longer engage with because it's not, you know, it's- it's- it's interfering with healthy boundaries, whatever that may be.

Yeah. I think I've experienced more than later half of my life, but it's also helped me mitigate the burnout.

Kate: Yes. 

Tom: Or if I am burned out, be very transparent. Like, she's checked out. She's going to Mexico for a week. Right?

Kate: Mhmm. She's over it. 

Josey: She needs a break.

Tom: Because I need to be able to rest my batteries because I'm recognizing the burnout and I'm gonna get ahead of the burnout.

Kate: Yeah. And I love what you said about finding your value, because that's kind of it's weird. It's like the point that I feel like I just gotten to. And I'm like thirty-six, right? 

Not that I've ever been a particularly, like, meek or unconfident person, but as far as work goes… Definitely- I also swapped careers about ninety times, so my impostor syndrome has constantly popping back up, because I keep putting myself into these positions that I've never had any experience at before.

Tom: If you wanna listen to an episode about impostor syndrome, head over to dearlegalops.com. 

Josey: I need that.

Kate: Yes. Please. Oh my God. I listened to- It's so- It's a really good episode. Legitimately, Tom is not paying us to say this.

Tom: Episode Ten!

Kate: It's so good. And- and anyone can speak to anybody. And it really… I- I finally felt when I just quit this last job and have just been focusing on this podcast, I finally was like, “Oh, this is… Here I am.”

I recognize my worth and my value and I have the confidence to do that. And that's privilege too, to be in a position where I can do that. But I- I've been in a privileged position for a while. I finally have the, like, recognition of what I can do and the confidence in it to- to actually have taken that step, but it took me a long ass time to get there, and it was a lot of external validation that I needed before I started internally validating myself in that way.

Tom: Get yourself a therapist, everyone. That's my best piece of advice here. 

Josey: Please do.

Kate: I feel like that piece of advice has come up on basically every episode. Get- go to therapy.

Josey:  I think I was really bad about it in our first episode. At the end, I'm like, “Therapist! Therapist! Thera-“ like, every other word. It was-

Kate: This is your public service announcement to go to therapy. If you can, if you can afford- But that's the other thing, therapy is expensive. It's not that easy for a lot of folks.

To wrap things up… What do you think are the best kind of first steps to take when you start thinking, “Okay, I've hit my I've hit my wall. I'm- I'm burning out.”

Tom: Yeah. I mean, burnout, it's gonna happen. My advice would be hate. One, recognize and address it. As soon as you see it.

For me, it was establishing those work-life boundaries. I love what I do. I love this community. I love this profession. And before, I will admit, sometimes I was the queen of yes, right, even in the corporate legal ops world.

And so I've really tried to work the last couple years on establishing those work-life boundaries. And that is only because I believed in my worth and I embraced my authentic self. And so if you can do all of that… I think the takeaway then from this is, how do you remember that every opportunity that doesn't go your way, it's an opportunity for growth and transformation? So just keep pushing forward, network, find what makes you happy, and then when you do, take some time to self-reflect. “Is this the journey I wanna continue to go?”

And hopefully, that's when you'll ultimately skew out of the burnout mode and into this, like, fresh innovative, or as my boss Pieter says, your center of excellence. It's my new favorite thing—

Kate: Ooo!

Josey: Oo, I love that!

Tom: -- to remind myself. Like what, where is my center of excellence? 

Kate: I love that you have a boss that's nurturing that. 

Josey: Right? What you did, Tom, of looking, researching, finding different ways to look at alternative legal careers, and not just feeling like your option is out or in the traditional law firm basis… I think that that is one of the the biggest things that I hope legal professionals, especially paralegals take away from this, is the way that you approached it and your ability to research and look for something else that felt right and authentic, but still in that realm that you wanted is really important. 

Tom: That's- that's the best part of community, and I think we're seeing this innovation of people wanting to level up their career when- at whatever stage they're at, and that doesn't mean that they're looking for a job. Sometimes they're looking to add just professional skills or network or start a podcast. Right? It's- it's all these things that I think is vital to you being able to get out of burnout and get into your center of excellence.

Kate: Yes. You do not have to stay in traditional law to use your experience or your degree or whatever it is you're worried about wasting. And you know what also if that's the only thing that's keeping you in it, that is not the reason to stay and be miserable.

Tom: Yes. A title is only a title. A company is only a company. At the end of the day, I went from Credit Karma to Legal.io, right? That was very difficult move for me to do, but it was because I was at that time realizing that I could have been on a path to burnout and I wasn't finding my center of excellence. 

Kate: Yes.

Josey: Mmhmm.

Tom: And it just it took a while to find that. But when I found it, it was like, I'm now saying yes. Yes. Like comforting “yes.”

Every day is just another opportunity for you to go, “Do I wake up, am I giving my best?” And I'm just excited to be at that point in my life right now. 

Kate: Yes! I'm so excited for you—

Josey: Yes!

Kate: -- to be there. And I hope we can help other people get there too. My little piece of advice is, like, register the moments when you're happy. Register those moments when you're not feeling that depth of burnout and figure out what you're doing in those moments, and see if there's any way to translate that into what you might want to do or where you might want to move. 

Find those things- and for me one of them was just the idea of the catharsis of doing this podcast. And it was like, when I started feeling kind of burned out again, it started creeping up on me, I just kept thinking like, “I wish I could do this as a full-time job.” It was the same thing when I transformed into tech. It was like, you know… It's something that I never would have thought of for myself before, and it's just like, landed really right.

And when that thing feels right, even if it seems crazy… Lean into it.

Josey: I love it. 

Tom: Love this.

Josey: Well, I think this is a great place to end. You guys with all this – 

Kate: Yes. 

Josey: -- amazing words of wisdom and just mic drops that have happened, my god. I'm gonna be standing in front of my mirror tonight, like, “Center of excellence.”

Kate: Tom, thank you so much. 

Josey: Oh my god, Tom. 

Tom: Y'all are the best. Thank you guys so much.

Kate: Love you!

Josey: Love you, Tom. Bye!

Tom: Love you, bye!

Outtro

Kate: The Legal Burnouts is produced by me, Kate Bridal. Our music is by Keegan Stotsenberg. Our art is by Growlforce. Thanks for listening.