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Episode 207: Want To Do Something Else (& Not Practice Law)?
Have you ever thought about leaving the life of a lawyer to do something entirely different? Yet you don’t because:
- What if you decide it’s a mistake?
- How hard would it be to come back?
- Would you be starting all over again?
Today’s guest did exactly that. She started in Big Law and left a few years in to start her own non-legal business. Not because she was unhappy as a lawyer, but because she had a dream.
And then, when she realized she wanted to go back to practicing law, she got an in-house position (without skipping a beat).
Listen to today’s inspiring interview to learn:
- Why doing the “other” thing is worth it (even if you go back to the law later).
- The mindset shift you’ll want to make when leaving law behind.
- How to sell yourself should you decide to go back to practicing law.
- How business experience can enhance your legal skills.
- Important advice for any lawyer considering an alternative career.
About Heather Stevenson
Heather Stevenson is General Counsel at Red Cell Partners. Known for her approachable style and entrepreneurial mindset, she recognizes the importance of trust, creativity, and decisiveness in addressing the most complex business and legal challenges.
Heather’s entrepreneurial mindset is evident when looking at her bio:
- From joining Teach for America before law school… And then taking a non-traditional path out of private practice.
- After starting out as a litigation associate with Sullivan & Cromwell, she left law entirely to start a plant-based juice and smoothie business (called Thirst Juice Co), where she successfully opened multiple Boston-area shops, managed 30 employees, and served hundreds of thousands of drinks.
- Later, she decided to get back into the law. But not as a traditional private practice attorney. Instead, she went in-house, where she now blends her legal skills and business know-how.
Heather is passionate about and regularly mentors junior lawyers on how to navigate non-traditional and in-house legal careers.
Connect with Heather at:
Episode Transcript
Heather Moulder 00:57
Welcome, everybody, back to Life & Law podcast. This is your host, Heather Moulder. And today, we have another Heather on the show with us.
I want to introduce you to Heather Stevenson. She is the General Counsel at Red Cell Partners. Known for her approachable style and entrepreneurial mindset, which that second part we are going to get into a lot today, she recognizes the importance of trust, creativity, and decisiveness in addressing the most complex business and legal challenges. Heather’s entrepreneurial mindset is evident when looking at her bio.
From joining Teach for America before law school and then taking a non -traditional path out of private practice. She started out as a litigation associate with Sullivan and Cromwell, left law entirely to start a plant -based juice and smoothie business, and then later ended up getting back into the law, but not as the traditional private practice attorney. Instead, she decided to go in -house, where she now blends her legal skills and business know -how. Heather is passionate about. and regularly mentors junior lawyers on how to navigate non -traditional and in -house legal careers. She recently started a newsletter for in -house lawyers looking to build successful legal careers on their own terms called Outside the Box.
And by the way, there will be a link in the show notes to join her newsletter. I’m excited to have Heather on the podcast because I know you’re going to learn a lot from her about how to achieve legal success on your terms, regardless of whether you’re in private practice or in -house or are thinking of something even in between. Welcome, Heather.
Heather Stevenson 02:26
Thanks so much for having me, Heather. It’s good to be here.
Heather Moulder 02:29
I am, I got to say, a huge fan. I’ve been fangirling on like forever. I’ve followed you forever. I love what you talk about. You’re so specific to your niche of I’m talking to in -house lawyers. But I got to say to all the private practice lawyers listening out there, Pretty much everything she puts out there is applicable to all of you. So no matter where you are, highly recommend following her on LinkedIn. You’re going to learn a lot. And frankly, I think you’re also going to learn some good information on how to better approach your clients because you get that in -house perspective.
Heather Moulder 03:08
Even if you don’t want to sign up for the newsletter, I know we lawyers don’t like to sign up for newsletters, follow her on LinkedIn because there’s a lot of great information out there. So I just wanted to get that plug in there because I think it’s kind of important.
Heather Stevenson 03:19
Thank you. I appreciate it. And I love creating the LinkedIn content. You’re right. It’s meant for in -house lawyers, but I hear from a lot of private practice lawyers who say either we benefit from this because it applies to us too, or, oh my goodness, thank you for letting me know how the clients are thinking about what I’m doing.
Heather Moulder 03:36
Yes, I’m sure you’ve noticed that every time I comment, it’s like, this is applicable to a lot of private practice lawyers. And here’s why and how. And I say it that way so that when my people who are private practice lawyers see that go, oh, maybe I need to pay attention to her post now because it can help me. So that’s why I do that. But yeah, so I wanted to go back and maybe start from the beginning.
Heather Moulder 04:01
What made you even want to go to law school?
Heather Stevenson 04:05
So both of my parents are lawyers. My mom is in her 70s and still practicing. My dad retired a number of years ago.
Heather Stevenson 04:14
It was kind of what I was always going to do. I just, you know, early on assumed I would do it, went through various periods of exploring other interests. I was an urban studies major in college. At one point, I thought I might want to either be an academic or go into urban planning, did Teach for America to give myself a little bit of time to kind of, you know. think and space before rushing into law school just because it was what was expected. But ultimately, I loved the things that you do in law school. And that was kind of why I went, which is probably not the best career strategy, even though it worked out well for me. So I love reading, writing, analytical thinking, you know, oral advocacy, that type of thing very much might think of as what litigators do. And so I thought that that would be appealing. I also am quite similar personality wise to my mom who loves it so much that she just, you know, hasn’t stopped even though she could have at this point. So that’s how I ended up there.
Heather Moulder 05:16
Yeah, it’s funny you say I loved what you do in law school because I do think a lot of lawyers love the law school piece and don’t realize that that’s not exactly what you’re doing when you practice. Now you do utilize those skills, but you do it differently. And there’s a lot of other things too. And I would say this, you probably start utilizing more of that if you want to, as you progress in your career and can actually build a practice the way you want, depending on the type of law you practice, right? Like you have the ability. So for example, when I started out as a baby lawyer, it’s corporate finance. I spent most of my time doing resolutions and omnibus certificates, and it was the most boring work in the universe. Like, I just remember having a conversation with one of the partners two years in. I can do more than omnibus certificates and resolutions. Can you please let me do it? You know, and finally that got them to go, OK, yeah, sure. But so there’s a level of, you know, it depends on your like where you are. But and what control. But that’s not all you do. And there is a difference. So I like to point that out for any of my people out there listening who are in law school. Like, it’s not that you won’t use those skills, but you use them differently and you use others too. And there’s other aspects to practicing that are different than school.
Heather Stevenson 06:40
Totally. I mean, I think my favorite part of Luke. law school ended up being moot court. I loved drafting the briefs. I loved oral argument. It was so fun. I loved having to switch sides a bunch of times. And then I got to a big law firm as a litigator and I did not speak once in court my entire time there.
Heather Moulder 06:59
Well, I will tell you, I know a number of partners who are quote unquote litigators who’ve never been to court. Well, that’s wild, but I guess
Heather Moulder 07:06
it happens. It’s insane to me. Like, how
Heather Moulder 07:08
do you call yourself a litigator again? But they do different aspects and, you know, to each their own. I think, you know, but people can take more control, which is what we’re to get to. So when did you, how long had you been practicing when you made the decision to leave and start your own business? About three years. Let me just say that was super brave. It’s not a typical way that lawyers think. Most lawyers who are unhappy think, well, I’ve just got to go from private practice to another firm, maybe a different sized firm, maybe a different practice area. Maybe I should go in -house. They don’t think, I’m going to go start a completely different business that’s totally, totally different than anything I’ve been doing. So how did you decide what business you even wanted to do? And get yourself into the mindset of being willing to do it.
Heather Stevenson 07:58
Yeah. So I should start by saying I did not hate being in big law or being a litigation associate. It was fine. There were aspects of what I did that I really liked. The cases I worked on, even if my part was small, were really important. I liked my colleagues.
Heather Stevenson 08:16
But when I looked at a lot of the senior partners and their lives, and then I looked at what it took to get there, it didn’t feel worth it to me. There were too many people with or with tough home lives or who miss their kids’ birthday parties or whatever the thing is, every stereotype you’ve heard, I was seeing it. And then I was seeing the grind that happened, you know, to even get there. And I thought that if I were to be, you know, 65 looking back on the past 40 years, I didn’t want that to have been my life. But I wasn’t miserable. I just wanted to do something else. I did think. briefly about other options, like going to a smaller firm, going to government. I really didn’t think about going in -house. I don’t know why. I think probably just because I was relatively junior and a litigator, so it wasn’t an obvious path.
Heather Stevenson 09:08
But the juice bar thing was almost more of a pull for me than something that I settled on as specifically an alternative. So my husband and I,
Heather Stevenson 09:20
We’re training for an ultra marathon the year before we got married and then soon after that ultimately left the law. And we drank a ton of juices and smoothies and they were getting big in New York at that point and had already been big in California and other parts of the country, but hadn’t really come to Boston yet. And we love these juices, smoothies, acai bowls. And saw this market gap in Boston. And we were also big foodies. And we’d always kind of joke, like, wouldn’t it be funny if we started a restaurant? We didn’t have any of the training you need to start a full -on restaurant. But it kind of went from, okay, there’s been this longstanding joke to, well, maybe I want to do something different than practicing law in a big law firm. And here’s this opportunity. And wouldn’t it be cool?
Heather Stevenson 10:10
And what’s the downside? Right. So at that point, we didn’t have a mortgage. We didn’t have kids. We didn’t have law school loans. So that that made it a lot easier. So it was kind of one of these things where we thought, well, the worst thing that will happen is we will very embarrassingly fall on our faces and then we’ll just pick ourselves back up and do something else. And so it really started as a joke. about something we were passionate about but didn’t think we could do and turned into let’s go ahead and actually do this.
Heather Moulder 10:42
So were you, it’s interesting to me, you even acknowledged, okay, the worst thing that can happen is it won’t work out at all. We pick ourselves back up and then we figure out what’s next. It’s just a very different mentality. You didn’t seem to care a lot about, well, what are others going to think of me? Will they hire me? You were like, so what?
Heather Stevenson 11:02
Yeah. And, you know, people ask me about that a lot. And I try to figure out where it comes from, where this sense of like, it’ll be fine. People can judge me or not. And I’m OK with it. And I don’t know. But I can say that the more I have done things that people think are a little bit weird. And I started doing things people thought was a little bit weird long before the juice bar. The more I do it, the less I care if people think that. It’s not what I should be doing or it’s a weird thing to do because it keeps working out for me. Even when it doesn’t work out, you know, we’ll talk about it. We ultimately closed down Thirst. It was the best move I ever made, including for my legal career.
Heather Moulder 11:41
I actually think there’s something in there that’s very helpful if people are willing to accept it. So people often ask me, well, how did you? decide to leave law? How did you? And I think for me, it was, I’d always had in the back of my head, I don’t want to be 65 and practicing. I wanted to practice, but I didn’t want to retire as a practicing attorney. And I’d kind of lost sight of that when I got into the rat race of climbing the ladder and building my practice. And frankly, I built a practice I really loved. I had a pretty balanced life as far as lawyers go, and I was able to make it work. But that thing was still in the back. And after my cancer journey,
Heather Moulder 12:20
I realized all these things that we say are super important really aren’t. And I can handle a lot, right? It’s this acceptance of it’s fine if you fall down. It’s fine if you have a setback. It’s fine. Like it will happen at some point. And I don’t know when or how, but you learn from it and you can move forward with it. And it’s this, I call it a fail forward mentality. You actually, it’s not that you want to fail. But you go in knowing it’s possibility. I probably will at least make a lot of mistakes, but it’s OK. Like, it’s OK. It’s part of being human. It’s part of learning. It’s part of getting better. It’s that mindset. And that’s a choice, I think, at the end of the day.
Heather Stevenson 13:05
I agree. And I think it’s one that is particularly hard for lawyers because. This is a complete overgeneralization, but it’s going to get a lot of your audience. We did a really good job in high school, like grades wise and sports and student leadership so that we could get into a great college. And then we did it all over again in college so we could get into a great law school and then from law school to a great firm. Some version of that applies to so many lawyers. And so when all of a sudden you’re told like, it’s okay if you’re not perfect, it’s okay if you don’t get the top possible score. I mean, I literally, took some classes in college because I knew I could get A’s versus what I wanted to learn, which is so counter to the point of college. But once you realize that it doesn’t really matter and it’s okay to mess up, like you said, it makes a huge difference to what becomes possible for you.
Heather Moulder 13:59
It does. And I think there’s this sense of we’re doing what’s great, quote unquote, right? We’re going after all the greatness as defined by other people. Without stepping back and going, what does greatness mean for me, the human being, based on the life I actually want to live? And I think if more lawyers would just do that, they’d open up more opportunities for themselves. They’d build very different practices. They’d be a lot happier. I think probably the number one reason we have such problems in the legal field, it’s because of that thing that we’re always going after. the greatness as defined by everybody else, because we are the biggest rule followers. And we’re also big people pleasers and gold star, like we love the gold stars, right? I loved the gold star when I was a kid, whenever it was put on my paper, it made me feel good. And we want affirmation from other people. And so it’s the mindset shift of, I still want to please others to some extent, right? I want to serve others. I want to do my best for others, but not because I need them to approve of everything, but because I’m doing it. Based on who I am and how I want to show up, there’s a switch there that we have to switch in order to make this work.
Heather Moulder 15:15
Totally agree.
Heather Moulder 15:17
Okay. So tell me a little bit about, so you ran the juice bar for a couple of years and you ultimately decided to shut it down and go back to the law. How did you make that decision?
Heather Stevenson 15:27
Yeah. So I didn’t actually shut it down to begin with. After about three years of running the juice bar, my husband and I had our son. And everybody who hears this story is like, wow, Heather, for a smart person, that was really dumb what I’m about to say next. I assumed that. it would be a good plan for me to keep running the juice bar. We had staff, we had kind of managers in place, but not super senior level managers, that I would keep doing all that while being the primary caretaker for my son during the day. No nanny, no daycare, any of that. And that was terrible. I’m bringing my infant son out to our location. That’s a 40 minute drive from our house. I’m trying to get him to the one downtown. I’m trying to talk to people with my… baby in the carrier who needs to like nurse every 30 minutes because he’s the hungriest kid you’ve ever seen. I mean, it was just really, really challenging was piece one. And then I had been starting to kind of just miss thinking like a lawyer. There is something about the type of like analytical thinking and reasoning and everything is logical that I really had always enjoyed and doesn’t apply in quite the same way in a business. I think in a business, of course, there’s lots of analytical thinking, but there’s a lot more like experimentation as well. And I just missed it. So I got to a point where I thought, well, I can’t really do like the way we’re running this business. I can’t afford to hire full -time care for my son. So if I’m going to have a solution that works for my life, it can’t be exactly this. And if I miss being a lawyer, why would I not do that? So what we ended up doing was coming up with a plan to get better, not better, but just more leadership support in place at the juice bar. And then, you know, deciding to go try and get a job as a lawyer, which started out very broadly, just like as a lawyer.
Heather Stevenson 17:25
Okay. And going from there, but it was a mix of missing being a lawyer and like the setup I had for my life was not workable.
Heather Moulder 17:36
Was there a concern, because I hear this a lot from attorneys who say, I would like to try something out. I’ve had this side thing, this side gig I’ve been thinking about forever. And maybe I’ve even started it. And it’s starting to take off. And it’s becoming clear that if I really want to make something of it, I got to step away from my law practice. But I’m terrified of doing that because what if it doesn’t work out? How do I come back? There’s this assumption by lawyers, especially, that they cannot leave. And come back very easily. And I know I said very easily. And in some cases, it is harder for people to get them to hire you. But I don’t think that’s all true. And I think there’s benefit that you could sell if you understood how to sell it correctly. Not to everyone, but to the right people. So it stops them. In a lot of cases from ever going to do the thing and they let that thing just kind of fizzle out. And then they always end up in this regret phase of I never did that. And I wonder how it would have turned out. So tell me, did you have those concerns of are people going to question me? Or is it going to be hard for me? Did you get any pushback as you looked? Like, what was your experience around that? And how did you navigate through that? So I completely
Heather Stevenson 18:51
understand the concerns. They are totally valid. And I’m sure there are a lot of people who would have laughed me out of their office or inbox or whatever the thing is if I had tried to apply for a job there. Because why on earth would you go to all the prestigious schools and get into the law firm and then leave and want to come back, especially so quickly? The way that I was able to sell myself, and it’s true, it continues to be benefit.
Heather Stevenson 19:21
is understanding the business and having run a business makes me a better lawyer. And I can get into details of that. But I started my process by just kind of starting to put myself out there in the Boston area. I had only practiced law in New York before. So I started, you know, I went to some. events for lawyers. I started poking around on, I think it was Indeed then. That was a job board. I don’t know if that still exists. It does. Okay. Good to know. And I ended up actually relatively quickly, so this is where luck comes in, finding this job that seemed really appealing to me at the Boston Globe.
Heather Stevenson 20:04
And if you’re not from Boston, just like, okay, that’s some random newspaper. If you’re from Boston, like I am, that’s really cool because this is just an institution in Boston. And the job was basically reviewing and negotiating kind of routine contracts, not quite just procurement, but pretty close to that. And I had been a litigator before. So if you actually read the job description and took only my law firm experience, I was not qualified. I wanted like three to five years of corporate. transactional experience in a firm. However, I had been negotiating contracts for bananas and almond milk and all things in a way that translated really, you know, smoothly, or at least I was able to convince my boss would translate smoothly. And so that ended up being how I got that job. So I had a connection that got me, basically got him to talk to me.
Heather Stevenson 20:59
When I got in there, I said, look, like I’m smart. I’m hardworking. I will do whatever you need. I can review these contracts. Like it’s going to be easy because I’ve been doing. this for the last three years. And also, by the way, I can help you understand how your business colleagues are thinking about these things because I built it. And I understand now how to be a really effective advisor to a business, not just somebody who takes this like one minuscule piece of what the business is doing and kind of opines on it. And there’s a really big difference. And I was lucky that Dan, who was the GC at the Globe at the time, like, took my word for it, I guess. And I would say took a chance on me and I got that job and went from there and it was terrific. And I was there for several years.
Heather Moulder 21:49
So I hear a couple of things in this. Number one, I hear a lot of this had to do with your mindset and self -confidence because you, you did not allow.
Heather Moulder 22:00
The lack of practicing for a couple of years convinced you that you were less than and that somehow people should disregard you, which I think a lot of lawyers convince themselves. And so they’re starting behind to begin with. They can’t even sell themselves. They can’t even, right? So you have to have that. You have to acknowledge, look, I have real experience that has helped me, has given me. A, negotiation experience, which is totally applicable to the law and how you negotiate contracts. And then B, business experience, which a lot of lawyers lack. And you can be helped by it. So you knew that. You were confident in that. And it enabled you to sell yourself better. The other thing I’m hearing is because of that, you weren’t afraid to just go out and network and ask and get those introductions, ask for those introductions. And I think, I know you say luck. There was luck. There’s always luck involved in these things. My biggest client that I ever had that I grew hugely as a private practice lawyer was through luck. But I know that they came in because of how I sold myself. They came in because of how I, you know, sold the firm. And then they came in with us being the number three law firm to back up others. And I grew them in a three -year period to be their number one law firm and massively. Like that was on me, right? So like… Everybody says it’s luck. Well, a lot of things are luck. But you’ve got to take it on to open up the doors and see the opportunities. And then you can take advantage of them. And if you don’t have that right mentality, then you’re not willing to go out there and you’re not willing to ask and you’re not willing to open the doors. And it’s not that mindset is the end -all, be -all, but it is the foundation of getting out there to see what there is and then having the confidence to say, yeah, I can do this. That’s what I’m hearing.
Heather Stevenson 23:48
Yeah, no, I completely agree with you. And I think it’s also kind of like the optimist’s mindset of I’m sure there’s a bunch of stuff that went wrong in connection with trying to get a job. And I don’t remember anymore. Like, you know, I met lots of people who I probably said, hey, I’d love to work for you or like, can we get a coffee or whatever? And they never got back to me or whatever the thing is. And it has no impact on my life. So I don’t really think about it. The only thing that mattered was having one person say like. Yes, I have a job for you and I believe in you enough to hire you.
Heather Moulder 24:22
I’d love to hear, because you opened the door earlier. You said we can talk about that if you want. And I do. This whole idea of it is really helpful to have business experience and understand how to run a business when it comes to being a lawyer. I think, well, I know you’re correct. I’m an econ major. And the business stuff comes easier to me, I think, than a lot of lawyers. It just always has. It’s why I have the business I have now, right, in helping lawyers build their books and scale and deal with the business side. And I think there’s lot of lawyers who discount themselves and don’t bother to learn it when they could, and they would be even better lawyers. But I really want to hear your take on it because I know there’s firm leaders. listening to this podcast that aren’t willing sometimes to take a chance on somebody like you. And I really want them to rethink that because I think they’re doing their firms and themselves a disservice along with that individual. So tell me your thoughts around that and how much you think it has impacted how you show up now in your current roles. Yeah.
Heather Stevenson 25:36
So I think it has impacted at kind of macro and micro levels.
Heather Stevenson 25:42
One thing that happened when I was at Thirst that I think back to often when I think about how I am kind of delivering services to my in -house clients is I asked our outside lawyer a kind of offhanded question. I couldn’t even tell you what it was now. It was something about what certifications we needed to sell some type of juice. And I just said, could you take a quick look? And I got back a 10 -page memo.
Heather Stevenson 26:10
It was like a $5,000 or $6,000 bill, which for a company of our size, particularly then, I don’t think we’d even opened yet, was horrible. And I ended up going back to her. We fixed it. In the end, it was fine. But since then, I have been, as a lawyer, very intentional about what is it that the client actually wants. In that case, I wanted to understand, could I sell this juice without… like jumping through a bunch of loopholes or what I have to, I didn’t want to pay $6 ,000 for an analysis of the history of the law.
Heather Stevenson 26:46
And so I think, you know, in -house I’m not billing for my time, but I think about it in terms of how much of my time am I spending responding to something and essentially requiring my in -house colleague to spend of their time, because if I send them a 10 page memo, they have to read it for it to have value. So that’s just one little piece, but then. I think understanding how businesses work in terms of, OK, they’re balancing revenue against cost. They have specific goals that vary from quarter to quarter or at least year to year. And any of the legal advice you are being asked to give is meant to support those goals. It’s not its own thing. And that is so different than at least what I was doing as a litigator where I was. deep, deep, deep in the law of shareholder derivative suits and whether Delaware directors were interested or independent. And I did not think about what my client’s big picture business goals were. I didn’t need to. And I think similar things happen for corporate law firm lawyers too. And so tailoring all my advice to be, I understand your business goal. And here’s how the law impacts that and how we can use it to benefit your goal was a huge mindset shift that at the macro level is really important. Then at the more micro level, there are lawyers who will review a contract and not pay attention to things like what is the dollar amount? What are the payment terms? Under what circumstances can this vendor not deliver and still get paid? That type of thing, which aren’t what we’re taught to look for in law school, but actually are the most important part to a lot of businesses. And so that’s something, you know, hopefully people are hearing this here at once and now they just know it. You don’t have to go run a business to understand that part. But it’s so important.
Heather Moulder 28:44
Okay. I hear a lot of things here that I want to point out. So number one, all lawyers, whether you’re in -house or in private practice, you are going to be a much better lawyer for your client. And I personally believe you need, ethically, to step back. And not just if a client asks for something, you need to ask more questions and gain very specific knowledge around what it is they’re actually asking for. Because we make a lot of assumptions and we go down these rabbit holes. That’s what it sounds like that lawyer did, right? She assumed instead of asking some more specific questions that, no, no, no, no, just take an hour or two to go look this up and let’s have a conversation and get a basic understanding of what I need here. And if I need you to do that later, I will have you do it, but don’t assume. And also start thinking about what’s the business? Does this make sense? Before you go down those holes and ask the questions, okay, here’s what I’m hearing. Here’s what I’ve done. Here’s what I’m thinking. That will save you so much time, energy, and money. This is how write -offs happen a lot of times as we make these assumptions and we just go down these rabbit holes.
Heather Moulder 29:56
The other thing I’m hearing is, And I’ve said this for a long time. Lawyers, even in private practice, need to have better understanding of who their clients are. And they need to understand the business. They need to understand how the business works. They also need to understand the long -term goals, the short -term and long -term goals, and the risk profile of that client. And have honest and open conversations around how all of that shapes the legal strategy.
Heather Moulder 30:26
And I will tell you, I did do this with my clients. And I keep, I tell people this all the time. It is the biggest business development. Like if you do this for your clients, you will grow your business a lot easier because people will see that. They will see that you’re not that person. The reason I grew that one. a client from number three to number one and the others got crowded out is because they would tell me, well, we have so -and -so who I’ll give them a scenario and then they’ll come back to me in three days and say, well, you have option A or option B and they give all these things under each option. Here you go. Tell me what you want to do. And I would be like, not three days later, go, okay, give me a couple hours to think about it and let’s have a conversation. And then I would say, okay, here are your couple of options that I’m seeing.
Heather Moulder 31:17
let’s talk about your risk around, you know, what do you want? Let’s talk about your goals. Let’s talk about, and I would actually give them, okay, giving what you’re telling me, I think probably option B makes the most sense. Ultimately you can make, and here’s why. Like I would actually give them that opinion. They didn’t always take it, but they really valued that I understood their business. I understood the risks of all sides. And I took a stand and I told them why.
Heather Moulder 31:44
There is a way to do this, even as a private practice lawyer. And I think you are showcasing really well, based on your experience, how that comes into play. And I think that actually applies to litigators, too. Like they go into these rabbit holes of these are the defenses and start talking to your clients more. Make sure you’re talking to them about what you’re thinking and why and get a sense of what they really, what do they want to pay? What do they want to do? The other thing that I love that you pointed out is. We don’t tend to pay attention to the details around the business deal just to make sure that’s right. Is the structure right? Are the terms correct? Like the basic things. We’re looking for all of the hidden stuff in the verbiage, right?
Heather Stevenson 32:26
Totally. And I think it’s really interesting. Now, and I’m not going to take us in a totally different direction, but as we as lawyers start to use AI more and more. Oh, yes. What are the parts of contracts or agreements or whatever the thing is where we as lawyers really need to be? reading very carefully ourselves, regardless of whatever our tool says and what are the places where we can say, okay, we’re just double checking. It’s not doing anything crazy. And the business terms, in my opinion, we always need to very carefully check with human eyes, regardless of how good the tool is. Maybe that’ll change in 10 years, but not yet.
Heather Moulder 33:05
I don’t know. I think AI scares me a little bit. This over -reliance on them and thinking it’s just a tool. It’s not just a tool, by the way. It is a tool, but it’s not just a tool. So you got to careful how you use it and you can’t trust it. I don’t mind people using it to summarize as a starting point so they have a better understanding, but I do not think that takes away your obligation to read the whole thing and make sure it’s right.
Heather Moulder 33:33
Yeah,
Heather Stevenson 33:34
no, I totally agree with you, but I think there’s different levels of how much attention is required. And I think making sure, you know, those numbers say what you think they say and the terms are there is essential.
Heather Moulder 33:49
So what would you say if somebody came to you and said, okay, I’m intrigued. I think I want to go. out and start this other side, you know, this business I’ve kind of thought about on the side or I’ve been doing on the side, I’m leaving. Is there any final like piece of advice that you would give them when, when they’re going out to do something like that? So I
Heather Stevenson 34:11
would say two things. The first is, you know, build yourself a financial cushion in case it doesn’t work out. And then once you’ve done that, go all in. Like, I am not one to say, oh, try and keep your legal network warm while you’re off trying to build your juice bar or whatever the thing is. Because I think if you are starting your own thing, you really need to 110 % dedicate yourself to it. It’s going to be exhausting. It’s going to be harder than anything you were doing before. You’re going to work a lot more hours for a lot less money. You don’t have time for extra. So make sure you have the safety net in place and then ignore the lawyer stuff. If you have to come back to it later, you figure it out later. That’s not your job while you’re trying to go all in on your business.
Heather Moulder 35:00
I would second all of that. I would say, so when I started this business, I knew for two years and the reason it took me two years was because we were saving like crazy so that we could have the cushion we wanted in case this did not happen. And I wanted to give myself a two year runway before I made real money. in this business. Thankfully, that’s, and I was right. It took about two years to get to where I wanted to be. So don’t just, I think when you jump ship too early and just trust it’ll happen without the financial stability, it is so stressful. You do things out of neediness. You don’t make the same decisions. You want to make sure you at least have that cushion. Totally agree with that. The other thing is I agree with y ‘all in, and I would say this. You can reconnect with people pretty easily. It’s been shocking to me how quickly, even me, how quickly my clients, when they come to me and say, I haven’t talked to this person in 10 years or I haven’t, but they’re like this perfect potential client. And it’s like, all right, we put together a plan on how to reconnect. And it’s very simple and it’s very easy. And over time they reconnect more personally and then it builds and they get the business eventually oftentimes. So it is not that hard to do. Don’t worry about that. Go all in on what you want to do now. Yeah,
Heather Stevenson 36:16
agreed. And I think also if you’re going off to do some cool thing and then you want to talk to your old connections, everybody’s all excited to hear about your cool thing, especially if you’re a private practice lawyer who goes and does something. And then you want to talk to your private practice lawyer friends who like half of them have been secretly thinking about doing their own thing for the last decade.
Unknown 36:38
Very true.
Heather Moulder 36:41
Absolutely true. Well, thank you so much for joining us for this conversation. I know that a lot of the audience is going to get a lot out of this, whether it’s applicable to a current practice or something else they want to try out. How can people, if they want to connect with you, find you?
Heather Stevenson 36:58
So I am active on LinkedIn. And that’s the best way to get in touch. And I also have a newsletter you mentioned at the beginning. It’s called In -House Outside the Box. And if you happen to be an in -house lawyer or know an in -house lawyer, I know that’s not the primary audience. Please check it out. I give actionable tips for how to be a more effective in -house lawyer while building a career that works for you.
Heather Moulder 37:24
It’s like you’re the other side of me, but for in -house lawyers is what it sounds like. Your language is very similar. The way you talk about it is very similar. I love it. It’s why I long wanted you on this podcast. And I’m glad we finally got to connect for this. Thank you so much for being here today.
Heather Stevenson: Thanks so much for having me.
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I’m Heather Moulder, a former Big Law partner who traded in my multi-million dollar practice to help lawyers achieve success on your terms. Because real success includes a real life.
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