Sarah Cottrell: Hi, and welcome to The Former Lawyer Podcast. I'm your host, Sarah Cottrell. I practiced law for 10 years and now I help unhappy lawyers ditch their soul-sucking jobs. On this show, I share advice and strategies for aspiring former lawyers, and interviews with former lawyers who have left the law behind to find careers and lives that they love.

Today I'm sharing my conversation with Ashley Carlisle. Ashley is the CMO of HyperDraft, that's the chief marketing officer. For those of you who are thinking about a potential career in marketing, this is a great episode to tune into. Let's get right to my conversation with Ashley.

If you like the idea of the Collab but would like to do some one-on-one coaching in addition, then you should consider the Collab Plus One-on-One Program. It's a hybrid program which combines the Collab with one-on-one coaching, three months of one-on-one support from me to help you move through The Former Lawyer Framework.

The way that it works is that you get everything you get in the Collab including lifetime access to the Collab, you get four 60-minute one-on-one coaching calls with me that you can schedule anytime over three months. You also get a free video resume review where you send me a copy of your revised resume during those three months and I will send you back a video reviewing it giving suggestions for how to change, add, etc, and then you're also going to get two free assessments that are otherwise paid: one is a strengths assessment and one is a personality assessment.

The goal of the Collab Plus One-on-One Program is to give you access to some one-on-one coaching and also all of the resources of the Collab. So, if you're someone who's thought about the Collab but is also drawn to the idea of one-on-one coaching, then definitely go to the website and check out the information. It's formerlawyer.com/collab-plus.

Hey, Ashley. Welcome to The Former Lawyer Podcast.

Ashley Carlisle: Thanks for having me.

Sarah Cottrell: I am excited because you are here to talk about moving into a role that is something that comes up quite a bit with people who I work with and then also just listeners of the podcast. You're currently in a CMO role. Is that the actual name or title that you have?

Ashley Carlisle: Yes. That is my actual title. We are a small team so I feel like none of our titles really encapsulate all the work we're doing. I'm doing a lot of random things. I have many hats on but yes, that is my title I guess formally.

Sarah Cottrell: Okay, perfect. Why don't we start with you introducing yourself to the listeners more generally and then we'll go from there?

Ashley Carlisle: My name is Ashley Carlisle. As you can probably tell by being on this podcast, I did practice practice law. I was one of those crazy people who knew I wanted to be a lawyer at a young age and ended up doing it in a Biglaw capacity.

I worked in Biglaw for I guess five-six years. It's all a blur now. Then I ended up connecting at my last law firm with the now CEO of HyperDraft, which is the company I'm at now. We are a legal tech company that helps organizations with document and workflow automation, so basically making legacy processes less cumbersome.

Through that, I've been on this journey of the transition from Biglaw to business generally and then trying to teach myself how to be a marketer while having to market all at the same time. I've been on that journey for about a little over two years now I guess. It flies by so it's weird to say that but that's where we're at.

Sarah Cottrell: Time flies when you're having fun for something.

Ashley Carlisle: Definitely.

Sarah Cottrell: Okay. Let's talk briefly about all the way back in the beginning because you said that you knew you wanted to be a lawyer from a young age. Can you talk a little bit about how that came about?

Ashley Carlisle: Definitely. It's something that I'm often asking my siblings and family members about because memories are weird. You're so convicted in how you remember things and as an adult, you're like, “Did I make that up?” but luckily, you have the benefit, I was just in Texas with my family over Thanksgiving, I asked them about this, and they were like, “You were not weird. Your memory is correct.”

I think before this but the first proof I have is at 11, my fifth-grade yearbook asked what I wanted to be for a living and I said, “Lawyer/politician,” because I thought it was one thing. Since then, I have journals and journals of how I was going to be a lawyer.

That was my only goal and looking back on it, I've talked to others who have had that weird idea of “I want to be a lawyer or doctor at 11” and they end up doing it and some have mixed reviews on “Was that really my dream? Was that really my goal? Where did that come from?” I don't regret it. I really liked all the steps.

It was stressful. I put way too much pressure on myself but I think I was meant to do it and I don't really know where it comes from other than I thought Xena, the Warrior Princess was Xena, the lawyer princess. I dressed up as Renee O'Connor for a couple of Halloweens. I had every birthday party as a child living in Austin, Texas at the state capital.

I had this weird obsession with rules and reverence for bodies of law. I don't know where that comes from but that's still the quirky part of my personality today. It's just been a nerdy journey for me where I ended up actually acing the bar in two jurisdictions. California was way worse but done hopefully.

Sarah Cottrell: Yeah. It's so interesting. I think there are a lot of us who became lawyers who would probably relate to, “Yeah, I had a lot of very nerdy interests even at a young age,” and like you said, once people actually start practicing law, it can be very different. Some people are like, “This is great,” and some people are like, “Hmm, perhaps my 11-year-old self was not totally up on what this was going to be like.”

I'm curious for you, you got into law school, you've wanted to be a lawyer for a very long time, how did you decide what type of law, what was that process like?

Ashley Carlisle: Oh, thank goodness, I've been through a lot of therapy.

Sarah Cottrell: Yes, therapy.

Ashley Carlisle: Yes, therapy. I think all lawyers should be in therapy. I think you have that sentiment as well. Law school was so hard for me because I had worked towards going to law school for so long that I had built up these Disney expectations that obviously were not going to be met by anything based on reality.

It was a grieving process of how wonderful I thought it was going to be because law school is tough and there's a reason for that. It's competitive and not everyone is super nice and want-to-be-my-best-friend type of vibe. I think I had a grieving process of the expectations.

Also, I had worked so hard for that that I’d never thought of the next step. I never thought of my next set of goals. I even had that kind of crisis as well once I started in Biglaw. I think that's something that I talked to a lot of lawyers and they struggle with is it takes so much effort, confidence, and grit to get from stage to stage that there is a period of, “Well, what do I want to do next? I don't even know.”

I'm so tired or I just was so laser-focused on this one thing that my mind isn't even open to what I have to work towards next. It's a very weird phenomenon. I definitely battled some of that and as a result, my first year was just really rough and I really did not like law school for that.

In regards to picking a practice area, I had always had a weird fascination with business but I didn't love math or science. I have a cousin who started businesses starting at the of 12 and now is an entrepreneur. He's a CEO of a very successful video game consulting company in Texas.

That math-science confidence led him to do things in a financial realm and a coding realm at a young age. I didn't have that so I think for me when I was in law school, I was like, “I want to be involved in business but I don't have the confidence to think that I could be leading the tech side or the business side so maybe this is how I can fit into that equation.”

I really just clung to the entrepreneurial aspects of transactional law and that's how I ended up here as well. I think I always wanted to be in business but had impostor syndrome and not enough confidence to think that I could be the main character in it if that makes sense.

Sarah Cottrell: Yeah. It really does because I think that is part of a lot of lawyers’ stories. Many people choose to go to law school or become lawyers in part because it's almost this process of elimination of “things I think I can't do” and I think that can sometimes set people up for that experience, like you said, of maybe even having a stronger experience of impostor syndrome than they might otherwise have.

I'm curious, you mentioned in law school having to go through this grieving process of what it was going to look like versus what it actually looked like, can you talk to me a little bit about how you move through that process and then ultimately made the decision in terms of where you were going next?

I know you talked about the whole experience that we talked about in the podcast a lot of how you can get into a situation where you're just grinding and the thing that you're told to do is go to Biglaw. A lot of lawyers end up there and then are like, “What happened?” Was that your experience or was it something else?

Ashley Carlisle: Oh, it's such a good question and luckily with the time that has passed, I think I've been able to reflect on it a bit but who knows in 10 years if I'm going to be able to understand more of the minutiae of where I was at?

I think I didn't realize, and I'm not sure if people have talked about this on here, I hear a lot of lawyers talk about it, I'm a first-generation lawyer. I come from a family of cowboys and ministers. They're all very educated, they're business people, and what have you but no one had pursued a career in law.

I came in very naive to the fact that I had figured things out or my family had helped me figure things out up to this point to get into law school and so it was going to be the same thing in law school. Especially at the law school I went to, I just felt like because I did not have family in it, I was just operating so far behind everybody else. Who knows if that's true or not?

But that was really just I got there, everyone wasn't as nice as I thought, it was harder than I thought, I felt dumber than ever, and then I just felt like, “How am I ever going to catch up with these people who know everybody, know what to do, know what to wear, and know what to say?”

Luckily, I found other friends who were in the same spot and I think we all clung together. As everyone does, you figure it out but I definitely think all of that combined just put me in a very negative head space where I didn't really believe in myself. That's a time when you really have to dig deep and just focus on what's in front of you.

In regards to ending up in Biglaw, I think when I didn't believe in myself, the only thing I really had left if I'm being honest was my ego and knowing that I'm a hard worker and I could probably grind it out so I did. I grinded it out. I didn't get my Biglaw job, I've mentioned this in other places, I didn't get it through OCI. I basically nicely harassed the firm that I worked at out of law school.

I think they rejected me multiple times. I don't even know how many until finally one time, they were like, “Oh, actually, the timing works. Can you be here tomorrow and can you do this?” It all worked out because I just kept grinding and applying after people would just say, “No, no, no.”

I really didn't have a reason other than I'm very lost but I worked so hard for this. I am interested in my classes. I do like what I'm doing but I do feel like I haven't gotten my footing yet. Maybe with this name and maybe with all the smart people at this organization, I can learn from them and I can find my footing there.

I think that really was my thought process for better or worse. Like I said, I know a lot of people who aren't. Luckily, I liked transactional work. That's not a given for everybody. Luckily, I liked some of the stuff that we learned in law school. But the social aspect of it and a lot of the actual industry aspects of it are really what made it difficult for me to be in a proper mind space and to actually enjoy it.

Sarah Cottrell: Yeah. I think you touched on something that can be so insidious about the legal profession. That is no one is going to say to you, well, I don't know, someone might, but no one is going to say to you in the profession or in law school straight out, “You're a more valuable person if you can get a Biglaw job.”

But the structure of the profession and the way, especially in law schools you are pushed in that direction and this is held out as the thing to which everyone should aspire unless you're really super into public interest or whatever, I think it really does create this sense of “If I can get that type of job, then I have proven my worth in some very fundamental way.”

Especially when you've got a lot of people who were type-A, get the gold stars, all of this stuff who have learned via life experience that achievement is what they do, I think it definitely creates this situation where if there's any confusion or if there's any insecurity, which hello, humans, therefore most people have both confusion and insecurity, it makes the path of getting into Biglaw feel like, “This is the thing that's going to show that I belong here.”

Ashley Carlisle: Yeah. I think it was part of that but like I said, part of it was I just didn't have any confidence in myself and so I really wanted to be around people who I thought understood it all and had it together and maybe I'd figure it out, which I think no one really has it figured out. That's what I learned really quickly being there. But really, I was like, “I got to fight for this because they have it figured out.”

It's not like my family knew anything. My family still to this day has no idea what I did in a law firm or what I do now. I still get random calls, as I'm sure all of us do, from random family members for random things.

Sarah Cottrell: Yes, and you're like, “I do not practice that type of law. Therefore, I am useless to you.” The next question I was going to ask was when you got to the law firm, was it like, “Oh, all these people definitely have it all together and know what they're doing”? Talk to me about your expectations of what it would be like and then the reality of that experience.

Ashley Carlisle: Well, because I got my job in a nonconventional way, I really had no idea what the baseline would be. I had summered at another smaller firm in law school so I knew what a firm situation would be like but I went to a way, way bigger firm that was way busier. I went in being like, “I have no idea what to expect. We're going to figure it out.”

Luckily, now I can say having been at a couple of law firms and having talked to a lot of my peers, I could have ended up in a way worse place. I got very lucky with the people that I worked with and the office I was in.

I had overall a really good experience but I think I wasn't doing myself any favors because I didn't have a plan. I didn't know how to evaluate what was going on around me as to, “Oh, I should do that. I shouldn't do that. This is how I should forge my path.” I think I was so worried about fitting in and following all the rules that I didn't feel like I had a choice in my career or what I was doing.

Looking back, I don't know if that goes to mentorship or if that goes to whatever but if someone had told me, and maybe people tried and I just wasn't absorbing it, you don't have to make everybody like you, you don't have to try to follow this ideal image of what you think we want, really what do you want, is it at this firm, what are you doing, I think really all my Biglaw years, I would have been a better person for myself and a lot happier if I just had thought for myself because I was so worried that everyone was constantly evaluating me and thinking that I wasn't supposed to be there, which in reality, I don't have any evidence to support that.

I don't think they were thinking about me. I think I did my job. They were good with it. I could have had a lot more mental space to actually do things that would have made the process a lot more enjoyable for myself as opposed to just worrying that I was not good enough or that they were going to find something wrong with what I was doing.

Sarah Cottrell: Yeah. To your earlier point, I think one of the big challenges when you're someone who's gone through the entire process of college, law school, taking the bar, and then if you started a law firm, I can remember a very distinct point at which I realized, “Oh, I'm no longer in a place where there are semesters or years where you know okay, this is the start of something new.” It was just like, “Oh, I'm here and I'm basically going to be here for??”

I think that can be disorienting as someone who has gone through this process where there's constantly the next thing that you know you're “supposed to do” to reach that point where you're like, “Oh, there isn't any particular thing I'm supposed to do.”

I think sometimes for those of us who are lawyers, it takes us a long time to realize that. We keep looking for, “But what is the next thing that I'm supposed to do? What is the external authority who's going to tell me what things are supposed to look like, whether what I'm doing is ‘the right thing’?” I think that definitely plays a role in how people can experience that post-law-school early practice time.

Ashley Carlisle: Yeah. I think only recently have I stopped the “Oh, what's the right thing to do next?” When people reach out to me being like, “We have this in common in our careers. I'd love to talk to you,” whatever, I'm sure you hear it a lot but I hear it too of “Well, what is the best next move?” and I'm like, “That's not how we should be operating.”

It's so hard. Like I said, I would have been so much happier and probably grown a lot more if that wasn't my mindset. Now at this point in my life, I'm really focusing so much of my day on making sure my mindset is good but I didn't have any cognizance of that before. Especially as lawyers, I think it's so important because we are so neurotic.

Obviously, I'm hypergeneralizing but the smarter you are, the more anxious you are, a lot of studies have shown so I think mindset is just so important, and if anything, that should be a class in law school. I mean there should be so many classes in law school that we're not given.

Sarah Cottrell: Yeah. I think to the point about anxiety, one of the things that I think lawyers often do in order to try to minimize their anxiety about their career is to hold on to this idea that there is one very distinct set of things that you should be doing in a particular way and if you just figure out those things, then you'll be “safe.”

Believing that there's only one way to do things can make people feel “safe” but then you end up in a situation where you're trying to figure out what that thing is and that creates a lot of anxiety.

The reality is that it also creates a lot of anxiety when lawyers start to see or experience things that suggest that actually maybe there are lots of different options and lots of different ways to think about it, which is one of the many reasons why I talk so much about therapy because I think that there's a degree to which it's almost like a self-protective mechanism.

If I believe there's only one right path and if I believe the world only works, let's say, the way the lawyers at my Biglaw firm think it does, then yeah, that can be really difficult in certain ways, that can be really stressful, but at the same time, at least I know what I'm “supposed to do.”

It can be a bit of a shock to the system to realize like, “Actually, no. I'm an adult with agency and can make any number of choices that would all be acceptable in this situation.” Not every human in the world has the same values, priorities, etc, as this small subset of lawyers. That can be really freeing and it can also be terrifying.

Ashley Carlisle: Both at the same time, I agree, yes. I've experienced both. I've had both sets of feelings.

Sarah Cottrell: Yes. You're like, “This is wonderful and horrible.” Okay, can you talk to me a little bit about how you ended up moving into the role that you're in now? In particular, I have a lot of lawyers reach out to me who are interested in marketing, especially because they see it as being more creative but they also feel like, “I have no experience so there's just no hope for me and all is lost.”

Can you talk a little bit about how you ended up moving into the role you're in now and maybe what observations you might have about those feelings that lawyers may have about making a move like that?

Ashley Carlisle: It's so interesting to me—and obviously I'm here so I guess I should self-analyze—that so many lawyers are so interested in marketing now that I've tried to test the waters here for a little while. I think it is just because I guess it's creativity but it's managed creativity in a way. It's not going off to be an author or a screenwriter. There's still some security and structure to the idea of it.

But still to this day, when I talk to people and they ask those questions, I'm like, “Where does this come from? Why is interest in this area?” For me, I wish I could say it was more planned than it was. I had met Tony Thai, the founder and CEO of HyperDraft.

We were both attorneys at Goodwin Procter and he had been working on HyperDraft as a project I think now for about seven years. It had already been a few years. It was already a product. It was already deployed in some places when I met him. It was just he was still practicing law.

When I talked to him, my main thing wasn't that I wanted to be in marketing. My main thing which I think is so important for anyone who's joining a marketing, coms, or anything that's supporting the business role in that way is I saw the problem he was trying to solve which was the law is not really sustainable and it's increasingly unsustainable, especially Biglaw for people to have a life, to enjoy themselves, and a lot of it really is just like an efficiency for an efficiency.

I saw the problem, I liked that he was building a solution in a way that I felt good about and felt like it actually respected the profession and we're all lawyers so we get it. At that point, I just wanted to be involved.

In regards to the marketing, it was more so just having ideas for him of what I thought the business could do and that just so happened to be in the marketing vein to which when then he was like, “Oh, you should join us in marketing,” I freaked out for a few months and was like, “I can't do this. I'm not qualified. You're a very smart person that knows people. I am not the person for this.” I was trying to convince them, “This is not for me. You should find somebody else.”

But at the end of the day, I think marketing really is understanding the problem, having the guts to try things to tell the story in a different way to stand out, and then having the wherewithal to execute things. I think I had that for his problem set and we just ran with it.

The first year was pretty terrifying and I still feel like I have days where I'm like, “Oh, my gosh. I shouldn't be doing this. I'm still learning,” but one thing that's good and bad is when I've networked with other marketing professionals that even came from a traditional background, they feel the same way.

Marketing is constantly changing so it's good and bad that I feel like I'm not crazy that I'm having those thoughts but also this isn't going to go away anytime soon. This is something that I have to be okay with the fact that marketing is the wild west of things changing quickly and you have to be adaptable. It's not going to be like when I used to have a credit agreement role in my inbox and I knew the standard process of what the next few days would look like. That's not my life in this space.

I think that's something that I really didn't understand coming from such a formulaic background is I thought that once I did my first email campaign or once I did my first marketing strategy deployment, it would be the same every time. It is. You learn how to do it better, you learn how to track it better, you learn how to be quicker with your instincts but it is a lot of ongoing learning and being okay with the fact that you're going to have some fails and you have to wake up the next day and still keep going even if you're embarrassed.

You're going to have some things that do way better than you think, worse than you think, and you still have to be okay with the uncertainty of it all while still maintaining a balance. I think that's something I didn't really realize.

In regards to—sorry if I went off, I'm trying to remember your questions—the how, the creativity experience, I think I've battled with that. Some days I'm like, “Oh, am I really doing a service to everybody by not having a traditional background?” From the beginning, I've taken it upon myself to create my own curriculum, which has been hard because there are many days where I have a long day and I don't want to read another marketing book because, spoiler alert, a lot of them, only 10 pages are actually good and you have to suffer through the rest of it.

I can even list you my favorites and still in that, it's that type of struggle. I really have had to teach myself some things and ask some really dumb questions to people that I'm a little embarrassed to ask but have to just for the benefit of my own learning.

I think the book that actually helped me the most, the name escapes me but I could probably give it to you later, now my husband has all of his direct reports read it. Basically, it talks about that when you're learning something new, you have to go back to an elementary level and if you don't, it completely puts your mind and your process at a disservice.

I think it took me about six months to get to that point where I had to just be really okay with probably being the dumbest person for a while in certain areas that I didn't get naturally to ask just the dumb questions, be okay with the fact that they're going to be like, “Oh, my gosh. This person's an idiot. Can you believe they asked that?” just so that I could create that foundational modeling in my brain.

Because I think in law school, I had this idea of “Well, my value is being smart and being professional so I need to present as always being smart and always being professional.” But that really hampers your ability to learn things that are completely different than you've encountered before.

I would say anyone wanting to go into this from a legal background, having the ability, whether through therapy or just a lot of self-reflection, to see where the ego is and where that is, and remove that, and really be open to being the dumbest person in a room for a while is vitally important or else you'll learn something.

Some things in marketing, I understand very instinctually but when I look at the whole wider picture of what I need to do, there are some things that I just don't get and I really have to take that ground-level approach or else, it's not really serving the bigger picture of what I'm working towards.

Sarah Cottrell: Yeah. That is a perfect example, again, of one of the many reasons why I think it's so crucial for well, everyone, but lawyers who are thinking about doing something else to get into therapy because one of the things, to your point, that we're really made to believe as lawyers is we always need to have the answer, we always need to look like we are completely on top of things, and it is so antithetical to the type of learning and flexibility that you need to be willing to engage in if you're going to make a move to another career.

Even many lawyers, one of the reasons why even if they're extremely unhappy practicing law that they resist making a move is that they will literally say, “I don't want to look like I don't know what I'm doing.” In other words, “I'd rather be miserable but look like I know what I'm doing than be in something that maybe is more fulfilling, is more creative, is more whatever, a better fit but where I would have to be able to set aside some ego”

To be clear, I am not judging you, people who are listening for feeling that way because the reason I’m able to talk about this kind of stuff is because this is stuff that I've experienced as well. Especially in our profession, it's something that you are very much trained to feel like you need to present in a certain way.

To your point, Ashley, so many of us were like the smart kid and what we brought to the table was that we were smart and could always be relied upon to know what was going on and to be one of the smartest people in the room. It's an identity question. It's a question of “Who am I?” which, again, is why it is really helpful to explore this stuff in therapy.

Ashley Carlisle: Yeah, and the identity thing, that is one thing I actually have been telling people and I think people have been surprised, and I don't think it'll be surprising to you, but I think people are just starting this journey of seeing if they want to pivot their experience into something else.

I say pivot because I hate when people say abandon because I truly don't think I'm abandoning, it's just like building off of, but the whole thing is I think I'm going to be in this identity crisis for a while of “Am I still a lawyer?” I get a lot of weird comments from people on that.

We've had conversations about how I could see a future where I go back to practicing law, this was really just a thing that I knew I needed to jump on or I regret it. I was passionate about it. It was not some plan to completely leave the legal profession and protest. I think for some people like me, it's more complicated. I think because non-lawyers don't really get our industry, it's a lot of, “Well, if you aren't doing this, then you're not a lawyer.” That's not true and that's a complicated thing you have to work through all the time.

Then also when you're in business meetings and you're a lawyer, people act towards you differently or sometimes it takes me a little while to get them to relax or to not judge me on certain things. Then lastly, and I don’t know if you talked about this with other guests, a part of me doesn't want to bring it up but I think it's important, as a female—and I'm a White female, I'm sure it's worse for so many different people—but I get the thing of, “Well, you must have failed if you ended up here.”

That always sends me for an ego loop of, “Well, that's not true, but even if it was true, this is your assumption of me?” versus our whole founding team is lawyers, I'm the only girl. When they talk to them—and this is obviously not their fault—but when people talk to them, it's like, “Well, you're such a trailblazer. You're an innovator. So good for you to leave the law and do this thing of building technology to try to digitize these legacy processes.”

They talk to me and they're like, “Well, how did you end up here? Did you fail the last thing?” I'm just like, “So because I'm a woman, there's this weird thing with the identity of being a lawyer that if I'm not following the rules that you want me to be, I can't fit into this paradigm.”

It's a very weird thing that I thought would not be a thing I'm still struggling with and to be honest, and I tell people this, I'm still getting those comments. I thought it would be a year and even my team members still get mad about it. To be honest, I think they're more surprised by it than I am because they don't get it but it's still a thing that I get.

I don't know where that comes from or if other women who have transitioned from law to other things have also experienced that, but that's something that I try to warn people people because I took it personally for the first few months thinking it must have been a me-specific thing.

Obviously, with time, I realized that it's not that and it's some weird social conditioning that's not personal to me. But that was a part of that identity struggle that was super painful because I just had never heard someone going through that if that makes sense.

Sarah Cottrell: Yeah. I think there's a level of structural misogyny that comes into play in these types of situations. To your point, it creates this scenario where you still want to do the thing that you want to do that's the right fit for you but as a human being, having people make unfounded assumptions about you is not going to be pleasant no matter what assumption it is that they're making.

I think it is just another example of when people think about moving into a marketing role, I think they often think about the technical things of “What do I need to show in terms of skills?” and yes, fine, we can talk about those things, but also there are these other factors that often are just as significant in terms of how people feel about making a move, whether they're going to make a move and the experience of it.

I really appreciate you sharing that because I think that is a very common thing that people deal with. Can we circle back quickly to you mentioning all the facts that marketing is so often just trying things?

I know for the listeners, Ashley was on a panel that I hosted inside the Collab with a bunch of different lawyers who are in different types of marketing roles and this is one of the things that we talked about on the panel because it's something that's so different from the typical experience of being a lawyer with marketing, and I have learned this as well running Former Lawyer, so much of it is, on some level, trying things and seeing if they work, and then knowing that some number of things are not going to work and you're going to learn from that, tweak, and adjust.

It is such a different mindset from lawyering. Can you talk about that, Ashley, a little bit, the difference there and adjusting to that, and for someone who's thinking about moving in the direction of marketing, what they might want to think about?

Ashley Carlisle: Totally. I think when I got into this role, I did think it was going to be more of the strategy and creative behind it. I think that's what most people envision. That is a part of it but to be honest, once you get to a high level or a scalable business, a lot of that, I'm looking to agencies to do. That is I need to manage it, make sure it stays into the brand guidelines and the brand voice and where we're going as we're looking towards the future but that is not a typical marketing job, that is a creative job that's associated like you’d be working with those people.

I think the two main things that were like “Oh, this is different” in my experience was because you are testing so many different things, the amount of organization and tracking that you need is a lot. I know that sounds dumb and when someone told me that, I was like, “Well, I'm a corporate attorney. I am organized,” and I am, but it is a standing-up standard process. It's like a closing checklist times five of every day of making sure that all of the different things are recorded, tracked, and communicated in a way that the person you're communicating to understands because that is how your performance is reviewed versus the billable hour.

If you don't do that, you're doing a detriment to yourself, first and foremost, and how they can evaluate your performance but also just how you can figure out what's working and not. The other thing in marketing, which I think lawyers struggle with and as I talked to lawyers who are interested, it is a thing, the overthinking is not a thing that the marketing timeline allows. You just got to go sometimes even if it's terrible.

I still struggle with that of shipping things that I'm like, “Oh, my gosh. I need three more days on this,” but you just have to let it go and iterate as you come and be okay with the fact that people might not like it or you might not like it or what have you, and be okay and the fact that you know tomorrow you can build upon that, that's something I still struggle with.

Some days I wake up and I look at all our stuff and I'm like, “Oh, my gosh, I could be doing a way better job on 20 things,” but at the end of the day, I have to think of the top three goals that I'm supposed to be hitting. Even if the rest of it doesn't look like I like, as long as those top three goals are okay, that is my job.

The management, the organization, and the not overthinking to your detriment, coming from a legal background, is still something that I'm trying to reprogram in myself but I think it's something I also didn't really expect.

Sarah Cottrell: I was going to ask if there are particular qualities, skills, or strengths that you think either are really important for someone who's thinking about trying to pursue a marketing role or conversely are like, “If this is a huge characteristic of yours, maybe not a great fit.”

Ashley Carlisle: Oh, that's hard. I feel like it's so open-ended and there are so many different types of marketing and different companies. I guess the two things I always look for are communication but it's a different context than what a traditional legal background would have.

For example, and I think I mentioned this in the panel, I learned the first week how I say things to my CEO and how I need to say things in marketing copy versus vendors or agencies I'm working with, it's a different story to each of those people. If I were to use the same explanation for each of those, none of those are going to work. It is definitely being more thoughtful in how you're communicating on an every communication basis, which eventually you just learn how to do.

But as a lawyer, I don't know, when I was in a contract or drafting, I thought about it carefully but in correspondence, I didn't really have to. Everyone's on the same page, I didn't really have that, so saying things very meaningfully and then knowing that you have to talk to different people in different ways and testing that within yourself is something that I think took me a while and I see people struggle with.

The other thing is rejection and perseverance, which sounds dumb because lawyers have both of those things, but like you mentioned, being okay with the fact that for periods of time, you're going to feel so dumb because this thing you worked for six months for didn't work how you thought. But you still have to wake up the next day and either do it again and differently or find a way to fix it and realize that no one's really thinking about you as much as you think they are.

I think I got this weird sense of because of how things are handled in a law firm of if I mess up signature pages, I'm definitely going to hear from one or two people about how bad that is and it'll get blown up into a thing, whatever. I think because of that, every time I make a mistake, I'm like, “Oh, my gosh, well, I feel like I need to apologize and they're probably going to yell at me,” and blah-blah-blah.

In business, especially in marketing, it's more so what's the next move and how quickly you can rebound from that unless you really messed up. If it goes into a crisis situation, that's a whole different thing. But I think that's something that I'm still working on, not over-indexing on when things don't work out and being okay with “Okay, I got to move on to the next thing,” because I think in law school and in law firms, we’re just admonished to an extent to be in timeout for a while even if we don't realize it. So getting out of that mindset is important.

In regards to personality types that are good or bad, I think you really have to be, it's not even creative, creative is icing on the cake but the ability not to follow everybody else but to actually think thoughtfully about why you're doing something even if it doesn't look from the outside if it makes sense is paramount.

I use this example all the time, we all work at law firms and we see the law firm marketing on the law firm websites, they all look alike. All of them look alike. They all do the same things but then they're always struggling to figure out how to bring in new business. That's because they're more concerned about all looking like each other and all keeping up as opposed to figuring out what they could do differently to get new business.

When you're in the business world, the law firm marketing thing, that doesn't work. You can't take those values and apply it or else, you're not going to be getting the customers you need, the brand recognition you need. You have to be able to, even if it looks rough from the outside or you're embarrassed, be really focused on intentionally being like, “Okay, I'm not following the trend to follow the trend because it's the ‘best path forward.’ I'm thinking why I'm doing this and how it's going to bring me where I am even if people think I'm crazy.”

I think that's something that, like you said, we as lawyers are looking for the thing that they should do, that is something that's really hard to program someone for and make that the first instinct.

Sarah Cottrell: Yeah. Speaking as someone who has had to teach themselves everything about marketing in the last couple of years, I think that it can be a very big challenge if you're someone who really likes to know, “But what should I do? What's the right answer?”

Okay, Ashley, is there anything else that you think people should know about marketing if they're thinking about going in that direction or about your experience thus far?

Ashley Carlisle: It's an open-ended question. I'll try to keep it short. I would say if you're really at a crossroads thinking about it, try leaning into personal branding first to see where you naturally have skill sets if that makes sense. I was not active on LinkedIn until this job and I'm still not that active, but try thinking of what your personal brand is as a lawyer and thinking about how you would market yourself.

Through that exercise, you can see, “Oh, I'm really good at branding. I understand the visuals, the tone, and everything. Or I'm really good at thinking of strategies to get people to see my name in traditional marketing stuff. Or I can think of newsletter options.”

You naturally will see where your brain is going and then read a couple of books and see the web of all the different pots of marketing to see, “Okay, I'm good at this, I'm not good at that.” I think that is a common thing that I have when people talk to me is they're just like, “Oh, marketing generally,” and I'm like, “Well, just like litigation versus transactional, there are many different ways to fit into this marketing spectrum.”

If you don't already come with that, which I didn't, you just have to learn the hard way and luckily, in my role where I have to wear all the hats, I can do that. But in many contexts, you're not really looking at the right jobs or marketing yourself for the right jobs if you don't instinctually know what direction of buckets you're heading into because there are so many things that fall under the marketing umbrella.

Another thing is a lot of lawyers I talk to, which I totally get, it is a big jump, you don't have experience, often people aren't going to want to pay you what you were paid previously, people aren't going to understand your experience at a law firm so being willing to take a pay cut, take a title cut, take some either side jobs or a new job and just really be willing to transition and be okay with not making a lot of money for a while makes things a lot easier.

Then also just constantly producing, that's still something that I try to work on with our team is in marketing, you have to produce something almost every day. Sarah, you put a lot of content out there, that's something you have to build up a muscle of “How can I constantly keep moving on this even if it's not something I'd be happy with?”

I think those are the things when I talk to people or when they come with me with questions, those are the three main things that I'm like, “I think those would be good places to start because if you are okay with the pressure of having to produce and you naturally can find ways to keep yourself disciplined, you can find instinctually where you are on the spectrum and then you've seen if you like just the introductory stuff, from that, you have a lot of information to figure out if you want to be a content writer, a brand marketer, or a customer acquisition marketer, an email marketer.”

You have a lot more information without you having to just sit and be like, “I'm good at this.” It's a way to experiment in an easy way that only takes a couple of hours to figure out helpful information so that this process doesn't seem as daunting.

Sarah Cottrell: I think that's so helpful. Okay, Ashley, if people want to connect with you, where can they find you online?

Ashley Carlisle: Sure. I am Ashley Carlisle on LinkedIn. Our HyperDraft website is hyperdraft.ai. We're also HyperDraft Inc. on all socials for the most part. If people have questions just targeted specifically towards me, they can reach me at my email. It's [email protected].

Sarah Cottrell: Amazing. Ashley, thank you so much for coming on and sharing about all of this. I know it's going to be really, really helpful for so many people.

Ashley Carlisle: Well, thank you for doing this. I know it's a lot of work but I know a lot of people have gotten a lot of value in the content you put out there so I appreciate you and all your hard work.

Sarah Cottrell: Thanks so much for listening. I absolutely love getting to share this podcast with you. If you haven't yet, I invite you to download my free guide: First Steps to Leaving the Law at formerlawyer.com/first. Until next time, have a great week.