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.

This week, I'm sharing my conversation with Lynley Ogilvie. Lynley left the law to become a landscape designer. She's the first former lawyer turned landscape designer that I've had on the podcast, and I'm really excited for you to hear this conversation. Let's get right to my conversation with Lynley.

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.

Hi Lindley, welcome to The Former Lawyer Podcast.

Lynley Ogilvie: Thank you, Sarah.

Sarah Cottrell: To get started, let's have you introduce yourself and then we'll dive right in.

Lynley Ogilvie: Sure. My name is Lynley Ogilvie. I live just outside of Washington, DC. I grew up in West Virginia, went to college at Harvard, went to law school at UVA, and settled outside of DC, and have lived here ever since.

I’m married. I have two kids who are young adults and two corgis. So that's me. What you're probably going to ask me more about is what do I do now. I'm a landscape designer with my own firm.

Sarah Cottrell: Yes, which I think is so interesting. Actually, a listener of the podcast ran across your information and emailed me and said, "Hey, this is really cool. This might be a cool person to have on the podcast." So that's how we connected, and I'm super excited to hear more about that story.

Of course, on the podcast, we always start in the same place, which is back at the beginning. You're a landscape designer now, but you once were a lawyer. What made you decide to go to law school?

Lynley Ogilvie: So back in college, and even in high school, I had been very interested in art. I did a lot of graphic art. I worked as a graphic designer for a small advertising agency. I majored in East Asian art history. When it came to senior year, I started looking for jobs, either in advertising as a graphic artist or in some other related fields and really couldn't find anything.

I ended up graduating and moving to the DC area and pounded the pavement looking for a job for a few months and ended up working on Capitol Hill, which is very common for young people in DC. I worked there for four years and enjoyed it.

I don't think it was my passion, but I found the work interesting, the people were terrific, and most of the people I met were lawyers. So I kept hearing about, "Oh, you should go to law school." This is a great way to climb the ranks in Washington. I think the statistic is something like one out of every five residents of DC, maybe it’s even higher than that as an attorney. It's kind of hard to avoid us in this area.

Anyway, since I hadn't had any luck finding anything in art, I thought, “Well, I'll make that my hobby, and I'll go to law school,” because I had really run through the ladder of progression in my job on the hill and was looking to find a credential that would help me advance.

I also think between you and me, Sarah, I was feeling unfulfilled and thought that law school might create more opportunity for me to look in different areas. So I went to law school and ended up doing a summer clerkship for a law firm in DC, which is the firm that I went to after I graduated.

Sarah Cottrell: It's so interesting because for many people, it's such a common part of the story for law school, it becomes this next step in the sense of, “Oh, this makes sense, either someone graduating with a liberal arts degree and they're not exactly sure what they want to do or something where there's an idea about what doors might be open by the law degree.”

I'm curious, by the time you decided to go to law school, knowing that you were interested in art and were setting it to the side to be a hobby, was your idea like, "I'm going to go to law school and this is going to be my thing. Being a lawyer is going to be the thing for me,” or was it more of, “This is just the next step that makes sense and I'm not necessarily expecting to love every moment”? Does that make sense?

Lynley Ogilvie: Absolutely. I think that's exactly the right question. I wish I had had that self-awareness at that age because definitely, my answer is it was the latter. It was another rung on a comfortable ladder.

I say this to people who ask me, young people who ask me about law all the time. I say, “It's not for everyone. It is not what our parents used to tell us, at least in my generation, was you can do anything with a law degree. You can do certain things with a law degree and there are a lot of things, but not art.”

Sarah Cottrell: Yes, I tell people, people with law degrees do basically all sorts of things, that doesn't necessarily mean that “you can do anything with a law degree” is really a fair way to describe it.

I think it's such a common experience for people who go to law school expecting it to open a bunch of different doors. They come to realize yes, it opens some doors, but not necessarily as many as I think might be implied by the whole “you can do anything with a law degree” idea, which is still pretty commonly said, and people still seem to take it as accurate.

Lynley Ogilvie: Yeah, I agree. The other thing that law school doesn't do is expose you to other things that you might like to do. In fact, it's pretty narrowing in that respect because all the opportunities, especially once you start taking on debt, are in law fields.

So someone who goes into law school like I did with the thought that the world is their oyster when they graduate, that they will magically know what to do next, I don't think that's the best approach. I think it'd be better to take more time, maybe exploring other interests and really figuring that out before going back to school.

Sarah Cottrell: I think that is such a good insight. I mean that is something that comes up with the lawyers that I work with all the time, which is there's this question of what is it that you actually want to do? I think many of us who became lawyers chose to go to law school as kind of an end run around answering that question.

So then we sort of come out on the other side and we’re lawyers, but that question really hasn't been answered. It's like, “Well, I'm a lawyer, but I still don't necessarily know what it is that I want to do.” So can you talk a little bit about your experience? So you graduate from law school and you go to the law firm, how was that for you?

Lynley Ogilvie: It was brutal. Yeah. I'll be honest, I'm sure that a lot of people who listen to your podcast have had this experience. It's a very intense experience.

Sarah Cottrell: Yes, yes, for sure. We talk a lot on the podcast about the experience, especially of working in law firms and how inhumane it can be. I'm interested to know, when you started, well, talk to me a little bit about the trajectory. At what point did you go from “I don't love every moment of this/This is pretty brutal” to like, “Hey, maybe I don't actually want to be lawyering anymore.” Were there multiple steps? Talk to me about that process.

Lynley Ogilvie: Yeah. I mean, I think I felt probably from even when I was in law school that I was not going to spend my career in law. I wanted to figure out what else I would do. But once I joined a firm, I had no time to figure it out.

Sarah Cottrell: Yes. Yes, totally.

Lynley Ogilvie: You think the world is an oyster, but you have no time to explore it, so you just keep doing what you do. I think that feeling increased every year I was there. I mean, stepping back to the conversation we were just having about why people do this, I mean, there's a certain kind of person, and I think a lot of us end up going to law firms, who are very good at checking boxes and completing checklists.

We're organized. We're intelligent. We're methodical. We're capable. So yes, we can absolutely do the job, but in our heart of hearts, it might not be what we truly want to be doing and what we love.

I was so busy checking those boxes and being organized and methodical that I had no time to think creatively. I had a great reputation in my law firm. I really liked my colleagues and clients, all wonderful people. It's just that I didn't want to spend all of my life doing the work of being a lawyer. So billing 2,500, 2,600, 2,700 hours a year, there's no time left to think about anything else.

Then there are the golden handcuffs. I'm sure you've talked a lot about that too. It's a great salary, especially if you're working that many hours, and the firm is very enthusiastic because they love having associates who can make clients happy, work long hours, and really throw themselves into the work.

This tension started to bubble over for me after I closed a huge deal that I worked on. I did not close it alone. It was a big project that my firm had taken on and I started working on it almost as soon as I arrived and worked on it for five years. When we finished that deal, I was a mess. I was just exhausted. I had been taking taxis home to my husband at two and three in the morning for a year.

After we closed, I was sort of lying on the couch thinking, "There's got to be more to life than this." I did want to have children, but I don't know how that would happen. That's when I started really trying to look at what I wanted.

I spoke with a couple of headhunters and interviewed for in-house jobs, but it was always the same issue. I was just going to get paid less to do the same kind of work. I actually saw for about a year a therapist who was a retired attorney who counseled lawyers who wanted to make transitions.

That was very helpful to me because I couldn't even articulate, I was so exhausted and so caught up in all of this that I couldn't articulate why I wanted to leave and how I might handle that with family, friends, and colleagues.

It was a process. Then I got pretty serious about starting a family. When I got pregnant, probably a lot of people thought, “This is the time where I have to make a decision.” After I had been at the firm for six years and got pregnant, I was out on maternity leave for three months and decided to not go back. I went to work in-house part-time for a client of the firm.

Sarah Cottrell: I'm curious because I know, and we talk about this in the podcast all the time, but for people who are thinking about leaving law to do something else, you mentioned one of the things that you had to work through was how to deal with that with the people in your life. Because so much of being a lawyer becomes wrapped up in our identity.

I'm wondering for you, how did you work through that particular process? Because it's something that basically every lawyer who thinks about potentially doing something else eventually has to work through.

Lynley Ogilvie: Yeah, it's very tough. People seem to be so vested in that self-image, and I was definitely caught up in it. I liked the respect that just saying I was a lawyer would confer on me. My family had always been supportive of the decision to go to law school, and they just saw me as a lawyer.

But they also saw what was happening to me physically and emotionally. I think they wanted me to have a better life. Then with my colleagues, it was a very hard thing to discuss because I think lots of people share the interest, but they have, for whatever reasons and through whatever mechanisms, not made that decision to leave. So I just had to at some point stop talking about it with colleagues and figure it out on my own and with my family.

Sarah Cottrell: Yeah, that makes a lot of sense. I remember, and I know this is a very common experience, but I can remember feeling like, "This is really bad, and I do not want to be doing this," and then having conversations with peers, colleagues who are peers, and they shared the feeling, and yet we were coming to very different conclusions, and it felt a little bit like, "Okay, but you think this is really not good."

There was just this kind of I relate a lot to that idea of being very disorienting to seemingly have the same sort of view on how good or bad the situation was for you as a person, and yet, some people just have very different approaches.

I think because there is that identity piece, it is so easy, as someone who's thinking about going to do something else, to feel like, “Well, there must be something wrong with me, because this person basically sees the same things, experiences the same things, but is coming to a different conclusion.”

I know that's something that so many people who've come on the podcast have talked about having to resolve that sense of like, "Is there something wrong with me because I don't want to continue doing this?"

Okay, so tell me what happened next. You went out on maternity leave and then you went into an in-house role. What was next?

Lynley Ogilvie: I worked in-house for even longer than I had worked in the firm. I was busy having kids. I have two kids and I worked part-time the entire time that I worked for the corporation where I worked.

I was associate general counsel. I really enjoyed my colleagues at the corporation. I liked the variety of legal issues that came before me. Back in the law firm, I had been a project finance lawyer working on mainly energy projects in the developing world and I went to a communications firm, PR and communications, and their legal questions were completely different and varied, everything from foreign practices act to advertising to petty theft. We had to deal with it all.

That part of it I enjoyed, but it also helped that it was only a few days a week and I could focus on other parts of my life, including my family, and then getting back into some of my hobbies, including gardening.

I was there for nine years, and it all kind of came to a head when the legal department was overwhelmed with work and needed to do some restructuring. I'm not going to go into the details, but it became pretty clear to me that this was the point at which I needed to decide whether I was going to stay or make a change.

I wasn't going to make a change and I didn't want to go make a change and go to another corporation. It was going to be a career change. I was driving home from work one day and thinking to myself, “If I don't do this, I'm never going to make the shift.”

I already knew what I wanted to do. I had been taking classes in landscape design in a local program and loved it. I had been talking about making that transition for probably three or four years before I finally did.

I came home that evening and I said to my husband, “I think I really want to do this, can we afford it? How do you feel about it?” I'm really fortunate to have a great spouse who's been with me since the beginning of this journey. He knew how much I wanted a change and said, “Yeah, we can make this work.”

I told the corporation that I would be leaving in six months, that I would help them find my successor, that I would train that person, and that I was leaving to start a landscape design business. I almost immediately got four clients out of the people I worked with as a lawyer. Then my friends at the law firm started asking me to work with them. It wasn't long after I left that I was pretty busy as a landscaper.

Sarah Cottrell: I was going to ask, in terms of how people responded, you laughed when you said, “I'm leaving to do this other thing,” and I assume that's in part because there were people who were surprised by it. It sounds like the people closest to you weren't surprised by it, but were there other people who were surprised?

Lynley Ogilvie: Oh, I think most people were floored. Yeah, I mean they just see you one way. I'm the lawyer who likes to garden. I'm not going to switch hats, am I? No, but yeah, and I had a great relationship with my colleagues at the corporation, and they really liked and depended on me. I think they were very surprised but excited, which was nice.

Sarah Cottrell: That is nice. One of the things that comes up a lot for people as they think about what it is that they want to do is for people who have a hobby that they're very interested in, often people will think about, “Is this something that I want to do professionally? Is this something that I want to do full-time?”

It's a pretty complex question because there's a big difference between doing something that's a hobby and having it be the thing that you do as your job. I'm wondering for you, how did you work through that process of deciding, “This is something that I enjoy and it's also something that I want to make my work”?

Lynley Ogilvie: As I said, I was taking classes, I knew I loved the subject matter. One day, about three years before I stopped being a lawyer, I saw an article about someone who had made a major change. The question that he had asked himself was, "What would I do if I promised to follow my energy?"

I just found that very inspiring because it was so clear to me that I would happily stay up all night working on a landscape plan and it was such a slog to work beyond office hours as a lawyer.

That was very clarifying. There was just so much energy for me. Some people call it a passion. It was clear that this subject matter was very interesting to me and gratifying to me. It's good to know that.

It's quite another to actually make the transition. I think like lots of lawyers, I'm pretty risk-averse. I had a family, just in some ways, I'm still amazed to this day that I've made the leap. I think it all came to, as I said, a head because I was forced to make a decision about whether I wanted to continue or leave and I just had an epiphany on my drive home that it's now or never. I need to do it.

I had the training, I did not have the structure but that's what lawyers are great at. We have such good skills in creating structures and systems. That part of making the transition was not hard and I did a good job at it.

Sarah Cottrell: What do you think was the hardest part of the transition?

Lynley Ogilvie: Probably the hardest part beyond just taking the leap into the unknown was deciding how to take work, how much work I should take that was not high-profile, I'm not sure what word to use. Let me just say that I got down in the dirt for a couple of years.

You wouldn't have recognized me. One day I was wearing my suit, going to law firm, very professional, no dirt under my fingernails, and then a year later, I'm working with people, the vast majority of people I work with on crews do not even have high school educations.

I'm covered in dirt. I'm taking my lunch in Tupperware. It's a very different life. There was a lot of humility in the first couple of years. I think that I actually really enjoyed it. I love the people I work with. I'm not as much in the mud as I used to be because I have people who help me with that. But that was a big change.

Sarah Cottrell: Yeah, I think it is a big change, especially, I don't know if this was your experience, but I know this is the experience of a lot of people who become lawyers, they often either were the kid who was really good at school or maybe even became from a family where school and being smart was really valued and a very specific set of skills and traits are held up as “These are the ones that ultimately lead to things like wearing a suit and going to a law firm.”

I think one of the things that is such a huge part of the experience of really figuring out what you want to do and where you want to go is letting go of some of those ideas of “This is the pinnacle, this is the only pinnacle of what you could be doing.”

I think in some cases, there can be a devaluing of other types of work, of other ways of working, other ways of valuing certain types of pursuits, more intellectual pursuits versus others, and I have found for myself and also for my clients that really dealing with that, understanding that, and seeing it for a little bit of the false construct that it is, is very important and helpful when you're genuinely trying to figure out “What is it that I want to be doing?” Because holding on to some of that can keep you from making a move like the one that you're talking about where you were very happy and it was such a good fit and it was just so different.

Lynley Ogilvie: Yeah, you said it beautifully. Exactly right. The whole thing.

Sarah Cottrell: Well, and this is why on this podcast, pretty much every episode I'm like, “And by the way, if you haven't seen a therapist, you should see a therapist because every lawyer should see a therapist,” but also there are some of the these really deep-seated questions and ideas that come up when you're thinking about making a career change like this that a therapist can help you with. So for everyone listening, this is my weekly plug for therapy.

Lynley Ogilvie: Absolutely.

Sarah Cottrell: Okay, so Lynley, can you talk a little bit about just the process of creating your own business, growing the business, where you are now, how long it has been since you started the business? Tell us a little bit about where you are today and how you got there.

Lynley Ogilvie: Yeah, great. Now, this is the fun part of the story. I love what I do. I love my life. I went back to a retirement party for the partner I'd done most of my work for, and I looked around the room and I was like, "Oh my God, I'm so happy I left." Because I really love what I do.

When I started, I formed a corporation. I basically just tried to get the word out. I took almost anyone who asked me for help. I joined a couple of local associations that are groups of people in the landscaping industry and that's been extremely helpful both in terms of getting information and making friends because I'm a solo practitioner so I no longer have a firm of people who greet me when I walk in the door every morning. It's me walking into my home office.

The build-up probably took about three or four years to the point where I felt like I was working as many hours as I had been when I was working part-time as a corporate counsel, which was fine because I still had really little kids, not really little, like 11, 12 at that point.

Then I got a lot of my work by word of mouth from lawyers. Turns out a lot of my clients are lawyers, and it's actually been very helpful that I understand their lives and how to communicate with them and have the confidence to communicate with them and negotiate with them.

I really hit my stride probably about three years ago, as did most people in the landscaping business. Because of the pandemic, everybody was looking for ways to enhance their outdoor space, and I had been doing this long enough that I could really meet the challenge and I have grown my business significantly.

I now also have a maintenance company that I split with another designer. So we have two businesses. I don't have any employees in my landscape design business, but I have staff in our landscape maintenance company.

For landscape design, I do the design and then I bring in contractors who I work with over and over again to do everything from hardscaping to planting to lighting, fencing, and so on.

That works really well for me because I don't have them on my books. I charge a project management fee once we start the installation phase. Then hopefully, the client hires us to do the ongoing maintenance so I can make sure that the garden continues to look great and I have recurring revenue from that.

I pretty much specialize in doing residential gardens for people who want to use more native plants and create opportunities for them to enjoy nature in their own gardens.

Sarah Cottrell: I love that, among other things in your story, in a lot of ways, it seems it's a return to the things that you were interested in the first place, the artistic piece of things. It's so common, I think, that for many of us who went to law school, there was maybe something else we thought about doing and for various reasons didn't go down that path.

Ultimately, many people find that something that is more in that vein to that thing that they enjoyed when they were younger is the key to or a part of the thing that they ultimately end up identifying as something that's going to be a good fit for them.

I also really appreciated, and this is something that I think is so important for people to hear, what you said about growing the business to the point where you were working at the same level that you had been at the job previously because sometimes when people think about opening a business for themselves, I feel like it can sometimes create this illusion that you can open a business and then you're good.

Basically, it's running full tilt, and I know there's a statistic out there somewhere that typically it takes at least three years for the vast majority of businesses to get to a level of profitability. So just for people who are thinking about potentially going in that direction, I think it's just really important to have all of the information about the realistic experience of being a business owner.

Lynley Ogilvie: Absolutely. I would say now, I've been doing this for going into my 13th year and I work all the time and that's okay because I love it. I'm doing it for myself. I'm not doing it for someone else. I mean, I'm ultimately serving my wonderful clients, but I take such satisfaction from my job that I don't mind working all the time. In fact, I want to.

Sarah Cottrell: Can you talk a little bit about the major buckets of what you're spending your time doing? If someone thinks about, “Oh, this sounds interesting. I like gardening or I've thought about landscape design,” I’m wondering if you could give an idea of what your day-to-day is like, if that makes sense.

Lynley Ogilvie: Yeah, it does. I'll just give you a brief review of the process. I will get an inquiry from someone who's interested. I follow up by telling them how I work to make sure that fits what they are interested in getting because I don't do design only. I only will design projects that I can supervise the installation on.

I meet with them, collect lots of information about how they use the space, what they're looking to do, what problems they need to fix, what their personal taste is, what the house looks like. Then I work through a series of meetings and materials that I provide to them. I work through a design.

We have a draft that gets refined and finalized. That's a scaled plan for how that garden is going to be changed. Everything from hardscaping to planting, to fencing, irrigation, lighting, etc. Then I write a very detailed scope of work and bring in contractors.

Again, these are all people who work with me on a pretty regular basis and I ask for proposals, which I take to the client and I review with the client as I view myself as the client's advocate, not the representative of the contractor, and help them pick what I think is the best fit for their project. Then I supervise the installation.

Everything I just described is sort of desk work. I'm meeting with them on site, the clients on-site, but most of this that I just described is sitting at a drafting table or putting together files on computer that I send to them.

Once we get to the installation phase, my contractors are there doing the installation and it can last anywhere from a few days to several months. I'm usually on site at some point every day and I'm working with the contractor and the crew to make sure that everything is done to the standard that I require.

In that way, I'm representing the client. I go to the nursery to pick out plants. Sometimes I have them brought in from out of state, have them delivered. I site the plants, I put everything out myself, and then work with the contractor to get it installed. That second part of every project is very hands-on.

Because I'm working on multiple projects at the same time, in any day, I might be at my desk for a few hours and at three or four different sites working with crews. It's nothing like my life as a lawyer where I was pretty much sitting at a desk and on a phone all the time.

Sarah Cottrell: Yeah, which I think is something that is very appealing to many people because many people will come to me and one of the reasons they’re thinking about doing something else is that that piece of lawyering is one that is not a good fit for them.

Okay, Lynley, as we're getting to the end of our conversation, is there anything that you would like to share that we haven't talked about yet?

Lynley Ogilvie: I'm sure that you spread the gospel in every podcast, but I would really encourage people to have confidence in their ability to survive and thrive in something different. It's very hard to see that.

It's hard to even make time to think about it when you're working as a lawyer sometimes. But I am so grateful that I did, and every part of my legal practice experience has helped me in my new career. Maybe not in ways that are obvious, but just in terms of intangibles like confidence and organization ability, ability to discern the truth of a situation, the ability to assess clients.

There's just so much of being a lawyer that is relevant and useful, but I am very happy that I made the transition if only because I'm not sitting at a desk all day.

Sarah Cottrell: I love that, I love that so much. Okay, Lynley, if people would like to connect with you, where can they find you online?

Lynley Ogilvie: It's just my name. My website is www.lynleyogilvie.com, and that's my professional site, and my email is in there.

Sarah Cottrell: Perfect, and we'll link that for listeners in the show notes and the blog posts so you can always just go there to grab the link. Thank you so much, Lynley. This was so interesting and I really appreciate you coming on and sharing your story.

Lynley Ogilvie: My pleasure. Thanks for asking, Sarah.

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.