From Biglaw to Running a Creative Business with Loly Orozco [TFLP 086]

Loly Orozco is a former financial restructuring lawyer who went from Biglaw to running a creative business. Her stationery design company, Little Postage House, sells curated vintage postage stamps and designs and prints all types of paper items from birth announcements to wedding invitations to save the dates. 

On this episode of the podcast, Loly shares how she took something that she loved, creating art, and ultimately determined that making it a business was a great fit for her.

The “Weirdo” That Always Wanted To Go To Law School

Unlike many of my guests, Loly grew up wanting to be a lawyer and knowing she wanted to go to law school one day. 

It wasn’t until she was at law school that she realized she was different than those around her – whereas they tended to have liked English classes and stated they were bad at math or science, Loly liked math and science, and art, and didn’t really love English. 

Loly questioned why she felt naturally called to be a lawyer, after all there were no lawyers in her family. She attributes it to the fact that both of her parents were immigrants and from a young age she would adjudicate for them. She would represent them on the phone, with the cable company, in day to day life, and became comfortable with the idea of representing others. 

It Was Easier To Go Into Biglaw

Loly wasn’t sure what area of law she wanted to practice, after all she just knew there were “lawyers” and “non-lawyers”. 

She thought criminal law may be her area and after 1L she did what most people do. Loly went through OCI and tried to land an internship that could lead to becoming an associate. 

It was easier to follow this “biglaw machine” that really makes young lawyers feel like if they miss this boat, they are in trouble, they will be perceived as having something wrong with them. It’s easier to flow with the stream.

“Into” It

Loly was always very “into” law school and the firms she worked at. In school she was very involved; she was on moot court, was on journal, participated in the clinics, gave tours to prospective students – you name it, she did it. 

At her firms, she pursued every case she could get, worked late hours, belonged to different organizations and groups, and was in it to do well. 

She was caught up in law firm life, unlike many who get there and realize right away that they hate it, she was into it and doubled down on it. 

Financial Restructuring 

During a summer at a firm, Loly was able to pick the area she wanted to try out and she learned about financial restructuring law, which is essentially corporate bankruptcy.

She loved that it seemed fast-paced and had a foot in both the litigation and the transactional worlds. She doubled down and began working for a law firm after graduating in a very lean department, one that was male-dominated-she was often the only woman in the room. But she was laser-focused on doing well in this area. 

A Clerkship Changed It All

The law firm Loly worked at after she graduated encouraged people to clerk for bankruptcy courts and there happened to be an opportunity in the Southern District to work with a bankruptcy judge. Her partners sat her down and suggested she get that experience, backing her all the way. 

Loly had had an interest in clerking, but it also intimidated her. She was used to working in a big department, working together as a team to brainstorm, and the high energy of it all. 

In the end, Loly decided to leave the fast-paced environment – after talking it over with colleagues who agreed the experience would be great for her, but that a quick-paced atmosphere is what she needed – and began her work as a clerk. 

It turned out she loved it. She was able to spend time on things, actually think about them, and got to write decisions for her judge, who was a very great teacher and mentor. 

In addition, with this job came another perk – more time. 

Getting To Know Herself Again

With this time on her hands, Loly started exploring and getting to know a side of herself that she had put away for a long time. 

She started drawing, she started pursuing art and other things that she loved growing up that she didn’t have the time to do when she was pursuing law school and doing well at her law firm. 

Loly began to “re-know” herself with this time and realized she actually was really happy and could be happy not being a biglaw lawyer.

Little Postage House Is Born

During this stage of reconnecting with her interests and having more time on her hands, Loly started her business.

She began by doing vintage postage curation for weddings. Essentially helped couples find stamps that match the aesthetic of their stationary.

Loly also started designing and printing invitations for people, which led to sales. So many sales, in fact, that Loly was staying up until 4 or 5 in the morning to complete her own business’ work.  

Getting Off The Hamster Wheel

Although Loly began her business while at her clerkship, it was coming to an end and she realized she didn’t want to go back to the law firm. She wasn’t looking forward to what it would mean for her and her life – her weekends, her evenings, her personal time. 

She talked it over with her husband, her friends and would say that she felt like when she was at the law firm, she was on a hamster wheel. She had been on this wheel that you don’t really know why you’re on it, where you are going, you’re just on it and you’re spinning. 

Loly’s clerkship was her stepping off the hamster wheel and the idea of getting back on seemed incredibly difficult. She didn’t want to do it. She was afraid that once she got back on, once she went back to the law firm, she would forget that she really did love having a life and would root herself into the firm again. 

But, she did return. And it was really hard for her to get back into it and to give herself completely to their practice. She was unhappy but tried to get into it again, she joined organizations, gave it her all, but she struggled to take it seriously. 

Loly was beginning to come to accept that biglaw wasn’t for her. 

It’s Hard To Abandon Biglaw

Even though Loly was unhappy back at her firm, the thought of abandoning the law after she had invested so much time and effort into becoming a lawyer seemed like something that she wasn’t going to do. 

Loly was really enjoying her artistic side and the business she was running. She really didn’t think about it seriously as something that she could do professionally or as an alternative. 

Many lawyers face this situation, one where they want to find more balance, want to be a lawyer in a different sense, maybe as a teacher. But they fight what they think others will think. That they couldn’t “hack” it, that they are a quitter. Loly was fighting this as she vacillated between her law and artistic sides. 

Going Full-Time From Biglaw To Running A Creative Business

During this time, Loly received a call from her former judge, letting her know there was a once in a lifetime case he is recommending her for. It worked out and Loly left the firm to clerk for the second time. 

During that second clerkship that she realized, and accepted, that she didn’t want to find another law job after the clerkship. She just wanted to dedicate herself to doing her passion outside of the law.

So when Loly’s husband received a new job offer that moved them from New York City to Tennessee, Loly continued her clerkship remotely until she decided to make the change. 

She returned her work materials on Friday and the following Monday was working full time for herself. It’s been that way ever since.

Do You Want That Life? 

One of Loly’s greatest insights from her experience is not just the courage it takes to realize that law may not be for you, but also that if you pay attention and look at the lives of the people around you, especially the people that are the ones that have “made it”, the people who are the definition of success in your practice area, and you ask yourself, “do I want that life?”, that’s a really insightful way of figuring out whether or not it’s for you, or if maybe you should be doing something else.

Connect With Loly

Mentioned In This Episode: 

Sarah: Hi, and welcome to the Former Lawyer podcast. I'm your host, Sarah Cottrell, and on this show, I interview former lawyers to hear their inspiring stories about how they law behind to find careers and lives that they love. Let's get right to the show.

Sarah: Hello everyone, this week on the podcast I'm sharing my conversation with Loly Orozco. What I love about Loly's story is that she took something that she loved and ultimately determined that making it a business was a great fit for her. And I know we've talked a lot on the podcast about how sometimes that can be a really good move, and sometimes that can be a not so great move, depending on what the thing that you love is. And how that also works out for you. But I just love this story because I think that she's a great example of someone who really knew herself and knew what she liked and went after it, and well, you'll hear the rest as we get into it. So let's get right to my conversation with Loly.

Sarah: Hey Loly, welcome to the Former Lawyer Podcast.

Loly: Hey Sarah, thank you so much for having me.

Sarah: I am excited to hear your story. I've been following you on Instagram for a number of months now, and the stationery and the other things that you make are super beautiful, and of course, you are a former lawyer. So, why don't we start with you introducing yourself to the listeners?

Loly: Yeah, thank you so much. So my name is Loly Orozco, and I used to practice law, and now I dedicate myself full-time to a small business. So it's a stationery design company called the Little Postage House, and we sell curated vintage postage stamps and also design and print all types of paper things from birth announcements, to wedding invitations, save the dates, you name it, we do all those things. And we print and design in-house, which is really cool.

Sarah: That is super cool. The videos and the reels of the various presses are just like oh, you're producing something that exists in the world. I don't know if you had this feeling when you were practicing law, but often people will say to me, "I just want to make something that is adding something to things." And sometimes legal work can feel a little bit insubstantial. And so I always, seeing that work is really cool.

Loly: Yeah, it's interesting because I think that there's this hunger to produce things and to do things with your hands, and while you're practicing law, you're typing, you're touching paper sometimes depending on if you prefer to do things online, or to write things up. And I always really liked paper, so I would print out cases, I'd read, I would highlight, but it's still not the same as producing something and creating something in the world that's not, it's not theoretical practice, we're actually producing things. And so it is really different and I think a lot of people, especially lawyers, miss that part of life. You're sitting behind a computer, staring at a screen, can get old and you could get tired of it. So, I definitely get that.

Sarah: Let's talk about how you got on the path to practicing law. What made you decide to go to law school?

Loly: I've listened to a couple of the other episodes that you've done, and I guess I'm kind of the weirdo that always wanted to go to law school. For as long as I can remember when I was in third grade, fourth grade, you would ask what I wanted to do, people ask little kids that and I always answered with, "I want to be a lawyer one day." I didn't know any lawyers, so there were no other lawyers in my family, I didn't grow up with lawyers, I don't really even know why. As an adult, I've tried to reconstruct and figure out why I wanted to be a lawyer because I don't think it was the natural decision for me. I liked art, I liked math, I liked science, I liked all of the things that a lot of the people who go to law school say that they hated. I didn't realize that until I got to law school and people made jokes like-

Sarah: They're like, what?

Loly: Yeah. People would be like, "I was bad in math, so I went to law school." And I was like, "Wait, what?" I realized that I was different from those around me when I got to law school, but I liked all of these things I think are a little bit more artsy, and actually really don't like my English classes, the things that I think people that end up going to law school actually really enjoy. But for some reason I really wanted to be a lawyer and I've tried to pinpoint the origin of that, and I think it's that I am the daughter of immigrants, and so from an early age I was always in the position where I would adjudicate for them. So I would translate at the grocery store, I would call the cable company and set up cable. My aunts and uncles also had children, my cousins, and my cousins really didn't want to do that, they weren't comfortable in that role. They were embarrassed by it. And I sort of embraced it, and so I would go to my uncles house and I would adjudicate for him whenever he needed anything.

Loly: And so I kind of saw myself as a person who represented other people, and then one day I guess they realized that that is something that lawyers do, and I decided to be a lawyer. So I think that's why I wanted to be a lawyer, and why I ended up pursuing it almost in a way that was blind, like I never questioned it, it was always law school or bust for me.

Sarah: Mm-hmm (affirmative), yeah. I think that's a very common story for people who decided at a young age they wanted to be a lawyer. It was just sort of like, they didn't necessarily have a really fixed idea of what it was to practice law. It was just like I want to be this thing and then they went towards it.

Sarah: So tell me, when you got to law school, did you at that point have a specific type of legal practice that you thought you were headed towards? Or were you still kind of like, I'm going to be a lawyer?

Loly: So I think people would ask the question, what type of law? And that was something that was hard to answer because I think not having known any lawyers, you don't really know what types of lawyers are, they're just lawyers and non-lawyers.

Loly: And so I wanted and was interested in criminal law. I always thought that it was an interesting area of the law, I think it's something that you recognize especially when you're younger as a type of lawyer when people need lawyers when they get in trouble. And I don't even think that I had really figured out on what side I would be on, or whether it's defense or prosecution, I just thought that it was interesting, especially when you start talking about mental states and things like that. It's something I thought that I would be interesting in, something that I would pursue.

Loly: So I went to Cornell Law School, and you get a very broad education when you're there, everybody does [one out 00:06:50], and I really loved my criminal law class, I loved my con law classes. But I guess the idea of pursuing criminal law, even though I enjoyed those classes, kind of just faded away the moment I got there. And I just tried to learn as much as I could, I tried to do as much as possible to be successful at this thing that you've worked so hard to get to, and then you kind of just end up doing what you do, especially at law school like Cornell, one of the top law schools where you interview with law firms and then you end up summering a law firm. It's just something that you kind of do to build your resume and I kind of fell into that.

Loly: But I really didn't have an idea what I wanted to do. I had a lot of friends who wanted to do human rights or immigration work, and for me, it was more general and I had interest in criminal law.

Sarah: So I relate to that a lot because I went to law school originally thinking I wanted to teach law. I know I've talked about this in the podcast before, and then pretty quickly realize like oh, I actually don't find the legal scholarship to be very interesting. And then it was kind of like, oh well, I'll be a lawyer and like... I graduated from law school in '08, so this was back in the day when the job market was still pretty good. And it sounds like from what you're describing, you had a similar experience where there's very much this message of there's this recruiting thing and you go and you do interviews and you get a job, and this is the path to be on if you want to be successful.

Sarah: And unless you have a very specific idea of a different path, like where you're very single minded, I think it's very easy to get sucked into that stream that flows to OCI, summer associateship and then going to a firm. So is that what ended happening to you or did something different happen?

Loly: No, I definitely agree with that. And I think one of the things that happens and it's just the way that this is structured is that, you do one out, and then you summer somewhere. And usually it's public interest because if you're a one out and those types of jobs that you're able to get, and so you do something usually interesting as a one out. You work for a judge, I worked for an international human rights organization, and so you do that type of work, and at the end of your summer before going back to law school, you interview.

Loly: So you have OCI, and it's like speed dating, well I tell people it's like speed dating with law firms, you get 20 minutes, 20 law firms and you just really try not to mess up their name. So I'd always say, "Your firm," and I never used law firm names, I didn't want to mess it up. And used to get really general, and your goal is to try to get a second date, to get a callback.

Loly: And so what ends up happening is like that process is set up and it's very easy to do, it's kind of like what you're expected to do. And so unless you know for sure that you don't want to do that, there's not really another option. So for public interest jobs, usually they tell you, you have to wait because they don't hire as far out, they don't have recruiters and these huge departments to organize OCI.

Loly: I had a couple of friends that knew from the beginning that they did not want to work in big law. They wanted to do human rights work. They knew exactly what they wanted to do, and they had very clear picture of that. And so they sat out of OCI to wait for the public interest opportunities and those career fairs that happen later in the spring. And so for me and I think for a lot of people, I had friends who wanted to do public interest, that fell into this group.

Loly: You almost felt as if, if you miss this boat, there's a boat there, and if you miss it, that's it. If you don't get a big law job, you don't know for sure that you're going to get a public interest job. So you need to get on the boat because it's really hard to break into big law at another point in time. You kind of have to do OCI, you have to get an offer, or there's something wrong with you. And firms are not going to hire you when you're [inaudible 00:10:45], and they're not going to hire you when you leave. And so you almost feel this pressure that's like it's now or never, and if you're not sure that you want to do it, you should just do it just in case, because you can always leave big law. That's not easy to do, but you kind of think about it that way and I think a lot of people fit into that and end up just going with it, because it's easier with the stream, and to go with this.

Sarah: I think that's so right, and I think the thing that sometimes and I'm sure you saw this happen as well is, stuff like that happens where people are like, well I'll do this because I need a job. I have student loans and et cetera, et cetera. But I'm not going to, it's going to be two years and out.

Loly: Yep.

Sarah: But you sort of get caught up into this machine that has a very steady propaganda of this is the thing that you should be doing and this is the only thing that people who are really serious and want to be challenged in their career do. And all of these things and you go from, okay, I'm doing this kind of begrudgingly in order to create some stability to, oh, this is the only thing that I should be doing because I care about being the best. I care about working hard. And it can, I think it just, and we've talked about this in the podcast many times, it can just shift really quickly without you necessarily being aware that it's happening.

Sarah: Did you find that to be true for you or did you have a different experience?

Loly: Well so I think for me I tend to... And so what's interesting is that if you would have met me when I was in law school, or if you would have talked to me when I was at the firm, I was always very into it. So in law school, I was very involved, so I was on moot court, I was on journal, at the clinics, like you name it, I did it. I gave tours to prospective students, I was just like cheerleader of law school, and then I went to firm and I was like miss law firm. I summered, I pursued every case that I could get, I worked really late hours. I wasn't in it for the fun and the dinners, I really wanted to do well.

Loly: And I think that, that's kind of a personality type that's very common, and the legal industry, you have kids there are bright and they're really hardworking and they just want to do well. And so at the law firm, I was part of different organizations, different diversity groups, I worked on, try to get as many cases as I could, I ended up in one of the more prestigious departments within our firm. And so I was always very caught up in law firm life, and I was really into it and I wasn't fighting it, I just kind of doubled down on it, which I think is a little different than other people that get there, get to law school, or get to firms and realize right away that they hate it. For me I was just really into it, if that makes sense.

Sarah: Yes, that makes total sense. So you mentioned cases, so it sounds like did you end up going to some type of litigation practice or a different type of practice?

Loly: So I went, so I summered at a law firm and as far as the summer program, they let you pick. So it wasn't one of the rotating programs, so at our firm you actually got to try a little bit of everything until depending on how you liked or disliked something, they would give you less of that type of work. And I wasn't really sure what type of law I wanted to practice, prior to that, I only have an interest in criminal law and that's not really something that you do outside of white-collar work. And I knew that the first thing that I need to figure out was whether I was on the corporate transactional side of the fence, or the litigation side. And everybody around me seemed to know, they hated litigation, they hated being in court, or they hated being a transactional trainee. I kind of didn't really know, and so I was trying to figure that out and I realized early on at my law firm that there was one practice area that kind of had a foot in each world, where you could do both.

Loly: And that sounded great to me, and then later you realize it just means you have way more work. So I ended up practicing in an area that's called financial restructuring, which is essentially corporate bankruptcy, and so you have these really fast expedited cases that have to go through the litigation process and in court process to get out in a healthier state. So it's like really fast litigation. Usually you don't have like 10 year cases, which I thought was great because the thought of being in a case when you talk to older litigators where they'd been on a case for 10 years, to me just sounded awful.

Loly: So, it was faster litigation, but you still did out of court deals and transactional work, and so I was really interested in that. And for that reason, I decided, I was laser focused on doing financial restructuring work, which means that I picked a practice area that is very fast paced, comes with a lot of work early on, it's a very lean department, male dominated, very few women. I was usually the only female or minority in a courtroom or at an event, and not one with many exit opportunities, people don't need in-house bankruptcy lawyers. But despite that, I wanted to be a financial restructuring lawyer.

Sarah: Yeah, I did a rotation with a bankruptcy group during my summer, and it seemed very apparent just from that experience that it was very much, go, go, go all the time, for a lot of the reasons that you described. And it was also similarly very male dominated and anyway, just many of the things that you described were also true of my experience there.

Sarah: So you were like, I want to do this specific type of work. This is the type of work I want to do, and you started doing that work. At what point did you start to think, hey maybe this isn't what I want to do forever?

Loly: Mm-hmm (affirmative). I think that what happened to me, it's kind of, I think my life would have turned out a different way if not for my clerkship. And so I started at the law firm after I graduated and my firm, my department in particular encourages people to clark for bankruptcy courts. And so there was an opportunity clerk in the Southern District, there was a bankruptcy judge there who had previously hired people from our department to work for him, and the partners sat me down and they were like, "You're extremely talented, but we would love for you to do this. Have you ever thought about clerking, have you ever been interested in that? We would support you during this, and we would recommend you. You're understanding that you would come back and we like when our associates have this experience." And they would always tell clients, "Oh, we have four clerks." So it's like a thing that they liked.

Loly: And so I always had an interest in clerking but I never really pursued it and it was seen like a great opportunity, so I interviewed with the judge, I loved the judge, and he gave me an offer to clerk for him after, it was almost my second year. So I was at the firm for almost two years, and then was sent to clerk.

Loly: And I interviewed with him pretty early on, I think I'd been at the firm for eight months when I first interviewed, so it's something I decided to do and committed to do pretty early on. And I had that offer and I just kept working and I was working on really big cases with the head of department, and I was in a really good place within the department and it was coming up to the point where I needed to go and clerk, and I kind of was very afraid to clerk. It seemed intimidating, it seemed like it would be very challenging. I wasn't sure if I would excel in that sort of atmosphere. I was used to working in a big department where we were all on the same floor, so you would run into each others office and you'd constantly brainstorm together. And it was a very social and very high energy.

Loly: In the law clerk position working for a judge, it's just you, your co-clerk, the deputy and the judge, and very small chambers. So I wasn't really sure if that environment was one that I was going to do well in. I was also just worried about leaving the firm. So I was at this really weird point, I was really hesitant to leave my practice, and I remember talking about it with another associate who said to me, "You just need to do it, it's just prestigious, check that off, put that on your resume, and then you're going to hate it, but you need this type of work. But you can't be happy doing anything but this. You need the fast pace environment, it's just who you are."

Loly: And I remember her telling me this and just nodding my head and thinking like, yeah, you're right. What would I do myself with more time? I wouldn't be happy doing anything but this. Not ever going home and pulling all nighters, this is what makes me happy, right? Which is kind of really delusional looking back at it.

Loly: But yeah, I felt that way, and then I went to clerk and it was amazing. I loved every minute of it, I spent time on things and actually thought about them and got to write decisions and my judge, he's just a very great teacher, a great mentor, and he would just let us write decisions and figure out what the conclusion should be without pre-dictating it, and then you would present it to him, which was always very scary because what if you got it wrong, you'd have to rewrite the whole thing. And so it was a lot of responsibility and I loved the intellectual challenge, and I also found myself with more time.

Loly: And so I started exploring and getting to know a side of me that I put away for a long time, so I started drawing, I started pursuing art, and things that I loved growing up that I didn't have the time to do when I was pursuing, getting into law school and undergrad, being in law school, working at a law firm. And so it was almost like getting to re-know myself with this time that I had, and I actually was really happy and realized that I could be happy not being a big law lawyer.

Sarah: Yeah, it's so interesting, and by the time we're recording this week, the first half of my conversation with Jenel Christian, released next week. The second half is really seen and she worked in big law, and she ended up making the move to a smaller market intentionally to get into a place where she would have more free time. And one of the things that she talks about is, having this realization with that move of, oh, there are other things I could be doing with my time. Other people do things other than just work and errands.

Sarah: And I think to someone listening who doesn't have the experience of being a lawyer, and in particular working in a big law firm, I feel like that probably sounds like obviously, what are you saying? But there really is I think, like you said, this story that's told and retold when you're in a big law firm where it's like, not only is this the best thing that you could be doing, it's the only thing that you could do that would ever be good enough for you and your brain, because what would you even do if you weren't working the way that you work here?

Sarah: The reality is I think like you said, for a lot of people who went to law school, part of it is that they have set aside lots of things that they enjoy or that are parts of their personalities, that they just aren't spending time on because the path to get where they ended up in law required them to set those things aside, and they don't... It's like you almost have to remember parts of who you are.

Loly: Yeah, and it's sad when you think about it, that it happens to you. But getting into law school, especially a good law school it's hard. Going to law school is not easy, taking the bar is not easy, being in law school is not easy, and working for a law firm. These are all things that demand a lot of who you are, and there isn't time for anything else.

Loly: And so, after leaving law school, my law firm, and clerking, I did those things in New York, and I would talk to my friends or people that were not lawyers and they would always ask me, "Do you go to comedy shows all the time? Do you go and see Broadway shows all the time? It must be so great to live in New York." And I was just... It was weird for me to say like, "Oh no, not really. Yeah, New York is wonderful but I never get to experience these things, it's not Sex in the City, and I'm not going to all these fancy places."

Loly: The life of a lawyer is not that glamorous, you literally just sit in the office-

Sarah: You're like, "I eat a lot of dinner at my desk."

Loly: Yeah, yeah. Getting a car home, to drive you home at 2:00 o'clock in the morning, and getting dinner, bill it to the client if you're there past 8:00 or whatever time it was. That was my life. If I ever left the law firm and it was still daylight out, that was just like a remarkable day. Seeing the sun before you leave at the end of the day was like this glorious thing. Taking a vacation, like whoa, you're a daredevil, you would go on vacation? What?

Loly: These things sound really crazy to people that have not lived it. People that have not lived it just think like, wow, you went to an Ivy League law school, you work in big law, you've clerked in the Southern District, that's the life, that is success. But they don't know what it's like until you walk that path.

Sarah: Yeah. So tell me what happened. You do your clerkship and people were saying do it to get the credential, but then you really enjoy it. And you start having time to explore other interests outside of just your job. As you were coming to the end of the clerkship, where were you in terms of your thinking about your legal practice? Were you like, "I'm going back to the firm," and you were still happy about that? Or were you having this realization of, oh, I actually like this lifestyle that I've been able to develop and I'm about to give that up again?

Loly: Yeah. So going back to the law firm, the thought of going back to the law firm was very hard. I didn't want to go back, so just as badly as I didn't want to clerk, I didn't want to go back. It was like this weird thing, I was like oh maybe I just don't like change. But I was not looking forward to going back. I was not looking forward to what it would mean for me and my life. My weekends, my evenings, and I didn't have an easy clerkship. My judge was there every day at 6:00 am, and he left every day very late. He was known as one of the most hardworking judges on the court, and we produced probably 10 times as many decisions as other judges. So it was a very hard clerkship, and despite that, I still had way more time than I did at the firm.

Loly: And so I remember talking about this with my husband, with my friends, with my close friends, and I would say that I felt as if when I was at the law firm, I was on a hamster wheel. And it's this wheel that you're on, and you don't really know why you're on it, or where you're going, but you're kind of just on it, and you're spin, spinning and spinning. And clerking was me stepping off of the hamster wheel, and I was disoriented when I came off of it, I didn't really know what to do, I could move around, I could explore things, and the thought of going back on it, I knew better, and it seemed incredibly difficult and it wasn't something that I wanted to do.

Loly: I didn't want to get back on that hamster wheel, and I was afraid that once I got back to the law firm, given my personality type, I tend to make the best of situations and I tend to drink the Kool-Aid that I was going to forget that I really enjoyed having a life and that I was going to go back into being on these cases and doing everything, and joining all the organizations at the firm. And I was going to really root myself within the firm and never leave.

Loly: And so something that I was very afraid to do and very hesitant to do but I kind of had decided that I was going to go back. They give you a clerkship bonus when you go back. I wasn't really sure what else to do, I wasn't going to change law firms, I knew that all the law firms were kind of the same from a work/life perspective, especially in my practice area. So I went back to my law firm because I liked the people there too. So I decided just to go back and just do it.

Sarah: So, tell me what happened next?

Loly: When I got to the law firm, it was hard for me to take things as seriously as I'd taken them before. It was hard for me to do an all nighter because a random partner had a random questions about something that we all knew the answer to, but they wanted you to find the case that everybody, like me who didn't exist after clerking, that just seemed like such a waste of time.

Loly: It was hard for me to really get back into it and to give myself completely to this practice. And I think also when I left the law firm, I was in all these really big cases with the heads of our department and they were important cases. And when I came back, those cases were fully staffed up, and so there weren't new cases that were coming in, so I got put on all these little smaller cases with partners that I never worked with, and I really, really didn't enjoy working with.

Loly: And so all these things together [inaudible 00:28:41] so that I was very unhappy at the law firm but I tried. I joined different organizations, the firm sent me to a leadership retreat, they were really trying to invest in me, and I was really trying. They knew that I was unhappy, but I was trying to get back into it, to be my old self, and I was just having a really hard time taking this seriously or wanting to do that to myself again.

Loly: So I had at that point already started my business. I started my business actually while clerking, and we can talk about that and how that started. So I found myself enjoying these artistic things that I was doing at 2:00 o'clock in the morning when I got home from the law firm, more than the things that I was doing during the day as a practicing lawyer. And so I knew that and was coming to accept that maybe the law firm and big law wasn't for me.

Sarah: Hey, it's Sarah and I'm popping in here to remind you that I have created a free guide, first steps to leaving the law for anyone out there who is just like, "Argh, this job is the worst, and I need out. Where do I start?" Which that is exactly where I was when I realized that I didn't want to be a lawyer. So you can go to and sign up and get the guide in your inbox today. And when you grab that guide, you get on my email list, which is the way I keep everyone the most up to date about everything that's happening with Former Lawyer. It's also the best way to get in contact with me, because I read and respond to every email. So, if you are ready to figure out what's next for you, go to, download the free guide, first steps to leaving the law, and get started today.

Sarah: So let's talk a little bit about that realization and how you felt about it? Because one of the things that comes up, I know for a lot of people, I'm sure for many people who are listening, is they start to think about leaving legal practice, and it's extremely hard because they find that their identity is very wrapped up in being a lawyer and they also struggle a lot with this idea of I'm going to be throwing away all of this time and money that I spent becoming a lawyer. Were those things that you struggled with, or not? Just talk a little bit about that.

Loly: So I think that for me it was hard, the thought of leaving the law firm was really something that was difficult. All of my friends worked at the law firm, and that kind of I think happens to a lot of people where you have a lot of friends by circumstance. People that are around you all of the time, more than your friends and family. So they are your friends. The thought of leaving the firm was difficult from that perspective.

Loly: I also liked the people I work with. I think a lot of people hate their law firms, hate the people that they work with, but I actually had pretty good relationships with a lot of these people, when I got married, they were invited to my wedding. And so the thought of leaving the firm seemed like something that it really wasn't an option. I wasn't really sure, I knew it wasn't for me, but I didn't really think that I could leave, and a part of me thought, maybe I'm not going to go to another law firm, but maybe I can teach law and do something that requires less time and it allows me to be more balanced, but not leaving the law.

Loly: The thought of abandoning the law after I invested so much time and effort becoming a lawyer, seemed like something that I wasn't going to do. So even though I was really enjoying this artistic thing that I was doing, on this business that I was doing in secret, because I didn't tell a single soul other than my husband that I was doing this other thing. I really didn't think about that seriously as something that I could do professionally or as an alternative to being a lawyer. I was still trying to find a way to continue to be a lawyer just in a different sense, almost to try and rebrand what I was doing, if that makes sense.

Sarah: Yeah, that makes total sense, because I think, honestly I don't know that there is a lawyer who ultimately ends up doing something else, who doesn't go through at least some period of, well maybe I can stop doing what I'm doing but do some things slightly different.

Sarah: Basically to be able to make enough of a change to not be as miserable, but not so much of a change that you kind of have to face some of these really, really big and really difficult mindset issues around the sun costs and identity, and all of those sorts of things.

Loly: Yeah. I also think that there's this weird thing that a lot of us, maybe especially women think, that you don't want to be the stereotype. Somebody like works for a law firm and you couldn't make it. And I think you don't want people thinking that of you, you're afraid that people are going to think that, especially if you're good at your practice area. If you're somebody that maybe could make it, you don't want people thinking, oh, she must have not made it. It wasn't that she wanted to leave the firm, it's just she wasn't cut out for, her firm was never going to make her partner.

Loly: So you're always fighting that too, and you kind of have to get over it and stop caring what people will think about you. But that's something that's in the back of your mind, that you don't want to quite and you don't want people to think that you're a quitter.

Sarah: I think that's so right. I know I really faced this feeling of, I'm a woman and I'm in big law and I can do this so I should, that kind of thing. And I know we talked about it in the podcast before, I can remember specifically talking about it with Jessica Medina, she also was in big law and she was a single mom, and she talked about feeling this pressure of like, feeling like she needed, because she could, she should, because to prove that it's possible and to not have people be like, oh that person couldn't hack it. And these are real pressures that people feel, I think especially people who go to law school and have sort of that service and others oriented mindset.

Sarah: You were talking about your original interest in going to law school came from advocating for people, and so it can be very easy to fall into this mindset of, it doesn't really matter of what I feel about this, because I need to be doing this for some greater good, whatever that greater good is. And I know there are a lot of people who struggle with feeling that way.

Loly: Mm-hmm (affirmative), yeah. You feel like you need to make it, so that other women can make it. And you kind of have to get to the point where you realize that, you don't have to do it. Just because you can make it, or because you can do it, you really don't have to, and that's the beauty of it.

Sarah: Yeah. I think that is really, really important for people to hear. So let's go back and talk about, you mentioned you started your business while you were clerking. So tell me about that.

Loly: Yeah. So when I was clerking, even though my judge kept a very busy schedule and we did a lot in-chambers, I had more time. I would usually leave chambers around 8:00 or so, and so I was getting home much earlier than when I was at law firm, and weekends, I usually didn't have to work weekends. So it was a really big difference.

Loly: And so I had all of this time and during that time, I somehow I think randomly, your mind starts to go to things that you enjoy and things that you enjoyed before becoming a lawyer now that you have time to think and there's clarity. So I started being drawn back into art. I always, prior to going to law school, art was always a part of my life. Growing up, I took every class that I could, I took graphic arts, sketching, anything that I could do, I did. I would always beg my parents to take me to Michaels or to the craft stores. And so I was usually doing something or creating something with my hands.

Loly: So I found myself back into those old habits, and I randomly had an idea to start a business, and it wasn't even, I don't think I even thought about it as a business. I really didn't think about it from an income generating perspective. I think it's just that I wanted to do this and it was kind of an excuse to do art. I thought I could put it online and I could sell these things. I wasn't really sure if anybody would be interested in buying these things, but it's kind of like, I think as a lawyer and somebody who went to law school, you know everything has a purpose. And so I wasn't doing art just to do art, there was a purpose to it and that purpose was to sell it and to put it out there.

Loly: And so I started with a really simple thing. I started doing vintage postage curation for weddings, so when people get married, they spend all this money and all this effort on their invitations, and then they just go to the post office and they slap a forever stamp on it, and it could be like a frog stamp, an American flag stamp, but it doesn't really go with their hand written calligraphy embossed invitations. That just to me seem counter intuitive, and so I started offering curated postage sets that reflected the event themes, the color scheme and their story. So if the groom is Michigan and she's from Florida, and they met in New York, I would put together a curation through stamps of those interests for their invitations.

Loly: Then I also started designing and printing invitations for people, and people started buying things and we started making sales. I didn't tell anybody, so it wasn't as if I was getting any referrals from anybody that I knew. It was all strangers that found me through [inaudible 00:38:36] as marketplace, and then later through social media.

Loly: So I just kept doing this and it started doing really well, and it kept growing, and it started taking up a lot more of my time and so it got to the point where I wasn't really sleeping. I was clerking by day, and later working at the law firm by day, and staying up until 4:00 o'clock, 5:00 o'clock in the morning, and spending all weekends fulfilling orders and working on things.

Sarah: Okay, so I have a couple of really technical questions about the actual work. First of all, and maybe everyone else knows this, but I don't know what I would do if I wanted to curate a vintage stamp collection. Does that make sense? Was it something that you'd done previously for yourself, and so you knew that that was a thing and you did it? Or how did that come to you as a thing that you could do? Does that make sense?

Loly: Yeah, because it's really random, right? And so when we... I had designed our wedding invitations when we were married, and there was a local historic printing museum where we printed them. And so it wasn't the type of place that you'd go to for invitations, it doesn't really cater to that. So I always did things myself when we got married, and one of the things I did myself, aside from designing our invitations, was curating a vintage postage set. And the reasoning behind that was, so we had these invitations that were made on these old printing presses, and we had handwritten calligraphy, and the envelopes were these paper craft envelopes that looked really old and very cool, and I went to the post office to figure out what postage to put on them, and all of the options were all these modern options that didn't make sense. It was literally an American flag stamp, I can't remember what they had back then, but there are things that really didn't go with everything else. They kind of seemed out of place.

Loly: And so I used, I think my skillset as a lawyer to do what lawyers do, which I over-researched this. I researched everything about postage to figure out alternatives. I started stumbling onto historic stamps, stamps that had been issued in the early 1900s, in the early 1950s, that were really different. It's back when the post office was actually making and producing their own postage stamps, that were colorful and had a lot of beauty, and they seemed to go much better with the aesthetic that I was doing for our invitations. And postage stamps like currency, despite their age, can still be used if they're unused stamps.

Loly: You can use a dollar bill from the early 1900s to buy something that's worth a dollar, it still maintains its value as currency, and postage is the same way, if the stamps are unused, you can still use them. And I have used from the early 1900s to send out invitations, you just need for the stamps to add up to the amount of postage that's required to send that out.

Sarah: That's super cool. And I love how you specifically mentioned part of what enabled you to figure that out is the skills that you developed as a lawyer, because one of the other big fears that people have is, if I go do something else, I'm throwing away, all these skills that I've developed, will go to waste. And after speaking to lots and lots of people who have moved into other things, every single one says, I use this type of skill that I developed in this way, and this type of skill that I developed in this way. So I think that's really important for people to hear.

Sarah: The other thing I wanted to ask you about is you were talking about printing invitations and typically when someone hears printing these days, they think like printing on an inkjet printer. And I don't know, maybe that is where you started, but I know that what you're doing now is you're printing with, I think of them as old fashioned printing presses, I don't know if that's the right way to describe them. So can you talk about that piece of it a little bit?

Loly: Yeah. So for our invitations when we got married, I had this museum that had all these printing presses do that for us. I fell in love with it. I loved going to visit and to see the process. And I loved these machines. So they're these cast iron machines, some of them are from the late 1800s, early 1900s, and they weigh like 2000 pounds each. And it's back when they would literally get type and they would line up, like for a newspaper for example, they would literally line up the type, and they would lock into the printing press to press out newspapers, or to print out programs or whatever it was. And so these machines are rare, but you can still find them and you can still use them to print.

Loly: And so when were in New York, I designed our wedding invitations and had them print them for us, and so when I started selling invitations, at first it was mostly digital printing because I didn't, living in New York, we didn't have a lot of space. It's really hard to get a machine that weighs as much as a car into a New York studio apartment. I thought about it, I tried to figure out how to do it, but there is no way to fit through the door or to keep in the apartment. They would literally break the floors, and it would end in the person down stair's living room.

Loly: So I quickly realized that I was not getting a printing press, so I started with digital printing. So I was designing for digital printing, and I was also to the extent that people wanted this other print method, I was outsourcing my printing in the beginning, and I was learning at the same time. Again, being a lawyer, researching, YouTube videos, I was reading up old manuals, I was learning as much as I could about printing in these other ways using antique printing presses. I was taking online conferences on it, and I was also researching where to buy it, how much do they cost, what are the costs associated with it, where do you get your paper to print on these machines, because you need to have a much thicker paper.

Loly: And so I kind of knew, I was at a point where I knew everything about operating one of these machines, printing on it, getting plates made with my design work on it. I knew everything that there was to know, I had just never used one. So when we moved to Tennessee, we left New York and moved to Tennessee in 2019. My husband was offered a job out here, I had space, and so first thing I did was buy one of these printing presses. I still had never used one, but I bought one. And then it was just putting all of that knowledge into practice, and with trial and error, I actually started producing my own work.

Sarah: Okay, so you said you moved to Tennessee in 2019. Can you talk to me a little bit about the timeline, so you're clerking, you went back to the firm, you also were running your business and staying up until 4:00 or 5:00 in the morning. How long was it until you got to the point where you were like, I can't do both?

Loly: Yeah. So it's weird and the part that we kind of skipped over is that when I went back to my firm after clerking, I got back to the firm, I think it was in October of 2016. And I wasn't very happy, but I kind of had decided that I need to figure out how to make myself happier. I hadn't really realized that I wanted to do this other thing that I was spending all of my time thinking about or doing when I wasn't at the firm, and I was getting to this point where I was just really, really unhappy. And in May of 2017, my phone rang. I remember being at my office and I was really miserable that day. I was looking online for teaching jobs, I was thinking maybe I could go and I could teach somewhere.

Loly: And I get this call and it's my judge, and my judge wants to see how I was doing and he wanted to let me know that there was an opening to work for another judge in the Southern District on a really high profile case that came in. And it's a one in a lifetime, there's never been a case like it, everything was going to be issues of first impression, it's based on a new statutory provision and they need somebody like you, he said, "Somebody that can be creative and that has clerked before, that has that knowledge, and can help this judge set up chambers and can train other law clerks, because this is going to be a very big case. And I gave her your name, and she would like to meet with you."

Loly: I thought it was extremely interesting, I loved clerking the first time, and so I went and I met with this judge, and I left with an offer. She wasn't even sure if she had funding to hire me, but she was going to try to get that funding for this new position that they were creating for me, and I left my firm, and I went to clerk for the second time, for a judge in the Southern District.

Loly: And so I stayed with that judge up until October of 2019, working on this case, and it was during that second clerkship that I kind of realized and accepted that I didn't want to find, after the clerkship, I didn't want to look for another job, that I just wanted to dedicated myself to doing this thing outside of the law.

Sarah: How did you feel when you realized that, that option was opening up for you? Because you said you remember you were in your office and you were looking for teaching jobs because you clearly were like this is, what I'm doing now is not working. Did you feel relieved? What was that experience like for you?

Loly: It was this weird thing where it was like he knew. My judge knew that, he didn't know, and I talked to him about it, he knew that I was hesitant to go back to the law firm, we talked about it, and he told me that, that was not uncommon, that happens to a lot of people, but they'd be okay, that everybody goes back and you kind of get over it. But it was almost like a God... It was just thing that just happened at the right time, and it wasn't as if I was leaving my firm to go to another firm. It wasn't as if I was leaving the firm to go and work next door at somebody who competes with it. It was literally this case that it's one of a kind, and people could understand it.

Loly: So I never had to explain myself to the law firm or to the department as to why I was doing it. For a lot of people, it was like a no brainer, like you have to do this. You're going to be the expert in this new practice area that is going to be a big part of restructuring in the future, and then you're going to come back with that skillset. And so I kind of was able, I cheated, I got to avoid the question of me leaving big law, and having to tell everybody. I kind of just left to go and do this thing, and then I never went back.

Loly: Leaving the clerkship was particularly difficult because the cases were not over yet, and my judge wanting me to stay, but we moved to Knoxville and I was working remotely for her at the very end, from April to October of 2019, and because of the distance, I said that I didn't really want to work remotely anymore and I want to explore other things. But I never even told my judge that I was leaving the law.

Loly: So I very much cheated. I never told anybody that I was just leaving the law, I kind of just did it. I ran away in secret.

Sarah: And after October 2019, did you go basically straight into running your business full-time?

Loly: Yeah, I literally like... I traveled to New York to turn in, I had a court issue cell phone and a court issue computer and all of these things, because the cases required that we travel a lot, so I was always traveling with this judge. And so I left from Tennessee, I went and dropped everything off, I think it was like a Friday or something, and Monday I was running my business full-time, because I had built this business that really had become this full-time endeavor, and whenever I wasn't working for my judge or working at the firm, I was dedicating myself to it. And so I had something to do. If something, I usually was like falling behind. And so I had enough work to do a 9:00 to 5:00, to do a 9:00 to 8:00, to fully dedicate myself. So next day, I was here running my business.

Sarah: And here we are.

Loly: Yeah, busy.

Sarah: A year and a half I guess almost now that its been.

Loly: Yeah, full-time.

Sarah: That is so cool. And I'll link to your Instagram in the show notes, but really people [inaudible 00:51:35] me, like you need to go see the stuff that Loly makes, but it is stunning. It's really beautiful. Yeah, it's really amazing stuff.

Sarah: So Loly, as we're getting to the end of our conversation, is there anything else that you would like to share that we have not talked about yet?

Loly: I think that there's a lot and I can talk about this all day. I think that my journey is a little bit different than that of other people. I tell people I stumbled my way out of big law. If I had not clerked and taken the time to have some distance between me and big law, I don't know if I would have ever realized that I was unhappy or that I wanted to do other things. I think I would probably still be at the law firm pursing partnership. I ended up in this life that I prefer and I really do think it's what I was meant to do. I always liked art, I had a lot of professors growing up that tried to talk me out of going to law school, wanting me to go to art school. I ended up exactly where I'm supposed to be, but life kind of pushed me out of big law.

Loly: And so I think it's really hard, and if you feel the courage to realize that big law is not for you, or to realize that law is not for you, and to walk away from it. But I think that if you pay attentions, the signs may be there. I remember talking to a lot of people at the firm that would randomly tell me how unhappy they were. I had a partner one day at 2:00 o'clock in the morning that asked me why I was pursuing the law and why I wanted his life? He was like, "Why would anybody ever want this?" And so sometimes when people are vulnerable, they kind of spill and you see that they're not happy, and I saw that when I was a young associate, but I kind of just ignored it and thought, oh they're having a bad day. People are allowed to have a bad day.

Loly: So I think that if you kind of pay attention and if you look at lives of the people around you, especially the people that are the ones that have made it, the people are the definition of success in your practice area, if you ask yourself, do I want that life? That is what it is to be successful. So if you are successful and you get that life, is that the life that you want? And if you ask yourself that, I think that, that's a really insightful way of figuring out whether or not it's for you, or if maybe you should be doing something else.

Sarah: I think that is incredibly helpful insight, and really, really true. Okay Loly, tell me where people can find you online and see the beautiful things that you make and buy the beautiful things that you make and all the things.

Loly: So you can find me in a bunch of different ways. You can see a lot of my work on Instagram, and so if you go to @littlepostagehouse, you'll see videos and pictures and a bunch of things. It's a really great, we have like an online portfolio. You can also buy our things that we make on our website, so it's just I'm also on Facebook, I'm on this thing called Club House, which is a new social media app. And I'm on [inaudible 00:54:46]. But using Little Postage House, you're going to find me one way or the other. Just type into Google. But if you really want to see everything, Instagram is a really great place to see it.

Sarah: Great. And I will link out to those things so that people can find them easily. Thank you so much Loly for sharing your story, it was really great to talk to you today.

Loly: Thank you so much Sarah.

Sarah: 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 Until next time, have a great week.