From Biglaw to Running a Creative Business with Loly Orozco (TFLP 086)

Loly Orozco is a former financial restructuring lawyer turned stationary design company owner. Her 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.


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. 


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.


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. 


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. 


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. 


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.


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.  


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. 


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. 


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.


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


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