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 on the podcast, I'm sharing my conversation with Tiffany Obeng. You'll hear as we're talking, but Tiffany emailed me about what she is doing. She is a former practicing lawyer who now works in a non-traditional legal role and also is an author and publisher of children's books.

Pretty much as soon as I read her email, I was like, "Yes, I want to have you on the podcast immediately." So she founded a publishing company for the publishing of her books. It's called Sugar Cookie Books.

The books that she writes—Tiffany is a Black woman—she, in particular, writes stories that reflect the experiences of Black children and families. If you are a parent of young kids, you are probably aware that diversity in children's books is very lacking. You really need to be intentional to seek out books that have diverse representation.

For me, as a white parent of white kids, that has been a big priority. So literally, I got Tiffany's email. I read it. I emailed her back. I was like, "Yes, let's record ASAP."

So this is my conversation with Tiffany, all about how she started writing, how she accomplishes having a full-time job and also writing, and all sorts of other things about things that I know many lawyers will relate to, including having this sense of coming out of law school that if she didn't get into Biglaw, that somehow she hadn't "made it." Then her experience of eventually getting into Biglaw and learning maybe it's not all it's cracked up to be, which is a conclusion with which I heartily concur. Okay, that's enough from me. Let's get to my conversation with Tiffany.

Hey, Tiffany, welcome to the Former Lawyer Podcast.

Tiffany Obeng: Hi, Sarah. I'm so happy to be here.

Sarah Cottrell: I am very excited for you to tell your story. I know we haven't talked that much before this, so it'll be the first time for me hearing some of the details. Before we get into the specifics, can you introduce yourself to the listeners?

Tiffany Obeng: Sure. So I'm Tiffany Obeng, and I am a lawyer by trade. I don't know if I should say former lawyer, but maybe I should. It's all semantics, right?

Sarah Cottrell: Yes. Some people are comforted by "you're never not a lawyer," and some people are comforted by "I never have to call myself a lawyer again." So it's really a personal preference situation.

Tiffany Obeng: I think I'm in the former. I paid, I still have student loans.

Sarah Cottrell: Yep, yep, I hear you.

Tiffany Obeng: I'm going to keep my bar license active, even though I'm not practicing. So I'm always going to be a lawyer of some sort.

Sarah Cottrell: Yeah, yeah, I hear you. I was just interviewing someone last week and we were talking about this and I'm like, "I still have a license. I pay for it to be inactive, but like, I earned that thing. It is mine."

Tiffany Obeng: Yes, yes, yes. So yeah, the practice areas that I was in and still do, as a lawyer by trade or legal-adjacent career, is employment discrimination. So for years since I graduated, my focus has been in employment law, employment discrimination, emphasis on equal opportunity.

So that's a little bit about me. I also branched off and created my own children's book publishing imprint, where I publish children's books that feature diverse children and families in places where they have historically been absent or underrepresented. That includes in children's literature and in the workplace.

Sarah Cottrell: I love that. Literally could not love that more. I think that is super necessary, especially here in June of 2025.

So yeah, we're definitely going to talk more about that. But why don't we start where we usually start on this podcast first, to just give people some backstory. Can you tell me what made you decide to become a lawyer in the first place?

Tiffany Obeng: What's so funny about this question, because I was listening to some of your prior episodes, particularly the one that just aired, I'm like, "Wow, this sounds so similar."

Sarah Cottrell: Yes.

Tiffany Obeng: So it was my destiny. It was written in the cards. My mother instilled in me that I was going to be a lawyer. Teachers that I came across said I would be a lawyer. Other family members said I would be a lawyer.

What did that mean? I did not know. I don't think my mother and the teachers knew either because I am the first and still only lawyer in my family. I did not know a lawyer in real life. As I say on every podcast or article that I'm in, the first time I met a lawyer in real life was in the 11th grade.

So imagine 11th grade, you're a year from graduating from high school and going to college, but I'm already knowing that I'm going to be a lawyer, even though I've never seen one in real life. Then I hadn't seen a Black female lawyer until I got to law school.

So it was just planted in me. I did not know what it meant to be a lawyer. It's like, either you can be a lawyer or a doctor because the idea is that lawyers make so much money. They're so successful. They're so smart. They're so articulate and all these things.

I will say that I am a really great reader. I did enjoy—or do enjoy—writing, as we will probably come to know. I do enjoy writing. They said that I like to argue, which I still disagree with. I argue that I don't like to argue.

Sarah Cottrell: I was going to ask if there was something specific that people pointed to when they said, "Oh, you should be a lawyer," because for many kids it's either they're told, "You really like to argue, you should be a lawyer," or, "You really like to read and write, you should be a lawyer." So it sounds like you kind of had all of those things going on, the trifecta.

Tiffany Obeng: Right. And not knowing, again, I feel like looking back on it that my mom, she didn't really know what lawyers did because, again, she hadn't been around lawyers. So what people think about lawyers is that they argue all the time and that they are intellectual, which are not bad things.

So I believe that now, again, reflecting back, the core of who I was—or who I am—is someone who stands up for what I believe is right and stands against what I believe is wrong. I think that has always been a trait of mine.

So it could look like arguing if you're just a person that's not, even as a child, who's not going along to get along, if you will.

So that's how I ended up in law school. It was planted in me as early as probably third or fourth grade. I did really well in school so I could achieve high honors. I went to undergrad and accidentally graduated in three years.

Sarah Cottrell: That's such a lawyer move. Oops, I graduated in three years.

Tiffany Obeng: Two weeks later, I'm stepping onto my law school campus to conquer the world. Then I realized, "What am I doing? What am I doing here, and where am I going?"

Sarah Cottrell: Yeah. Was that like a pretty quick realization? Like you basically got there and you were like, "Wait, what, what?"

Tiffany Obeng: No, it wasn't until probably the end of first semester in law school. So there are three years in law school, as those who are listening know, or should know. So you have end-of-term exams, at least at my school and a lot of other law schools.

All you get is one big exam. You don't get little quizzes throughout or anything like that or knowledge checkpoints. It's just one big exam at the end of the semester. So I made it to the end of semester.

When you're used to—and Sarah, I know you can attest to this because I listened to your podcast—when you're used to being a high achiever, like you're an A honor roll your whole entire life, graduating summa cum laude, like top of the cream of the crop, then you realize that you're just in the middle of all these smart people, or people that are supposed to be smart as well, you're like, "Wait, so am I?"

Again, I'm coming from a background where I've been told all my life that I'm smart. I've been showing that I'm smart. I've been top of my class everywhere I've gone. Very little effort, might I add. You know what I'm saying?

Sarah Cottrell: Yeah, yeah, totally.

Tiffany Obeng: When you come into this competitive world of law school, you realize that you're not the smartest. So that's an adjustment. Then it makes you start thinking or wondering, "Well, should I be here?"

I mean, I got here. I went to one of the top law schools in the nation. So I'm like, "Okay, well, I got here, top law school, only five people in my 1L class that look like me."

Sarah Cottrell: Yeah, it's classic top law school energy.

Tiffany Obeng: Correct. So that's another layer. You end up in the middle of your class or bottom top of your class and you're like, "What am I supposed to do?"

Then the subjects that you're learning—because 1L year is just core classes—you're like, "I'm learning all these things, but what am I supposed to do with this?" I don't know what else is out there other than criminal law because that's all they really show on TV. That's the dramatic stuff. That's fun to watch. No one wants to see transactional attorneys or anything.

So it really wasn't until my 3L year, as I'm limping along trying to reclaim some type of academic glory—so 3L is the last year of law school—I'm still like, "What am I going to do?" Oil and gas? I want to pluck my eyebrows out one by one. Securities sounds like it could be cool since it's procedural, and who can go wrong with a procedure?

But I really did not know. Nothing was really pulling at me. I don't want to be a criminal lawyer. I'm seeing people be accepted to the law review journals. I remember growing up, I'm a great writer, but I'm not accepted to be on a law review journal. So it's like, "Okay, I'm failing there." You feel like you're failing there. Mock trials? I'm not doing them.

The person who is doing them, he's like a top litigator in the making because his dad was a litigator, his granddad was a litigator.

Sarah Cottrell: Oh gosh.

Tiffany Obeng: So, sitting in my 3L class, a class came about, it had just gotten there, it was employment discrimination. When I'm flipping through those pages and realizing that workers have rights and rights to opportunity, like the opportunity to be hired, the opportunity to work, the opportunity to work free from discrimination based on how I look, based on how I was born, I was like, "This is fascinating."

So I finally felt like I knew why I was at law school. I took employment discrimination first, and then employment law, it was offered the second semester of 3L year. Yeah, and I found that fascinating.

So I set my sights on, "I'm going to be a lawyer, but I'm going to be a lawyer in the space where," in my mind at the time, "I can help the underdog. We can achieve diversity, equity, and inclusion. That’s what I'm going to do." But when I graduated and went into practicing, it doesn't really end that way.

Sarah Cottrell: Yeah. Oh gosh, I have so many thoughts. I'm going to try to corral them.

So I think there are so, so, so many of us who go to law school because, like you said, you characterize yourself as someone who is willing to stand up for what is right or what you believe in and stand against things that are wrong. I think so many people go to law school because that is something that is very core to who they are.

The thing that becomes a challenge is that a lot of us go to law school and then we end up in just general civil practice, and that is not really consistent with the thing that drove us, or at least one of the things that drove us, towards law school in the first place.

And then also—and I'm curious to know, I don't know all the details of your practice—but I know that I have lots of friends and just people who I know who were interested in employment work. But then ultimately, especially if you go work for a larger firm, you're typically defending against employment discrimination cases.

Which, in some cases, are not valid, but it can often feel like you're basically doing the opposite of what a lot of people want to be doing when they're like, "Oh, employment law, that's cool and interesting and could help people."

Tiffany Obeng: Yes. So you're exactly right. When I graduated, which was in the middle of a recession—

Sarah Cottrell: What year was that?

Tiffany Obeng: Oh my gosh. I have to date myself, 2009.

Sarah Cottrell: Okay. I graduated in 2008, which is why I asked. It's come up on the podcast a lot, people coming out in 2008, 2009, 2010, and the impacts that it has had on people's career trajectories.

Because I was in the last class that kind of got in. If you didn't get fired in that first year or two, it shook out. But people the year after me and beyond had a much, much, much, much, much more difficult time.

Tiffany Obeng: Yes.

Sarah Cottrell: Yeah. Yes. So everyone who's listening knows.

Tiffany Obeng: Yes. So I came out in 2009, couldn’t find a job. At my law school—and probably a lot of other top law schools, or law schools period—the pinnacle of success when you graduate is to get that Biglaw job. No other options are even presented. It’s Biglaw or fail.

So it's just building up, building up this impostor syndrome on my side, which I did not realize until 2024, really. This is all the reasons why I felt the way I felt toward law. We’ll get to that, hopefully.

But anyway, I graduated and I finally landed a job at a solo practitioner's office doing, as you said, Sarah, general civil practice. So, for my first one to two years out of law school, I'm doing general civil practice.

That could be family, that could be criminal, it could be land, it’s just anything. It wasn’t employment discrimination. It wasn’t employment law.

I did end up working with, or collaborating with, this other general, I mean, solo practitioner who did employment discrimination cases solely. He represented plaintiffs. So I would get some cases from him so I could just get some experience.

So for one, two years, I did that. Then I got an opportunity to work at an equal employment opportunity consulting firm. That was my first purview, or preview, into the world of alternative legal careers. That’s what I call them: alternative legal careers.

They were looking for lawyers, and they even called us attorney EEO consultants. So they were looking for lawyers, but we were not practicing law. We were consulting companies and organizations on how to comply with the equal opportunity law—Title VII, the Civil Rights Act of 1964, primarily.

I did that for like the next 12 years and found that fulfilling. But something in the back of my mind was always like, "You did not live up to the expectation or potential of becoming a lawyer because you are 'not practicing.' You have not been in Biglaw."

So throughout these 12 years of having a great job, doing good work, because I’m neutral, so that was exciting. I don’t have to represent anyone, I could just advise, counsel, and move on, but you have this nagging feeling, "Oh, maybe…" So as a lawyer, people don’t listen to you, people don’t listen regardless.

Sarah Cottrell: Yes.

Tiffany Obeng: So they come to you, seek your guidance, and then they do what they want to do. But if you’re having doubts about your potential, when someone doesn’t take your advice, it makes you feel like, "Maybe I don’t know what I’m doing. Maybe I don’t know what I’m talking about. That’s why they didn’t take my advice."

Or if you don’t know an answer to something off the top of your head—because you’ve seen on Perry Mason that he knows every single law and every single word and just everything, he’s so strategic—it makes you feel like, "Maybe that’s why I didn’t get that Biglaw job. Because I’m just not cut out for it. Because I wasn’t smart enough."

So all these doubts are coming, and it’s impostor syndrome. So as I’m working these 12 years in this alternative legal career, I still have this nagging feeling of needing to feel "successful" in the terms of what my law school and what others have seemed to put.

I go to places and I say I’m an attorney and they say, "Oh, what law firm do you work at?" Then I say, "Oh, I work at this place. That’s a consulting firm." They’re like, "Oh." Or at least that’s how it seems.

So it’s building on top, building on top. Finally, 2023, I got my opportunity to work in Biglaw, Sarah. I did.

Sarah Cottrell: Lucky you.

Tiffany Obeng: Yes. Oh my gosh. How did this—? I didn’t even look for it. Because I’m just going my way, trying to accept that I’ll never be in Biglaw. I’ll never live up to other people’s expectations of me, whether they say it or not.

Like my mom wasn’t saying, "You failed." Of course not. My husband wasn’t like, "Oh, you suck." Nobody was saying any of these things to me.

This is just me feeling it internally, not knowing what I was feeling was, one, I was not alone in what I was feeling, and two, realizing all the steps that I’m talking to you about, about how we even got to just this feeling of almost despair.

But I wasn’t sad or anything. It just seemed unfulfilled. So I’m doing something that’s fulfilling in my alternative legal career, but I can’t fully enjoy it or throw myself into it because I keep having all these doubts of "I did not achieve." So I get the Biglaw job. Girl, nine months later, I’m back out.

Sarah Cottrell: I was going to say, and it was the fucking worst. This episode will be rated E on Apple Podcasts.

Yeah. I mean, I can only imagine because, well, I mean, I think I've made my position on Biglaw fairly clear on this podcast.

But I just want to pause there because I’ve had two people recently on the podcast who are also in The Collab, Laura and Dan. Both of them talked about a very similar thing. Laura had actually been in an alternative legal career, but eventually she was like, "I feel like I'm not doing what I'm supposed to be doing because what I'm supposed to be doing is working at a law firm."

Dan also had this sense of, he talked about having this feeling that if you were a gifted kid who was told that, you feel this sense of, "I need to be achieving some great thing. I can't just have a job. It has to be the most impressive job."

Then, of course, we're all in this profession that is so dependent upon prestige and these artificial hierarchies that result in people—when you say, "Oh, I work at this place that's not some fancy law firm"—being like, "Oh, well, blah blah blah."

It's this perfect mix, this perfect cocktail, that is so toxic. It's particularly toxic for people who are that high-achiever type who learned, often, to measure their worth in terms of how much they were achieving.

Then, like you said, you put them in law school where they're all basically being ground down because they're being graded on a curve. Then throw them out into the profession that's prestige is everything, if people aren't impressed with you, you're nothing. Surprise: not great for anyone involved.

Tiffany Obeng: Right. I want to make sure I say, so yeah, I remember a short time ago, a moment ago, I said when I was at the consulting firm, and they say, “Oh, you're a lawyer. What firm do you work for?” I’d say the name of the consulting firm and they’d go, “Oh.”

So tell me why, now I’m at this top law firm in the nation. Okay. I've made it. I’m thinking, "I made it." I say, “I’m a lawyer.” They say, “What law firm do you work at?” I say the name. They say, “Where?”

Sarah Cottrell: Okay, that's actually hilarious because this is something I tell people a lot. When you're in the lawyer bubble—especially if you're young, like if you're earlier in your career, if you're in law school and you're thinking about graduating and jobs—there’s so much focus still on getting into Biglaw, the rankings of law firms, all of this stuff.

One of the things I think is so important to remember is the only people who really care about that are other lawyers. Most other people, you could tell them, "I work at whatever law firm," and it could be a top-five Vault law firm, or it could be three random people in wherever.

Most people—including highly educated, professional people—no one’s sitting around thinking, "Which firm names do I need to remember so that I know which ones are truly legit?" That's just not happening. So much of it is this internal, inside-baseball stuff that we’re doing to ourselves.

Tiffany Obeng: Right. So that nine months were really eye-opening and got me to a position here today where I can speak confidently about my journey. I can accept my alternative legal career for all that it is, and my children's book projects that I work on.

Because during that nine months, one, I learned that people don't know. Like you just said, people don’t know one law firm from another. So maybe they weren’t just saying, “Oh,” because they were disappointed in my choice of where I was working at that time. They were saying, “Oh,” because they just don’t know. They really don’t know. They’re asking, but they don’t know the answer. They don’t know what answer they’re expecting.

Then secondly, while I was working at that top law firm, I learned that other lawyers who are very smart don’t have the answers to everything. That was so enlightening. Because remember, I’m thinking, "Maybe if I don’t know the answer, that means I’m not good enough."

But no. They’re like, “I don’t know. Why don’t you talk to such and such?” or “Let’s look this up together,” or “Let’s learn this together.” I’m like, “Oh.” That is very freeing.

Then the third thing was, people still didn’t listen.

Sarah Cottrell: It doesn’t matter. It doesn’t matter where you are. They still generally don’t want to listen.

Tiffany Obeng: So I stopped accepting that or taking it on my back as something I was failing at and learned that it was just human nature. I am all the good things that people have believed me to be all my life.

Sarah Cottrell: Yeah. It's interesting because I think it's so common for lawyers, because so many people who become lawyers were kids who learned to achieve in order to earn approval. That was a way they earned praise and all sorts of other things.

The thing is, you end up in a profession that is built around this idea of getting external validation. I think for a lot of people—certainly for a lot of my clients—one of the things that they end up coming to realize is, "I cannot just make my career decisions based on what other people are going to think about me."

Even though in a lot of cases, that’s the only tool we had when we were making the decision initially. Because it’s so externally focused, it doesn’t really focus on the internal experience.

Related to the internal experience, it is so common for lawyers to do what you're describing, which is: "Oh, this feels off. The clients aren’t listening, it must be because I individually am doing something wrong." Or, "If I’m having not a great experience in my workplace because I’m working for a boss that’s abusive"—which is also very common in the law—"it must be because I’m not doing things or saying things in the correct way to avoid being treated this way."

There’s so much, because so many people who become lawyers are these highly responsible types, we basically try to take responsibility for everything. That generally results in us thinking, "There must be something wrong with me."

Tiffany Obeng: That’s exactly right, Sarah.

Sarah Cottrell: Yeah. So anyway, that’s my soapbox on that piece. But I would love to know—well, I have so many thoughts—I’d love to know when you started thinking about the children’s book thing.

If there’s more that you’d like to share about your time in Biglaw, I’m also interested in hearing that. Or if there’s something else around either of those things, that would be great too. So where would you like to go next?

Tiffany Obeng: Let’s go to the creative outlet, the bibliotherapy.

Sarah Cottrell: Perfect. Yes. Let’s do it.

Tiffany Obeng: So we’re in 2020, okay? You remember 2020. Everybody remembers 2020.

Sarah Cottrell: Yes. Seared into the memory.

Tiffany Obeng: We're at home, trying to figure out what’s next in life, trying to figure out, "Will we ever be let back outdoors?" This is March 2020—I’m not even at May 2020 yet.

But either way, along with becoming a lawyer, my mom had always instilled in me that I would be an author. So while I’m pursuing the journey of becoming a lawyer—and of course doing that first because that’s the prestigious one—in the back of my mind, I’m trying to figure out, "How is this becoming a lawyer?" Because my mommy has planted seeds and they have to grow. "How is this becoming an author going to manifest?"

Would I be a blogger? I tried blogging. Would I be a—I love movies—so would I be a movie critic? I guess maybe that’s a form of blogging, but a reviewer. What would it be?

Would it be a memoir? Will it be a self-help book? I don’t know. I didn’t have kids until my first child was born in 2015, so I didn’t even think children’s book at all.

So now we’re in 2020. I had a manuscript from probably 2018 that I had tinkered around with and put in my phone and went on about my business. My mom and my husband are like, “When are you going to write a book? When are you going to publish a book?”

I’m like, "Is it really that simple?" So I’m researching traditional publishing companies, trying to figure out, "How do you even get to publish a book?"

Traditional publishing companies usually do not just take submissions from any and nobody. You usually have to have a literary agent.

So I'm like, "I don't even know how to get that." So it just kept getting put on a back burner. But now we're in 2020, got a little bit more extra time because I don't have to commute to work. That really gives you a lot of time, not commuting to work.

Just trying to find something to take your mind off of what's really going on in this dumpster fire of a world. I come across self-publishing. So I say, "Oh, okay, you can self-publish." I'm smart. I know how to research. So I went to researching, put all that together. You know, my legal skills, one of them is researching. So I'm researching, analyzing all the information I'm getting.

I published my first children's book. Children's book, no less. It was titled Andrew Learns About Actors because my son's name is Andrew. I thought it would be cute to have that legacy with him. We both love reading. We both love watching TV and movies. He loves interacting with the TV. I love interacting with the TV.

But it made me think—because he was like four at the time—"Hey, does he realize that these characters on TV are played by actors? Does he realize that he can one day be an actor if he wanted to be?"

So that began my journey into children's book writing where I do mainly—well, not mainly, but, it will be—career books for kids. So the hope there is I don't want them to be like me or you, Sarah. I want them to be able to know what their options are in life.

If their mom or whoever says, "Hey, you should be a lawyer," they can go and pick up Andrew Learns About Lawyers and read about what a lawyer is, what a lawyer does, and what they can do outside of practicing law.

So giving them a resource guide, if you will, that's brought to them in a digestible, fun, engaging way—it rhymes, spoiler alert—where if they can see it, they can be it.

So I do career books for kids, but I've also branched off. Because as I'm publishing books, I did my Andrew Learns About Actors. Then I did Andrew Learns About Teachers because, again, pandemic. My mom was an educator before she retired, and my husband was an educator before he did a complete career pivot.

Sarah Cottrell: Yeah.

Tiffany Obeng: So I was like, "Are y’all serious about what is being required of you right now? Y’all are really trying to teach these kids virtually? This doesn’t make sense."

So I did Andrew Learns About Teachers, so he and other children can see that the people they see almost as much as they see their parents is an actual career that they can aspire to become.

So again, learning about the goods of teachers and that you can become a teacher as well. Just putting that thought in their mind.

So as I'm getting deeper into the publishing world, I realize there is a severe lack of diversity in children's books. So at first, it's putting my son's face on it because that's my son. He's a Black kid. So that's how it ended up being a Black character, a Black boy character. It wasn't thought through.

But once I learned of these statistics, I'm like, "Hold on. I have the ability to adjust these statistics. So I will adjust these statistics."

So over the course of the next 10 months, I wrote and published eight more books. They were about honesty. There's rarely any—if any—honesty books that feature a Black child just going around the house, breaks the lamp, now he's trying to figure out, "Is he going to tell the truth or tell a lie?" Like universal themes, we're lacking that.

I wrote seasons books. The first one was Winnie Loves Winter. She loves winter. She wants everybody to know about winter.

Because I have an educational back—well, I don’t have an educational background—but I’m a lawyer. So teaching is something that I want to teach others.

So it’s like you're going to be inspired, but you're also going to learn. So she's going to have the fun facts about winter and why she loves winter.

Just so many more books—sportsmanship books—just so many more books that explore universal themes but showcase our characters. So then it did become intentional.

The career books for kids are intended to, again, expose children to their future possibilities. We have diverse images in there so they can see themselves in the characters. We have little nods to Black history or women's history.

So again, they can see that it's been done before. So if it's been done before, they can do it as well. I'm just really trying to influence the school-to-talent-pool pipeline, which is what I call it, instead of—and dismantle, hopefully—the school-to-prison pipeline. I'll stop right there just in case you had some questions.

Sarah Cottrell: Well, I was just going to say so many things. First of all, I think, especially if you have worked in a career like lawyering where there is still a ridiculous lack of diversity, especially when we're talking about some of these institutions that law students are pushed to go into out of law school, I think it's a very visceral reminder of, I know this is going to sound super cliche, but representation matters. And I see that at all levels. But to your point, even when we're talking about kids' books, because publishing as an industry is possibly even less diverse in terms of what it publishes than the legal profession is in terms of the constitution of its organizations or institutions. In order for it to be changed, we have to intentionally work to change it.

So first of all, I love everything that you were talking about in terms of the goals behind what you're doing. But I’d also love to know, can you talk a little bit about the timeline?

Because I know you said you wrote like eight books over 10 months or 10 books over eight months or something. So I think for people who are like, "Oh, this sounds cool. I wonder what it looks like in the day-to-day," could you talk a little bit about that? People are like, "It looks like a dumpster fire, Sarah."

Tiffany Obeng: Yeah. They're like, "How did you do that?" I'm like, "I don't even know."

So I'm currently at 25 books and coming up upon five years. What I tell people, because again, I am still a full-time employee, I am a mother to two small children, I am a wife, still, I want self-care as well, so at the time when I did 10 books in eight months, I was very inspired. This is now after I learned the statistics. George Floyd had occurred. It was just like, "Oh my gosh."

My son, he had gone to school. One of the books I did during that time, my son had gone to school and a girl teased him about his curly hair. So I wrote a book called Black Boy Hair Joy.

During that same summer, my son would come home from school and his skin was getting darker, of course, because he's playing outside all day. Me and my mom kept commenting like, "Oh my gosh, we know you've been outside today. Oh my gosh, you're getting darker."

Then I said, "You know what? Why? Why are we passing this down generation to generation? We're going to reframe this conversation." So I wrote My Summer Skin Is Radiant.

I have my little tagline of, "If your kids had fun this summer, their skin should show it, but of course with sunscreen."

So just having something to say and having a reason to say it. Even if it wasn’t—those are the only two, I don’t know. I don’t want to say Black-focused books, because what I found with My Summer Skin Is Radiant is that different cultures, Hispanic culture, love it. They’re like, "Oh my gosh, we got to get this for little [inaudible] because [inaudible] be tripping when it comes to skin tone."

People who are from the Indian culture, they love it. So people of different cultures like the idea of My Summer Skin Is Radiant to dispel and rebuke the idea that darker skin is not beautiful.

So it’s like, "Our skin is beautiful all year long." That’s another one of my taglines. But how did I get it done? Yeah. I just think I was really pushed.

So any opportunity I had, we were in a car when I wrote My Summer Skin Is Radiant. I was on the passenger side, and that thought came to my mind. So I pulled up my Notes app and just started writing, writing, writing.

As I tell people, I just write on the go. I did Black Boy Hair Joy. I would think of lines, it’s written to be like a rap because I want Black boys to want to read it. So it's like a little rap or whatever.

My husband was laughing at me as I was trying to be cool. I'm like, "What are the cool slang terms where you can go days?" I'm going on Facebook like, "Hey, mom and dad."

Sarah Cottrell: What is Gen Z talking about? What is Gen Alpha talking about? I don't know what's going on."

Tiffany Obeng: Yes. I'm like, "They say 'slap'? Okay. 'Gucci'? Okay, Okay, let's go."

Sarah Cottrell: Oh, my gosh. I'm laughing in elder millennial. No, excuse me.

Tiffany Obeng: He was like, "I can't believe you're doing this." I'm like, "I'm doing it. Buckle up, okay? Get on board."

Sarah Cottrell: It's happening."

Tiffany Obeng: So I did that walking to, like, getting in the bed, I'd be like, "Oh, that's another rhyme I can do. Fades, or I'll talk about fades and I'll use this type of lingo to go with fades or whatever." So I’ll put that in my Notes app.

Then maybe during my lunch break or maybe right after work, I'll log off my work computer. Because now I'm back in my, or at the time I was in my, alternative legal career. So I had the ability to log off at five o’clock during that nine months when I was at the law firm, the top law firm. I mean, I could log off if I wanted to, but the work was still there.

Sarah Cottrell: Yeah, yeah.

Tiffany Obeng: Like, it was never-ending. So it really made it hard for me to work on my children's book during the time I was practicing in the law firm, which was another reason why I was like, "I need that outlet." So that was another reason why I just was like, "You know what, this is not worth it. I'm going back to legal-adjacent careers."

For me, work-life balance was very important. So just finding those times to do it, it does feel like you're, sometimes you do, especially as a mom, you have guilt because you're like, "Okay, I'm sitting in my office," and my kid might come in here and be like, "What are you doing?"

It's like 7:00 PM, they're like, "What are you doing?" I'm like, "Oh, I'm just working on this book right now." "Oh, well, can you come play with us?" It's like, "I want to get my book done," but then I can play with you after. Or going to events to market and sell my books, that takes a lot of time out of the day and away from your family. So it does get hard.

But I do have a supportive family. My mom supports, she'll come and watch the kids if I need my husband to come with me. My husband, of course, sits at home with the kids if I'm just going by myself.

So it just takes a village. Because I have such a supportive family, making it happen is a little bit easier. And you have to have a team.

So if you're publishing—it's called rapid publishing—if you're publishing rapidly, you have to have a team of editors. You have to have a team of formatters, a team of typesetters.

If you're doing children's books, you're going to have to have a team of illustrators. Otherwise, you're going to get stalled.

So that's how I did it, with a team, with support from my family, and just the unmitigated gall.

Sarah Cottrell: Perfect. I mean, okay. So I have two totally different directions that I want to go.

First thing that I want to say is I really love that one of the things that you're doing is like, I can't remember what you said, but you're publishing books that have representation but some are more specifically talking about something specific.

So, like, for example, the summer skin thing. But then a lot of them are just, like, books. Because—if people only listen to me, they may not know—I am white. My kids are white.

But one of the things that we’ve really tried to do is to find books that are not just all white kids. It is actually very difficult to find books that are diverse that are not designed to be talking about that specific thing. Does that make sense?

Tiffany Obeng: Yes.

Sarah Cottrell: Like, to your point, I think publishing is doing better than it used to, but it's still not great in terms of the ways in which the things that are treated as a default, I guess, is what I'm trying to say.

That, I think, is not good for kids. Because they should be able to see lots of different kids in lots of different circumstances.

Tiffany Obeng: In everyday normal situations.

Sarah Cottrell: Yes, exactly.

Tiffany Obeng: Which is one of the pillars. So the three pillars of Sugar Cookie Books—that's my publishing company—are: inspire, educate, normalize.

So my hope is that if you see enough kids in children’s literature, for example, just doing the same things as other kids, then you would see them as human. You would see them as normal. Hopefully, the world would be a safer place for them.

So I'm like that little pebble that you throw in the water that I'm hoping would have a lot of ripple effects.

Sarah Cottrell: I love that so much. When I got your email and I read what you're doing with this company and why, I was like, "Yes, please. Podcast immediately."

Tiffany Obeng: You did. You did. I was like, "Oh, my God."

Sarah Cottrell: I know. I was like, "She's going to think I was just like waiting by my Gmail inbox, just like waiting for her email." I was not. It's just like as soon as I saw it, I was like, "Yes."

Tiffany Obeng: Thank you.

Sarah Cottrell: 100% yes.

Tiffany Obeng: Thank you for not playing hard to get.

Sarah Cottrell: Other thing, which is to go back to something that I think would be interesting to talk about. You talked about having this sense of, well, before you went to Biglaw, "I didn't get to Biglaw. So I haven't done the thing that I'm supposed to have done because that's the pinnacle."

That's come up with other people on the podcast as well who have had that driving them in their career. Then often, get an opportunity to make a move and then are like, "Was this actually—did I actually—is this really what I want to be doing?"

So I’m wondering if you could talk a little bit to the listeners, because I’m sure there are many people who are listening who have the experience of going to law school and being like, "I’m a super smart kid. But I’m a super smart kid amongst lots of other super smart kids."

So I feel like I’m sort of the middle of the pack. And the same thing with wherever they’re ending up career-wise. I think there are a lot of people who have this sense of "I still should be trying to get to that one specific brass ring that law school basically told me was the thing that would prove that I really made it."

Can you talk a little bit about that, how that was for you in terms of maybe to what extent and how quickly you had this realization of, "Maybe that wasn’t actually the full picture or fully accurate"?

Tiffany Obeng: Girl. I mean, again, I wish your podcast and other podcasts like yours existed before. Because when all you hear is Biglaw—Biglaw is the brass ring—and you fall short of that, don't get into Biglaw for whatever reason, then I think for me, I was still chasing it.

I might not have been actively pursuing it, like, I wasn’t applying to Biglaw all day long. I even told you guys that the Biglaw opportunity came to my doorstep. I was just minding my business and it came to me, and I was like, "Oh."

So I just wish that it would have come sooner. So it could have been out my system and I could have been more confident sooner. I could have been walking in my purpose and passion more boldly sooner.

So I just hope that whoever is listening, I can’t say that you’re going to just wake up and be like, "Oh, I didn’t." If you want that Biglaw, if it’s instilled in you or you’ve heard it or it’s been ingrained like, "This is what success looks like," I do emphasize a lot, whether it’s in publishing or in law, you define what success is for you. You have to be comfortable with what success is for you.

That’s what I was doing to cope with "not reaching" other people’s level of success. Like, okay, well, I’m not at Biglaw, but I do have a fulfilling job where I am making an impact, and where I make really good money, and probably better money than people who are practicing law.

So, like, they may not know the place when I say that I work at this place. They may not know it, or they may get confused as to how I'm a lawyer but I’m not working in a legal position. But that's success for me.

I'm doing what I like. I have work-life balance. That’s success for me. I make a well living. That’s success for me. I have a boss who is supportive.

Although the job that I have did not require a JD or a legal license, she encourages me to use my JD and legal license. She gives me opportunities to use it—not in a way where it's practicing law, of course, because that would be a violation—but like, "Hey, you are great at writing. You are great at analyzing. So, hey, we have this new legislation coming in. Can you do the comments on it? Can you analyze and comment on it?"

She’s not intimidated. Because I have been in alternative legal careers where my bosses were intimidated by me and others having legal degrees. It's like, "Well, why do you hire us if you don’t like it?"

So defining your success for yourself and knowing that, I hope us joking, seriously joking, about how lay people really don’t know what lawyers do, one, or two, what law firms, they don’t know a Biglaw.

So even if you ended up in "a small law firm," they’re still going to have the same reaction no matter where you said you work. So I hope that really stuck out to people.

Sarah Cottrell: Yeah. You're destroying your quality of life to impress, like, the gunneriest gunners on the planet.

So like, if that feels fulfilling for you, that is super great. If it doesn’t, then there are lots of people who share that feeling. A lot of them are in the Collab.

So one other thing that I just wanted to bring out from what you were saying about your experience is that often when I talk with people and I’m working with them, there is this sense—especially if they’ve been in law firms for a long time—of, "This sucks, but this is just what it is to be an adult with a job. It wouldn’t be better if I went somewhere else. The tradeoffs wouldn’t be worth it," etc.

Now, obviously, as you talk about your story, it’s very clear that that is not true. But I just wanted to basically ask you to reemphasize that, because I very frequently am talking with people who have been given this sense of, "This sucks, but it can’t possibly be better."

That’s just not accurate.

Tiffany Obeng: Yeah. So because I knew where I was going, I essentially boomeranged. I'm a boomerang employee. So I left the job that I was working at to go to Biglaw, then went back to the job that I left.

So they joke about, "Oh, you were just on sabbatical." So anyway, I knew where I was going back to, and I knew what I liked about the place I was at. And I knew the type of work that I was going to be doing. I didn't go back to the same position, but I went back to the same place. So that helped.

But for anyone who's listening, there are opportunities to have a fulfilling legal-esque career. There are more options than just practicing law and whatever you think practicing law looks like.

Like for me, when I was practicing law at that Biglaw firm, it wasn’t going to court. My practicing law was responding to position statements and engaging in mediations. So that’s what my practicing law looked like.

But there are so many opportunities, and there are so many other positions that appreciate people who have that JD, people who have those skills that you learn. It’s always in some type of—not always—but a lot of compliance positions appreciate people with that legal background.

We have institutional compliance, corporate compliance, Americans with Disabilities compliance, Title IX compliance, Title VII compliance. There's a lot of opportunity to still utilize your skills that you paid for in a meaningful way that can also afford you a workplace that you enjoy going to, being a part of, and feel supported in, and still make good money.

Sarah Cottrell: Yeah. It's not imaginary.

Tiffany Obeng: No.

Sarah Cottrell: Okay, Tiffany, as we're getting to the end of the conversation, is there anything else that you would like to share with the listeners that we haven't talked about yet?

Tiffany Obeng: Let's see. Work-life balance. If that's important, I think that's becoming more and more important to people. That’s good.

I just wonder, "How did we live pre-2020? What was going on?" Us driving hours to get to work and things like that.

Our legal skills are transferable. I do want to reemphasize that. Our legal skills are transferable, whether you want to do a compliance job or be a caterer. I don't know. But the legal knowledge that you have will transfer.

My legal knowledge, I apply day in and day out to my children's book business. People often compliment me on my ability to relay complex information to children in a way that they can understand, in a simple and engaging way.

They’re like, "You're able to break down these topics in a way that is easy, that is digestible." At first, again, because I had my doubts, I'm like, "Oh, I don't know what they're talking about." But now I'm standing in the sun, and I'm like, "Yes, that's because I paid a handsome sum of money to develop this skill."

So just leaning in on what skills that you had that you probably polished in law school and figuring out—I'm sure that's what you do in your Collab when you help others—but figuring out what skills you have and what passions you have. Because happiness is not fleeting and it can be created.

Even if it’s not—so say you stay in practicing law—but you can do something that you’re passionate about. Many people ask me, "Will you ever quit and just do books full time?" They clutch their pearls when I’m like, "I don’t think so."

So they're like, "What?" I'm like, "Because I love having the flexibility and I love having the passion. I don't want to have to conform. I don't want to have to lose my messaging. I don't want to just be like having to make money from a book, so therefore I'm cranking out stuff that I really don't care about."

I do now have a literary agent. What that means is that I have that conduit that I submit manuscripts to her, and she'll send it off to traditional publishing companies for their consideration and hopefully offer.

So I do have that. But she's allowed me to keep my independent arm. She's like, "I love what you're doing independently. I don't want to step anywhere in that. But if you have other manuscripts that you don't want to publish through your company, please let me know and we'll work on it."

So just those opportunities come when you just try, when you just step out. Opportunities that you didn’t even think of will come about. So I just hope that you guys will listen to Sarah. Seek Sarah. She knows what she's talking about.

There are way more lawyers out there who feel the way that you feel, that you didn’t know about. But now Sarah is making sure to amplify and spotlight that you're not alone.

Sarah Cottrell: Yeah. I was just going to say, on the point about happiness, I think a lot of us—well, I'll speak for myself—I think for a long time, I, and definitely this is something I internalized when I was young, that "you shouldn't focus on your happiness."

"You can't just care about being happy, because if you make all your decisions based on what's going to make you happy, then you're probably going to make a lot of selfish, irresponsible decisions that are bad for you and bad for other people and blah, blah, blah."

As a kid who was—and a person in general—who's extremely intensely empathetic, obviously that was important to me. So I internalized it.

I think this is true for many people being lawyers. It’s like, "I shouldn’t think about happiness when I’m thinking about my career or what I’m doing with my life." It’s accurate in the sense that if that is the only thing, if that is the only value, divorced from anything else, that is guiding your decisions, they are probably going to be imbalanced decisions.

But I think so many of us who became lawyers because of a constellation of factors are like, "I’m not going to think at all about whether or not this makes me happy," or even contemplate that you could make decisions that incorporate thinking about, "Is this going to result in happiness?"

I think that if you're someone who's like, "Wow, this is really not working for me," that one of the things you do need to get back in touch with, to your point about passions, is like, "What would actually be fulfilling for me? What would actually make me happy?"

I'm not saying that means quit your job tomorrow to do the thing that you think is going to make you happy with no groundwork and no legwork and whatever. But it matters. It matters.

You certainly are not going to end up in a place that makes you happy if you're actively running away from being aware of what that even is.

Tiffany Obeng: Yep. Yep. Yep. I do want to—I know we have to close out—but Sarah, I want to say that to one of your points you had made, which was you seek diverse books even though you yourself and your family are racially white. I so appreciate—I wanted to make sure I said this—I appreciate you for doing that.

Because one of the challenges that I face, and other people who write books with Black main characters, for example, is that people tend to think, "Oh, that's just a Black book. That’s for Black people."

And it's like, no. That’s why I want to emphasize, I do universal themes—except for maybe the one or two books—but my books are universal themes. It's not just Black people. It's Black people doing universally—I don’t want to say acceptable—but universal things.

So that was very intentional of me to make sure I’m putting them in places that are universal and relatable. For you to understand that, yeah, just because it has a Black main character doesn’t mean it’s just for a certain group of people, I really appreciate.

Because there are privileges that exist in children’s literature, where if it has a white character, then it’s everybody’s book. But if it has a minority character, then it’s just that minority group’s book. And don’t even get me started on if it has a boy character on a cover.

Sarah Cottrell: Okay, yes. And so I’m just going to say to all the white parents out there, and grandparents, and—I don’t know—aunts and uncles of white kids, you need to actually look for these books yourself.

Because if you just buy whatever random thing is the main thing pushed by the traditional publishing houses, your kids are not going to be seeing diversity in their books. It’s just not going to happen.

You have to actually be intentional. Yes, the publishers have a responsibility. But also we, as the buying market buying books for our kids, have a responsibility—particularly if you are a white parent in the United States of America in 2025—to make sure that your kids are not just reading books with characters that look like them.

Tiffany Obeng: Thanks, Sarah.

Sarah Cottrell: Okay, that's what I have to say about that. Tiffany, can you tell people where they can find you online, your company, etc.? What do you want the people to know?

Tiffany Obeng: Sure. So again, the company is Sugar Cookie Books. Sugar Cookie like the actual cookie. Books with a plural.

You can find me across multiple platforms: Instagram, Facebook, LinkedIn. My website, sugarcookiebooks.com, @sugarcookiebooks. I also have a tiffanyobeng.com.

So if you're like, "I don’t know what she said about sugar cookies," but you see my name, tiffanyobeng.com, will also get you to sugarcookiebooks.com. @sugarcookiebooks everywhere.

Sarah Cottrell: Cool. Awesome. We will put all the links in the show notes and the blog post and all of that.

Tiffany, I really appreciate you reaching out to me and coming on the podcast. I think this was a really good conversation, and I’m excited to share it with people.

Tiffany Obeng: Thank you for not playing hard to get and responding to me.

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.