Is quitting law without another job lined up a bad idea? with Andrea Yang (TFLP 050)

When you’re super miserable in your job as a lawyer (been there!), you often find yourself wondering: can I just quit? Is quitting law without another job lined up a bad idea?

Some jobs really just are that bad. It’s not uncommon to find yourself in a place where continuing to work as a lawyer is just too awful for your mental or emotional health for you to continue.

My guest on today’s podcast, Andrea Yang, is a lawyer who quit her job without any other job lined up. Not only that, when Andrea quit litigation seven years after she graduated from law school, she moved back in with her parents to give her some time to figure out what was next for her.

Is quitting law without another job lined up a bad idea?

Maybe you can’t imagine being so miserable in your job as a lawyer that you would be willing to quit without another job lined up.

But for Andrea—and for many of us—this level of daily misery was (or is) a reality.

Law school was the path of least resistance.

Growing up with immigrant parents, Andrea assumed that she would be a doctor. In her mind, there were only three career paths: medical school, law school, or business school.

When she arrived at Harvard for undergrad, she realized that she didn’t really like her math and science classes, so medical school was out. She didn’t have enough credits is business and econ classes for business school, so law school it was!

“Law school was the path of least resistance,” Andrea told me. And she would continue to engage in this type of “unconscious decision-making” for the next almost decade.

Her fancy law firm job quickly lost its shine.

Andrea graduated and got a fancy job at a big law firm, but quickly realized that she detested it. An unexpected opportunity to clerk for a former partner at her firm who had been appointed to a federal judgeship arose and she jumped at it, hoping that she would figure out a better path.

That clerkship led to another clerkship, and she didn’t have any more clarity than she had at the beginning. As her second clerkship was coming to an end, she decided to take a job at a firm in Seattle, because she really loved the outdoors and could be close to multiple national parks.

Within the first week of starting her Biglaw job in Seattle, Andrea knew it wasn’t going to work out. She felt like she needed to stay for a year “for her resume” (although now thinks that’s a completely arbitrary rule that provide a convenient excuse for avoiding pursuing what you really want).

When the start of Andrea’s second year at the firm rolled around, she didn’t have any more clarity about what was next, but it was becoming increasingly apparent that she was utterly miserable.

Quitting law without another job lined up was the solution for Andrea.

Andrea called her parents and asked if them if she could move home if she quit her job. They said yes, and Andrea quit her Biglaw litigation job with no idea what was going to be next for her.

With time and space, Andrea was finally able to figure out what she really wanted to be doing with her life. She was able to do the inner work necessary to move forward in the way that was right for her. She got a job as a career counselor at Pepperdine Law, and coaches people individually as well.

In this episode, Andrea shares about:

  • A question to ask yourself: how much is the way that you’re living now costing you, and how long are you willing to put up with that?;
  • The relief of being able to be her wherever she goes, and not having a separate work-self to maintain;
  • OPOs (other people’s opinions) and how to deal with them;
  • Spending most of her non-working time as a lawyer just trying to recover from the strain her job put on her, with little time spent actually feeling like herself;
  • Why you can’t compartmentalize “work” and “not work”;
  • What she did to land her next gig (from the NALP jobs board!);
  • How hard it was to let go of the prestige-focused mindset that she had made all of her previous decisions with, and the role she thinks that ego should play in your decisions;
  • “I am so much more than just my job. A job is just a thing I do—it’s not who I am”;
  • why changing jobs is about so much more than changing jobs; and
  • much more!

Connect with Andrea:

Mentioned in this episode:

TFLP 050: Is quitting law without another job lined up a bad idea? with Andrea Yang


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 left the law behind to find careers and lives that they love. Let's get right to the show. 


Hello, everyone! This week on the podcast I'm sharing my conversation with Andrea Yang. 

Andrea was a litigator and she was so miserable in her job that she finally decided she just needed to quit and she moved back in with her parents for a few months to figure out what she ultimately wanted to do. So now Andrea works in the Career Services Office at Pepperdine Law. She's a career counselor for the students there. She also has her own coaching business.

And we talk about a lot of really important things including one that I hear all the time, which is, “If I'm super unhappy in my job, and it's a really terrible situation, how bad is it to leave before the year is up?” So if that's a question that you have, this is the episode for you. 

Before we get into it, I wanted to mention that if you're listening to this episode the week that it comes out, this week a new cohort in the Former Lawyer Collaborative starts, and there's still time to join us if you are interested. For those of you who don't know, the Former Lawyer Collaborative is my signature program for lawyers and it helps lawyers who are unhappy in their jobs figure out how to ditch those soul-sucking jobs and trade lawyering for a better life. 

There's a whole process that you walk through with structure. We have monthly office hours, group calls, we have at least one new workshop or Q&A or panel a month. So if you're interested in joining us, go to and you can get in this week. The month that you join the Former Lawyer Collaborative, you also get complimentary registration to that month’s What's Next Intensive, which is happening on Thursday, from 8:00 to 10:00 Eastern. 

That's all for me for now. Let's get to the conversation. 


Hey, Andrea, welcome to The Former Lawyer Podcast.


Sarah, thanks so much. I'm so glad to be here today.


I am so excited to talk about your story. Let's get started with you introducing yourself to the listeners.


Sure. My name is Andrea. I am a former litigator turned career counselor and coach. As a counselor, I work with law students at Pepperdine University helping them find fulfilling jobs during and after law school. And as a coach, I partner with lawyers and other professionals who want to reinvent themselves. Together I help them uncover what their life purpose is and to connect that purpose with what they do in the external world so that they feel more aligned, grounded, and empowered in their everyday life.


I love that. Let's start from the beginning, as we always do on this podcast, and talk about how you decided to go to law school in the first place.


Yes, the very beginning. “Back in the day…”

And you know, it's funny, I decided to go to law school, honestly, it was the path of least resistance. I was an English major. And growing up with immigrant parents, it was always sort of just assumed that I would go to med school. And I realized in my first year of college, that the math and the science classes, I could do them fine, but it wasn't natural, and it wasn't fun. And so I thought, “Well, clearly med school is out.” 

And at that time, I thought there were only three paths in life: med school, law school, and business school. Which is completely untrue, turns out, but as I was graduating, I didn't have the credits to apply for med school. 

And so I thought, “Well, I've taken no econ courses whatsoever in preparation for B school. So I guess I'm going to law school,” and, you know, it's funny because at my college it would seem like that's just what everybody did, if not that, they went into investment banking. And I just thought, “Well, I guess that's it, I guess I'm just gonna go be a lawyer.” 

So that is actually how I ended up in law school: completely by default, completely through unconscious decision making. And that ended up kicking off multiple years of continued unconscious decision making through multiple career pivots here and there.


You know, that's such a common story, and it's interesting because it's come up recently, a couple times, specifically in my conversations on the podcast about people sort of being raised with this idea of, essentially, you become a doctor or a lawyer or maybe go to business school, and pretty much those are the options. 

What do you think... Because not everyone is necessarily raised with that sort of thinking. But many people who end up in law school, from my experience, grow up in families where that is sort of the narrative. Why do you think that is?


You know, my parents came to the US in the 80s, from Taiwan, and really they were, I think, just trying to figure it out as they came. And there really was this narrative that there are certain paths in life that are more “secure.” And I think in terms of med school, it was just being a doctor, it was just this established profession where you have that prestige and that security, the financial compensation that goes along with that. That was just appealing. 

And, you know, really they came here with not very much at all. And so what they wanted really was just the American dream for me and my two siblings. 

And so I think in that sense, like so many of my decisions up until fairly recently, in the last several years, it has always been pretty risk averse. It's always been, “Well, what are most people doing?” 

And because I think when you have the templates of other people and the majority of people, you see what multiple outcomes are, and you're kind of like, “Oh, well, you know, if those were the outcomes that happened for them, they'll probably happen for me too.” And so it looks like in the external world, they've got it all going on. So, you know, why not do that?


Yeah, and I'm sure there are a lot of people listening who will relate to that thinking and even that risk-averse approach to life. 

So tell me about when you got to law school. Did you get to law school and you were just like, “This is awesome! I'm super excited! And everything about this is great.” Or were you sort of like, “Well, I'm here because this is what I'm supposed to be doing.” What was your outlook when you got there? And how was that experience for you?


You know, it's funny, I remember my first week of law school, I was so paralyzed, and terrified and overwhelmed. And I remember thinking with that first week, I honestly felt like I was learning how to read again, just because with case law, it's a completely different structure from the regular narratives that we see in media and certainly the texts that I was used to as an English major, that it just felt like a new language, first of all. And I think a lot of people have that experience.

Then it became clear to me over the three years, the environment I always thought was unnecessarily competitive. I hated being called on in class. The Socratic method was not my strong suit at all whatsoever. And I just thought to myself, like, “Why? Why do we have to learn in this way where we're basically just singled out, and in a really aggressive manner?” And you know, for me, harmony is my biggest strength. And I love helping people feel comfortable, and I love feeling just comfortable and at ease wherever I go. And so it really was the antithesis of how I am actually wired as a human. 

I remember in law school, academically, what I enjoyed the most was my legal research and writing class. And that was because, I mean, it was the research and writing. I was used to that and I was good at it. And it also didn't have the pressure of being cold called on in class and it was a more collaborative environment. 

And I also remember too, really my favorite experience in law school, it actually had nothing to do with the classes whatsoever. I was a resident fellow in the dorms my third year of law school where I basically planned fun events for the 1Ls and the 2Ls that lived in that building, and as a peer advisor, and just basically created that comfortable environment, especially during moments of stress, whether it's during finals or whatnot. But I remember having a lot of fun with that. 

And it's interesting, because what I do right now at Pepperdine, there are a lot of parallels to that experience as an RF. So, yeah, when I think about law school, the highlights really were being that resident fellow in the dorms. 

And I liked my clinic experience because it was very hands-on and practical. I learned through actually just doing. Theory alone doesn't do it for me. So it was it was nice to see that, you know, “Okay, everything I'm learning in the classroom, this is how it can be applied. This is how I can actually concretely benefit a client who otherwise would not have access to these legal services.” 

But other than that, you know, it really... It wasn't an overall fun, enjoyable experience for me.


So when you were graduating and heading into your first legal job, it sounds like maybe you're glad to be done with law school, and were you thinking, “Now I'm going into legal practice and it's going to be great”? Or what was your perspective on what you thought legal practice was going to be like for you?


You know, I think I had high hopes in the sense that, you know, for my clinic experiences during law school I liked the practical application of what I was learning. And I thought, “Well, you know, hopefully practice will be better because we're working with clients for real.” 

So in that sense, I was excited about it. I was excited about my first grown-up job with a grown-up paycheck that came with it. And I think, too, you know, I started out at a big firm doing intellectual property litigation, mostly patent litigation. And I think there was a big part of me that was just like, “Gosh, that's fancy. I’m fancy!” [laughing]


[laughing] I totally understand what you're saying.


Yeah. So I think that high, it lasted for a little bit, but it was quickly tempered by the fact that much of my initial work as a junior associate, I did a ton of doc review! I was mired in discovery disputes, which are just, I find them really trivial. I mean, they're important in some ways, obviously, but for me, they just... They did not engage my heart whatsoever. And that is actually the greatest source of my power. It's my heart.


Yeah. And it's… I think that you have to have a very particular personality to really enjoy the discovery squabbles.


Let me know when you find somebody who actually enjoys discovery!


Yes, yes, I think you probably have to be a little bit of like a special unicorn. 

So it sounds like you got into legal practice and you had high hopes, which I totally understand. I had a very similar experience. And then it also sounds like pretty quickly you were like, “Mmm, this might not be so great.” 

So tell me, for you was it... Did you go immediately to like, “Oh, I don't want to practice law”? Was it sort of like, “Oh, maybe it's just this place”? Talk to me about the progression that took you from being at a sort of fancy firm in your fancy job to where you are now, a very different non-practicing job.


Yes. Well, the path has been very convoluted. Right after that first job at the law firm... I mean, truly, my life has been just a turn of different coincidental events that happened at the right time for the right reasons. 

I was finishing up I think it was my third year of practice with the firm when one of the partners I was working with, we were just checking in with each other and he's like, “How's your experience going so far? How are you liking it?” 

And I just said, “You know, honestly, I'm not doing very much research and writing and that's actually what I really enjoy.” 

And he said, “Well, would you be interested in clerking? One of the former partners who used to work here is a federal judge in St. Paul.”—I was in Minnesota at the time—“She's currently hiring.” 

And I said, “Who is it?” And he told me, I was like, wait a minute, my summer associate classmate—he was actually my officemate, during my 2L summer—was her current clerk. And so I messaged him, and he's like, “Oh, yeah, she's hiring, you should totally send me your stuff.” 

And so that's how my first clerkship fell into place, completely by chance. 

And I was so fortunate and grateful for that experience. And it's funny, because I was with that judge for just over a year. And towards the end of the clerkship, she's like, “Well, what are your plans?” And like, “Yeah, I probably should think about that.” [laughing]

She said, “Well, you know, one of my friends was just selected as a new judge in the district, would you be interested in working for her?” And I said, “Sure, that sounds... I'd love to connect with her and see if there's a good fit there.” And that ended up leading to the second clerkship and so that was completely, truly by by chance. 

And it was a wonderful experience. I learned a ton. I mean, I truly think when I look back on my legal career, my time clerking was the most interesting, it was the most meaningful. And it was also the least antagonistic because, of course, when you're working for the court, as you know, everybody's really nice to you, because they hope your boss will rule in their favor. 




So all of the adversarial nature of litigation, that so vexed me in practice, it really became a non-issue. 

So after a time—gosh, that would have been in 2015 when I was finishing up my second clerkship—again, there was the question of, “Oh, well, what are your plans afterwards?” And I said, “Gosh, I probably need to think about that!” [laughing] And after that, I had been in Minnesota for five years and... I love the state, by the way, it was exactly what I needed after spending my entire life before that point on the East Coast.

But I also… So here’s the thing, I love national parks, I love being outside with the great outdoors. And I really think the greatest scenes and landscapes—in my completely unbiased opinion—is on the west coast. So I thought, “Gosh, I really want to live on the west coast.” And by that point, I was like, “Well, you know, where would I want to go?” I mean, there are also only so many states on the west coast. 

But Seattle came up for me because, first of all, there are three national parks just outside of Seattle, in fairly close distance. And one of the women I connected with back when I was living in Minnesota, she was a partner at my last law firm. And the first time I caught up with her, she said, “Oh, you're probably looking for a new job! Would you want to work at my firm?” And I remember that conversation where I basically said like, “Oh, no thanks. [laughing] I actually don't think I want to go to another law firm.”

But then a couple months passed, and I was like, “Wait a minute, I actually need to find a job. And if I really want to move to the West Coast, I need to find a job.” And so I went kind of, like the tail between my legs. I went back to her. And she was so gracious. And she ended up connecting me with one of her associates in the Seattle office. I ended up interviewing with that office, and it just all sort of clicked into place. 

And that's how I ended up working at my second law firm, which overall was a good experience. But I think at that time, I was like, “Well, you know…” I was willing to try it out because I thought, “Well, maybe it was just a matter of trying out a different firm, trying out a different environment, trying out, you know, not IP work.” 

And so that's really what prompted me to go into the second firm, kind of with less of the idealistic view that I'd gone in with, as a first year associate. It had been tempered a lot by then. But nonetheless, I really wanted to be in Seattle for the parks. And so it was kind of like, “Well, I'll take the job so that I can be close to my National Parks.”


So you get to Seattle. You took the job, maybe not 100% because it was like, “This is the job for me,” and more like, “This is the job that's going to serve the interests that I currently have.” 

Tell me how long you were at that job. And it sounds like you went into it knowing, like, “This is probably not the job for me forever.” So were you always looking for an exit? Or did you decide along the way? Tell me about that process.


Well, let me tell you about my first week. [laughing]


Oh, yes, please do!


On my first week of the job, I realized that it wasn't gonna work out long term! Because I remember my first day, at the second firm, it was around five o'clock. And I had a beautiful view of Mount Rainier. I don't even know what floor I was on, it was high up, and the window panes, they were so big. And all I could see, it was just the ice-capped Mount Rainier and all I wanted to do at five o'clock was go outside and ride my bike. 

And I knew as I looked around the office, that that was not going to happen because everybody was still working. And I knew that they would still be working for a couple more hours, and then they'd probably take their work home and continue working after that. It was actually on that first week that I thought as I looked at that beautiful view and my inability to go ride my bike that it was not gonna work out. 

But you know, I kind of told myself, “Well, for purposes of your resume…” lol that phrase right there. I thought I needed to stay at that job for at least a year just so it looked presentable on my resume. That's kind of what got me through that first year because I was like, “Okay, I just have to make it for at least a year, and then we'll figure this out.” 

And then of course, that year came, and then I was like, “Well, now what? Because the year is here, and theoretically, I could go do something else. But I'm still here.” 

So, you know, my second year at the firm, it really was, it was tortured. And I remember at that time, there was this one moment where, well, there are a couple of moments that come to mind where I was like, “Oh, this is just painful.” 

But one of the moments was, you know, with these firms, they have these really beneficial trials, like fake trial programs, where you go do a fake trial with a fake case. But I remember when I got the email from whoever was coordinating it, my stomach dropped because I did not want to go through a fake trial, because I knew it was going to be antagonistic. Even with just... They're your co-workers that you're going up against, but everybody gets really into it. 

And I just thought, “This is going to be so much time, I’m not billing. And I don't even like doing this!” So I remember I think I might have made it some, like conflict, I don't know. But I didn't end up going and I was so relieved. So that was one thing that kind of caught my eye at that time.

And then I remember—actually, it was around this time of the year—this would have been in 2017. But around this time of the year, there's a wonderful tulip festival that happens just north of Seattle by about an hour and a half in Skagit Valley and like I told you, I love nature. I love flowers. 

And I was at a deposition with some opposing counsel from some fancy firm. I don't even remember what firm it is anymore. But at the end of the deposition, I said, “Tim”—I can’t remember if that’s his name but I think it was Tim—“Tim, what are your plans after this deposition? Are you gonna find a place to eat? Or do you have time to just relax?” 

And he said, “What?” 

And I was like “Yeah, you know, if you have time, there's a wonderful tulip festival just right”—literally, it was minutes from where we were taking the deposition. I said, “It's really close by, it's well known throughout the world, and lots of people go, and I think if you had the opportunity to be in town for this”—I think he was flying up from California, that's what it was—“You might consider going.” 

And his reaction, I will never forget it! He looked at me like completely... just, I don't know. He just looked at me, paused and said, “Andrea, are you trying to trick me? We have depositions tomorrow. Are you trying to throw me off my game?” [laughing]

I bust out laughing because I was like, “No, Tim, I just wanted to share some pretty flowers with you because frankly, you look like you can use some flowers in your life.”


Your diabolical tulip festival plan!


Yeah, yeah. And so I remember leaving that and actually afterwards, I went to the tulip festival because I was already up there. And I just thought, “Gosh, these are not the types of people I want to be interacting with,” you know, whether it's opposing counsel or whatever. But it just was, I don't know, it was such a bizarre reaction from him, but I just thought, “You are not my people, and he will never be my people.” 


It's funny because it is a bizarre reaction. And yet, I think anyone who has existed or does exist in the world of legal practice understands that that's just normal within that kind of environment. Or maybe not normal, but typical. 

The idea that you would just be suggesting something as an interest, that someone might be interested in doing something other than something related to being a lawyer, is sort of met with suspicion and consternation.


Yes! What a hard way to go through life! I mean, to be constantly cynical and suspicious of others. That's a hard way to live.


Yeah, so can we go back to something that you said? I'd love for you to expand on it just a little bit. 

You said something about how you decided you needed to stay at the firm for one year because “because of your resume lol,” [laughing] and I'm sure there are a lot of people listening who are like, “Well, what does that mean? Yes, that makes total sense.”

So can you explain where your perspective on that comes from? Because I think I understand what you're saying, but I suspect there are a lot of people listening who are like, “Well, yeah, like, of course. What do you mean? You're saying that kind of like you don't think that was a real thing.”


Yeah, that's such a great question. 

Well, I definitely felt like it was a very real thing. And your question makes me think, “Well, where did that idea even come from?”

And I think, I don't know, maybe it came from career advising or something in law school or whatnot. Or even in practice, if you talk to people who were at other firms who are just, you know, wanting to give you advice, they're always telling you, you know, “Stick it out, just tough it out. Get that one year, that way, it really shows you made an effort.” I think maybe that's where it came from. 

But it's absurd. Because who made that up? I have no idea. And frankly, it's like, well, you could just pick really any random number, any number of months, any number of years. I don’t know, you pick! But it's completely arbitrary and it's completely made up. So if that's the case, it's like, well, why not just make up what I actually want in terms of duration?


That's so funny because I have had conversations with people, where they say things like, you know, “Oh, it's only five years,” for example. 


Oh my gosh!


Yeah, you know what I mean, though? To your point, it's just an arbitrary number. 

And I'm not saying that these things don't have any meaning if you have very specific intentions for your career path. But I think to your point, if you ultimately know you want to take a different path, clinging to these ideas of what you should do and what the timeline should be... You really need to interrogate your assumptions and figure out, are these assumptions actually based in reality? Are they actually serving me? Or are they just sort of made up things that I'm using to not necessarily fully engage with figuring out what I really want to be doing next?


Oh, absolutely. And even as you say that, Sarah, I mean, the idea kind of comes up that it's kind of a convenient excuse, I think. You know, these random arbitrary markers. “Oh, well, I need to stay in this for a year.” “I need to stay in this for five years.” 

Well, that's a real convenient excuse to not actually do what you want to do, because it's like, “Oh, well, these are the social expectations of the industry. Guess I can't really pursue my dreams.” I mean, it's an easy out.


Well, and talk to me a little bit, because you said that you had in your mind like, “Oh, I need to stay for a year.” And then you said something like, you got to that year, and it was like, “Oh…”

So it sounds like maybe in that year, even though you had this idea of like, “Oh, I could leave and do something else after a year,” that you weren't necessarily actively pursuing... 


I wasn't! Because I was living my own excuse. Right? And I think I was very cautiously trying to figure out what the next steps were. 

And so what that looked like concretely was, you know, if recruiters reached out, I would make sure that they had a copy of my latest résumé. You know, if there were people who were... I think at that time, I was like, “Well, I guess what I'll do next is just go in house, that's like a natural transition, because at least hours won't be so bad. They'll be a little bit more collaborative.” 

And there were just so many—I mean, that's the path of so many lawyers, they go from big firms to someplace in house. So again, there is that just well-worn path that made that path seem really appealing initially. 

And so really, in all candor, my second year at the firm, it was just, you know, get my work done, but my heart was so not in it. But I was actively reaching out to just other lawyers who were working in different settings. I mean, emphasis really was I was reaching out to just lawyers because I couldn't see beyond that at that point. 

And it really was, I think, towards, probably two months or so before I quit. When I connected with a couple coaches, mostly because one of my closest friends, one day we were just chatting and she said, “Have you thought about just getting a coach?” I was like, “What's a coach?” 

She told me and I was like, “Yeah, I don't know. I guess I’ll…” A random Google search, I was like, “Seattle career coach.” [laughing] Instead of reaching out to a couple people, you know. And some of the coaches, they were previously lawyers; others were completely not, which I found appealing. And so I ended up having a couple conversations with coaches up in Seattle. 

But what really did it and what actually ended up leading to me for real pulling the plug and quitting my job—which by the way, I'd never quit a job before in my life. So that was super scary. 

But what happened was, and this feels a little silly to share so publicly, but here we are. I—gosh, what month was it? I think it probably was like August of 2017 by this point. I had met somebody at a mixer that was really interesting, and I was really excited about. And it really didn't end up taking off at all whatsoever. It lasted for like, all of just over two weeks. But for whatever reason, I was so distraught when it ended. And I think in part, actually, in hindsight, it feels like that connection was actually based on the fact that we both really hated our jobs. We were so candid about that, even just with our initial intros.

But I remember when that went away. I thought, “Well, what now? That was actually gonna be my distraction from the fact that I hated my job. And now I don't even have that distractor anymore.” I was inconsolable for about a month. I have actually never experienced anything like that before. But I couldn't get my work done. Like I was crying every single day. 

And I finally got to this point. I remember I took a trip back to Minnesota to see friends over Labor Day weekend. Yeah, it would have been Labor Day weekend of 2017. And as I was flying back from Minnesota, back to Seattle after having spent time with good friends, I just thought, “This is not worth it. I hate this job. It's not who I am. I don't like any of the work. When I look around at the lives of the partners I work with”—that but for maybe one of them, maybe two of them, I was like, “I don't want any of your lives. I don't see any balance whatsoever between your work and your personal life.” 

So I, not knowing what else to do, I just… Well actually, before that, I ended up messaging my parents, asking them if it'd be okay for me to move home with them for an indefinite amount of time, which I think they were at that point, you know, I’d never quit a job before so they were like, “Ooh, this must be like really serious. Yeah, of course, we love you. We support you, please come home. We'd love to have you with us.” 

I think but for that safety net of my parents being generous enough to let me move back home with them, I don't think I would have had the courage. And I think also just I had certainly a level of desperation at that point to just quit my job not knowing what was coming next whatsoever.


Hey, everyone, I'm just popping in before we get to the second half of the conversation with Andrea, because we are about to start talking about how she ended up getting a job as a career counselor in the Career Services Office at Pepperdine Law. 

And I know there are gonna be some of you who are listening and think like, “That sounds super interesting! I am very interested in potentially transitioning into a job in higher ed administration or law school administration. How do I find out more about that?” And if you find yourself wondering that, then the Former Lawyer Collaborative is definitely something that you're going to want to check out. 

So as I mentioned before, the Former Lawyer Collaborative is my signature program for lawyers. It helps unhappy lawyers ditch their soul-sucking jobs and figure out what they want to do next, so that they can trade lawyering for a better life. 

Andrea was part of a virtual panel in June with two other former lawyers who also have transitioned into law school administration and higher ed administration to share about what the job looks like, how to get into that field, and a bunch of other really helpful stuff related to making that type of transition. 

So if you're someone who's interested in that or a transition into any other field, this is part of what the Former Lawyer Collaborative does. It creates a confidential space where you can connect with other lawyers who are also looking to leave, or considering whether they want to transition to a different area of law or leave. And it gives you the information that you need to make that decision. 

So we have workshops and panels every month. We have a group call every month where we talk about the issues that you're running into. Basically, the Former Lawyer Collaborative is designed to give you a framework to walk through to take you from “I don't know what I want to do, but I know I want to leave” to “This is my next step.”

So if that sounds like something that would be helpful to you, come on over to, and join us today. 

Okay, let's get to the rest of the conversation with Andrea.


I think there are a lot of people listening who will completely relate to feeling that level of desperation. I know that when I think back to my time in Big Law, I fully relate to that feeling. 

So let's talk about that a little bit more. Because I think certainly not everyone has the kind of relationship, like a family relationship, that they can count on in that way. But then I think there are a lot of people maybe could avail themselves of, like moving in with their parents or a sibling or something. But the idea of it is just... they just can't fathom it. Right? 

So what would you say to someone who's sort of in that position of like, they are really desperate, but they're struggling to get themselves to the point where they're willing to do what they need to do for their own mental/emotional wellness?


Yeah, that's a great question. I mean, I think I would ask them: the way that you're living right now, what's it costing you? And in terms of whatever that cost is, how much longer are you willing to put up with that?

At some point that's really going to eat you up. And it's your choice, you get to decide if and when you want that to stop. It's always your choice. But I think it really is getting clarity on just what's the toll that it’s taking on you.


Yeah, I think that's right. And also I think—and tell me if you agree with this—but I think so much of it is driven by, “Oh, what will people think?” 


Ah, yes. I love that! OPOs: other people’s opinions. Yes, yes. And it’s so real. I remember the weight of that and... I mean, everybody's going to have an opinion. And depending on whatever your relationship with them, those opinions will carry different weight for you. 

And I think at the end of the day, you have to live with yourself. Your reality every single day? That's your reality. And it's not the other person who's spouting off their opinions. They're not living that out. It's easy for them to say what they think that you should do or what they expect of you because they're not living it. 

Ultimately, I think the most important opinion is your own, like, what do you think about it? And I think sometimes other people's opinions, they're a decoy. It's easy to focus on other people's opinions. You don't actually have to get to the core of what is actually your opinion.


I think that's so important. And I know we've talked about that on the podcast before but just the reality that you are not going to care as much about what other people think if you're really confident in your own path and what you're doing; that times that you're going to have the most challenges with sort of struggling with, “Oh, but what will this or that person think?” Or the amorphous them: “What will they think?” That is really when you're looking for some kind of external validation of your choices, the choice that you want to make. 

And I think it's important for people to be able to recognize that and say like, “Oh, I'm never going to... People, other people are never going to be able to validate me enough to make me feel okay about this choice if I am not doing the work to figure out what I actually want to do and what is right for me.” 


Oh, 100 percent.


And I'm not saying this like... I don't want people to hear us saying, “So if you're not 100% sure, you're bad and wrong and try harder.” This is a very difficult stuff, like vast amounts of personal experience and six-plus years of therapy. [laughing]

I don't want people to hear us having this conversation and think that I'm saying, “This should just be easy. What's wrong with you?”


Yeah, totally. Totally not. I'm so glad you raised that. 

Because it's only really in hindsight now—and it's been, what now? Three years since I quit my job?—that I am able to say that with ease and confidence about that. 

But I remember, yeah, there were a lot of opinions that were shared with me. And I was just like, ugh. And even as you just said that right now, I felt the weight of really even just taking in any of those opinions, because anything that is detracting you from actually just focusing and getting in touch with yourself, it's a lot of extraneous energy that has to be cleared and it's absolutely a burden.


Yeah, I think that's so right. 

So tell me what has happened in the last three years.


Sarah, in the last three years I have been liberated. [laughing] It's so funny and I've been telling friends lately how free I feel and how light and how it's such a relief to just be me wherever I go. 

And I remember when I was practicing as a lawyer, I felt like I was leading this double life where outside of work I was mostly me. I mean, most of the time I was trying to recover from my work time. And in the time that I was recovered I was me, but then unfortunately, you know, you work most of the day and so the majority of the day was spent not being me. 

And now I have this life where I am just, I'm this unfiltered version of just truly who I am at my core. I mean, if you see me in my home, if you see me at work, if you see me, I don't know, just out and about, you will get the same person wherever you go. 

And that consistency is something that has really just brought a lot of ease into my life because I'm not expending unnecessary energy trying to maintain my mulitple selves, you know, trying to figure out like, “Okay, I'm here, this is who I need to be.” “Okay, now I'm here, like, it's now a different person.” 

Now it's just like, “Oh, I just show up.” I’m me, I do whatever I want. I say mostly whatever I want to people. And it's just, it's nice. 

Yeah, and concretely, what I do now. Literally at school, it's funny because with the students I work with, we talk about whatever they want to talk about. I really let them drive and set the agenda with all of our conversations. And so sometimes, you know, most of the time it always starts out with job-related topics, but we can try to compartmentalize our lives but truly all of the compartments, they blend into one another. 

And so if you're having certain struggles in one category of your life, it's going to show up in another one, for example, like in the jobs category, or vice versa. And so for me, I take a very holistic approach to the work that I do with students because I think it's important to understand exactly where they're coming from, what's going on in their lives, and how that informs their job search, if that's even what they want to talk about. 

It's also just a lot of fun too. At school, I order yo-yos for students, we give out so many snacks, it's really a priority that we make sure they're well fed and taken care of. And it's just so fun loving on these students because they remind me of me when I was... Oh gosh, I’m getting emotional thinking about it!

But I remember the ideals that I had in law school, about just starting off my legal career and I wish I had somebody at that time who had just said to me with respect to my career, “You know, you get to be whoever you want to be, you get to do whatever you want to do. And it's okay.” I mean, I just, I never got that message. 

And fortunately, that message finally showed up. But it is something that I do my best to impart with anybody I work with. Because I think at the end of the day, what the world needs most is for us to just be who we are and to share our natural gifts freely with each other and that's how we're actually going to change the world, I think. So I really love the opportunity to do that every single day with the students and the people I coach.


I think that's so good because… you touched on this, I think in what you were just saying, but in law school and sort of in the legal profession, I think people get this message explicitly and implicitly, as soon as they get on the law school conveyor belt, like LSAT, law school, et cetera, of like, “This is the kind of person you should be, this is the way you should be. These are the things that you should be doing.” 

And very much there's this... it's not explicitly communicated this way, but it's sort of like, “Who you are doesn't matter. You need to be this person who does these things.” 

And it's come up a lot in the last couple of conversations I've had for the podcast, this idea of people ending up in positions where their natural gifts and their natural strengths are not just not valued, but in some cases are liabilities.

And I think for people who are starting out, who are still in law school, it's just so important for them to hear that who they are, and their natural gifts and talents, those are good things and they should look for ways to use those things, not just try to become this person that they think they should be who fits into this very narrow mold.


Absolutely. And even as you say that, I love that you touch on this distinction between being versus doing. I mean, I think we, for better or worse, we're in a world where the emphasis is really on the doing. And it's understandable because—especially, I think, in a country that values productivity so much—its productivity results from what we do. But I think there's so much gold in just the who we are, or the qualities we want to embody and to live out. 

Who are we right now? Who do we want to be? And once we have clarity on the “who,” the rest will all follow: the “what” and the “how,” that will all follow the “who.” I'm so glad you brought that up.


So let's talk a little bit about the more technical aspects of how you found the position at Pepperdine. 

The reason I'm asking is that I hear from a lot of people who have an interest in moving from legal practice into some sort of higher ed administration or career development, of the type of position that you have. 

But here's the thing: it's been my experience that many lawyers feel deeply insecure about their ability to do those jobs.


Really? that's so interesting!


In the sense of like, people get so sort of narrowly focused on like, “This is the type of job that I'm doing as a lawyer.” And when they go to want to pivot, there's this something inside them that's telling them, “Well, maybe you don't have what it takes,” or like, “Maybe you don't really have the skills.” 

And so I’d just love for you to talk a little bit about that. Because I know that there are people who are listening who are having thoughts like that, but also have an interest in moving into that kind of role.


Yeah, it's so interesting you say that, because I actually had never thought of it that way before. 

Because I think some of the narratives I had been hearing when I was considering going in this direction, I definitely got some feedback from other other lawyers who were just like, “Oh, yeah, you just wanted to phone it in. You just wanted an easy job.” 

So it's interesting to hear you say that there are folks who worry that they wouldn't be able to do a counseling job. I think that's really fascinating. 

But yeah, in terms of how I moved into the counseling job, I remember I basically took, gosh, it was probably six or seven months off after I quit my job. To just rest. I rested for about two months, literally doing nothing. And then my mom's like, “Are you gonna get a job?” And I'm like, “Yeah, I promise I will.” 

And so I started doing outreach, brainstormed a couple categories of professions that seemed interesting. And professional development quickly became clear, like it's definitely at the top of my list. I didn't know if I wanted to do it in a law firm context or a law school context. 

So I basically just networked my butt off. I talked to so many people who worked in various professional development roles, both in the law firm setting as well as the law school one. 

And I ended up finding the Pepperdine job through a jobs board. It's through NALP, which is kind of this governing body for legal professionals who are in this line of professional development work. And they have a great jobs board. So for anybody who's looking for a career counselor role for sure check it out. 

Yeah, so, it popped up. And I had applied to multiple career counselor roles, including one at my alma mater. And it was interesting because I was interviewing for a position down in Texas, one in Massachusetts, when this Pepperdine one showed up, and I didn't know anything about Pepperdine. And I looked it up on Google Maps and I realized, “Oh, it's in Malibu! Right on the Pacific Ocean!” And I've already shared with you how much I love nature. And so I thought, “Well, that sounds really cool.” 

So I applied and it's so funny, I remember my interview with our team. And of course, the question comes, you know, “Why are you interested in this job?” And of course, I said something about wanting to work with students. But I also remember sharing with the team, I said, “I'll be real honest, like, your view is incredible. Like, why would you not want this view?” And I think the rest was history. I think then they asked me a question about like, what's my favorite snack. A question I've never gotten on an interview before and I was like, “That was fun. I like that!” [laughing]

So that's kind of how that fell into place. But it really was one of those things where it makes me think back on that job search period. And there were definitely moments where I… There was definitely a moment of struggle too, because, you know, some of the schools that I was also interviewing at, they were higher ranked, if you go by the U.S. News and World Report rankings. And for somebody who for most of my life, I've lived by the rankings, right? Like, that's how I picked my college. That's how I picked my law school. It was really hard to let go of that mindset.

And so, that was really interesting to observe. And I remember as I was sort of in the final stages of finalizing the offer acceptance and everything, I talked to my coach and she's like, “Why are you crying? I've never talked to somebody who's crying over a job offer.” And I said, “I think this is, like, the death of my ego. I'm taking a job where I get paid half of what I used to make. I don't have a fancy title, right?” And my ego was just having a huge fit. It was just like, “No, this is not how you have lived all of your life!” 

And I also remember telling my coach, I said, “But I also feel like there might be a greater purpose that's working here that I can't see in this very moment. And that perhaps I'm being called to this place to learn something that goes beyond this ego that has for too long been in the driver's seat of my life, and perhaps it's time to practice putting that ego into the backseat.” Because the ego, you know, it is useful, gets stuff done really well. But it also has led me to different paths that I wouldn’t necessarily do the exact same way if I had the choice. 

So it was a really interesting experience. And the transition to my counseling role I would say, in my first year, there were definitely struggles. I remember my first week or so, one of my roles at the law school, I counsel on judicial clerkships and externships. And so of course, for the judicial clerkship applicants, they need to send in recommendation letters from professors. And so I process all of those letters. 

And in that first week on the job, I had to stuff my own envelopes, which I had never done as a lawyer because I always had an assistant who would all of that, or a paralegal who would take care of that. And again, those were the moments for my ego was just like, “What? You did not get a JD to stuff envelopes!” And so, that first year, honestly, it was a real ride with my ego.

And now looking back, there's so many reasons why this job ended up being placed in my life. It was really, first and foremost to really examine the role that my ego had played in my entire life and to reconsider if I wanted to do it a little differently and it turns out that I absolutely do. My ego is for sure in the backseat now. 

But this role has also been such a gift because it has shown me just how much I enjoy working with the students. It's truly the highlight of everything, and fortunately that's the majority of what I do in my job. 

I think it's also really just taught me that I am so much more than just my job. I think for the longest time I always tied my identity to the job. And now I'm just like, “No, a job is just a thing I do. It is not who I am. I'm a lot more than that.”

And the gifts that I've been able to bring into the world through my work with my students. You tap into an inner power that is unshakable, and it can't be affected by external circumstances or other people. And when you can't be shaken by anything external, that's true power right there. And it's an incredible feeling.


I'm so glad you shared that because I was wanting to circle back to something that you mentioned, which was that in getting ready to take this position, you got some pushback from lawyers, that essentially that job is beneath you.

I think that that kind of thinking—sort of our own egos, and then the fear of other people saying something like that or having that kind of opinion—really does, in my experience, prevent people from making the choices that are truly the best for them. So I really appreciate you sharing that because I think that that is a process that everyone has to go through in order to really figure out where they should be. 

Andrea, as we get towards the end of our conversation, is there anything else that you would like to share that we haven't touched on yet?


Sure. I mean, I think I would encourage any of your listeners, for those who are thinking about changing jobs, to not view your job search as just a job search. I remember when I was going to my coach, I actually just thought, “I just need a new job and that will fix all of my problems.” But really, that job search… [laughing] That laugh suggests that you perhaps know that feeling!


Yeah. And it's… I mean, it's the classic story. It's the classic story. It's like, “Oh, I just need to fix the job.” And then you realize, it's like you said earlier, the career touches on everything, all the things.


It touches on all of the things. 

And I think that's fine! If you want to treat this as just a job search, you know, go for it. But I would offer that simply rearranging your external circumstances, taking on a new job, if you have not actually resolved or addressed the issues that are actually underlying your frustrations, you're just going to take them into your next job, and it's going to reappear, again, just with different characters, a different office. It's just going to continue until you actually get to the bottom of it. 

And so I encourage folks to look at their job search really as an invitation into the inner path of getting to know themselves, getting in touch with their soul and who they are. And of course, that's going to lead to a lot of uncertainty and that uncertainty, understandably, can lead to great fear. 

But I would suggest that what you actually want is on the other side of that fear. And that uncertainty, I mean, everything is uncertain, and it's all temporary. So that's one point. 

I think the other point that I would offer is don't be shy about reaching out for advice and for help and a sounding board. I was so humbled when I was in the process of figuring out my next steps, just how generous people were with their time and their willingness to help and introduce me to other people in the industry, whatever industry that was, of interest at the time.

You know, people want to help to the extent that they can. So don't worry about being a burden on somebody. That's something I hear from a lot of people often. You know, if people don't want to help, they'll say, “No,” and it's not personal, you can just say, “Thank you,” and you move on. But there will be so many people who do want to be of assistance. So definitely take advantage of that. 

And then the third point, and the final point, really is this message of hope. I know and I have full faith and confidence that every one of your listeners, you're going to find your way. And that journey, it's going to be so interesting. It's going to be heartbreaking in some moments; it's going to be exhilarating in others, and it’s going to be everything in between. But what you will learn about yourself, your relationship with others, your relationship with the world… I mean, it's a ride that I am so just humbled to be on still.

And there's light on the other side, there's so much light coming your way. And even if you don't see it in this moment, it's coming. I know it.


I love that. And I think those are some really important insights. And we didn't talk too much about this, but I know, Andrea, in addition to your work with students, you also do one-on-one coaching. So for people who are listening and are interested in following you or getting in touch with you, related to any and all of the things that you do, where can they find you online?


Yes, you can learn more at my website at You can also connect with me on LinkedIn, or on Facebook, under Andrea Yang. 


Awesome, and I will link to those in the show notes. So you can just go there, click the links, find Andrea and connect with her. 

Thank you so much, Andrea, for sharing your story. I really appreciate it. I loved our conversation. I think we talked about a lot of really important things.


Oh, thank you so much for this opportunity. You are such a gift and I'm just so glad that you're sharing your gifts with the world because it really makes a difference. 


Thank you. 


Thanks so much for listening today. I absolutely love getting to share these stories with you. If you haven't yet, subscribe to the show, and come on over to to get even more support and resources in your journey out of the law. Until next time, have a great week!

So, SHOULD you leave the law without another job lined up?

How bad is it to have a resumé gap?

This question comes up so often that I’ve created a video sharing what I think you need to know if you’re considering quitting your job as a lawyer before you have another job lined up.

To watch this and other videos on the Former Lawyer YouTube channel, click here!