Writing A Book About Former Lawyers While Leaving The Law With Adam Pascarella [TFLP146]

Welcome back to the Former Lawyer Blog. On this episode of the podcast, Sarah had a conversation with Adam Pascarella about his journey in writing a book while leaving the law.

Adam is currently the founder and CEO of Second Order Capital Management. But before that, Adam worked in Biglaw as an associate and ended up writing a book while leaving the law. 

The process Adam went through to figure out what he wanted to do after leaving the law is so interesting. So, stick around to read all about Adams’s journey in writing a book while leaving the law!

Adam’s Journey Through The Law 

Adam went to law school originally having a political career in mind. He never planned on working in the law long term. He enjoyed the intellectual aspects of law school, but he didn’t have a good idea of what working in the law would look like. 

While he did get some feelings of a disconnect, Adam knew he wasn’t alone in feeling that the law wasn’t a good fit. And again, he didn’t see himself being there for long. So, he pushed on and graduated. 

Pro Tip: Do An Audit Of Your Post-Law School Objectives

If you’re a law student and have thoughts of doing something else, don’t start panicking. Instead, think about what you’re going to do about it. Do an audit of your objectives of what you want to do after law school. 

You don’t have to go down the corporate law path. If you do, it may delay whatever you want or are meant to do. So, resist the temptation to follow your other classmates down that path if it feels wrong.

Working In The Law 

After graduating from law school, Adam was excited to work in the law. He never liked the lack of practice in law school. He wanted to embrace practicing as a lawyer. 

For the first couple of years, Adam was all-in and really enjoyed working in the law. His skills improved and it became satisfying to provide something of value to the firm. But, he still didn’t envision working in the law forever. 

Adam was itching to do something new. He knew he wanted an entrepreneurial career, something non-traditional. He wasn’t going any further down the Biglaw track. He started feeling the pressure of time, so he made the leap and decided to leave the law. 

Writing A Book While Leaving The Law

Adam confessed that he began writing a book to help navigate his way out. He was still working in the law when he began working on the book. The main focus was having a diverse set of voices about leaving the law. 

Adam sent cold emails out to some successful former lawyers like Keith Rabois, who was interested in speaking with Adam. After speaking with Keith, Adam was off to the races and started reaching out to other successful former lawyers. 

The Importance Of Relationships

In the law and even in other industries, there are peaks and valleys. And to navigate those peaks and valleys, it’s important to rely on your network and your relationships. Your career success is mostly based on your talent. Second, to that, it’s about relationships. People helping people. You provide value to them, they provide value to you. 

Creating mutual value grows your career. It’s important to create strong relationships because you never know what’s going to happen. Focus on maintaining those relationships as well. It’s easy to build relationships. It’s harder to maintain relationships, especially with how busy things can get. 

Lessons In Reversed In Part

Reversed In Part is a book about former lawyers who have done amazing non-traditional things after leaving the law. Adam spent three years interviewing multiple former lawyers and hearing many success stories that prove there are so many things lawyers can do after leaving the law.

Thinking About What You Don’t Want To Do 

One of the interesting lessons of the book is knowing what you don’t want to do. If you’re working in the law and you want to get out, it’s important to think about what you want to do, of course. But, it’s also important to know what you don’t want to do. 

When writing the book, Adam interviewed Jessica Medina, who has been on the Former Lawyer podcast twice to speak about her journey in and out of the law. 

Adam spoke about how Jessica realized that during her time working in the law, she realized she wasn’t truly an argumentative person, and this was something she wanted to avoid after leaving the law. Doing this helped narrow her focus by eliminating what she didn’t want. 

Premature Optimization After Leaving The Law

Premature optimization is the idea that you want to evaluate your assumptions upfront before investing more time into something. As an example of this, Adam talked about his interview with Tiffany Duong, who has also been on the podcast. 

He mentioned that after leaving the law, Tiffany tested her assumption of a career in marine biology. Tiffany quickly figured out that marine biology wasn’t for her. So she transitioned to another route.

Testing your assumptions before committing to a new line of work is key. You don’t waste any time, you don’t waste any money, and it helps you get closer to what it is you truly want to do.

Be Careful About Following Your Passion

There are compelling arguments on both sides of whether you should or shouldn’t pursue your passion or hobby as a career. But, it’s something you should be careful about. 

An example from the book is Sander Daniels, the CEO of Thumbtack. He didn’t grow up being passionate about local services. It just fell into his lap. But, while working with his co-founders, he became passionate about it.

Keep that in mind, especially lawyers that want to leave the law may be wanting to do something that they’re more passionate about. Consider what you’re passionate about, but be a little careful with that because you could lose your love for whatever it is.

Leaving The Law? Get Your First Steps Here!

Are you starting your journey to leaving the law? Get started by downloading the free guide: First Steps to Leaving the Law. 

Sarah is now offering a small number of spots for any lawyers who are interested in 1:1 coaching. If you want to learn more about that, listen to Career Coaching for Lawyers: Working 1:1 with Sarah Cottrell.

Connect With Adam




Mentioned In This Article:

Reversed In Part By Adam Pascarella 

Second Order Capital Management

Episode 59: Moving Beyond Biglaw As A Single Mom Of Twins With Jessica Medina

Episode 60: Jessica Medina: From Biglaw To The SEC To Financial Counselor For Biglaw Lawyers

Episode 12: Tiffany Duong: Renewable Energy Lawyer to Environmental Advocate

First Steps To Leaving The Law 

1:1 Coaching With Sarah

Episode 145: Career Coaching for Lawyers: Working 1:1 with Sarah Cottrell

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.

Today on the podcast, I'm sharing my conversation with Adam Pascarella. Adam started out in Biglaw and pretty quickly knew that was not going to be the thing that he wanted to do forever. He now runs a small hedge fund, but the process that he went through in order to figure out what it is that he wanted to do is so interesting. He actually ended up writing a book about lawyers who have left the law to do other things as part of his process of figuring out what was next for him. On today's podcast, we're talking about Adam's own journey out of the law and also some of the things that he learned in writing this book.

Before we get to the episode, I want to remind you that I now offer a limited number of spots for lawyers who are interested in doing one-on-one career coaching with me. If that's something that you might be interested in, you can stay tuned for more information later in this episode. You can go back and listen to last week's episode where I dove into that in more detail, or you can just head to the website and under the Work With Me drop down, look at the one-on-one coaching information. On that page, there is also a button to book a consult with me if you're interested in talking about whether this would be a fit for you. All right, that's it for me. Let's get to my conversation with Adam.

Hi, Adam. Welcome to The Former Lawyer Podcast.

Adam Pascarella: Hi, Sarah. Thanks so much for having me.

Sarah Cottrell: I am very interested to hear your story and also about this book that you wrote. Let's start with you introducing yourself to the listeners.

Adam Pascarella: Sure. My name is Adam Pascarella. I am the founder and CEO of Second Order Capital Management which is an investment management firm located in New York City, but more relevant to your listeners is the fact that I am the author of Reversed in Part which tells the story of 15 law school graduates who have done really non-traditional amazing things with their careers.

I spent three years writing this book and I spoke with individuals in plenty of different fields ranging from venture capital and startups, to art and politics. The book was really a labor of love and it goes to show that there are plenty of different things that you can do with your law degree and legal experience.

Sarah Cottrell: Okay. Also relevant for people to know is that while you currently run this investment management firm, you are a law school graduate and practiced law and decided to bail out of that. Is that correct?

Adam Pascarella: That's right, yes, I should have added that. I graduated from Penn Law School in 2014, went to work at a large commercial law firm out here in New York City, Baker McKenzie, from there until around 2017 or 2018. I practiced for about two and a half, three years. I was a litigation associate mostly specialized in general commercial litigation, but as your listeners know, when you're a junior associate of one of these Biglaw firms, you take whatever work that's presented in front of you.

I did a little bit of anti-trust work, some white-collar defense, that sort of thing, and practiced for two and a half years and stopped practicing after that and haven't really looked back, although I do keep up with my CLE credits. That's something that I definitely keep up with.

Sarah Cottrell: Yes. It's interesting, I also started at a Biglaw firm, I also started in litigation, and just shy of three years there I was like, “Yeah, no, I need to get out of here,” so I left for a legal publishing company and then I ended up as a staff attorney at a state court of appeals for a number of years. We definitely have some overlaps in our story.

I'm trying to think, there are so many things that I would like to talk about, but can we talk a little bit about what made you decide to go to law school in the first place?

Adam Pascarella: Sure. When I was in high school, maybe even grade school, I was thinking about my career as most of us do and I thought that entering politics was something that was interesting. I was actually one of those weird high school students that went to politics summer camp essentially. It was through an organization called the Junior State of America. I think it's still around. What you used to do is you went for about three or four weeks to colleges around the country.

I went to Stanford one summer and Georgetown the other summer, and you take college-level courses and politics government policy during the day, and then in the afternoon, at night, you actually engage in basically Lincoln–Douglas style debates with your classmates about issues of the day. It's a politics nerds paradise. I absolutely loved it. I saw myself going into politics one day. When I was looking at other politicians and how they had gotten to where they were, I saw that most of them were lawyers, so that was the main catalyst for me wanting to go to law school.

But along with that, I was just generally interested in the law itself. I would read legal books when I was in high school, in college, learning about different famous trials throughout history, that sort of thing, so it wasn't like I saw law school and being a lawyer as just this intermediate step to getting to politics, I thought that I would actually be intrinsically interested in it, but the end goal, like I said, was to get into politics.

Now granted, looking back now to what I was thinking back then, it's interesting how the world has changed and how I have changed. It's hard to see me getting into politics anytime sooner in the future. There's a certain type of person that is good for that and I don't think I'm a good fit for that but it just goes to show how careers are fluid, they shift all the time. What we really have to do is evaluate your current skills, your experiences, and make the best decision with the information that you have.

Sarah Cottrell: Yeah. It's so interesting, I think for those of us who chose to go to law school, it's so common that you reflect back on what your idea of what it was to be a lawyer or what it was to use your law degree when you were, even in some cases for many people, we’re talking like grade school, high school. Now at the ripe old age of 38, I look at that and think like, “Oh, so young, so young.” But there is this sense of what the experience of being a lawyer is going to be like, and then the reality of that often doesn't match the vision that you have in your head.

Talk to me a little bit about that. You said for you, law school wasn't just like this stepping stone into politics, and of course, now you've decided that actually going the political route wouldn't be a good fit for you but you also were interested in the actual law and legal work. Tell me when you got to law school and were actually going through your years of law school, were you like, “This was a great life choice” or were you like, “This might not have been the best thing I've ever done”?

Adam Pascarella: To be frank, I think it was a little bit of both. On one hand, I did to some extent enjoy the intellectual challenges and exercises that were part of your day-to-day life as a law student. As you and your listeners know, everyone in law school is talented, intelligent, driven, hardworking, so it's very inspirational to be in an environment like that while also talking about the issues of the day and all legal precedent.

That was something that was interesting to me, but at the same time, like you were saying, I didn't really have that good of an idea of what being a practicing lawyer was like and is like. As part of writing this book, I wanted to also address that question, like how can prospective law students or lawyers get a sense of what it is before spending hundreds of thousands of dollars to go to law school?

I didn't really find a clear answer on that one besides maybe being a paralegal for a summer job or something, or having a family member be a lawyer. That's a separate conversation, but back when I was in law school, I did think that I wanted to do something more entrepreneurial, start some startup whether that was in tech or something else. After class whenever I had any free time, I did work on some side projects and side ideas and tried to meet people in the tech community. I was dipping my toes in the water there.

To go back to your initial question, it was a mix of both. I thought that this was interesting. There are aspects of law school that are interesting. I could see myself being a lawyer for some time but there's a bigger vision of where I want my career to go. To be frank, it didn't end up with me being a partner at some firm or practicing for 50 years then retiring. That was never the plan for me.

Sarah Cottrell: Did you feel like you were an outlier in the law school community? Because some people will talk about feeling almost this pressure, this idea of like, “Oh, I don't want to do this with 100% certainty or forever and maybe that means there's something wrong with me,” but other people have a different experience. Tell me a little bit about that.

Adam Pascarella: Yeah. I certainly don't think I was alone in feeling these feelings that, “Hey, maybe legal practice itself isn't exactly what I want to do.” Now granted I went to Penn Law School like I said, and I did have some classmates that were obtaining their JD MBA so they were taking a good amount of courses at the Wharton School, so they weren't planning on practicing for the entirety of their careers, obviously, or perhaps even after graduation. They were looking to diversify their skills and experiences in the business world, so there was that as well.

But I do think that if you're a law student and you do have these thoughts of wanting to do something else, first of all, there's nothing necessarily wrong with you, especially if you don't have any prior experience or knowledge of the legal field, which I think is a good number of law students. First of all, I would say don't panic and don't freak out about that, but I think the larger question is what are you actually going to do about that?

In some circumstances, the inertia is so strong that it can lead you down a path that you know you don't want to be on but you still go down that path. Example A of that is going to a big corporate law firm. I'm not saying that in my circumstance, that inertia took me that way. I willingly made that choice and I was happy making that choice, but for some people it's just a natural choice and they don't question it as much as they should.

When you go to a law school, like Penn or any of these bigger law schools, they make it very easy for you to go down that particular track. If you think about it after 1L summer, the employers come to you, you have on-campus interviewing for a couple of days and the numbers are eye-popping, you can make a six-figure salary, you can live the lifestyle that you want to live. Even though you may not be practicing the way that you envisioned you'd practice, it still is a pretty good life so it's very easy to fall into that track.

I would say for law students particularly listening to this, just maybe do an audit of your objectives both short term and long term of what you want to do after law school. You don't have to go down the corporate law path. In fact, if you do go down that path, it may delay whatever it is that you want to do deep down what you inherently are meant to do or want to do and so you're just taking on opportunity costs because time is advancing for all of us. We all have choices to make in our careers every month, every day, every year, so it's important to I think really do an audit of your goals and objectives and resist the temptation to follow your other classmates down that path.

Sarah Cottrell: Yeah. We've talked a lot on this podcast about how it's like a conveyor belt, and once you get on the conveyor belt, it just keeps on going. Tell me, when you got to your firm, were you like, “This is fine but I wasn't really planning on necessarily being here in the long term anyway”? Were you like, “This is going to be great and I'm going to make it work”? What was your thought process when you started practicing?

Adam Pascarella: Honestly, it was more of the latter. I was really excited to do it just because law school itself wasn't exactly fit for me. Granted I did enjoy the discussions like I was saying a couple minutes ago, the intellectual discussions that we had, but I'm more of the person that I want to get beyond the theory and embrace the practical. I want to get into the world and be this amazing practicing lawyer that I envisioned I could be.

I was really excited to get started. To be frank, it was intimidating to get started because as you know, and your listeners know, in law school, it's difficult to teach you the practical skills that you need as a lawyer, as a junior associated of corporate law firm, you're basically thrown into the fire and have to figure it out. That involves some stress, some sleepless nights, and all that, but I was definitely willing to take that on to prove myself and show that I could bring value to the firm.

I was really excited to take it on. Like I was saying a few minutes ago, I didn't envision myself staying as a corporate attorney for decades and decades, that was never the plan, but I was ready to take it on for all it was and learn all these skills that I've been wanting to learn.

Sarah Cottrell: Okay. Tell me what happened because you said that you were there for a little less than three years. Talk to me about your progression through those years.

Adam Pascarella: Yeah. The first couple of years, I was all in, I was really enjoying it. I could tell my skills were getting better. It was becoming more satisfying because I could actually see I was contributing value to both the partners and associates of the firm, so that was really cool. At the same time, like I was saying, I didn't envision staying at a firm for a long, long time and I was getting the itch.

I realized that I was only getting older, I didn't have as many responsibilities as I knew I would have, essentially being married or having children because when that happens, it's so much harder to take a risk professionally just because you have people relying on you. I recognize at the time that I had basically the maximum amount of freedom that I would have in my lifetime.

There was that. Then I was having the itch to start something new, to start a startup. I didn't know exactly what that was and it took me some work to figure out that my real passion was investing in stock picking but at the time, I knew I wanted to have an entrepreneurial career, it was going to be a non-traditional career. Biglaw and corporate laws really set you on these tracks that you need to follow and the tracks are so well trodden that you have lockstep compensation, you stay X number of years, you get paid X number of dollars.

That didn't really appeal to me. I wanted something that was more asymmetric where I can make some bet on myself and have massive returns both financial and otherwise down the road. All of these things were in my mind, I wanted to do something different, didn't know exactly how it would turn out but I realized that the clock was ticking and I was young and could do it and so I ended up taking the leap.

Also, another thing that helped me was speaking with a career coach. I think career coaches are valuable for so many reasons. I'd say two of them, in particular one, is that they hold you accountable. You can talk about leaving your firm or the legal industry itself, ad nauseam, you could talk that to death, but it's so much harder to actually pull the trigger and do it, and so having someone hold you accountable like a career coach is very, very helpful.

Secondly, he was an objective voice in analyzing and helping me analyze what I wanted to do. I think his lawyers are very analytical people, yours truly included, so we can think issues or decisions to death and it's very easy to become myopic about the possibilities and range of outcomes out there. Having him help me think about other options or other possibilities was really refreshing and inspiring and helped me leave my job to do something different.

Sarah Cottrell: Yeah. One of the things we talk about on the podcast frequently is the fact that clarity follows action and not the other way around, which is so-so-so counter-intuitive for any of us who are lawyers because we really feel like we should be able to think things through and know 20 steps ahead and then execute. In my experience and what I see with my clients and the people who I interview for the podcast, it's just not how it works. You really do, at a certain point, have to take some action in the direction that you think you want to go in order to get more clarity about what to do next.

Adam Pascarella: Yeah, there's no doubt. Action is everything, especially if you want to do something new outside the legal field. I think it's also important to say that action doesn't mean that you have to quit your job right now. It doesn't have to be a gigantic, gargantuan action, it could be something small. If you're looking to transition into a different industry, for instance, maybe it's meeting someone in that industry and taking them out to a coffee and learning about what they actually do. It can be as small as that.

It can be as small as starting a blog or tweeting more as long as your firm or job allows it. These things are especially important, Sarah. I think you're really on to something that's even though it may be super scary to do, action rules the day and you have to do something, you can't think yourself to death, otherwise, nothing's going to change.

Sarah Cottrell: Yeah. That's so right because I think people really need to hear that action is important but also to your point, I also think it's really important for people to know that it isn't like your options, when it comes to taking action, are doing nothing or quitting your job today. There are lots of things in between those two extremes that can move you in what is ultimately going to be a better direction for you.

We'll circle back and talk a little bit about how you figured out what you wanted to do when you left/after you left. But first, I want to talk a bit about this book. When, in this whole process, did you start thinking about writing this book?

Adam Pascarella: Yeah. I was really writing the book to almost help myself navigate my own transition. This was I think a little bit before I left the firm, I was thinking about writing something about this very topic. I had a suspicion that there were many lawyers and law students out there that wanted to have a nonvanilla career, a non-traditional career, but they didn't really know how to get from point A to point B, and what you can do in that situation is you can start googling people that were former lawyers that have achieved massive success in another field. Maybe your network is big enough where you can actually speak with them.

But I wanted to really present a diverse collection of voices on making this transition because it's not that uncommon. I was looking at some data while I was thinking about this book. There was a study, I think it was from the American Bar Foundation, where they were looking at attorneys that had passed the bar, I think it was in the year 2000, and were tracking their progress. It was about 10% weren't practicing in 2003, so that was three years later, and then about 25% of them weren't practicing in 2012, so 12 years later.

This was a study from 2000 to 2012 so the situation has changed from that, especially with The Great Resignation and all the macroeconomic events that have happened. I think there are a lot of people that are thinking about this transition, so that was another catalyst that led me to write the book.

In the process of writing the book, I wanted to speak with a bunch of different people in different industries, like I was saying at the beginning of the show, and what I did is I sent a cold email to Keith Rabois who is one of the members of the PayPal mafia, he's a renowned venture capitalist, and I said I was thinking about writing a book on this topic and he sent me a very brief response saying he was interested in speaking with me and then I was off to the races.

It was from there, I cold emailed every single person in the book which was really cool. I had no prior relationship with any of these people. I think the lesson there is that, again, action rules everything. Even if you're sending out a cold email to someone asking for advice, you never know what'll happen from there. That's really what led me to start the book and to collect all these people that I interviewed in the book.

Sarah Cottrell: Yeah. One of the things that I tell people is I think former lawyers in particular are very willing to talk with, help out lawyers who are thinking about doing something else because of all the people in the world, former lawyers understand the most what it is like to be a lawyer and why someone might want to be doing something else with their lives or with their life. I have sent many a cold email in my day.

Adam Pascarella: What was the response from those? Did you find a lot of helpful information or no?

Sarah Cottrell: Yeah, for sure. Honestly, when I started the podcast, so the podcast has been going since August 2019 and a couple of the people who I had on in the first couple of episodes were people who I went to law school with but even in those first 10 or 12 episodes, most of the people who came on the podcast were people who I had literally never met, who I either found through LinkedIn or Instagram or googling and thought like, “This person has an interesting story, I think they would be a great person to have on the podcast.” People are very willing to share their stories and to be helpful to other lawyers who are thinking about leaving. That has been my experience as well.

Adam Pascarella: For sure. Because I'm sure they were going through the same questions, even anxieties that current lawyers are going through, like, “Oh, I invested this time and money into becoming a lawyer, maybe practice for a few years, yes, this isn't really making my heart sing, so to speak, but I don't exactly know how to transition out of the legal industry into something else.”

I can see why former lawyers would be certainly willing to help because it's a difficult dilemma, it's a difficult thing to figure out. I hope this book helps people think about some of the questions and variables that they should consider before leaving.

Sarah Cottrell: Yeah. Tell me a little bit more about the book. I'm really curious to know if there was anything that surprised you in the writing of the book.

Adam Pascarella: Yeah. I would probably say, and I knew there's going in, but what really surprised me is how important relationships are. It's so easy, I think for lawyers especially too, to think that as long as you go on this one path, this one track, you'll achieve your career goals. You'll do very well in the LSAT, you'll get into a good law school, while in law school, you get a great job, you perform well at your job, you retire happily ever after. But the reality is that careers certainly don't work that way, it's not like a stock chart where it goes up into the rights, there are lots of peaks and valleys.

To help navigate those peaks and valleys, it's important to rely on your network and your relationship. Every single person in this book relied on some relationship to get them to where they are. It wasn't like Jay Bilas, who's one of the people I interviewed in the book, ESPN college basketball commentator, it wasn't like he went to indeed.com or went to some hosting website, posted his resume there, and was able to become an ESPN college basketball analyst, it certainly doesn't work like that.

It's mostly based on number one, your talent, obviously, you have to be talented in what you do, but secondly, it's about relationships and people helping people, you providing value to them, they provide value to you, and you create mutual value that way, you grow your career that way. I would say even for law students listening to this podcast, it's important to create those strong relationships, even in law school because you never know what's going to happen.

Your classmate, the person sitting next to you, could be one of your best clients or they could be your boss or you could hire them, you just never know. Really focusing on building and maintaining those relationships as well. It's easy-ish to build relationships but it's difficult to maintain relationships, especially with how busy we all are, so that's another thing to keep in mind.

Sarah Cottrell: Yeah. I think there's also the reality that okay, building those relationships is super important but I think a lot of lawyers feel like they should be able to just achieve everything on their own. There's almost a sense of like, “Well, if I need someone else to do this, then I must be doing it wrong,” and to your point, it's like actually no, that is how people figure out new things, figure out where they want to go, get connected.

One of the things that I work with my clients on all the time is doing informational interviews like, “Hey, I'm interested in this or that career or field. I don't know a lot about it. I need to get some information,” and everyone's like, “Ugh, informational interviews.” I'm an introvert, so trust me, I am not like, “Woo-hoo, that sounds super exciting,” but the reality is that is how you figure out what it is that you want to do, that is how you make connections, and not in a graspy and using-people way, I mean in a real that is how you learn and figure out like, “Oh, hey, maybe this isn't actually the direction I want to go, maybe I should consider something else.”

That is a huge part of the process and also it's something that a lot of people really dislike which is why when I'm working with my clients, whether it's one-on-one or in the Collab, often a lot of what I'm doing is providing support around strategizing about this kind of stuff and then actually doing it. Because to your point, there's the actual doing part of it that can sometimes be challenging. You're like, “I know I should do this but I don't want to.”

Adam Pascarella: For sure. What you were saying a few moments ago, just this temptation to take everything on yourself, that's something I can speak to as well. I don't know exactly where it comes from, I'd have to think about that a little more, but maybe even in law school, to get good grades, it's mostly on you, you have to do the work, you have to read the case law. You may be part of a study group and share outlines or something like that, but for the most part, it's on you. Maybe those habits and behaviors are ingrained in law school and then carry over to our professional careers, it's possible.

But yeah, going on informational interviews or lunches, whatever the case may be, just speaking with people outside your industry is hugely important, one, because you may discover that what these people are doing is something you may want to be doing, but secondly, you never know how they could help you even if you do stay in the law and want to be a lawyer for the next number of years.

Just meeting people and putting yourself out there is really important. I know people hate the word networking, I don't really enjoy “networking” myself, but relationship building is just so important and powerful and part of life that you just have to get beyond it and just put yourself out there.

Sarah Cottrell: Yeah. Networking conjures up these horrible images of some really awkward bar association happy hour or whatever. I think to your point, and I know I've talked with several guests about this before, it really can just be like making a connection with individual people which feels much less daunting than awkwardly standing around with a mediocre to bad gin and tonic.

Adam Pascarella: For sure, you don't have to be holding court at some bar in front of some people. You can speak one-on-one with someone, or even better, if your office allows you to do this, creating content is a huge way to network. If you can create valuable content whether that's through social media or blog and put it on the internet, interesting people will come out and speak with you. That's another indirect way of networking that I think is hugely beneficial for people.

Sarah Cottrell: Okay. Tell me a little bit more about this book because the people who are listening to this podcast, for the most part, are lawyers who are at least exploring the possibility of leaving legal practice, many of them are like, “I want out. I just don't really know exactly what it is that I want to do or how to get there.” Are there other things that you learned in the writing of the book and the stories of the people who you share in this book that you think would be helpful for people in those positions?

Adam Pascarella: Yeah. There are a couple of lessons, and if you look at the book, I summarize my key takeaways from every interview, I had 25 key takeaways that I found. The readers may have different takeaways but those are the ones I found most relevant. One of the sneakily interesting ones that I think is helpful is to know what you don't want to do.

Now, if you're a practicing lawyer or a law student, you want to get out, it's important to both think about what you want to do, whether that's in a new industry or field or a different position, but it's also important to know what you don't want to do. Inverting that idea is powerful because it eliminates things that may seem tempting on the surface but may not fit your interests or skills or experiences.

There are two particular people in this book that went through that exercise and found it really helpful. One is Mia Dell, she's a policy director at SEIU. Another is Jessica Medina who is an Accredited Financial Counselor. Both of them were in litigation roles. Mia was in housing court in New York City. She was representing tenants, I believe, and then Jessica was at the SEC. She was at a Biglaw firm before that.

But both of them realized that they weren't adversarial people. They could go into the courtroom and put forth a very compelling and coherent legal argument, there's no doubt about that, but they didn't necessarily enjoy that. When they were thinking about things they wanted to do outside of their current line of work, they realized that they didn't want anything that was that adversarial or argumentative. I think that was really helpful for them to eliminate some seemingly appealing career opportunities.

If you're a lawyer, especially if you're a litigator, you can apply that same exact framework. If you don't enjoy the combative nature of litigation, then try to avoid that in whatever else it is that you want to do. But having this framework of knowing what you do want to do I think is pretty important and it's overlooked by many people.

Then another key takeaway is to really avoid premature optimization. It's this idea that you want to evaluate your assumptions basically up front before you're investing more time into something. An example of that was from Tiffany Duong who is a journalist and activist. She was working at a Biglaw firm. She quit after going on this amazing trip to the Galápagos Islands and so she was trying to think of what she wanted to do next.

She thought that she wanted to become a marine biologist but to test that assumption, she went into the Amazon and did some field work because apparently, to become a marine biologist, you have to do a lot of field work. She discovered throughout that process that field work was absolutely something that she did not want to do, it just wasn't for her. Because fieldwork was such an important part of becoming a marine biologist, she discovered that marine biology wasn't for her so she transitioned to a different route.

I really think that this idea of premature optimization is important. Basically testing your assumptions before committing to a new line of work is really key. It helps you save time, you don't waste any time, you don't waste any money, and it helps you get closer to what it is you actually want to do.

Sarah Cottrell: That's so true. I also wanted to mention, for people who are listening, that Tiffany and Jessica have both been on the podcast so if you're interested in hearing those episodes, you can always go and check out the show notes. For both of those, they both talked about some of the process, Adam, that you were describing.

I think to your point, people often do think like, “Oh, I need to figure out what I want to do, what I want to do,” but actually the process of elimination is very clarifying, often more clarifying I found for many people than trying to specifically find the thing immediately. Because as you eliminate things, it's not just the eliminating of those things, it's also realizing like, “Oh, I thought this thing might be a fit but here are some reasons why it really isn't,” and then you can have that framework as you're looking at other things and some metric to judge things against like, “Okay, I think I might like this other thing but does it really match up to what I now know about myself and what I'm really interested in doing and what I really want my job and my day to day to look like?”

Adam Pascarella: That's so true. I'm not sure if Tiffany said this in your interview with her but she was all about collecting data points. She just wanted to collect as much data as possible when navigating her post law journey, and that included things she liked and things that she didn't like. Like you were saying, understanding the things that you don't like really helps you get closer to what you want to do, so I highly, highly recommend that for your listeners.

Sarah Cottrell: Yeah. I was going to ask, I think you said you spent about three years writing this book, is that right?

Adam Pascarella: That's right.

Sarah Cottrell: Okay, and you said that the process of writing the book for you was also part of your process of figuring out what it was that you wanted to do next. Can you talk a little bit about how those two things played together and how you ended up doing what you're doing now?

Adam Pascarella: Yeah, definitely. The process of writing the book, number one, I realize that action is everything. It's so easy for me or you to say that but it's almost like you have to come to that realization yourself that you can analyze this decision to death but you aren't going to get much more clarity unless you take a step forward. The process of writing this book was one step forward in me on my journey out of the law into something else.

This book was a side project. I worked on it on nights and weekends. It wasn't my full-time gig. But speaking with individuals in the book made me realize that, “Hey, I do want to get more into finance and investing.” One of those individuals was Anthony Scaramucci. Now, granted, you may not agree with his politics, but putting his politics aside, I think he was a fascinating individual and he inspired me to go down my path.

He wasn't the main inspiration, I'd been thinking about it for a long time, but he's had an unbelievable career. He went to Harvard Law School, a lot of people don't know that. He went to work at Goldman Sachs and was fired from there famously and went back to Goldman in a more of a sales role which fit his skill set. Then from there, he decided to take the leap and become an entrepreneur and start his own investment management business.

Hearing his story and him do that was inspiring to me. Granted, I've been thinking about investing in stock picking for a long time, even when I was at Penn Law, I was focusing on my corporate valuation skills, probably too much compared to studying for my exam, so it was something that was definitely on my radar but I needed some time to figure that out.

Going back to what I was saying a couple minutes ago, working with a career coach was also helpful. His words, experience, and inspiration helped me come to that conclusion. But yeah, the one benefit to me for writing this book was I got to speak with so many cool people that had done interesting things outside the law. It made me realize even more that I had to do something different because we have one life and we need to make the most of it.

If you're feeling that legal practice isn't entirely for you, now granted, there are so many variables at play including financial variables and other things like that, but if you feel like it's not for you, there is hope there. There are so many different potential paths that you can go. That's what I hope the book is used for when readers take a look at it.

Sarah Cottrell: Yeah. I think from the conversation that we had earlier, there are many options in between staying at your job forever or quitting today. My story, like I have shared many times, I practiced law for 10 years. By three years in, I didn't want to do it forever, but I really wanted to pay off my student loans and so I found something that worked better for me that for me, the job at the court of appeals was like if there was going to be a dream lawyer job for me, that was my dream job.

It was great in many ways but it still wasn't the right really long-term fit. But one of the things that it did was it got me into an environment that was more suited for me and it gave me the ability to work towards ultimately paying off my loans, which is basically what I did before I ended up leaving the law.

To your point, you can take steps in the direction of doing something different and better for you without it having to be like, “I'm going to blow up my entire life.” I mean if you want to do that, that's also fine too, I'm certainly not going to stand in your way, but my point is, and something that I think is really important to talk about in the podcast, is the fact that the incremental approach is frankly the much more common approach.

Most people, even if you don't have kids or a spouse, most people have some financial or other obligations, family obligations, health issues, other things that mean that they need to take an incremental approach. If that's you and you're listening, you're not the outlier, you're actually more of the norm when we're talking about making this kind of move.

Adam Pascarella: Yeah, for sure. In the book, there are plenty of stories like that. One of them is Melinda Snodgrass who's a very famous science fiction author. She was very interested in writing fiction novels and in the science fiction realm or niche, but she had to pay her bills so what she did is she wrote romance novels. In the course of writing this book, I didn't realize that romance novelists get paid much more than other types of novelists so that was something interesting.

She recognized that she had to pay her bills after leaving Sandia Labs which is where she practiced for a bit, so she did that for a couple of years and then started writing fiction novels and met some people in the fiction world including George R. R. Martin and was off to the races. A step back, or even a step to the side of your ultimate goal, isn't necessarily a negative if you're on the right path, it's important to keep that in mind.

Sarah Cottrell: Yeah. I think that's so true. Okay, Adam, as we're getting towards the end of our conversation, is there anything else that you would like to share that we haven't talked about yet?

Adam Pascarella: Really, one of the key lessons from the book also is be careful about following your passion. You've probably had this discussion on your show before, whether you should follow your passion or something else. I don't have a clear answer on that, there are compelling arguments on both sides of the debate, but I would just say be careful about following what it is you're passionate about.

One example from the book is Sander Daniels who's the CEO of Thumbtack. He was one of the co-founders of it. Thumbtack, as your listeners may know, is a local services platform. He told me he didn't grow up being passionate about local services, it just fell into his lap. That would be crazy if you're 10 years old, what do you want to be when you grow up? “Oh, I want to major in or work in local services.” That's just not a thing. But while working in local services with his co-founders, he became passionate about it.

I think that's just something to keep in mind, especially because lawyers that want to leave the field may be wanting to do something that they're more passionate about. Yes, I would consider what it is that you're interested or passionate about but be a little careful with that.

Sarah Cottrell: Yeah. This is a hugely important conversation we talk about all the time, figuring out do you really want to make something that you love your career or do you just want a career that makes more space in your life for some of these things that you love? Because I think a lot of lawyers do feel this pressure of like, “If I want to do this thing that I enjoy, it needs to be my career.”

Because it's often true that we're in this head space of like, “Well, that's the only way that I would get to do it,” and the reality is that there are lots of people who make space in their lives for all sorts of things that they really enjoy and love doing that aren't their jobs. It just can sometimes be hard to see that when you're in a profession like lawyering that can be so all-consuming.

Adam Pascarella: Yeah, for sure. You may be in a better position to pursue your passion staying as a lawyer or maybe even getting a less demanding job in the legal industry. Yes, it's very important to consider throughout all this. It's a huge debate, it's a huge, I don't know if dilemma's the right word, but it's a huge decision that people have to make leaving the law. Yes, you need to analyze all these things but on the flip side, I'll go back to it, action is everything. That's probably a good way to end it. Embrace action.

Sarah Cottrell: Yeah. I like it. Okay, Adam, if people want to connect with you online and/or find your book, where can they do that?

Adam Pascarella: Sure. Listeners can go to reversedinpart.com. You can find more about the book there. Then for me, adampascarella.com. You can find more about me, my LinkedIn, contact information, all that cool stuff.

Sarah Cottrell: Perfect. Okay. Well, thank you so much, Adam, for coming on the podcast. I really appreciate you sharing your story and sharing about the book.

Adam Pascarella: Thanks so much, Sarah. This was awesome.

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.