Leaving Private Practice Behind for a Career in Tech as a Data Scientist [TFLP163]

This episode features Greg Jacobs, who has successfully transitioned from the law into the technology industry as a data scientist, leaving private practice after 14 years. 

In this conversation, Sarah talks to Greg about the approach he used to move into a job that many lawyers are potentially thinking about without fully returning to school. You should listen to this if you want to start a fulfilling career in the tech industry.

You will learn the exact process Greg used to get his dream job and how taking the risk to trust his instinct brought him to where he is right now. Let’s get right in!

Going to Law School because It Seemed Cool

Like most lawyers, Greg didn’t choose law because he had specific reasons that made him think the law was a great match. He chose the law because he had taken some law-related courses during his undergrad as a finance major and liked those classes. 

After a year-long stint in the finance industry, he realized he wasn’t cut out for that world and wanted something else. Since one of his minors was political science and he had taken some law in politics classes, Greg decided that law school would be a great fit. 

So, he took the LSAT and got into law school in the fall of 2003 because it seemed like a cool idea. It also seemed like a great way to avoid being sucked into being full-time in finance. 

He didn’t think much about the kind of lawyer that he wanted to be. He just knew that he found the law interesting and tried it on a whim. 

Building a Career in The Legal Practice in Litigation

Greg’s first year of law school was spent reading and learning about how legal arguments are made and written. The different subject matters and figuring out legal reasoning and writing were interesting. He liked law school because he thought the way of thinking and putting analytical arguments together was very similar to how his brain works.

Even after the first year of law school, he didn’t have a specific kind of practice in mind. Despite his exposure to private practice during his internship at a smaller DC firm, Greg just went through the process of campus interviews to join firms because it was the natural thing to do and was going to be financially lucrative.

He got a summer associate position at a big law firm in DC. It wasn’t a dream of his or anything. It fits organically.

After graduating, Greg got an offer to join the firm where he was a summer associate, and that was it. He didn’t have to do much because he had been exposed to many practice groups and had committed to joining after graduation. Since he mostly did litigation and was groomed for it as an associate, he naturally became a litigation lawyer at the firm. 

Passion for Litigation

The firm that Greg joined was Dickstein Shapiro, which, at the time, was a very big policyholder side insurance coverage group. It was one of the firm’s biggest and most highly regarded groups. His group’s main job was representing companies trying to get money back from insurance companies under their various insurance policies. 

However, despite his busy and financially rewarding job, he had no real passion for doing insurance coverage law. Although he enjoyed getting exposed to different lawyers and working with them, he was trying to see if it was something that interested him or could be a viable long-term path. 

How Transitioning Out of The Law Started Making Sense

Initially, the work was intellectually stimulating because he was used to thinking things through. However, he started to feel burned out and never really found his path or niche at the firm.  

He never felt like, “This really excites me and I want to be the next lawyer that does this or that.” There was no one at the firm that he saw their career trajectory and wanted to emulate. He just felt like what he was doing was interesting, but because it was a lot, he started burning out. 

Over time, he just lost passion.

Greg realized that he couldn’t see a long-term path in private practice or where he could end up at the firm, or what type of work he could end up doing that he would love. He never really found that. 

Although he enjoyed writing legal briefs and the best arguments, law firms required lawyers to do more than that because not only did they need to be good writers and be able to get up in court and argue in court. They had to be good at business development and get new clients, which felt like taking on two roles as a lawyer and a salesperson bringing in new accounts. 

Greg felt like his activities were taking up too much of his time and making it hard for him to do other things. The firm demanded a lot of non-billable work on top of the billable hours required, so he couldn’t escape the fact that he would work crazy hours. He stayed on because he didn’t see any other types of lawyer jobs jumping out at him and making him want to transition. 

Like Greg, many lawyers stay on the legal path because they are making good money, and it’s tough to get off the familiar routine of legal practice. They think that maybe things will get better or their mindset will change. That makes it easy to get complacent in that place. 

Having Doubts About Leaving the Law

Even though Greg wanted something more interesting and challenging than the routine of the law, he still had to deal with the thought that if he left the law, it must be because either he couldn’t hack it or he was somehow deficient as a person.

He felt that if he deviated from the legal path, he was failing at life. He had the crippling thought that he wasn’t tough or good enough. 

After getting a lucrative job out of law school that allowed him to pay off loans and put him on track to becoming a partner, leaving felt like underperforming, it didn’t help that lawyers are naturally competitive and want to feel like they are advancing in their careers relative to their peers. 

Many lawyers can relate to that feeling that they will be out for good if they deviate from the natural path. However, only a few lawyers can pull themselves out of that wrong mindset, as Greg did.

It took a long time, but he finally caught himself out of that mindset and accepted that there were other paths to follow. He realized that being fixated on billable-hours requirements punished efficiency. He had to look for other tasks if he got something done faster than his peers.

It was annoying that if he got good at something and could do it efficiently, it didn’t change the fact that he’d still have the 2,000-billable hour requirement hanging over his head. It was so inconvenient that he started to ask questions and let himself look beyond what was comfortable. 

Leaving Private Practice for the Tech Industry

Greg started thinking about moving into tech after talking to his brother, a computer programmer with a computer science degree. 

During that conversation, he realized that, unlike the legal profession, the technology area had people from all different backgrounds and skill sets getting into it, not necessarily through formal schooling but just being self-taught because there was so much free information about it out there.

He was scared that he was only valuable to the firm to the extent that he could complete tasks. It was a problem because advancing technology meant that many of the tasks would be automated in the future, which didn’t fit the work-hour model that law firms operated. That made him gravitate towards technology. 

Finding that path and realizing that many people did it without returning to school broke him off the mindset that he had to be a lawyer. He hoped that there was a bigger change that would make him happy. 

After 17 years on the legal path, Greg finally left the law to move into tech full-time. 

Becoming a Data Scientist

After getting serious about getting into data science, Greg started researching his options. He found out that he needed to have some knowledge of coding before taking courses in data science. He found out that most professionals were using Python and decided to teach himself how to use Python by playing around with available resources online. 

From there, he learned the fundamentals before signing up for short courses online to improve his knowledge. Although these courses have more structure than random online learning, they aren’t like returning to school. He got a certificate in one of the courses before signing up for a boot camp where they helped professionals transition into different technology areas.

The boot camp covered more ground because it taught specific skills needed in different technology areas. In 12 months, he had the skills to market himself and get a data science position. This was less time than he thought he would need. 

There are so many free resources online that lawyers looking to transition can take advantage of. When diligently used, these resources will help former lawyers land their dream jobs in less time than they think, especially if they take the time to figure out what they want to do. 

Getting a Job in Data Science

Greg knew that it wouldn’t be easy, but he made the sacrifice to spend his nights and weekends learning to code. He found something that he was passionate about and stuck with it. 

He completed the boot camp in 2020 and got his certificate. After adding that to his resume, he was ready to sell himself as a capable data scientist to companies looking to fill positions. 

Greg finished taking the course during the pandemic and started applying. He got a position within four months and used LinkedIn to look for jobs. He would see a job posting and wouldn’t just submit his resume into the portal; he also sent cold messages to company staff within his network. 

This is important because a resume doesn’t jump out as someone trying to get into an industry from a non-traditional standpoint. So, to get a position that looked cool, he would see who was connected to the company in his network and find a way to get in front of someone who would pull his resume out of the pile. His networking skills and resume got him a job in four months. 

Leaving the Law Behind

Many lawyers, especially in private practice, are often shy about connecting with people and discussing things they are passionate about. However, transitioning into something more fulfilling requires these things. 

If you are interested in making the changes required to improve your overall happiness, you should join the Former Lawyer Collaborative. All of these things that Greg used to get his dream job are worked through with people inside of the Collab, especially cold emailing. 

If you’re struggling to find a path outside the law, Sarah is now working 1:1 with a limited number of clients. Together, you’ll work through the Former Lawyer Framework to help you discover what you want to do next. With the one-on-one sessions, you will get invaluable information to chart your path out of the law. These include personalized advice and help with your resume and cover letters. If that sounds good, book a call with Sarah to get one of the available seats.

Connect with Greg

Greg Jacobs on LinkedIn

Greg Jacbos on Twitter

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.

Hello everyone. Today I am sharing my conversation with Greg Jacobs. Greg practiced law at a law firm as a litigator for a number of years and in 2020, he transitioned into tech as a data scientist. I'm really excited to share Greg's story with you because some of what he talks about is how he retrained and got the credentials that he needed to move into a data science role without fully having to go back to school and all of that. because we all know that most of us who are lawyers who want to do something else are not necessarily looking to go back to school. There's often this belief that you are going to need to, but in many cases, you actually won't need to, then there are lots of different ways to approach that, especially when it comes to tech and that's some of what Greg and I talk about today.

I mentioned this to him in the episode but the process that he describes himself going through is essentially exactly the process that you are supported in going through inside of The Former Lawyer Collaborative. Down to some of the very specifics, we talk about cold outreach on LinkedIn. Anyway, if you want to join us in the Collab, you can go to formerlawyer.com/collab, and without further ado, let's get to my conversation with Greg Jacobs.

Hi, Greg. Welcome to The Former Lawyer Podcast.

Greg Jacobs: Hi. How are you doing?

Sarah Cottrell: I am great. I am excited for you to share your story, especially because you have moved into a job that a lot of lawyers tell me they are potentially thinking about. Can you introduce yourself to the listeners and then we'll go from there?

Greg Jacobs: Yeah, sure. My name is Greg Jacobs. I am a former attorney. I graduated from law school in 2006 and then I was actively practicing until 2020, right around basically the start of the pandemic. In the summer of 2020, I transitioned out of private practice and into the technology industry and more specifically as a data scientist. I have been a data scientist for a little over two years now, and have not been practicing, I fully left private practice and the law. I haven't practiced for a little over two years.

Sarah Cottrell: Congratulations. Let's go all the way back to when you were deciding to go to law school. What made you decide to go to law school?

Greg Jacobs: Yeah. That's an interesting question. I graduated from an undergrad in 2002. I was a finance major and I knew my heart wasn't into finance. One of my minors was political science and I took a law in the politics class as a non-business, core business elective, really liked that class. I took a philosophy of law, so all of my non-business courses in undergrad, I used to touch on the law and I really enjoyed that. I thought in the back of my mind that law school would be a good fit for me.

I tried working in the finance world for a year. That just confirmed my suspicions that I wasn't really cut out for the finance world and so then I took the LSAT and applied to law schools and ended up going to law school in the fall of 2003, basically just on the whim of I like these law-related classes in undergrad. This seems like a cool path. I'm going to try it. I didn't want to get sucked to being a full-time in the finance world. I didn't really have much more of a thought of what kind of lawyer or anything I wanted to be, just generally I had an interest in the law. That's how I ended up in law school after a year of working.

Sarah Cottrell: I think that's a time-honored and well-worn path. For sure, for a lot of people who I interview on the podcast, there's some combination of “I took these classes in undergrad that were related to the law and they were interesting and either I wasn't exactly sure what I wanted to do with my undergrad degree or I started working in the field that I intended and was meh and ended up back in law school.” It sounds like from what you said, it wasn't necessarily that you felt that there were lots of specific things that made you think, “Oh, the law is such a great match,” it was maybe a little bit more just feeling like, “Okay, this finance thing isn't for me, so let me move away from it to something else.”

Greg Jacobs: Yeah, and when I was trying to figure out I know I don't want to stay down this path, one of the things that interested me were those classes from undergrad and they were all law related so I thought it was a natural match for me to try the law route and that obviously entails going to law school for three years so I gotta make that choice.

Sarah Cottrell: Yeah. Tell me when you got to law school and you were in law school, did you feel like, “Hey, this totally confirms my thought that this would be a good match”? Were you like, “What the heck am I doing?” Was it somewhere in between? How did you feel about the decision once you were actually there?

Greg Jacobs: When I got to law school and started learning, first year is obviously just a ton of reading, a ton of understanding how legal arguments are formulated and written. You just read a bunch of cases. I actually really enjoyed that part of law school. I actually really enjoyed law school. I thought that that way of thinking and putting together analytical arguments and stuff like that, I think that's just how it really was in tune with how I just think in general and how my brain works.

When I was in law school, I really enjoyed learning the different subject matters and just figuring out legal reasoning and writing and all of that, I found really interesting. I more or less enjoyed it. I enjoyed first year. First year is obviously a lot of work and you're just in the library 24/7 but in terms of what I was learning, I really enjoyed it. I didn't really have regrets about going to law school and it felt like a good path for me, at least when I was in law school. Because like I said, I naturally think about things the way lawyers do so it was a good match in that regard. I generally had a pretty good experience in law school.

Sarah Cottrell: You mentioned that you didn't have a specific type of law or type of legal practice in mind when you went to law school. As you were going through law school, did you develop an interest in doing something specific? Were you still just like, “I'm just going to be a lawyer and we'll see what that looks like”? Can you tell me a little bit about that?

Greg Jacobs: Yeah. Like I said, I wasn't going to law school to be a particular type of lawyer and then obviously, the first year of law school, you just get inundated with everything, you're not really focused on the particular area of the law, you're learning basically the core subjects that are going to be on the bar and that kind of stuff. Even after the first year of law school, I didn't really have a particular idea of what I wanted to do. I actually got a pretty good opportunity to just intern at a firm. I wasn't going to law school in Washington DC so I had a smaller DC firm where I was just doing research projects for them. I got a little experience or exposure to private practice.

That stuff was interesting. It was niche projects and I obviously wasn't working a ton of hours, it was [inaudible] I could get through a lot of pressure or expectation on me. Then when it came back to the fall of my second year, I just basically just went through the on-campus interview process and basically I didn't really know what kind of lawyer I wanted to be leaving law school but I knew I might as well interview with all of these firms that if you can get one of those, it'll be a good learning experience. It obviously is financially lucrative. So I just went on that path because why not?

I did that and ended up getting a summer associate. I got offered a summer associate position at a biglaw firm in DC. I just went down that path organically. It wasn't a dream of mine or anything. It just naturally fit me. It felt like it made sense as the next step for me.

Sarah Cottrell: Yeah. People have described it on the podcast before as like a conveyor belt. You just get on it and then it just keeps on rolling. Now I understand, so you graduated in 06, I graduated in 08, I realized there are people coming out of law school in more recent years where that's not as true as it used to be. but certainly for people of our tenure, there was an element of you just get on the OCI conveyor belt and go.

You weren't like, “This is the job for me,” but some people at this point already are like, “Oh no, this might have been a terrible mistake.” Talk to me about you graduate from law school and you go to work at this large firm, how was that experience for you?

Greg Jacobs: Yeah. I ended up joining the firm that I summered with after my second year of law school. I got an offer and I joined there in the firm. They try to expose you to as many practice groups as possible during the summer and they made us commit to a group joining the firm. I got a lot of exposure. I did mostly litigation projects during that summer. I wish I had done a few more non-litigation. I guess because I enjoyed reading cases a lot, I figured I would just go the litigation path. I probably should have given it more thought because that was a very clear path in the firm is are you going to be the transactional lawyer, are you going to be at litigation lawyer? I was groomed by the firm to join the litigation group

Then the firm that I joined was Dickstein Shapiro which, at the time, was a very big policyholder side insurance coverage group, so basically the group represents companies trying to recover under their various insurance policies from insurance companies. It's covers a lot of litigation with insurance companies. That was one of the biggest groups at the firm and one of the most highly regarded groups at the firm.

Honestly, I had no real passion for doing insurance coverage law but I really got along with a lot of the lawyers in that group that I got exposed to and enjoyed working with them. I basically just chose that based on just my couple months experience at the firm when I was summering. I ended up starting at the firm in the insurance coverage group as a litigator out of law school. It was doing the normal junior-associate litigation work where it was a lot of discovery, requests drafting, and legal research projects in support of more senior lawyers that were writing motions or some sort of filing in court and a bunch of document review too. It was the classic junior-associate task that I was getting assigned.

That was fine. It was a lot of work but I was also making a lot of money so I felt like I should be working this hard to make that money right out of law school. I just had my head down for a while working and I like the work well enough and I felt like I was just learning a ton and just trying to get exposure for as many different types of projects as possible to see, “Is this something that interests me? Is this going to be my long-term path?”

I think at first, the work was intellectually stimulating and like I said, I naturally think through things, legal reasoning makes a lot of sense to me and analytical thinking and so I enjoyed that and I think I just gradually started to just feel burned out and then never really found my path or my niche at the firm where like, “This really excites me and I want to be the next lawyer that does this or that.” I didn't meet anyone at the firm that I saw their career trajectory that I wanted to emulate. It was just I'm doing it, it's interesting but it's a lot and I'm just burning out. I think I just lost passion for it over time, if that makes sense.

Sarah Cottrell: Yeah. Going all the way back to what you said about how you chose litigation, first of all, very relatable because for me as well and for many people I've interviewed, it was basically like, “Well, I like research or reading and writing. These cases are interesting. They take place in court. I guess I should be a litigator,” and then the actual experience of being a litigator obviously includes some of that but also lots of other things.

It sounds like for you, there was a process that was like that, and it's not like you went into it thinking like, “I am going to love every moment of this and that's why I'm choosing it,” so I can see how, as you describe your experience, at least at first, if you're feeling some burnout or dissatisfaction, I would imagine it wasn't necessarily like, “Oh, something is horribly wrong here,” in the sense of you weren't necessarily anticipating it to be like, “This is all I've ever wanted to do, insurance-related litigation.”

Of course burnout amongst lawyers is rampant and there's more awareness around it these days but there's still a lot of focus on what individual people can do as opposed to the ways in which the law firm system contributes to burnout. Can you talk to me a little bit about how long do you feel like you were experiencing this before you realized like, “Oh, maybe this is a thing that I should actually pay attention to?

Greg Jacobs: Yeah. I probably would say I didn't really think about it too much, like I said, when I first started because I felt I was just learning so much and I was still relatively young and had the time and the energy to dedicate to it. I think what really resonated with me is, like I said, I was struggling to see my long-term path in private practice, where could I end up at the firm or what type of stuff could I end up doing that I could see myself really loving doing long term. I never really found that.

I guess the thing that I liked most about lawyering was writing legal briefs, filings, and the more sit at your desk, let's synthesize all these cases and write the best arguments for our position. I really enjoyed that but there wasn't really a path at the firm where you could just be that person because I just feel like law firms in general just require their lawyers to do more than that you don't necessarily specialize because not only do you need to be a good writer, but you also need to be able to get up in court and argue in court.

You also need to be good at depositions. On top of all of that, you need to start building your own clients. That's ultimately what I was seeing. No matter what path that you take, you need to be really good at these skills but you also need to be a business developer, which to me, coming from the business world, felt like almost two roles because a lot of companies that are set up have a sales team but then the sales team brings in the new account or something and passes it off to the account management team or however the business is structured.

They don't tend to also do all of the work. That's when I first noticed that that felt too much to me and I was like, “No matter where I go in the firm as an attorney, that's always going to be on your plate. There's always going to be all this substantive work, and then on top of it, the business development stuff. That's going to monopolize my time to the detriment of other aspects of my life.”

As I got older, I just felt the burnout from that because it's just a lot. The firms require so much of the non-billable work on top of your billable hour requirements that there's just no escaping the fact that if you go this route, you're going to be working these crazy hours, whether you can bill those hours for the client or not. I think I knew fairly early on that that was always going to be the case and I just stayed on the path honestly because I didn't really see any other types of lawyer jobs that were jumping out at me and made me want to really transition out of private practice to those jobs because I didn't really know that much about them and you just have your instincts of what really sounds exciting to you.

None of the legal positions really resonated with me. I just stayed on the path because again, you're making good money and you feel like, like you were saying, you're on this conveyor belt and it's really tough to get off. I was just plowing forward thinking, “Well, maybe it'll get better, maybe my mindset will change, or maybe I'll find something,” and it just was probably a little bit complacent in that respect.

If I could go back and do it again, I would be more proactive in trying to make a change sooner because I knew very early on that I was going to burn out and I was losing my passion for it. It took me a long time to do something about it. I think part of it is just the firm culture where everyone's doing the same thing where they're working lots of hours and stuff but you're achieving and you're making all this money and everyone's on the same conveyor belt and no one really knows how to jump off.

Sarah Cottrell: Yeah. It's interesting because you mentioned looking around and essentially realizing, “Oh, there's no one here who's senior to me whose career I want, in the sense of a type of law that I could see myself or a type of practice really owning and being mine.” So many lawyers have shared that experience of looking around and being like, “I do not want the life of anyone here who is in a position that I'm supposed to be aspiring to.” That can be for lots of different reasons.

But I think to your point, there's a big difference between the substantive legal work-at-your-desk type of stuff, the standing-up-in-court deposition stuff which listeners of the podcast will know, no, thank you, I would rather never do that, the end. I also was a litigator. Then there's also the business development like you said. but then also if you get promoted to the partnership, there's also the managing of people. It’s all of these different skill sets that are wildly different and you're not really developing all of those as a junior lawyer, but then the expectation is that if you become a partner, all of those things will be happening.

To your point, I think there are a lot of people who feel like, “Well, this piece of it is okay but I don't really want to do that other piece of it like business development,” or people who don't really think about, for example, the managerial aspects and that's one of the many reasons why law firms tend to be run so terribly because many lawyers are terrible managers because they have not actually been selected for their positions due to having managing of people's skills.

Everything that you shared is such a common theme on the podcast, including what you said towards the end which was just you knew it wasn't really working but you didn't have a clear idea of what you would go to and so you just went along hoping things would improve in some way. I know for me that is 100% true in my experience and there are so many lawyers who talk about that happening, especially because law school, passing the bar, etc., is such a “Here is the process with the steps laid out,” and deviating from that just feels such a wild turn that it can feel like, “Well, that can't possibly be the right answer.”

Greg Jacobs: Yeah. I think there was a little bit more of not only could that not be the answer, but if I were to deviate from this path, I'm failing. I'm not tough enough, I'm not good enough. You're right, in law school, you come in and your path is very defined for you. It's like for first year, just really focus on your grades and get really good grades because if you get really good grades, then you'll get one of these more opportunities after your second year of law school to be a summer associate at a firm and then you can get that job. You'll be on the path to paying off your loans because you'll have this really lucrative job right out of law school.

It was very much defined and then when you're at the firm, you're with other people that have gone down that path and then it felt like the only way now everyone needs to just be focused on making partner. Partner is like the holy grail and if you don't make it, that means you somehow failed or you weren't cut out for it. I feel like it was very much like that mentality. I struggled a long time with that because most people that go to law school, I think we're all wired where we're type A personalities, competitive people, you want to feel like you're achieving relative to your peers and the firm very much puts this making partner on the pedestal.

I felt like, “Oh, well, I don't see very many more senior lawyers or senior partners at my firm where I feel like I would be thrilled doing what they were doing.” But at the same time, I wasn't focused on, “Okay, so what am I going to do instead?” Because I felt like if I deviate off this plan, I'm somehow taking myself out of the game or I'm failing. It took me a long time to even catch myself doing that and be like, “Well, no, that's just the wrong thinking. There are other paths.”

I would talk to classmates of mine from law school or people on similar top points in their career at other firms and they were all feeling the same thing where “I don't know if I really want to do this, but I've already invested all this time and effort into it. Am I quitting on myself by going a different route?” It was very tough for me to get out of that mentality if that makes any sense.

Sarah Cottrell: Oh, yeah, 100%. One of the things that I would say almost all of my clients talk about is having to work through this feeling of “If I leave it's because I can't hack it.” Almost the sense of “Well, no one would just choose to not do this because obviously, this is the correct choice. So if you leave it must be because either you can't hack it or you're somehow deficient as a person.”

Those things aren't true but I think, like you said, there are so many things about the legal industry as a whole and also the personalities of many of us who are drawn to law school that feed together to really create this feeling that, like you said, in many ways it's almost subconscious, it's not like you're even consciously thinking about it but you also don't really question it.

Can you talk a little bit about what brought you to that point of actually realizing like, “Oh, this is how I'm thinking, and actually that's not true”?

Greg Jacobs: Yeah. For a long time I was trying to identify what specifically about the law firm job I disliked and then try to identify other legal jobs where my biggest dislikes wouldn't be present. For a long time I was like, “Oh, well, I want to try and go in-house,” because the thing that I was fixated on about law firm life was these billable-hour requirements, it felt like almost punished efficiency. If you could get something done faster than your peer, then you have to go find other work.

I was getting annoyed by that because sometimes I would get really good at something and do something very efficiently, but then that doesn't really help because I still have this 2,000-billable hour requirement hanging over my head. I almost felt like it promoted you to milk your projects and be as, not inefficient, but it wasn't incentivizing extreme efficiency which was really something that bothered me.

I was like, “Well, if I go in-house, then I could still get to think through these complex legal disputes and issues but I'm not necessarily having to bill all these hours.” I just had it in my mind that if I could just move in-house, I would be happy. For a while, that was my focus and I interviewed for some in-house positions. I just never landed that job. I got through a bunch of interviews and I was always one of the final candidates but it never quite just worked out.

Now in hindsight, I'm happy that that happened because I think it would have deferred me from getting really serious about questioning more fundamental questions and giving myself permission to be like, “Well, maybe you don't even want to be a lawyer at all.” That creeped into my mind over time. I think I always knew that there was something bigger going on in terms of, like I was saying, it was more giving yourself permission to think that big of a change.

As lawyers, we're very risk-averse and it seems very risky and very much like, “Oh, I'm giving up,” to say, “Oh, maybe I don't want to practice law at all.” But what helped me is my brother is a computer programmer, he was a computer science degree so I talked to him a little bit and I just noticed that unlike the legal profession, the technology area had people from all different backgrounds, all different skill sets getting into it, just not necessarily through formal schooling but just being self-taught because there was so much free information about it out there.

With the efficiency thing that was bothering me, the other thing that was scaring me about the way my firms were set up was, again, my value to the firm was tied to how much I worked and the hours that I bill and I see the world is just becoming automated. Tasks that I was doing as a junior associate, the junior associates now aren't doing because a lot of it's been automated away like the document review or even just creating document requests. You don't start with a blank Word document, you can generate stuff.

I was watching areas of the law be automated away and I'm like, “Well, how is that going to work when the law firm business model was set up based on hours working?” I started gravitating towards technology because I was like, “Well, technology, you totally flip everything and you're trying to make things more efficient.” If you can build things that save people time, that's what the industry's trying to do.

I think it was finding that path and seeing that people in my shoes had done it without having to go back to school, that broke me out of the mindset of “I have to be a lawyer to be like, well, maybe there's a bigger change here that's really going to make me happy.” It was almost like finding that option or opportunity for another path. I didn't see a way out and once I saw a way out, like, “Okay, now I'm letting myself think maybe I don't want to practice law at all anymore.”

Sarah Cottrell: Yeah. I think that's such an important point because I will often have people get on my email list and we'll be emailing and they'll say, “Yeah, I really want to leave but I don't want to go back to school.” There is, I think still, especially for lawyers because obviously we're people who value education and did graduate level education, there is this sense of “Oh, I'm probably going to have to go back to school and I really don't want to do that so I don't really feel like I have options.”

To your point, realizing there are lots of options can be really helpful in terms of just making people realize that it's possible. How many years into your legal practice were you when you started seriously considering this move into tech?

Greg Jacobs: I would say I really started considering it, so my wife and I moved from the east coast to the midwest in late 2016, I think in the middle of 2016. We moved to the Milwaukee area and so I joined a regional firm out here where it was the same type of stuff, as a regional firm, it was a little better quality of life firm where I had a little bit less hour requirements. I had a more normal manageable number of hours. I was working a week where I really had some more time to focus on what else I should do.

I knew, in general, I'm interested in something in technology but I didn't really know what that was. I had a little bit of extra time. I was just spending time reading and researching. At that time I still wasn't like, “Okay, I can really make a change,” it was more just seeing what's out there in the tech world, and by tech, I just mean I was really interested in something to do with coding. Anyone I talked to that was able to computer program, it just blows my mind. I feel that they have magical powers or something and so I was like, “I really want to be able to do that.” Some of the stories you read about people that just build stuff from scratch, I was just really interested in that.

A lot of my early time was focusing on how feasible is it for me to learn those skills without having to go back to school. Just over time, I did a lot of research and just reading about “Okay, what is a path that could work for me?” I didn't really get serious about it until I stumbled upon specifically the data science area of the world because I felt like you need a lot of technical skills but it was also like you're using data to solve problems. If you go work for a company where you don't just use the data to build this model to solve the problems, you then have to convince the stakeholders to adopt it and where you have to be very practical about how can this fit into the business goals. That had a sense of “I've developed a lot of skills as a lawyer and I was a business undergrad, had a business undergrad degree, those skills would be very relevant to that type of job too.”

I found that niche where I'm not just totally bailing on some of my legal skills, I would still be having to use some of those skills but also I do need to learn how to code and get the technical skills. I just found that and I felt like that was a good fit for me. Once I found that particular role and I started researching more about that area of that industry or that area of the technology industry and saw people were getting into data science from all different paths, there wasn't a real set path to get into the industry, so then I was like, “Okay, this really seems like it's feasible because I don't need to have a data science degree or anything to get in, there are tons of people that have transitioned into it organically.”

Think of a snowball rolling down the mountain where it was like, “Okay, I know I'm interested in this broad area of the world,” and it got narrowed down over time just by doing research and reading, coming across people with their Twitter handles or their LinkedIn profiles and they seem like they have a cool job. It narrowed it down just by doing a lot of research until I found something that I really felt I would really be happy doing. Then once I was able to identify that, then I got to more concrete focus on, “Okay, now let's set up how do I do this? What more tangible tasks?” once I was focused specifically on the data science world.

Again, that's why I think what you've set up and how you're helping coach lawyers through that process is such valuable because I did that on my own and it took me probably a lot longer than it should have. I think it's such a valuable service because, like we were talking about, it's so hard for lawyers to even envision doing something non-legal. So having someone who understands where you are and is trying to help you along the way I think is just super valuable.

Sarah Cottrell: Yeah. I feel similarly. I look back on my own path and I see a lot more flailing around than was strictly necessary. So you ended up fully leaving your job in 2020, your lawyer job. You talked about you got to the point where there are some tangible things that you knew you needed to do in order to make that shift, can you tell us what those were?

Greg Jacobs: Yeah. I would think by 2018, probably late 2018 I got really serious about specifically, I was like, “Okay, this data science world seems really interesting to me. I think I would really enjoy it. Let me figure out and then research it. Okay, it is feasible.” It's around that time I knew before I could even venture down courses or curriculums specific to that job, I just needed to know how to code and so it was more just general, this is a prerequisite. I need to have fundamental programming skills in order to even start down that path.

So I researched and most data scientists are using an industry or using Python and so I was like, “Okay, I'm going to teach myself how to learn Python.” I started that late 2018, maybe early 2019. There's so much free online tutorials and stuff. I just started playing around with that stuff and trying to figure out how that all worked. That was my step one was just to build the fundamental programming skills.

I did that on my own. There's so many resources out there that are completely free that will teach you how to program basic things and teach you the fundamentals without costing you anything. I did that and then as my skills progressed, I would say I was learning the fundamentals and then from there there are websites set up out there that you'll sign up for a three-month course or a two-month course that will teach you.

There's a little more structure but it wasn't fully going back to school. It developed over time to where like, “Okay, I'm doing this. I like it. Let me take the next step and sign up for this course.” I'll get a certificate at the end of that and then ultimately, the thing that I landed on was that there's a lot of what they call boot camps that are set up where it was set up for people that are professionals that are looking to transition into different areas of technology. Their programs are set to give you all the skills that you need to get a job in a certain area of tech. Those are more comprehensive.

You do a deeper dive into whatever area you're interested in but you need to have some of the baseline skill, programming skills already under your belt in order for those programs to make sense. That whole path was, I would say, all in about 12 months, which if you really think about it, it's not really that long. I was still working full time so I was just doing this an hour or so at night and then over the weekends and stuff, so basically outside of business hours.

I was able to get through it. In about 12 months' time, I had the skills to market myself and get a data science position, so it didn't take me as long as I thought it would. Technology is just a whole different world because there's so much open source materials and everything out there that anything you want to learn you can learn, that you can find materials to teach yourself for free or for very, very little amounts of money.

It really is amazing to me how much people put out there for free, how valuable it is out there in the open source world. I don't know if I answered your question but it was a little over a year, I would say, from the time I got really serious about it to the time when I was interviewing for non-legal positions.

Sarah Cottrell: Yeah. I think one of the things that your story illustrates really well is it can go pretty fast, especially if you take the time to figure out what it is where you're like, “Okay, yes, this is the direction I want to go,” because I think a lot of times people feel so much anxiety about moving into something that they skip the whole actually determining this is the direction they want to go and they move straight into a course or something like that. but there isn't that certainty of “I actually have done the work to know that this is what I want to be doing,” and so then there isn't necessarily something that is a fit and so they don't continue. It can make the process feel like a lot longer, whereas when you do get that clarity, to your point, 12 months, especially when you're talking about in the grand scheme of things, is really not very much time. Talk to me about getting the data science job, leaving the firm, and what that was like.

Greg Jacobs: Yeah. Like I said, I knew I was on the path and I don't want to say I just woke up one day and was like, “I don't want to be a lawyer anymore,” and within a year I wasn't a lawyer. There were a lot of struggles. There was a lot of upfront struggle. but that's the most difficult and the most important process. You have to fight through it because in order to do it, I think you have to really find something that excites you. To continue working as a lawyer and then also trained to teach yourself how to code on nights and weekends and stuff, you have to find something that you're really passionate about and then it doesn't seem so bad.

I definitely think I can really resonate with flailing around and not really know where you're going. It's important to figure out, you really do that work up front to figure out what you really think is going to make you happy. because then when you're on that path and you're making that happen, it really doesn't feel like work. You're really excited about it and you're really passionate about it. but to answer your question, it was around the spring of 2020 when I finished my more comprehensive boot camp course. They certified me as ready to go out there and they gave me my certificate. I could put that on my resume and sell myself as ready capable of doing these data science roles to these companies.

It was a really interesting time because spring of 2020 was when the world was shutting down. I think I finished my course in March so literally my firm went completely remote. I was working completely remotely while I was looking for positions. That part I think because I did so much prep time up front, from the time I started applying, I found a position within four months. I think I got lucky in a sense but I understand over time as a lawyer, I built up my LinkedIn profile and you learn how to use LinkedIn to really help you look for jobs.

Obviously, I would see a job posted and I wouldn't just submit my resume into the portal and keep my fingers crossed because, especially as someone trying to get into an industry from a non-traditional manner, your resume isn't really going to jump out, so it was a lot of finding a job position, a posting that looked cool and then seeing who in my network maybe was connected to someone at that company or finding a way that I can get in front of someone who would pull my resume out of the pile I think was a lot of the reason why I was able to get interviews.

I think that's really important but it's also something that us as lawyers, a lot of especially in private practice, we're very used to connecting with people on LinkedIn and posting and stuff like that that's not necessarily intuitive to other industries and really use that to your advantage, and don't be shy, reach out to people, connect with them. People are definitely, especially when you're asking them for help, or you want to join their company and that they're passionate about, so many people are more than happy to help you out or put you in touch with the right person and stuff.

I think I really used the networking skills to good use there. but really I was looking for jobs that I thought looked cool and then obviously crafting my resume to highlight the skills that I had that match the job description, but then just trying to connect with people and get in front of the HR person that's going to pull my resume and get my foot in the door for the interviews. It was a crazy time just because of everything that was going on in the world. but I think to a certain respect, that helped me because everyone was going remote so I wasn't tied down that more and more jobs are being posted for remote postings.

That opened some more doors for me though the job I ended up finding here was local. It was just a lot of cold emailing or cold connecting on LinkedIn and networking. I finally felt like I put in all this work and this was the light at the end of the tunnel. The actual job searching wasn't as dreadful and stressful as it normally is because I really was looking to make this big career change that I thought was really going to improve my overall happiness. That part was actually not as stressful as trying to actually develop the skills to make the move.

Sarah Cottrell: Yeah. Well for people listening, literally all of these things that Greg is describing that he went through in his process, this is exactly the process that I work through with people inside of the Collab, and especially you mentioned cold emailing, which I probably have talked about in the podcast before, but I am not someone who's like, “Oh, cold outreach, that sounds fun,” but also it's really one of the most helpful things that you can do in this process, both when you're getting information and then ultimately, like you were describing, when you're actually pursuing positions.

Okay, Greg, as we're getting to the end of our conversation, is there anything else that you want to share that we just haven't had a chance to get to yet?

Greg Jacobs: Yeah. I think we've touched on it as we went through, but I think the main thing that I would say is just for people that are feeling similar feelings that I've described on my path, don't ignore them. I think that my biggest regret or mistake was to not trust my instincts sooner. Your intuition is almost never wrong and so if you're having these feelings that something is just not right, your head's not into it, or whatever concerns you're having, really take the time to try and get in tune with yourself and pay attention to that because that's ultimately going to lead you on the path that's going to make you the most happy.

It may be a path that you were considering, feels impossible, or super stressful, whatever, just embrace those feelings and work through them. Take the time to really listen to your gut because ultimately, that will guide you on what path makes the most sense for you and what's going to make you the most happy. Don't just push it aside because it maybe wouldn't be the path that a lot of your colleagues are going to select, especially for people that are in private practice I think at law firms because you spend so much time there and you're around people on the similar path. Understand that it's almost like selection bias. You're completely surrounded by people that have chosen to stay on the law firm path so they're always going to be heavily biased towards staying at the firm and not understand if you have thoughts or desires to take a different path.

Just listen to your intuition and don't necessarily shy away from challenging yourself to maybe take bigger leaps than you thought maybe would be possible at first.

Sarah Cottrell: I'm just going to co-sign all of that. I think developing the ability to trust yourself is one of the most important things that you can do in this process.

Greg, I really appreciate you joining me today and sharing your story.

Greg Jacobs: Yeah, sure. Thanks for having me, Sarah. I really enjoyed the discussion.

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.