One Career in Three Acts: Big Law, Contract Work, Plaintiff Firm

Katya Valasek:

We're joined today by Charles Star, a lawyer whose career has moved between Big Law, comedy, and contract work before landing in a plaintiff side role that finally fits. Charles, you started law school with social justice work in mind. What drew you to law in the first place?

Charles Star:

It's a complicated question. My intent when I started was very much to be a union-side labor lawyer. My parents were both union members. And so growing up in a household, even one that was, you know, arguably like professional, my dad had a college degree or whatever, you are around pro-employee activism. And so that's how I kind of wanted to go to law school. But I mostly went to law school because I didn't know what to do with my life, right? I graduated college. I spent another year in college getting a public administration degree. And then I found myself kind of at sea because there wasn't any specific thing I wanted to do.

And I applied to law school thinking at the time either academia or union side labor work. And then as graduation approached, I didn't want to rely on my parents' money. And you know, I didn't do well enough to be an academic. Let me be clear about that up front. I had squandered any hopes of a future in academia by the end of my first semester of my first year. But I didn't go the union side legal path because I was a coward, I suppose. I did not put my heart into it and let the golden handcuffs guide me. And so I went to big law right out of law school.

Katya Valasek:

So tell me more about how you ended up at big law, because for many people, that's their dream and they have a hard time getting there. And you make it sound like you just sort of fell into it. So at what point did you reach that crossroads where you decided to take the path that would lead you to big law?

Charles Star:

This is such an obnoxious thing to say, okay? So know in advance that I know how obnoxious this is. The path was set out for me as soon as I took the LSAT, because I went to Columbia. And at Columbia, you don't have to do... First of all, it's very hard to do poorly because it's not a mandatory curve. And so it's like you have to really eat shit to get a C on an exam, which is not, as I understand it, the case in most of the law schools in America. You enforce a hard curve and people are getting real hard lessons if they don't put the work in. And that's just not what the hardest to get into law schools are like. They create a big safety net for their people.

And then once on-campus recruiting starts, there are more opportunities than there are people who have the pedigree of a top law school credential. Like I said, I didn't do well enough to get an academic job, and that also means that I'm not going to Wachtell or Cravath, top of the market of big law, but there's a lot of big law in a big city. And so I ended up with a job coming out. I got a 2L summer job and I got a job coming out of law school. And so that's it. I loved law school, but I had an OK law school transcript and that's enough because of the name at the top of the transcript, not mine.

Katya Valasek:

When you took that job, when you accepted that offer, did you see big law as a detour in your career or was that the plan in the moment?

Charles Star:

Detour, detour. But I didn't have an exit plan at all. I mean, I ended up at a firm, you know, I interviewed with this firm and that firm had a management side labor practice. And I was very clear in my interview that I was a union guy and they also had an employment, you know, it's also employer side, but an employer side employment law practice, which is different to me, really, because that's based on individual circumstances more than it is about the material relationship between management and labor. And one of the partners was like, look, if you will come and work in the labor and employment department for the summer, we'd love to have you. And I split my summer, my 2L summer between that firm doing essentially employment law, because I really was not going to do anti-union work.

And I worked at the NLRB in the contempt litigation branch in DC for the other half of the summer. And then they made me an offer and I accepted it contingent on the fact that I would not be working in the labor practice. I worked in the litigation group because I consider big firm litigation 99% of the time to be two litigants, neither of which I care about. It's like two big companies fighting over a pie that I have no real dog in the fight of. And so litigation seemed bloodless to me. I don't care. I wouldn't work for a landlord evicting people, but if Microsoft is suing Google, who cares? There might be individual issues I care about. But in general, the fight is I'm just being a backbencher clerk. And so that's how I rationalized it to myself.

Katya Valasek:

How long were you able to go in and do the work even though you weren't emotionally really invested in what you were doing?

Charles Star:

I lasted a year at the first place. I then left because I really didn't like it at all. And I went to a smaller firm that did commercial litigation work. And I was there for four years. I really liked the people, but didn't really like the work anymore. And then that firm broke up into a bunch of pieces when the partnership, you know, like there was a battle on Olympus and all of us in the village just watched the lightning fly. And I went with one partner to Proskauer. And the departure to Proskauer was at around the same time that my father passed away. And after being at Proskauer for not very long, because we stayed in our own offices until our lease ran out, basically, our group, I was like, I can't do this anymore. And so I just quit after a total year of being on the Proskauer payroll, but more like five or six months of being present in the Proskauer offices. And that was it.

Katya Valasek:

So you left a big firm for a smaller firm and then by chance ended up back at a big elite firm.

Charles Star:

Yes.

Katya Valasek:

Where it sounds like not only did you not connect emotionally with the work you were doing, but you lost that connection for your colleagues that you enjoyed being with at the smaller firm.

Charles Star:

Yeah, I mean, like I did some work still with my old colleagues, but now I'm just part of the system at this big firm. And I get staffed with people who I didn't know before, some of whom I liked a little, some of whom I didn't like very much. But in general, I just didn't like the atmosphere of being back at a big law firm. And so after a year, I was just like, I would rather try my hand at stand up, which is like another thing that I'd wanted to do forever. But now at 33, my life circumstance has said to me, just do it. Just do this thing because you don't like the thing you're actually doing.

Katya Valasek:

So what does it do to you when you day to day don't care about the outcome of your own cases, don't feel connected to the people that you're working with and are really unhappy in your work environment? How did that impact you?

Charles Star:

I was depressed. I probably gained a lot of weight. I probably took advantage of the perks, you know, fancy meals for free because they're being charged to someone else.

You're stuck late. You take a car home instead of the train and you sort of use those as a salve, I guess. But it made me miserable.

Like I always said, as a junior attorney, they pay you too much for the quality of your work and not enough for the quality of your life. And that's only that's a little self-aggrandizing because your life is better than, say, a coal miner and you're getting paid a lot more. But when you intellectualize your own life, that's kind of the conclusion you come to is that it never seems worth it. And but in retrospect, that's definitely true. I'm happier with less because my life is different.

Katya Valasek:

Well, you mentioned the salary and the concept of golden handcuffs earlier, which my interpretation of that is someone ends up in a job where they're getting paid so much money. Walking away is impossible because of the life they've built around them. They have a mortgage. They have a car payment. They're accustomed to a specific kind of lifestyle. At this point in time, do you feel like you were stuck in golden handcuffs?

Charles Star:

A little. I mean, I had bought an apartment. I had bought a car that I had car payments on. I had three years of law school loans. You know, I wasn't getting a scholarship and I went to Columbia. So it's a lot of money. Did I really have hold golden handcuffs? I don't know. I had the safety net of parents who could have floated me if I went completely bust. But you know, if you don't want to rely on that, then it does feel like golden handcuffs. And then it took six years to decide I can work my way out of this one way or another. And so it was that. And it's like, you know, it was honestly, it was as I was coming up on the year anniversary of my father's death that, you know, I was like reflecting on where I was in my life and did I deserve better for myself? And so that's why I'm like, here's the thing. Here's a creative path that I think I have some kind of raw aptitude for. Even if I didn't ultimately make it, I was just like, I think I have like the raw aptitude to be funny professionally. And I think even the pursuit and failure would be better than whatever this is.

Katya Valasek:

How did that career in comedy go for you?

Charles Star:

It depends on what your measuring stick is. If your measuring stick is, have you heard of me poorly? If your measuring stick is financial results, even worse.

If your measuring stick is, did I have enough highs to make it worth looking back on positively? The answer is absolutely yes. I enjoyed doing it immensely while I was doing it.

I loved going out at night and hanging out with other comics and doing open mics and book shows. And I did festivals in Portland and San Francisco. And I made Zach Alifanakis laugh backstage at UCB. And I performed with a lot of people who are famous now and who would recognize me on the street and probably remember me as a kind of funny guy who didn't put it all together and make it. So there's enough there. There's a lot of chaos theory, right? Butterfly flapping its wings and all that. I have no regrets. I quit something I didn't like and I did something I did like. And my current life is that I am a married guy with a son going off to college in the fall who never starved and is finding other ways to be creative. And so, yeah, it was 100% worth it.

Katya Valasek:

So when you think of the dopamine hit that you get from professional success, and when you compare getting that job offer after your summer associate position, so your first job out of law school, and you compare it to booking your first gig after you quit law, was there a difference in how you felt when you reached each of those accomplishments?

Charles Star:

I felt nothing when I got the legal job offer. I was already doing something that I expected not to like very much to pay off my loans. I felt literally nothing. And when I, because when you say booking your first gig, there are a couple of ways to think about it. There is putting my name in the hat for the first open mic I did, which was, you know, sort of thrilling to have done that. And there is the first time that one of my peers either invited me to or acceded to my request to do a show that was being booked for no money in the basement of an East Village bar. That was big. Like that someone would say yes after having seen me perform was much bigger, much bigger to me because I care about the outcome.

Katya Valasek:

And so during this time, did you have a side hustle to the comedy gig? Were you living off savings? How are you supporting yourself?

Charles Star:

Well, at the beginning, I was living off savings. But as I said, I owned my apartment, but I didn't own it free and clear. And I own my car, but I didn't own that free and clear either. Like I joke to people that I quit in part because I thought I had fuck you money. And what I learned very quickly is that I had no idea what fuck you money was. And I was burning through my money just insanely quickly. But when this happened, this is 2004, which is really kind of before the second, I suppose, dot com crash in Silicon Valley. And so I was hitting the legal market as someone with six years of New York commercial litigation experience and a Columbia diploma, which made it really easy for me to get contract work at the top of the market. I was getting a good contract attorney wage. And so that's how I paid my bills. It took me a few months to be like, OK, this is unsustainable and then get myself back in just being a document grinder in a room full of attorneys clicking buttons.

Katya Valasek:

So I actually want to clarify that because you said you were doing contract work. I want to make clear that that doesn't mean you were just reviewing contracts. What kind of work were you doing as a contract lawyer?

Charles Star:

Correct. You're doing discovery work. Either you are reviewing outgoing discovery for privilege and relevance, especially back then in 2004, there was less AI assisted. There was less negotiation of search terms like you would just like look at, you know, a financial manager's entire email archive and have to filter out the pornography that they shared with their peers. And so it's like that's not what contract work really is anymore because the process of negotiating discovery has changed so much. And the assistance of AI tools and other database management has changed it a lot. But back then you would just do a linear review of someone's entire work history.

Katya Valasek:

Essentially what you were doing was you were getting paid an hourly rate by a company that a law firm hired to support the litigation.

Charles Star:

Correct. Because you have to have a lawyer do this work to be responsible to your own clients. But you don't want no one wants associate level pay being done doing this. So you're hiring outside attorneys to do it at volume at a pass through rate to the client. I don't know what the ethics of markup are along the way, but the reviewer gets a wage. The agency is getting more than that. And then whether the firm bills a premium on that, I don't know whether they do or don't. I never really had access to that. But it's certainly cheaper than hiring a staff of associates to do the same thing, which would be absolutely cost prohibitive.

Katya Valasek:

So what did your day look like? You were doing discovery work by day and then comedy at night. How are you spending your time? How many hours were you doing the contract work?

Charles Star:

That's basically it. In 2004, it was a lot more tolerated to do like 40 to 50 hours a week. But that got harder and harder as they would want people to do the overtime so that they had to hire fewer people and it would be more manageable. So there was that. And then I would try to do three or four or more shows a week. And I mean, I met my wife at exactly the same time. And so it was better for my comedy to not be a lonely sad sack. But it also meant that I wanted to see this woman more than I wanted to be a seven-day-a-week open mic guy, which is better for my life, I think, but absolutely not better for getting better at comedy.

Katya Valasek:

And then at some point, you transitioned from doing contract work to a staff attorney position. How did that happen?

Charles Star:

It happened because one of the contract attorney positions that I got was not a purely document position. I had a background in antitrust from my time in big law. And I got hired at a white-collar defense firm that had a very antitrust-centric case. They were representing the executive of a company that was being prosecuted along with the company that they used to run for price fixing. And so I got hired into that job at a really premium rate for contract work. And then after that project ended, I ended up working off and on with that firm for years. And then the work kind of ran out, and I left and looked for other work. And then they brought me back for a specific case, and I was there for a year again after that case. I got staffed on other stuff, and then I left again and had other work. And then they brought me back again for another case. And in the middle of that stretch, I now had a kid, and I kind of wanted stability, and they had made other contract attorneys into staff attorneys. And so I requested being put on staff, and they eventually agreed. And I was there until the pandemic. And then in the middle of the pandemic, you know, with work declining and me not really working very much at home, I was let go during the pandemic. And then when I got laid off from that is where I ended up transitioning to plaintiff side work.

Katya Valasek:

So you pivoted after your stint as a staff attorney to your current role.

Charles Star:

Current role, not current job. What happened was I then had to look for work. I mean, I will say, I very much enjoyed being unemployed during the pandemic.

You know, you can't do anything anyway, and I wasn't really in the same, like, money-burning situation. Like, enough time had passed that I actually could now float a little. My wife, on the other hand, was like, look, you deadbeat, get back to work.

After I tried that for about a month. And so it's, of course, it's hard to find a job during the pandemic. And of all things, I ended up finding a job on Craigslist doing contract work for a plaintiff side firm.

I decided I would do that because it's very hard to go back and forth between plaintiff and defense side. But at this point, I was like, I'm just going to do it. I need the work, and I don't really care that much.

And I ended up getting a job at Robbins Geller, working from home. And so I did that, and it was a very good experience. And of all things, while doing that job, I got back in touch with one of my friends from the small firm at Big Law from like 15 years earlier, or whatever it was. And she was now a partner at Seeger Weiss, herself doing plaintiff's work. And she was like, oh, if you're doing plaintiff side work, just come work for me. And so I got hired at Seeger Weiss as a staff attorney instead of as a contract attorney. And so that's how I ended up where I am now, doing plaintiff's work and still working from home, but back working for people who I like working for. I also liked working for the people at Robbins Geller, let me be clear.

Katya Valasek:

So you're back working with colleagues that you enjoy. What about the work itself? Do you enjoy this more than the work you were doing at Proskauer, at your first big firm?

Charles Star:

Oh, yeah. I certainly enjoy the work more than I was doing at Proskauer. I feel more emotionally connected to it because there are different things that plaintiff's firms do, and everyone's got their own opinions about different styles of class action cases and whatever. What we do, or what I do for this firm mostly, is consumer class action work, where people are harmed by devices, by faulty car parts, that sort of thing. And that's very easy for me to have an emotional attachment to, in part from the plaintiff's side, but also in part just of the general anti-corporate bent, is that I have no love for the people on the other side. And so just kind of sticking it to them is its own reward in a way.

On the other hand, I still don't love document review, and I have to do some document review. And so that part of it, that will never change. But it's just the work that has to be done as part of the job.

But they trust me enough to do research and writing here, even though that's not really mostly the role of staff attorneys. I have kind of carved out a niche for myself where there are people who have gained enough trust in me to say, you know, we are kind of short-staffed and need someone to write this section of this brief. Can you give us time? And the answer is always yes, because it's more interesting work.

Katya Valasek:

I think that's so interesting when you contrast it with the work you were doing earlier on, where you said you weren't connected with your colleagues, you really didn't care about your clients, so you were taking advantage of all the perks, trying to take as much as you could from that experience. And it seems like now in your current role, where you're aligned with the client's goal and you're invested in the representation that you're doing, it sounds like you are now trying to give more, right? You want to do the research, you want to do the writing, even though that's not typically what your title would entail. Is that accurate?

Charles Star:

Yes. But it's funny because it is kind of the ideal position for me dispositionally, to the extent that someone wants to use me as a kind of brain on a shelf that can be called on to turn a good phrase and put together a good research memo and write a brief or edit someone else's work. I've been doing this for 30 years in various capacities.

If they want me to use that part of my brain, something that I was slow to realize was to my advantage. I used to think that I would want to charge a premium for that. But now, I don't know, you could call it Stockholm syndrome or whatever.

I would rather use that to buy myself out of document review. And so I jump at the opportunity to do that kind of work instead of looking at a coding panel of relevant or not relevant and that sort of thing.

Katya Valasek:

And I have to assume that the same skill that a comedian has with terms of phrase or word play or drawing connections in language as they're telling a joke is a skill that benefits you now when people are coming to you for help with drafting something in particular. Do you feel like you strengthened that ability to tell a story in a legal document while you were learning how to tell a story as a comic?

Charles Star:

I think it helps me more as an editor than as a writer in that I have, I think, a good ear for when something is convincing or coherent. And I feel like as a writer, it can be very difficult to get unstuck to do a first draft because you overthink it. But I think it has made me a very good editor in terms of being able to process.

And I mean, that's, you know, you sit in an audience as a comic and watch other comics and audiences don't do this, but comics do this. You sit there and rewrite everyone else's jokes as you're sitting there arrogantly. You're like, here's a better tag. Here's a better way you could have said it. Here's why I think your premise is flawed, right? It's all self-aggrandizing criticism of other people. And so I think in that sense, the same tools that brought me to and I developed doing comedy, I think make me, yeah, I think make me a pretty good editor.

Katya Valasek:

You said earlier that you believe in the butterfly effect and you have no regrets. You got your car, you bought an apartment, you met your wife. The trajectory of your life led to where you are now. But do you ever regret making that, as you described it, cowardly choice not to pursue a public interest career after graduation?

Charles Star:

Two levels to the question. The answer is, do I regret it in a two roads diverged in a wood way? No. I like where I ended up. Do I regret it in the sense of what it says about me or said about me as a 27-year-old? Sure. I wish I were a different person at 27 who would make a more compatible choice. But time only moves one direction. So I'm not going to spend any time beating myself up over it. What am I going to drive myself crazy? I'm in therapy for other things. I don't need to be in therapy about a choice I made 35 years ago.