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  • Journeys

Want to Be a Lawyer? Now That’s Funny

By Talia Reese
talia reese

From Paul Weiss to Standup Comedy

So, I didn’t always want to be a lawyer, but I was graduating from Penn, didn’t have a set plan, and was going to be getting engaged to a guy who was going to be going to law school. So I kind of figured I’d go too. We’d open a law practice together. That became our plan. I went to Cardozo law school and loved it, but I didn’t love the marriage. We divorced during my last year and I had to scramble to get a job. Clearly, our law firm idea wasn’t going to happen.

I lucked out. My grades were good so although there weren’t a lot of options out there, a judge in Chicago needed a clerk. He was nearing retirement and the clerkship with him was open because it was for only eight months. The chief judge told that judge to hire me. The chief had a degree in music and I did too. He’d never seen a candidate with a music degree, and he thought I’d be great. I met that other judge and we clicked immediately. He hired me and I moved to Chicago.

From Clerkship to BigLaw to Mommy to What the Heck Next

Knowing the clerkship was a short-term gig, I applied for other jobs to start after it ended. I was surprised when some big law firms courted me. Paul Weiss called and that’s where I started. I loved the people, being at the firm, and certain aspects of it all. But I left Paul Weiss after two years so I could take a break from law, travel to Israel and get married (again). I was too junior to take a sabbatical, so I just quit. It was an exciting time. I did all those things I wanted to do. A few months later, I started at Cadwalader. I think that was the first time I had an actual panic attack. I was like, “How am I still a lawyer?!” I stayed a couple of years and again, loved certain aspects of it, especially having found my stride as a mid-level associate. Then I got pregnant, and eventually made the decision to make my leave permanent.

But Before All That . . . Let’s Rewind

Before going forward, I’ll take you back so you see where I was coming from. I was always that funny kid. I was voted funniest in high school, played funny parts in plays in college, wrote scripts and comedy sketches, did characters, and loved it all. I was also a music major, so that went hand in hand with the comedy. I wrote the music for the plays, all original musical numbers. I was the musical director of the group, “Bloomers” at Penn. Then, right out of Penn, I got a job at NBC as a page because I knew I wanted to be on “Saturday Night Live.” I even had “Saturday Night Live” interested in hiring me to write. But TV wasn’t a career for a Jewish girl from Great Neck. My parents weren’t on board and I was living at home. You get the picture. So, I made a deal with my parents. I’d take the LSATs and go to law school if I could go in New York City and do it debt free. The stock market was up and my parents agreed. So the plan to marry, go to law school, and open that practice became a viable plan.

Now back to where I was

It’s post-divorce from husband one. I’m married a second time with a happy life and kids in the mix just 18 months apart. I did some thinking. I didn’t want to spend my life at law. I’d gone from legal boot camp to baby boot camp to I need something else. It wasn’t in my mind yet to get into stand-up comedy. During my maternity leave, although I didn’t know what I wanted to do, I did know that I wanted to do something creative. Novel writing was my first foray into the creative world after leaving law. I got an agent and got published but made very little money for a heck of a lot of work. So that wasn’t for me. Oh, it’s important to know, I did warn my husband before we married that I wouldn’t want to do law forever – that I’d want to do something creative at some point, so a career change wasn’t a total surprise to him.

What to Do With My Life?

One night while up in the Catskills at my parents’ place, my mother suggested I go out with my husband to see a comedian at the clubhouse. She and my dad would watch the kids. So we went. The comedian, a woman, was killing it. She was very funny. My mom’s friend had booked her. I asked that friend how much the comedian was getting paid for the night. She said $2,000. I was like wow I found my next career!

Now I knew what I wanted to do. I wanted to be a comedian. That killing it comedian offered a course in New York City. I took it but it was a waste of time with 40 different people with different goals in mind. But the one valuable thing that I got from that class was a list of all the open mics in the area. Night after night, I performed. I went to as many open mic nights a week as I could. I networked with other comics. We were all trying to break in. I’d tuck the kids in at night and then head out to do these open mics.

One night, a guy from Long Island was in the audience. He owned a restaurant and he asked if I ever come to Long Island. “Do I come to Long? I live on Long Island!” I told him. He hired me to perform in his restaurant out in Wantagh. The night I performed in his restaurant everyone who was anyone in the Long Island comedy scene was there. That night I picked up an agent. Thereafter, I did every firehouse on Long Island. Firehouses are the best, big crowds, big fundraisers. I did shows for vets, shows in restaurants. Then I got into Governor’s. I was all over the place. I auditioned at The Comic Strip Live in New York City and got booked there. Then I got booked at another club in the city. From there, things started happening pretty quickly and I was developing a solid act.

From Restaurants to the Jewish Circuit and Beyond

One day the men’s club president of my synagogue calls to ask if I’d perform at the shul. He saw my name on a list of recommended comedians and said, “That’s a member of our shul!” He called my father and asked if I’d perform. My dad told him no. My act was more risqué then and I wasn’t yet telling people I was doing comedy. Anyway, after my dad told him no, the guy thought, she’s an adult. I should ask her directly. He called. I told him I’d think about it. I got off the phone with him and just wrote a ton of stuff about my life as a modern orthodox Jewish woman. I did the shul performance and word got around after that. I started doing the Jewish circuit, Jewish organizations, and synagogues.

Then a big thing happened. Somebody introduced me to a writer at The New York Post and that writer did a story on me. She thought it was interesting that an Orthodox Jewish mom would come into Greenwich Village at night, work in these dingy clubs and bars, and do an act about her life and all.

During COVID, I was busy with tons of Zoom gigs. It was incredible. I started a website and I put a lot of clips on social media, on my TikTok and Instagram, and people found me and asked me to perform. An organization found me on TikTok and flew me to Detroit to perform. I travel a lot now, to Toronto, Florida, California. My work has really taken off.

Doing comedy nights is different now that my kids are young teens. I used to tuck them in at night and go out to do gigs. Now they’re awake when I get home! But they’ll grow up and leave for college. And, when they do, I’ll probably do a lot more traveling around—shows all over.

What I Wish I Knew Before Heading Out to Do Comedy

Nothing. Not knowing meant I wasn’t held back by fears of failure. I think it’s better not to know anything. That goes for a law career as well as one in comedy. Lawyers are always ambitious and all ambitious people always have a plan mapped out for their life. Law wasn’t sustainable for me in the long term because it wasn’t my dream. I was a good writer. I worked for top writers and top law firms. Novel writing wasn’t for me but what I learned was two things—first, hey it’s cool that I can write a book. Second, I learned I wasn’t going to waste my time again on a career that wasn’t true to myself. I was going to find what I love and that’s what I’d do. Then I saw that comedian and it just clicked for me. I found what I wanted to do and then made it happen.

Law Lessons, Life Lessons

The biggest lessons I learned working in Biglaw as pertaining to comedy are the importance of transparency and economy of words when drafting papers. That became my thing. And it’s my thing when it comes to joke writing too. I try to get to my punch lines as soon as I can and not drag out a story or a premise.

Another lesson I learned is that you need to set aside your expectations for yourself. You have to get comfortable with the idea that you may not reach a particular goal, or any of your goals, this year. You may reach it in two years or it may not happen at all. But I’m in love with the process. It’s not just about the end result. You have to adjust your mind because we’re all anxious, we’re all overachievers coming out of law. I had to change my mindset and accept that I might be about to hit 30 or 40 or even older without getting a call from “The Tonight Show” but I may be at the Borgata, and then next year I may be selling out a 200-seater in New York City.

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