Careers rarely go according to plan. In Job Hacks, we shake down experts for the insights they cultivated on their way to the top of their field.

Name: Wayne Federman

Original Hometown: Silver Spring, Maryland

Job: Standup comedian, comedy writer, actor, and creator of the Wayne Federman International Film Festival. He was the head monologue writer on Late Night With Jimmy Fallon and has appeared in Curb Your Enthusiasm, The 40-Year-Old Virgin, and The X-Files, among others.

How did you get into comedy?

Here’s the thing — at the core of Wayne Federman, I’m a huge comedy nerd. To this day, I love watching standup. I get a kick watching all levels of it, from Bill Burr and Sarah Silverman to open mic-ers. I like the whole world of it. When I started out, I made sure I watched the old-time comedians: Milton Berle, George Burns … Carson, Steve Martin. I think being a stand-up comedian is the greatest job in the country, maybe on the planet. A stand-up comedian works an hour a night, gets to be the center of attention, and brings laughter — one of the purest human responses you can have. And you get to travel. It really fits my personality.

What do you do when you’re performing stand-up and something isn’t working — the audience isn’t responding?

It all depends on my feelings that day, my emotional disposition. Sometimes I’ll bail and go to stuff that’s more surefire, and most of the time I can hide the new wobbly bits I’m working on within other safe stuff. But when you write something new that clicks, it’s beyond thrilling.

Since you’ve done everything from standup to writing to acting, which area do you find the most fulfilling?

I find different areas fulfilling in different ways. Creatively, I would say stand-up is easily above everything else. You get to do it all — write it, perform it, you’re the director, you get the whole scope. In movies, I do what I call the “Federman and out.” I’m in just one scene, I do something funny, and then you never see me again. I love that as well, because I’m also a huge film buff.

Is being a film buff why you decided to start your film festival? What goes on at the festival?

For the first four years, the Wayne Federman International Film Festival was in L.A., but I’m coming to New York with that festival in November. I have comedians select films they love and we screen them and talk about them. Sarah Silverman did Crimes and Misdemeanors; Aziz Ansari did Back to the Future; Margaret Cho picked Darling. It makes for a fun evening. You get to both learn about the comedian and see a great film. There is only one rule when it comes to selecting the films — the comedian can’t be in the movie.

How did you get the idea for it?

What happened was — and this is just a small part of the Wayne Federman career — I saw Patton Oswalt present a movie I had never heard of, The Foot Fist Way, Danny McBride’s movie. I was not only interested in seeing the movie, but as I listened to Patton go on and on about it, it made the experience even more complete. I thought, that might be a fun weekend; a revival festival with older movies. In New York this year, it’ll be Janeane Garofalo on the 14th [of November] presenting The Hot Rock and Larry Wilmore on the 15th showing The Parallax View.

Since you’re more of a character actor — like you said, your method is to be in a scene and then you’re out — is it hard to jump into something, get acclimated to it, and then leave? Are there certain personality traits you need to succeed as a character actor?

I feel like you need to be adaptable. I love doing it. I can get the tone of the show by watching one episode. Curb Your Enthusiasm and Larry Sanders are two of my favorite things I’ve done on television. On Curb I got to write every line I said. That was extremely liberating. Everything I said to [Larry David], I wrote.

And how did your relationship with Judd Apatow come about — you’ve been in quite a few of his movies: The 40-Year-Old Virgin, Knocked Up, Funny People.

He was a college freshman at USC and I was visiting L.A. at the time. We struck up a friendship and have remained friends all the way through. It was very fortuitous — he was actually the first guy I met in L.A. — what are the chances? It’s crazy. I had no idea he was going to be a movie mogul when I met that kid! Thank God I was nice to him.

Using music in your standup seems like a somewhat unusual choice, what was behind that decision?

I’ve always been attracted to comedians who incorporate music. I believe there’s also an inherent musical element to stand-up comedy when it comes to timing. Music and standup are like brother-sister, I think. There was a guy named Victor Borge who played the piano in his act. He was quite inspirational. There were also some comedians in New York when I started — for example a guy named Kelley Rogers who played the guitar. I thought of incorporating ukulele into my act and then eventually I moved to the piano.

And how did the gig as Jimmy Fallon’s head monologue writer on Late Night come about?

We went out on tour and I helped him put together a new hour of stand-up. Jimmy was the opening act. He’s a ridiculously gifted comedian who has a large number of comedic skills, and after just a couple of months I said, “You should probably be closing these shows.” When he got the gig on Late Night, he wanted someone he trusted with his sensibility, so I did that for a year. I just found out a few days ago that I’ll be back on the Tonight Show on November 4th. I cannot wait; studio 6B is one of my favorite stages in the country. It’s a very historic room that I love being part of.

What was it like to be the head monologue writer? Did that take getting used to — did you need to approach it in a different way than regular stand-up?

It was a little different because late-night monologue jokes tend to be topical, and I don’t do that much topical material. But I do know when a joke has a good turn to it. We had a whole team of great writers — Anthony Jeselnik, Jon Rineman, Jeremy Bronson, Morgan Murphy. I wrote jokes for Jimmy, but primarily my job was to take those Jeselnik or Murphy jokes and put them in Jimmy’s voice, because I knew it so well.

What’s next for you, besides the film festival in November?

The Chronicles of Federman was just released — which is my debut comedy album in the form of a three-decade retrospective. It has archive recordings of me going all the way back to the ‘80s. So it’s not just my history but a look at the history of standup over the last 30 years as well. I go from clubs, to TV, to alternative rooms, and even theaters. It spans 1984 to 2015. It’s just a creative way of putting my stuff out there.