Jen Kirkman on Accepting Career Opportunities and Life’s Changes

You may know Jen Kirkman as a standup comedian, as a writer and panelist on Chelsea Lately or from drinking wine and retelling historical events on Drunk History.

Her acts are personal, and don’t contain pop culture references that could date the material. Her book, I Can Barely Take Care of Myself was about her decision to not have children and the repercussions of those who oppose it. As she prepares to film her newest standup special while touring and writing a new book, she’s juggling the various facets of her job, but not always by choice. Her work ethic mantra is, “I have to or I won’t be able to”, and she doesn’t take for granted any opportunity that comes her way. This is a woman with a career mission.

I spoke with Kirkman about her problem with being called a role model and the career aspirations she still has. We discussed accepting your past self and acknowledging change while writing her next book and a mutual love of fashion.

You’re getting ready to tape a live special, how did you decide that now is the right time?

It’s been in the works for a year. I was never the kind of person that wanted to do a special because I had just done albums in the past. For example, I never wanted to do a special with Comedy Central because I don’t like the editing and stuff they’re in charge of. I never really liked the idea of doing specials because I like performing live but I hate the faces I make when I perform and didn’t want one bad outfit out there for eternity. But when a company offered to pay me to do one, I thought now is a good time. I tour for a living and more people will know about me. Then of course I will not be able to perform any of the material I do ever again, but that’s okay!

How did you decide to film it in Austin?

I chose Austin because when I was on my book tour a few years ago I did a gig at The North Door. The audience was so amazing that I couldn’t believe it. They made me feel really great, they were perfectly excited and showing their appreciation with all the great sounds an audience can make. It is more a music space than comedy club so every single person who was there knew who they were seeing. The actual performance place is so cool looking and I love that the only way to get on stage is by walking down these stairs. It has a really great vibe, the acoustics are great and the staff is amazing. They’ll make posters for you, stuff I never asked them to do but they just go above and beyond. As lame as it sounds, they have candles and flowers in the dressing room – which is something I really have not experienced at any comedy club. Then I did a podcast taping there of my podcast I Seem Fun, that has a big listenership in Austin. The taping went so well I announced on stage if I ever do a special, I am doing it here. It really is the perfect match. Even if The North Door was located in Iceland, I would have taped it there.

I’ve been to Iceland for a stopover – it is a lot of rock.

[laughs] I would like to go but maybe not to perform!

I’ve travelled alone quite a lot by my standards, how do you manage traveling alone?

Not so different as far as the airport except I have a busted rotator cuff from lifting my own suitcase, but I think that could happen to a man too. It is different because I take things a little more seriously than the average dude; I have to be constantly aware of stuff other people aren’t. I don’t walk alone at night, especially if it’s somewhere with drunk people or fans where people could get grabby. The difference is that I am never going to stay in a comedy condo. I think I might be past that level, but I have comforts I need. I’m not going to stay in a motel with a door that opens onto a parking lot. I don’t want to rough it at all. I like to stay in a hotel with a staffed lobby that hopefully no murderers come into! It is little things. Like one night after a club show a comedian asked me why I was calling a cab because the hotel was like three blocks away. I was like, “It is 1am There is never just three blocks away when you’re a woman at 1am” Most places provide transportation to make sure you get to the venue on time as comedians left to their own devices would probably show up like one minute before their set.

Who were your female comedian role models when you were coming up?

I didn’t have female comedy role models growing up because I didn’t know I wanted to be a comedian. When I was younger I saw so many comedians who were women on television. I saw more than just Joan Rivers and Roseanne, I saw Susie Essman and Judy Gold. These were women I watched on TV who were road dogs and New York comics. I liked Sam Kinison and George Carlin when I was a kid so it wasn’t female specific. I never thought about being a female until I was one in the world and people kept telling me I was. But obviously Joan Rivers is my number one and I talk about it all the time. Mainly for her work ethic and what she has been through, not just her comedy. Her story is the most inspirational thing I can carry around with me and it’s been the only thing that has given me hope throughout my entire – I don’t want to say career because I think I have a job right now and am working towards a career. When I was younger, maybe a teenager, I saw a lot of standup on TV whether it was HBO specials or The Tonight Show. I saw a lot of mid-level women on stage and it seemed totally normal to me. If you asked me when I was little, “Do you think women can be comedians?” I would say of course!

Have you been told you are a role model to other up-and-coming comedians, women in particular?

I’ve been told I am by them, but I try to tamp it down. I implore people to listen to me when I tell them I don’t know what the model is! If it is my career, they should look for Amy Schumer, Whitney Cummings or Chelsea Handler because in a year if I didn’t get a gig, I would have to take a day job temping. I am not financially set and to me that’s what freedom is. I’m still struggling in many ways, and in many ways I am not. I know it looks like I have lots of things going on and I do, but I am not necessarily in control of everything. I have big goals for myself. It gets to the point where you are travelling doing five shows a week every week and you aren’t in control of your career then. Right now I am writing a book on the plane and running to this gig and running to that gig because I have to say yes to everything. It is something I know I have to do for a couple years until I achieve the next level. I want to tell them, “Don’t think because I’m headlining a club this weekend that you want to be where I’m at” – you always want to be completely in charge of your own self. I’m still finding where I want to be as a human being and a comic. I’ve been talking to younger women who say, “I look up to you, this is amazing, you’ve made it!” If you think this is making it, you’re going to be so fucked! People need to look at it as a job until it’s your name on a late night show or you’re selling out theatres. If you don’t and you walk around thinking you’ve made it, you’re going to slip and get lazy. Maybe they look up to me because I’m outspoken about feminism, but it’s pretty easy to do they just have to do the same thing and they can be a role model too! [laughs]

You have an admirable work ethic while juggling a lot of things: touring, writing a book, and the new special.

That’s where I correct people because I see it as an opportunity for what I can do. Work ethic is what you do when you’re broke and what you do when you’re rich. I didn’t work a lot when I was broke in New York, just going out a little bit here and there. I refuse to say I have a good work ethic because if I don’t get this stuff done then my agents and managers will drop me and Simon & Schuster won’t do my book. I don’t want to be working this much, I want to do all the things I’m doing, just not at all once. My schedule is a shock. I suppose that’s a work ethic but I’d love to see what it looks like if I had 30 mil in the bank, how much work would I be doing?

You mentioned your second book, what’s the subject matter of this one?

When I was writing the first book about not wanting kids and the crazy things people say to me about not wanting kids. It had to be very on subject no matter what I talked about and very much a rallying cry for men and women who feel like outcasts and a fuck you to people who make us feel that way. My life was happening as I was writing, but I couldn’t write about that. I was going through a terrible divorce, my friendships were changing, I was dating again, I was starting to travel alone, and I started living alone after 10 years; this book is about turning 40 and all that. I’m not saying everyday is a parade of, “You go girl!” Sometimes I feel really lonely or shitty about myself and a lot of times it’s great, just like being married! One of the things I’ll focus on is how my married friends like to brag how hard it is to be married and that they’re doing the work, but if I ever said to them, “You should get divorced then,” it would be an insane thing to say. But whenever I say, “It’s really hard living on your own and being single sometimes” people tell me to meet someone and get married again. That’s not the answer either. Every choice we make has its ups and downs. Every chapter is different, funny stories whether it is about traveling or relationship mistakes I am making now that I should have made when I was 18.

Putting ideas or stories onto paper usually causes a realization, whether purposefully or subconsciously. Have you learned about yourself while putting words on the page?

Yeah it really does and sometimes it takes a while. My book has been in the works for a year and a half and the big, big chapter that’s about marriage and divorce was the first one I wrote. Now I am re-writing it completely like taking apart a car or something because my opinions have changed, and I’ve changed. Now I feel a lot more open in my vulnerability and in the stories I’ve told. There is a story about a guy I was dating and had a feeling it wasn’t going to work out. I was a little bit older than this person and knew his psychology that he wasn’t in a mature enough place for him and me to be an item. But as I was writing it, I realized I did want it. I was ready at that point for a relationship. I couldn’t believe I was ready to say something like that at loud as I wouldn’t have said that a year ago. As I’m writing I reflect and go, “I guess I think that” because, like you said, it is realized. I have learned how I feel about things now and become a little less scared to say them out loud without feeling like I would be pitied or something.

It’s great especially when going over old memories, to allow yourself to say, “I wanted this” or “I did think this way” and see how much you’ve changed and grown.

I’m in therapy too so I have to do that crap every week anyway. My therapist likes to say she is acting like my historian. One of my biggest problems is that I have the mind of a writer and I rewrite history to what I feel now. I might say, “I always knew I didn’t want this!” She will go back in her notes and remind me I did want it! The mind of a writer kind of does that, well any human probably does that.

To make the story better, or give it a better ending.

Let’s say I change my mind about having kids – which is the one thing that is not flexible in my life. Let’s just say I changed my mind about it. I would be one of those people that completely forgot I even said I didn’t. I know myself so well, I’d be like, “Oh yeah, that was just one angle I had but no I think I always…” I totally am a bullshitter about myself and my own thoughts.

Oh that first book? It was just a joke!

Yeah, but I know definitely dear God, I am knocking on wood! My parents are too old to bother anymore. They have grandchildren that are grown up so I don’t think they want any more babies.

I of course love comedy, but fashion too, and I have always enjoyed your tweets and Instagram photos about fashion. I did my undergrad in theatre like you then went to Scotland for my masters in fashion.

You did? Oh my God I am so jealous! I would love to go to school for fashion. That is the other thing too. If I could somehow start over and work in fashion as well, I’d love it just as much. I know I don’t really know a lot about it, I just know what I like to look at. God, I love it so much, I would love to go to school for it or something! How wonderful. I can’t draw for shit or anything, but I would love to know about it.

To see a comedian make jokes about fashion and clothing is refreshing, because it combines two of my favorite things. 

It might be weird but I would love to somehow mix it. I just lived in Brooklyn the last two months and there was a vintage clothing store down the street. I went in everyday and looked at all their new items and never bought anything. I love fashion so much. That is what I hate about not fully controlling my career – if I could really do something with fashion, I would love it. It is cool now I get tweets and Instagrams from people who see something I would like, even dudes are doing it. I think it’s really neat and I really love when people recognize that I like that stuff. As I’m driving to the airport right now I have all my magazines ready. I go in and mark up the pages and pull things out for inspiration. I’ll always love the ‘70s look – bell-bottoms, long scarves and hats. That will always be the best I think anyone can look.

It’s like comedy in that way, it can be hard to explain your choices when one thing makes you laugh and another doesn’t or why you prefer one type of clothing over another.

You know the one thing about loving fashion and doing a special is that you are so limited to what you can wear. No leather pants because it makes the camera do a weird thing, no red to blend into the curtains and no black or you’ll disappear. So I’m kind of looking at colors I never really wear.

Especially because you don’t want to look dated.

Exactly. I would rather just look dated from thirty years ago then dated from whatever this is right now. Honestly as long as I look thin. Oh it is so horrible to say as long as I look thin then it is fine!

But that’s always the dream! What else do you have planned for this year?

I’m planning two tours for 2015, one in support of the special and one for markets I haven’t been to before. There are a couple maybes, whether I’ll pitch another show about my life if I can stomach it or whether a pilot I filmed will get picked up. I am just waiting for a bunch of things to fall into place before I know. That and touring, touring, touring! [laughs]

Jen Kirkman is taping her latest standup special on Saturday, January 31st at 7p.m. and 9:30p.m. at The North Door in Austin, Texas. Tickets are only $10 and can be purchased through her website at

Kaitlynn E-A Smith is a writer, MA fashion grad and (mostly) creative mind. Follow her on Twitter or Instagram to read her thoughts and look at her cats.

Jen Kirkman on Accepting Career Opportunities and […]