Jen Kirkman on How Comedy and Life Get Better After 40

The last chapter of Jen Kirkman's newest book, I Know What I'm Doing and Other Lies I Tell Myself, is an homage to Joan Rivers, a comedic hero and resident mom-in-her-head. But instead of referring to Rivers as a "female comedian," as many do, she describes her as "a stand-up who also happened to be a woman."

"Female is not a type of comedy," Kirkman writes. "It also implies that females only talk about 'one thing' — being female, and that men, just regular old comedians, discuss more important, universal things. You know, like their dicks."

In her own act, Kirkman, another stand-up who also happens to be a woman, covers a great many topics — though almost none of them have to do with the male anatomy. Some, like the assumptions people make about her divorce (no, she isn't sad) or her lack of interest in motherhood, come as a result of simply being a woman. Others, like dealing with anxiety over a day-long flight to Australia, navigating a one-night-stand with a younger partner, or observing a grown man who's made it 30-odd years without knowing the difference between a lemon or a lime, are simply what happens as you get older: You get more stories.

And at 42, Kirkman has amassed quite an arsenal. Some can readily be seen on her hour-long Netflix special I'm Gonna Die Alone (And I Feel Fine), which was re-released this year as a comedy album, or through her work on Chelsea Lately and After Lately, where she was a longtime writer and made on-camera appearances. Others can be heard on her semi-weekly podcast, I Seem Fun, or on Comedy Central's Drunk History and @midnight. As a nearly 20-year comedy veteran, she's created an impressive resume with no interest in slowing down any time soon. She's also no stranger to the "women in comedy" question, nor the "women in society" comments and side-eye that come with being an outspoken personality who yes, occasionally travels alone and no, does not want children. She has, however, managed to turn them into two successful books.

Released earlier this year, I Know What I'm Doing is the follow-up to the comedian's best-selling first memoir, I Can Barely Take Care of Myself: Tales from a Happy Life Without Kids. It's a follow-up in that it's literally the next chronicles of Kirkman's life, from a decision to get a divorce to re-discovering herself as a single woman nearing 40. It's an honest, funny collection of real-life happenings with a pinch of advice thrown in, such as: Never ask a newly divorced person, "Well, why did you get married in the first place?"

This summer, Kirkman returned to the stand-up circuit ahead of a new special, slated to tape in October, and she brings her new material to Stand Up Scottsdale for five shows starting Thursday, September 1. New Times called the storytelling comic to chat about her latest book, why she no longer runs her own Twitter account, and why you should never try to live up to anyone's expectations. She may say she doesn't know what's she's doing, but that certainly hasn't stopped her from trying to figure it out.

New Times: Your first book was about your decision to be "child-free" and I Know What I'm Doing is about coming to the decision to get a divorce and creating your life afterward. I can't believe in 2016 these topics are still taboo — I mean, why is a grown woman making her own decisions, why is that still shocking to people?
Kirkman: [Laughs] That's my third book. [Laughs] The first book, that's a comedy book that I wouldn't even recommend to someone who wants a real deep read. It really is funny, funny, funny – treating it very lightly. And mainly the topic was not about my decision to not have kids — a decision implies you have to weigh both sides. It didn't even dawn on me. I've never for a second in my life thought about children. It doesn't make sense to me, for my life — and by the way my life, I mean even if I worked 9-to-5 and came home every night, I don't even mean because of the travel and being a comedian. Who I am as a person does not want to raise a child.

I started it off as a book about, "Look at what these dumb people say to me about not having kids," and the book turned into a life of its own and [became] part of this child-free movement and I'm talking about these "wonders of not having kids" and I was like, I don't even know if there's any wonders of it, I'm just saying I don't have any and people say weird things to me. In some ways it's like you said: Why is a woman making a decision something she has to keep justifying? I had to do the most serious interviews when that book came out, like I gave up a child Sophie's Choice-style, so dramatic. [Laughs] It's very strange for me. I never thought it was a big deal to make my own decisions.

"I know there are people who like me, but I want there to be a million more of them."

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Early on in I Know What I'm Doing you talk about seeing a therapist with your then-husband, and how what you really were doing was looking for permission to make this decision you'd already made: to get a divorce. You wanted someone on the outside to be like, "Yes, that's what you should do." I think maybe it's very similar to what fans are looking to with your book and comedy. Do you feel that way at all?
Oh, that's a good point. I only feel that way because some people have told me that. It's a relatively speaking small percentage of fans, I'm not saying it's every single person [laughs]. I have received direct messages or e-mails from people saying, "I just read your new book and my girlfriend and I decided to break up." Yeah, it's definitely happened. For me, writing it, my dream would be that, yes – anyone reading it who is really looking for support or a high-five even or any sense of validation that they're normal or that other people have felt this way that's my – that's not why I write a book, but if that's the take-away I think that's the best one I could get. Because I know so many times in my life where we've all wanted that.

The books is unflinchingly honest, and you share some of the same stories in your stand-up special but approach them differently. How do you decide you have enough material for a written book? Do you go in with a certain expectation?
The one story there's big crossover with is the story of a one-night stand I had six years ago with a younger man. That is a great stand-up bit, but in a book I can stretch it out so if you were to read the chapter out loud it would be like, a 20-minute story. I think some things work really well as both. Because I'm a storytelling comic it sounds okay on stage, it sounds normal, and then when you read it in the book it doesn't sound like, "Gee, was this stand-up?" If it sounds good reading it and it's pertinent to the topic, for me it's really about the theme: Does it push the story along? Does it illustrate where I was at a certain time? If it fits all those then it's great. If it's just a funny story and I can't justify putting it in a book, I'll just wait. [Laughs]

Thank you for doing that. It's always so obvious to read otherwise.
You can feel it sometimes.

You can totally feel it. But this show in Scottsdale is all new material, right?
I'm taping a comedy special in New York on October 1, so I'm just going back to the clubs where there could be people that don't know me. It's not quite like doing a little theater with all my fans. That's how you really know something's funny, is trying it out in front of people who may have just walked in to see some comedy. They don't know you and the jokes have to be solid.

It's all new stories and jokes: I talk about getting a tattoo at age 41 that's a really dumb tattoo but I love it; I talk about my newfound hypochondria, I made an ass of myself at the doctor; I talk about a road rage incident I had. It's very personal, but it doesn't have any of the same themes as my other stuff. I talk about going to Italy by myself even though I'm in a relationship – because it made more sense to go alone since I was already in Europe on business – and how people were having a heart attack about that. So some of the themes creep in, like women and society, but it's from a different angle this time. They're all deeply personal, but I don't touch on children or marriage or anything like that.

Turning 40 gives you more material, in that you have more stories, but does it change your approach to stand-up at all?
A little bit. I think getting older changes everyone as a person: You're more comfortable with who you are. It's so hard to explain because it's such a quiet, peaceful comfortability that I suppose could be "fuck it." I certainly say that when I'm describing it – but it's not the movie Bad Moms "fuck it." I don't think it sounds like permission to act like an asshole or a teenager again, I just mean it's this quiet acceptance of who I am. I've certainly done enough in my career that I know some people like it, some people don't, but it's what I do for a living. If you like it, great, if you don't, well, don't tell me and no one will know.

On stage, this is me, this is who I am. It's the same way I feel in life. It's no different except that I have to keep talking for an hour and be funny. I'm not afraid or ashamed of anything. I try to make [it] palatable with everybody. I have a joke that I do about street harassment. The whole point of that story is what I was thinking and it's a funny, weird, crazy story, and I tell it now knowing I don't know if a lot of guys understand what street harassment is, but we're not here to admonish them – and the women know, but I'm not here to only appeal to them and alienate half the room. Something comes with age where it's accepting – it's not that kind of, "Hey, I'm 20 years old, I'm gonna talk about street harassment. If you haven't experienced it, fuck you, women have." It's not that. It's like, let me explain in a funny way what the phenomenon is and why we don't like it. Everyone's comfortable? Good, now we can keep going. There is a sense of you've gotta make everyone comfortable and still do it in you own voice and speak your truth. And then if people don't like it, oh well, it doesn't really affect me that much. It's not like how I felt at 25 – fuck it, I've got 20 more years to get my shit together – it's a quiet acceptance.

Kind of like you don't need validation from anyone, whether it's a comedy reviewer or some guy who got dragged to a show by his girlfriend? You'll survive.
Exactly. Well, I hate bad reviews, but it's not because I don't feel validated, it's because I don't want it to affect my ticket sales. And I also just accept, well, I don't like everything I see, so why would anybody else? And the reverse: When people come up to me and really love things I appreciate it, but I don't take it in as, "Well, I can rest now and I'm the greatest." I keep working.

I think that's interesting because there was a short line in the book where you were talking about how you're still building your career. On one hand I totally get it, you're always going to challenge yourself to do more and push yourself creatively. But on the other, you've been doing comedy for 20 years and you have specials and best-sellers. When will your career ever be built – or should it ever be built?
For me, it will never be built. It's really a job. Every year I sell a script to a network that never gets made into a pilot and then there's the next phase, you make a pilot but it doesn't get picked up as a TV show. Then there's the next phase: You get a TV show, you're the executive producer-creator, you run a show. I haven't done that; that's a level of my career I haven't achieved yet. Is it the most important thing for me? No, but it is something I have tried and it hasn't happened. That is not a failure, it just hasn't happened yet. To be able to sell out thousand-seat theaters and make a certain amount of money, instead of going on the road 200 nights a year to go to 75, that hasn't happened yet. I have markers along the way that show me I'm in the right direction, but it does take about 20 years to get to where I am – unless you break right away.

If you aspire to have my career, you're really not looking at what that is ... I think there's a certain point where you do things and everything you do turns to gold and that begets more stuff. I live comfortably, but I don't work comfortably in the sense that if I didn't work for two years, there'd be nothing left. That's a scary proposition at my age; I have to keep working for another 20 years and then retire very modestly. There's a kind of recognition where you do really good things, everyone loves you and thinks you're funny, but that's not a career per se, that's just public perception. When you become an industry, when people are making money off of you, that's when you can say you have a career.

I know there are people who like me, but I want there to be a million more of them. [Laughs]

Are you interested in creating your own vehicle or being an executive producer? Is there another aspect of comedy that you'd like to explore?
Yeah, like for the past 10 years I've pitched three or four shows a year and it just hasn't happened. It's what I do when I'm not on the road – and when I am on the road, too. It's not my first love. I think of comedy as the thing I nurture, but the other stuff is more of a gamble. I'm really lucky that I have comedy. [But] I'm tired; I work seven days a week, 365.

In a world with social media you're also expected to be accessible all the time. Do you feel like you always have to be on? Or are things like the podcast and Twitter ways to just be Jen, and listeners and followers forget that? How do you balance that?
I'm myself a lot; I take a lot of down time. I don't do anything I don't have to do. I enjoy my podcast, I enjoy social media, but I never do it because I think I have to be on for people. I'm never thinking about the people and what they expect, because I could never live up to anyone's expectations. I just do what I do because I love it, and that's always what I've done about anything.

I'm on social media because it's a great way to advertise things, I think, but I write a thing on there because I'm moved to, or I do my podcast because I love it. If I'm not happy then I can't do anything in my life. It's not hard for me to balance; it's my number one priority.

With the Hillary tweet – I don't want to get into whether it was right or wrong because that's entirely subjective – but because of that and the disgusting and terrible responses you got, do you still think social media is that great tool?
[Laughs] I don't run my own Twitter anymore. Yeah, I still think it's a great tool because I still think it's a great world, but awful people exist in it. To me it's not the tool, it's the attitudes of anyone who is awful on the internet, whether it's about political situations they disagree with or they just want to reach out to an artist and bum them out and say, "You suck." I don't think of it as an internet flaw – well, it is in a sense that I probably wouldn't have known that without the internet. I'm very sad not to be running me own Twitter, [and] it's not like I couldn't handle anything, it's better for my mental health to not have to see stuff like that every day. I run my other accounts, but it just takes me on a rabbit hole of responding that I don't want to be in. It's not about not seeing the hateful things, because I still ask the person who runs my Twitter to tell me. It's not that I can't take it, it's that I don't want to engage it. I still have a very optimistic view of the internet, it's where I go for everything in my life.

Well, nobody should ever have to "take it." No joke should ever be met with a rape threat.

Jen Kirkman performs live this weekend at Stand Up Scottsdale, 5101 North Scottsdale Road. Showtimes are at 7:30 p.m. on Thursday, September 1, and 7:30 and 9:30 p.m. on both Friday, September 2, and Saturday, September 3. These are 21-and-over shows; two-item minimum is required. Tickets are $15 each and can be purchased through or by calling 480-882-0730.

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Janessa is a native Phoenician. She joined New Times as a contributor in 2013. You can connect with her on social media at @janessahilliard, and she promises you'll find no pictures of cats on her Instagram — but plenty of cocktails.
Contact: Janessa Hilliard