Jen Kirkman Stays True to Herself

Beyond being a standup and podcaster, Jen Kirkman is a bestselling author too. The Drunk History regular recently released her sophomore book, I Know What I’m Doing - and Other Lies I Tell Myself: Dispatches from a Life Under Construction. While the first book examined her decision not to have children, this time she opens up about divorce, sex, staying true to yourself in adversity, and how she rewrote history.

The last time we spoke was before her special, I’m Gonna Die Alone (And I Feel Fine) debuted on Netflix. I caught up with Jen on tour and discussed the new book, the style of her new material, and where she thinks her comedy is heading next.

There’s a part in the book where you talk about growing up wanting to fit in. Do you think it has something to do with your comedy or why you started?

It’s weird because the show I’m doing with the book tour is a one-woman show, and a lot of the material hasn’t been heard except for by people in LA. A lot of it’s about not wanting to fit in and thinking I’m better than the other kids. I didn’t fit in but every time I noticed I didn’t fit in, I’d be like, “The fuck is wrong with these people?” One of these stories is about not knowing David Lee Roth covered a Beach Boys song cause I only knew the original; people were horrified I listened to oldies music. At the same time I felt like I didn’t fit in, I also felt superior but was also wondering why people en masse know things I don’t know. Looking back, it’s all stupid shit cause my parents are older and my siblings were older than most siblings and I was a bit sheltered living in this weird world. My house was in the ‘80s but inside was the ‘40s, ‘50s, ‘60s, etc.

I think the flip side of that bravado is sadness wondering why everyone isn’t like me. Why aren’t we all doing the same thing, why is it bad if I’m different? There was a big period where I was obsessed with doing things right. I didn’t like any school assignment that was letting us do whatever. Weirdly, art is hard for me because it’s subjective. I think not fitting in, the two sides of it still exist today, and I know my type of comedy is never going to be the type that has mass appeal and everyone likes. That’s okay, but also why aren’t I the type everyone likes? It didn’t play into me starting comedy cause I wanted to do everything else before comedy. No kid is like, “Oh my family is always in chaos and my sisters aren’t home or are home and fighting and I need to manage everyone else’s feelings” but as a standup I think it’s funny I’m not uncomfortable in front of an audience. I’m comfortable in the uncomfortable. I had no idea there was a good job for that.

Where you don’t have to worry about every person there and why they’re laughing or why not. 

Or I could worry about it and manage it quite well like a codependent person. Now, I don’t really think about it but I’m being super analytical. What better job for a person that didn’t feel like they fit in but is doing everything they can do to make it OK? You don’t fit in, you’re standing there.

And now you’re letting everyone know about you too, you’re talking about yourself and they are fitting in with you because they are reacting and laughing at it.

Oh my God, you’re totally right, I’m finally getting that. I guess its validation. It’s so funny you said that because I think you’re right that it comes from there. I’m not looking for emotional validation and for people to love me but I am looking for, “I’ve thought this, does anyone else think this?” That’s not why I do it but I think some people think I tell jokes cause I know it is gonna be really funny, I hope it is but the motivation is, “I think we’ve all felt this.”

That’s why some people do really well connecting with others in different areas away from standup. I think there’s this interesting part of that personality, people find their creative outlet through their own vulnerability. You’re not doing a dramatic reading, it’s generally making people laugh and opening up about what isn’t perfect.

I wish I was doing a dramatic reading; that actually sounds easier in a weird way. The show I’m doing now, I can’t do it in a comedy club – it doesn’t follow the same format as standup. I like telling stories that can not have a punchline for a couple seconds.

I think a lot of people workshop their books that way too, reading short stories or essays in front of an audience to see which parts work. 

Oh that’s interesting. I just found out recently that David Sedaris does that kind of thing. Reading in front of crowds workshopping that stuff, it never dawned on me.

And when a writer has that skill to read on stage, it’s like two different worlds combined. 

That’s how I feel writing. I don’t care if it makes a room laugh or one person in Kentucky laugh or someone in Utah cry and others don’t care. I figured writing a book is so different that thank goodness it isn’t about what roomfuls of people think at a time. Maybe I have too much confidence. Not confidence – maybe I just don’t care enough.

Also it’s not a live show. You have to be totally done with reworking and editing.

That’s the worst part of it, too.

Are you one of those people who could edit forever, or was it a relief to finish?

It was a relief. There were so many rounds of editing and at a certain point towards the end I wanted to take out entire couple paragraphs, but they were like “You’re gonna fuck up the layout” so I could only do a word here or there. When I reread it for the audiobook, it was small things like “I don’t like those two pages” or “Why I didn’t go into my true feelings instead of making a joke?” Thank God it’s not the whole thing I hate. I felt like I’d like to do more books and more everything and make it perfect, but if I’m obsessing over a page, no one is going to notice while reading it. It takes so little for people to feel like you’re being open that they’re not gonna see if I’m not totally open in every part. If I end a serious thing with a joke, I don’t think people will assume I’m hiding something. People are always like “Wow, I can’t believe she said all that!” and I’m feeling like I didn’t say enough. I had that in my head but I wasn’t trying to obsess over it.

The fact that you’re standing up in front of everyone, people are already thinking you’re doing more than they could, so everything that comes after is extra exposition.

I can use it to console myself but I can’t go into it thinking, “They’ll love this!” These assholes don’t get up in front of crowds.

Is the show you’re doing now based off the book?

No. Back in LA in 2004-2006 the Aspen Comedy Festival was a big deal and you could audition in two categories, standup and one-person show, and every year I did both hoping something would get in. I used to do all these storytelling shows with all this material I’ve never done anything with. Some of them became stories in books, but there’s this whole story that relates to a lot of things. This show is nothing from the book but the theme is that I know what I’m doing.

I have a story about ruining a talent show when I was little, beating up a boy with a hockey stick and having to go to anger management, being afraid of the movie The Day After, the Prince song “1999” changing my mind about the world ending and being in New York on 9/11 but I was hungover and told my best friend I was in love with him even though I was with someone else. Stuff like that, I might exaggerate a bit or fuck with the timelines, but it is all real things that happened. It’s the more disaster-y moments in my life and each story ends with someone telling me to go to therapy and I didn’t mean for it to end that way. The last story is about finally going to therapy and everything being okay now. I really like it but it’s a long-ass show and it’s just me and I’m wearing a headset. I do some dancing and moving around, I just feel like if you see someone’s hands free it’s not necessarily a standup show. I think this is actually funnier than a lot of my standup. I figured I’d tour with something that’s more storytelling than standup. I’ve been kinda working on it for the past six to eight months.

I think I relate to storytelling shows because I knew theatre before I knew standup. It’s kind of weird that I can relate more to performance art than to sitcoms.

That’s how I was too, I always gravitated towards that. I didn’t like comedy until the last hour. I went to poetry open mics in New York, I thought I’d be a poet or a dancer, and if I go to watch TV it’s never a comedy. People talk about growing up with comedy albums but I didn’t know I loved comedy, I loved everything. It wasn’t until a lot later that I realized it was a thing. I was totally a snob. I was in an improv group in college and we were trying to be like UCB longform, and Del Close was teaching a workshop in New York and anyone could go, so they drove there to take a class with him. But I stayed behind doing some play where I played some young girl in love with her professor. I was like, “I wanna do this play in this little black box theatre and it’s just me and this person talking for an hour. I’m not getting in a van with a bunch of comics driving from Boston to go see Del Close…I’ll do that another time.” They said it was amazing but he was just yelling at them the whole time. It meant a lot more to me to do the play at the time. There’s a lot more time for comedy than there is to do that theatre stuff when you’re older. Yeah, I’ll have to find that play and reread it, there’s no way it wasn’t terrible.

What did you learn about the writing process from your experience with the first book?

Well, I had the same editor both times so I think with every editor it may be different. She taught me to do this, which is embarrassing that it wasn’t obvious to me: “Leave every chapter with suspense so you wanna turn the page.” I was being too literal wanting every essay to end on its own and be its own piece. She taught me I was writing a book and not an essay and now I see it, even if it’s the littlest thing that hints at what’s next. I think she wanted the first book to be more joke-heavy. I think when you’re a first-time author and you’re funny, just be fucking funny, don’t try to rewrite great works of art. This time I was like “Okay, as much as I want to write heart-wrenching things, add the jokes in, and end on a joke at least every paragraph…” I had that stuff in mind and that was just her voice in my head.

Other things I learned from reading other people’s books. I like when people write matter of factly. It’s easy to get caught up in longer sentences, bigger words and using a thesaurus, but then it doesn’t seem organic to me. You hear in your head that if you told someone this story you would have to keep sidebarring, which doesn’t work out well in real life so don’t do it in a book. There was a whole chapter about going to a casino with my family and knowing my marriage was over but I didn’t add this important part: my husband’s mother was also on the trip with us. It was very weird, but nothing happened, she was just there. It was such an overwhelming emotion in the story that I didn’t need to add her, just drop it. At least I had the ability to look back and go, “Oh this is babbling and we don’t need it.” I did not have that in the first book. [laughs]

That’s an important skill, to speak matter of factly. You’re reading this book I wrote, you might as well hear me straight to the point. Hearing stories in person you think you need all the details.

I don’t know if I did it, but I tried. But you would hate if someone was like, “I have the best gossip!” but gave a weird truncated version. In my standup I tell the stories naturally – they don’t need to know all the details. The important thing is how I felt about it. If it’s exaggerated a little or that timeline doesn’t exactly add up, who cares? They get the point. You can do that with a book but you feel like you’re lying – like Oprah is going to come, James Frey-style, and ask why you didn’t include that, why didn’t you say his mother was there!

Oh! I also learned that the chapter you’re dying to write and start with is always the shittiest one you’ll finish last. That happened in my second book too. The point of this whole book is this story! I wrote this long, 60-page chapter and thought “Ugh, put it aside and go back to it later,” and it turned into three chapters with a lot less boring details.

In the second book, does sharing more about yourself make you feel more vulnerable or affect your comedy, or are there still secretive things you don’t go near?

Oh I totally do! That’s what I’m thinking about getting into next maybe, but I have to go through some things first. No, there is a ton. I’m inching towards a few things, like in this show one of the bits will be in my next special. It’s about lying about when I lost my virginity, which is ironic because it was the first joke I ever did onstage, about being a virgin when I graduated high school and why I felt bad about it. There’s a whole other lie I’ve told to so many people in my life about who I lost it with, when it was, and how much sex I was having. I didn’t have any until I was 21 and no one knows this. Literally no one in my life knows. All my college friends thought one thing, the person I lost my virginity to didn’t know, and so I made it this whole story now that I am in love with. It goes back to why I was so afraid: afraid of getting pregnant, not knowing how the body works, thinking you could get pregnant from fingering, it goes in these crazy directions. Going into college and lying about how I slept with all these people, thinking that would make me more attractive to sleep with…and it backfired. I don’t know if it’s just the nineties, but everyone was a virgin in college. When I told them I was lying, no one believed me. The point was that I didn’t know if you could be who you were and feel accepted.

It’s weirdly stuff like that that makes me so uncomfortable. I have a hard time admitting when I’ve lied, so talking about stuff like that is a bit easier now. I don’t know if it’s the book or getting older and now I’m just like “Fuck it.” Sometimes it just snowballs where you have to be more and more honest. I have such a small audience too so I feel like the way to build them is to stick with what I’m doing and keep blowing it up. If I get less revealing then who cares.

Not only are you telling stories about you, but it’s stories you’ve hidden from yourself or rewritten history or covered up.

Yeah, yeah you’re right. I think a bunch of my new stuff next year will be exactly that. All these years of such terrible relationship stuff cause I was telling myself I loved being out there but I was miserable and hiding so many things from people and acting like a crazy person. It hadn’t been explored on stage until now and I think I can make it relatable – these things you know you shouldn’t do or aren’t healthy but you tell yourself you only live once, life’s short, who cares. That’s where I wanna go next in my standup. I just need to make it funny.

There’s a whole array of things people lie to themselves about and instead of trusting their gut feeling.

There was this woman I worked with at this internet company in the nineties in New York. She told me this sad story of how she wanted her boyfriend to propose and she fucked it up. When she finally got the ring and came into the office I knew the real story. They went on a cruise and she thought he was gonna propose and he didn’t, so she made him go ring shopping right away and they did. She came into work, “So, we’re in Central Park and he gets down on one knee…” everyone applauds, but oh no, she was lying. It wasn’t the type of gossip I wanted to make fun of her for, it was just…let her have it, and eventually she’ll believe it. I have so much shit like that, now I’m finally thinking it’s so far behind me and I don’t care anymore; it’s funny.

If it comes from maturity or a big life event you can look back and realize.

Once you have a good sense of self…

You aren’t afraid of others judging you by your actions.

With a lot of therapy I’ve gotten there and thought “Oh that’s a lie, that was fake, I was lying to myself… that’ll be my next material.”

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

Jen Kirkman Stays True to Herself