Jessi Klein Wants You to Know It’s Gonna Be Okay

After years of working on beloved TV comedies like Strangers with Candy, Saturday Night Live, and Kroll Show, Jessi Klein took an opportunity to serve as head writer on a new series back in 2013 called Inside Amy Schumer, and, well…the rest is history. But how Klein found her confidence, worked for those opportunities, and earned that success – and the personal and professional lessons she’s learned along the way – is a complicated story that starts much earlier than an internship or entry-level job. It starts with an awkward teenage tomboy struggling with confidence, femininity, and an itch for a life in comedy, and thankfully Klein’s chronicled the whole tale (so far, at least) in her new book You’ll Grow Out of It, which hit bookstores last week. Ahead of the book’s release, I spoke with Klein about her writing process, what advice she’d give to her younger self, the differences between poodles and wolves, and more.

First of all, congrats on the book!

Thank you!

I learned that we have a lot in common. We both have middle child syndrome, we both don’t have our ears pierced, and your book also taught me I’m a wolf. So thanks for that.

Ahhh…I mean, what a relief to know which one you are!

Do you think women who are poodles would want to own up to that, though? To me, it just seems more fun to be a wolf.

[laughs] Wow, interesting. I don’t know that it’s more fun to be a wolf. I feel like I’ve definitely had poodle envy, I’m a fan of a poodle. What’s the fun part of being a wolf? I guess just that there’s less pressure, maybe. But to me, part of what I think of as the definition of a poodle is just that everything feels kind of effortless, you know what I mean? It is literally waking up #flawless = poodle, so I think that in itself is not so horrible. I think poodles should be proud to be poodles, and wolves should be proud to be wolves.

That’s fair.

Yeah. And I think we can probably learn things from one another.

[laughs] I hope this is the beginning of poodles and wolves finally coming together for this important discussion.

It’s a very, very, very important dichotomy.

You started writing this back in 2014. What made you decide that was the right time to write a book like this one?

Well, the main thing was that I was totally unemployed and very nervous about what I was going to do. We had just finished shooting the first season of Inside Amy Schumer, and it hadn’t aired yet, so we had no idea if it was going to get picked up again or what would happen to it. I knew the show had been great to make, I just am always a pessimist. So I didn’t have anything going on, and my manager ended up introducing me to this new incredible book agent. He read a couple of my essays and we sat down and he was like “I think you should write a book” and I was like “Really? I beg to differ.” [laughs] He kind of pushed me on it, and he set up a structure where, in terms of creating a book proposal, he was like, “Write one essay a week and send it to me and I will tell you when to stop.” And that’s how the book was born.

Where you begin with something like that? Was there one story that sort of kick-started you into the rest?

This agent, David Kuhn, was like “Make a list of stories you think you have to tell. Make a list of around 12 stories, send me the list, and then I’ll tell you which 10 to get started on.” And I did that, and once that happened I just started to feel this theme emerge – this idea of being kind of an outsider to my own femininity, which felt weird because I am a female. Once I started seeing different episodes of my life through that lens, certain stories kind of popped to the fore.

Were certain areas of your life harder to flesh out that way?

Some of the stuff in terms of writing about my ex-boyfriends and stuff like that…I guess writing about the moments that were more painful, as I wrote them I kind of went back into them and relived them. So as I was writing about an unpleasant moment I felt the unpleasantness anew, particularly with things I hadn’t felt in a long time. Those were sticky moments, so when it got sticky I would often feel like it was probably good that I felt this way, because you kind of have to be in it to write it.

Given that approach, did anything surprise you along the way? Did you learn something about yourself just by writing it out?

I don’t think I can encapsulate one particular nugget over another so much as I just think the first part in the process of writing is procrastination, and you stare at a blank screen and it super sucks for a long time, and then once you can pull yourself into the mode where you’re typing, every word is kind of a moment of self-realization in a certain way, if that doesn’t sound too fucking horribly pretentious. You’re just aware of your thoughts and yourself as you go. But I don’t think I have any Put It On A Mug tidbits.

What helped you stay focused while writing?

The very granular answer is that I’m very picky about where I write and I will blame a writer’s block on where I’m sitting. This is very weird and very specific, but at the time, I was living in Brooklyn and I started going to this one cafe near my house that checked every box of what I wanted from a cafe: it wasn’t too loud, there was a lot of space, and they had very good cookies, cake, and also booze, and a nice view and a bathroom. And you would be amazed at how few cafes check all of those boxes. If anybody else wants to write a book at this cafe, it’s called One Girl Cookies, and it is down in Dumbo, Brooklyn. I found it really nice to write a large part of my book there.

In terms of you reliving more embarrassing memories, I loved that whole element in the book of, like, ‘I’m about to tell you something really stupid I did or thought, and I realize now it was stupid, but I’m going to tell you the story while staying true to who I was at the time.’

And I’m still doing very stupid things literally every day. [laughs] It’s so much easier to just cop to it than try to pretend it’s not happening. Everyone knows.

There’s a great part in the book where you reflect on writing for other people and struggling with this sense of contributing to someone else’s success more so than your own success. As someone who’s been a writer on so many shows, what’s your evolution with that been like?

Well I think this book sort of represents a big milestone in that evolution, because it’s the first time where it’s something that’s just relentlessly, exhaustively my own voice. It’s been both exciting and terrifying. It’s kind of like the difference between baseball and tennis, or any team sport and then the one where you are the only one on the field playing – it’s kind of all on you. It’s a mixture of being really thrilling and really quite scary.

You talk about being in your 20s and 30s and wanting to try standup but feeling too insecure – feeling like you weren’t good enough. Is that feeling all behind you, or do you still struggle with that?

Oh yeah, of course. For sure. I feel like I’m never gonna be good enough all the time. I think the only difference between now and then is I am more aware that that feeling will never go away and that there is no end for anyone. When you have that view of it, suddenly, ironically, or counterintuitively, it starts to evaporate a little bit, like “Oh, there is no point at which anyone feels completely content, and so maybe I should stop worrying about it.”

On top of just being a funny book about your life, I think this it doubles as a solid advice book.

Oh, cool! Thanks, that makes me happy!

If you could go back ten years and tell yourself anything – or for that matter, advise any woman who wants to get into comedy but isn’t sure she’s good enough – what would you say?

The two biggest things I didn’t know that I wish I had known: I wish I had been more open to taking risks earlier, and I also think I just couldn’t hear enough of the words “It’s gonna be okay.” A lot of people say that, but when you’re younger, you’re going through a lot of things for the first time, and they go deep, you know? Emotions are really intense. The first time you get your heart broken or the first time things don’t work out, you don’t have the life experience to know that it’ll come around and it’s gonna be all right. I’m a big believer in saying to people “It’s gonna be okay.” And, in fact “It’s okay right now,” to be really cliché and Buddhist about it.

You’ll Grow Out of It is now available on Amazon.

Jessi Klein Wants You to Know It’s Gonna Be Okay