All We Can Do is Thrash
A chat with Emily Flake
My long-time friend Emily Flake, New Yorker cartoonist, author of several books, and founder of St. Nell’s Humor Writing Residency in Williamsport, PA, has a cool new project out on October 31. It’s called Joke in a Box: How to Write and Draw Jokes and it is a very funny and smart inspiration deck. Even if you have no interest in making cartoons, it is chock full of great illustrations and ideas and writing prompts that I found really helpful from a storytelling and humor-writing perspective. Also, do we think it makes a good gift? Yes, we do.
Emily and I have known each other since we were just starting out in New York; she did the illustrations for my very first book, Instant Love. She is a cool human being, beyond talented, and I am a big fan of hers. I texted her to talk about Joke in a Box and we ended up chatting about matters of creativity and community and annoying things men say to us that make us try even harder than before.
Before we get started on the chat, here is a cartoon she did in honor of all of us.
If you’re interested in buying a print (I know I am), check out Emily’s shop here.
And now onto the chat:
Emily, I was thinking this weekend about when we first met, which I believe was a Super Bowl Party at Whitney Pastorek’s apartment in Queens in like 2005, does that sound right?
I think that’s exactly it, Jami! That would have been right after I moved.
I remember standing in the kitchen talking to you, and we were drinking, and you were being funny. I probably still smoked then, too.
You absolutely did.
What fun that was. Not knowing any better, I mean. Anyway, when you moved to NYC, did you think: “Oh I’m all in on being an artist, that’s why I’m here, this is what I’m doing.”
Sort of? I felt desperate, I felt like if I stayed in Chicago it would never happen for me, and I had to make a last-ditch attempt to put myself in a place where I could be closer to where the action happens—I knew nobody was gonna come find me because I’m not such hot shit. I felt like I kind of jumped off a cliff. And before I moved my father told me that he didn’t see the kind of fire in me that he thought I’d need to be any kind of success. So part of it was trying to see if that was true?
Just by moving you had already proved him wrong.
I have three things people (men) have said to me that are bruises that I poke constantly. The other two are: an illustrator I love and respect said, “You are quite limited, but you’re a pretty girl and you have a good personality, so you’ll be all right.” And the other one is that a cartoonist named Kaz called me a hack on FB.
I have one main bruise from a man which is when a famous writer told me I shouldn’t bother trying to be a writer a few days before I graduated from college. I really think the shitty things men say to us are like their own motivational book.
So what was an early success moment where you were like wait, maybe this is actually gonna work out?
I started getting more work immediately. Maybe because of my awesome personality or my pretty face? I dunno, but either way being in New York made a huge difference; I also started doing stage things like John Hodgman’s Little Grey Books series that I thought would get me more illustration work. It took me a long long time to realize that what they really did was start my connection to the comedy world, which in turn took me a very long time to realize that that was something I loved separate from illustration
So I started putting away my day job salary and only living off freelance work - I did that for like 6 months and then I quit the day job with a bit of money saved up. But I also feel like I kind of choked and flailed my way through life at least through my thirties and arguably until now.
I identify with so much of this! I think we were all just saving up money from jobs we didn’t like so we could have stretches of time to make our art. It took me until my early 40s until I could just be the writer version of me full time.
When my dad said what he said it was after I told him I was scared to move to New York because I had a job I liked well enough in Chicago and friends that I loved, etc, and I was scared at the idea of giving those things up—basically he meant that if I wasn’t afraid to burn those things maybe I just didn’t have it in me.
You really just created all the same things for yourself in New York in the end. The job you like, the friends (and family) you love.
Sometime after the smoking book came out I had a pretty clutch setup. My husband was still going into an office every day so I had the apartment to myself, and my agent at the time was like OK, write another book. And Jami, I spent most of each day just panicking and yelling at myself. I think probably 85% of my work time is still panicking and yelling. It kills me to think of how much time I’ve wasted and continue to waste, between the self-excoriation activities and, you know, the internet.
OK, but my friend, you know it is all part of the PROCESS.
The fucking process, right.
You are interested in the process. You have made this joke in a box deck. You teach people. You created St. Nell’s, and now this comedy festival too.
I spend a lot of time wondering if I should get a therapist or just pay a psychic and then doing neither because both are insanely expensive.
I love my therapist, it is worth the expense.
With both the deck and St. Nell’s I really just wanted to make things I would like to have. I love writing-help books even if they just get me over the self-loathing hump for the day. And I could not be happier with Nell’s - it is truly working as hoped and intended, the only shadow (and it’s a me shadow, not a Nell’s shadow) is that sometimes I wonder if I’m making a space for people to do the thing because I cannot do the thing myself. Like I’m a dirtbag Ottoline Morrell.
Hi, you’re my therapist now.
Ha! OK I have thoughts on this topic too, in relationship to my work. Because of the newsletter and my great surprise about the community that has come out of it, not unlike yours. (Although mine is virtual and yours is irl.) Which is simply that sometimes our jobs change or evolve.
But also you absolutely do the thing.
Well so do you! You are doing it. I am holding the thing that you did in my hand right now. And you continue to do it.
My theory is that there is a creative spectrum for everyone and on one end it’s like, write a newsletter! Or give a talk on creativity! Or send a little funny tweet. And on the other end it’s write a book! And all of it feeds into each other. And also all of it is one giant conversation with the world, some of it in person with people and some of it on the page or in print in a magazine or online or whatever the medium is going to be.
I can totally see that, I like that. Still think I should change my IG bio to “dirtbag Ottoline Morrell” though.
She was a lady. As in Lady Ottoline Morrell. But you are no lady and neither am I.
I’m the protestant whore!
OK just a few more questions and then I’ll let you go for the day. I love the specificity and the how-to-ness of your deck. What do you hope people take away from the deck?
I thought that having something that people could literally play with would be helpful if they, like me, struggle with getting over the fear and loathing hump. A book is wonderful, and I love a book, but in a way it’s similar to how I use loose paper on a clipboard instead of a sketchbook. I think there’s something about it not being bound that is freeing.
The advice in it is the advice I would tell myself if I liked myself more (and really is probably just a synthesis of the writing advice in any book, which all boils down to similar principles anyway.) It’s all very similar to the language in my lectures - which are, again, much more about cheerleading and making people feel encouraged and less alone in this fight.
We have the same mission, Emily Flake. Even if our approach is different because we have different mediums. And also maybe where we live impacts our methods. Like I feel fairly certain I never would have started 1000 Words if I hadn’t left NYC.
Interesting! How so?
Leaving NYC and the community of writers there pushed me to connect more widely with people online, for starters. When you leave NYC—which can be really insular in its way—you’re like, Oh there’s a whole fucking world out there of people making their art quietly or in a specific space. And 1000 Words is really about reaching people everywhere.
Absolutely. I think about this all the time w/r/t Williamsport. Where there are also very talented people working.
For me, because I didn’t get an MFA, no one opened the doors for me, I had to do it myself, and I honestly didn’t know any better not to try. I identify with people who just want to write and make their art and do their thing, whatever that looks like for them, wherever they are.
Yes to all of this! Those of us without MFAs or rich/connected parents or whatever the fuck—we have to carve a different path. Or in my case just thrash through the weeds until something like a path emerges.
Everyone’s thrashing. All we can do is thrash. Thank you, Emily.
Pre-order Emily’s deck here or buy it in the shops next week!
Have a good week everyone.