What personal experiences or circumstances have most influenced your work or style? I grew up in the middle of a cornfield in central Ohio, so I’ve always been drawn to artists and writers with straightforward, plainspoken, deceptively simple styles. And I’ve also always been somebody who both writes and draws. So my heroes have been folks like Kurt Vonnegut, Charles Schulz and Lynda Barry—all three Midwestern “writers who draw.” (A description I stole from another artistic hero of mine, Saul Steinberg.)
Is there anything you miss about being a web designer? There’s magical suspense in web design—it’s the moment between when you change a little bit of code, and then you switch over to see what that change does in the browser. I can’t think of anything quite like it in writing or drawing.
You call yourself “a writer who draws.” Do you ever struggle to balance your identities? Yeah, when you do more than one thing, there’s always the old worry that you’ll turn into a “jack of all trades, master of none.” But on the other hand, if you can manage a career that merges a couple of disciplines, the results can be pretty cool. I like to joke that I’m a mediocre writer and a mediocre artist, but I’m a pretty damned decent writer/artist.
You wrote that you hang pictures of your favorite artists in your studio, acting as friendly ghosts who push you forward. Who are they? They rotate. (And they’re not all dead.) Right now I have photographs of Andy Warhol, Lynda Barry, Saul Steinberg, Ed Emberley and Bill Murray drawing a smiley face on his belly.
What inspired you to start your blackout poems? I had just started a blog and I was looking for something to fill it with. I’d been a big fan of the Smoking Gun website, which always posted these redacted FBI files, and I’d come across PostSecret and realized you can have a blog made of mostly images. Something about those two sites and my frustration with trying to write short stories made me come up with the blackout poems. Only later did I find out there’s a 250-year-old history of finding poetry in the newspaper!
You caution against creatives quitting their day jobs to do what they love. Why it is healthy to keep that distinction between your art and your paycheck? My friend Hugh MacLeod calls it the “Sex and Cash Theory.” There’s always the sexy, fun part of the job, and there’s the part that makes money. Sometimes it works better if they’re separate.
When you start making money off what you love, it’s easy to lose what was special about that thing in the first place. It goes something like this: you find something that keeps you spiritually alive, then you turn it into something that keeps you literally alive, and then you have to go looking for something else to keep you spiritually alive! You’re back at the beginning.
I’m not sure it’s a good idea for anybody to try to turn their hobbies into a living. Yet, here we are.
Do you feel like you're “doing what you love” now? What I really love to do is read books and scribble in my notebook. Nobody pays me for doing those things, directly. (Although, in some ways, I became a professional writer so I could be a professional reader. At least I can write books off my taxes now.)
I don’t make a ton of money off my art. The majority of my income comes from my books and my speaking gigs. I make a lot more money from teaching other people how to be creative than from actually being creative. But that’s not much different than an illustrator teaching in an MFA program.
Instead of “do what you love,” I’m fond of one of MailChimp’s slogans: “Love what you do.” Get really good at your job. Throw yourself into it. Become the best at it.
I never really set out for the career I have, but now I want to get as good at it as I can.
Are you practicing art that’s out of the public eye? I really love playing music—I play the piano and guitar and I sing and occasionally write songs (usually for my son). I never got good enough at music to try to make a living at it, and now I’m really glad, because it’s something I can do just for myself.
What's one thing you wish you knew when you started your career? Well, the whole premise of my book Steal Like an Artist is that it was a list of things I wish I’d known when I was starting out, but two things stand out:
1) Nobody cares about you, and you can’t make them care. You have to do or make something for them, and then they’ll care.
2) Live below your means. Not within, but below your means. Financial freedom means creative freedom.
Is there anything you miss about being a web designer? There’s magical suspense in web design—it’s the moment between when you change a little bit of code, and then you switch over to see what that change does in the browser. I can’t think of anything quite like it in writing or drawing.
You call yourself “a writer who draws.” Do you ever struggle to balance your identities? Yeah, when you do more than one thing, there’s always the old worry that you’ll turn into a “jack of all trades, master of none.” But on the other hand, if you can manage a career that merges a couple of disciplines, the results can be pretty cool. I like to joke that I’m a mediocre writer and a mediocre artist, but I’m a pretty damned decent writer/artist.
You wrote that you hang pictures of your favorite artists in your studio, acting as friendly ghosts who push you forward. Who are they? They rotate. (And they’re not all dead.) Right now I have photographs of Andy Warhol, Lynda Barry, Saul Steinberg, Ed Emberley and Bill Murray drawing a smiley face on his belly.
What inspired you to start your blackout poems? I had just started a blog and I was looking for something to fill it with. I’d been a big fan of the Smoking Gun website, which always posted these redacted FBI files, and I’d come across PostSecret and realized you can have a blog made of mostly images. Something about those two sites and my frustration with trying to write short stories made me come up with the blackout poems. Only later did I find out there’s a 250-year-old history of finding poetry in the newspaper!
You caution against creatives quitting their day jobs to do what they love. Why it is healthy to keep that distinction between your art and your paycheck? My friend Hugh MacLeod calls it the “Sex and Cash Theory.” There’s always the sexy, fun part of the job, and there’s the part that makes money. Sometimes it works better if they’re separate.
When you start making money off what you love, it’s easy to lose what was special about that thing in the first place. It goes something like this: you find something that keeps you spiritually alive, then you turn it into something that keeps you literally alive, and then you have to go looking for something else to keep you spiritually alive! You’re back at the beginning.
I’m not sure it’s a good idea for anybody to try to turn their hobbies into a living. Yet, here we are.
Do you feel like you're “doing what you love” now? What I really love to do is read books and scribble in my notebook. Nobody pays me for doing those things, directly. (Although, in some ways, I became a professional writer so I could be a professional reader. At least I can write books off my taxes now.)
I don’t make a ton of money off my art. The majority of my income comes from my books and my speaking gigs. I make a lot more money from teaching other people how to be creative than from actually being creative. But that’s not much different than an illustrator teaching in an MFA program.
Instead of “do what you love,” I’m fond of one of MailChimp’s slogans: “Love what you do.” Get really good at your job. Throw yourself into it. Become the best at it.
I never really set out for the career I have, but now I want to get as good at it as I can.
Are you practicing art that’s out of the public eye? I really love playing music—I play the piano and guitar and I sing and occasionally write songs (usually for my son). I never got good enough at music to try to make a living at it, and now I’m really glad, because it’s something I can do just for myself.
What's one thing you wish you knew when you started your career? Well, the whole premise of my book Steal Like an Artist is that it was a list of things I wish I’d known when I was starting out, but two things stand out:
1) Nobody cares about you, and you can’t make them care. You have to do or make something for them, and then they’ll care.
2) Live below your means. Not within, but below your means. Financial freedom means creative freedom.








