Meet Winslow Dumaine | Illustrator, comedian, game designer.

We had the good fortune of connecting with Winslow Dumaine and we’ve shared our conversation below.

Hi Winslow, why did you pursue a creative career?

If I wasn’t doing art, I’d lose my mind. I don’t say that to sound cool or mysterious, I say it because there are many parts of traditional career paths that I am simply too incompetent to perform adequately. Outside of working in a kitchen, every job I’ve ever had has been exceedingly dull: my work week was 40 hours of busy work, repetition, and empty space. My head, though, was constantly spinning with ideas. I wrote half of a novel during my shifts at Barnes and Noble. I drew half of my tarot deck while taking calls for Ritz-Carlton. My creative urge superseded the demand of tasks that couldn’t keep my attention. Maybe I thought were beneath me – arrogant, I know. I’d rather draw and write jokes than work on TPS reports or whatever. I was laid off last summer, though, and I haven’t even thought about going back to a regular job. I create full time, and it really is full time. I spend more time drawing and designing my art during the day than I did doing actual work at any of my previous jobs.

But art isn’t just creation. I know scores of artists who create fabulous works and then panic and give up when the time comes to publish, promote, and sell them. I’m not saying you have to do those things to be an artist – art is art even without capital, social, and historical compensation – but if you want to live off your art, you have to make yourself visible. People confuse that with being an influencer, or trying for the throne of some extremely well established artist, but it isn’t that at all. Those influencers and artists already are what they are, and you almost certainly can’t do it better. Often, your largest and most realized self is more interesting than the most marketable version of you.
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Let’s talk shop? Tell us more about your career, what can you share with our community?

People love to ask that – what sets me apart from others – and I never have an answer. I very intentionally avoid comparing my work to that of other artists or smearing the work of other people. It’s funny, every so often I’ll have some dickhead on instagram or twitter or whatever who will get into the comments on my art posts and say “You think this is great art? You think you’re talented? You suck!” But the reality is no, I don’t really think I’m that great. Don’t get me wrong, I’m a fan of the stuff I make, that’s why I make it. But describing me as great implies a vertical scale of art, and I just don’t believe in that. Really truly. The best art, to me, is the art that startles me and makes me really feel something. I care more about a performance artist crawling around through concertina wire than I do about the 10,000th Hyper Realistic Painter Who Only Paints Hot Women. Realism – that’s what bores me. Why are you making art about what already is? I’ve already seen what is. Show me what ain’t.

When it comes to the challenges, it might sound cool and intellectual to say that the challenges are all within, like internal battles with the ego and the self worth that are won over time. Maybe it is – those are hard to measure. I certainly love myself infinitely more now than I did five years ago. But the real challenges are money, time, commitment, and approval, and they’re all intertwined.

Money is obvious, but it’s not just about having the money to make art – if you’re resourceful, you can make art out of anything. Stop saying you can’t, and start asking how you can. But if you’re flat broke, you’re going to spend more time worrying about rent than you will making art. That will sap you. I can’t really give advice on how to go from flat broke to doing okay without knowing the story of who I’m talking to, so I can’t really go into that here. If you have enough to get by, then you can do your best to make time to create. You have filler time. You’ll find space. You might lose some sleep, but if you want to create, you gotta let it kill you a little bit. Commitment and approval are deeply intertwined, at least for me, and definitely right now. I’m deep in the work on my next project, The Restless, a 4 player card game set during the last days of human extinction, and my god, it is hard to get people to notice it. I have vast piles of art to share, but when I post it, I get a few dozen likes, and I’m like, shit, that doesn’t feel good. Makes me want to give up. When I post my face, or jokes, the algo loves it. But art? Nah.

But I’ve been nothing before. The first ten years of my artwork are almost completely forgotten. I started at zero and I got up to speed. I just need to remember what it feels like to be nothing. I think that’s the most important part of my career: I spent a decade being completely ignored. I know how to fail and not give up. I’m a weed. My roots are deep, I’ll survive the winter, and even if you pull me out, I’m going to come back.

Any places to eat or things to do that you can share with our readers? If they have a friend visiting town, what are some spots they could take them to?
Well, here’s the thing, I have never lived in Tennessee. I could suggest a few comedy bars in Nashville. I understand you folks love blues, so I would suggest finding somewhere to get some blues in. If you’re in Chicago, though, go to Wolfbait and B-Girls, Transistor, and Eskell. Contemporary Art Museum is good. Wicker park is worth a day at least. Catch a show at Lincoln Lodge. I would also suggest going to the older parts of downtown and admiring all the rust and decay. That’s my favorite part of the city.

Shoutout is all about shouting out others who you feel deserve additional recognition and exposure. Who would you like to shoutout?

It’s hard to pick a single person to credit because I take inspiration from so many. Kyle Kinane, Dave Ross, Ben Roy, those guys really helped me discover myself in comedy and regularly offer support and advice. For art, though, a lot of that is very independent. My friends and companions have all helped guide me when it gets dark. The gals at Wolfbait and B-Girls and Rafael from Transistor, two great local gift shops, have believed in and supported me in my most challenging hours. Many people have helped me become what I am, and this is why I am always very eager to help as many others as possible. Truly the only reason I want success is to give it to others.

Website: WinslowDumaine.com

Instagram: instagram.com/calculations

Twitter: https://twitter.com/WinslowDumaine