We recently connected with Winslow Dumaine and have shared our conversation below.

Hi Winslow, thanks for joining us today. Earning a full time living from one’s creative career can be incredibly difficult. Have you been able to do so and if so, can you share some of the key parts of your journey and any important advice or lessons that might help creatives who haven’t been able to yet?

I am only recently attempting to make my living off of art, but so far it has been going well.

I’ve worked conventional jobs my entire life, everything from dishwashing to customer service. I recently was let go from a position I held for five years. Normally, that would mean a few panicked weeks of applying for everything I can find, but I spent the last ten years developing my art career into something that made me more money than my desk job. Four years ago, my income from art eclipsed that of my conventional work. Since then, it did so again a few times over, and now I don’t think I’ll need to return to a desk job any time soon.

I was an artist for over a decade without thinking about money. I still don’t think about it too much – I make art because I want to make things that make people laugh or feel awe. I enjoy everything I make. Sometimes the things I enjoy make money, other times, they don’t make as much money. I just enjoy what I do.

Making art to make art and making art for a living are two very different things. I see people pouring their heart and soul into an art piece and then give up when it doesn’t sell. Good art does not necessarily sell. Art is cosmic – it transcends markets, money, everything. If you had some very impactful experience and you create a deeply personal work about your story, but you don’t leave it open enough so that other people can see themselves in it, it might not sell. There’s a reason pop songs are about “my baby” and “my sweetheart” and not “Heather Anne Heimerman, 27, of Neola, Iowa.” A lot of my work is autobiographical in the most expansive possible sense. I take the sum of all my inspirations and visions and pour them into my work. You don’t have to have lived my exact life to appreciate a few of the things I’ve been through.

There is no speeding it up. You just have to keep going and trying new things. The biggest obstacle for most people is time. I know most of us don’t have open blocks of hours on end, but most of us have a lot of little moments. Write your poems on the bus. Draw on your break. Outline a story in an email to yourself while waiting in line. I drafted a number of my most successful pieces on gum wrappers and Post-It notes. If you have a pen in your hand, you are ready to go.

Just remember that art is not a competition and people that make art into a competition don’t really get it. Art transcends hierarchies. Do what is best for you.

That said, if you want your art to support you, you might have to cut into your sleep schedule and pare down your distractions to make room for it. I cannot stress this enough, making good art will likely f*ck up your life. It is stressful. You might gain weight. You might lose weight. Shit, you might lose friends. I lost my hair for a while. It’s intense! You are extracting the rawest psychic matter from yourself and working with it night and day until it takes the shape you desire. My life is absolutely filled with creation and work. None of this is chill. I am literally always stressed. Yet, the stress of something I love is exceedingly sweeter than the stress of keeping it bottled up. And I am no longer scrubbing pots in a 100 degree dish pit. We pick our battles.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

I’m Winslow Dumaine. I’m originally from Omaha, but I live in Chicago. I’m a stand-up comedian, designer, writer, and more recently, a game developer. I started in comedy after watching some local weirdos open for Kyle Kinane in Omaha. I wrote a paper about one of them – Zach Peterson. He suggested I give it a shot. I started drawing more seriously around this time too.

My illustration career began around 2015, when I first decided to draw full-scale images. A few friends asked for prints. I sold a few originals too. I released an ill-advised comedy album that sold a few copies to friends. I went through a pretty catastrophic break-up and I decided to invest my sorrow into my burgeoning efforts in illustration and writing. This resulted in my tarot deck, The Tarot Restless. I made a Kickstarter and raised $14,000 for the first edition. I used to spare resources to create my first pins, fabric patches, shirts, weird water bottles, and surrealist bumper stickers, all of which have become staples of my catalog. I recently ordered the fourth printing of the tarot deck. When those are sold, I’ll have sold a quarter million dollars in tarot cards alone.

I only use the money as a reference point for those who view success quantitatively. I don’t think I’m successful because my art sells, I think I’m successful because I’ve opened up pathways for my self-expression. My goal is to create without obstacles or inhibitions. Money opens the gateway. That said, I don’t spend money on myself, and I live a very ascetic life filled by work and creation.

So, if you know me, you likely know me from the tarot deck or the stickers I make. Discovering the many ways that people know me has been a very fun aspect of this job. People know me from my sticker that says “Gatorade Should Be Thicker”, or they know my comedy performances, or my tarot deck, and more recently, my podcast, I’m From The Internet.

Right now, I am most proud of my forthcoming project, a cooperative card game called THE RESTLESS. The core of the game is for four players to build their characters and fight through an increasingly hostile world of shapeshifting horror. The game is intentionally designed to be very punishing, forcing players to make sacrifices to keep their friends alive. I started working on it a few years ago and within the last five months, I’ve been able to have full play-throughs of the game. I’m stunned by how immediately fun and playable it is – I cannot stress to you enough how crazy it is to essentially write down a sketch of a exquisitely intricate game and to watch it function almost without an issue. Once I’ve written the last portion of the game, I’ll be drawing all 600+ cards by hand. The final project will be huge. I’m honestly thrilled to be able to work on this every day.

Alright – so here’s a fun one. What do you think about NFTs?

F*ck ’em.

NFTs are a scam created and upheld by an unregulated tech industry filled with artless sociopaths. If you watch the video “Line Goes Up” by Folding Ideas on YouTube, he’ll go into more detail. In ten years, they will be forgotten, dust in the wind. Right now, bloodless carpetbaggers are tricking fools into paying small fortunes for two dimensional Beanie Babies that don’t even exist in the corporeal realm.

There is no value in owning the address associated with a jpeg of an ape with a weed hat. I don’t care if they make money. Money isn’t value when it comes to art.

As for A.I. generated stuff, here’s the deal: I think it is art, it just bores me. I have an extremely expansive view of art, one that surpasses almost everyone I know. Contrary to many people, I think A.I. art is, in fact, a kind of art. A machine began at a neutral state, it was given a command by a human, and it generated a result. Using a machine doesn’t make art not art. It’s art, it just sucks and bores me.

I understand people’s hatred of it, and yes, it’s absolutely going to be a huge problem for the industry, but I think that calling it “not art” is a little shortsighted. People protest that A.I. uses stolen art and doesn’t credit artists for copping their entire portfolios, and yes, absolutely, that is correct. But that doesn’t make the product not art. A drawing made with a stolen pen is still a drawing. Stealing a magazine and cutting it up to make a collage still makes a collage. Art is beyond morality.

Digital stuff just doesn’t move me much. Almost all the digital work I’ve seen, and definitely all of the A.I. stuff, has been extremely safe and clean.

For me, art is as much about the artist, their life, and the act of creation, as it is about the final product. It’s all interwoven. There’s a song by Marilyn Manson called Angel with the Scabbed Wings, it’s off his 1996 album Antichrist Superstar. In the middle of it, the music stops and you can hear Manson snort a line of cocaine. In another song on the same album, there’s audio of him overdosing on the floor of the recording studio. It’s raw. It’s the man’s real life. The whole thing is an apocalyptic autobiographical nightmare. A human being lived those moments and created that album. A.I. is a studio band, playing music with straight faces. No soul.

An A.I. can make up a story about an artist’s life, but it isn’t true, so there’s no merit. Normally, I am very much an atheist, but when it comes to the spirit of art, I get very woo. I don’t care if a machine produces an absolutely identical facsimile of a great work of human-created art. Without a human behind it, I just don’t care about it. I want to know who made it and why.

I became an artist to talk about my heart and pain. Computers don’t do that.

A.I., NFTs, that’s just stock speculation for nerds who have cucked themselves with metastasized capitalism.

We’d love to hear the story of how you built up your social media audience?

I know it’s filled with nazis and psychopaths, but I actually love twitter. I love social media. I know it’s killing my brain, but I just can’t get enough. Other people drink, I scroll.

I built my presence online extremely slowly. I have Twitter, Instagram, Facebook, and Tiktok, prioritized in that order. My twitter presence reflects a part of my comedic voice that thrives in the written form of comedy. Some of my tweets are just jokes or observations, but my favorite stuff is written to sound like I’m in another dimension, or like I’m a profoundly strange person living the most bizarre life possible. I love language, and I construct my favorite jokes by building them around a turn of phrase or a word and then building the rest out around that. Lots of weird capitalization, bad spelling and punctuation.

I think regularly working on this character has helped people notice me. Creating a joke, or an idea for a person, and fully imagining it until it becomes a very three-dimensional work, is so much more impactful that just sending out another joke about the current thing. There are thousands of comedians on twitter, seeing topics earlier than me, and writing jokes faster than me. I can’t compete with that. What I can do, however, is be weirder than them. Be more Winslow than them.

If you want to build it up, post about things people are talking about, be earnest, be weird, and put actual effort into it. I see so many comedians with a pittance of followers because they don’t put their heart into it. In all art, in all performance especially, you are selling yourself as part of your creation. Fans want to get access to what makes you, you. You don’t have to give them every bit of your personal life, but give them a little something. Treat it as an aspect of your business, make it look nice, and be consistent. It takes time.

Contact Info:

• Website: www.winslowdumaine.com
• Instagram: instagram.com/calculations
• Facebook: facebook.com/winslowdumaine-artist
• Twitter: twitter.com/winslowdumaine