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How to Become a Successful Artist: A Conversation with Michael Dowling

According to Denver-based visual artist Michael Dowling, there’s something radical about selling your art. It’s the act of defying the expectation that you can’t succeed. It’s the realization that you’re doing exactly what you want to be doing. If you’re an artist—struggling or thriving—or someone who wants to create but hasn’t lately, give this a read. We had the opportunity to speak with Dowling about his artistic journey and how to become a successful artist. His advice: be an artist in whatever you do, sell your art, and follow that dream.

Can you tell me a little bit about your artistic journey? 

Yes, actually I had a very interesting journey getting to where I am. I taught myself how to draw pretty realistically quite young. Later on, I went to Colorado State and studied Mechanical Engineering and thought that would be the direction I would go in. And, it just quickly burned down. I was not focused and I did a terrible job of being a student. At around 25, I was starting to get to the end of a Philosophy degree and had to take a painting class to fulfill a requirement. From the minute I walked in there, I thought, “This is what I’m going to do for the rest of my life.” 

I hadn’t really painted before that. I started way later than a lot of artists do. From there, I dove straight in. I quit my retail job and got a job with an art and sales company. I started painting and drawing all the time. I started my own corporate arts consulting firm, had that for about a year and a half, and then decided I needed to focus more on just making art. I sold half of the business to my business partner and I moved to Italy. Really quite suddenly. I didn’t speak Italian, but I just knew I wanted to be in Florence. 

On a Friday, I made my decision. On Monday, I told my business partner that I was leaving, and by the next Friday, I was in Italy. 

Just by the craziest luck, I got into this weird little school and met these teachers who are still my mentors today. I spent a few years studying with them. Then I moved back to the States. I did all kinds of things to support myself and my family at first. I sold copiers and did a marketing thing for a used car company. I sold wine for a while, which was nice. Then I finally left the working-for-other-people-world about seven years ago—and started being an artist for a living. 

What was that decision like? You walked into that art class and immediately knew this was what you wanted to do? Did you ever go back-and-forth about it?

Nope. Not even a minute. Yeah, it was really interesting. One of the things that really helped was in that art class, the teacher had been a marine. He came with this very different attitude towards being an artist than I’d ever seen. I didn’t have a sense of how an artist could be anything other than the sloppy, messy, you know, throw-paint-around-in-the-studio kind of person. And this guy, John, was extremely organized. He set up his pallet, his brushes, everything, in the same way, every day, and painted in a certain order.

I’m very organized. I like math, and I like having a system about things. I like keeping things clean. The moment I saw that I could already incorporate all of the things that I already had ingrained in my life: being organized, being clean, being a hard worker, and making art with those things, I was sold. Because art was already the thing that I loved doing. 

It was not a decision. It was the most natural step into something that I could have ever taken. 

What is your advice to someone who wants to be an artist or is struggling to sell their art? 

So, you actually have two jobs when you’re an artist. The first one is making things and the other one is showing things. As an artist, you have to be patient. It’s going to take a while. Very rarely does an artist make something, they sell it, and they’re living as an artist. It doesn’t work that way. 

On Making Things

You need to impress yourself.  If you’re impressed with your work, you’re going to impress other people. 

You should be making things that you are so floored by that you kind of say to yourself, “Holy sh*t I just made that?” If your work is not moving you that dramatically, then it’s not going to do it for anybody else. 

You have to make so much work that it’s just kind of crazy. Just keep going. Keep painting. Make something every day. Schedule at least 10 minutes, if not an hour or two, to making art, every day. Sit down at your table or stand at your isle and just be there until you start making the marks. 

On Showing Things

Then, as far as the business of being an artist, you have to make a plan for yourself to make money. You have to get very organized. You need to have an event every month that’s creating an opportunity to sell your work. 

So, at the beginning of every year, I make a calendar. In that calendar, I break it down by month and quarter. If every month I want to make at least $10,000. In order to do that, I need to have a major show, and probably a couple of minor things. And so I start filling in my calendar and making sure I have an event every month. 

If I don’t have anything, I will call my mom and ask her to have a show on her refrigerator. 

You know, whatever it takes to get that activity going. I don’t always sell at each event, but because I had that event scheduled, it means I’m making work for it. It means I’m putting that work out not only on social media but it’s also in the studio when people are walking through. People are seeing it. So, even if I don’t sell at that show, it’s creating sales opportunities elsewhere. 

It’s just a numbers game. If I show my art to 1,000 people, 100 are going to like it, 10 will be collectors, and one will actually buy something that day. It’s a thousand people walking past my work to get it done.

What is the value in selling your art versus just making your art? 

Anytime you’re making art, it’s a beautiful thing. And, there are definitely artists out there who never need to sell a thing and that’s actually really noble and really cool. I wish I was driven that way to make art. But, a lot of my drive has to do with making money off my work. 

There’s value in selling your work. When you make art and sell it, all of a sudden, it’s gone. And it’s a really valuable driver for you as an artist to sell it and see it go out in the world and see other people value it in the ways that you do. Then it’s up to you to replace that piece of your soul that is no longer in your life. You might not replace it with something exactly the same or even similar, but you’re making new work to replace what you sold.

On top of that, it’s a chance to participate in a different way in the very weird world of our economy. I take a piece of paper and a piece of charcoal and I make a bunch of marks and somehow that makes me money. It’s very strange. But it’s even weirder when you go and sit at a desk and hit a bunch of computer keys and somebody pays you for that. 

Nobody makes things anymore. It’s a rare thing in our world for people to actually make a living off their art. When I was in Italy, one of my teachers, Rose, was asking me, “What do you want your art to be about?” I told her, “I don’t know exactly what the voice of my work is going to be or how I’m going to take on ideas in my work, but I know that one of the things I want is to make a living off being an artist.” And she said, “That’s one of the stupidest things I’ve ever heard.”

I had to explain to her that nobody actually gets to do this. That learning how to be a successful artist meant learning how to make money, too. That few get to follow their calling and their dream like this, and I’m actually going to do that. That is my art. My art is to live as an artist—to make my living and my way in the world as an artist. Doing that is actually a bigger revolution than any of the art I can make. 

Now that you are making a living as an artist, what else is your art about?

In the art that I make, there is a voice and conversation going on. I’m always exploring the stories that come back time and time again in our society. When you look at old legends and myths and biblical stories and things like that, a lot of them repeat in different societies and different ways, just the characters are changed. Sometimes people intentionally steal the story and make it their own. Or, sometimes there’s a story that’s so iconic that there’s going to be the same kind of story in another culture. 

More recently, I am very interested in being in the West and our American history. The founding fathers seep into my work in many ways. Images that are maybe my own mental construct of a founding father that we don’t really know the story of. I’m making up my own history and legends for our place, which doesn’t have the long long history of these other places in the world. Kind of my own secret stories we don’t get to hear from in our history. 

Who is an artist?

Everything that everybody does. It doesn’t matter what you do, if you do that thing beautifully, you’re doing the same thing I’m doing. My wife didn’t understand it for a long time. She cooks really well, and I would always explain to her that I don’t want to cook because she gets the same kind of benefit from making a great meal as I do from making a great painting. I don’t want to take that from her because I get to make my paintings. Most of the things that you can do in the world, if you take it in that way, you’re doing the same thing I’m doing. It doesn’t matter if you run a retail store, if you’re doing that beautifully, you’re doing it.  

Everybody can be and is an artist in their own way. The only real difference between me and other people is I’ve decided to take my obsessiveness about it to a level where I’m making an income and I’m making it my profession.

Keep Up With Michael Dowling

If you’d like to keep up with Michael Dowling and his artistic journey, check out his website and Instagram. In the meantime, you heard Michael, set aside some time to create every day. Find ways to do your work—whatever it may be—with the skill and beauty of an artist, even if your job seems the farthest from it.

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