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5 Uncomfortable Tips to Becoming a Successful Artist

Earlier in 2017, I was selected as a Professional Fellowship winner in painting by the Virginia Museum of Fine Arts. Ever since, I have had people ask me what I did to win. Some were asking specifics on how I categorize my work. I noticed that others were asking in the way you ask for a secret family recipe or for the way to beat a final boss on a video game. I’m not going to tell you how to paint better or write better music. In fact, you will hate the advice I am about to share, but it is meant to be challenging and, at times, frustrating. It’s not about what you want to hear but what you need to hear. 

1. Define Your Version of Success

What do you want to be doing? Where do you want your work to go? Nobody else is going to help you define your goals and, yet, everyone will tell you what real success means. Time to put your big boy pants on and put some real thought into why the hell you’re doing this. Your benchmarks will evolve and change over time as you progress. Success to an artist who has a full-time job is going to be different than someone who is creating full-time. Start small and then grow.

2. Work Hard at Doing Good Work

If you don’t have a gauge of what is good in your current field, then this will only ever be a hobby to you. It’s true that “good” is subjective. Follow good work so that you can recognize good work. This will give you perspective. Listen to podcasts about your craft. Visit galleries and museums showcasing your favorite artists or works. Go to concerts of your favorite bands. Read authors whom you admire. Take what you pick up and practice it. Nobody can teach you drive and ambition. That’s on you.

3. Realize That You’re Not Special

I have been fortunate to have the support from my wife, my parents, my family and my friends. They think that I’m the greatest that there has been, and I love them for that—but with an incredible network of support must also come personal perspective. I am not saying that you need to go tell them to take a hike. What I am saying is that there are a billion people on Earth right now who are doing the same exact thing as you. And there were billions before you. And there will be billions after you. They painted that same thing you did. Come to terms with doing what you’re doing for you and have the drive to want to do it regardless of the fact that other people are, too. Stop comparing yourself. Stop creating because you think it’s unique.  

BEWBS. Carl Medley. 2014, 32”x8” Acrylic on skateboard

4. Create for the Gap

When someone looks at a piece of art or reads a poem or listens to a song, there are gaps. These gaps lie between the person and the art, as well as all around them. You need to decide whether your work contributes to those gaps or is superficial. You should always be creating in contribution to your story or dialogue or experience. I don’t mean that your work has to be super deep, but if you are painting a landscape because it’s a landscape, that’s all you will ever be to anyone. You will be forgettable. This is where that question of “What’s the point?” should be creeping into your head. If someone ever asks you that question, and you don’t have an answer, say goodbye forever. 

5. Share Your Work

I saw a Facebook post once that said, “Done is better than perfect.” Stop hiding your work. Let people know that you are working and trying and practicing and sucking and getting better and scared and happy. You will become paralyzed if you only ever show the final thing because you didn’t want people to know that you’re a human. People are interested in your work because they’re interested in you and in your point of view. And if you’re not sharing any of your work at all, well, I guess you don’t exist. Bummer. 

Great book by Austin Kleon about sharing your process with the world.

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