How to Start an Art Career: My Accidental Start as a Sidewalk Artist

How did I become a professional artist? Honestly, by accident. It all started on a sidewalk in Florida, and it wasn’t exactly glamorous.

First, the painting

This painting has already lived a few lives. It started as a watercolor, then became my acrylic mixing palette, and now it’s the foundation for these orange juice bottles. Keep that in mind, because it ends up being a pretty good metaphor. For more on painting over old work, see paint over an old acrylic painting.

Want to Paint Loose Acrylics, Slacker? Learn the fundamentals, loosen up your brushwork, and develop your own expressive style.

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A bamboo bike and an art supply store

Years ago, I lived in Florida and ran a bicycle rental shop with my girlfriend and business partner. One of our customers was a local arts and crafts store. One summer day, they called while we were slammed. A customer had bought a bamboo bike and needed it assembled.

I picked up the box, built the bike, and returned it. But while I was in the store, I wandered back to the art supplies. Brushes, tubes of paint, stacks of crisp white watercolor paper. I’d loved art in school but hadn’t done much since. I thought, “I’d love to get into art again.” Then I went back to work.

When life fell apart

A few months later, my girlfriend and I had a falling out. I sold my share of the business and stepped away to figure out what to do next. After things settled, I got bored, and I kept thinking about those juicy art supplies.

So I went back, bought paint, brushes, and paper, and started doodling and experimenting. I wasn’t trying to start a career. I just wanted something creative to do.

A new friend, a new job

I kept returning for supplies and met a fellow artist who worked there. We talked painting and became friends. As winter approached and the tourist town slowed down, he said, “Why don’t you come work with us?” So I started part-time.

A month later, I had some people over, and I had a pile of paintings stacked in the corner. My friend looked through them and said, “Wait, is this your work?” He was genuinely surprised. Until then, I’d mostly kept my paintings to myself. His reaction made me wonder if other people might connect with them, too.

The sidewalk idea

Being the entrepreneur I am, I pitched the owners: put me outside as a sidewalk artist. I’d paint in front of the store and sell my work, and people could go inside and buy the same materials I was using. They liked it.

When spring arrived, I set up on the sidewalk and started painting. People stopped to watch, asked questions, and began buying my work. That was the moment everything changed. Complete strangers liked what I did enough to spend their money on it. I thought, “This is real. Maybe I can actually make this happen.”

None of it was planned

I went into that store because someone needed a bike assembled. Later, when part of my life fell apart, I went back because I remembered brushes, paint, and clean watercolor paper in the back. One thing became something else, and then something else again.

Just like this painting. So don’t be too quick to dismiss an old painting or an unexpected turn in your life. You may be looking at the first layer of something much bigger.

From selling art on the sidewalk to my garage studio, I just kept showing up, kept painting, and never quit. See my garage studio and how to find your own art style.

Learn Structure. Paint Loose.

Construct. Deconstruct. Explore. Repeat.

Starting an art career FAQ

Do I need a plan to become an artist?
Not at all. I didn’t have one. I just kept painting and showing up.

How did you sell your first paintings?
I set up as a sidewalk artist in front of an art supply store and painted where people could watch.

Do I need formal training?
No. Curiosity and consistency matter more.

What if I’ve fallen out of practice?
Start small. A few supplies and some doodling is enough.