How I Became a Paid Artist (and how you can too)

There’s an unspoken understanding both inside and out of the creative community that to be a successful artist, you have to have a degree and background in graphic design, advertising, marketing, digital media, or some other creative field. Otherwise, your odds of getting ahead are slim to none.

I’m here to say that’s bullshit.

I’m making money from my artwork and I’m a college dropout. I took a few art classes in jr. high and high school and I was utterly mediocre. I’ve worked office jobs and sales jobs for frozen food processors for almost 15 years. I have zero design background. I have no clue what I’m doing. I didn’t start really applying myself to improving my artistic abilities until I was in my mid-30’s. Literally, the only thing I have is desire. I really, really WANT to be a freelance artist.

So, where did I start? How did I start making money? Where am I going next? Here’s the skinny…..

Where Did I Start?

It was 2014. As I sat in meetings at work, I was doodling a lot. I would sit at home with a ball point pen and a few pieces of printer paper while we watched TV and decided to start posting my doodles to my Instagram account. (If you want to see some of this old artwork, go to my IG page and scroll to the bottom. I refuse to delete my old artwork.)

In 2016, we were gifted a crappy, old chalkboard and I had fun drawing on that. At the time, we were renting a house with my sister-in-law and we would have weekly movie nights. I would draw “movie posters” on the chalkboard. I bought some books, found some interesting artists to follow, and I practiced.

Then September of 2018 happened. I decided to accept the 100 day challenge and it was a game changer. The challenge was to draw or create something every single day for 100 consecutive days. I only had to spend 10 minutes (although most days that turned into WAY more time). By the end of the 100 days, I was significantly better AND I had built a habit of daily practice. If you’re going to be an artist, it takes a lot of work and a lot of experimentation.

Where Should You Start? Practice. Practice. Practice. Practice. Practice.

How Did I Start Making Money?

It took a LONG time before I started making money. Patience is a must. At some point, I felt like I could start working with local restaurants to design their menu boards, daily specials, etc. However, as much as I tried to market myself for that, I WAS NOT READY, I just didn’t know that yet…and that’s okay. Given the amount of time it took me to complete a design, I never would have made money. What I discovered is that the more people that can see my work in person, the more I got paid jobs. That sketchbook that I took on business trips with me? People saw it. I got a few jobs off that. Once I started drawing chalk portraits, I got commissions. Once I started doing sidewalk chalk portraits, I got A TON of jobs. The thing is, you need to practice A LOT. Like, way more than you think you need to. Then you need to let people see your work in person. Art doesn’t always translate on tiny Instagram squares. Showing your work to your community is key. I’ve gotten a ton of support from people in my neighborhood and city. My sidewalk chalk portraits got me featured in a local paper.

That said, I got my first repeat clients by doing customer outreach. I created a 2-page PDF that told people who I was, what I could provide, and showed some of my work. Cold emailing your ideal clients never hurts. The worst they can do is say ‘no’. In the end, it’s really all about trial and error. I tried a lot of things, I failed a lot, and that ultimately led me to the direction I’m in now.

How Can You Start Making Money? Find a place to work publicly. Let strangers stumble upon your work by accident. Talk to people in your community like local business owners about allowing you to use their space for art. Join your city’s Facebook page and share it there. Do whatever it takes but let strangers see your work!

Where Am I Going Next?

I’ve discovered over time that I like making really big pieces. I have a knack for creating them and I truly enjoy those projects the most, despite how physically punishing they are. In a little over a week, I’m going to paint my first mural. I have a gut feeling that murals are going to be a big part of my future and if I’ve learned anything along the way, it’s to listen to your gut.

That said, the other focus of mine is going to be changing my mindset from that of an artist first to that of an entrepreneur first. This business isn’t going to grow itself. I need to put together solid pricing structures, contracts, get liability insurance, create more products that I can sell in my shop, etc., etc., etc. If I start doing more murals, I’ll need to completely redesign my website. I’ll need to hire an accountant. I’ll need to hire a lawyer. I’ll need to get my shit together.

What Can You Expect In The Future? You’ll be doing even more work than you did to get this thing started. It requires organization and planning. You need to have a system in place for managing client meetings and project timeframes. You need to have a system in place for communicating with them (i.e. set up a website and email address). You’ll need a business bank account, a system for payment (I use Square), a contract template, and a good way to keep your audience engaged. Eventually, to be successful enough to do this full time, you’ll spend more time on clerical stuff than you will on art. That’s the harsh reality.

It’s a learn-as-you-go process. There’s no exact roadmap that will fit everyone’s journey. Different people attract different clientele, experiment with different mediums, have different applications, and offer different values to their clients. All I can tell you is that fortune favors the brave and if you don’t try, you’ll never know.