Alright – so today we’ve got the honor of introducing you to Jolie Theall. We think you’ll enjoy our conversation, we’ve shared it below.

Jolie, appreciate you joining us today. Can you talk to us about how you learned to do what you do?

Since being laid off in August of 2024, I decided to learn to paint. I have painted every day. Completing at least one painting a week while constantly trying new techniques and more difficult subjects. Learning to paint in a year has involved taking on one painting at a time as a challenge. Each challenge has been based on the limit of my imagination of what I was capable of and what skills I assumed I had at the time. With each painting, I tried something new and something that felt more difficult. Sometimes I’d be at the canvas, afraid to put down paint. Fearful that I’d mess up what I’d already done and wouldn’t be able to get it back or wouldn’t have the skill to make it look as good as I wanted it to be.
Over the last year, I have fifty to one hundred paintings, including 25 high-value keepers, four of which are from 2024.

It is interesting that in 2024, I was using big canvases, but then I realized I didn’t have that much wall space. Most recently, I’ve created a six-canvas series consisting of 9 x 12-inch canvases and spent the weekend working on seven portraits in a spiral sketch book. It’s a very compact way to work. While my quality has dramatically improved, I’ve learned to be much more efficient with my use of space.

Jolie, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?

I have been learning to paint in a very organic way. Initially, I would just look on YouTube or the internet for free lessons and copy what the teacher did. Then I had enough skill that I started to draw inspiration from photos that I found or took. I kept challenging myself with each painting; they got harder and harder. My first paintings were huge, which is easier, though the canvases and paint are more expensive and cumbersome. Eventually, I discovered the benefits of using smaller brushes, which allowed me to achieve more detail and realism. The more realistic and detailed they are, the more I like them, so I do see myself going in that direction. Although I still sometimes enjoy going fast and rough. Like this last weekend, I painted seven portraits from photos. Some of them are so rough that the brushstrokes are very prominent, but they capture the essence of the person. When they capture their spirit, often I am done within an hour and ready to move on. I am currently taking a five-week class at Barnsdall Art Park, and it will force me to slow down and take the whole three hours to go back and add more layers and detail.

I am currently focused on learning the craft of being a contemporary painter. I have demonstrated that I’m a skilled painter, and people appreciate my work. I have the luxury of having my basic needs met through my retirement, which is enough to cover my rent and food, plus I do a bit of freelance web design for a queer events company. So I have the luxury of just waking up and being an artist every day. However, I still would like to find a way for my art to reach a wider audience than my studio, and that is one of my following challenges.

So, I am also turning my painting into a business. That is a business that sells and shows original paintings as well as prints.

I have reviewed three different business tools and have finally settled on one, although I still have some additional research to do.

The creative independence that having a base income affords me allows my creative life and creative flow to be completely independent of my worries, or whether something will sell. At the same time, I have a background that motivates me to explore how to monetize my strengths.

I have a lifetime of experience working with other businesses and my own former software business, which I ran for twenty-three years until 2010. My goals have always been to raise more money, attract more customers, and provide a better experience – and usually all of the above.

So I feel pretty confident that eventually I will find a way – if there is a way – to paint, enjoy creating, find places to show my work in more places than just BlueSky and my website such as galleries, and to have a profitable store where you can buy originals, posters, print canvases, and even items such as coffee mugs and shower curtains. I have already set these up in a limited way on my website.

What do you think is the goal or mission that drives your creative journey?

There is something I’ve been thinking about my work lately, and I’m not sure if I can capture it, but when you consider my art and my career, the state of my business and momentum on this day of this year is entirely devoid of anything except art. I am producing art. And the art is free from goal, mission, purpose, or direction. And that’s OK. It is beautiful and free. I know that I am productive, but I don’t care how productive I am, and nobody else does either. I painted six portraits over the weekend. And one more this morning. Three or four were good. I posted two or three. Including one for a subject who knew it was of them. They said it was ‘Sick.’ It was sick. That made me very happy. It makes me want to paint more sick paintings. The whole painting was done in a matter of minutes, and you can see all the quick, fast brushstrokes. It is not at all polished or trying to be precious, but it captures their twinkle. It captures them. It captures their essence. It makes me want to kiss the painting, and I don’t even know them except online. And that is why I want to paint. That ‘is’ sick.

What’s the most rewarding aspect of being a creative in your experience?

As much as I love it when people like my posted art on socials or I love it when my friends text me that they love my paintings, because I do get a lot of pure joy from those interactions, the deepest most lasting rewards that fuel the most lasting feelings that I receive as an artist is when I am faced with the fear of a creative challenge such as working with an live model – which I have yet to do but have lined up a willing subject – to just doing a portrait of someone who will see it – which recently happened. Facing that challenge, feeling the fear, embracing it, and doing the challenge anyway, I showed myself that I am capable of figuring it out or navigating the challenge and emerging on the other side with a result that is not too shabby. This is not only very rewarding but also gives me great hope for where I will be in a year or two, or even ten.

Contact Info:

• Website: https://theall.design
• Other: My main social is BlueSky. This is where I have the closest and largest artist and supportive artist community ‪@jolietheall.bsky.social

Image Credits

All Paintings by Jolie Theall