We caught up with the brilliant and insightful Annika Wooton a few weeks ago and have shared our conversation below.

Annika, appreciate you joining us today. Have you been able to earn a full-time living from your creative work? If so, can you walk us through your journey and how you made it happen? Was it like that from day one? If not, what were some of the major steps and milestones and do you think you could have sped up the process somehow knowing what you know now?

I’m actually answering this question at a wild and perfect time – this is my last week at my full-time job. I officially put in my notice a couple weeks ago, and I’m stepping fully into the world of live painting and performance art as my full-time career. It’s really exciting, but it’s also mildly terrifying? But honestly, I’ve learned that most of the best things in life feel like both.

I’ve always had side hustles and creative gigs layered on top of whatever job I was doing. I don’t think I’ve ever not been working in some capacity since my first job as the Chick-fil-A cow (True story.) The first time I made money from my art, I was hot gluing pom-poms onto lampshades and selling them at a church craft fair – so if you were one of the people who bought one, sincerely, bless you.

I started freelancing in college – graphic design, illustration, logos, event flyers – charging way under market rate, trying to figure out what I was good at and what I liked. Then in 2019, I was crowned Miss Kansas, and live painting was my talent. That was a game-changer. During my two-year reign (thanks, pandemic), I got booked to paint at events all across the region, and it gave me real proof that this kind of art had traction. It could move people. It could earn income. It could go somewhere with it.

What’s helped me the most in making this leap now is that I’ve spent the last few years building repeatable systems and processes to support the business side of being an artist. Because being a full-time artist means you are also your own booking agent, admin assistant, marketer, travel coordinator, and customer service rep. The more I’ve automated and streamlined the not-so-glamorous stuff, the more space I’ve had to actually enjoy doing the work I love.

I just hit that sweet spot where a lot of things aligned – opportunities were rolling in, my job no longer fit, and I was ready to take a bet on myself. So here we go!

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

I’m Annika Wooton, a full-time live painter and performance entertainer – and yes, that means I paint entire portraits in under five minutes in front of a live audience. It’s part fine art, part spectacle, part adrenaline rush. I often paint upside down and reveal the image with a dramatic flip, which turns confusion and curiosity into full-blown awe in real time. That moment of surprise and wonder is what I live for.

My roots are in visual art – I studied illustration and animation at the University of Kansas, but I’ve always had a passion for performing. My two-year reign as Miss Kansas gave me the perfect intersection of both, as I traveled across the country painting live on stages and at events, often as my competition talent. That chapter helped me realize that there was huge potential in my live painting to pursue as a career.

Today, I work with corporate event planners, sports teams, nonprofits, galas, and national conferences to bring high-energy live painting experiences to their audiences. I specialize in high-impact visual storytelling: turning a moment, message, or mission into a piece of artwork created on stage, right in front of the crowd. My clients come to me when they want to create something unforgettable; something their audience will talk about long after the event is over.

I think what sets me apart is the fusion of excellence and entertainment. I’ve worked hard to hone the technical skill required to complete a compelling painting in minutes, but I also bring stage presence, timing, and strategic design thinking to each piece.

What I’m most proud of is that I’ve built something creatively fulfilling and professionally sustainable. I recently left my full-time job to pursue this work fully, which felt both like a leap and a long time coming. This career lets me create real, unforgettable moments for people and reminds them of the magic that happens when art and performance collide.

My goal is to make the crowd feel something, whether it’s in a packed arena or a black-tie gala. And if I’ve done it right, they’ll want to see it again.

Is there something you think non-creatives will struggle to understand about your journey as a creative?

What I do might look like a 5-minute burst of magic (and in some ways, it is), but what most people don’t see is the hours (and years) behind it. For every performance, I spend time designing the concept, prepping the canvas and paints, curating and editing music, rehearsing with timing, and coordinating all the logistics to make sure the moment lands. There’s also a surprising amount of admin: contracts, communication, travel, gear prep, and filming logistics all have to run smoothly for the art to take center stage.

It’s easy to focus on the final reveal, but that moment only works because of all the work that comes before it. My style of art may be fast, but the foundation is anything but rushed. What the audience sees is a high-energy spectacle – and that’s the goal – but what they’re really witnessing is the result of years of skill-building, intentional design, and discipline behind the scenes.

So I don’t know if that’s something that folks will struggle to understand, but they just might not consider that a huge chunk of the work comes before I ever step foot on the court or the stage.

We’d love to hear a story of resilience from your journey.

There’s a recent moment that I think of when I think about resilience. I had just landed back in the U.S. from my honeymoon — literally on the runway — when I got confirmation for a major speed painting performance at a WNBA game happening that same week. I had five days to prepare for a high-pressure, nationally visible event. Luckily, I’d trusted my gut and started sketching and rehearsing the piece before I left for Greece, even though nothing had been confirmed. I spent the next few days jet-lagged but laser-focused, practicing the painting, lining up logistics, mixing paint, and getting performance-ready. That week was a sprint, but it reminded me that this is a craft I’ve trained for, and a moment I knew how to rise to.

Resilience for me is about building systems, instincts, and confidence that hold up when things move fast. Being a live artist, especially one whose work hinges on public performance, means I’m constantly navigating pressure, timelines, and creative expectations. But those moments of chaos are often the most thrilling and rewarding. They show me how far I’ve come and how prepared I am to keep leveling up.

Contact Info:

• Website: https://www.annikawooton.com
• Instagram: https://www.instagram.com/annikawooton/
• Facebook: https://www.facebook.com/annika.r.wooton
• Linkedin: https://www.linkedin.com/in/annikawooton/
• Youtube: https://www.youtube.com/@annika.wooton
• Other: https://www.tiktok.com/@annikawooton?lang=en