Daily Inspiration: Meet Annika Wooton

Today we’d like to introduce you to Annika Wooton.

Hi Annika, can you start by introducing yourself? We’d love to learn more about how you got to where you are today?
Sure! I’ve always said that I’ve been an artist ever since I could hold a crayon. My path has always been creative, but it took a lot of experimenting (and stage time) to figure out how to blend everything I love into one career.

The first time I speed painted was in front of my entire high school at an assembly during my senior year – and I didn’t practice. My very first live painting was in 8 minutes, upside down, with no practice. So when I started competing in the Miss America Organization and needed a 90-second talent, I thought, “well if I just practice, I should be able to get this down,” and that’s where the REAL speed came into play.

From there, it grew into a full and beautiful career. I started getting booked for corporate events, galas, fundraisers, and even halftime shows. I’ve now performed coast to coast—from Hawaii to D.C.—painting everything from company founders to NBA mascots to WNBA first-round draft picks… live and in real time. It’s wild.

My goal has always been to blend high-energy entertainment with real artistic storytelling. I want audiences to be captivated the whole way through, and then totally floored when they see the final painting revealed. That moment of “wait… WHAT?!” never gets old. It’s what I train for.

Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
Absolutely not. And I think that’s what makes the wins feel even more meaningful.

Building a career as a live artist isn’t exactly a path with a clear playbook. There were (and still are) seasons where I’ve had to hustle hard, wear every hat in my business, and keep creating even when I felt uncertain about what was next. I’ve worked through burnout, creative doubt, and the instability that comes with being a self-employed artist and performer. I’ve also had to learn how to price my work, advocate for myself, and build systems behind the scenes so that the art on stage looks effortless—even when it’s anything but.

One of my blog posts talks about the “in-between”—the quiet times when you’re waiting for the next big thing, and trying to keep trusting that it’s coming. I’ve learned that those stretches are just as important as the busy ones. That’s where I sharpen my tools, refine my process, and stay grounded in why I do what I do.

At the end of the day, it’s a creative life. And creative lives aren’t smooth, but they are incredibly worth it.

Thanks for sharing that. So, maybe next you can tell us a bit more about your work?
I’m a speed painter and live performance artist, which basically means I get on stage with a blank canvas, a handful of brushes, and about 5 minutes to blow people’s minds. I paint everything from iconic portraits to custom pieces tied to a brand, cause, or event theme, and the whole performance happens live, often to music, in front of a crowd.

What sets me apart is the way I’ve blended visual art with stage presence. I think I’ve mastered creating a painting that I’m proud of that’s paired with a big reveal, energy, pacing, and the “how did she do that?” moment when the crowd realizes what’s been taking shape upside down the whole time.

I’ve performed at everything from WNBA halftime shows and national galas to corporate retreats and nonprofit fundraisers. I’m most proud of how I’ve built a business out of something that didn’t have a clear path. I grew up as a theater kid and with art supplies always at my finger tips, so this has turned out to be the perfect blend of my childhood loves. And now I get to bring that magic into rooms and stadiums across the country.

There’s a lot of technical training and behind-the-scenes strategy that goes into each performance, but at its core, it’s about creating moments people remember. That’s what I’m in it for.

Networking and finding a mentor can have such a positive impact on one’s life and career. Any advice?
My biggest advice is probably to just start by showing up. Show up to events in your industry. Show up online with your work. Show up for other people first – that means commenting on their posts, celebrating their wins, offering your skills when it makes sense. Most of my best connections came not from “networking” in the traditional sense, but from building real relationships over time where I didn’t expect anything in return.

When it comes to mentors, I think the word can feel big and intimidating, but I think mentorship can look like a lot of things. Some of the most valuable mentors in my life have been fellow creatives, business owners, or performers who were just a few steps ahead of me. I haven’t necessarily needed someone at the very top or in my very niche industry – I’ve needed people who believe in my wild ideas, are willing to challenge me and brainstorm with me, and have lived enough life to have a wider perspective to guide me or calm me when things get tough.

Also: don’t be afraid to ask questions. People love to share what they’ve learned, and showing curiosity is one of the best ways to build trust and connection. You never know who’s watching your work, and one authentic relationship can change everything.

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