How I Became a Live Wedding Painter

Have you ever had something unexpectedly pop off on social media?

Like, one second you’re casually posting photos of your puppy on Instagram… and the next thing you know, you’ve gained thousands of followers, been invited onto Oprah, and have three different kibble companies begging to sponsor your adorable little fur child.

That is kind of what my jump into the live wedding painting world felt like.

When people asked me as a child what I wanted to be when I grew up, I never once responded:

“A live wedding painter.”

Painting my second ever live painting along the coast of Florida

Heck, I didn’t even know live wedding painting existed until roughly three months before I graduated college. For most of my time as a college student, I assumed that if I wanted to pursue the fine arts as a career, I'd need to make art and sell it at crazy high prices in big galleries. Or I'd need to make lots of cute prints on Etsy and do 'shop drops' each month. Or I'd need to paint a mural so large and impressive that it'd pay my bills for the next 6 months.

None of those things sounded super appealing to me.

Table of Contents

It Began With A Scroll

Do It For Free

My First Live Wedding Painting

For Aspiring Live Wedding Painters

It Began With A Scroll

So when I accidentally stumbled across the Queen of Live Wedding Painting (in my opinion) on Instagram, I knew I'd found something special. I stalked Maggie Kuhn for hours. With wonder and delight, I realized that she was able to travel around the world, dressed in the most gorgeous clothes I'd ever seen, meet new people, eat good food AND make a living as a full-time artist????

A whole new world of possibilities suddenly opened up before me.

(Fun fact: I finally got to meet my Maggie in person last year. She was dope.)

And from that point on, I couldn’t stop thinking about live event painting. Soon after my big discovery, I graduated college and officially jumped into full-time entrepreneurship (read more about that journey here). At the time, I was primarily supporting myself through commissioned artwork while trying to figure out how I could book my first live wedding painting.

And during those first few years of running an art business, I learned one of the most important lessons about entrepreneurship and creative marketing:

People often don’t realize they want something until they’ve seen someone else do it first.

Every time I introduced a new type of commission into my portfolio- pet portraits, house portraits, tattoo designs, you name it- I would almost immediately see an increase in inquiries for that exact service. People needed to see what was possible before they could imagine it for themselves. Which meant if I wanted to become a live wedding painter…

I first needed a live wedding painting in my portfolio.

There was just one tiny issue.

How exactly was I supposed to book my first wedding if nobody had ever seen me paint one before?

Simple.

I offered to do one for free.

Do It for Free

Honestly, free art is one of the most effective marketing tools known to mankind. I have yet to meet a single human being who has turned down the offer: “Would you like free custom artwork?”

At the time, none of my close friends were getting married anytime soon, and I did not feel particularly interested in waiting the potential 10+ years it might take some of them to settle down. (And no, for some of my friends, that timeline was not an exaggeration.)

Then one day, my mom casually mentioned that the child of a family friend was getting married.

Bingo!!

I immediately messaged the family and explained my offer: Let me come create a live wedding painting for portfolio purposes, and in return, I’ll gift the finished artwork to the couple afterward.

Thankfully, they said yes. I had officially booked my very first live wedding painting!

Cue the panic.

Suddenly, I had to figure out what supplies I needed, how live event painting setups worked, what timeline I should follow, how quickly I could realistically paint people, how to create content from the event, and whether or not I had accidentally overestimated my abilities entirely.

Naturally, I returned to the Queen’s Instagram page and began aggressively researching. And by “researching,” I mean pausing videos, zooming into screenshots, and spending an objectively concerning amount of time trying to identify everything she used. (It was only after roughly three hours of detective work that I discovered she had an entire supply list with affiliate links on her website. Humbling.)

I took some of the money I'd won from a business pitch competition and used it to buy my first live event painting supplies, including a plein air easel, a massive painting supplies backpack, and a clamp on lamp.

Then I created an entire content strategy for the event. Because yes, even back then, I understood that social media marketing would play a massive role in growing my art business.

Lastly, I practiced speed painting people. It was rough.

I'd never even taken a figure drawing class in college, let alone studied actual lessons on how to drawing human beings and their likenesses. Which is unfortunate because the human body and face is often considered by many artists to be one of the most challenging things to try and draw realistically.

And they're very right.

I mean, think about it- if you have just one angle off, one limb too long, one tooth a bit too crooked- it can throw off an entire portrait! But the entire appeal of becoming a live wedding painter, at least for me, was the ability to quickly and skillfully create emotionally compelling portraits in front of a live audience.

So I started doing speed sketches of different bodies, faces, genders, ages. Any images I could find on the internet, I would spend 30 minutes at a time doing 30 second, one minute, ten minute, even 30 minute portraits. I studied my art books, reading up on theories about how to mix skin tone and proportion a body.

In other words, I prepped as much as I could.

My First Live Wedding Painting

Finally, the wedding day arrived. My mom, one of my biggest supporters throughout my entire artistic journey, seemed as nervous as I was about this live painting thing as we drove up together.

Arriving, I set up my station while silently praying I hadn’t forgotten anything critical, and then introduced myself to the wedding planner for the day (AKA the backbone of any successful wedding.) The moment I explained that I was creating a live wedding painting, she lit up.

"OH MY GOSH, are you really???" she asked. "I have SO many clients who have been asking about hiring a live wedding painter, but I can never find one locally! Can I post you working on my page?"

Thrilled, I eagerly agreed, giving her a follow online and promising to tag her in my upcoming content for maximum reach. And then I began my first live painting

Me with my first live painting

During our consultation, the couple had requested a painting of their first dance. From my research, I’d learned that many live wedding painters arrive several hours early to begin sketching, blocking in the composition, and establishing the background before the main moment occurs. So I arrived roughly three and a half hours before the ceremony. By the time the first dance rolled around, I had the majority of the background established and was finally ready to add the couple.

All evening long, Brittany, that fabulous wedding planner I'd told you about earlier, took photos and videos of me working and posted it on her social media, tagging my pages.

By the end of the night, the painting had turned out shockingly well. (Thanks in no small part to my wonderfully detail-oriented mother occasionally popping her head over my shoulder throughout the evening to offer feedback.) The reveal was lovely. The couple adored the piece. Heck, I adored the piece. And most importantly? I finally had my first live wedding painting portfolio piece.

I packed up my supplies, drove home, crawled into bed completely exhausted, opened my phone…

…and discovered 16 brides sitting in my Instagram DMs asking to hire me to paint their weddings.

And that's how I became a live event painter.

From that very first wedding onward, my career rapidly expanded. I traveled throughout West Virginia and eventually across the country creating live wedding paintings for incredible couples from every walk of life. Now, nearly five years later, I have painted over 120 weddings.

It has been one of the greatest adventures of my life.

For Aspiring Live Wedding Painters

For aspiring artists reading this, I think the biggest lesson I’ve learned throughout this journey is this:

You do not need to have your entire career figured out immediately.

Sometimes the opportunities that change your life the most are the ones you accidentally stumble into while simply staying curious, continuing to create, and being willing to try something new. You also don’t need to wait until you feel perfectly “ready.”

If I had waited until I felt fully qualified to become a live wedding painter, I probably never would have started. Sometimes growth happens because you leap before feeling completely prepared. And sometimes? All it takes to change the course of your life is one free portfolio project, a supportive mother, a little entrepreneurial delusion, and a very good Instagram algorithm.

(Also, please know I will be writing a 'how to post' on my tips and tricks for becoming a live painter soon.)

Interested in seeing the live wedding paintings I’ve created throughout the years?

Feel free to explore my portfolio and follow along as I continue documenting my journey as a live event artist, entrepreneur, and full-time creative.

And if you happen to be a couple searching for a live wedding painter for your own celebration?

I’d be honored to help tell your story through art.