How I began my Career as a Minnesota Live Wedding Painter

I get asked a lot of the same questions at weddings.

“How do you do that?” (Practice!)
“Where did you go to school?” (A small Christian college in Arkansas.)
“Will it be finished by the end of the night?” (No, but it’ll be close! I take them all home to carefully double check & add details.)
…etc!

One of the most common questions I get asked is, “How did you get into this?” I have a shorthand version that I tell guests, because I don’t want to sit there and bore them with the full story (“I used to be an art teacher, and a friend of a friend asked if I would try painting live at her wedding. I don’t know how to say no, so I said yes, and the rest is history!”) But, for the sake of putting it out there somewhere… here’s the full story, probably far too long but that’s all right – hardly anyone is going to read this anyway and that’s okay!

My husband and I graduated from Harding University in Arkansas in May of 2019, were married a month later, and then moved straight to Alabama (a state we NEVER anticipated living in, Nathan being from Texas and me from Illinois). We were Mr. and Mrs. Stout, K-12 music and art teachers, and I’m still so proud of those titles. With classrooms right across the hall from each other, I still like to compare that time to a Hallmark movie. It was fun, crazy, and exhausting – especially because we both had to write all of our own curriculum for the whole gamut of ages.

Labor Day weekend of 2021, two years into teaching in Alabama, I was at the beach on a bachelorette trip for a friend. One of the other bridesmaids, Kaitlin, was also engaged and we were chatting about her wedding. Knowing I’m an art teacher and having seen some of the small-scale originals and commissions I’d been offering at the time, she asked if I had ever heard of live wedding painting. Crazy enough — I hadn’t! It was going big on TikTok at the time, but being a high school teacher and having been personally bugged by students using it in class every day, I was pretty darn opposed to TikTok just on principle. So she showed me some examples, and opened my eyes to a whole new opportunity. Now — at this time, I was simply doing commissions as a (VERY) small side gig, and never ever foresaw (or honestly even wanted?) a career in fine art. I was NOT a risk-taker, and still don’t consider myself to be one. I majored in art education specifically for that reason – being a teacher was much more stable an option than being a solo fine artist, and stability is important to me. However… I just never could have foreseen how God was going to bless this!

I wasn’t someone who loved to paint in public, but I’m also a textbook people pleaser, so when Kaitlin asked me at that bachelorette party on the beach if I would try painting live for her wedding, I said — Maybe. And then I promptly forgot about the conversation until she reached out a few months later to talk details. I don’t know what prompted me to jump in to the deep end and say yes, but eventually I did. I had the preexisting skill – landscape and plein air experience, some portraiture (admittedly not enough, but that has continued to grow with experience), as well as good practice habits instilled in me by a decade playing the clarinet, and a crippling fear of letting people down. I was ready to go!

So, I started practicing in January of 2022 knowing that Kaitlin’s wedding wasn’t until October, because I wanted to have plenty of time to see where my weaknesses were and work on those, as well as try to slowly increase my speed. (spoiler alert: I haven’t actually gotten all that much faster in 3 years, and I’m perfectly fine with that because I’ve learned that trying to force speed leads me to mistakes, that cost me more time and headache later.) I started with my own wedding photos and produced a really cute little painting of our first kiss, that I would handle TOTALLY different if I were to have another go at it today. Artistic growth is an amazing thing.

As I was beginning to practice, I mentioned to a friend about my upcoming live painting, and this friend mentioned me to her cousin who is a full time photographer with many connections in the wedding industry. (Friends, get yourself some ride-or-dies that will mention your name proudly in rooms of opportunity. This has brought huge unexpected blessings for me multiple times throughout this journey, and I’m trying to be that for others.) This photographer graciously put me in touch with an INCREDIBLY talented and experienced live painter local to the Gulf Shores area of Alabama, Melissa Munger.

Melissa’s generosity changed my life. She didn’t have to meet with me. She didn’t have to let me shadow her at a wedding (February 18, 2022), she didn’t have to let me hover anxiously over her shoulder and teach me her hard-earned tricks of the trade, she didn’t have to bring me along with her to paint my first wedding ever (March 20, 2022) and invite me over to her house to work on painting touchups together, and she didn’t have to recommend me to clients for going on four years now. But she did. It is AMAZING how quickly we bonded and how quickly she became one of my best friends — and she still is. That first wedding painting together with her was incredible, and I was so surprised by how much fun I had, rather than anxiety, and how well I did despite the pressure. I’ll remember it forever, and not just because I forgot to bring my white paint on the first day on the job. March 20, 2022 was my first live wedding painting with Melissa, and she shared our adventures on her social media.

Over the next week, I gained 200 followers, most of them other artists, and received around a dozen inquiries for my live paintings, and I was woefully unprepared for this explosion of interest. So I super quickly had to put together a contract to give out, set up a skin-and-bones website with an inquiry form for interested couples, and figure out my pricing. I had such a great time at my first wedding that I was SO excited to take on some more (of course still never expecting to have done ANY before Kaitlin’s wedding in October!) However, at this time Nathan and I already had plans to move to Minnesota at the end of the school year in June, so I only really had 2.5 months left in Alabama. This actually worked out great to get me started – I advertised super low pricing with discounts to brides who had maybe considered a live painter but didn’t have the budget, and were able to add me on super last minute for the next 2 months only. I believe I was only charging $500-850 depending on canvas size. And I ended up doing 6 live wedding paintings before moving!

All this time, I was REALLY seeing the interest and getting lots of inquiries that I was unfortunately unavailable for (since I’d be moving soon), so I started pushing ads up ahead of me to Minnesota and Wisconsin, with new pricing, advertising a 25% off “gift to my new service area” sale. It worked like a charm. Of course, I did learn some things, like I should have placed a limit on how far out weddings could be booked with this sale, because I was still painting 25% off weddings in the fall of 2023 when at that point I had a whole year and a half’s worth of experience! But, you live and learn and I’m very proud of how the business grew even when moving at the very start of my business! And I am massively grateful to God for blessing these efforts far beyond what I could have ever foreseen. When we got to Minnesota, I already had enough weddings booked that we decided that I didn’t need to apply for teaching jobs. Unbelievable.

By the time I got to Kaitlin’s wedding at the end of October 2022, I already had 15 live wedding paintings under my belt, and was able to be very proud of what I presented to her. And the fact that she took a chance on me — what?! God really just flings some of the most unexpected doors WIDE open.

So, that’s how it happened! With God’s incredible plans and a lot of hard work, late nights, business expenses and miles on our cars, we’re here now, starting my fourth year as a full-time live wedding painter serving Minnesota and the Midwest, with very nearly 100 painted love stories under my belt. It’s been a beautiful and crazy journey, one I look back on and say, “Why did we do that? How did we not fail taking these huge risks?” But God has blessed us and sustained us more than I ever thought possible. I can’t wait for the next 100 weddings.