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

Hi Kristin, thanks for joining us today. It’s always helpful to hear about times when someone’s had to take a risk – how did they think through the decision, why did they take the risk, and what ended up happening. We’d love to hear about a risk you’ve taken.

I come from a dynasty of band teachers. My parents were both band teachers, although my mom switched to a different area of teaching when I was in elementary school. My brother is also a band teacher. My dad went to the University of Minnesota, I went to the University of Minnesota, and, you guessed it, my brother went to the University of Minnesota. I have been a middle school band teacher for 17 years. Band is safe for me. I know what I’m doing, and I’m good at it. Teaching is safe for me. I grew up in a house that had three different spring breaks and summers off all together. Teaching makes sense to me.

After my son was born, I went back to teaching full time. And it was hard. My music program was suffering from the aftermath of COVID, and budget cuts were looming, which meant I wasn’t going to be able to provide my students with the music education I knew they deserved. In addition to being a full-time teacher by day, I was full-time parent as soon as I got home. I was really struggling because I no longer had time for my myriad of hobbies – my creative pursuits that made me me. With my husband’s encouragement I took a part time leave of absence at school to save another music teacher’s job, and to have time to do the things that made me feel like myself. Like painting.

I have some beautiful friends who had recently had some beautiful weddings, so I asked for their favorite wedding photos, and I painted them. I wanted to see how quickly I could paint, and if I could try out some new techniques. I had so much fun painting these people I loved with their loves on their wedding days. I got dinner with a friend who is a wedding planner and asked her if there was a market for paintings of people’s wedding photos, and explained that I was toying with the idea of seeing if I could turn art into a career. She encouraged me to look into live wedding painting. Painting live? In front of people? With acrylics? But I’m an oil painter. I hate acrylics; they dry too fast and they frustrate me. No, I cannot do that. I cannot paint live. But she pushed until I agreed to try it.

So I started looking into live wedding painting and what other painters do. I found a community of artists making a living…being artists. I didn’t know that was possible. I was scared. I didn’t know any profession aside from teaching, but I was burning out and needed to find something new. I didn’t know how to make market myself, I didn’t know how to make a contract, I didn’t know how to set my prices–I didn’t know how to run a business. How was I going to do this? After talking with my husband, who is very familiar with my infinite passion for new artistic adventures, and we decided to give it a go. I would stay teaching part-time for as long as I could, and while doing that, I would start my art business. Safety, familiarity, and something new, inspiring, fresh, and scary.

I’m coming up on two years from this decision to make this jump, and I’m so much happier than I was before. It took about 9 months for my business to really get off the ground. I started by doing some weddings for free, because you can’t practice live wedding painting without a wedding, and then I took a course from an incredible, experienced wedding painter. After having a few weddings and the course under my belt, I felt so much more confident. I met my stretch goal for how many weddings I wanted to book in my first year, and now I have clients inquiring over a year in advance. I feel like my life has much more balance now. I teach, I paint, and I get to be a mom and a wife. I don’t get to do all of my former hobbies, but art was my first love, and my strongest. It never occurred to me until a couple years ago that I could actually turn it into a career. I’m not a big risk-taker. I like things to feel safe. Going part-time at school and starting this business was one of the biggest risks I’ve ever taken, and I’m so glad that I did.

Kristin, 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 a middle school band teacher for 17 years, and have always been able to maintain art as a hobby on the side. I have been a mother for three years, and when I returned to work full time after my son was born, I suddenly didn’t have time for anything else. I was a full-time teacher by day, and full-time mom by night. I felt like I was losing the things that made me me. Looking for options, I met with a wedding planner friend and asked her if there was a market for paintings of people’s wedding photos. She said, “Yes, but there’s a better market for painting live at weddings.” I said, “That sounds terrifying. I’m not doing that.” To which she replied, “Well, you’re going to try it anyway.” With her encouragement, I jumped into my painting career. I took a part-time leave of absence from school and started my business.

Now, I paint live at weddings and I love it. Weddings are full of love and joy, and it’s just so fun to be surrounded by smiling people, all there to celebrate love. I love interacting with guests, hearing their stories of the couple, and seeing just how important these two people are to everyone in the room. It’s also an incredible honor to be immersed in these special days. I also really love painting from photos. Photographers can work magic with lighting and camera angles, and it is so fun to get to take that to the next level by turning it into a painting. It feels like a collaboration, and sometimes painting these photos really does feel magical.

I’ve also recently added pet portraits to my repertoire, and those are pure fun. I almost feel like pet portraits serve me more than they serve my clients, because I’m just an animal lover and want to love on all the pets. I’ve even been known to add pets into wedding paintings without an additional charge sometimes because I see how important the pet is to the couple, and I selfishly just want to paint them, too.

Some of my favorite paintings that I do are nursery paintings, and I think that is something unique to me. I don’t see other artists really advertising custom nursery paintings, but they are some of my favorite commissions. Bringing a baby into your family is such a special journey. My own son was conceived through multiple rounds of IVF, and my pregnancy was rocky, leading to a premature birth. I have friends who have adopted children, friends who have adopted embryos, friends who have had egg donors, friends who have miscarried, friends who have used surrogates, friends who have had sperm donors, and friends who have brought their babies into the world “normally” without any complications. Babies are special, and the journey to bring them here is special, so I really love to work with soon-to-be-parents to give them a unique piece of original art to welcome their special little one into their family. These are some of the paintings that bring me the most joy, and this is unique to my business.

What I most want people to know about my business and me is that I want you to have original art in your home that is meaningful to you. I don’t want your home filled with the same things that are in everyone else’s home. I want you to have art that speaks to you. Something that you look at and can’t help but smile at, even on a dark day. True art speaks to your soul and connects to your heart. I want to help you bring this to your home.

Are there any books, videos or other content that you feel have meaningfully impacted your thinking?

The resource that has helped me the most in this business is Stephanie Gaffney’s (of Torregrossa Fine Art) Wedding Painter’s Blueprint course. I found Stephanie as soon as I started my journey as a live wedding painter, and found her to be a wealth of knowledge. She answered any question I emailed her with, which is a not something everyone will do for a stranger from the other side of the country. I dedicated all of my free time in spring of 2024 to her Wedding Painters Blueprint course, and it helped me from start to finish. She taught about the business and legal side of things, with contracts, client management programs, pricing your services, and even website and SEO presence. She covered materials, supplies, and equipment for live painting, and of course had several weeks of actual painting lessons. Her course also gave me a community with a critique group, which has been invaluable. It helped bring me into this community, and it has helped us truly build a community where we support each other, instead of seeing every other artist as a competitor.

What can society do to ensure an environment that’s helpful to artists and creatives?

I think the most important thing we can do is to continue to fund and support creative classes in our schools. Art and music programs around the country are dying. Every spring, art and music teachers are advocating for their students, begging their administrators to keep them in the schedule, to make sure they have staffing to provide a quality education for their students. Music, art, and other electives get cut all the time without the public really realizing it.

Music programs are often staffed to offer small group lessons to students to better learn their instruments, and without them, students really struggle. The lesson staffing can get taken away without the public realizing that they are starting to lose their music program. What you can do today is reach out to the school board or principal, or other administrators in your district and tell them how much you value music, art, and other elective classes. These are the classes that foster creativity. These are classes that cannot be replaced by AI. No machine can make art like a human can. No machine can make music like a human can. The arts are unique to humans, they’re part of what makes us human. We aren’t machines. We are able to problem solve, be flexible, bring soul and feeling to something. And this is special because the performer or artist feels it, and so the does the audience or viewer.

I truly believe that if Americans were aware of how little creative time their kids get in schools, they would want to do something about it. When budget cuts happen to schools, arts and music are the first things to go. We are always the first sacrifice, and it is at the expense of our children, and our future as a creative society. If we want to be a country of inventors and innovators, of people who are compassionate and care for one another, we need to fund arts and music in our schools better than we do.

Contact Info:

• Website: https://www.bykristinchase.com
• Instagram: @kristin.chase.art – https://www.instagram.com/kristin.chase.art/
• Facebook: @bykristinchase – https://www.facebook.com/bykristinchase/
• Other: Etsy – https://www.etsy.com/shop/artbykristinchase

Image Credits

Kalyn Wolf (the two photos with me in them)