Story & Lesson Highlights with MOLLIE MASON of Cleveland

We’re looking forward to introducing you to MOLLIE MASON. Check out our conversation below.

Good morning MOLLIE, it’s such a great way to kick off the day – I think our readers will love hearing your stories, experiences and about how you think about life and work. Let’s jump right in? Are you walking a path—or wandering?
I feel that I am walking a path, but at my own pace. Right now, I’m focused on slowly building my art business while also balancing the demands of raising two young children on my own and working full-time as an elementary art teacher. It can be a lot to juggle, but I’ve learned to honor the season I’m in and give myself grace as I move forward step by step. Even with limited time, I continue to book 10–12 events a year, and I look forward to the day when I can dedicate even more energy to growing my business. For now, I see each event and inquiry as both a gift and a sign that I’m exactly where I need to be on this journey.

Can you briefly introduce yourself and share what makes you or your brand unique?
My name is Mollie Mason, and I’m a 32-year-old self-taught artist from Grafton, Ohio. During the week, I work as an elementary art teacher, and on the weekends, I bring my passion for creativity to life as a live wedding painter and guest portrait artist. I balance this work alongside raising my two wonderful kids (ages 6 and 2), plus a busy household with two labrador retrievers and a cat. My journey as an artist began about 10 years ago when I fell in love with painting and started creating every day—before long, people began showing interest in my work, and what started as a personal passion has grown into a business where I book several events each year. What makes my brand unique is that I capture special moments as they’re happening, creating keepsakes that couples and guests can cherish forever.

Thanks for sharing that. Would love to go back in time and hear about how your past might have impacted who you are today. Who were you before the world told you who you had to be?
Before the world told me who I had to be, I was pretty lost. I worked part-time jobs, wandered through college, and wasn’t sure of my purpose. About four years ago, I was saved by Christ, and that changed everything for me. Shortly after, I found myself on this creative path—teaching art and building my business, Mollie Mason Art. I had originally pursued a teaching career, but I didn’t fall in love with my work until I stepped into the art classroom and began painting live for others. That’s when I finally felt aligned with who I was meant to be.

Was there ever a time you almost gave up?
Yes—at my very first wedding, I almost gave up. It was a windy day at Mapleside Farms, and in the middle of the ceremony my easel blew over, taking the canvas with it. Everyone heard it, and I was so embarrassed. On top of that, my equipment wasn’t working, so I couldn’t transfer the couple’s image onto the canvas. I remember standing at the sink, filling up my water jar, with adrenaline rushing through me and thinking I had failed. But after about an hour, my equipment finally worked, and I pushed through. I finished the painting, and the couple absolutely loved it. That moment taught me resilience and reminded me that sometimes the hardest starts lead to the most rewarding finishes. It took about three weddings to work out all the kinks, but that experience gave me the confidence to keep going.

So a lot of these questions go deep, but if you are open to it, we’ve got a few more questions that we’d love to get your take on. What are the biggest lies your industry tells itself?
One of the biggest lies in the live painting industry is the belief that an artist’s work isn’t good enough and that they must undercharge just to secure a booking. Art is subjective, and most of the time, couples are drawn to the artist just as much as the finished piece. It’s important for artists to stay true to their style—allowing it to evolve naturally over time—while still honoring their own voice. Undercharging not only undervalues the artist’s work, but also the work of others in the same field. Live painters and guest portrait artists create something truly unique: heirloom pieces that capture a couple’s love story and can be cherished for a lifetime, even passed down through generations. Pricing should reflect not only the time and materials used, but also the years of dedication and practice it took to develop their craft.”

Thank you so much for all of your openness so far. Maybe we can close with a future oriented question. If you retired tomorrow, what would your customers miss most?
If I retired tomorrow, I think my customers would miss not only my artwork, but also the joy of seeing me share behind-the-scenes moments of creating it. Many of them have followed along as I’ve grown as an artist, and it would feel bittersweet to see that journey come to an end. The thought of never creating again would be devastating, not just for me, but for those who have supported and connected with my work over the years.

Contact Info:

• Website: https://www.molliemason.art
• Instagram: art_by_molliemason
• Facebook: Art by Mollie Mason
• Other: Tik tok- Mollie Mason Art