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

Alright, Giovanna thanks for taking the time to share your stories and insights with us today. We’d love to hear the story of how you went from this being just an idea to making it into something real.

Imagine, a 5-year-old finding you crying in the bathroom because you want to hide the fact that you are totally overwhelmed from her and her brother. As their entire world had just shut down, school, friends, sports, to the walls of our home and our family of four, my world was about to open up in a way I had been waiting for my entire life. That is how it all started. In the early days of the pandemic, I was waking up at 4 a.m. every day so I could squeeze in a few hours of work before the kids needed help with school. I was taking conference calls with sleepy children on my lap, trying to keep everything afloat and as normal as possible. meanwhile… I was melting down.

When my daughter Julia found me crying in the bathroom, her words changed my life. She said, “Mom, you always say how much you love to paint, but I’ve never seen you do it. I think you need to paint.” She was right. I had not picked up a paintbrush in 20 years. Even though I had painted murals during college breaks for extra cash.. I never saw Art as a way to support myself…. but that all changed that day.

I started small. I watched every YouTube video and free tutorial I could find and taught myself watercolor. Instantly, it became a reprieve from all the chaos around me, a way to quiet my mind and feed my soul. As the days of the pandemic went on, my family and I found a rhythm, a schedule that combined work and play, walks around the neighborhood, and art. Lots and lots of art. For two years, I painted for me and me alone.

As I built up my confidence, I started to share small bits of what I was creating on social media. Suddenly, friends and family were asking for paintings for their moms’ birthdays, or a way to remember their dads’ memory. My mind started to stir. Could this be more than just a hobby?

As a woman in the professional world, I had always worked. I took my standard three-month maternity leave and, because I was taught to never get off that corporate ladder, I went right back to work, never having seen my kids get off the school bus. Working from home during the pandemic gave me a gift of being with my kids I never knew I needed, and I didn’t want to give it up. Could art, something I had long loved but never seen as a “real job,” be a way to hold onto this newfound balance of motherhood and career? Could I really start a business at 42? Yes. I believed I could. I didn’t know exactly what business I wanted to build, but I knew what mattered. I wanted something that uplifted artists. Something that gave women the chance to financially support themselves and their families, while still having the flexibility to be the moms they wanted to be. I wanted freedom.

When asked if I would create a set of notecards, I decided to give it a go. I YouTubed my way through “How To” everything, from scanning my art, using Photoshop to remove the background, and finding the best paper. I looked into packaging, printers, and envelopes. How do I price this? On and on and on. I printed 25 sets of notecards, posted them on Instagram, and set up a free Square account. I sold 10 boxes and thought, okay, let’s keep going. Next, I created two more designs and signed up for my first Christmas craft fair, a three-day event. I invested $1,500 of my own money and created my first booth. I thought I would sell out. I didn’t.

It was the beginning of 2023 and the world was opening back up. People were eager to get out of their homes and back into their communities, and I wanted to be part of it. I saw creators all over Instagram and thought, if they can do it, I can too. So I kept going. I felt it. There was something here, and I loved the rush of it all. After being in my stale job for nearly 25 years, this felt new and exciting. I loved meeting people and hearing their stories.

I decided 2023 would be my year of yes. I would try all things and say yes to as many opportunities that came my way. I was waking up at 5 a.m. and working on my business until the kids got up at 7, getting them out the door and then myself to work. Then working after they went to bed at night. By August of that year, I had missed my son’s first home run, and I was exhausted, not to mention all my hard work earned me a grand total of $12,000, and who knows how much I invested. I knew this wasn’t it, but still, I continued.

One day, I happened to see a woman I had never met post that they were looking for vendors for an influencer event. With no real plan, I reached out and asked if I could live paint at the event. When she said yes, I knew this was an opportunity and I didn’t want to mess it up. I hired a social media/marketing strategist. She helped me create small pieces of watercolor paper with my information printed on the back. I rented a pretty dress, planned a sleepover for my daughter, ordered Chinese food for my son and husband, and even curled my hair in New England August humidity. I was ready.

That is until I got to the event and they had forgotten a setup for me. I had no table, no chair, and the wind was immediately taken out of my sail. I was embarrassed and ready to go home. But I didn’t. I stayed. We found a glass console table from the entryway of the venue, a chair from the lounge, and set me up right next to the bar.

What happened next was nothing short of magic.

The event host asked if I could paint her. Another curveball. I was skilled at painting flowers or cocktails, but people? Could I do this? I dug deep into my memory and remembered a fashion drawing class I had taken in college. I figured I would give it a go. Then the next guest asked for the same, then the next, and on and on. The buzz and joy surrounding my table filled me with an energy and a sense that this was a pivotal night in my life. Event guests found refuge in me, a place to come and watch art unfold, a place to regulate and escape, and then walk away with a small piece of art created just for them. I knew immediately that I had stumbled on something big here.

My mind was racing. What just happened? Over the next few days, my Instagram blew up. People were reaching out and asking if I could come to their event, to their store, or if I could paint a portrait for their daughter, sister, mother. Of course I said yes. I had no clue what I was doing, but I knew I could figure it out.

Again, I went back to doing research. I found that although there were some live wedding painters, nobody in New England was live painting guest portraits. I started to expand my search. What were people charging? Should I charge by the painting, hour, or a flat fee? What size paper should I use? How do I make it more efficient? I took my first job for not nearly enough money, but it didn’t matter. I was learning. Every job I did, I learned more and more, and before I knew it, in the last four months of 2023 I more than doubled my yearly income.

In 2024, I made the very hard decision to let go of every part of my business that wasn’t live painting at events. I went all in. I put blinders on and refined my system, something that could be repeated again and again. I was still working my full-time job, going to events at night and on weekends, squeezing in all the kids’ and family activities and feeling on top of the world. That was until my foot caught on my too-long jeans and I went flying down my wooden stairs and broke my tailbone. Again, I was embarrassed, defeated, and this time, in a lot of pain. Again, I found myself at a pivot point. I had taken the business as far as I could alone. If I wanted to go further, I couldn’t be the only one.

So I created a team.

I started to look for artists who were the best in the area but didn’t offer live painting. Once I found one, I shared my system, then asked if she had any friends. And so we grew, one artist at a time. We created a team that could rely on each other, a circle of supportive women, not in competition but in community, and we grew. I focused on booking events that could bring the team together so people could experience what it meant to create in community. I started staying home more and focusing on the management side of the business, the brand, and growth. I could now see a real business and not just a side hustle.

I am proud to say that today, Art Experienced is a team of female live artists criss-crossing New England and beyond, creating joy through art and human connection. We now live paint guest gifts at all kinds of events, from private weddings to fundraising galas to magazine celebrations. We partner with national brands such as Patrón, Rhone, and Delta to create art that reflects their stories. As a business, we are able to pay our artists well, and they are able to balance family and personal life with career goals. And I am most proud to say that in September of 2025, I was able to give my notice at my full-time job and pursue Art Experienced full time.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

I am a lifelong creative person. I grew up on my grandmother’s sewing room floor, playing with scraps of fabric and buttons to create whatever was circling in my mind. When I wasn’t there, you could find me drawing, painting, or watching Bob Ross.

My family immigrated from Sicily in the late 60s on my grandmother’s sewing-skills visa. The gift of America providing opportunities for anyone willing to work hard was ingrained in me from a young age.

I am proud to say that I was the first person in my family to graduate from college. I went to Syracuse University and, although I loved art, I didn’t know that ART could be a real career, even though I was using that exact skill to pay for school by painting murals during holiday and summer breaks. While at Syracuse, I found Interior Design, which became a career I loved and was successful at for 25 years… but it still wasn’t enough. I needed more.

That need led me to create Art Experienced, a company focused on live painting at corporate events, private celebrations, and brand activations. We are a team of artists dedicated to spreading joy through art and human connection. With a team of over five artists, we are able to scale each activation to create the desired impact. Because we have systemized our process, you and your guests know exactly what to expect and what the final outcome will be.

We offer four main services:

1. Live painting of guest gifts, such as fashion portraits, seashells, cocktails, and more.

2. One large painting that captures the scene of the event and is retained by the host.

3. You Create Experiences, where we encourage guests to find peace and respite in painting and creating at large-scale events.

4. Brand partnerships and collaborations that align with your company’s story and audience.

These activations are designed to engage guests and create a positive, dynamic atmosphere. They provide a pause within a larger event, giving guests a moment to absorb the health and wellness benefits of watching art being created, or even making it themselves. Guests then leave with a piece of the art so they can always remember how special the event felt and how deeply their hosts appreciated them, enough to gift them an original piece of artwork.

Can you tell us about a time you’ve had to pivot?

My entire story is about pivoting in midlife, but if I really drill down to the why, I would say it’s because I had more to give, and my 9–5 no longer provided a place for that growth. I had been in the corporate world my entire adult life and truly believed that was the definition of success. That is, until I realized how limited my control over that success actually was.

When you work for a company, you are hired to fulfill their mission and their agenda. They control your salary, your title, and the opportunities you’re allowed to pursue. When I was passed over for a promotion with no real explanation, I knew that if I wanted more, I would have to go and create it myself.

Starting my business was about many things, but at its core, it was about having the freedom to build a life I am proud of, with no limits. Leaving my safe, full-time career after 25 years of building a reputation has been one of the hardest things I’ve ever done, but I am confident that in order to grow, I have to take this leap.

Are there any books, videos, essays or other resources that have significantly impacted your management and entrepreneurial thinking and philosophy?

0x Is Easier Than 2x by Dan Sullivan and Benjamin Hardy changed both my business and my life. I recommend this book to everyone, entrepreneur or not.

This book breaks down the traps and lies we often tell ourselves and guides you toward understanding that you can work smarter, not harder. As a mom, wife, and woman who started her business alongside a full-time job, I had to become incredibly strategic and efficient if I wanted to grow without burning out. One of the main messages of the book is to focus only on the things that actually move the needle and let go of all the other noise.

This forced me to look at some of my services and leave them behind. I had been holding on to products like notecards, prints, and painted earrings that were lower value, yet they were taking up as much, or more, time than live painting, which is more intense, focused work but for a shorter timeframe. After applying what I learned from this book, I’ve seen my revenue triple over each of the past two years.

I shifted my mindset from “I have to do all the things” to building deep expertise in one thing. Being the expert in one area is much easier to market than trying to be everything to everyone. And I remind myself often that just because I’m not marketing those other creative services doesn’t mean I can’t still explore them as an artist.

Contact Info:

• Website: https://www.artexperienced.co/
• Instagram: https://www.instagram.com/giovanna_chaisson/
• Linkedin: https://www.linkedin.com/in/giovannachaisson/

Image Credits

Mariah Gale