Bankruptcy to $20k: The Hidden Blessing in My Toughest Moment

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Okay, so let’s get real for a minute. Life doesn’t always go as planned, and sometimes, it feels like you hit a wall that you just can’t get around. That was me—at rock bottom. But let me tell you, there’s a lesson in everything, even in the tough times, and what felt like the worst chapter of my life became the story of how I discovered my true entrepreneurial spirit.

surfboards and paintings on Heidi's art table

Years ago, I found my identity as an art teacher. I was doing what I loved, pouring my heart into my craft, and sharing it with kids. But if there’s one thing I learned along the way, it’s that your identity is never in success—it’s in God. You can be as successful as you want, but if you forget to love on your family and take a breath during the rollercoaster of life, none of that success will matter. Trust me, I’ve been there.

I was going full speed ahead, chasing success and working nonstop, until life literally made me hit pause. We lost everything. Our house, our savings… it all came crashing down, and suddenly, bankruptcy was my reality. I felt ashamed, scared to talk about it. How could I ever face anyone after all that? But guess what? Once I started talking about it, something incredible happened. It set me free.

Turning Pain into Paint

During that tough season, I turned to art to heal. I started painting little surfboards as a way to pour my heart out. I’d bring them to my school (I was teaching 850 kids a week—talk about chaotic) and work on them during my lunch breaks. The kids started noticing.

“Miss Easley, paint me one too!” they’d ask. Over and over again, they’d beg me to paint their names on the boards. And at first, I thought it was just a fun thing I was doing. But after the 150th kid asked for a surfboard with their name on it, a lightbulb went off in my head: I could sell these.

Heidi's family works to cut out wooden surfboards for her to paint and sell

I didn’t have a lot of money. In fact, we were barely scraping by, but my mother-in-law and I came up with a plan. She’d help me buy the supplies, and we’d split the profits. I took the plunge and headed to Panama City Beach, where I set up a booth at Pier Park, a bustling outdoor mall. I rented a 10×10 spot, worked long hours, and… nothing. Not a single surfboard sold.

Talk about frustrating. I had poured everything into this. And what did I have to show for it? Nothing.

Booth set up in Panama City Beach to sell surfboards

The Turning Point

So what did I do? I took a break, of course. My mother-in-law and I headed to Buffalo Wild Wings for a drink (yes, we were both very stressed). Life wasn’t going as planned, and I felt defeated. But then, in the middle of that moment of doubt, my husband called.

“Get over here, Heidi!” he shouted. Confused, I stumbled back across the street to the booth, where Bobby was holding up a stack of paper tickets and telling me, “Heidi, get to painting.” And in that moment, I knew. God scooped me up and said, “It’s going to be okay.”

Heidi and little Pixie paint a surfboard together

I started painting that night, tipsy and all. And guess what? In just two months, we sold over 1,000 surfboards. It wasn’t just about making money—it was about survival. That $20 surfboard was a lifeline for my family.

We were painting in our car, painting late into the night, painting every single chance we got. But we made over $20,000 in just a few months. And I’ll never forget the moment I realized that my passion for art could not only heal me but also provide for my family.

surfboard paintings with paint on Heidi's art desk

The Bigger Picture

Looking back, I smile when I think about bankruptcy. I truly do. It was a tough, humbling experience, but it was a pivotal moment that launched me into the world of entrepreneurship. It taught me about perseverance, about pushing through, and about creating something out of nothing. And now, I get to teach others how to build something amazing, just like I did—one paintbrush stroke at a time.

Heidi looking at her surfboards and taking in a full-circle moment

If you’ve ever faced a setback, know that it’s not the end. It might just be the beginning of something greater than you could imagine. Keep pushing, keep creating, and trust that your hard work will pay off in ways you can’t yet see.

And remember, it’s not about how many times you fall—it’s about how you rise.

Need some inspiration to get started in the paint party business? Check out Paint Party Headquarters for resources, designs, and support to help you create something amazing, just like I did!