Outside the Box: Sailing into the Sunset with Melody DiCroce

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“I need a change. A big one. I can't stay here and keep doing this the rest of my life. And if you want to step off this train now, I completely understand. But I'd love you to join me. I don't know what will happen. We may end up in riches, or we may end up in ruins. But I promise you one thing: it will never be boring.”

How would you react if your partner threw that proposal at you? If you’re Melody DiCroce, you would tell him you’re on board.

At the time, Melody and Chris were living the American dream. With a house, a pooch, and a great group of friends in the city of Nashville, Tennessee, they spent their weekends relaxing on their 27’ sailboat. Melody loved the company she was working for, although it was a small one that wasn’t capable of paying her what she was worth. Chris had taken a break from his singing/songwriting career and was employed in the film industry. He didn't love his job, but he did have one.

Since Chris had stepped back from music, some of his songs had been licensed to a major motion picture. While the film didn’t get released, Chris and Melody did get an opportunity to preview it. As the film unraveled a typical suburban family’s dysfunction, Chris and Melody started to recognize that their own dissatisfaction came from the same source, the source that the film took its name after. The name of that movie?


The two had become so complacent in their lives, the lives that our culture tells us all we should desire, that they weren’t pursuing their own dreams.


Their dreams came in the form of that 27’ sailboat. After delivering his ultimatum to join him in radical change, Chris had offered up the idea of living on a boat. Melody was initially against it, and a compromise they headed to coastal shores to find their new home on the land side of the dock. Melody remembers the search. “We took several trips to look here or there, and it was like Goldilocks. This town was too small. This one would be too cold in the winter. We couldn't quite find our ‘just right’—at least not in the limited time we were able to see some of these places in.”

With each town they saw and didn’t fall in love with, the sailboat idea started sounding less crazy. Sailing was their activity of choice when they were living in Nashville. They loved to travel. They could spend summers in the North with family, and sail south when the leaves started to change. With the realization that they could go wherever they wanted, whenever they wanted, Melody had a change of heart. “We could finally be free,” she recounts.

Of course, in order to maintain that freedom they needed money. Melody was all too aware of this when she handed in her notice to her boss. In that moment, something amazing happened. “He asked if I'd be willing to stay on and work remotely from the boat,” says Melody. “That took a lot of pressure off, and that's when I knew we'd be okay. We could make it work.”

Make it work they have. On top of her job for the small company she was in love with, Melody started picking up side jobs while at sea. To document her extra income, she created the site Saving to Sail, where she also aims to inspire others as they get their hustle on.


She started realizing that hustling wasn’t a way to maintain her lifestyle, though. “I began to realize that if you spend your life trading dollars for hours, you'll work yourself to death trying to keep topping the previous month. So I just launched my new website called Entreprenista, where I help other female entrepreneurs grow their business online.” With a new course launching in January, she’s shifting from a service business model to a digital product business model. “I'll be setting myself up with a passive income stream that will give us ultimate freedom, and allow us to travel more.”

As she builds her business, Melody enjoys reaping the benefits of living on a 35’ sailboat. The freedom and mobility prevent them from falling back into that place of complacency. “I find that we make fewer exceptions on what and who we allow into our lives,” she explains. “If a place isn't doing it for us, we don't have these excuses at work in our heads for why we should stay. We simply say, ‘Time to go,’ and we untie the dock lines and sail to our next destination.”

While they’ve endured some hardship since embarking on their new life, from family emergencies to periods of financial struggle, Melody wouldn’t trade it for the American Dream they gave up those years ago. As Chris, now her husband, promised, it’s never boring.

She encourages others to step away from boring, too. Even if they don’t think they’re financially ready. Even if they don’t think it’s possible.

“Do it. Do it as soon as you can. If it doesn't work out like you thought it might, you can always change your mind again,” she implores. “If you wait until the ‘right time,’ you'll never do it. There is no right time. There's only now. This is your life. And you owe it to yourself to live it.”

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Femme Frugality is a personal finance writer and contributor at Invibed. She loves adventure, baseball, and naps, and hates paying full price for anything. You can learn more about her on her blog.

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