From Foreclosures to a Caribbean Dream: How Dawn Fleming Redefined Retirement and Built a Life of Purpose

Have you ever faced a moment in life so challenging that it shook the very foundation of your future? What if, instead of breaking you, that moment became the launching pad to your wildest dreams? That’s exactly what happened to Dawn Fleming, a woman who has lived, lost, rebuilt, and reimagined what it means to truly live — all after the age of 50. In this episode of Living Ageless and Bold, Christina Daves sits down with Dawn to discuss how she went from having three houses in foreclosure to owning a boutique hotel on a Caribbean island. Her story is one of courage, resilience, creativity, and radical reinvention.

This blog dives into the rich, detailed, and deeply personal conversation between Christina and Dawn — sharing Dawn’s life lessons, and how she’s now helping others redefine retirement and rediscover paradise.

Dawn’s Origin Story: The “Badass by Necessity”

Dawn jokes that she became a “badass by necessity,” a title earned through a combination of hard-won wisdom, relentless determination, and sheer grit. Her journey begins in middle age, after navigating significant life upheavals. As she puts it, “We had everything, we lost everything, we built it back up, we lost it again, and built it back up.” Her words are not just a summary of her financial history, but a battle cry for anyone who thinks it’s too late to start over.

A former attorney and entrepreneur, Dawn’s life was far from easy. She and her husband faced financial devastation with three homes in foreclosure. It was a humbling and deeply painful period — one that made it seem impossible to dream, let alone rebuild. But that’s where the seeds of her transformation were planted.

The Rise, The Fall, and The Caribbean Comeback

Dawn Fleming and her husband Tom were once successful real estate investors, managing 11 properties. But like many, they were hit hard by the 2008 housing crash. In the span of just a few years, they lost everything—three houses went into foreclosure. The couple, who were used to a life of financial stability, found themselves on the other side of the economic equation.

Instead of letting the loss define them, they chose to rewrite the story.

“We made the conscious decision that we were going to live the rest of our lives in alignment with our values,” Dawn shared. For them, that meant freedom, connection, travel, and new experiences.

Building a Dream from the Ground Up

With their priorities realigned, Dawn and Tom set their sights on something completely new—building a boutique hotel in Mexico. It wasn’t just a pipe dream. Dawn and Tom bought a three-bedroom house on Isla Mujeres, an island just off the coast of Cancun, and turned it into a stunning four-apartment boutique hotel. They lived on the third floor while renting out the first two.

“We saw the potential,” Dawn explained. And it wasn’t long before they saw the returns. They realized the financial benefit of converting it from a four-bedroom to a six-bedroom rental and made the shift. However, living on an island with 25,000 to 30,000 daily visitors and limited access to big box stores like Costco and Home Depot eventually took its toll.

In 2023, they retired from in-keeping after five successful years and handed over the reins to a local property manager. Dawn now manages bookings remotely, allowing them more freedom as they plan their next big adventure: building an organic farm with an eco-tourism retreat and event center.

Turning Conversations Into a Calling

Interestingly, Dawn’s next venture was born from casual beach conversations. Her husband, a natural extrovert, would chat up tourists who were amazed to learn the couple owned property in Mexico.

“Can you even do that?” they’d ask.

After hearing the same questions over and over again, Dawn realized there was a genuine need for guidance. So she created a free workshop called How to Live in Paradise Without Worrying About the Price Tag. It struck a chord, especially during the pandemic when people were reevaluating their lives. This workshop eventually became the basis for her book.

“People are craving a different way of living,” Dawn said. “They just don’t know where to start.”

A Workshop That Changed Lives

The impact of Dawn’s workshop went far beyond real estate advice. Her teachings opened doors for real transformation.

One of the most touching stories came from a Canadian man in his late 60s who sent Dawn a deeply emotional email after attending her workshop. “You have taken me from the winter of my life to the spring of my life,” he wrote. He followed Dawn’s advice to do a 30-day beta test—living like a local before making a big move. During his stay, he met Diane, and the two fell in love. A few months later, he returned with an engagement ring. They’ve been married ever since.

Another couple who met through the program even asked Dawn and Tom to be witnesses at their wedding.

These stories reflect Dawn’s true impact: helping people reconnect with joy, possibility, and a sense of purpose at any age.

Redefining Retirement: Midlife Is Just the Beginning

Now in her 60s, Dawn is on a mission to redefine what retirement looks like. “The soul did not come here to retire,” she declares, challenging the outdated notion that life ends at 60.

“If your quality of life can extend into your 100s, why are you planning to retire at 60?” she asks. “That’s not the end of life. That’s middle age.”

She emphasizes the importance of inner work — the kind that helps people clarify what they really want in their next chapter. Her new coaching and consulting services are designed for professionals with complex lives: the attorneys, engineers, and entrepreneurs who can’t just pick up and move but feel deeply unfulfilled by their current lifestyle.

“We’re not digital nomads,” she explains. “We’ve got real estate, businesses, and cars. I help people figure out what they really want the end result to look like.”

For Dawn, the concept of paradise isn’t just a place — it’s a mindset. “Wherever you go, there you are,” she reminds listeners. If you’re not happy in your current life, you probably won’t be happy on a beach in Mexico either. Her work now focuses on helping people align their internal lives with the external dream.

Ageless Living: Breaking Through the Limiting Beliefs

Dawn is also a passionate advocate for ageless living. “Sixty is middle-aged,” she laughs. “If science says our cells can regenerate to 120 or 150, why retire at 60? What are you going to do for the next half of your life?”

This isn’t just rhetoric — she lives it. Her 84-year-old mother still cares for a woman about to turn 100. At her mother’s 80th birthday party, Dawn’s brother remarked that their mom seemed no different than she did at 60. It’s proof that age is just a number, and attitude is everything.

Dawn doesn’t believe in buying into the societal script that says we’re “too old” to do something new. In fact, she says she’ll playfully (and sometimes literally) smack her husband when he says “I’m old.” It’s a mindset she refuses to accept — and encourages others to reject as well.

Dawn’s Advice to Her 30-Year-Old Self

When asked what advice she’d give her 30-year-old self, Dawn doesn’t hesitate. “Listen to your inner wisdom,” she says. “Trust that voice, that gut feeling, and care less about what people think.”

This isn’t just a cliché. It’s advice born from decades of real life — the kind that humbles, stretches, and shapes you. It’s clear that for Dawn, tuning into that internal compass is what allowed her to navigate the highs and lows of her unconventional journey.

She reflects on how much time people waste worrying about how they’re perceived, especially when they’re younger. Now, with the clarity that comes from experience, she realizes how little that external noise matters. That inner knowing — the quiet nudge, the gut instinct — has always been there. The challenge is learning to listen to it sooner.

Dawn’s words are a permission slip to stop performing, stop second-guessing, and start trusting yourself. Her advice is especially poignant for anyone who’s felt stuck, lost, or unsure: you already know what to do. You don’t need more credentials or approval. Just trust that small voice inside — it knows the way.

Final Thoughts: What Could Be Your Next Chapter?

Dawn Fleming didn’t just change her life; she created a blueprint for others to follow. Her journey reminds us that setbacks are setups, that reinvention is always possible, and that joy is something you can design. Dawn’s story is more than inspiring — it’s a blueprint. A reminder that it’s never too late to start over, that loss can be a teacher, and that paradise begins with a mindset shift.

Whether you’re dreaming of living abroad, starting a new business, or just craving more purpose in midlife; Whether you’re in your 30s, 50s, or 70s, you have the power to redefine your life. You don’t need a million dollars. You don’t need everything figured out. What you need is courage, clarity, and the willingness to dream — again and again.

Let Dawn’s story be your spark.

Because paradise isn’t a place. It’s a mindset.

And your next chapter? It could be the best one yet.

As Dawn so powerfully put it, “The cool thing about dreams is you get to dream a dream, make it come true, and then you get to dream another dream.”

So, what’s your next dream?

Watch her full episode here: