Dawn Fleming didn’t exactly set out to live in paradise during retirement. But after enduring one of life’s most unexpected detours, she and her husband, Tom, found themselves sailing more than 5,000 miles through the Panama Canal in search of a new beginning.
“I was 50 and he was 60. We had both lost our businesses in the aftermath of the 2008 financial crash,” said Dawn. “We were completely wiped out financially. So, we jumped on our 48-foot sailboat and just started over.”
That decision not only changed the trajectory of their lives, but it eventually led Dawn to author a book titled, “Claim Your Dream Life: How to Retire in Paradise on a Shoestring Budget.”
She and Tom have lived in Mexico since 2018, where she continues to reinvent her life and inspire others to do the same. For the past three years, the couple has also spent summers in Dawn’s hometown of Minneapolis.
“I like to say I’m a recovering attorney, or better yet, an attorney turned alchemist,” Dawn explained. “This season of life is about transformation and reclaiming joy.”
Reinvention at midlife
Dawn doesn’t like the word “retirement.” In fact, she’s openly opposed to the idea.
“I believe the soul didn’t come here to retire,” she explained. “Some people harbor the idea that when you hit a certain age, you suddenly stop contributing or growing. It’s not only outdated, it’s dangerous. Without purpose, we decline mentally, physically and emotionally.”
After ending her law career, Dawn spent two decades in direct sales and network marketing. The remote nature of that work allowed her and Tom to be more mobile, eventually leading them to invest in a vacation property on Isla Mujeres.
“We had no plan to live there,” she said. “But after trying different areas of Florida and not really finding our groove, we decided to give Mexico a shot. We figured if we didn’t like it, we could always leave. Our home at the time floated. It was a big sailboat.”
What began as an experiment turned into a lifestyle that Dawn described as absolutely magical.
“It’s not just about the beaches and weather. It’s the culture,” she explained. “In Mexico, elders are honored. They are seen as wise, essential and valuable. That’s something I wish more older Americans could experience.”
Claiming a dream life
Moving abroad opened Dawn’s eyes to how affordable and fulfilling life can be when people embrace simplicity and intentionality.
“It’s shocking how many myths people believe about retiring overseas,” she said. “They think it’s too expensive or unsafe, or that they’ll lose access to healthcare. But for us, it’s been the opposite.
“I pay $155 a month for global insurance with evacuation coverage,” she added. “And the quality of care here is phenomenal.”
Dawn has also discovered the joy of living in a community that values relationships over hustle. Whether it’s walking to the local market, chatting with neighbors, or enjoying sunsets from her oceanfront patio, she has found a rhythm that nourishes her soul.
Her book offers a practical roadmap for others who want to explore retirement in a different light. It combines personal stories, financial insights and real-world strategies for designing a life that fits your dreams and your budget.
But more importantly, it challenges readers to rethink the entire concept of retirement.
“In the book, I explain that paradise isn’t a place, rather it’s a mindset,” Dawn said. “You can’t just move somewhere and expect all your problems to go away. You have to do the internal work. You have to decide what lights you up, and what motivates you to get out of bed in the morning.”
A message of longevity and purpose
Dawn believes the way people think about aging has a direct impact on how they age. One study she referenced in her YouTube channel showed that individuals with a positive perspective on aging live an average of seven years longer.
“That’s huge,” she said. “If we expect decline, that’s what we’ll get. But if we embrace the possibility of thriving, even into our eighties, nineties or beyond, then we give ourselves a chance at not just a longer life, but a more meaningful one, too.”
Dawn recently launched a YouTube channel called “Midlife in Paradise,” where she dives deeper into topics like longevity, reinvention and living fully after turning 50.
Drawing from her own experience and extensive research, Dawn offers content that is inspiring as well as highly practical.
“I launched the channel because I saw a gap,” she said. “There’s plenty of financial planning advice for retirement, but almost nothing on the emotional and psychological aspects, like identity, meaning and purpose. That’s what people are hungry for.”
Her next book, tentatively titled “Retire Rich: How to Turn Your Golden Years into Your Boldest Years,” is already in development. The goal is to help readers stop obsessing over nest eggs and start living courageously.
“Even people who have money often struggle in retirement,” she said. “Without purpose, it’s easy to fall into a rut. Wake up, watch TV, scroll through social media and then go to bed. That’s not a dream life. That’s just passing time.”
Living until the day you die
For Dawn, meaning and purpose come from living fully, not just existing. That’s why she encourages people over 50 to get out of their comfort zones, try new things and give themselves permission to start over.
“We’re not done yet,” she insisted. “Our cells have the ability to regenerate up to age 120 or more. What if our lifespan really is that long? Are you going to stop living at 60 or 65? That’s not even halfway.”
She also stressed the importance of aligning your life with your deepest interests and values.
“Just because you’re good at something doesn’t mean that’s what you should do,” she said. “Law was a skill set for me, but not a passion. My soul wanted something different and I had to listen to what it was telling me.”
Today, Dawn and Tom continue to sail, explore, host guests at their boutique hotel, and serve as examples of what is possible when people dare to reimagine their futures.
“If you’re unhappy where you are, moving won’t fix it,” she explained. “But, if you’re ready to take responsibility for creating the life you want, regardless of where you live, then amazing things can happen.”
Her advice for people over 50 is to focus on health, not illness. Focus on living, not retiring. And find something that excites you so much that you can’t wait to get out of bed.
“Living your dream life isn’t about escaping,” she added. “It’s about choosing joy every single day.”
For more information
People can connect with Dawn in several ways, including:
- Website = www.claimyourdreamlifebook.com
- Facebook = www.facebook.com/dawndfleming
- Instagram = www.instagram.com/midlifeinparadise
- LinkedIn = www.linkedin.com/in/dawnfleming
- YouTube = www.youtube.com/@midlifeinparadise
Dawn’s book, “Claim Your Dream Life: How to Retire in Paradise on a Shoestring Budget,” is available on Amazon and in other bookstores. If you follow her on Amazon, you will be alerted when her next book, “Retire Rich: How to Turn Your Golden Years into Your Boldest Years,” is released.
If you order a copy of Dawn’s book from a link above, Forward From 50 may receive a small commission at no extra cost to you.
After closing his business and enduring several painful years of uncertainty regarding what to do with his life, Greg founded Forward From 50 to help men and women over 50 to live more purposeful lives by pursuing things they are passionate about. A Wisconsin native, Greg currently lives in Arizona.