Sailing Solo, Spiritual Growth, and the Journey to Authorship with Deborah Hammett
In this episode of Authors Who Lead, I sit down with Deborah Hammett, author of Salty at 60: Becoming Better Than Retired. Deborah’s story is the bold, honest tale of how she left her thirty-three-year career in education in pursuit of a freer, purpose-filled second act—sailing solo aboard her boat and, eventually, writing a book about her experience.
For many, the notion of retirement conjures thoughts of rest, perhaps a bit of travel, and a well-deserved break from decades of hard work. Deborah’s experience, however, flips the script: “What’s the point of retiring if you’re not going to do anything with that time?” she challenges. Instead of seeing retirement as an ending, Deborah saw it as the launch pad to redefine herself entirely.
The Call of Freedom—and Its Lessons
The transition from her structured days as a teacher and principal to the boundless seas was not immediate or easy. Deborah first tried online teaching, becoming a digital nomad teaching English to elite students across the world from Thailand, Malaysia, and the Dominican Republic. The pandemic, rather than curtailing her explorations, opened up quiet, uncrowded destinations and afforded her adventure and introspection.
Sailing, however, was something new and intimidating. Despite years of living on Martha’s Vineyard, sailing was not a skill she had developed. Inspired by her partner and a desire for self-determination, Deborah learned to sail on Lake Champlain and quickly became enamored with living aboard. The lessons came fast and hard, particularly when she decided to single-handedly navigate her boat thousands of miles down the eastern US and into the Bahamas.
Living on a sailboat brought a new definition of freedom—a flexible lifestyle with unpredictable rhythms governed only by the weather and her own choices. The uncertainty was both exhilarating and humbling. “With freedom comes a new sense of letting go,” she reflects. “I need to be present so I can make good, clear, conscious decisions… I make mistakes when I am three steps ahead of where I am.”
Becoming the Student Again
A former educator, Deborah found herself on the other side of the classroom: a rookie sailor, sometimes lost, often frustrated, and always learning. “I’ve had to be my worst student,” she admits, coping with mistakes and the humility of asking for help. Yet, with every misstep—whether changing her oil or calling a bridge tender—her competence, confidence, and community grew.
Perhaps the most potent lessons came from her interactions with the people she met along the way—many of whom surprised her by shattering her anticipations and biases. “My spirituality has been tested big time,” she shares, recalling moments of vulnerability at sea and the kindnesses of strangers she might have overlooked or feared in her former life.
Finding Purpose Beyond the Classroom
Despite the excitement, Deborah felt the emptiness that comes from losing one’s sense of purpose. She reflected, “I had always wanted to be making a difference for somebody somehow … and here I was just selfishly floating around in my sailboat without an ethical anchor.” That void became the genesis for her book.
Writing became her new way of teaching—using storytelling to empower and inspire other “mature adults” to take risks, learn something new, and push beyond comfortable limits. The process was, surprisingly, effortless; the stories of adventure, vulnerability, and growth “wrote themselves” on rainy days aboard her boat.
Sharing the Adventure
Publishing, however, was foreign territory: Deborah navigated the world of editors, cover designers, and book marketing, discovering a brand-new version of learning and humility. Yet, she continues to find joy in sharing sailing “hacks” and sunrise vistas on social media, determined to be an “influencer” on her own terms.
Her message for those hesitant to start late? Retirement, or any new beginning, isn’t the end. If you’re willing to relinquish a little control and embrace the chaos, a richer, more authentic life awaits. As I observe, true freedom is found not in certainty, but in permanently flexible presence.
Final Thoughts
Deborah Hammett’s journey is a testament to the power of reinvention—proof that life’s greatest growth often comes when you dare to become a beginner again. Her story, both in Salty at 60 and beyond, encourages us all to unmoor from expectations, seize adventure, and write the next chapter on our own terms.
Join us again next week for more captivating insights from influential authors and publishing experts. Remember to subscribe to Authors Who Lead and visit our website for more show notes and past interviews.
That’s all for this week. If you have a message inside of you that needs to be written, today is the day to start. Don’t delay—take action.
Episode Resources
Connect with Deborah here:
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Young Salt at Sixty
Get a copy of Deborah’s book here:
Salty at 60: Becoming Better Than Retired
