99. Young Salt at 60: Deborah Hammett on Reinvention, Resilience, and the Freedom of the Sea

Redefining Retirement, One Wave at a Time
In this episode of What’s the Point?, Bill Ellis welcomes Deborah Hammett, retired educator turned solo sailor and author of Young Salt at 60. After a 30+ year career as an elementary school teacher and principal on Martha’s Vineyard, Deborah did something few would expect—she learned to sail at age 60 and now lives aboard her boat, Maia, navigating the East Coast and The Bahamas.

Deborah’s story is about more than sailing—it’s about reinvention, lifelong learning, and answering the question: what’s next? From her early dreams of changing society through education to navigating the open ocean with no prior experience, Deborah exemplifies the power of purpose-driven pivots later in life.

Episode Highlights & Key Takeaways:

• From Classroom to Cockpit: How Deborah transitioned from public education to full-time sailing.
• Tears Are Not a Strategy: Lessons in resilience she passed on to students—and learned herself.
• Raising Kids and Building Community: Why Martha’s Vineyard became her home and launching point.
• Learning to Sail at 60: The hilarious and humbling early days of flipping lasers and falling in the marina.
• Solo Sailing as a Lifestyle: How she learned to manage a 36-foot keelboat and navigate weather, tides, and repairs.
• Mechanical Mastery: From bilge pumps to solar panels—how Deborah learned the technical side of boat life.
• Unlearning Bias: Facing internal biases and gender assumptions as a female captain.
• What’s the Point of Retirement?: Why Deborah believes your post-career years can hold just as much growth—and adventure—as the decades before.

 

Connect with Bill:

• [e-mail]
• www.brandingpillars.com
• www.brandingforresults.com
• IG - @wcellis
• Facebook - @CoachBillEllis
• LinkedIn - linkedin.com/in/wcellis
• Book: Women Who Won

Links for This Episode:

• Book: Young Salt at 60 (available wherever books are sold)

Quick Episode Summary: 

• 0:00 Welcome and intro to Deborah Hammett’s unique journey
• 1:00 What inspired her to take up sailing at 60
• 3:00 Reflecting on three decades as a teacher and principal
• 6:00 Life on Martha’s Vineyard and how the ocean called to her
• 10:00 Family, independence, and growing up with grit
• 12:00 Teaching kids confidence, curiosity, and how to fail forward
• 14:00 Challenges with the teacher’s union and burnout at the end of her career
• 18:00 “Believe in Yourself”: The message her former students still remember
• 20:00 Life after retirement—travel, divorce, and the courage to start over
• 24:00 Discovering sailing and falling (literally) into a new life on the water
• 29:00 Buying Maia, learning the ropes, and sailing solo
• 32:00 Navigating weather windows and the unpredictability of boat life
• 34:00 Writing Young Salt at 60 to inspire others to take bold steps
• 35:00 Why staying active and learning new things keeps you young
• 38:00 The steepest learning curve: understanding mechanics and repairs
• 41:00 Self-discovery through travel—and confronting her own biases
• 43:00 Her answer to “What’s the Point?”: Use your post-career years for something big

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