The Skill of Starting Over — How Deborah Hammett Built a New Life at 60

Ageless Athlete — How to Stay Strong, Curious & Capable for Life

Ageless Athlete — How to Stay Strong, Curious & Capable for Life
The Skill of Starting Over — How Deborah Hammett Built a New Life at 60
Dec 31, 2025 Season 1 Episode 107
Kush Khandelwal

“When I tell people I started sailing at sixty, they’re shocked.”

We don’t often think of our sixties as a time to begin something new—which is part of the problem.

In this New Year’s Eve episode, I sit down with Deborah Hammett, a former school principal who learned to sail at 60, moved onto a boat, and now travels solo by sea.

But this story isn’t really about sailing.

It’s about what happens when identity loosens—when long-held roles fall away, and you choose to become a beginner again, not because you have to, but because you want to feel alive.
We talk about:

  •  fear and solitude 
  •  fixing an overheating engine miles offshore with no help coming 
  •  building competence slowly 
  •  and the kind of confidence that comes from adaptation, not comfort 
This conversation explores aging not as decline, but as a long arc of learning—and asks a simple question:

👉 What would you do if the next chapter didn’t have to look like the last one?
Deborah shares life aboard a sailboat with honesty, humor, and humility—the beauty, the friction, and the lessons that come with starting over.

You can also follow Deborah on Instagram for real, unfiltered glimpses into life at sea:
 📸 @youngsaltat60

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Topics: longevity, fitness over 40, endurance training, aging athletes, recovery, injury prevention