S2-EP8: Sonja O’Donnell on the Challenge of a Self-Directed Life

Jan 24, 2020


Debbie chats with a younger friend about taking a gap year sabbatical with her husband and then 13-year-old son. And how that led, a few years later, to a major life shift and an encore career, one full of possibility as well as uncertainty.



Debbie chats with a friend, Sonja O’Donnell, about the sabbatical gap year she took traveling around the world with her husband and their then 13-year-old son in tow. Both teachers, they had stepped out of highly-structured lives as long-time faculty at a prestigious secondary boarding school in Massachusetts. Their approach to a gap year was highly organized and purposeful; they were determined to make the most of an extraordinary opportunity. By chance, the O’Donnells met up with Debbie and Sam in Paris, then on their own gap year after sixty.

Several years later, they realized that the gap year had opened up new ways of thinking and they were ready for a major life shift. Sonja, now 53, talks frankly about how they continue to adjust to uncertainties as well as new possibilities. She also asks Debbie some important questions, such as “Do you find it easy to ask for help, to ask questions, to find mentors?” Debbie doesn’t answer fully on the podcast. But the answer is “No,” it’s not easy asking for help.


What they talked about:

  • The logistics of planning a traveling sabbatical with a 13-year-old in tow
  • Deliberately “unschooling” their son
  • How life was different after returning from the sabbatical
  • Planning an encore career in her early 50s
  • The challenge of creating a self-directed life
  • Highs and lows and her biggest lessons learned


Mentioned in this episode:



PHOTO: Sonja in the western provinces of China in 2013 – 2014, during her family sabbatical


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Thanks to our media partners

Encore.org, our newest media partner, is an ideas and innovation hub tapping the talent of those 50+ as a force for good. Founder and CEO Marc Freedman is an award-winning social entrepreneur and author, most recently, of How to Live Forever: The Enduring Power of Connecting the Generations. Looking for a great gap-year transition program? Check out Encore Fellowships, which match skilled, seasoned professionals with social-sector organizations in high-impact, paid assignments.


Modern Elder Academy is a program dedicated to navigating mid-life transitions. MEA, based in Baja California, Mexico, provides the place and the tools to start reframing your lifetime of experience. Grow whole, not old. Founder Chip Conley is a New York Times bestselling author, award-winning hospitality entrepreneur and a rock star of the mid-life transition movement. His newest book is Wisdom @ Work: the Making of a Modern Elder.


Next For Me is an important new resource for the 50+ crowd focused on rewriting life. Taking a gap year or timeout may be the best way to figure out "what's next" when you're in this stage of life. Founder Jeff Tidwell explains, Next For Me "connects and inspires our generation to evolve our post-50 lives through new work, a new purpose, or a new social contribution."