The Midlife Chrysalis Surfing at 87, Writing at 91: James Flaherty’s Rules for Life
Sep 14, 2026
James Flaherty, a 91-year-old author, entrepreneur, and former advertising executive, reflects on a life shaped by creativity, love, caregiving, and reinvention. He shares stories of surfing at 87, writing five books in his eighties, building a country inn, and planning his next decade. The conversation explores aging, purpose, curiosity, connection, and staying useful at every stage of life.
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A Bassoon Scholarship Opened James Flaherty’s Future
- James Flaherty lost his father at 14 but reached college through his mother’s support and a bassoon scholarship.
- He studied communications at Michigan State, one of only two U.S. schools offering the degree in 1957.
A One-Year Trial Became A 47-Year Partnership
- After separating from his wife, James Flaherty built a 47-year partnership with Bob after agreeing to try living together for one year.
- Their complementary talents helped them create businesses, including a restored country-house inn.
Plan Early For Aging And Caregiving
- Treat caregiving as a demanding 24/7 role and plan support before a parent or partner becomes isolated.
- James Flaherty hired a live-in caregiver at 64; Esther remained with him for 27 years.
