The Midlife Chrysalis
The Midlife Chrysalis

Surfing at 87, Writing at 91: James Flaherty’s Rules for Life

September 14, 2026

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5 min read

Surfing at 87, Writing at 91: James Flaherty’s Rules for Life

James Flaherty arrived at his first Modern Elder Academy workshop at age 87, read Chip Conley’s blog for two years before that, and went surfing in Baja because someone asked him to. “I said, fine, I’ll do it, but then I never have to do it again.” Now 91, Flaherty has attended seven MEA workshops, written five books in his eighties, and has a screenplay called Old News currently optioned by a Hollywood production company. The premise: a failing cable news channel hires four retired newscasters aged 75 to 90. “Welcome to the evening news,” the lead anchor says in the script. “We’re old enough to know better.”

The Long View of a Life

Born in Coral Gables, Florida in 1935, before air conditioning and sunblock, Flaherty grew up playing in the Florida sun and now has “every skin cancer you can possibly imagine.” His father, the district attorney of Miami, died at 47 leaving the family with nothing. Flaherty was 14. He doesn’t remember it being hard. His mother was brilliant, and he got through college on a bassoon scholarship—the only person he knows who finished college that way. He played clarinet, cello, and bassoon. “When was the last time you picked up a bassoon?” Conley asks. “The day I got out of college.”

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What you'll learn

  • 1 (00:00) **Opening Wisdom: The Source of Strength** - Jim Flaherty introduces his core belief that strength comes from responding to the wisdom, love, and needs of other people.
  • 2 (01:09) **Meet Jim Flaherty: The 91-Year-Old MEA Regular** - Chip Conley introduces Jim as a seven-time MEA workshop attendee who first came at age 87, full of "lived wisdom and funny wisdom."
  • 3 (02:35) **How a Blog Led to a Life-Changing Workshop** - Jim explains he read Chip's blog "Wisdom Well" for two years before booking his first workshop, which turned out to be a magical week with Dan Buettner of Blue Zones.
  • 4 (03:50) **Surfing at 87: The Irreverent Oldest Guy in the Room** - Jim recounts his surfing experience at the workshop and explains why he never feels like the oldest person in the room.
  • 5 (04:50) **Five Books in His 80s and a Screenplay Called "Old News"** - Jim shares his prolific creative output, including five books and a screenplay that has been optioned by a Hollywood writer.
  • 6 (07:05) **A 91-Year-Old Origin Story: From Coral Gables to Madison Avenue** - Jim describes his childhood in pre-air-conditioned Coral Gables, his father's sudden death at 47, and his journey to New York via a full-tuition bassoon scholarship to Michigan State.
  • 7 (09:55) **The Argentina Chapter: A Career and a Family Abroad** - Jim recounts accepting a job with J. Walter Thompson in Buenos Aires, moving his family 5,400 miles, and becoming a creative director for major global accounts.

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Guests on this episode

Chip Conley

Show Notes

At 91, James Flaherty isn’t slowing down. He’s still writing, creating, learning, and planning what comes next.


A former advertising executive, entrepreneur, innkeeper, and author who wrote five books in his 80s, James joins Chip Conley to share what nine decades of living have taught him about aging well and staying fully engaged with life.


In this episode, James shares:

  • Stay useful, not youthful. Growing older brings experience and wisdom that can be put to work for others.
  • Always have a reason to wake up. Purpose, goals, and new projects keep life moving forward at every age.
  • Never stop learning. Curiosity opens new doors and gives you opportunities to keep growing and discovering new parts of yourself.
  • Stay connected. Community, friendship, and being present for others become even more important as we age.
  • Help someone today. Small acts of kindness and service can make someone else’s life better while giving greater meaning to your own.


Watch the full episode for an inspiring perspective on longevity, purpose, and making every stage of life count.


Timestamps:

(00:00) Meet James Flaherty

(03:06) Writing Five Books in His 80s

(05:21) James’ Early Life and Career

(08:20) Moving to Argentina

(10:30) A 47-Year Partnership

(15:36) Caring for a Partner With Dementia

(18:37) What Gets Better With Age

(21:16) The Wisdom That Comes With Age

(23:33) James’ Longevity Recipe

(26:57) How to Find Your Purpose

(28:39) Four Pathways to Purpose

(33:45) Advice for Younger Generations

(34:39) Help Someone Today

(38:12) What James Still Wants to Do


Learn more about MEA at ⁠https://www.meawisdom.com/


#HealthyAging #Longevity #Purpose #AgingWell #ActiveAging #Midlife #LifeAfter50 #PositiveAging #HealthyLongevity #PersonalGrowth #Wisdom #FindingPurpose #SuccessfulAging #JamesFlaherty #ChipConley

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