#187 - Reinvention: Why it’s never too late to change, credentials don’t matter, and there are no small moments

Jay Sargeant has never had a job.

At 79, he is building his eighth working life. Before that he was a community organizer, a tennis professional, a franchise developer, an NLP training consultant, the builder of a distributor network, and, starting at 72, a pickleball coach. He started most of those with no credential, no background, and no backup plan.

In this conversation Jay tells Ryan how he became a tennis pro before he ever hit a tennis ball, how he walked into the office of one of the biggest names in franchising with no resume and left with the job, and what a stranger at a Marina del Rey swimming pool handed him that redirected the next decade of his life.

He also names the three things he believes hold people back: credentials are overrated, there are no small moments, and it is never too late to change. The last one he learned from his grandmother, who found a second great love at 94.

If you are competent, respected, and quietly finished with what you are doing, this one is worth an hour.

What you will hear

  • Why Jay will help you rebuild your house for free but cannot be told to show up at seven
  • The five-person question he asked when he wanted out of tennis, and the answer all five gave
  • The blue suit, the briefcase he never opened, and the meeting with no resume
  • Graduating 326th out of 327 at Boston Latin, and what six years of excuses actually taught him
  • The stranger at the pool, Frogs into Princes, and eleven pages that changed his career
  • The 90-year-old with a $1,000 annual growth budget
  • Why he walked away from a business he was winning at, more than once

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