The Stacking Benjamins Show

How To Tell Your Boss You Want to Retire Often (SB1728)

14 snips
Aug 29, 2025
This week, negotiator and financial guru Paula Pant joins Jillian Johnsrud, author of 'Retire Often,' to discuss the benefits of mini-retirements. Jillian shares her strategies for negotiating time off without damaging workplace relationships. They explore how planning mini-retirements can enhance life satisfaction and health before full retirement. With humor and personal anecdotes, they inspire listeners to rethink traditional career timelines and advocate for living a retirement-worthy life right now.
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ANECDOTE

Author's Personal Mini-Retirement Count

  • Jillian has taken about a dozen mini-retirements herself and plans more.
  • Her experience forms the basis of her book and advice.
ADVICE

Pitch A Mini-Retirement As A Clear Story

  • Craft a simple, positive, and specific story when you ask your boss for extended time off.
  • Present it as a one-time meaningful event and offer collaborative logistics to make it work.
ADVICE

Solve Your Boss's Problems Before Asking

  • Anticipate your boss's objections and bring enacted solutions, not just problems.
  • Authorize changes (shift coverage, training) ahead of the conversation to remove friction.
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