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

The Stacking Benjamins Show

Why wait until your knees creak louder than your rocking chair to start enjoying life? In this episode, Joe Saul-Sehy, OG, Paula Pant (AffordAnything) and Neighbor Doug welcome Jillian Johnsrud—author of Retire Often—to share why sprinkling your life with mini-retirements might be the smartest, healthiest, and most joyful move you make before your “official” retirement date. Think of it as giving your future self a head start… without the Medicare paperwork.

From negotiating time off without burning bridges, to building a financial plan that lets you step away without panic, Jillian offers a roadmap to hit pause on your career without pressing stop. We explore the balance between health, capability, and the freedom to explore, and how to sell the idea of a mini-retirement to your boss so they don’t see it as a resignation letter in disguise. And because it’s the basement, we also mix in some Labor Day trivia, a few personal experiments with unconventional choices, and just enough playful banter to keep you leaning in.

If you’ve ever felt the grind wearing you down but can’t picture walking away forever, this episode will help you reimagine your work-life timeline. Mini-retirements aren’t just for the wealthy or the whimsical—they’re for anyone ready to start living a retirement-worthy life now.

• How to pitch a mini-retirement to your boss without triggering an awkward HR meeting

• The financial prep work that makes time off less stressful and more satisfying

• Ways to test-drive retirement before the “official” date

• How to handle the skeptics (at work and at home) who think you’re making a mistake

• Why health and capability should be part of your retirement timing equation

  Questions to Ponder While You Listen

• If you could take 3–6 months off tomorrow, how would you spend it?

• Would a series of shorter retirements feel more fulfilling than one long one at the end?

• What’s the biggest barrier—financial or otherwise—keeping you from taking a break?

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