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

14 snips

Aug 29, 2025

Guest

Jillian Johnsrud

Guest

Paula Pant

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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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.

ADVICE

Create Financial And Operational Runway

Build operational and financial runway before you step away so things don't break while you're gone.
Automate bills, arrange pet/home care, and plan contingencies well ahead of departure.

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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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