Podcast Summary: The Stacking Benjamins Show

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

Release Date: August 29, 2025
Hosts: Joe Saul-Sehy, OG, Doug
Guests: Jillian Johnsrud (author, "Retire Often"), Paula Pant (Afford Anything)

Episode Overview

This lively Labor Day weekend episode explores the unconventional idea of taking "mini retirements" throughout your career, not just at the end. Joe, OG, Paula, and guest Jillian Johnsrud discuss how and why to step away from work periodically, how to pitch it to your boss (especially if you’re not self-employed), the financial and personal planning involved, and the broader benefits of practicing retirement before making it permanent. The conversation is peppered with personal anecdotes, strategies, and the show’s trademark humor.

Key Discussion Points & Insights

1. What Is "Retiring Often"?

• Jillian Johnsrud has taken 12 mini-retirements over her life and recently authored a book on the topic.
• "It's something that feels a little impossible or a little crazy or weird. And then once it's explained, people are like, oh, I mean, I guess I could do that. And it's also life changing." (Jillian, 05:35)

Definition:

• A "mini retirement" is described as taking a break of a month or more from your job to focus on something meaningful outside of work.
• It can happen between jobs or as a negotiated leave with your employer.

2. How to Pitch a Mini-Retirement to Your Boss

The Four Elements of a Successful Pitch (Jillian, 09:55)

• Be Positive: Focus on aspirations, not burnout.
• Make It Interesting & Specific: Tie it to a meaningful, concrete event or goal.
• Frame as a One-Time Event: Present it as unique to reduce pushback.
• Bring Solutions, Not Problems: Come prepared with how your absence will be managed.

“It all has to be true. But it can't be the whole truth because the whole truth is too big... keep it real simple, but use those four things.” (Jillian, 10:02)

Example Pitch:

"My parents always planned to take a bike trip through Croatia at 60. My dad passed away, and my mom is turning 60. I'd like to do this with her, but I need extra time off. Here’s a plan for how my work will be covered." (paraphrased, 10:49)

Paula’s Tactical Tips:

• Anticipate and address all your boss’s pain points; where possible, enact solutions in advance.
• If you're replaceable, try to arrange coverage with colleagues. If you’re not, propose ways to cross-train staff or document procedures. (12:09)

"You don't ever want to bring them a problem. You want to bring them solutions." (Paula, 12:09)

Acknowledging Obstacles:

Jillian recommends naming the tough issues up front to disarm objections and open collaborative dialogue. (13:18)

3. Planning—Financial and Logistical Preparation

OG’s Advice:

• Don’t surprise yourself any more than your boss; prepare your finances and logistics months in advance.
• Consider automating bills, covering all responsibilities at home, and understanding how unpaid time will affect your budget. (14:33–16:58)
• “What are the things that might break if I don’t pay attention to them?” (OG, 16:23)

Runway Required:

• If a mini-retirement is just a month and you have a job to return to, your regular budget with some savings should suffice.
• Quitting for a year? Plan for at least a year’s expenses, plus 6–8 months’ runway to find another job. (Jillian, 17:04)

Timing Your Ask:

• Generally, ask your boss 3–4 months in advance; 12 months is too early in most office cultures. (18:02)

4. Practicing Retirement—Why It Matters

The Flaw of Saving It All for Age 65

• Many people discover, too late, that they dislike the “retirement” they dreamed about.
• Jillian and Paula liken practicing retirement to dating before marrying; you need a test run to know if it suits you. (19:15–22:11)
• “Retirement is a skill, and like any skill, it requires practice.” (Paula, 20:39–20:42)

"Spread out the disappointments. Don’t feel all the disappointments at once at 65—pace them out throughout your life, every mini retirement." (Jillian, 22:11)

Flexibility & Course Correcting

• Plans change due to life events (health, markets, family needs).
• OG: “The action of actually planning is the thing. The conversations ...are the thing that’s most important.” (22:59)
• Embrace mini retirements as small experiments—test and adjust as you go.

5. Is the Trend of Retiring Often Growing?

• Sabbaticals are twice as common as a few years ago (though statistics admitted to on-air improvising!) (25:42).
• Especially for workers in their 20s and 30s, job changes are more frequent, often leading to natural career pauses.
• The old model of one job and a late-life retirement no longer fits many people; mini retirements in between jobs are more attainable and can prevent the “big retirement” letdown. (Jillian, 26:02)

6. Overcoming Limiting Beliefs

• Don’t fall for the false dichotomy that you can either work endlessly or retire forever—you can do both, in cycles.
• Paula: “Most of us as children, we are taught a very, very linear, specific way to live our lives... But ultimately, if there’s something ...you’re truly committed to doing, you can always find a way to make it happen.” (32:32–33:27)
• Reframe “I can’t” into “I choose not to,” which puts the control back in your hands. (Paula, 33:54)

7. Navigating Trade-Offs and Memory-Making

• Jillian suggests that while big “epic” mini-retirements can be exhilarating, multiple smaller ones with loved ones build cherished memories over time. (51:38)

“The cool thing feels cooler initially and the little things with people you love gain more traction as you age in your memory.” (Jillian, 52:27)

• Paula references “nostalgia bias”—cherished memories grow rosier over the years, whether from many small trips or one big one (53:45).

8. Health, Capability, and Timing Your Dreams

Jillian’s 4 Health Quadrants (45:03–46:24)

• Life is not just about money—physical capability, preferences, and priorities change over time.
• Don’t defer high-physicality goals (like hiking a long trail) to after age 65, since the average “healthy life expectancy” in the U.S. is just 66.

“If you feel regret about that, feel it now where you have the ability to change your mind..." (Jillian, 46:42)

Paula adds: Our lifelong interests and abilities shift. What you treasure at one age may not matter (or be possible) later. Look for themes in what’s always brought you joy. (49:03)

Notable Quotes & Memorable Moments

• "Retirement is a skill, and like any skill, it requires practice."
  — Paula Pant (20:42)
• "It all has to be true, but it can't be the whole truth... If you try to tell the whole truth, you'll lose the plot."
  — Jillian Johnsrud (10:02)
• "Spread out the disappointment. Don’t feel all the disappointments at once at 65—pace them out…the same way with mini retirements."
  — Jillian Johnsrud (22:11)
• "The action of actually planning is the thing... because anybody who retires right now...in five years from now, they're gonna go, 'Well, that didn't happen.'"
  — OG (22:59)
• "Rephrase 'I can't' as 'I choose not to.' ...There's such a difference between saying I can't versus I choose not to."
  — Paula Pant (33:54)
• "You're going to show up to that retirement party whether you're dressed for it or not."
  — OG (30:12)

Timestamps for Important Segments

• 05:35 — Jillian introduces the concept of "retiring often" and her book.
• 09:55 — How to pitch a mini-retirement to your boss (Jillian’s four elements).
• 12:09 — Paula’s tactical negotiation strategies.
• 14:33 — OG on the importance of planning and “runway.”
• 17:04 — How much financial buffer is enough? Jillian defines mini-retirement.
• 19:15 — Problems with waiting until age 65 and the importance of rehearsing retirement.
• 22:11 — The value of spreading out life’s disappointments and learning from mini-retirements.
• 25:42 — Mini-retirements: trend or wishful thinking?
• 32:32 — Overcoming limiting cultural beliefs and the false dichotomy.
• 45:03 — The four health quadrants: capability, costs, and aging.
• 51:38 — Should you save for one big dream or pursue multiple smaller ones?
• 55:16 — The anticipation of mini-retirements is itself rewarding.

Light-Hearted & Engaging Moments

• OG and Doug’s banter about retirement party dress codes and advanced ages.
• The playful trivia segment on the real cost of labor and delivery in the U.S. (winner: Jillian with her close guess, 43:32).
• Frequent audience interaction and jokes about running, camping, and old school vs. modern “sabbatical” culture.

Resources & Next Steps

• Jillian Johnsrud’s Book: Retire Often – available everywhere books are sold.
• Podcast Connections:
  • Paula Pant’s Afford Anything podcast
  • Stacking Benjamins YouTube channel (catch the team live on Mondays)
• Financial Planning: OG offers personalized help via stackingbenjamins.com/often

Takeaways

• Mini-retirements are possible for regular employees, not just entrepreneurs.
• Planning, pitching, and practicing retirement skills will make your future full retirement far more successful—and less risky.
• Embrace both small and large breaks; memories, flexibility, and health don’t last forever.
• Challenge linear life scripts—retire (even briefly) before you actually retire!

"Make your life a science experiment! Retire often, learn as you go, and enjoy the journey—not just the destination." (paraphrased from Jillian, 27:45)