Podcast Summary: The Stacking Benjamins Show — "You've Got Enough Money to Quit. Should You?" (SB1752)

Release Date: October 24, 2025
Hosts: Joe Saul-Sehy, OG, Doug
Panelists: Paula Pant (Afford Anything), Doc G (Jordan Grumet, Earn & Invest)
Main Theme: Rethinking Retirement — Exploring the Concept of "Reverse FIRE"

Overview

This episode delves into the idea of "Reverse FIRE" (Financial Independence, Retire Whenever), inviting listeners to consider not just retiring early, but the value and joy that can come from working longer, even after reaching financial independence. Leveraging a Wall Street Journal article about Americans who keep working past age 75, the hosts and panel discuss the social, psychological, and financial benefits and drawbacks of extending one's career by choice, not necessity. The conversation is lighthearted yet insightful, seasoned with classic SB humor.

Key Discussion Points & Insights

1. Introducing "Reverse FIRE" ([02:25])

• The crew opens by referencing the "FIRE" (Financial Independence, Retire Early) movement and various offshoots, then flips the script: What if, instead of plotting an early retirement, you choose to work longer—because you want to, not because you have to?
• Notable Quip:
  "Leave it to Stacking Benjamins that we're like, what if we do this whole thing backwards?" —Joe Saul-Sehy [02:25]

2. Why Keep Working After Financial Independence? ([09:56], [11:08])

• Purpose, Autonomy, Mastery:
  Paula Pant points to Daniel Pink's research, noting that if your work provides autonomy, mastery, and purpose, there's often no strong reason to leave. The issue for many isn’t the work itself, but the volume ("Maybe cut from 40 hours down to 20, 10, or even five" [09:56]).
• "If you can find things you love doing, that feel purposeful and happen to pay you money, there’s no hard and fast rule that says you have to retire by a certain age." —Doc G [11:08]

3. Financial and Practical Advantages of Working Longer ([12:48])

• OG breaks down the financial upside: Each added year of earning and not drawing on retirement savings makes reaching FI easier and allows more freedom in the present.
• "Just by having another five years of savings opportunity and five fewer years of drawing from your portfolio means that goal becomes so much easier to attain." —OG [12:48]
• OG humorously claims he’s aiming for age 140, just to see his kids turn 100 [14:03].

4. The Flexible Retirement Date – It’s Not All-or-Nothing ([15:04])

• The idea of "Reverse FIRE" reframes things: It’s less about retiring early and more about keeping your options open. "Remain engaged, do what you love, and work as much—or as little—as you like," summarizes the vibe.
• "Financial independence, whenever the hell you want, but remain engaged." —Joe Saul-Sehy [15:57]

5. Real-Life Examples: Redefining 'Work' in Later Life ([17:23])

• Paula shares a Wall Street Journal case study about an older photographer who "still works, but only two hours a week." The group discusses whether such minimal work still counts and agrees that rules are personal.
• "There are no rules when it comes to purpose. You just gotta enjoy what you're doing. So for some people that could be two hours, for others, forty." —Doc G [19:18]

6. Career Change & Encore Careers in Retirement ([21:00])

• Joe and the panel discuss the appeal of starting a new career at 65 or 70. Paula shares her own imagined "retirement career": founding an animal shelter [21:30].
• Doc G describes his own shift from medicine to personal finance writing and podcasting once he became FI.

7. “Second Stage” Intelligence—Older Workers’ Hidden Strength ([23:25])

• Referencing Arthur Brooks' ideas, the group notes that certain jobs become better with age due to accumulated wisdom (e.g., psychiatrist, teacher).
• "When you're older, you can synthesize between this wide... array. And that synthesis is often thought of as wisdom." —Paula Pant [24:06]

8. Potential Downsides & Unintended Consequences

A. Forgetting to Save Enough ([44:38])

• OG cautions that if you assume you’ll work forever, it’s easy to fall into the trap of under-saving, which is risky if circumstances change: "The biggest downside is the opportunity to be lazy about saving and investing." [44:38]

B. Not Exploring Other Joys or Hobbies ([48:26])

• Paula warns that habitual work can crowd out deeper exploration: "Not adequately exploring interests, hobbies, passions, curiosities outside of what conventionally be thought of as work." [48:26]

C. Loss of Flexibility & Risk of Identity Attachment ([49:19])

• Doc G notes: tying your identity and financial security to perpetual work can backfire if health, the job market, business conditions, or interests change unexpectedly.

D. Taking Up Space or Facing Ageism ([25:16])

• The panel discusses the potential challenge of ageism and whether working into advanced age limits opportunities for younger workers.

9. Work as Identity, Legacy, and Joy ([42:50], [41:21])

• Personal stories (OG’s grandfather, Doc G’s patient Eddie) illustrate how work can be a source of identity and community, but also a trap if approached reflexively.
• "He died that way. He died working, and he wouldn't have had it any other way." —Doc G [41:21]

10. The “Right” Answer Is Personal ([20:35], [19:18])

• Overarching message: There are “no rules”—the optimal path is individualized, shifting with circumstances and personality.
• "We love to have rules about how other people should live their lives. But the truth is, what do you want to do with your life?" —Doc G [19:18]

Notable Quotes & Memorable Moments

• "If you have autonomy, mastery, and purpose in your work, there’s no particular reason to leave." —Paula Pant [09:56]
• "Financial independence isn't necessarily the goal, it's just a really good tool." —Doc G [11:08]
• "By just eliminating that self-imposed number [retirement age], it's kind of a double win." —OG [14:03]
• "There are no rules when it comes to purpose. You just got to enjoy doing what you're doing." —Doc G [19:18]
• "If you've got all these things you want to do with your life, you should do do." —Doug [64:42]
• "The whole idea is to do all the stuff you want to do. If one of those things is work, then I think that's perfectly fine." —OG [16:46]
• "Whenever we decide to do something different, we have to step into the unknown. It's always emotionally easier to keep doing what you're doing." —Doc G [49:19]
• "If you can work with your boss on moving into different roles that suit you and where you can really help the company, great." —Joe Saul-Sehy [57:14]

Key Timestamps

| Timestamp | Segment/Quote | |-----------|---------------------------------------------------------------------------------------| | 02:25 | Introduction to "Reverse FIRE" | | 09:56 | Paula: Autonomy, Mastery, Purpose in work | | 11:08 | Doc G: Reframing financial independence as a tool | | 12:48 | OG: Financial benefits of prolonging work | | 14:03 | OG: "My end date is 140..." | | 15:57 | Joe: "FI, whenever the hell you want, but remain engaged." | | 17:23 | Paula: Case study of a photographer working 2 hours/week | | 19:18 | Doc G: "There are no rules when it comes to purpose." | | 21:30 | Paula: Retirement as a second career, animal shelter ambitions | | 23:25 | Reference to Arthur Brooks: jobs suited for older adults | | 24:06 | Paula: Wisdom and crystallized intelligence | | 41:21 | Doc G: Patient story of dying while doing what he loved | | 44:38 | OG: "The biggest downside is the opportunity to be lazy about saving and investing." | | 48:26 | Paula: Caution on missing out on non-work interests | | 49:19 | Doc G: The emotional challenge of leaving work | | 64:42 | Doug recaps the 3 big takeaways |

Tone & Style

As is trademark on Stacking Benjamins, the tone is witty and affable, balancing functional personal finance insights with humorous banter and pop-culture references. The panelists are generous about making space for self-exploration and counterpoints, fostering a sense of financial "permission" for listeners to design their own path.

Takeaway Action Items

1. Do what you want; there are no right rules:
   If you love working, keep working—but don’t neglect hobbies or relationships.

2. Don’t let extended career plans excuse poor saving:
   Even if you think you’ll work forever, things change—so save for flexibility.

3. Redefine what “work” looks like:
   Part-time, encore career, consulting, or shifting to roles that ignite your passion—make it your own.

4. Recognize the value of age and wisdom:
   Certain jobs and perspectives ripen with age; embrace career transitions that leverage your experience.

Closing Thoughts

The episode affirms that the “optimal” financial path is deeply personal. For some, early retirement is the dream. For others, extending work—on your own terms—can bring meaning, structure, and community. The key is designing a flexible life and financial plan that lets you pivot as your circumstances, abilities, and desires evolve.

For detailed show notes, resources, or to connect with any of the featured panelists, visit StackingBenjamins.com.

Trivia Winner:

• Paula Pant, for correctly guessing the year the U.S. Navy debuted the T-shirt: 1913. [38:17]