The Case Against Early Retirement (SB1638) | The Stacking Benjamins Show Video

Ever dreamt of quitting your job early and sipping piña coladas on a beach? Before you tell your boss what to do with that job and start booking your one-way ticket to paradise, today’s roundtable might make you think twice. Join Jesse Cramer from The Best Interest, Paula Pant from Afford Anything, and our own OG as they break down the case against early retirement. The gang’s here to challenge the “quit work, retire early” dream and explore whether it’s really as awesome as it sounds—or if there are a few catches you haven’t considered.

The conversation gets into the nitty-gritty of why early retirement might not be the smooth ride some people think it is. From the psychological toll of too much free time to the unexpected financial hurdles, our panelists share the real stories behind the headlines. What’s the balance between financial freedom and a fulfilling life? Can you really retire early without regret, or does the cost of quitting work too soon outweigh the benefits?

And don’t forget about Doug’s wicked trivia challenge!

FULL SHOW NOTES: link

Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at link

Enjoy!

0:00:00 - Intro
0:0:45 - 1st Half
0:28:52 - Doug’s Trivia
0:37:55 - 2nd Half
0:54:54 - What's Coming Up Next
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