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DO THIS for a Happy Retirement (feat. Wes Moss)

August 19, 2026

AI Summary

5 min read

In the 2024 update to his long-running research on retirement happiness, financial planner Wes Moss found something striking: over 80% of happy retirees say they get enough sleep, compared to only 41% of unhappy retirees. That two-to-one gap was a surprise even to Moss, who had never asked about sleep before. But it fit a larger pattern he has spent more than a decade documenting: the ingredients of a genuinely happy retirement have less to do with a specific dollar amount and more to do with a handful of measurable lifestyle factors—especially community, purpose, and the deliberate creation of a new daily structure.

The Research Method: Studying the Happy Minority

Moss’s approach is unusual in the personal finance space. Instead of asking people what they think they need in retirement, he identifies the population that is already retired and happy, studies what they actually do, and compares it to what unhappy retirees do. That core comparison—what he calls "happiness alpha"—drives his new book, Retire Sooner Method. The 2024 update uses a statistically significant sample mapped to the U.S. Census, and Moss added questions about health and sleep that he had not included in his earlier work.

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What you'll learn

  • 1 (03:51) **Wes Moss Introduces His Data-Driven Approach to Happy Retirement** - Wes explains how his research started by studying the happiest retirees and comparing them to the unhappiest to find what really drives satisfaction.
  • 2 (09:17) **The "Happy Retirement" Snake Draft Begins** - The hosts and Wes draft from twelve factors to build the ideal happy retirement, revealing their priorities and strategies.
  • 3 (16:32) **Wes Judges the Drafts and Explains the Real Winners** - Wes critiques each host's draft picks based on his research data, declaring a winner and explaining why certain factors are overrated.
  • 4 (22:03) **The "Happiness Alpha" of Financial Freedom** - Wes reveals a key chart showing the massive 21% jump in happiness when a person can say they are financially free, even if they still choose to work.
  • 5 (25:05) **Travis's Question: Optimal Order of Withdrawals in Retirement** - The team explains the ideal strategy for drawing from taxable, traditional, and Roth accounts to minimize taxes in retirement.
  • 6 (29:35) **The Personal Nature of Withdrawal Sequencing** - Wes and the hosts agree that the "order" changes dramatically based on personal factors like Social Security, Medicare, and RMDs.
  • 7 (32:24) **RiverSniper09's Question: HSA vs. Cadillac Plan for a Baby Year** - The team advises a soon-to-be parent on whether to switch from a high-deductible HSA plan to a traditional PPO for a year with high medical expenses.

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Guests on this episode

Show Notes

Retirement happiness isn’t just about how much money you’ve saved—so what actually matters most? Brian, Bo, and retirement researcher Wes Moss put it to the test with a Retirement Happiness Draft, taking turns building their ideal retirement from 12 choices like $100K of income, eight hours of sleep, close friends, travel, hobbies, a paid-off home, and multiple income streams. Who builds the happiest retirement? Along the way, they unpack new research on happy retirees, retirement planning, financial independence, health, relationships, and purpose after work—and reveal what the data says really separates a fulfilling retirement from an unhappy one.


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