This episode explores the psychological and financial side of retirement planning through the lens of entropy. Don and Tom dive into an article from Kiplinger that cleverly compares retirement to the second law of thermodynamics: left unmanaged, both money and purpose tend toward chaos. Only 4% of retirees say they're "living the dream"—and the duo explores why that number is so shockingly low. From maintaining routine and finding meaning to avoiding common money traps like over- or under-spending, this episode is packed with practical insights and sardonic banter. Plus, listener questions on Roth conversions for low-income parents and generating sustainable income in retirement portfolios.

0:04 Why we're talking thermodynamics on a money show
1:40 The "Second Law" of Retirement: Life drifts toward chaos
2:15 Only 4% of retirees say they're "living the dream"
3:06 Why retirement can be scary—even for us
4:44 Do something in retirement... but get paid for it?
6:09 Volunteering vs. purposeful work (and airplane nostalgia)
7:03 Retirement spending traps: splurging or hoarding
8:09 The danger of financially supporting adult children
9:43 Composer John Williams and the myth of retirement
11:24 Three keys to a better retirement: social, purpose, activity
12:04 Paul Merriman, semi-retirement, and finding meaning
13:23 It all still comes down to money—and the freedom it brings
14:42 Steve Martin's quote on money and dumb stuff
15:30 Listener question: Tax-efficient Roth conversions for elderly parents
20:07 Listener question: Income generation with ETFs vs. income funds
22:51 Junk bonds, Franklin Income Fund risk, and total return
25:48 Strategy tip: Keeping a year of cash to smooth out volatility
26:11 Upcoming events and Apollo's July 9th appearance
27:37 Free portfolio review offer and purpose in helping others
28:51 Tom's boat motor saga and 1-star review nightmares

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