Don and Tom run through a Wall Street Journal list of “subtle signs it might be time to retire,” reacting to each one with their usual mix of disbelief, personal anecdotes, and gentle ribbing. The episode wanders into tech reluctance, job promotions nobody wants, Sunday dread, obsessive 401(k) checking, volunteering guilt, missing peers, feeling left out of friends’ retirements, boss-related misery, and aging knees. They also answer listener questions about Schwab Intelligent Portfolios and their high cash allocations, discuss the shrinking role of physical cash, explain the real value of pre-1964 silver quarters, and handle calls on Social Security math. Tom repeatedly tracks his daughter’s high-school soccer match on-air, providing live updates as the drama unfolds.

1:06 WSJ list of “subtle signs it’s time to retire” begins

1:40 Sign #1: Feeling numb arriving at work

2:11 Why neither host relates to workplace numbness

2:59 Sign #2: Shrinking from new tech tools (Tom jokes incoming)

3:40 Don embraces AI, Tom… less so

4:21 Sign #3: Avoiding promotions; why neither wants a bigger job

5:16 Sign #4: The “Sunday scaries”

5:50 Sign #5: Constantly checking your 401(k) balance

6:26 Mid-list recap before the break

7:42 Second half of the list introduced

8:57 Sign #6: Wanting to volunteer more

9:40 Sign #7: Realizing all your peers have retired

10:11 Don jokes about dying at his desk

11:34 Sign #8: Feeling left out as friends enjoy retirement trips

12:40 Sign #9: Hating your boss (and why that’s not a retirement issue)

12:56 Sign #10: Achy knees and “retire before you can’t enjoy things”

13:35 Doctors, guarantees, and aging joints

14:43 Call for listener questions

15:04 Call: Schwab Intelligent Portfolios’ big cash allocations

16:28 How Schwab makes money on the spread

18:20 Transparency vs. hidden fees

20:20 Back from break — Wednesday podcast explanation

21:31 Don hates change (the coin kind and the life kind)

22:30 Historical buying power of coins

22:56 Pre-1964 silver quarter value

24:15 Odds of finding one in circulation

25:10 What amount of money makes you bend over and pick it up?

25:47 Cleaning out the garage vs. hunting silver coins

27:36 Halftime soccer update: the comeback begins

29:02 Caller: misunderstanding “8% interest” from Social Security discussion

30:26 Caller Paul on cash vs. cashless society

31:51 Coca-Cola prices through time

32:57 Only 12–18% of payments today are cash

34:02 Holiday well-wishes and generational shifts

35:34 Bewitched, credit checks, and pre-internet detective work

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