You and Tom take on the myth of hard-and-fast financial rules by walking through Real Simple’s list of nine “rules you can break.” From the latte factor to credit cards, budgeting, bulk shopping, and the old “retire at 65” trope, the conversation keeps coming back to a single theme: money isn’t black and white. You push back against absolutists like Dave Ramsey, emphasize discipline over dogma, and highlight the practical realities of saving behavior, debt, lifestyle choices, and risk. Listener calls round it out — including a thoughtful inheritance question and a late-career investor worried about having “run out of time,” which you defuse with smart, flexible solutions.

0:04 Absolutism vs. nuance in personal finance

1:24 Dave Ramsey’s black-and-white rules

1:57 The latte rule and small vs. big expenses

3:36 Pay-yourself-first as the only rule that really works

4:57 Are credit cards bad? Protection, perks, and pitfalls

6:26 Truth lives between extremes

7:45 “Breakable” money rules from Real Simple

8:39 The myth of retiring at 65

9:59 Why more people work past traditional retirement age

11:00 Don’s TV story and accidental age-compliment

12:59 Is bulk shopping really a money saver?

13:55 Why strict budgets fail

15:04 Tom’s failing FaceTime and tech-phobia

16:02 Caller: leaving money to grandkids who vanished

19:43 Family lawsuits when inheritances differ

20:23 Caller: asset location and bond placement

24:55 Should you draw from 401(k) or IRA first?

28:43 Caller: “Am I out of time to retire?”

33:00 Solving retirement shortfall with portfolio structure

36:16 Don runs the numbers — immediate annuity option

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