Retirement planning becomes a two-clock problem when spouses are a decade or more apart in age. Don and Tom explain why one household may need to fund two timelines—and why healthcare, Social Security timing, survivor taxes, and account ownership deserve extra attention. The older, higher-earning spouse may need to delay Social Security to age 70 to protect the younger survivor. A strong plan also models the household after one spouse dies, when income and filing status can change abruptly. Listener questions examine unusual model portfolios, rules-based versus discretionary fund management, and an expensive indexed annuity sold to an 81-year-old. The recurring lesson is simple: sound planning beats clever complexity. 0:49 The two-clock retirement problem 4:28 Healthcare and Social Security timing 7:12 The widow's tax and survivor planning 11:37 Portfolio backtests and the Golden Butterfly 19:02 Is rules-based investing active? 23:51 An unsuitable annuity sale