Don and Tom revisit the Social Security debate after new Wall Street Journal and New York Times articles challenge long-standing advice to delay claiming. They dismantle clickbait claims that “waiting doesn’t make sense,” highlighting emotional biases, unrealistic investment assumptions, and spousal benefit considerations. The episode also covers whether Social Security counts as an asset, then shifts to listener questions about 529-to-Roth rollovers for graduate school, switching funds in an IRA, and managing company stock in an ESOP-based 401(k). 0:00 Why they keep returning to Social Security and why 25% of retirees rely on it entirely 1:43 Two-thirds claim before full retirement age; Wall Street Journal’s clickbait headline 3:02 The “bird in hand” fallacy and instant-gratification bias 3:48 Don’s confession: took Social Security at 69—and dogs ruined the travel plans 4:40 WSJ’s faulty 5%-return argument and why most investors won’t achieve it 5:43 The math: waiting pays more monthly, but longevity is the unknown 6:32 Trade-offs between retiring early, portfolio drawdowns, and spousal benefits 7:35 NYT’s claim that Social Security is America’s most valuable “asset” 8:08 Don’s rebuttal: it’s income, not an asset—you can’t liquidate it 9:49 Why people misclassify Social Security and how bonds fit differently 10:08 When and how to get a second (fiduciary) opinion on claiming strategies 11:00 The plague of commission-driven “advisors” and fake fiduciaries 12:29 Old brokerage “no-load fund” lies and how similar games persist today 12:40 Listener Q&A: overfunded 529 plan vs. Roth rollover for grad school 14:27 Midwifery degrees, student-loan math, and the 5% rate cutoff 17:13 Rollover IRA question: switching Fidelity funds to Vanguard ETFs 18:15 Active vs. index funds—why fees and diversification matter 20:05 Active-active management and small-cap risk humor 20:54 ESOP question: how much company stock is too much? (Hint: under 5%) 22:42 Selling discipline and diversification in employee-owned firms 24:39 Don and Tom joke about their own ownership and “sell-out” strategy 25:04 Daily calls, good-natured ribbing, and reminders about Saturday’s live show Learn more about your ad choices. Visit megaphone.fm/adchoices