On this episode of Simply Money presented by Allworth Financial, Bob and Brian reveal why your retirement plan may no longer match your reality—especially after three strong years in the market and inflation sticking around 3%. Then, the millionaire’s income problem: building wealth was the easy part—how you draw it down could make or break your retirement. The guys dig into Roth ladders, tax-smart income planning, and whether muni bonds or dividend portfolios really make sense at your tax bracket. Also tonight: Why your Social Security claiming strategy isn’t “set it and forget it,” how illiquid real estate could wreck your retirement flexibility, and the honest conversation every couple needs to have: “What happens if I die first?” Plus, practical tips on modernizing inherited investments, stress-testing DIY portfolios, and whether retiring overseas is really the dream—or a future headache.