What if being told to grab a part-time job in retirement is a sign something went wrong? On this episode, Derrick Caldwell challenges passive retirement advice, unpack active portfolio management, and walk through real-world decisions around Social Security, income timing and longevity. The conversation also explores Roth IRA conversions, tax tradeoffs, and why retirement planning works best when income, risk, and lifestyle are viewed together—without relying on hope as a strategy.

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