What happens when retirement planning starts to feel like rolling the dice? On this episode, Eric Hutter uses pop-culture flashbacks and real market history to frame a candid conversation about risk, volatility, and timing as retirement approaches. The discussion explores why age and market cycles matter, how diversification goes beyond stocks, and where guaranteed income buckets may fit. The episode also examines Roth conversion timing, common missteps, and the value of stress-testing a portfolio before uncertainty forces hard decisions.

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