Sixty percent of recent retirees admit their spending plans are already failing, proving that the transition to life without a paycheck is rarely a straight line. Curtis James of Bear Market Financial Services dives into the reality of the "retirement bummer"—where unexpected healthcare costs, market volatility, and tax traps can freeze even the best-laid plans. From the psychological hurdle of paying off a mortgage to the dangers of "DIY-ing" your strategy with AI, this episode explores how to build a flexible, written roadmap that prioritizes income preservation over paper wealth.

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