Getting hit with a tax bill in retirement usually isn’t bad luck—it’s lack of planning. In this episode, Jason Bergey explains why many retirees are surprised by taxes on Social Security, IRAs, and income timing, even after decades of saving. The discussion breaks down the difference between simply filing taxes and proactively planning for them, along with how different income sources are taxed in retirement. Jason also addresses confusion around annuities, guaranteed income strategies, and why understanding how money is withdrawn can make a meaningful difference over time.

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