Is retirement really the most financially complex time of your life? That's what Fiona Greig, Vanguard's Global Head of Investor Research thinks. Mike Canet and Ryan Herbert dive into this question and unpack why the transition from saving to spending is more than just a financial shift—it’s an emotional and strategic overhaul. They explore how identity, income, taxes, estate planning, and long-term care all collide in retirement, and why working with a “phase two fiduciary” is critical to avoid costly missteps. Hear how one investor’s $14 million Bitcoin decision turned into a tax nightmare, and why timing and planning matter.

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