An 88‑year‑old grocery store worker goes viral—and his story exposes a hard truth about retirement. This episode unpacks the cautionary tale behind a pension loss that forced continued work, then pivots to the real-world risks many retirees face: relying on a single income stream, market downturns, and outdated estate plans. The conversation explores building multiple income sources, balancing stability with growth, and why estate planning is about order—not wealth. From beneficiary mistakes to trusts and powers of attorney, this episode connects income planning, tax awareness, and legacy decisions into one clear retirement conversation.