On this episode of Simply Money presented by Allworth Financial, Bob and Brian put a $3 million retirement plan through a series of financial crash tests—from market downturns and overspending to helping adult children and losing a spouse. Plus, they lay out a five-year retirement countdown, explain how to help your kids without creating financial dependence, uncover tax opportunities that can emerge after your paycheck disappears, and reveal why checking your portfolio too often could do more harm than good.