Chris and Amy talk to Kerry Hannon, a senior columnist for Yahoo Finance, about the common regrets people face in retirement. From not saving early enough to taking Social Security benefits too soon, Kerry provides expert advice on how to better prepare for the future. They also discuss the benefits of automating savings, working with a financial advisor, and paying down debt before retiring. Despite these challenges, the conversation highlights the positives of retirement, including happiness, strong relationships, and a positive perspective on aging.