Jane Pauley hosts our special broadcast focusing on securing a fulfilling retirement. In our cover story, David Pogue looks at the state of Social Security. Also: Susan Spencer explores the creation of bucket lists; Robert Costa talks with Drew Barrymore who, at 50, landed on the cover of AARP: The Magazine; Seth Doane travels to Malta, where Americans are finding a more affordable retirement home; Kelefa Sanneh talks with the "father of the 401(k)"; Faith Salie meets "grandfluencers," older content creators who are finding post-retirement careers on social media; Lee Cowan checks out a site for retired warplanes; Tracy Smith sits down with the comedy duo Cheech & Chong, now starring in a new movie, while Martha Teichner explores Latitude Margaritaville, a 55+ active community in Florida inspired by Jimmy Buffett; and Conor Knighton visits a retirement home for chimpanzees.