On this episode of Simply Money presented by Allworth Financial, Bob and Brian introduce the “financial freedom test drive”—a bold way to rehearse retirement before you take the plunge. Learn why trying out your withdrawal strategy and lifestyle early could save you from major surprises later. Then, they tackle the “millionaire’s income problem,” where pulling money out of your portfolio the wrong way can cost you in taxes, Medicare premiums, and peace of mind.

They’ll cover Roth conversion ladders, municipal bonds, rental income strategies, and real-world withdrawal tactics for people with significant assets. Plus, the guys share the uncomfortable but crucial conversation every couple should have: “What happens if I die first?” And finally, they break down the dream—and reality—of retiring overseas. From taxes to healthcare to missing Elder football games, this episode is packed with practical insight for high-net-worth families preparing for the next chapter.