Jillian Johnsrud: 'Why retire once when you can retire often?'

Jillian Johnsrud, the podcaster behind "Retire Often," and the author of a new book out this week that goes by the same title, says that a lot of people mess up their retirement lifestyle by not preparing for it with smaller retirements — lasting a month or more — during their prime working years. Not only do these smaller times allow people to recharge and rejuvenate, they become dry runs for the real thing, allowing pre-retirees to sample ideas and then plan how to execute the best concepts. Johnsrud — who says she has retired at least a dozen times despite only being in her early 40s — says that small retirements are achievable, even by workaholics (like this show's host) with some foresight and planning.

Chuck Carlson, chief executive officer at Horizon Investment Services — longtime publisher of The DRIP Investor newsletter — returns to the show to help Chuck answer a listener's question about how to deal with an inherited portfolio of stocks all held in dividend reinvestment programs.

Chip Lupo discusses the 2025 Money and Relationships Survey from WalletHub, which showed that nearly one in three people think their relationship is limiting their financial growth, with communication (or a lack thereof) being at the heart of the problem.

And Chuck starts his interviews from FinCon '25 in Portland, Ore., by chatting with Doug Nordman of MilitaryFinancialIndependence.com, who says that while current events have some military members reconsidering their work choices, that action is appropriate and happens in all times, but it doesn't mean that military families will be abandoning their financial plans even if they change careers before achieving military status that could set them up for life.