There’s No “Never” in Retirement Planning

Is there anything you should truly never sell in retirement? Or is that kind of thinking too rigid for real life?

In this episode, Chris Boyd is joined by Brian Regan, Luke Bagley, and Vincent Sansone to challenge a popular article claiming retirees should avoid selling certain assets—like appreciated stocks, life insurance, or even their home. The team breaks down why blanket advice like “never sell” can be misleading, and why thoughtful, individualized planning matters far more than following hard rules.

The conversation explores key retirement decisions, including when it might make sense to sell appreciated investments despite taxes, how to evaluate old life insurance policies, and whether downsizing your home could actually improve financial flexibility and quality of life. Along the way, the group highlights the importance of balancing long-term legacy goals with actually enjoying retirement.

If you’ve ever wondered how to weigh tax efficiency against lifestyle—or how to make smarter, more flexible decisions as you approach retirement—this episode offers a grounded, practical perspective.

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