For many families, the biggest financial resource is the home—but selling it is emotional and often delayed until a crisis. That’s the downsizing dilemma. I worked with siblings who kept saying, “We’ll figure out the house later,” while paying thousands every month for their dad’s care. By the time they decided to sell, they were under pressure and had to accept a lower offer to simply afford their father’s care. If they started earlier, they could have planned for an estate sale, sold the house at market value, and invested the equity to generate more income. Introduce me to the adult child who says, “We’ll deal with the house when we have to.” What they really want is to make sure their parents can be cared for—without offending them or sparking conflict in the process. Ask them, “Do your parents still live in the same house you grew up in?”