Forest Hill's Jeff Judge in Stanford Center on Longevity: The parent conversation families keep avoiding

By Jeff Judge, CFP®, AEP®, ChFC®, CLU®, Managing Partner, Chesapeake Financial Planners, Forest Hill, MD.

Most families I work with have the funeral conversation. Wills, burial wishes, final arrangements, all handled. It's the conversation before that one, about how a parent wants to live if they lose some independence, that keeps stalling out.

A journalist asked me why that gap exists, and my answer was simple. A funeral plan has an end point. You make the decision once and you're done. The conversation about frailty, dignity, and who gets a say never really closes, so a lot of families quietly avoid it. I told her adult children often treat their aging parents like a project with a checklist, when this is a relationship, and money should be part of a much bigger conversation about a parent's dignity and their fear of becoming a burden.

For families here, that gap shows up early. Retirees in Perry Hall and Cockeysville are having the checklist conversation with their own kids right now, and parents in Bel Air are often the ones quietly avoiding the harder one. A parent who resists talking about assisted living usually isn't being stubborn. They're afraid of losing control over their own life.

The families who navigate this well ask a different question. Not what's the plan, but what does a good future look like for you. That one question tends to open a door a checklist never will.

This piece builds on "What Aging Parents Want the 'Kids' to Know," in Stanford Center on Longevity (September 2026).

Jeff Judge, CFP®, AEP®, ChFC®, CLU®, is Managing Partner at Chesapeake Financial Planners in Forest Hill, MD. Book an intro call.