Midlothian resident Tracy Tynan says her mother, Evon, lived past 100, yet conversations about her future were few and far between. The subject almost felt taboo, though it was impossible to ignore what lay ahead.
“There was no ignoring that something was going to happen in the not-too-distant future because she was over 100,” says Tynan. “My mother wasn’t necessarily afraid to talk about it—she just wasn’t all that interested.”
As loved ones age, families are inevitably faced with big questions: Will mom remain at home after dad passes? Should dad stop driving? Is there an estate plan in place? Should parents consider downsizing or moving into a retirement community?
The list can feel overwhelming, but experts agree the first and most important step in securing a loved one’s future is simply starting a dialogue.
“When you begin to see impairments or red flags, it’s time to have a conversation,” says Karyn Walsh, a licensed clinical social worker with the Northern Virginia Older Adult Counseling Center in Fairfax. “But, ideally, you want to have a conversation before that happens.”
Advanced care planning can cover a wide range of decisions—from housing and transportation to medical directives, finances, and additional help at home. While these are not easy conversations, they pave the way for older adults to shape the future they want for themselves.
Estate Decisions
Decisions made in the twilight years don’t just affect daily life—they also determine what happens after a loved one passes. Angela Costello of Yorktown, an ordained chaplain who has presided over many funerals, has seen the pain that comes when no plan is in place and families are left to guess at their loved one’s wishes.
“You want to make sure you are making the decisions that you’re confident they would want, because you don’t want to live with thinking maybe you made the wrong decision or it was contrary to what they wanted,” Costello says.
In her own family, Costello carries a measure of regret. Both of her parents passed away in recent years, and while she had some conversations with them, she wishes she had done more.
“I think I would have made more time when I was at my busiest and they were at their most lucid,” she admits, “to push the issues and to listen to what they were trying to tell me, and to ask the questions.”
Hot Topics
The topics can be wide-ranging, from long-term care and financial planning to driving, nutrition, and caregiver needs. Sometimes, short-term strategies must be put in place after an event like a fall or hospitalization—and those moments can provide a springboard for deeper conversations.
“If somebody has had an accident, you might need to think about short-term strategies until you know they’re better or it’s safe for them to drive or for them to be home by themself,” Walsh says. “You may need to bring in the assistance of a doctor, because the first consideration is always harm reduction.”
Costello notes that practical matters—like knowing where safe deposit box keys are, where copies of trusts and wills are kept, or what a loved one’s funeral wishes may be—are equally important, even if the discussions feel uncomfortable.
“In hindsight, I would tell myself not to be afraid of that conversation (about their passing), that just because I’m talking about it doesn’t mean I’m somehow calling it into being,” she says. “What I’m doing is actually putting safeguards around them to protect them.”
The baseline for any conversation around advanced care planning, Walsh says, is simple: Follow the golden rule. “Treat others as you want to be treated, not talking down to them, but talking to them as a person with dignity and worth,” she says.
This article originally appeared in the December 2025 issue.
