The holidays are almost here. A time when many of us travel home, share meals, and spend long-overdue time with family. And while no one wants to bring up “serious topics” over turkey or Christmas cookies, this season also gives us something rare: time together. Time to talk, to listen, and to make sure the people we love are protected.
One of the hardest, yet most important, conversations you can have with aging parents is about estate planning. It’s not easy. No one wants to sound like they’re asking about money, and no parent wants to feel like they’re losing independence. But avoiding the topic doesn’t make the need for planning go away; it just delays it until a crisis forces everyone to make decisions under pressure.
Starting the conversation early, with care and empathy, can protect your parents, your family, and the legacy they’ve worked hard to build.
When It’s Too Late to Ask
Megan thought she was doing everything right. She helped her parents with their appointments, managed their bills, and checked in often. Then her father had a sudden stroke. When the hospital asked for his healthcare power of attorney, Megan realized they didn’t have one.
After hours of searching through old files, she finally found a will written more than 25 years ago. It named deceased relatives, had outdated information, and included no medical or financial directives. In the middle of a health emergency, Megan had to make decisions with no legal authority and no guidance from her parents’ wishes.
That stressful experience could have been avoided with one honest conversation and an up-to-date estate plan.
Why the Conversation Matters
No one likes to think about their parents getting older or facing health issues. But estate planning isn’t about preparing for death; it’s about protecting life, independence, and peace of mind. Talking about it now helps your parents:
- Stay in control of their decisions
- Avoid court involvement if they become incapacitated
- Reduce stress for their children during emergencies
- Make sure their legacy reflects their values, not default state laws
Bringing it up doesn’t make you nosy or pushy; it makes you responsible and caring.
How to Start the Conversation (Without the Awkwardness)
1. Choose the Right Time
The holidays may not be the moment for a deep dive into documents, but they’re a great time to start the conversation. After dinner, during a quiet morning coffee, or while wrapping gifts, you can open the door gently with something like:
“Mom, Dad, I’ve been learning a bit about estate planning, and it made me realize how important it is to have everything updated. Have you looked at your plan lately?”
or
“I want to make sure I can help you if something unexpected ever happens. Would you be open to talking about what plans you already have in place?”
Keeping your tone calm and respectful invites conversation instead of resistance. And if your parents feel more comfortable talking to a professional, suggest attending a workshop together.
2. Ask Questions, Don’t Lecture
No one likes feeling like they’re being told what to do. Ask gentle, open-ended questions that help your parents think through what matters to them:
- “Who would you want to make healthcare decisions if you couldn’t?”
- “Have you updated your will or trust recently?”
- “Do you have someone designated to handle finances in an emergency?”
- “Would you want to stay home if you ever needed long-term care?”
These questions come from love, not control.
At Bellomo & Associates, we often remind families that the best plans start with conversations, not forms. Once everyone understands the “why,” the documents simply reflect what’s already been discussed.
3. Focus on Love, Not Control
It’s natural for parents to fear losing independence. Reassure them that this isn’t about taking over, it’s about keeping them in charge.
You might say:
“I just want to make sure you stay in control of your choices, even if you can’t communicate them someday.”
or
“Having this in writing means no one can make decisions you wouldn’t agree with.”
That shift in perspective turns a difficult talk into an act of love.
4. Understand What a Complete Plan Includes
If your parents say, “We already have a will,” that’s a good start, but a will alone may not be enough. A complete plan usually includes:
- A will or trust to direct assets
- Financial and healthcare powers of attorney to authorize trusted helpers
- Advance directives for medical wishes
- Updated beneficiaries on accounts and insurance policies
Encourage them to review their plan with an attorney to make sure everything is current and coordinated.
5. Make It a Family Conversation
If you have siblings, consider having this conversation together. When everyone hears the same information, it helps prevent confusion and resentment later. A family meeting, especially one guided by an attorney, ensures transparency and unity.
6. Respect Their Privacy
Your parents may not want to share every financial detail, and that’s okay. The goal is to make sure the right documents exist, are up to date, and that someone knows where to find them.
7. Take It One Step at a Time
Estate planning can feel overwhelming, especially if it’s been years since your parents last reviewed their plan. Break it into small steps: gather important papers, schedule a workshop, and take things from there.
This isn’t a one-time talk; it is an ongoing conversation that changes as life changes.
The Real Goal: Protecting, Not Pressuring
Talking to your parents about estate planning isn’t about control. It’s about protection. Protecting their independence, their legacy, and the people they love most.
Megan’s story is a reminder that waiting for “the right time” often means waiting until it’s too late.
As the holidays bring your family together, take the opportunity to talk gently, honestly, and with love.
Estate planning is one of the greatest gifts you can give one another: clarity, comfort, and peace of mind.
Need help starting the conversation? Register for a Workshop and bring your parents along to learn how to plan with confidence.
