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Conversation Guide: Discussing Aging with Parents

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Talking to your parents about aging and end-of-life wishes can feel uncomfortable, but it is one of the most important ways to love and honor your parents. These conversations reduce uncertainty, prevent conflict, and ensure their values and wishes are respected.

This guide will help you navigate the conversation

 

The Setting

Because the subject is sensitive, choose a relaxed, non-stressful time. Consider the time of day as well. If they are a morning person or afternoon person, choose the best time when they are most comfortable and mentally engaged. 

Expect that it may take more than one conversation. 

The Conversation

Ask Permission to Begin

Starting with permission demonstrates respect and helps lower defensiveness. Some ways to open the conversation include:

  • “Even though you’re OK right now, I think about you getting older and I want to be ready to help if needed. Can I ask about your wishes and any plans you’ve made?”
  • “I want to know how you’d both like to be cared for toward the end of your lives. Do you mind if we talk about that?”
  • “I’ve learned about the financial and legal steps experts recommend to be prepared for later life. Can we talk about those?”
Explore Living Arrangements and Care

Living situations and care needs often change with age. For widowed or single parents, these questions become even more significant.

  • Have you thought about where you’d like to live if your current home becomes too much to manage?
  • Would your preferences change after one of you passes away?
  • Have you thought about who would provide caregiving, if needed?
  • Do you have long-term care insurance?
Review Documents and Key Advisors

Ensuring proper legal and financial documentation prevents confusion and provides clarity when decisions must be made.

  • Do you have a will, and if so, who have you chosen as executor?
  • Have you appointed a health care proxy to make decisions if you cannot?
  • Do you have a financial power of attorney?
  • Have you clarified how much medical intervention you’d want with a living will or Do Not Resuscitate order?
  • Where are your important documents kept?
  • Should I meet with your financial professional or attorney?
Check In on Feelings

End-of-life conversations are not only about information but also about emotions. Closing with gratitude and reassurance builds trust.

  • “I really appreciate your talking with me about this. I hope you know my questions come from love and from wanting to honor your wishes. How are you feeling right now?”
  • “Thank you for talking to me about this. Do you have any questions for me?”
Keep the Conversation Ongoing

This is not a “one and done” discussion. Circumstances and preferences change. Returning to the topic occasionally helps ensure plans remain appropriate and up to date.

When Parents Are Not Receptive

Not every parent will be ready or willing to engage in end-of-life planning discussions. If you encounter resistance, do not press too hard. Instead:

  • Acknowledge their feelings. Reassure them that you understand the topic may feel uncomfortable, overwhelming, or even unnecessary right now.
  • Keep the door open. You can gently say, “That’s OK, we don’t have to talk about this today. I just want you to know I’m here whenever you’re ready.”
  • Start smaller. Instead of addressing everything at once, focus on a single practical item—such as where important documents are stored, or whether beneficiary designations are current.
  • Use outside resources. Sometimes parents respond better when information comes from a trusted professional (doctor, financial advisor, attorney) rather than from family.
  • Revisit later. Circumstances, health, or life events may create natural opportunities to bring the subject back up with less resistance.

Remember, the goal is to respect your parents’ autonomy while keeping communication channels open. These conversations are a process, not a one-time event.

Resources

Here are a few resource articles around estate planning that may be helpful for you:

Steven Gilbert

Steven Gilbert CFP® is the owner and founder of Gilbert Wealth LLC, a financial planning firm located in Fort Wayne, Indiana serving clients locally and nationally. A fixed fee financial planning firm, Gilbert Wealth helps clients optimize their financial strategies to achieve their most important goals through comprehensive advice and unbiased structure.