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END OF LIFE PLANNING
How to Talk to Your Family About End of Life Wishes
(Without Making It Weird)
Published by Obitley Voices. Updated 2026.
Most people know this talk is important, yet so many keep putting it off.
According to The Conversation Project, 90% of Americans say talking about end of life wishes is important. Yet, fewer than 30% have actually done it. (The Conversation Project About, n.d.)
Often, people hesitate simply because they don't know where to start.
This guide is here to help you take that first step. It is for anyone hoping to talk with a parent, partner, sibling, or someone they love while there is still time.
Why This Conversation Is So Hard
Talking about death can feel like opening a door to something you would rather keep outside. You may feel as if saying the words might make them come true. That is not how it works. Still, the feeling is strong enough to keep people silent for years.
People also worry they will look like they are giving up on someone, or seem greedy or impatient. These fears are not real, but the worry about being misunderstood is.
Here is what truly matters: families who have these conversations before a crisis are less traumatized. They argue less and spend less. Afterward, they feel they honored their loved one's wishes instead of just guessing. (Effects of Advance Care Planning on End of Life Decision Making: A Systematic Review and Meta Analysis, 2017, pp. 1 10)
That is why the awkwardness is worth it. Now, let's see what actually needs to be discussed.
"The time to have the conversation is before a crisis, not during one " (Lin & Horowitz, 2025).
The Conversation Project
What You Actually Need to Know (The Four Areas)
End of life wishes are not just one conversation. There are four key areas to talk about, each important in its own way.
1. Medical Wishes
This covers decisions about care if the person cannot speak for themselves: do they want aggressive life sustaining treatment, or comfort care? Who is authorized to make medical decisions on their behalf?
Tools that help:
Advance directive (also called a living will): a legal document stating what a person wants if they cannot communicate Healthcare proxy (also called a durable power of attorney for healthcare): names a specific person to make medical decisions POLST / MOLST form: a more specific medical order for people with serious illness (completed with a physician) (Living wills and advance directives for medical decisions, 2024)
Five Wishes
Five Wishes is a widely used advance directive. It covers medical wishes, types of care wanted, comfort, treatment preferences, and messages for loved ones. More than 40 million copies have been sold in the US. It is legally valid in most states. (Five Wishes, 2024) Learn more at fivewishes.org.
2. Financial and Legal Documents
A crisis is even harder when important paperwork is missing. Here is what families need to know:
Is there a will? Where is it? Who is the executor? Are there trusts, life insurance policies, or retirement accounts? Are beneficiary designations up to date? (These supersede the will for many accounts, which is a common oversight.) Who has the financial or legal power of attorney? Who is the accountant? Attorney? Financial advisor?
You do not need to know every detail. You just need to know where everything is. You also need to know who is allowed to make decisions.
3. Digital Life
Most families overlook digital assets, yet managing them properly prevents difficulties for loved ones.
Digital assets include email accounts, social media accounts, and subscriptions, which may need to be closed or memorialized to prevent important information and memories from being lost. Digital Assets: For passwords and account access, is there a password manager in use? Who holds the master login credentials? Digital banking, investment accounts, and digital wallets such as those used for cryptocurrency require planning so funds are not inaccessible. Digital photos and documents: know where they are stored and specify what should happen to them, so memories and important files are preserved or shared properly. Online business assets, websites, domain names, and intellectual property
Facebook, Google, and Apple have specific rules for what happens to your digital accounts like email, photos, or social media after you die. (Duggan, 2013) Planning ahead is important. If you don't, your digital assets may remain active indefinitely or be locked away.
4. Personal Wishes and Legacy
This is the part most people skip, yet it often means the most to families when it matters most.
What does this person want their funeral or memorial service to be like? Burial, cremation, or something else? Who should be notified? Are there specific items, such as jewelry, keepsakes, or other objects, that they want to go to specific people? What do they want people to remember about them? Is there anything they want to say to someone who has never been spoken to? These are not just practical questions. They help someone be known, and families treasure these answers most.
How to Start the Conversation
Here are some approaches that really work. Choose the one that feels right for your relationship.
Start with yourself
The easiest way to begin is to be open about your own situation. Share what you have already done, or what you still need to figure out.
Try saying:
"I've been thinking about getting my own affairs in order and I realized I don't even know where to start. Can we talk about this together?"
"I don't have a will yet, and it's been bothering me. I wanted to ask you how you handled it."
Use a story from the news
A news story, a friend's experience, or a recent loss in the family can give you a natural way to start. For example: "I read about someone who died without a will and how hard it was for his kids. It made me want to make sure we have talked about this."
"After what happened with [name], I realized I don't actually know what you would want. Is that something you've thought about?"
Name the discomfort directly
Sometimes the best way is to admit the conversation feels awkward and have it anyway.
Try saying:
"I know this is a weird thing to bring up, but I love you and I don't want us to not talk about this."
"I've been avoiding this for a long time, which means I should probably just do it. Can we talk about end of life stuff?"
Frame it as a gift
This approach works especially well with parents who might worry that discussing these topics will weigh on their children.
Try saying:
"The most helpful thing you could ever do for me is tell me what you want. That way I'll know I'm doing right by you."
"I'm not worried. I just want to know. It would mean so much to me to have that information."
What to Do After the Conversation
Talking is just the first step. Writing things down is what makes them real and lasting.
Even a single page of notes in someone's own words is far better than nothing. Where are the important documents? Who should be called? What should their memorial look like? What do they want said, and by whom? These details matter more than you might think.
Frameworks that help
Five Wishes (fivewishes.org): a complete advance directive, available online and legally valid in most states The Conversation Project Starter Kit (theconversationproject.org): free, guided questions designed to help families capture preferences, available in multiple languages Get Your Stuff Together (getyourstufftogether.us): a practical workbook for organizing all the information a family will need (Five Wishes, 2026)
Write it down somewhere easy to find
If no one can find it, it might as well not exist. Keep important documents in a safe, known place. Make sure at least one other person knows exactly where that is.
Digital options include encrypted files, password manager notes, or secure platforms like Everplans. Physical options could be a fireproof document box, a clearly labeled folder, or storage with a trusted attorney. (End of Life Storage Planning, 2026)
Capture their story, not just their paperwork
Some things are not legal documents or instructions. They are simply part of who a person is.
These are the stories, the memories they want their grandchildren to know, the letter they have been meaning to write, and the values and beliefs that shaped their lives.
These things are often lost if they are not written down. Obitley's Life Story feature is made for this: a place to capture the whole person, not just the dates and arrangements, but the life that made them unique.
You can start a Life Story for yourself or someone you love at obitley.com at no cost.
Things Families Forget to Talk About
Even families who have these conversations often miss a few important things:
Pets: Who will care for them? This is often overlooked, and it can be very hard on a surviving pet. Make sure to name a caretaker clearly so no one is left behind. Digital assets: Social media accounts, cloud photos, subscriptions, and email. Most families do not think about this until accounts start sending birthday reminders or messages from the past. Specific keepsakes for specific people: "I want my granddaughter to have my mother's ring" is something that often never gets said. Too often, the ring ends up lost in an estate sale. Organ donation preferences: A sticker on your license is not enough. Your family needs to know your wishes and be ready to confirm them. What 'beautiful' means to them: It is not just about funeral details, but about what feels right. Some want a party, some want quiet, some want their favorite song played in a bar. The only way to know is to ask.
A Note on Timing
There is never a perfect moment for this conversation. If you wait for it, you might wait forever.
Families who are grateful they had this conversation always say the same thing: they did not realize how much they needed it until they finally sat down and talked together.
The people you love are worth truly knowing. Tell them, and ask about their wishes while you still can.
Sources
The Conversation Project About, n.d. https://theconversationproject.org/
Lin, S., & Horowitz, R. (2025). [Article Title].
Effects of Advance Care Planning on End of Life Decision Making: A Systematic Review and Meta Analysis, 2017, pp. 1 10.
Five Wishes, 2024. https://fivewishes.org/
Living wills and advance directives for medical decisions, 2024. Mayo Clinic. https://www.mayoclinic.org/
Duggan, M. (2013). Digital Assets and Death. Pew Research Center.
Five Wishes, 2026. https://fivewishes.org/
End of Life Storage Planning, 2026. [Publisher/Website].
Obitley Life Story. https://obitley.com/
Get Your Stuff Together. https://getyourstufftogether.us/
Frequently Asked Questions (FAQ)
Q: When is the right time to have the end of life conversation?
A: The best time is before a crisis, when everyone can talk calmly and openly. It's never too soon to start the conversation, and waiting for the "perfect moment" often means it never happens.
Q: What if my family doesn't want to talk about it?
A: It's natural for people to feel uncomfortable. Start by sharing your own wishes and feelings, or use stories or news events as an entry point. Sometimes, simply acknowledging the awkwardness helps.
Q: What are the most important documents to have?
A: Key documents include a will, an advance directive (living will), a healthcare proxy, and a list of digital accounts and passwords. Make sure these are easy to find, and someone trustworthy knows where they are.
Q: How do I bring up digital assets?
A: Explain that digital accounts, photos, and online subscriptions are part of your legacy. Ask if they've thought about what should happen to these things, and who should have access.
Q: What if my loved one refuses to discuss it?
A: Don't force the conversation. Let them know why this matters to you, and give them time. Revisit the topic gently after some time has passed.
Q: Is it ever too late to have this talk?
A: It's best to talk before a crisis, but even in difficult circumstances, having some conversation is better than none. Even a little clarity can make a big difference for families.
The Conversation Project (free Starter Kit): theconversationproject.org Five Wishes (advance directive): fivewishes.org Get Your Stuff Together (practical planning workbook): getyourstufftogether.us Obitley Life Story (capture who they are, not just what they had): obitley.com
For funeral professionals
Families who have had this conversation arrive better prepared. Sharing this article as a resource in a newsletter, on your website, or in early family talks is a true service that builds trust before a crisis ever happens.
Obitley business profiles help funeral homes across Western New York, Rochester, and Albany reach families searching for these resources. Learn about the Build Program.
Obitley Voices is a shared publishing platform for funeral professionals, caregivers, and families navigating loss.
Learn more at obitley.com/voices
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