Gathering at the Edge: Going Deeper in Conversation
Continuing to explore conversations about death, dying, and what matters most.
Welcome to this module of Gathering at the Edge, where we dive deeper into one of the most human (and often most difficult) things we can do: talk honestly and openly with each other about death, grief, legacy, and care.
While it may not be easy, it also doesn’t have to be isolating or clinical. These conversation prompts were created to continue the work you started with the last module of opening up gentle, meaningful dialogue about topics that often get pushed aside until it’s too late. You get to choose what feels okay to speak to, what needs more time, and what’s best left unspoken for now.
The prompts are grouped by topic and emotional depth (easy, medium, and hard) so you can go at your own pace. You might use them:
As journal prompts or reflection starters
In conversation with family, friends, or care teams
During a walk or while sitting together in person or virtually
As support tools for coaches, doulas, or anyone facilitating end-of-life discussions
Or even just to name the questions you’re not ready to ask aloud yet
This isn’t about scripting the right thing to say, but rather about opening a door. Let these questions be tools, not tests. Use them as invitations to slow down, speak from the heart, connect, feel, remember, and wonder. Within you exists the courage and space to honor the truths we don’t always say.
Before you begin, take a breath.
Place your hand on your chest.
Notice how your body feels.
Let the moment settle.
You don’t need to push past discomfort.
You don’t need to rush toward a goal.
Just begin where you are.
You might say aloud or quietly to yourself:
“I don’t have to have all the answers.
I’m just here to be present with what’s real.”
Conversation prompt cards
These prompts are part of a larger deck that’s currently in development as both analog and digital conversation cards: something you can hold in your hands or scroll through on a screen, like a cross between an oracle deck and a storytelling game.
Eventually, these cards will be available in a more tactile, shareable form that you can bring to the dinner table, pull during a walk, or offer to a loved one as an invitation into deeper dialogue. For now, they’re laid out here as a collection of written prompts to get you started.
You don’t have to go deep to go meaningful. You don’t have to finish what you start. Let your intuition guide you.
These questions are meant to meet you where you are and walk with you from there. They’re designed to acknowledge that grief and death bring up vulnerability, history, and emotion and they welcome nonlinear thinking, pauses, repetition, or emotional regulation tools as needed.
There’s no right way to use them, just the way that works for you.
Some people might feel relief at the opportunity to talk about the subject of death and dying. Others might feel discomfort, fear, or fatigue. That’s all welcome. Grief and death are human experiences and talking about them together is a way of staying connected to each other and to what matters most.
1. Starting the conversation
Easy
“What’s a memory that brings you peace?”
“When do you feel most alive?”
“What’s one thing that always makes you laugh?”
Medium
“When was the last time you thought about death? What brought it up?”
“What does a good death mean to you?”
“Who do you trust to speak for you if you couldn’t?”
Hard
“What’s something you’re afraid to say out loud about dying or loss?”
“If you couldn’t speak for yourself, what would you want others to know?”
“Have you ever imagined your own funeral? What stood out?”
2. Grief and emotional legacy
Easy
“What does your grief feel like in your body?”
“What small things help you feel comforted or held?”
“Who has supported you through a difficult time?”
Medium
“What surprises you about your grief?”
“What helps you when grief flares up?”
“Is there something others say about grief that actually feels supportive or not?”
Hard
“Have you ever felt pressure to grieve a certain way?”
“What’s a loss you haven’t talked about much?”
“What do you wish more people understood about your grief?”
3. Family, relationships, and repair
Easy
“What’s one story from your childhood you want remembered?”
“What’s something funny or quirky that’s so you?”
“What family traditions connect you to your roots?”
Medium
“What stories do you want passed on?”
“Is there something between us that hasn’t been said yet?”
“What do you want us to remember if you're not here someday?”
Hard
“Is there something you’ve forgiven or want forgiveness for?”
“What part of our relationship do you wish we could heal?”
“What roles or expectations in our family would you want to release?”
4. Meaning, legacy, and impact
Easy
“What do you hope people remember about you?”
“What songs, places, or rituals feel like you?”
“What’s a moment that made you proud of who you are?”
Medium
“What would you want your obituary to say?”
“What traditions do you hope your people will continue?”
“What objects or belongings feel most meaningful?”
Hard
“What meaning do you make from your life and your mortality?”
“If you could leave behind one piece of advice, what would it be?”
“What impact do you hope your life has had on others?”
5. End-of-life wishes and care
Easy
“What would your ideal last meal be?”
“Who do you want with you at the end of your life?”
“What music brings you comfort?”
Medium
“What poems, songs, or readings do you want shared at your funeral?”
“How do you want your body to be cared for after death?”
“Are there specific care settings you’d prefer: home, hospice, hospital?”
Hard
“Are there any end-of-life decisions you need help making?”
“What unfinished business do you want to resolve before you die?”
“Under what circumstances would you not want life-prolonging treatment?”
6. If you die first
Easy
“Who should be contacted first?”
“What little things would you want someone to remember to do or say?”
“Are there messages you’d want shared on your behalf?”
Medium
“Are there accounts, passwords, or subscriptions someone should know about?”
“Who should take care of your pets, projects, or belongings?”
“What kind of emotional support might your loved ones need?”
Hard
“What do you fear most about dying before the people you love?”
“What do you want your loved ones to know if you die first?”
“What do you hope your death might teach the people who love you?”
7. After you’re gone
Easy
“What would you want written about you for your obituary, gravestone or memorial?”
“What do you imagine your people doing on the anniversary of your death?”
“What message would you leave for your future great-grandchildren?”
Medium
“What rituals or remembrances feel comforting to imagine?”
“How can people honor your memory without it becoming a burden?”
“What stories or traits do you hope live on?”
Hard
“If you could witness your loved ones after your death, what would you hope to see?”
“How do you want others to grow or heal in your absence?”
“What legacy do you think you're leaving, intended or not?”
8. Specific conversations
Talking with your medical proxy:
“If you ever had to speak for me, I want you to know what I’d want.”
“What would help you feel clear and supported if that day ever comes?”
“Let’s talk about what quality of life means to me.”
Talking with your executor:
“Here’s where I’ve documented my legal and financial plans.”
“I want to make this role easier for you by being as clear as possible.”
“What questions do you have about what I’m asking of you?”
If things get hard along the way
It’s okay if this work stirs something up. That’s part of the process, not a sign you’re doing it wrong. If you find yourself feeling overwhelmed, tender, shut down, or uncertain, may these be gentle invitations to care for yourself in the moment:
Shift your attention
Look around the room and name five things you can see.
Step outside, even briefly, and name one thing that’s alive or moving.
Find a color around you and follow it with your eyes for a few moments.
Go off-script
Skip the question that feels too sharp or raw right now.
Rewrite it in your own words, in a way that feels softer or more true.
Answer a different question or just create whatever wants to be said.
Connect to something grounding
Hold an object that carries meaning for you like a stone, scarf, photo, etc. Let it bring you comfort.
Light a candle or turn on a small lamp. Let its warmth be a pause.
Wrap yourself in a blanket. Let yourself feel held.
Change the container
If you’re sitting, stand. If you’re inside, move near a window.
Take your conversation or reflection into a different room or outside.
If talking feels too much, try drawing or writing.
Name what’s happening
“This is a lot right now.”
“I didn’t expect that to land so hard.”
“This brought something up, but I’m not sure what yet.”
Jot down one feeling or word and come back to it later with curiosity.
These practices aren’t meant to bypass discomfort, but to help you stay connected to yourself as you move through it. You don’t need to force anything. You can stop, shift, or return later. This work honors your pace as well as those you’re connecting with.
Closing
If you’ve spent time with even one of these cards, you’ve already done something powerful. You’ve stepped toward truth. Toward connection. Toward love.
You may have stirred up big feelings of grief, fear, tenderness, even laughter. You may have left some questions unanswered. That’s okay. These cards are meant to start conversations, not finish them. Let them echo. Let them return. Let them lead you somewhere unexpected.
In the days ahead, you might find a question lingering. You might remember something someone said. You might notice that a conversation that once felt impossible now feels… slightly more possible. That’s what this work does.
Next Thursday, we’ll move gently into our next module: Navigating Grief. It’s a space to explore the wild, nonlinear terrain of loss, memory, anger, love, and meaning. We’ll include somatic practices, creative reflections, and ways to support both your own grief and that of others.
Until then, keep listening, to your body, to your breath, and to the quiet wisdom that comes when we make space for what matters.
You’re doing brave, meaningful work. Let that land.
Intro
Module One: Starting the Conversation
Module Two: Going Deeper in Conversation (this post)
Module Three: Navigating Grief (coming July 10)
Disclaimer: This toolkit is not a substitute for professional mental health care. I am not a licensed therapist, counselor, or medical provider. The content offered here is for educational and supportive purposes only. If you are experiencing overwhelming distress or need mental health support, please reach out to a qualified professional or crisis resource in your area.