Gathering at the Edge: Starting the Conversation
Inviting deeper connection through conversations about death, dying, and what matters most.
Talking about death is rarely easy and yet, it’s one of the most human, loving, and courageous things we can do. Whether you’re bringing it up with a parent, a partner, a friend, or a colleague, these conversations can stir up anxiety, fear, even resistance. But they also hold the potential for deeper connection, clarity, and care.
This toolkit begins at the edge: the edge of what we usually say, the edge of what we’re often taught to avoid. These prompts and role-based guides are designed to help you enter those edges with intention and presence. You’ll find scripts, reflection questions, and conversation starters tailored to different relationships, because how you talk to an aging parent may look different than how you talk to a teenager, a sibling, or a friend.
To help you prepare, you’ll also find somatic grounding exercises woven throughout. These practices are here to support your body as well as your mind, because the discomfort of these conversations often shows up in our breath, posture, and nervous systems.
You don’t need to push through. You can pause. You can take a walk, place your hand on your heart, or ground your feet into the floor. This work honors your whole self.
You don’t have to get it perfect. You can just begin.
Remember, you’re not trying to force agreement, you’re offering an invitation. Curiosity, presence, and vulnerability go a long way.
❤️ In addition to the conversation starters below, “conversation cards” will be coming in a later module of this toolkit with more ideas about how to talk to others about death, dying, and grief.
Grounding and intention setting
Begin by anchoring yourself. Ask yourself, “Before I begin this conversation, what values or hopes am I carrying with me?” Some examples might be connection, honesty, preparation, love, and presence.
Write or speak aloud your intention in one sentence.
“I want to talk about death because…”
“What matters most is…”
“I promise myself I will…(breathe, take breaks, stay kind)”
Conversation mapping (who, when, where)
Before we speak about death, it can be helpful to think about how to begin, and with whom. Not every conversation happens all at once and not every person needs to be approached in the same way. Taking a moment to map things out can help you move from overwhelm to clarity.
This next section invites you to slow down and consider the relationships that matter most, the settings that feel safe, and the timing that might support, rather than strain, the experience. Again, you don’t have to get it perfect. You just have to begin somewhere, with someone.
Let’s start by getting curious about who, when, and where. There’s no rush. Let this be a gentle opening.
Who do I want to talk with? (Make a short list.)
What kind of conversation do I hope for? (Informal? Planning? Sharing a story? Expressing fear?)
When would feel least pressured or emotionally taxing?
Where might we feel comfortable? (In the car? On a walk? Sitting outside? Around the kitchen table?)
Choose one conversation to begin with.
Starting the conversation
Even when we want to talk about death, the words don’t always come easily. It can feel awkward, emotional, or unfamiliar, especially if no one modeled these conversations for us before. That’s why having a few starting phrases can be so helpful. By now, I hope you know that you don’t need to say the “perfect” thing. You just need a way in.
This section offers simple, compassionate language to help you open, pause, and revisit these tender conversations. These aren’t scripts to memorize, but invitations to speak with clarity and care, in your own voice. You’ll also find some gentle prompts to help you reflect afterward, so you can stay connected to what the experience stirred in you.
Phrases for getting started
“I’ve been thinking about some big things lately, and I want to talk about them with you.”
“I know death isn’t easy to talk about, but I’d really appreciate it if we could try.”
“There’s no emergency. But I think it’s time we talk about what matters in the end.”
“Talking about death doesn’t make it happen.”
“This is hard. And it matters to me because I love you.”
“We don’t have to figure it all out. We can just talk honestly, little by little.”
This is a gentle invitation to use this somatic exercise before you get started:
Sit or stand with your feet flat on the ground.
Place one hand on your heart, one on your belly.
Inhale through your nose for 4 counts, hold for 2, then exhale through your mouth for 6.
Repeat 3 - 5 cycles.
Let your nervous system know: This matters, and I don’t have to rush.Pausing if it gets too hard
“Can I pause for a breath?”
“Let’s pause together for a breath.”
“This is a lot. Do you mind if we take a minute?”
“We can come back to this another time.”
This is a gentle invitation to use this somatic exercise if overwhelm, dissociation, or shutdown starts to arise:
Name 5 things you see
Name 4 things you touch
Name 3 things you hear
Name 2 things you smell
Name 1 thing you are grateful forRe-opening the conversation
“I’ve been thinking more about what we talked about death…”
“Can we revisit that conversation about death when we’re ready?”
“I appreciated you being willing to talk about death. It helped me.”
Reflection prompts after the conversation
What did I notice in my body during each conversation?
What surprised me?
What do I want to say next time that I didn’t say this time?
Who else might need this kind of conversation?
This is a gentle invitation to use this somatic exercise when you need to clear emotions after a difficult conversation:
Fill a bowl with water.
Name your grief aloud.
Dip your hands into the water, letting the weight move from you into the water.
Repeat as needed.
Conversation guides for different types of relationships
Talking with aging parents
This one can feel tender and complicated. Talking to our aging parents about death might stir up fear, grief, or resistance… in them and in us. But this conversation is also a gift. It's a way to say: I want to understand what matters to you. I want to carry your wishes with care. You might start by reflecting on how your parents have approached death in the past… what they said, or didn’t. What legacy did they inherit? You don’t have to dive in all at once. Start small. Start with love.
What to reflect on before the conversation:
What do I most want to know about my parents’ wishes?
What fears come up for me as I imagine this talk?
What messages about death did I inherit?
Questions you might ask them:
“What do you think matters most at the end of life?”
“What would feel most important to you if you got very sick?”
“Have you ever thought about what kind of care you'd want, or not want?”
“Do you remember how your parents talked about death? What would you want to do differently?”
Talking with adult children
This might be one of the hardest to initiate, not because they’re unwilling, but because they’re not ready to imagine life without you. But by having the conversation now, you give them something beautiful: peace of mind. Clarity. Permission. You might say: I want you to feel prepared, not panicked. This conversation is part of how I love you. You don’t have to have every answer. Start with your values. Share a few wishes. Ask what they’d want too.
What to reflect on before the conversation:
How might this talk help your children feel safer, not more scared?
What stories or memories do you want to make sure they carry?
Questions you might ask them:
“Is there anything you’d want to ask or talk about while I’m still here?”
“I know this isn’t easy, but I’ve been thinking about what I’d want if something happened to me. Can we make time to talk about it together?”
“I’m working on some end-of-life planning. This isn’t urgent, but it’s important to me that you know what I’d want and that I know what matters to you too.”
“I’ve been thinking about my values and what matters most to me. Can I share a little with you?”
“If anything ever happened to me, is there anything you'd want to know or have in writing?”
Talking with siblings
Siblings carry history. Sometimes that makes these conversations harder. Sometimes, it makes them sacred. You may have shared the same losses, like the death of pets, another sibling, a parent or grandparent, but grieved them differently. And those dynamics show up here, too. A conversation about death with a sibling might open old wounds. But it might also open a door to closeness, clarity, or even laughter. You’re not just talking about logistics. You’re talking about legacy, shared responsibility, and care.
What to reflect on before the conversation:
What parts of our shared history feel unresolved or unspoken?
What assumptions do I carry about how my sibling(s) will respond?
What’s one small place we might begin, without trying to do it all at once?
Questions you might ask them:
“What would you want to be different next time our family faces a death?”
“What role do we each usually take in family crisis and what would we each like to shift?”
“Do you want to create a shared ‘living legacy’ doc together, just to get a few things in one place?”
Talking with a partner
For many couples, talking about death isn’t about fear. It’s about love, protection, and preparation. This is someone you share a life with. You likely share bank accounts, a home, a future. Why not share this too? You could begin with curiosity: ‘Have you thought about what you'd want if something happened to you?’ Or bring humor in: ‘Do you want a Viking funeral, or a biodegradable mushroom coffin?’ At its heart, this conversation is a love letter, an act of intimacy. It says: Even when I’m gone, I’ll still be caring for you.
What to reflect on before the conversation:
What fears do I have about being honest here?
How might this bring us closer, not farther apart?
What does “a good death” mean to me, and have I shared that?
Questions you might ask them:
“I want us to be able to talk about what would matter if one of us died. I know it’s scary, but I’d rather face it together than alone.”
“Do you know what you’d want at the end of your life? I’d like us to talk about that sometime soon.”
“What parts of this are hardest or easiest to say aloud?”
Talking with young kids
Kids are curious. They ask the questions grownups are scared to answer: Where did grandma go? What happens when we die? The key is honesty, at their level. No euphemisms. No confusion. Just truth wrapped in reassurance. You might say: ‘When someone dies, it means their body stops working and they don’t feel pain anymore.’ Answer only what they ask. Let them play. Let them cry. Let them change the subject. You’re building trust, not answers.
What to reflect on before the conversation:
What words feel clear and simple enough?
What was I told about death as a kid, and what do I want to do differently?
Things you might say or do:
Use real words (“died,” not “passed away”)
Keep explanations short, clear, and honest: “We won’t see them again, but we can remember them and talk about them.”
Use stories, drawings, or toys to support expression
Draw a memory picture
Build a “feelings weather report”
Make a “grief box” with objects that feel comforting
Talking with teenagers
Teenagers are somewhere between knowing everything and feeling overwhelmed by everything. They might roll their eyes. Or they might surprise you. The key here is invitation, not instruction. You could say: ‘I’m thinking about my will and end-of-life stuff. Want to help me figure it out?’ You’re not just giving them information. You’re giving them a model of courage, emotional literacy, and preparation.
What to reflect on before the conversation:
What do I wish someone had told me as a teen about death?
How can I make this feel like a two-way conversation, not a lecture?
Questions you might ask them:
“Have you ever thought about what you’d want if something happened to someone close to you?”
“Would you want to help me figure out how to write down some of my wishes?”
“What have you seen or heard about death that stuck with you?”
Talking with close friends
Friends are often our chosen family, but we rarely talk about death with them until we’re forced to. Starting the conversation with friends can feel disarming or even weird. So go gently. Maybe it’s a meme. A story. A book you’re reading. A song that makes you think of legacy. You don’t need to be morbid. You can be curious. Playful. Sincere. Because when death enters a friendship, it deepens the soil. It says: You matter. I trust you. Let’s make space for the real stuff.
What to reflect on before the conversation:
What kind of support do I imagine from this friend if I died or if they did?
What have we already shared about loss or grief that we could build on?
Questions you might ask them:
“We’ve both lost people and I’ve been thinking about what we’d want if something happened to one of us. Want to talk about it sometime?”
“Can we make space to share a few memories of [name] together? It’s hard to carry it all alone.”
“Can I tell you something I’ve been planning for myself, in case anything ever happened?”
“This is hard to talk about, but I want to be thoughtful while I still can.”
“You’re someone I trust deeply. If something happened to me, I’d want you to feel clear, not left wondering. Can we talk through some of this together?”
“Okay, don’t freak out. I’m not dying. But I’ve been thinking about writing my funeral playlist. Want to weigh in?”
Talking in professional settings
Death doesn’t respect calendars. When it shows up, it shows up at work too. Whether you're navigating your own loss, supporting a grieving colleague, or facing a serious illness in your team, it’s okay to bring humanity into your work life. Professionalism and vulnerability aren’t opposites. You get to be both.
As is true in all of these conversations, this isn’t about having the perfect words. It’s about presence, permission, and compassion. Even small gestures can offer big relief.
If you’re grieving, you might say: “I’m going through a loss right now. I may need a little more space or flexibility as I move through it.”
If someone else is grieving or ill, go slow. Follow their lead. Acknowledge what’s happened without rushing to fix or avoid. Try: “I’ve been thinking of you. If you ever want to talk, I’m here.”
What to reflect on before the conversation:
What support have I needed, or wished for, during times of loss or illness at work?
What kind of workplace culture do I want to help create around death, grief, and care?
What role do I feel most comfortable playing (listener, advocate, quiet presence) and how might I grow in that?
Things you might say:
“I heard about your loss, and I just wanted to say I’m thinking of you. I’m here if you need anything.”
“I know everyone grieves differently. Please let me know what would feel most helpful or supportive.”
“Would it be okay if I checked in again next week?”
“It’s okay if you don’t want to talk about it, too.”
“Take the time you need. We’ve got you.”
“If there’s anything I can take off your plate, let me know.” (Be aware that this may be unwelcome to some people, so let them decide where possible.)
“I’m here to listen; no advice, no pressure.”
Closing
If you’ve made it this far, you’ve already done something courageous: you’ve begun. You’ve asked hard questions, explored tender relationships, and tried to find words for the things we’re often told to avoid. That matters.
These conversations might not go exactly as planned. They may feel messy, emotional, or incomplete. That’s okay. They’re not meant to be perfect; they’re meant to be human. And you’ve already started a ripple by naming what matters.
Remember: it’s okay to pause. It’s okay to circle back. These talks can unfold in layers, over time. Each one builds a foundation for clarity, connection, and care.
There’s more to come in upcoming modules, released each Thursday:
Diving deeper into conversations, with even more question to explore
Navigating grief, in all its unpredictable forms and supporting others, as they move through their own losses
Planning for end-of-life wishes, both practical and emotional
Honoring legacy and ritual, including creative ways to remember and be remembered
Take a moment now to check in with yourself. Maybe place a hand on your heart or take three slow breaths. Let yourself feel whatever comes: relief, discomfort, gratitude, even hesitation. It all belongs here.
This is the beginning of a deeper, more courageous conversation with life itself.
You’ve started something meaningful. Let that land.
And when you're ready, keep going.
Intro
Module One: Starting the Conversation (this post)
Module Two: Going Deeper in Conversation
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.