The best way to start the conversation is to ask a question with an open heart.

Be real. Be you.

All of us will have these sorts of conversations in different ways. There is not one right or good way to do it. What matters most is showing up and being real. Be authentic. Don’t worry about putting on a confident performance. Don’t try to be perfect. Just simply and honestly do what feels ok to you. Most people are not asking for a ‘correct’ conversation with an ‘expert’ who ‘knows lots’ about death and will give them some sort of service. Instead, most of us are hungry for real, messy, relational, equal, honest connections.

Persist.

In a society that gives us few models and few rituals to help us practice these courageous conversations, it can feel like there is lots of pressure to stop talking (or to not even try in the first place). This takes a bit of faith. This takes time. It takes practice. It takes courage. Stay curious and keep learning. There is extraordinary possibility in little, regular, open-hearted invitations to chat together about illness, aging, and dying.

ALL of the feelings are okay.

Talking about these things is heart work. Real conversations are likely to get a little bit uncomfortable and bring up feelings (sadness, anger, grief, confusion AND joy, hope, passion, love). That’s ok. Having feelings, showing them, and expressing them is not wrong. This is often a signal of being authentic and genuine. You don’t have to be in control. There are two important things to remember about feelings:

• If someone cries or gets sad, it is very unlikely that you will have made them upset. Instead, it is far more likely that they are crying because you have given them space and permission to be upset. You have shown them that they don’t have to be upset on their own—they are not alone. They have permission to share their feelings with you. This is a gift, not a problem.

• Just because someone tells you about their feelings, that does not make you responsible for solving or fixing anything. Just listen. It is often far more valuable to share real feeling than to try and share answers and solutions.

“We think that the point is to pass the test or overcome the problem, but the truth is that things don't really get solved. They come together and they fall apart. Then they come together again and fall apart again. It's just like that. The healing comes from letting there be room for all of this to happen: room for grief, for relief, for misery, for joy.” Pema Chödrön

Be curious (ask, ask, ask).

Asking questions sounds like a very obvious tip for how to deepen conversations. But it is surprising how little we all actually do this. So often, we are doing the equivalent of putting on a presentation, holding a meeting, or giving a sermon—rather than just asking a couple of genuine questions. Asking open questions from your heart goes a long way to starting a conversation and making it more meaningful.

Ask for help.

Instead of telling people what you think, try starting by asking for their help or their ideas. You might say something like: “I am worrying about ….. What do you think I should do about it?” Ask people to share their experiences with you by saying something like: “I am not sure what the right thing to do is in this situation. What do you think? How have you or your family handled something similar?” You don’t have to agree with their views - and they don’t have to agree with you!

Look for everyday opportunities to put small invitations out into the world.

Real conversations often start by putting a single, small invitation out into the world and being ready to catch whatever comes back to you. Find ways to gently signal that you are interested and up for talking about these things. Then wait to see if others take you up on that.

• Share a book, an article, a quote, a website, a YouTube video, or a movie recommendation that raises issues about aging and dying with someone - and then ask them what they thought about it.

• When someone else talks about these issues - be ready to ask them more about it. Nudge a conversation with one extra question. Show that you really are interested in hearing more.

• Bring up aging and dying in the same way you might talk about other interests you have (e.g., mountain biking, knitting, fishing, or gardening). Tell people that this is something you are interested in/thinking about/dealing with. See what they ask you about it, or if they want to swap experiences. And it is also fine if they don’t follow up at all. Just normalising raising the topic is a really helpful thing to do.

Listen.

Worry less about what to say or how you will comfort, fix, or solve anything. Instead, just slow down and listen. Showing you are genuinely interested and that you will make the time for listening is one of the best ways we have found to start and deepen conversations. Say “tell me more”—even when what the person has said is hard to hear or something you disagree with. You don’t have to take on responsibility for making anyone feel better or solving all their problems or curing them. Just listen.

Deep listening is miraculous for both listener and speaker. When someone receives us with open-hearted, non-judging, intensely interested listening, our spirits expand.  Sue Thoele

Take it slow.

When we are nervous or unsure, it can be tempting to rush in. This might look like talking a lot, insisting that a conversation happens now, or trying to get all of your ideas, feelings, and views out in one big conversation. It is often better to slow down. Instead of thinking about one ‘big’, ‘serious’ conversation, imagine how you might have a small conversation: just one cup of coffee; just one question; seeing where that goes; doing it again a little while later. These conversations can unfold over years.

Make space. Hold this lightly.

People have told us that to start talking more they want:

• to be asked just a couple of questions - and then have lots of space for the conversation to go in any direction they want.

• to feel that you are not pushing or driving one way of thinking but neither are you withdrawing, hiding, or shutting down.

• a little bit of challenge, or some new ideas - but not too much at once

• to know that it is ok to go deep - but also have enough space for relief and lightness. It is SO ok to laugh (as well as cry).

• to be able to have a break - to go away for a while and revisit a conversation later.

Be ok with “no thank you” and “not now.”

It is absolutely fine to bring the topic up and have someone respond with “no thank you” or “not now.” It might not be the right time or place for them, or you might not be the right person - and that is ok. It was not wrong for you to give them the invitation, even if they say ‘no’. You can try to gently invite them into the conversation at a different time. Or keep looking for someone else (or a new group) who does want to have that conversation with you.

It’s not all words.

So much of the authenticity and care in a conversation is not in our words - but rather in how we show up and tend to the unspoken. Pause. Pour the tea. Breathe. Walk together. Sense what is happening. Notice the small gestures (yours and theirs). Feel how you are holding yourself and your body. Be aware of the time and space you are holding a conversation in. In the middle of the supermarket, or when everyone is tired, or you have had too much to drink - might not be the best time or space to start!

Do less telling and advising.

How much of the space in the conversations you are having is taken up by you? What could you do to push less hard, say less, ask more? When we are in ‘expert’ or ‘advice-giving’ mode, it is easier to swamp or overwhelm other people. Real conversations need space to share, explore, cry, and laugh together (rather than pushing to agree on neat, certain answers). Remember that it is okay to disagree; it is okay to be lost and confused together; it is okay to have lots of space for feelings (the happy ones and the sad ones). Be a friend, not a service provider. You don’t have to have any answers.

Be careful about being a comfort blanket.

Too often it is us - the loving children, the devoted spouse, the good friends - who are smothering real and important conversations that people want to have. We don’t want people to be suffering or sad - so we rush to advise, comfort, fix, and control. But this shuts things down. It doesn’t open them up. When we focus too much on comfort, we don’t make any space for messy, deep, real conversations. What many people want is space and time to talk about (and struggle with) all of it. Opening up means allowing people to have time to feel confused or sad, to talk through some crazy idea, to ask questions, to share their feelings and memories (the good ones and the not-so-good ones).

Beware of getting stuck in only one type of conversation.

How often are you only talking about funeral plans and legal documents? These are very important things. AND this ‘logistical stuff’ is often where conversations get stuck. There is a vital chunk of the conversation that is missing. The other things we need to be talking about are the relational, emotional, collective stuff. The awe, loneliness, joy, grief, forgiveness, fear, uncertainty, suffering, growth, and love. Talking about aging, illness, and dying is a heart space—not just a head space. One good way to get out of the logistics and into a heart space is to regularly have small conversations focused on saying ‘thank you’, ‘I love you’, ‘I am sorry’, ‘I forgive you’.

Say thank you.

It doesn’t matter how short your conversation has been or how well, awkward, or meaningful you feel it has been - try to say thank you. Your ‘thanks’ don’t have to be a big speech. It just needs to be true. Simple and short is great. And, if you feel up to it - in a quiet time after the conversation is over - you may also want to purposely thank yourself! Remember what you did well. Acknowledge your persistence and bravery in showing up in this space.

Saying thank you is more than good manners. It is good spirituality. Alfred Painter

Don’t be too hard on yourself.

Starting conversations about these things - and keeping them going - is not always easy. But it is deeply valuable. It won’t always work or feel good. That is not a problem. Take some time to think about what feels good and what doesn’t in the conversations you are practicing. But don’t hold this too tightly. Play with ideas, test things out, say sorry if you think you need to. Please remember that there is no ‘right’ or ‘wrong’ about this stuff. What matters most is showing up.

Remember that silence is full of suffering.

It is often easier to notice when what we have done or said has felt wrong or uncomfortable than to notice the suffering that is caused by our inaction or silence. Silence and avoidance might feel more comfortable—but often it is not kinder or better. People have told us that they felt more angry, lonely, confused, sad, disappointed, tired, desperate, and regretful when real conversations have NOT been had. We do need to talk with care. We do need to take time. We do need to listen and know when to stop (for now). But we need to also remind ourselves that silence can be deeply hurtful.

Trust the power of small actions to create unexpected ripples.

It might sometimes feel like what you are doing is ‘going nowhere’. In our experience, that is unlikely. We have been surprised over and over again by how very little conversations or actions have sparked ripples of small change that have a life of their own. You might not be in the middle of (or even see) the results of the small conversations you start. Let go of ‘seeing results.’ Just keep showing up and being real.

“Courage starts with showing up and letting ourselves be seen.
I think the people who wade into discomfort and vulnerability and tell the truth about their stories are the real badasses in this world.” Brené Brown