The Gift of Difficult Conversations

The Dalai Lama is quoted as saying, “as a Buddhist, I view death as a normal process, a reality that I accept will occur as long as I remain in this earthly existence, knowing that I cannot escape it. I see no point in worrying about it. I tend to think of death as being like changing your clothes when they’re old or worn out rather than as some final end. Yet death is unpredictable. We do not know when or how it will take place. So, it is only sensible to take precautions before it actually happens.”

I want to repeat that. It is only sensible to take precautions before it actually happens. But many of us aren’t comfortable talking about death. Have you had that conversation with your significant other, with your children or your parents, or with friends or relatives if you’re a solo ager?  There are the practical things, like a DNR, living will, do you want cremation or burial, all that kind of stuff. But then there’s the other stuff, the deeper stuff, like, how do you want to be remembered? What’s your legacy? Are you afraid of dying? What do you want your final days to be like? Those are deeper conversations, and if you don’t have them, you leave your loved ones guessing as to what you might want.

Michael Hebb is the founder of which helps you host a facilitated dinner conversation with the important people in your life … about death.

Michael said “we’ve stopped viewing the table as a place where we come together to share ideas. We really don’t know how to eat together anymore.”

The ancient Greeks were great at gathering around a table and sharing ideas and knowing how to really take the most advantage of that time. Those conversations over dinner were called symposiums when they were official. You might have found Plato or Socrates or Aristophanes or Aeschylus or any of those principal players in the creation of Western civilization at a dinner table, talking about the nature of love or death or a relationship to the gods. And these conversations helped develop the ideas for democracy and our justice system. There’s a lot of power in gathering and talking over the table.

We are also deeply isolated, and we aren’t given a lot of tools for deep interpersonal connection. “We go to our therapist, we go on retreats, we do a lot of things that are not within our actual friend group that don’t strengthen the bonds within our family or our friend group. What I realized was that the most difficult conversations are the ones that we avoid, the ones that have the most potential for human connection, deep bonds, and to give us an opportunity to transform our perspective and live differently,” Michael stated.

Death is something that we all share and it’s something that many of us avoid and we consider the topic taboo.

Michael explained, “For me, it was deeply personal. My father was diagnosed with Alzheimer’s when I was in second grade, and he died when I was 13. His death had a huge impact on our family. It was the type of illness and death that actually fractured our whole family structure and our whole family tree, nuclear and extended. And still we’re trying to heal that. But a lot of blame and shame and miscommunication and misunderstanding happened.”

He saw the worst of it when a family doesn’t have the tools and doesn’t take the time to talk about terminal illness, eventual death, how to honor somebody, and what to do with their stuff.

Michael believes that one of the reasons our health care system is bankrupt is because we don’t talk about death. “We spend something like 70% of health care expense in the last two years of life. It’s the number one cause of personal bankruptcy in the United States, the end-of-life expense for a loved one. So, it’s bankrupting us. It’s bankrupting the system. And it’s avoidable. We can have a conversation about how we want to be taken care of in our final days.”

Getting people gathered to talk about end of life can be uncomfortable and challenging. The people you want to gather are the people who are most important to you. Your spouse, your parents, your children, maybe your best friend.

Explain to them that it would mean a lot to you to have this conversation with them. You love them and you want to make sure that they understand how you want to be cared for at the end of your life, and you want to know how they would want to be cared for also. And realize that ultimately, it is a gift to your family to have these conversations.

Michael stated, “It has always been the case that turning to face our mortality is the thing that gives us the most clarity, vitality, sense of purpose. I think Confucius said it best when he said, in each life there are two lives. And the second one begins when you realize you only have one.”

Some of the takeaways from my conversation with Michael Hebb, founder of include

  • Don’t be discouraged when your loved ones give you resistance to a conversation about death or really any difficult conversation, but especially about death.
  • End of life medical care can bankrupt you. Being prepared for how you want to be cared for can help prevent this type of bankruptcy.
  • The most difficult conversations are the ones that we avoid, the ones that have the most potential for human connection, deep bonds, and to give us an opportunity to transform our perspective and live differently.

If you are interested in the full show with Michael Hebb,

Listen on Apple podcast or Spotify or watch on YouTube.

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