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The Ultimate Conversation

How to Die Well
Death is what makes life worth living. It’s true. Death gives life a deadline. It gives a timeframe to do what truly matters in life.

Life and death are a package deal. We cannot separate them. Yet, we rarely give much thought to our own death until it is upon us. As a result, we don’t have the ultimate conversations as to how we would like our last days to be.

I learned a lot of things in grad school, but mortality was not one of them. My classes had nothing on aging or dying. Yet, death has been with me since I was born. I’ve been curious about it for decades. I know it’s inevitable and yet I live as if it is distant and something that happens to others.

The Paradox of Death
The paradox of death is that it points to what it means to be truly alive. Death is not waiting for us at the end of a long journey. The possibility of death is always with us. She is the secret teacher hiding in plain sight. She helps us to discover what matters most. She reminds us, like the Benedictine’s teach us: “Keep death daily before your eyes.”

Death, of course, is not a failure. Death is normal. We don’t want to experience loss and pain. But, as I have observed in others, facing death squarely can enable us to clarify our sense of purpose and thus, paradoxically, feel more alive, even at the very end of life.

Over the past years, I have sat on the precipice of death with a number of friends and had the profound privilege of having an ultimate conversation with each of them. I’ve learned a lot from them.

Three Ultimate Questions
I’ve learned that an honest discussion about death is perhaps the most important conversation of all. My co-author David Shapiro and I call it The Ultimate Conversation. There are no doubt as many ways to have this conversation as there are people to have it. We have found, though, that three big questions can be remarkably effective in fostering The Ultimate Conversation:

  • What do you think happens when you die?
  • How would you like to die?
  • What gifts do you want to leave the world before you die?

As friends and coauthors, we, Richard and Dave, committed to having The Ultimate Conversation as a way to end our book – Who Do You Want to Be When You Grow Old? We reflected on the three questions about death and did our best to answer them honestly and forthrightly. In doing so, we learned much about each other, but even more about ourselves.

We encourage you to have an Ultimate Conversation of your own with friends or family members. Doing so really can be a matter of life or death.

Here are my answers to the three questions. (You can read David’s answers in the book, pp. 125-128.)

What do you think happens when you die?

The idea of reincarnation has always fascinated me. Not the idea of dying and then coming back – a butterfly in the next life, for instance. But the idea of the cycles of life. I believe that a loving Creator created me (and you) to “grow and give” in a mysterious world. My next life might be revealed to me by our Creator… but probably not.

Gandhi once said, “All life is one.” He might have said it to unite a spiritually diverse world, but I subscribe to that view literally. When my body goes, when my thought ceases, the “All” remains. I’m part of the “All” of life, and life will continue, so I will too, in some new, mysterious form.

How would you like to die?

Viktor Frankl’s insight that enduring suffering could provide purpose in life was a major eye-opener for me. Bearing suffering with grace and courage might be a purpose in itself. That said, I don’t want to die; but more clearly, I don’t want to suffer. Will I still be writing a decade from now? I hope so, but who can say? What I do know is that I’m already looking forward to another book!

Sure, I could get charged by a young bull elephant in the bush in Tanzania, then buried right there, under a baobab tree. That’s a scenario I could live – that is, die – with. But, a more likely scenario that I prefer is to die sitting up and appreciating small pleasures like seeing a favorite bird outside our window while sharing a nice glass of red wine and exchanging hugs with my wife, Sally. These small pleasures will be enough to feed my soul up to my last breath.

What gifts do you want to leave the world before you die?

What survives me is my impact on others – one person at a time, one day at a time, every day of my life. My gift is simply to make a positive difference in one person’s life, every day. When I die, I hope that my epitaph will read, “Always on purpose.”

Our Ultimate Conversation has turned out to be an impetus for deeper reflections and has helped David and me see more clearly how death can teach us about the path of purposeful aging. We’ve come to understand even better how purpose is a fundamental motivating force for all humanity. It brings a wholeness to who we are, a sense of meaning to what we do, and a deeper connection to all life around us.


Richard Leider, founder of Inventure – The Purpose Company, is the author of eleven books, including three best sellers, which have sold over one million copies. Repacking Your Bags and The Power of Purpose are considered classics in the personal growth field.  Richard’s PBS Special – The Power of Purpose – was viewed by millions of people across the U.S.  His newest book, Who Do You Want to Be When You Grow Old?: The Path of Purposeful Aging is now available.

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