7 Life and Death Questions

Michael Hebb, founder of Death Over Dinner, offers some important questions to guide your contemplation of mortality.

Michael Hebb
23 May 2024
Photo by Annie Spratt.

“In each life there are two lives, and the second one begins when we realize we only have one.”

This quote attributed to Confucius is one of my favorite bits of wisdom ever written about death. Its simple math illustrates poignantly the medicine present in contemplating our own mortality—the simple truth that facing death unlocks a much deeper, more vital life.

What do you want to be remembered for?

Rodney Smith wrote in Awake at the Bedside, “We end our suffering when we understand that we are diminished as human beings when any part of our character is denied.” And what we deny most in our death-phobic culture is the very fact that we die.

Journaling is a perfect way to explore our fears, anxieties, revelations, and grief about death. I recommend putting aside ten minutes every week to journal on this topic. Pick a day when you know you can sit quietly with your thoughts and let your pen make its way through this sometimes difficult terrain. Keep this journal separate from your others, because you will likely find yourself drawn back to it for answers as life inevitably serves up loss, terminal diagnosis, grief, and awakening.

Here are some of my favorite writing prompts you can use as you journal. They are inspired by the work of Dr. Ira Byock, Megan Devine, Ram Dass, Alua Arthur, Frank Ostaseski, and so many other remarkable teachers who have offered us their wisdom about facing our mortality. Don’t force a prompt—if it isn’t lighting up something in you, move on to the next. Most importantly, be gentle and kind with yourself as you explore this vast landscape.

• Have you been close to an end-of-life experience that you felt was beautiful? What was right about it?

• Have you been close to an end-of-life experience that was more difficult than you feel it had to be? What went wrong?

• If you found out you only had one hour left to live, who would you call and what would you tell them?

• What song(s) would you like performed at your funeral? Write about what each song means to you and why you think it would be meaningful in this context.

• If you died today what would be your biggest regret?

• “anger. is often grief that has been silent for too long.” Does this line from a poem by Nayyirah Waheed strike a chord within you? Is there a death or a grief that comes to mind?

• What do you want to be remembered for? Try writing a short obituary for yourself.

The great lesson I have learned through writing and talking about death is that our answers change as we age, evolve, and experience loss. It is a topic that will always reveal the invisible to us. It will show us ourselves.

Michael Hebb

Michael Hebb is the author of Let’s Talk About Death (Over Dinner) and the founder of Deathoverdinner.org and EOL.community, a comprehensive platform for end of life planning and grief.