The Joy of Dying (Really)
Make the Last Conversation You Ever Have the BEST Conversation You Ever Have (And Have It Now)
Principle #1 of 9 in the Art of Encore Living series.
Several years ago, my wife and I sold the farm where we raised fruit, vegetables, chickens, pets, our two sons, and more than a few eyebrows. Our boys, now grown and gone, we moved to town.
Days later, I came within inches of being hit by a car on my morning run.
The irony was obvious. Just after selling the farm, I nearly bought the farm.
For years, our home had been at the end of a long dirt road. As I approached fifty, overweight and running on fumes, I decided to reclaim my health. What began as a mile-long walk turned into a five-mile daily run. I dropped seventy-five pounds and found a rhythm that steadied my life.
When we moved, I mapped out a new route through town, assuming that sidewalks and crosswalks would make it safe. That assumption nearly killed me.
I couldn’t imagine giving up running. It wasn’t just exercise. It was the ritual that cleared my head, anchored my identity, and gave structure to my days. But the close call was too close.
So, I drove to the cemetery to go for a run.
The cemetery sits on a hill overlooking the Blue Ridge Mountains. The paths wind through fruit trees, flower patches, and old tombstones, some dating back before the Civil War. Deer wander the perimeter. Cows graze beyond the fence. The air is still.
Running there changed everything.
Being surrounded by beauty and mortality at the same time is grounding. Each step is a reminder that life is a gift—temporary, fragile, and full of possibility if you decide to live it that way.
That run became a practice of memento mori—remember, you will die.
I didn’t adopt that phrase to be dramatic or morbid. I adopted it to stay awake.
Because that’s what death awareness really is: not an obsession with endings, but a way of seeing clearly what’s still possible and available.
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We all avoid that conversation.
Not only with others, but with ourselves.
We treat death like a rumor instead of a reality. We convince ourselves we have time: time to get serious about what matters, time to mend what’s broken, time to finally do the work we’re called to do.
But the truth is, we don’t know.
And that ignorance isn’t a threat. It’s an invitation.
If I could put one conversation on every calendar, it would be the one you have with your future self on your deathbed. Not because it’s comfortable, but because it’s clarifying.
What would that version of you thank you for?
What would they regret?
When I imagine mine, I don’t picture comfort or closure. I picture honesty. I want to meet that moment, having fully spent what I was given. I want no leftover gifts.
That’s the real conversation: not “What do I want to do with my life?” but “What will I wish I’d done when it’s almost over?”
The answers are rarely grand. But they are grounded.
You’ll wish you had forgiven sooner. Risked sooner. Created sooner.
You’ll wish you’d stopped waiting for certainty and started with sincerity.
You’ll wish you’d given your energy to what outlives you.
Your deathbed conversation isn’t about dying. It’s about deciding.
Every choice kills off a possible future. That’s what “decision” literally means—to cut away. Each day, you decide what lives through you and what dies with you.
The purpose of confronting death now isn’t to rehearse sorrow. It’s to sharpen purpose.
When you realize life is short, you stop putting things off. When you remember it’s precious, you stop pretending.
Memento mori isn’t meant to depress you. It’s meant to distill you—to strip away the trivia so you can spend your finite attention on what endures: character, contribution, connection.
And that brings us to vocation—the work your life is asking of you now.
The most important conversation you’ll ever have isn’t about dying. It’s about deciding.
If you’re ready to go deeper into how death awareness clarifies life, purpose, and vocation, keep reading.
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If the first half of life is about achievement, the second half is about alignment.
It’s the difference between living for validation and living from vocation.
Your encore isn’t about climbing higher. It’s about sinking deeper—into meaning, into service, into the work that feels like worship because it makes you whole while it serves others.
The cemetery taught me that legacy isn’t what you leave behind. It’s what you live out loud while you still can.
That’s the real art of encore living: treating every day as a limited edition and spending it accordingly.