“Why Wait Until the End? How to Confront Regret and Build a Legacy Now”
“Lessons from Deathbeds on Living Fully, Letting Go of Guilt, and Leaving an Impact”
“If only I had done such-and-such sooner. If only I hadn’t done such-and-such at all. If only I hadn’t said that awful thing. Why couldn’t I admit my mistakes? Why did I waste so much time staying? Why didn’t I leave sooner?”
Sound familiar? These are the refrains I’ve heard countless times as a hospice chaplain—posted at hundreds of deathbeds, listening to a lifetime of litanies about regret.
We all live with regrets. They’re part of being human. Some are fleeting—momentary pangs of conscience. Others weigh us down like stones, heavy with shame and culpability.
The question is: Do we wait until the very end to deal with them? Or do we start now?
The Nature of Regret
Regret often comes in waves:
- Why didn’t I get help?
- Why didn’t I see the signs?
- Why did I make that choice?
- Why didn’t I know myself better?
The truth is, age doesn’t automatically bring wisdom. Franciscan priest Richard Rohr, in his book Falling Upward, says about 60% of people go to their graves as “first-half-of-lifers.” They never reach that deeper maturity—the whole-adult perspective, keen self-awareness, and compassionate worldview that marks the “second half of life.”
That might explain why so many of my patients wrestled with the impression they were leaving behind. They questioned their integrity, their impact, their legacy.
Why Start Inner Work Now?
If we wait until the end, there’s little time to do more than make amends and forgive ourselves. But why live a life that accumulates piles of guilt? Not everyone gets the luxury of a lingering illness with time to reflect.
The natural juncture for inner work? Usually late 40s or early 50s. Some start earlier—and often feel out of step with their peers. But the sooner we begin, the lighter our emotional and spiritual baggage will be when the end comes.
A Story That Says It All
I was inspired to write this after reading a poignant—and slightly humorous—story in the Milwaukee Journal Sentinel about Carol, an 81-year-old woman from Madison.
Carol raised her children to avoid certain topics—politics, religion, money—in mixed company. But near the end of her life, she regretted being so polite about important issues. After hearing Senator Ron Johnson speak during the January 6 hearings, she told her family she wished she had spoken up more and done more.
That night was the last time her family saw her alive. She died in her sleep the next morning. Her obituary honored her love for family, friends, books, politics, and Chardonnay—and her final wish: to have been more outspoken about her convictions.
Carol thought she had time. We all do. Until we don’t.
What Legacy Will You Leave?
What spiritual and emotional heirlooms do you want to pass on? What kind of life do you want to manifest for your family, your community, and the world?
Legacy planning takes time. Now is the watershed moment. Reflect. Create a life you’re proud to bestow. Prepare for that ritual your family will hold when you pass to the next life.
Because we bring to the next life who we made of ourselves in this one.
Your Turn
What regrets are you carrying? What inner work have you postponed? What legacy do you want to leave?
Start today. Leave it all on the court.
Marc D Malamud
Transitioning Doula
