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 such an awful thing. Why couldn’t I have said I was so, so sorry? Why couldn’t I admit my mistakes? Why did I waste so much time staying? Why didn’t I leave sooner? Why didn’t I get help? Why didn’t I see the signs? Those red flags were flapping in my face. If only I had done such-and-such. If only I hadn’t done such-and-such at all. Why did I make such an egregious decision or choose that particular path? Why didn’t I know myself better? Why? Why? Why?

As a former hospice chaplain, I posted sentry at hundreds of deathbeds and listened to a life span of litanies from patients about regret. We all live with regrets; regrets go hand-in-hand with life. Some are only passing qualms with momentary hand-wringing or a pinprick of conscience while others weigh us down with shame and culpability. Hopefully, we learn through our mistakes, feel remorse, and ask for forgiveness. Or we back up and reconfigure our journey. We walk toward the road that diverges. We become discerning and more prudent through aging and its challenging experiences. We are transformed into Sages.

But if we wait to examine our lives until the very end, there is nothing we can do but try to make amends the best we can and forgive ourselves of the catalogue of our transgressions. But why live a life that accumulates piles of guilt? And not everyone is blessed with a death preceded by a lingering illness with hours to reflect on misgivings and their consequences. And not everyone reaches senior citizenship at 62 or clinches the last stage of the elder years at 80. If we can live in the present moment, accept reality, and grow in self-awareness, we can decrease our sorrows stemming from the running-regret-meter. Why leave for tomorrow, what we can spiritually address today?

Age does not equate to wisdom. We often receive foolish advice from an older person and wise advice from a youth. In fact, Franciscan Priest Richard Rohr in his book, “Falling Upward” describes the path toward spiritual maturity. He states that approximately 60% of folks go to their graves as “first-half-of-lifers.” In other words, most people never achieve a ‘second-half-of-life” maturity: a whole-adult perspective, a keen self-awareness, and a compassionate worldview. That perhaps may explain the mess we have in our country today. Many of my dying patients struggled with the impression they were leaving on their families and community. They questioned their own integrity.

So the lessons from deathbed confessions and hand-wringing are to begin our inner work much earlier; the natural juncture for its commencement is usually in one’s late forties or early fifties. Some souls begin sooner which is why they might have problems fitting in with their own age group. If we do our inner work sooner, we have less emotional and spiritual baggage to wade through at the end of our lives. We need to leave it “all on the court” in this world. Why do the work here? Can’t we just wait a bit and do it in the next life? No, because we bring to the next life who we made of ourselves in this life.

I decided to write on this topic after reading an article in the Milwaukee Journal Sentinel about a woman from Madison who died on February 24th, 2021. It was a poignant, but also somewhat humorous article and made the point quite well about leaving regrets on the “court” upon dying. “Carol had been a mother who raised her children to avoid certain topics–like politics, religion, and money–in mixed company. The article didn’t specify if it was alright to discuss these sensitive topics in only a single-gender gathering. But then at the end of her life, Carol had some regrets about just how polite she had been about important issues. Her conscience was piqued when she heard Senator Ron Johnson of Wisconsin speak during the Senate hearing about the January 6th riot at the U.S. Capitol. She said, “she wished she had spoken up more and done more.” She felt Johnson was “totally white-washing what happened on January 6th.”

The article went on to say that the night the family had watched the event on Capitol Hill was the last time they saw their mother alive. Carol, age 81 died in her sleep the next morning. Her obituary celebrated her love for “her children, grandchildren, her cat, books, friends, politics, and Chardonnay.” It also noted her opinion of Johnson: “In lieu of flowers, please make a donation to Ron Johnson’s opponent in 2022.” She told her children the night before her unexpected death that she “wished she had been more involved and outspoken about her convictions.” Instead, the family honored her wishes in her obituary.

We think we have time to “get to it,” to “take care of business,” to “leave it all on the court” and then time runs out as it did for Carol. Like it does for all of us. What legacy do you want to leave? What spiritual and emotional heirlooms would you like to leave for your family, friends, neighborhood, community, city, and world? What kind of impactful and inspirational life do you want to manifest? Legacy planning takes time. Now is the watershed moment to reflect on and create a life you’re proud to bestow upon your loved ones and those who witness your choices. Now is the time to prepare for that ritual your family will hold for you as you pass to the next life.

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