Obituaries & Other Love Letters
Speaking of Death in Ways That Break Cycles and Build Connection
Death is one of my earliest memories. Death and unanswered prayer. Death and darkness. Death and cigarette smoke. There was an accident that happened beneath a towering pecan tree. In the swarm of panic that ensued, my mother lined us up along the sofa and said, “Pray.” So I prayed. Very hard. Using all the words a six year old could muster. But my sister died anyway. This month is the 44th anniversary of her death.
When I die, they tell me I will see her again. In my mind she remains a two year old running through the family room calling for me. I, on the other hand, left that child who knelt by the sofa and prayed a futile prayer, long ago.
Somewhere before or after the accident was the death of trust. When a cousin gave me a small stuffed animal in exchange for his pleasure. After the accident—but merely by days—was the death of safety. When an uncle who smelled of cigarette smoke slunk into the darkness and “comforted” me the way no child should be comforted.
When I die, I will go to heaven. When my uncle died, it was snowing and I was 697 miles away from his darkness. I poured champagne and toasted his passing without even considering attending his funeral.
By the time I was seven, I attended a second funeral. My grandmother of whom I had no memory. I had no recollection of ever meeting her. Most of the time, I hid in a closet with my cousins. It was hot and everything was soaked in sweat and tears and snot.
When I die, maybe it will be in the winter. But if not, my funeral will be air conditioned. I will make sure there are tissue boxes everywhere.
My father was a minister and my mother a nurse and for those reasons, death was part of everyday life. Someone was always dying—by accident or age. Sometimes by choice. Most times not. Because my parents were in the business of ministry, so was I. I escaped the sweat and tears and snot by providing musical accompaniment to the grieving. My ability to carry a tune rescued me from drowning in the sorrows of others.
When I die, I will choose the playlist. I have a running spotify list already that I occasionally edit. It has Willie Nelson and the Wailing Jennies and a stunning rendition of Shenandoah on it. For now.
In high school, a dear friend was driving too fast on a winding road and drove herself right up to heaven's gates. At her funeral, it was impossible to breathe. Friends stood shoulder to shoulder, lined the walls, spilled onto the front portico. We clung to each other so tightly that I still remember the feel of their arms around me. A year later, in another town and in another school, a boy I had a crush on committed suicide. Except it was the summer time, and I didn’t know anyone well enough to be remembered in the sharing of the news. So he died and there was a funeral I didn’t attend and someone mentioned it to me in passing in WalMart one afternoon. They walked away and I stood alone in the shampoo aisle and tried not to vomit.
When I die, there will be a party. I’ll write my own obituary. I’ve taken care of the memorial options on my social media. So that everyone I love and anyone who loved me will know and can lean into each other.
My mother’s family. A sprawling southern family encapsulated in smoke and alcohol started dying when I was a teenager. They kept dying, one by one, until the last one took his last breath when I was in my forties. I sang at most of their funerals. Or played the piano. My dad gave the eulogy. The truth of my uncles was never mentioned. My aunts were canonized for what they endured.
When I die, I will haunt anyone who even suggests playing a hymn. Especially if it’s “In the Garden.” And please don’t lie. I’m not always nice (though I do try).
By my thirties, I thought I understood death and that I was immune to its emotional talon. The death that came then left me stumbling in the dark for a long while. Cancer of an unknown source took a beloved friend. One who was a much better human than me. I knelt alone in the church at her casket for some time and wondered what sort of God is rolling the dice up there?
When I die, cremate me and sprinkle my ashes into the harbor I’ve grown to love. Please don’t bind me to a church or a religion or a slab of marble in a gated community of the soon to be forgotten.
It was after the untimely death of my friend that I read How to Die: An Ancient Guide to the End of Life. It's an old text written by the philosopher Seneca about sixty years after the death of Christ. It shifted everything for me. In it, he writes:
“Whoever doesn’t want to die, doesn’t want to live. Life is granted with death as its limitation; it’s the universal endpoint. To fear it is madness, since fear is for things we’re unsure of, certainties are merely awaited.”
Why such a dark post this week? It sprouted itself from last week’s post on how to connect to adult children. Tip no.8: Never Lead with “When I die…” That tip led to a handful of conversations with various friends. Fantastic conversations. And in the end I realized how heavy those three little words actually are.
When. I. Die.
It is my argument that these three words deserve the same care as those other three little words— I love you. In fact, they should be tangled together so you never say one without considering the other. If you say to someone: When I die, you’ll be sorry. Or When I die, you’ll do better… or you’ll figure it out… or you’ll realize what you’ve lost. Substitute it so that you can truly hear what you are saying.
Say— I love you and I want you to be sorry you love me. I love you and I want you to suffer from regret or ignorance or loss. Say it out loud. Feel what it does.
Because every time we use “when I die” to cast guilt, what we’re really saying is: I love you, and I hope it hurts.
Abiding, honest love strives to do no harm.
When I die, I want to leave behind wisdom and music and truth and a legacy of curiosity. How can I possibly say to my children, my family and my friends: when I die, I hope to leave you with all my pain and regret? I hope you carry forward the weight of my sorrow.
And what an arrogance. Hmm? To assume we have any concept of who leaves this world before another. Children die. Peers die. Parents die. No one is immune to this fate.
What if a child turns to you and says: when I die, I hope you regret it. Or maybe I’ll live long enough to show up at your 70th birthday. Or maybe I’ll see you at the holidays. Who knows? Maybe I’ll be dead by then.
Feel that? Even written here, it carries an awful weight. Those three little words can easily become weapons of emotional manipulation that damage relationships rather than nurturing them.
Seneca continues: There is only one way we can say that the life we have lived is long: if it's enough. … there’s no difference between the longest and the shortest life, if you survey how long a person lived and compare it with how long he (was alive) but didn’t live.
So how do we make sure when I die becomes a phrase that builds relationships, instead of harming them?
Make a will, no matter your age.
Share how you’d like to be remembered—put it in writing.
Talk to the people you love about what you want them to know or keep or cherish. Do it seriously. Do it with humor. Just do it.
If you’re feeling brave and philosophical, ask them what they fear the most about a world without you. Listen and offer assurances of how your presence will remain with them. Or, if this conversation is overwhelming, consider ways you can leave behind a sense of presence that you know will resonate. My friend who passed left birthday cards for her children and personal letters to open on significant occasions.
Here’s the big one: deal with your own baggage. Not just the basement boxes, but your regrets, your pain, your sorrow. Don’t pass them down like unwanted and broken family heirlooms.
Do these things, and when I die transforms from threat to promise. It becomes a relationship-builder: When I die, you will be cared for. When I die, you will know what was important to me. When I die, I will have left our little world better for you. When I die, I hope you find I cleared out some of the baggage so you don’t have to. When I die, you will know I love you.
When navigating family relationships, choose words with care. Make “When I die” a promise of love and clarity, not a threat of guilt or regret. By talking honestly about what matters, we can break old patterns, lighten the load for the next generation, and leave behind something far more lasting than grief and regret. We can leave behind understanding, connection, and peace.
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