The Letter You Haven't Written
What would you put on the page if you knew time was short?
“How lucky I am to have something that makes saying goodbye so hard.”
— A.A. Milne
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The Letter You Haven’t Written
Earlier this spring marked 22 years since Pat Tillman was killed in Afghanistan. He walked away from a multimillion-dollar NFL contract to enlist after 9/11. If you’re not familiar with Tillman’s story, that tells you most of what you need to know about him. Before he shipped out for his final deployment, he quietly placed a sealed letter on the dresser for his wife, Marie. Left there with the hope she’d never have reason to open it.
He called it a “just in case” letter.
It’s a sobering and remarkable story. Not because the idea is sad, although it is, rather because of what that kind of letter forces a person to do. It filters through everything that doesn’t matter and leaves you staring at what does.
It’s a question for all of us — especially this Memorial Day weekend.
If you had to write that letter tonight, what would make it onto that page?
I don’t mean what sounds right. Not the things we rehearse when someone puts a microphone in front of us. I mean what’s true. When time feels short, even hypothetically, we get serious and we get real. We don’t talk about our possessions, titles, or impressive exploits that fill our days.
We get clarity and we think about people — our relationships — and what difference we’ve made in this world.
Who would you write your letter to? Your spouse, kids, a parent, or a friend? When you think of that person, what would you want to tell them?
My guess is it wouldn’t be a list of your accomplishments. Most think to how they helped others and how they made others feel. Whether we showed up. Whether the people closest to us knew that they mattered. No matter the level of success, in the end it’s not about being remembered for what we achieved.
And if that’s true, it raises a harder question than the letter itself.
If you already know what matters most ... what are you waiting for?
We operate on a quiet assumption that the people we love can feel our intentions even when we don’t say them. That our presence does the work our words never quite get around to. Maybe it does. But there’s something a letter does that presence alone cannot. It says: I thought about you on purpose and wrote these words. I wanted you to have them. That lands differently and the people who hear it feel the difference.
When I imagine writing mine, I still don’t know how I’d fill the page. I’m still working on that. But I do know I will start with what I’ve been given — the people and the moments with them. I think about the people who believed in me before I could see it in myself. About what I’ve wanted them to know and kept meaning to say.
The clarity that feels reserved for life’s most urgent moments is already available to us. We don’t need a tragedy or a diagnosis or a deployment to find it. We just have to stop assuming tomorrow is guaranteed and start treating today’s ordinary conversations like they might be the ones that matter most.
Maybe the exercise isn’t really about the letter at all. Think of it as an honest accounting of what matters, who matters, and what's still left unsaid. What would yours reveal?
The men and women we honor this weekend understood something about time that most of us are still learning. They made their choices — about service, about sacrifice, about what was worth everything — with full knowledge that tomorrow wasn’t promised. The least we can do is take that seriously.
Your legacy isn’t sealed at some distant finish line; it’s being written right now, in the conversations you choose to have and the ones you keep postponing. In the people you prioritize.
Who deserves to hear that they matter, that you care about them, or that you are grateful for them? Write the letter before it’s too late.
“What we have once enjoyed deeply we can never lose. All that we love deeply becomes a part of us.”
— Helen Keller
Connecting this quote to the story. The words we share and the love we express continue to live inside others long after we're gone.
This week’s Chasing Influence tip: Don't assume people know how much they matter to you, tell them while you still can.