How to Remember
My birthday is approaching. And this one is an important milestone.
I gave myself the summer to develop a five year vision for my life, as I enter a new decade and chapter. Not a rigid one. Not a plan. Something softer.
For much of my life, I’ve lived with a plan. For fifteen years, I led a company as CEO. I planned in quarters and years. That type of planning was tied to outcomes—concrete, prioritized, trackable. This is different.
The starting point for my five year vision surprised me. It wasn’t a question of what I want to build, achieve, or even who I want to become. It began with qualities. Ways of being. Not in the shape of my accomplishments, but in the shape of my presence. It is about how I move through life, regardless of when or where, or even why.
So I started making a list of qualities that are important to me. It came quite easily. Now I am working with my coach to sift through them to discover which ones are the most important to me right now, and relevant to this next chapter of my life.
In a recent conversation with my coach, we shifted from qualities to something else altogether. A prompt he gave me. A writing experiment I hadn’t expected: to write my own living obituary.
Had it come at any other time, I might have hesitated. But the timing made sense. I’d recently been reminded of the idea by Tuesdays with Morrie, a book that I read many years ago. In it, Morrie, a professor facing a terminal illness, hosts a living funeral. He wanted to hear what people will say about him before he dies. A subtle rebellion against a world that waits too long to speak honestly and lovingly.
And recently, my parents returned from the funeral of my aunt. When they spoke about the experience, they kept returning to one observation: how strange it is that we only seem to say these things after death. Why wait? they asked.
So when the prompt came to write my own obituary, I felt a surge of energy pass through me. I had to do it.
I’ve written every week for this blog for over ten years. I journal several times a week privately. I have written four books. Words are a home for me.
However, when it came to writing my living obituary, my page stayed blank.
It’s easy to write about an experience from within it. It’s harder to zoom out, to see myself from the outside. I didn’t know where to begin. Not because there was nothing to say, but because the exercise required looking at myself differently than I am used to. And maybe that was the point. Looking not out at the world, but across my life. Not forwards in time, but backwards.
After a few attempts, I found myself turning to one of my AI assistants, ChatGPT. I gave it a single line: “As part of a reflection exercise, and knowing what you know of me, I’d like your help writing a living obituary.” I wasn’t sure what, if anything, would emerge.
Six seconds later, a draft appeared.
And I sat back. And I read quietly and slowly about my life.
The words held a mix of familiarity and distance. They were about me, but not by me. There were facts about my life, but what surprised me was how present my hidden desires were embedded throughout. My hopes. My aspirations. My dreams. Not written in the usual future tense where they live in my journal and my mind, but in the past tense. As if they had already happened.
It changed something in me.
Sometimes, speaking about the future feels like building a story we may never enter. But reading that future as if it had already occurred, there was a strange intimacy in that. My ambitions felt less speculative, more lived. They felt, for a moment, like memories.
When I journal, there’s always a sense of reaching, into the unknown, toward something unformed. But here, the past tense created a kind of grounding I didn’t expect. A possibility dressed as remembrance.
Of course, the words weren’t perfect. They weren’t mine. But they gave me something to work with. A clay form. I’ve always enjoyed editing, and this now feels like that. A chance to shape. To soften. To reveal. And in doing so, not just to craft a better piece of writing—but to better understand myself in this moment in time. The prompt pointed not to the end of life, but to the center of it.
It reminded me of how powerful it is to pause and look, not forward or inward, but from the imagined edge, backwards. The things that feel vague become visible. What I’ve value begins to reflect back towards me with more light.
The obituary isn’t finished. And neither am I. But what emerged was clarity.
And that is how I learned to remember.
If you are curious to read it, simply reply to this email and I’ll send it to you.
