On personal CRMs, a bus driving away, and what we lose when we outsource the work of remembering
This past weekend my son left on a bus for the state track finals. My wife asked if I’d record the send-off. The parents gathered, the bus pulling away. So I pulled out my phone and hit record.
I didn’t see my son’s face. I was staring at my screen, framing the shot, making sure I had it. He was somewhere in that scene and I missed him entirely. Not because I was distracted. Because I was trying to do something thoughtful and the tool required all of my attention to use.
I realized it in the moment. And I’ve been sitting with it since.
Several years ago, I built a personal CRM. Not for clients, for my relationships. Friends, family, people I cared about. I recorded details from conversations. Birthdays, anniversaries, things people had mentioned that I wanted to remember. I even made a video about it because I thought others might find it useful.
The motive was genuine. I wanted to remember things because I cared about people. I wanted to be the kind of person who follows up, who remembers, who shows up in the small ways that matter. The system was an attempt to be more present, not less.
But here’s what I eventually realized: I never went back to it. I’d enter something and file it away and then forget it existed until I happened to go looking for something else. The information was stored. It was never remembered. And those are completely different things.
Storage without retrieval isn’t memory. It’s a filing cabinet you never open because of friction.
I’ve spent close to twenty years chasing tools that would help me remember more. GTD frameworks, Notion databases, AI-assisted capture systems. Every iteration came from the same place, a genuine desire to care well about more people and more things than my natural memory could hold. But somewhere in that chase I started confusing the filing with the caring.
Think about getting a birthday card from someone you’ve done business with. It’s a nice gesture. But you know and can feel that your birthdate lives in a CRM somewhere, that a reminder fired, that this card went out to everyone on the list. It’s not nothing. But it’s not the same as a friend who just thought of you.
The friend who remembers your birthday without a system remembers it because you cross their mind. Because they think about you when you’re not in front of them. Because you matter enough to occupy a small corner of their attention on an ordinary Tuesday. No tool produced that. Caring did.
That kind of remembering isn’t scalable. You can only genuinely hold so many people in your mind at once. Which means you have to choose, and the choosing itself is an act of caring.
I’ve been thinking about what I actually want. Not the system that helps me never forget anything. Not the AI tool that captures everything in real time. Not the second brain that holds all the context so I never miss a detail.
I want to remember my son’s face on the day the bus drove away. I want to think of a friend on his anniversary because I care enough that it comes to mind. I want to write something down by hand and see it again that evening and again at the end of the week until it becomes part of me rather than part of a database.
That’s less. And it’s enough. Because the things worth remembering aren’t the ones that fit in a filing cabinet. They’re the ones that live in you because you let them.
Is there something you’ve outsourced to a tool that you wish you still carried yourself?
Reply and tell me. I’m genuinely asking.
