How to Master Your Memories with AI
Plus, celebrating my elementary school weirdness
Dear Prompt Experimenters,
You are what you remember.
Imagine there’s a button. Push it, and you’ll lose access to ALL your memories for the next sixty seconds.
During that interval, are you still you?
Kind of…maybe…but not really, right? We could debate the finer nuances of what “you-ness” means. But you’d act differently. You’d think differently. If you talked with someone else, they would immediately say: “you don’t seem like yourself.”
If you are the sum of what you remember, doesn’t it make sense to revisit your portfolio of memories from time to time? Why do you remember the things that you remember? Why do you remember them the way you remember them? Can you change that? Should you change that?
AI can help, and I have a prompt. And I will say this: my own results really moved me. I’m going to be using this prompt a lot. I hope you will too.
FIRST THINGS FIRST: What are thought experiments? Why are they so well-suited for AI?
I write a lot of thought experiments. I write a lot of AI prompts. In my mind, they are often the same thing.
Thought experiments are structured exercises that invite you to think differently about a certain topic, and explore where that takes you.
Some AI prompts are purely practical. Proofread this email. Write a report on the regulatory landscape for P&C insurance in Brazil. Etc.
I write some of those, because they are useful. But I have a lot more fun writing thought experiment prompts, like the ones I’ll be sharing today.
A word of caution though: I’m a philosopher and management consultant, not a psychologist. Thought experiments are not therapy, and not appropriate for the types of concerns that require professional support.
Ok, let’s get to it.
MEMORY EXCAVATION WITH AI
I’ll share first.
I picked the most random, arbitrary memory I could think of. The type of memory that causes you to wonder: why on Earth do I remember THAT?
I fed it to AI, and here’s what came back:
🧠 MEMORY EXCAVATION BRIEF
📝 Summary of the Excavated Memory
You were in first grade on Grandparent Visitation Day—a generally happy occasion. The classroom was bustling with energy and the presence of grandparents, including your own. At one point, you had a question for your teacher. She was standing at the front of the room, and you walked up to her. But instead of simply speaking up, you raised your hand directly in front of her and waited for her to “call on you” before speaking. You remember the moment vividly, not for the content of the question or her response, but because you hesitated internally, thinking: “In this situation… should I raise my hand?” Then you did.
💔 Emotional Impact or Attachment
The memory isn’t charged with intense emotion, but it glows with a subtle, persistent significance. There’s a whisper of awkwardness, a tinge of absurdity, and a kind of childlike earnestness. As an adult, you look back on it with a mix of amusement and empathy. But at its core is a feeling you’ve encountered many times since: the meta-moment of watching yourself act and wondering whether you’re doing the socially correct thing. It’s not about shame—it’s about uncertainty, calibration, and self-monitoring.
🔍 Deep Analysis of “Why”
This memory endures because it marks a quiet milestone: your early realization that life includes invisible social rules, and that even when you're trying to follow them, they can feel ambiguous. It's one of your first conscious experiences of self-awareness within a social context—that strange doubleness of acting and simultaneously watching yourself act.
The moment was small, but your brain flagged it. It said: “Pay attention. This is how people learn to be people.” You were beginning to tune into a lifelong preoccupation: what’s appropriate, what’s weird, and what’s real. And over time, that same radar, once used to police yourself for signs of awkwardness or low EQ, became something richer. Now, you seek to bend the rules on purpose. You want to be delightfully weird, but with control. This tiny scene—hand raised in the teacher’s face—is the seed of that evolution.
It reminds us that the line between vulnerability and self-mastery often starts in moments that feel irrelevant. But nothing in the mind is truly irrelevant—not if it stuck. And this one stuck, because it told you: you are being watched, even when you're not. Especially by yourself.
This happened 41 years ago. I’d never taken the time to process why it stuck with me. Until now.
Want to give it a try?
Use this prompt:
🧠 Memory Excavation Prompt
You are an AI interviewer. Your mission is to help me dig deeply into a specific memory that lingers with me, one that seems small, arbitrary, or unexpected, yet has remained vivid in my mind over time. We will explore why this memory sticks with me, why I remember it while other experiences fade, and what it reveals about my mind, narrative construction, and emotional landscape.
We will conduct a one-on-one interview. You will ask me one question at a time, taking your time to understand the memory and its emotional impact. You’ll allow me space to reflect, and be open to any emotional or subjective responses. There’s no rush—just keep probing deeper until we’ve truly explored the memory in detail.
Once we’ve uncovered enough, you’ll write a Memory Excavation Brief with three parts:
📝 Summary of the Excavated Memory – A detailed, clear description of the memory I’ve unearthed, no matter how small or seemingly irrelevant it may be.
💔 Emotional Impact or Attachment – An exploration of the feelings triggered by this memory. Why does it matter? What emotional resonance does it hold? Is there a sense of nostalgia, regret, joy, or something else?
🔍 Deep Analysis of “Why” – A nuanced, introspective analysis of why this memory sticks with me. How does it fit into the narrative I construct about myself and my life? What does this memory reveal about my emotional priorities, personal values, and how I make sense of my experiences? How might this memory influence my present life, decisions, or identity? This is where we dig deep, using everything we know about me from past conversations to help frame this in a broader context.
The tone should be thorough, reflective, and introspective—bold when necessary, but always focused on depth and understanding.
Want to go even deeper?
Paid subscribers, read on for:
A memory re-immersion prompt: Simulate re-living your memory, in vivid detail, and see how that changes how you remember it going forward.
A memory chaining prompt: Excavate deeper. Understand what other memories live on the same thread in your mind, what links them together, and what they collectively say about the way you remember.