Everything I know lives only in me — and I'm finally doing something about it 🐾
The career wisdom I never wrote down. The family stories only I can still tell. The life lessons I've been meaning to pass on. Four AI conversations that are helping me get it all out.
After three weeks of going into some genuinely hard territory — email exhaustion, retirement identity, memory worry — I want to take a breath this week and turn toward something I find genuinely exciting.
This week is about what you know. Not facts you learned — the real knowledge. The kind that took decades to build. The kind that lives only in you.
🐾 · · · 🐾
The reframe that started this for me
A few years ago I was talking to a colleague who had just lost her mother. She was going through her mother’s belongings and kept coming across evidence of a life she hadn’t fully known — letters from a professional life her mother had left behind, notes from a period of difficulty her mother had never talked about directly, a small journal from the first years of her marriage that contained the sharpest and funniest observations her mother had ever written.
“She was funnier than I knew,” my colleague said. “She was more complicated than I knew. And now I’ll never be able to ask her about any of it.”
That conversation changed how I thought about what I was holding. Not as things to do one day. As gifts I hadn’t given yet.
🐾 · · · 🐾
What I’ve started capturing
I’ve been using AI as an interviewer for my own knowledge — and the process has been more surprising than I expected. I thought I knew roughly what I knew. I didn’t. The AI interview sessions surfaced things I’d completely forgotten I knew. Judgment calls from early in my career that I’d integrated so deeply I’d stopped thinking of them as learned. Family stories I hadn’t thought about in years that came back with unexpected vividness when the right question arrived. Life lessons I’d never fully articulated that turned out to be more specifically mine than I’d realized.
None of it was on paper. All of it is now being captured — slowly, in sessions, organized session by session into something that will outlast the session.
🎬 Watch Sunday’s video: Four AI conversations for capturing the career knowledge, family stories, life lessons, and shaping them into something worth keeping.
⬇️ ALL 4 CAPTURE PROMPTS FROM SUNDAY’S VIDEO ⬇️
📌 Prompt 1 — Career Knowledge Nobody Wrote Down
"Please interview me about the professional knowledge I've built through experience. Ask one question at a time about: the most important lesson my career taught me that I couldn't have read in a book, what I learned about my field that took years to understand, a mistake I made early that I'd never make again and why, and what I would tell someone starting in my field today that they won't hear anywhere else. Help me go deeper than the surface with each answer."
📌 Prompt 2 — Family Stories Only I Can Still Tell
"Help me identify and capture family stories that might otherwise be lost. First ask me: who in my family history do I know the most about that younger generations know the least? What family events shaped everything that came after? What stories do I find myself telling that nobody else can tell? Then interview me about each story — asking what was happening in the world then, what they wanted, what they sacrificed, what they'd want their descendants to know."
📌 Prompt 3 — Life Lessons Worth Passing On
"Interview me about the life lessons I've learned — not generic advice but what I know from having lived. Ask one at a time about: what I know about [relationships / money / work / loss] that I couldn't have known at thirty, the hardest thing I've been through and what it taught me, what I'd do differently and what I'd do exactly the same, and what I most want the people I love to understand that I've never fully said."
📌 Prompt 4 — Shape It Into Something Worth Keeping
"I've captured some [career knowledge / family stories / life lessons] and want to shape it into something shareable. Here's the material: [paste or summarize]. Please help me turn this into [a letter to my younger self / a family history document organized as stories / a one-page personal credo / a wisdom letter to a specific person]. Keep my voice. Add shape. Make it something worth keeping."
Here’s what I want to know: what knowledge do you carry that the people around you don’t fully know about? A professional expertise. A family story. Something you learned the hard way. Hit reply and tell me — one sentence or several. I’m reading every one. 🐾
— Debbie
AI Puppy Playbook


