This is the final week of Phase II — ten weeks of the topics that actually show up in second-chapter life. And this week is the one I’ve been thinking about the most.
There is probably a conversation you’ve been putting off. Maybe for months. Maybe for years. You know what it is. You know who it needs to happen with. And you know, somewhere in the back of your mind, that the longer it doesn’t happen the heavier it gets.
I want to be honest about what AI can and cannot do here. It cannot have the conversation for you. It cannot guarantee the other person will respond the way you hope. What it can do is help you figure out what you actually want to say — and give you the words to start.
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The 4 prompts from this week’s Sunday video
📌 Prompt 1 — Money and Inheritance
“I need to prepare for a conversation with [family member or group] about [money and inheritance / the estate / what happens to the house / dividing assets]. I have been putting this off because: [describe what makes it hard]. Please help me: (1) Think through what I actually want them to understand — not just the practical information, but the intention behind it, (2) Anticipate the reactions that worry me most and help me think about how to respond, (3) Find language for the parts that feel impossible to say directly, (4) Think about the right setting and timing for this conversation, (5) Decide what I want to have in writing versus what should stay in conversation.”
Use for: preparing the layer beneath the practical — what you want them to understand, not just to know
📌 Prompt 2 — Care Preferences and End-of-Life Wishes
“I need to have a conversation with [family members] about my care preferences and what I want if I’m no longer able to speak for myself. I’ve been putting this off because [describe what makes it hard]. Please help me: (1) Think through what I actually want — my preferences for medical intervention, living situation, who makes decisions, what matters most to me about how I live in my final years, (2) Find language that lets me start this conversation without it feeling like a crisis or a farewell, (3) Anticipate the reactions from my family members and how to respond if they resist or get upset, (4) Think about what should be formally documented and how to raise that without derailing the conversation, (5) Give me an opening sentence I could actually say out loud to start this conversation.”
Use for: protecting the people you love from having to guess in the worst moments of their lives
📌 Prompt 3 — The Estrangement or Old Wound
“There is a relationship in my family that has been damaged by [describe in as much or as little detail as you’re comfortable with]. I have been avoiding addressing it because [describe what makes it feel impossible]. Please help me: (1) Think about what I actually want from this — reconciliation, acknowledgment, closure, to say something before it’s too late, or something else, (2) Decide whether reaching out is right for me right now, (3) If I decide to reach out, help me write an opening message that is honest without being aggressive and that invites a response without demanding one, (4) Prepare for the possibility that they don’t respond or respond badly, (5) Think about what I want to have done regardless of how they respond.”
Use for: the relationship that has needed attention for longer than you want to admit — your part, done with care
📌 Prompt 4 — What I Want You to Know
“I want to tell [specific person or people] what I want them to know — not the practical things, the real things. I’ve been putting this off because [describe what makes it feel too hard or too vulnerable]. Please help me: (1) Think about what I most want this person to know — if I could communicate one thing, what would it be, (2) Help me find language for what feels too big or too raw to say directly, (3) Decide whether this should be a conversation, a letter, a recorded message, or something else, (4) Write me a beginning — the first few sentences I could actually say or write, (5) Think through whether there is anything I’m afraid to say that I would regret not saying.”
Use for: the extraordinary things we carry in our hearts that need to get out — the real things, not the practical ones
🎬 Watch Sunday’s video for the full walkthrough of all four prompts.
👉Sunday: How I Use AI to Prepare for the Conversations I’ve Been Putting Off
Now I want to hear from you. You don’t have to tell me what the conversation is. You can just say “I know what mine is.” Hit reply — that’s enough. I’ll know what you mean. 🐾
— Debbie
AI Puppy Playbook · aipuppyplaybook.com
I know what mine is, unfortunately. Though if I'm being honest, part of me worries that using AI to prep for something this raw is going to make it sound too rehearsed. Still, Prompt 2 gives a decent framework for not making it sound like a total crisis.