Ten years from now, which choice will I wish I had made?
A look back from the future at each option: what you’d regret, and which regrets you could repair.
- When to use
- When the practical arguments are even and the choice is really about the life you want.
- Time
- 10 min
The prompt
I’m deciding between and . Help me look at it from further away. Ask me up to four questions, one at a time, about what I’ve regretted before, what I’m proud of having done, and who is affected either way. Then, for each option, describe what I’d most likely regret one year out and ten years out. Say which of those regrets I could repair later and which I couldn’t. End with which option the ten-year view favors and how confident you are. Regret is hard to predict and you barely know me, so say so where it applies. Don’t assume the bolder option is the one I’d regret missing, and don’t tell me what I want to hear. Be direct. No padding and no reassurance I did not ask for.
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- Open in ChatGPT. You press send Copies, then opens Last used
- Open in Gemini. You press send Copies, then opens Last used
- Open in Claude. You press send Copies, then opens Last used
- Open in Grok. You press send Copies, then opens Last used
- Open in Copilot. You press send Copies, then opens Last used
- Open in Perplexity. Runs right away Copies, then opens Last used
More assistants
- Open in Meta AI. You press send Copies, then opens Last used
- Open in Le Chat. Runs right away Copies, then opens Last used
- Open in DeepSeek. You press send Copies, then opens Last used
- Open in Duck.ai. You press send Copies, then opens Last used
- Open in Google AI Mode. Runs right away Copies, then opens Last used
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- By assistant
- ChatGPT
- Gemini
- Claude
- Grok
- Copilot
- Perplexity
- Meta AI
- Le Chat
- DeepSeek
- Duck.ai
- Google AI Mode
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More like this.
Close to this one, by scene and by moment.
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Decide 5 min Both options feel wrong. What’s the third one?
Your either-or decision restated as a wider question, plus four options you hadn’t put on the table.
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Decide 10 min I don’t want advice. I want better questions.
Five questions that keep the decision yours, then a playback of what your answers said.
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Decide 10 min How do plans like mine usually turn out?
The outside view on your plan: what typically happens, how long it takes, and who beats the odds.
Needs web search