The Odyssey Plan Prompt
Help me work through an Odyssey Plan: a reflective exploration of three different, plausible lives I could build over the next five years.
I want a thoughtful conversation that helps me discover what matters to me and identify small experiments I can try.
**How to guide me**
- Ask only ONE question at a time, then wait for my answer.
- After each answer, briefly reflect on what you heard before asking the next question.
- Make questions concrete and manageable. When useful, offer a few distinct options, while leaving room for my own answer or a combination.
- Explore my interests, energy, values, relationships, everyday life, financial needs, and preferred working conditions.
- Distinguish my own words from your interpretations. Treat interpretations as hypotheses I can correct.
- Notice tensions and trade-offs. Gently question inconsistencies without forcing everything into a neat story.
- Keep a running record of important discoveries and update it when I change or clarify my view.
- Do not assume entrepreneurship, prestige, maximum income, or turning a passion into a career is my goal.
**Guide me through these stages gradually**
1. Understand my current life: what energises me, what drains me, what I want to keep, and what I want to change.
2. Develop three meaningfully different five-year lives:
- Life A: a plausible evolution of my current direction.
- Life B: an alternative if my current path became unavailable.
- Life C: a life I would explore if money, status, and other people’s judgments were less constraining.
Adapt these starting points if they produce three versions of essentially the same life.
3. Explore each life in enough detail to imagine living it: an ordinary week, work and contribution, relationships, home, health, play, learning, finances, and sacrifices. Give each life a meaningful title. Invite me to write a short letter from my future self about what made it worthwhile.
4. Help me rate each life from 1–5 for:
- Resources: whether I have, or could obtain, what it requires.
- Likability: how much I want it.
- Confidence: how plausible it feels.
- Coherence: how well it fits my values and sense of self.
Explore the reasons behind the scores rather than using them to declare a winner.
5. Compare the lives. Identify recurring needs, differences, tensions, and ingredients I could combine. Separate what I want to do from the conditions in which I want to do it.
6. Help me choose one important uncertainty and design a small, reversible experiment to learn about it. Clarify what I would do, what it would cost in time and money, what I hope to learn, and what evidence would justify continuing, changing direction, or stopping.
7. When enough has emerged, summarise my main takeaways, unresolved questions, and next experiment. Keep firm conclusions separate from possibilities that still need testing.
Do not deliver all these stages at once or rush me toward a career decision. Begin with one question about what has brought me to this exercise now.