Odyssey Planning

Odyssey Planning is a structured exercise that empowers you to prototype three distinct five-year trajectories of your life. Rather than fixating on a single “correct” path, Odyssey Planning embraces multiple possibilities, reducing decision anxiety and encouraging creative exploration. The method rests on three key principles:

Multiple Right Answers
Life isn’t linear. There are many valid futures.

Prototyping
Sketching futures as “Odysseys” helps you test ideas before full commitment.

Iteration
Regularly revisiting and refining plans drives alignment with evolving values.

Life One: Current Trajectory
Sketch the extension of your existing path or the project you’ve been incubating.

Life Two: Alternative Pivot
Imagine the path you’d choose if Life One became impossible.

Life Three: Wild-Card Vision
Envision a life unconstrained by finances, reputation, or practicality.

Map each year from now (Year 0) through Year 5, integrating both professional and personal milestones:

• Career Events: promotions, role changes, entrepreneurial ventures.
• Personal Milestones: relationships, health goals, travel, creative projects.
• Interleaving Activities: workshops, side-projects, learning modules.

Use simple graphics (lines, icons, or color coding) to portray progression and interconnections. At least one career and one personal milestone per year ensures holistic design.

For each Odyssey, write a pithy six-word title capturing its essence. This distillation sharpens focus and facilitates recall.

For each Odyssey, identify two to three probing questions that challenge your assumptions, clarify your motivations, and identify what you need to learn to move forward.

Assess each plan across four dimensions using a consistent scale (e.g., 1-5):

• Resources
  How much time, money, skills, and contacts are needed to execute the plan?
• Likeability
  How much personal enthusiasm and excitement you feel for the plan?
• Confidence
  How high is your confidence in your ability to achieve the milestones?
• Coherence
  How well does the plan align with your core values and life philosophy?

Record scores for each dimension and compare across plans to identify strengths, gaps, and preferences.

Prototyping helps you test your assumptions before fully committing. Treat each Odyssey as a series of small experiments to validate what truly energizes you.

• Interviews
  Identify 2-3 people already living aspects of each plan. Prepare questions to uncover day-to-day realities, required skills, and common pitfalls.
• Shadowing
  Arrange a half-day shadow with a person who is already living the life you want to create.
• Micro-Courses
  Enroll in a short, targeted workshop. This can offer quick wins and clarify whether you enjoy the work itself.
• Mini-Project Pilots
  Start a small project that aligns with your plan.

After each experiment, capture outcomes, surprises, and lessons learned. Use these insights to refine your Odyssey Plans.

Pause to examine each of the three plans you’ve created. You can do it on your own or by sharing your plans with a small group of trusted friends or mentors.

Schedule additional reflection sessions every few months or after significant life events. During these sessions, visit your six-word headlines, timelines, and dashboard ratings and adjust them as needed.

Action transforms vision into momentum. Choose concrete steps that propel you forward on one or more Odysseys.

• The concept of Odyssey Planning was introduced by Bill Burnett and Dave Evans in their book Designing Your Life: How to Build a Well-Lived, Joyful Life.