Odyssey planning

“Planning is everything, but the plan is nothing”

Dwight Eisenhower

If you like to plan and plan big, you’ll enjoy this exercise. Do you remember the golden 5 year plans that career advisors and managers usually recommend drawing in one of your career planning sessions? In ‘Designing Your Life’ by Bill Burnett & Dave Evans, the concept is re-framed to a whole of 3 alternative turns your life can take, making the planning more agile, less focused on one outcome only, and a lot more creative.

What is Odyssey planning?



How to do an Odyssey planning? (summary)

  1. On the first A4/A3 paper (or miro) draw or write out your exiting current plan or an idea for how your professional and personal life will look like in 5 years

  2. Now imagine what you would do in case Plan 1 cannot happen

  3. Turn on the blue sky thinking - what would you do if money and time were no object

  4. For each of the plans assess the confidence, resources, coherence, and likeness level

  5. Give each of your plans a name and list any questions you have about this plan

  6. Prototype each scenario (or test in real-life settings) each of your plans


A good prototype is touching upon conversations and/or experiences and helps you reduce the risk, expose assumptions, engage others with your ideas, collect feedback, and learn. Mini exposures like internships, mentorships, bootcamps, EiR programs, and conversations with your mentors, sponsors, or people from the field are going to get you closer to understanding the path you may want to take or what can happen shall your plan 1 become an unviable option.

Ready to deep dive?


Stanford is running a full-fledged (and free) online course on designing your life, so if you feel this is the right time to re-shape your plans more seriously or you just enjoyed this exercise, here is the link to the course.

Having spoken to many professionals in various stages of their career, I thought to note that changing paths and moving to a new career is perfectly normal. Going through a period of uncertainty and not knowing exactly where you'd like to land next is also very much natural. And this happens to all of us. To showcase that - Stanford lab summarised the sociological research to show how the perceived life stages had changed over the years:

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