Odyssey Plans: Designing Three Alternative Futures

Three parallel five-year plans, design-thinking prototypes, and wayfinding without a fixed destination

What are odyssey plans in Designing Your Life?

An odyssey plan is a practice from Bill Burnett and Dave Evans’s "Designing Your Life" framework in which you sketch out three distinct five-year life plans — not ranked by desirability, but genuinely different in direction. The exercise exploits prototyping logic from design thinking: holding alternatives in parallel prevents premature commitment and reveals assumptions you did not know you were making. To make an odyssey plan, write one version for each path: Life 1 is the direction you are already heading, Life 2 is what you would do if that path were suddenly gone, and Life 3 is what you would do if money or other people’s opinions did not matter.

Most career and life planning assumes you should identify the right path and optimize for it. Burnett and Evans — product designers turned Stanford professors — noticed that this is precisely how engineers cause disasters: committing too early to a single solution before alternatives have been explored. Odyssey plans apply the design-thinking principle of parallel prototyping to your life: instead of betting on one future, you sketch three genuinely different ones and treat each as a real option worth understanding. The evidence base is partly from design thinking research and partly from decision-quality research on considering alternatives; the specific format is a practitioner framework with growing use in coaching and education.