Bill Burnett Odyssey Career Planning

Map out three distinct five-year career paths using Bill Burnett Odyssey Planning. This structured exercise helps you explore primary goals, pivot options, and wildcard possibilities in one sitting.

6 time blocks, 60 minutes in total.

Time blocks

Canvas Setup and Baseline: 5 min
Draw three five-year timelines side by side on blank paper
Current Path Timeline: 15 min
Map out your current trajectory or primary idea for five years
Alternative Pivot Timeline: 15 min
Detail what you would do if your first option suddenly vanished
Wildcard Constraint-Free Timeline: 15 min
Sketch a career direction assuming money and image do not matter
Dashboard Gauges Rating: 5 min
Score resources, confidence, likeability, and coherence for each
Prototype Inquiry Drafting: 5 min
Write two testing questions for each five-year alternative

About this routine

Developed by Stanford Life Design Lab co-founder Bill Burnett, Bill Burnett Odyssey Planning is a design thinking exercise for career transitions. Rather than committing to a single rigid plan, this approach invites you to visually map three distinct five-year futures side by side.

The exercise breaks down into three specific timeline drafts. Option one tracks your current trajectory or main idea. Option two charts what you would build if option one were no longer available. Option three captures a wildcard scenario where money, social expectations, and image play no role.

By adding four dashboard gauges (resources, confidence, likeability, and coherence), you evaluate each path objectively. Finishing with clear prototype questions turns abstract ideas into small experiments you can test through real conversations.

Why this routine works

Clarifies three distinct career trajectories without prematurely locking into one
Reduces career change anxiety by creating viable backup options
Identifies key assumptions to test through prototype conversations

FAQ

What is Bill Burnett Odyssey Planning?

Odyssey Planning is a design thinking exercise developed by Bill Burnett and Dave Evans at Stanford. It involves drawing three different five-year life and career plans to explore alternative futures.

What are the three lives in Odyssey Planning?

The three lives are your current path, a backup path if the first option vanishes, and a wildcard path pursued without financial or social constraints.

How long does an Odyssey Planning session take?

A focused Odyssey Planning session takes 60 minutes, allocating 15 minutes to each of the three timeline sketches and 15 minutes to dashboard scoring and question drafting.

Sources

Designing Your Life by Bill Burnett and Dave Evans
Stanford Life Design Lab Odyssey Planning Guide