Tools & Tips

The Odyssey Plan: Reframing Your ‘Five Year Plan’

Example Odyssey Plan from ‘Designing Your Life’ by Bill Burnett & Dave Evans

During our Life Sprint speaks to Gregory Heller event, the career services professional spoke about the benefits of creating a personal Odyssey Plan. If you’ve never heard of this tool before, an Odyssey Plan is a ‘five year plan’ but not as you know it. It’s essentially a brainstorm about how you would like your life to look in the future.

The name Odyssey Plan comes from NYT social commentator David Brooks, who first described the period of exploration between 20 and 35 as the ‘odyssey years’ where people between adolescence and adulthood explore and discover who they’re going to be when they grow up.

When you get interrogated by a family member about your five year plan, many people struggle to answer or deflect the question. Even the earnest, goal-oriented career adviser wants you to plan out your life with the imposing ‘where do you see yourself in five years’. You might be thinking, how can I predict the future?

An Odyssey Plan is not about predicting your future trajectory but rather about unearthing and ideating the elements that make up the version of you that’s “living your best life.” We find this exercise really insightful when approaching the big “what shall I do next?” question. Matt Haig’s philosophical novel The Midnight Library is essentially a fictional Odyssey Plan; a celebration of life's endless possibilities and of self-exploration.

“If you plan for nothing, you’re going to get nothing.”

Bill Burnett, Executive Director of the Design Program at Stanford University and co-author of the NYT Best-seller Designing Your Life.

Starting out

When making an Odyssey Plan you’re going to create at least three different five-year timelines or alternate realities. Each version should feature professional and personal milestones, as well as bucket list items. The goal is to map out multiple ways in which your life could unfold. Remember, the Odyssey Plan is less about formulaic planning and more about ideation and potentiality. We recommend watching Bill Burnett’s Odyssey Plan playlist to get your creative juices flowing for this task.

  1. In the first version, you ideate a plan based on what you think you’re most likely to do. 
  2. In the second, you ask yourself what might happen if plan A disappeared and you had to pivot. 
  3. Finally, the third iteration is for blue sky thinking where you envisage what your life would look like with absolutely no limitations, financial or otherwise.

As you consider each plan, you assess to what capacity or extent you have the: resources, confidence, coherence as well as whether it will fulfill you. Then, give it a name and list any questions you have about each plan.

When you’re ready to explore one of your plans further, Bill Burnett suggests finding someone who’s already doing what you’re interested in. This person is already living your future. Talk to them about their experiences to confirm whether you’re moving in the right direction.

When should you make an Odyssey Plan?
There’s no prescribed time to make an Odyssey Plan, but you might look to create one when you are:

  • Facing lots of change or uncertainty
  • Graduating from university
  • Wanting to change your job
  • Wanting a career change

Transitional moments like these lend themselves to Odyssey Planning because they force you to figure out what you need to do to move forward. More ideas create more choices, so brainstorming like a designer can help you get “unstuck” in your thinking.

Many people find it a useful exercise to do every few years, and you might even want to save your previous plans to keep track of how far you’ve come, and remember what your dreams were.


Creating an Odyssey Plan can be an instrumental first step in thinking about what you want from life. But Life Sprint’s four-week collaborative process can help shape your future. Life Sprint has been designed to help reframe career challenges, identify obstacles and take small but powerful steps toward a better life. 

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