Odyssey Plans are sketches of possibilities that can animate your imagination and help you choose which direction you will actually take to start prototyping.

Imagine and write up three different versions of the next five years of your life.

Try not to think of your Odyssey Plans as “Plan A, Plan B, and Plan C”—where A is the really good plan and B is the okay plan and C is the plan that you really hope you don’t get stuck with but that you would accept as tolerable if absolutely necessary. Every Odyssey Plan is a Plan A, because it’s really you and it’s really possible.

Come up with three truly different alternatives—not three variations on a theme.

• Life One—That Thing You Do. Your first plan is centered on what you’ve already got in mind—either your current life expanded forward or that hot idea you’ve been nursing for some time. This is the idea you already have—it’s a good one and it deserves attention in this exercise.
• Life Two—That Thing You’d Do If Thing One Were Suddenly Gone. When you really force your imagination to believe that you have to make a living doing something other than doing That Thing You Do, you’ll come up with something.
• Life Three—The Thing You’d Do or the Life You’d Live If Money or Image Were No Object. If you knew you could make a decent living at it and you knew no one would laugh at you or think less of you for doing it—what would you do?

Criteria for choosing what’s next may be based on:

• available resources (proximity, time, money),
• coherence (how the alternative fits into your Lifeview and Workview),
• your confidence level (do you believe you can do this?),
• and how much you like it.

Steps

1. Make each plan a visual or graphical timeline that includes personal and non-career events.
2. In each potential timeline, investigate different possibilities and learn different things about yourself and the world. Ask yourself: What kinds of things will you want to test and explore in each alternative version of your life?
3. For each plan, consider the following questions:
   1. Geography—where will you live?
   2. What experience/learning will you gain?
   3. What are the impacts/results of choosing this alternative?
   4. What will life look like? What particular role, industry, or company do you see yourself in?
4. Give a title for each option in the form of a six-word headline describing the essence of this alternative.
5. Think of two to three questions the odyssey plan is asking.
6. Gauge each timeline based on the following:
   1. Resources (Do you have the objective resources—time, money, skill, contacts—you need to pull off your plan?)
   2. Likability (Are you hot or cold or warm about your plan?)
   3. Confidence (Are you feeling full of confidence, or pretty uncertain about pulling this off?)
   4. Coherence (Does the plan make sense within itself? And is it consistent with you, your Workview, and your Lifeview?)
7. Rank each plan based on their gauges.
8. Present your plan to another person or a group.
   1. The ground rules for listening are these: Tell your listeners not to critique, review, or advise. You want them to receive, reflect, and amplify. Find two to five people who are “there for you” and will show up for an evening dedicated to helping you design your life (or who are willing to read this chapter, at the very least).

To do

• Rewrite this in your own words.

References

Burnett, Bill, and Dave Evans. Designing Your Life: How to Build a Well-Lived, Joyful Life. Alfred A. Knopf, 2016.