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01 · Begin

Three lives.
Not one answer.

I have always been suspicious of the question, “Where do you see yourself in five years?”. It assumes that somewhere out there is a correct future waiting to be identified, and that the task is simply to make the right prediction. The Odyssey Plan, developed by Bill Burnett and Dave Evans as part of Stanford’s Designing Your Life methodology, starts somewhere more interesting: what if there isn’t one future?
Instead of committing prematurely to a single path, you design three radically different five-year lives. The first extends the trajectory you are already on. The second asks what you would do if that life suddenly became impossible. The third removes money, status and other people’s expectations from the equation altogether.
Odyssey planning works by replacing the pressure to predict the future with the discipline of designing alternatives. You will create three distinct five-year lives, compare how they feel, and then prototype the parts that deserve real-world evidence.

The point is not to identify the “correct” life. The point is to make your assumptions visible, expand the field of possibility, and discover what becomes interesting when you stop treating your present path as inevitable.

Life 1

The story you are already telling.

Extend your current trajectory into the next five years.

Life 2

The alternative.

Assume Life 1 becomes impossible. What else could become real?

Life 3

The wildcard.

Remove money, prestige, and expectation. What would you explore?

This version includes the original five-year timeline, short plan title, questions/curiosities, Resources / Likeability / Confidence / Coherence gauges, cross-plan reflection, and a prototype step.
02 · Compass

Before designing futures, define what matters.

These are not commitments. They are the lenses through which you will later judge coherence.

Record constraints without allowing them to eliminate possibilities too early.

06 · Compare

Look across the lives, not down one of them.

Comparison is useful when it reveals energy, tension and recurring preferences. It is less useful when it becomes a premature ranking exercise.

07 · Reflect

What did the three futures reveal?

Write from observation rather than justification. Notice where your energy rises, where it drops, and which values keep returning.

Do not choose yet

Which parts of each plan deserve evidence before they deserve commitment?

08 · Prototype

Convert imagination into evidence.

A prototype should be small, reversible, cheap enough to try, and capable of teaching you something that thinking cannot.

Next learning question

Your three odysseys