Stage 3: Vision & Direction | The Odyssey Plan

You probably think you have one life plan. Maybe you've got it loosely sketched in your head: a career trajectory, a city, a version of yourself five years from now. The Odyssey Plan asks you to come up with three.

Bill Burnett and Dave Evans developed this exercise at Stanford's d.school, where they've been teaching life design since 2007. Their course, "Designing Your Life," became one of the most popular electives in Stanford's history, and the book that followed (2016) has been translated into 30+ languages. The Odyssey Plan is the centerpiece exercise.

The logic is simple: when you only consider one future, you cling to it. You stop noticing alternatives. You confuse "this is the plan" with "this is the only plan." Three plans break that grip.

The psychology behind it

Hazel Markus and Paula Nurius introduced the concept of possible selves in 1986. Their research showed that people carry mental images of who they could become, both hoped-for and feared versions. These possible selves shape motivation, decision-making, and emotional wellbeing in measurable ways. The people who can articulate multiple positive futures tend to be more resilient when any single path hits a wall.

Counterfactual thinking research points in the same direction. When people generate alternatives to their current reality ("what if I had done X instead?"), they develop better mental models for future planning. The Odyssey Plan flips counterfactual thinking forward: instead of imagining what could have been, you imagine what could still be.

There's a tension here worth naming. Barry Schwartz's work on the paradox of choice (2004) showed that too many options can paralyze people and reduce satisfaction. Three plans sit in a sweet spot. Enough to break tunnel vision, few enough to actually think through seriously. Burnett and Evans landed on three deliberately, and the Stanford course data backs up that number as the point where students report the most clarity without overwhelm.

Goal pursuit research adds another layer. The concept of multifinality (Kruglanski et al., 2013) describes how a single action can serve multiple goals simultaneously. When you design three plans, you start noticing which elements show up in all of them. Those recurring threads are signals. They tell you what you actually care about, regardless of the specific path.

The three plans

• Plan 1: Your current path. If you kept going the way you're going, where does that lead in five years? Be honest, not aspirational. This is the trajectory you're already on.

• Plan 2: The alternative. If Plan 1 vanished tomorrow (your industry collapsed, your situation changed completely), what would you do instead? This forces creative problem-solving and often surfaces interests you've been sitting on.

• Plan 3: The wild card. If money and social judgment were irrelevant, what would you do? Nobody's watching, nobody's scoring. This plan tends to reveal what you actually want underneath the practical considerations.

A few things to know before you start. No plan needs to be realistic yet. Realism comes later. Right now, you're generating options and paying attention to what excites you. Some people find that their "wild card" plan contains the seed of what they actually end up doing. Others discover that their current path is genuinely the best one, but they hold it differently once they've seen what else is possible.

You're not choosing between these three. You're using them to see yourself more clearly.

The exercise

Access your Notion workbook here.

Plan 1: The current path

Where does your existing trajectory lead if you keep going?

Six-word headline:_____

Five-year timeline

Map your current direction across 5 years. Be specific about milestones, career moves, living situations, relationships, and skills you'd build. Be honest about where this path is actually heading, not where you wish it were heading.

Milestones:
Year 1:
Year 2:
Year 3:
Year 4:
Year 5:
Primary focus
Year 1:
Year 2:
Year 3:
Year 4:
Year 5:
Key risks
Year 1:
Year 2:
Year 3:
Year 4:
Year 5:

Dashboard gauges

Resources (money, skills, time, connections)
Rating (1-10):
Notes:

Likability
Rating (1-10):
Notes:

Confidence
Rating (1-10):
Notes

Coherence with your values
Rating (1-10):
Notes:

The narrative

Describe this life in detail. Where are you living? What does a random day look like? Who are you spending time with? What are you proud of?

What would need to be true

List the conditions, resources, relationships, and decisions that would make this plan real.

Questions this plan raises

Write 3 questions you'd need to answer before committing to this path.

• What assumptions are you making about this path that you haven't tested?

Plan 2: The alternative

What would you do if Plan 1 disappeared entirely?

Six-word headline:_____

Five-year timeline

Imagine your current path is gone. Your industry changed, your circumstances shifted, the door closed. What's the backup that actually interests you? This often surfaces skills, curiosities, or half-formed ideas you've been carrying around without acting on.

Milestones:
Year 1:
Year 2:
Year 3:
Year 4:
Year 5:
Primary focus
Year 1:
Year 2:
Year 3:
Year 4:
Year 5:
Key risks
Year 1:
Year 2:
Year 3:
Year 4:
Year 5:

Dashboard gauges

Resources (money, skills, time, connections)
Rating (1-10):
Notes:

Likability
Rating (1-10):
Notes:

Confidence
Rating (1-10):
Notes

Coherence with your values
Rating (1-10):
Notes:

The narrative

Describe this life in detail. Where are you living? What does a random day look like? Who are you spending time with? What are you proud of?

What would need to be true

List the conditions, resources, relationships, and decisions that would make this plan real.

Questions this plan raises

Write 3 questions you'd need to answer before committing to this path.

• What skills from your current life would transfer to this plan? What would you need to learn from scratch?

Plan 3: The wild card

What would you do if money and status were completely irrelevant?

Six-word headline:_____

Five-year timeline

Now imagine that nobody's judging. You don't need to worry about money, and social pressure doesn't exist. What do you do with your days? Where do you live? Who's around you? This plan often reveals core desires that get buried under practical concerns. Pay attention to what shows up here.

Milestones:
Year 1:
Year 2:
Year 3:
Year 4:
Year 5:
Primary focus
Year 1:
Year 2:
Year 3:
Year 4:
Year 5:
Key risks
Year 1:
Year 2:
Year 3:
Year 4:
Year 5:

Dashboard gauges

Resources (money, skills, time, connections)
Rating (1-10):
Notes:

Likability
Rating (1-10):
Notes:

Confidence
Rating (1-10):
Notes

Coherence with your values
Rating (1-10):
Notes:

The narrative

Describe this life in detail. Where are you living? What does a random day look like? Who are you spending time with? What are you proud of?

What would need to be true

List the conditions, resources, relationships, and decisions that would make this plan real.

Questions this plan raises

Write 3 questions you'd need to answer before committing to this path.

• What's stopping me from incorporating even a small piece of this plan into my actual life right now?

Comparing your three plans

Put all three side by side to see the patterns that emerge.

• Resources needed - Plan 1 (current path) - Plan 2 (alternative) - Plan 3 (wild card)

• Likability (1-10) - Plan 1 (current path) - Plan 2 (alternative) - Plan 3 (wild card)

• Confidence (1-10) - Plan 1 (current path) - Plan 2 (alternative) - Plan 3 (wild card)

• Coherence with values (1-10) - Plan 1 (current path) - Plan 2 (alternative) - Plan 3 (wild card)

• Biggest risk - Plan 1 (current path) - Plan 2 (alternative) - Plan 3 (wild card)

• Biggest reward - Plan 1 (current path) - Plan 2 (alternative) - Plan 3 (wild card)

• Skills you already have - Plan 1 (current path) - Plan 2 (alternative) - Plan 3 (wild card)

• Skills you'd need to build - Plan 1 (current path) - Plan 2 (alternative) - Plan 3 (wild card)

• Who you'd need help from- Plan 1 (current path) - Plan 2 (alternative) - Plan 3 (wild card)

• How your daily life would feel - Plan 1 (current path) - Plan 2 (alternative) - Plan 3 (wild card)

What shows up in all three?

Look for recurring elements across your plans: activities, values, types of people, locations, feelings. If something appears in all three versions of your future, it's probably important to you regardless of the specific path.

What surprises you?

Which plan excites you most? Which one scares you? Where did you notice yourself editing or censoring as you wrote?

Reflection

Spend a few minutes with the questions below. Take your time here, don't rush your answers

• Which plan made you write fastest? That speed often signals genuine excitement.

• Which plan did you resist writing? What does that resistance tell you?

• If you could combine elements from all three plans, what would that hybrid look like?

• What's the smallest step you could take this week toward the plan that excites you most?

• Who in your life has done something similar to your Plan 2 or Plan 3? Could you talk to them?

• Five years from now, which version of you would you be proudest to meet?

AI companion (optional)

How to use: Use this after you've attempted your first draft of all three plans, or if you're stuck on Plan 2 or 3. The AI works best when you give it real context about your current situation, skills, and interests. Don't hold back on the wild card; the more honest you are, the more useful the conversation.

Copy and paste the prompt below into Claude, ChatGPT, or any AI assistant:

I'm working on an Odyssey Plan exercise from Designing Your Life by Burnett & Evans. I need to create 3 alternative 5-year plans for my life. Plan 1 is my current path (where I'm headed if nothing changes). Plan 2 is my alternative (what I'd do if Plan 1 disappeared). Plan 3 is my wild card (what I'd do if money and status didn't matter).
Here's what I know so far about my situation: [PASTE YOUR CONTEXT HERE]
Help me brainstorm each plan by asking me specific questions about what I'd want my daily life to look like, what skills I'd use, where I'd live, and who I'd spend time with. Push me to be concrete and specific, not vague. If I'm being too safe or generic, call it out. After we work through all three, help me spot patterns across the plans: what shows up everywhere, what surprises me, and what that might mean.