What If You Had Three Lives to Live?
How a simple 5-year design tool from Stanford can help you reclaim your future even if you’re not sure where to start
What if you stopped planning your life around what’s likely and started designing it around what’s possible?
Take a moment to ask yourself: are you craving a shift, a spark, or a complete reinvention?
The Odyssey Plan is a powerful 5-year life design tool that helps you map out three distinct versions of your future. It’s the kind of thing many of us mean to do — think seriously about what’s next — but rarely in a structured or imaginative way.
This is your chance to do it differently. With intention, clarity, and a bit of creative boldness.
The Odyssey Plan is a clear, practical tool developed at Stanford University to help you map out three different versions of your next five years. Used by designers, career changers, and coaches alike, it’s a powerful way to rethink what’s possible and make intentional decisions about your future.
Now, I’ve adapted it for people who’ve outgrown autopilot. The kind who think deeply, laugh easily, and know life’s too short to live by default.
This is not a personality quiz. It’s not astrology. And it’s not about setting goals and grinding your way through them. It’s about prototyping a life, or three, that could be yours.
Why Do This?
Because if you don’t imagine the future you want, you’ll default into a future you never consciously chose.
Because your next five years might just be your most exciting if you design them with intention.
Because most of us are still operating under someone else’s blueprint. This is your chance to scribble in the margins and create your own.
The Odyssey Plan: Step-by-Step Guide
You’re going to map out three different versions of your life over the next five years.
Try mapping out three different futures:
One based on what you’re already doing
One based on a pivot or dream you’ve considered
One that’s a bit of a curveball, something you’d try if there were no constraints
They don’t need to be perfect. You’re not predicting the future. You’re exploring what’s possible.
What You’ll Need:
60 minutes of uninterrupted time
A notebook or printable worksheet (you can download one at the end)
An open mind
Plan 1: The Optimised Now
What if you continue down your current path but level it up slightly?
Describe what your life looks like if you stay the course for five years. Maybe you grow your business. Maybe you go part-time. Maybe you finally learn French.
Prompt questions:
What are you doing for work?
Where do you live?
Who are you surrounded by?
How does your day start and end?
What gives you energy?
What’s starting to feel stale?
Plan 2: The Road Not Taken
If Plan 1 suddenly became impossible, what else might you do?
Maybe you retrain. Maybe you move cities. Maybe you lean into a long-lost creative impulse. This version of your life should be tangibly different.
Prompt questions — You can use the prompts for Plan 1, and add these:
What’s calling you that you’ve been ignoring?
What would you do if you had to start over (but with all your current wisdom)?
What feels secretly exciting but you’ve never admitted it out loud?
Plan 3: The Wild Card
This one’s the no-holds-barred version.
If money, reputation, and logic weren’t a factor, what would you do with your life? This is your pirate ship plan. The one where you might change your name and become a travel photographer in Iceland. Or open a community bookshop-slash-café-slash-reiki den.
Prompt questions — You can use the prompts for Plan 1, and add these:
What life would you live if no one was watching?
What have you always fantasised about?
What feels outrageous but life-affirming?
Now, Evaluate Each Plan
Score each Odyssey Plan on a scale of 1–10 for the following dimensions:
Definitions:
Excitement: How energised does this plan make you feel?
Confidence: How doable does this feel based on your skills, time, and mindset?
Coherence: How aligned is it with your values and identity?
Resources: Do you have (or can you access) the money, support, or knowledge to begin?
Total the scores but don’t choose based on numbers alone. Sometimes the lowest-scoring plan is the one worth pursuing.
Reflect & Decode
After writing and scoring your plans, answer these:
Which plan surprised you most?
Which one feels most like you, even if it’s scary?
What themes or values show up across all three?
What might you prototype now, without a major life overhaul?
Start Small: Prototype Your Future
The Odyssey Plan isn’t about quitting your job or moving to Morocco tomorrow. It’s about exploring paths through small experiments:
Talk to or shadow someone who’s living one version of your Plan 2
Take a one-day course in your Plan 3 world
Rearrange your daily routine as if you were already living your chosen plan
Designers don’t launch perfect products. They test, learn, and iterate. So can you.
Want the Printable Version?
I’ve created a PDF worksheet of the Odyssey Plan. It includes:
Fill-in-the-blank template for each plan
Evaluation grid
Reflection prompts
Finally
There’s no such thing as one right life. There are many and some might be waiting just off-stage. This exercise won’t hand you answers. But it will show you that you have choices. That your next chapter is designable. That it’s not too late and you’re not too early.
Don’t let inertia decide for you. Design with intent. Age on purpose.
Live like you mean it.
Shenmag Digest: Last Week’s Top Takeaways
Missed a post? Catch up on last week’s best insights on pro-ageing strategies, brain health, and thriving in your Third Act:
The Tiny Daily Habits That Quietly Erode Your Brainpower
And the simple recalibrations that restore clarity, focus, and emotional resilience
Monday, May 12It’s Not Your Age, It’s What You Believe About Ageing
How to reset your mindset, your brain, and your future
Wednesday, May 14The Silent Brain Drain: Alcohol and Cognitive Ageing
Why even ‘moderate’ drinking accelerates memory loss and how to protect your brain without going sober overnight
Friday, May 16
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Nice article, Stephanie. Open to collaboration and recommendations. Thank you.
I’d try to figure out the first one before venturing into the other two.