Have you ever felt stuck trying to plan your future, unsure of the right path to take?
When faced with these moments, we often try to settle on one “correct” life plan. This approach puts pressure on our choices, creating anxiety and paralysis. We worry about making the right choice, but in reality, the future is full of possibilities and many right choices. There’s more than one you – you could be. That’s where Odysseys, a core concept from Designing Your Life and can help. This tool allows you to explore multiple possible futures, giving you clarity and confidence in your life decisions. Time and time again, participants from DYL workshops and readers of the books site Odysseys as the most transformative tool.
Why Prototype Your Future?
Most of us make career and life decisions based on what seems logical or expected. But what if there’s a better option—one you haven’t considered yet? Prototyping multiple futures helps you:
- Break Free from One-Path Thinking – Life isn’t linear. Creating different versions of your future helps you realize that there isn’t just one “right” choice.
- Reduce Fear of Failure – If you’ve considered multiple possibilities, you won’t feel as if everything is riding on one decision.
- Encourage Exploration – By mapping out various futures, you can test different ideas before fully committing.
- Align with Your Interests – You may discover a path that better fits your passions and strengths.
How to Create Your Odysseys
To create Odysseys you’ll develop three different versions of your life for the next five years:
- The Expected Path – This is the story you tell today about the life you’re currently living. It’s based on the trajectory you’re on now, such as continuing in your current job or field.
- The Alternative Path – What if your current plan were no longer an option? What other career or lifestyle might you pursue?
- The Wild Card Path – If money and social expectations weren’t a concern, what would you do? This is your “dream” scenario.
For each plan, consider moments and experiences you’d like to have over the next 5 years. Challenge yourself to draw these moments (drawing helps to activate your creativity in a different way).
After you’ve visualized, assign a title and assess how you really feel about what you put down on paper. Sometimes we brainstorm and realize we didn’t get what we wanted, but embrace the prototype mentality. Do another!
Bringing Your Odysseys to Life
Once you’ve created your Odyssey Plans, take steps to prototype them:
- Talk to People Living That Life – Conduct informational interviews with professionals or individuals who have pursued similar paths.
- Try Small Experiments – Shadow someone in your desired field, take a class, or start a side project to test your interest.
- Reflect and Iterate – Which plan excites you the most? Which aligns best with your values? Adjust as needed.
Designing a Life You Love
There’s a magic we see in the faces of workshop participants when they go through this activity. When faced with 3 different futures, people often note elements in each life that are thrilling and possible. Breaking free of a single life plan helps to create more possibility, including beyond the 3 you created.
Odyssey planning reminds us that life is flexible, and there are many fulfilling ways to live. Instead of feeling trapped by a single path, you can design multiple versions of success and happiness. By prototyping your future, you’ll make more informed decisions, reduce uncertainty, and move forward with confidence.
Download our Odyssey Planning Template and start designing your three possible futures. Your best life isn’t a single plan—it’s the one you actively create!
