The Odyssey Plan: Design Thinking for Your Career
While navigating a job change I came across the Odyssey Plan from Stanford's Life Design Lab. It's a framework from Bill Burnett and Dave Evans (the "Designing Your Life" authors) that applies design thinking to career planning. As engineers, we prototype systems all the time. So …
why not prototype our lives?
The Framework
The Odyssey Plan asks you to map out three radically different 5-year futures:
Plan 1: Your current trajectory. What does life look like if you stay the course?
Plan 2: What would you do if Plan 1 vanished tomorrow? The rug-pull scenario.
Plan 3: What would you do if money and other people's opinions didn't matter?
The key constraint: these need to be genuinely different paths, not variations of the same thing. Being a Staff Engineer at Company A vs Company B isn't two different lives. Same life with different logos.
Why It Works
Engineers love prototyping. We spike solutions, run experiments, validate assumptions. The Odyssey Plan is basically prototyping applied to career decisions.
The three questions force you to surface things you might be avoiding:
Unfinished business: What's nagging at you? That side project you never shipped? The domain you always wanted to work in? The skill you keep meaning to learn?
Contingency planning: Most of us don't think about what happens if our current situation disappears. Layoffs happen. Companies pivot. Industries shift. What's your backup?
Permission to dream: Plan 3 is where it gets interesting. Removing money and social pressures reveals what you actually want versus what you think you should want.
The Dashboard
For each plan, you rate yourself on four metrics:
Resources: Do you have the time, money, skills, and network to pull this off?
Likability: How excited are you about this future?
Confidence: Can you actually make this happen?
Coherence: Does this align with your values and worldview?
It's like a health check for life plans. Low confidence but high likability? Maybe you need to prototype that path with smaller experiments. High resources but low likability? You might be optimizing for the wrong thing.
Applying It
I spent an evening sketching out my three plans. The exercise bought a few things to light:
Plan 1 was comfortable but had some gaps I'd been ignoring. Plan 2 forced me to think about what I'd actually do if my current role evaporated. Plan 3 was the most revealing. When you strip away external validation, what's left?
The goal isn't to pick one plan and commit. It's to have more ideas, because more ideas means better ideas. Some elements from Plan 3 might be worth prototyping in Plan 1. Some contingencies from Plan 2 might be worth preparing for now.
Life design is just applying the engineering experimentation and prototyping mindset to career decisions instead of code.
The authors put it well: designers don't think their way forward, they build their way forward.
Happy hackin'!
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