Career & Life Leaps
A visual mapping exercise that designs 3 distinct alternative 5-year futures to shatter the myth of having only 'one right life path'.
Bill Burnett & Dave Evans (Stanford Life Design Lab, 'Designing Your Life')
9.4/10
CORE FORMULA
How to use it
Life 1 (The Default): What does your life look like in 5 years if you stay on your current exact path and see it through? Life 2 (The Pivot): What if Life 1 suddenly vanished tomorrow? What alternative skill or career path would you build? Life 3 (The Wildcard): If money, social expectations, and fear of judgment did not exist, what would your life look like? Score each path across 4 gauges: Resources (Do I have what it takes?), Likability (Do I love it?), Confidence (Can I do it?), and Coherence (Does it match my values?).
Where this helps most
Mid-20s / mid-30s life transitions, pre-marriage vision alignment, career redesign, mid-career sabbaticals, post-exit founder pivots.
A real-life example
Kabir and Tanya are engaged but arguing over where to live and what careers to prioritize. Instead of locking into an ideological battle, they each independently map 3 Odyssey paths. They discover their Path 2s align closely: spending two years building remote consulting businesses before settling down. Odyssey Planning revealed a shared alternative they had never discussed.
What it does well
Eliminates paralyzing 'what-if' regret; normalizes having multiple viable paths; exceptional for couples aligning their shared future.
When to pause
Requires deep creative visualization, honest self-inquiry, and 60+ minutes of dedicated workbook exercises.
A question to sit with