Odyssey Plans: A Pathless Remix
A 5-year Odyssey Plan exercise from the Designing Your Life framework. Map out three possible versions of your next five years.
Tools & Resources
Free exercises, calculators, and templates I've created over the years. These are the same tools I've used and shared with thousands of people navigating career transitions, self-employment, and life design.
Exercises
Yearnings Template
Based on Tim Urban's framework from Wait But Why. Rank your deepest yearnings to understand what you really crave from life and work.
Fear Setting Exercise
Tim Ferriss' fear-setting framework adapted for career transitions. Define your fears, prevention strategies, and repair plans.
Values Inventory Exercise
Rate 32 values for your work life and identify your top 5. A personal values inventory to help clarify what matters most to you.
Future of Work Mindset Assessment
A 27-question assessment to measure your readiness for the future of work across Foundations, How You Create, and How You Adapt.
Calculators
Target Income Calculator
Calculate your required income based on monthly expenses, business costs, tax rate, and hourly rate. Built for solopreneurs and freelancers.
Sabbatical Planner
Work out what your time off will cost, how many months your savings cover, and what you want the time to be for.
FIRE Calculator
How much is enough, and when you get there, explained step by step. Six goals, including Pathless FIRE: time to find work you care about.
Location Arbitrage Calculator
Compare what life costs in two places and see how much longer your savings last and how much sooner you reach financial independence.
Guides & books
Career Transition Playbook
A free 45+ page guide covering job search strategy, networking, interviewing, and building a career on your own terms.
The Pathless Path Book
86,000+ copies sold. A bold exploration of what happens when we step off the default path and find new ways to live and work.