Odyssey Vocations: Exploring Multiple Life Paths
This tool is particularly helpful when people feel stuck in their present life stage/position. This exercise helps to unlock and reveal new possibilities that you were not even aware existed. In Designing Your Life, Bill Burnett and Dave Evans introduce the concept of Odyssey Planning (based on Homer’s book The Odyssey where Odysseus takes a ten-year journey home to Ithaca after the Trojan War).
This approach provides a creative exercise for individuals to explore 3-5 possible career and life paths instead of assuming there is only one "right" way forward. This method challenges the traditional notion of a fixed career trajectory and encourages adaptability, imagination, and intentionality.
The exercise typically involves designing three primary alternative vocations, each addressing different aspects of personal growth, fulfillment, and career evolution. Some versions expand this to four or five paths for greater flexibility.
1️⃣ Extend More of What You Are Already Doing
What if you kept going in your current trajectory but made small, meaningful improvements?
This path assumes you continue in your current field or career, but with intentional modifications to create more satisfaction, balance, and engagement.
Questions to Ask:
How can I deepen my expertise in my current job?
What if I took on a leadership role in my field?
Could I mentor others or teach within my profession?
What small adjustments would make this career more fulfilling (e.g., shifting projects, learning new skills, or changing work environment)?
Example:
A teacher could transition into curriculum development, administration, or mentoring new educators.
A pastor could write books, start a podcast, or create online courses to extend their influence beyond the local church.
This plan is great for people who enjoy their field but want to evolve within it rather than make a drastic change.
2️⃣ Total Change – If Your Job Was No Longer Available
What if your current industry disappeared? What would you do next?
This scenario forces you to rethink your career entirely, assuming that your current profession or role no longer exists. It encourages adaptability and helps you prepare for unexpected changes.
Questions to Ask:
If my current job ended today, what transferable skills would I use elsewhere?
What alternative careers have I been curious about but never pursued?
What industries align with my core values and strengths?
Example:
A graphic designer might pivot into UX/UI design, branding consultancy, or digital marketing.
A nonprofit director could shift into coaching, corporate social responsibility, or leadership consulting.
A doctor might transition to medical writing, healthcare technology, or public health advocacy.
This path is future-proofing—it helps you explore multiple career identities in case life throws unexpected changes your way.
3️⃣ If Money and Time Were No Object
What would you do if finances, education, or societal expectations didn’t matter?
This scenario encourages pure creativity and passion, setting aside limitations. Many people suppress their dreams due to financial concerns, but this exercise helps identify what truly excites and energizes you.
Questions to Ask:
What would I do purely for joy without worrying about money?
If I had infinite resources, how would I spend my time?
What personal projects or dreams have I delayed due to fear or obligations?
Example:
A corporate executive might open a small organic farm.
A software engineer might become a travel writer or documentary filmmaker.
A minister might start an artist retreat center or launch a nonprofit to address areas of passion, either locally or abroad.
Even though this plan might seem unrealistic, it uncovers core passions and hidden desires that could be incorporated into real-life plans in smaller ways.
4️⃣ The “Side Quest” Approach (Optional Add-On)
What if you designed a career based on a personal passion, even if it remained a side project?
Not every path requires quitting your job. Some people have an entrepreneurial dream, creative pursuit, or service-oriented calling that can be cultivated alongside their primary career.
Example:
A financial analyst could launch a YouTube channel on investing for young professionals.
A nurse could start a blog or podcast on self-care for healthcare workers.
A pastor could create a coaching business for other church leaders.
A businessman could start an Airbnb out of their house or via rental arbitrage.
This approach provides a low-risk way to explore new vocations while keeping financial stability.
5️⃣ The Purpose-Driven Path (Another Optional Add-On)
What if you designed your life based solely on your deepest sense of mission or faith?
For those seeking a more impact-driven vocation, this plan prioritizes service, ministry, justice, or personal convictions over traditional career goals.
Example:
A lawyer might transition into human rights advocacy.
A tech entrepreneur might focus on developing sustainable technology for underprivileged communities.
A teacher might move into missionary work or nonprofit education.
This approach asks: What breaks my heart? What can I uniquely contribute to the world?
How to Use Odyssey Planning to Make Real Decisions
1️⃣ Sketch Out Each Path
Create three (or more) different plans.
Use your imagination and simply brain storm as many ideas as possible.
Include skills, financial implications, risks, and rewards.
2️⃣ Evaluate What Resonates
Rank each plan on excitement, confidence, and coherence (how well it fits with your values).
3️⃣ Prototype Small Experiments
Instead of jumping all in, test the waters (shadow someone, take a class, volunteer, conduct a small experiment).
4️⃣ Seek Wise Counsel
Share your plans with mentors, friends, or faith leaders to gain new insights.
Final Thought: There’s No One Right Path
The beauty of Odyssey Planning is that it frees us from the myth of one perfect career. By designing multiple paths, we recognize that life is fluid, adaptable, and full of possibilities. The goal isn’t to predict the future—it’s to create a life of purpose and joy, no matter the path chosen. You may realize that you are not stuck after all – you actually have more options to explore than you thought.
What paths excite you the most?
About the Author: Dr. Jay Moon, PhD, MBA, P.E. is a storyteller, strategist, and scholar with a passion for bridging faith, work, and mission. With 13 years as a SIM missionary in Ghana among the Builsa people, he has firsthand experience in church planting, water development, evangelism, and discipleship. Now a Professor of Evangelism & Church Planting at Asbury Theological Seminary, he also leads the Office of Faith, Work, and Economics, equipping leaders to integrate faith in everyday life.
A prolific author, Jay has written six books—including Intercultural Discipleship and Effective Intercultural Evangelism—and edited seven more. A sought-after speaker on church planting, marketplace mission, and evangelism, he has served as president of APM and GCRN and is the incoming president of AETE and ASM.
Beyond academia, Jay thrives in hands-on creativity, from building treehouses and throwing axes to mentoring small business innovators—always looking for new ways to connect faith and action.