7 Odyssey Plans
Dysfunctional Belief: I need to figure out my best possible life, make a plan, and then execute it.
Reframe: There are multiple great lives (and plans) within me, and I get to choose which one to build my way forward to next.
Watch
Concept
Where people go wrong (regardless of their age, education, or career path) is thinking they just need to come up with a plan for their lives and it will be smooth sailing. If only they make the right choice (the best, true, only choice), they will have a blueprint for who they will be, what they will do, and how they will live. It’s a paint-by-numbers approach to life, but in reality, life is more of an abstract painting—one that’s open to multiple interpretations.
The conclusion is that if your mind starts with multiple ideas in parallel, it is not prematurely committed to one path and stays more open and able to receive and conceive more novel innovations. Designers have known this all along—you don’t want to start with just one idea, or you’re likely to get stuck with it.
Odyssey Plans
A good designer asks questions to test assumptions and reveal new insights.
Odyssey Plans can define important things still to do in our lives, and help us remember dreams we may have forgotten. The only wrong way to do this is to not do it at all.
Odyssey Plan A : Plan A is centered your current life plan 5 years ahead
Odyssey Plan B : If Plan A could-not-exist, this is Plan B.
Odyssey Plan C : If money, time, limitations, etc. did not exist. This is Plan C.
Do
Create three alternative versions of lives you could live i.e. Odyssey Plans
Each Odyssey Plans (alternate version) is 5 years long
Create a headline or title for each of three Odyssey Plans
Ask three questions to test each Odyssey Plans
Rate how much you like each Odyssey Plans
Student Examples
Student A
Odyssey Plan A:
My 5 year plan:
-Apply for the SF MOMA internship in January
-Crush The Interview
-Get the Internship
-Graduate with my Bachelors in June
-Move to SF with my best friends
-Crush the internship
-SF MOMA hires me
-I work full time at SF MOMA and they offer to pay for Grad School
-I get my Masters and become a professor
-I get to teach the future generations design/art and get summers off to go travel the world and have enough money to buy all the clothes I would ever want and have a really cute apartment in SF
Rating 5/5
Odyssey Plan B:
My 5 year plan:
-Graduate with my Bachelors in June
-Move to SF with my best friends
-Apply for jobs in SF preferably remote
-Work at said job and apply for grad school
-Get super involved with the SF art/graphic design scene
-Graduate with my masters and land a better job
-Have a super nice apartment and the best closet ever
Rating 4/5
Odyssey Plan C:
My 5 year plan:
-Graduate with my Bachelors in June
-Take a year off to go travel the world
-Go to grad school in Europe
-Move to Paris or Copenhagen
-Learn languages
-Make art
-Have an awesome apartment with amazing interior design
-I have maison margiela tabis and all the clothes I could ever want
Rating 5/5
Student B
Odyssey Plan A — “Building Creative Stability”
Description (5 Years Ahead): I continue growing in my design career while finishing my degree and building a strong creative foundation. I’m working full-time in a design or marketing role that aligns with my values — something where I can help shape brand stories, environments, or communities. On the side, I keep developing my freelance brand (Iron Union and Ironwood Interiors), slowly growing them into established creative studios. My life is stable, balanced between creative work, lifting, and personal growth.
Three Questions:
What specific type of design work fulfills me the most long term?
Can I maintain creative energy while working for someone else’s vision?
How can I grow these side projects without burning out?
Rating: 8/10 – This plan feels realistic, steady, and aligned with who I’m becoming, though part of me still craves more creative freedom.
Odyssey Plan B — “The Entrepreneur Route”
Description (5 Years Ahead): If my current path disappeared, I’d fully dive into entrepreneurship — launching my own design and fitness-inspired brand full time. Iron Union would become a full apparel and creative lifestyle brand with events, training programs, and strong online community roots. Ironwood Interiors would evolve into an interior branding studio focusing on functional, aesthetic gym and wellness spaces. My work would center on creative direction, brand identity, and purpose-driven business building.
Three Questions:
Am I ready to take on the financial risk of running a business full time?
What support system do I need to make this sustainable?
How can I maintain creative passion while handling business logistics?
Rating: 9/10 – This plan excites me the most. It feels bold and fully aligned with my vision, but it would take courage and financial planning to pull off.
Odyssey Plan C — “The Limitless Creative Nomad”
Description (5 Years Ahead): If money, time, and limits didn’t exist, I’d travel the world while documenting design, fitness, and lifestyle culture across different places. I’d create a multimedia platform — combining photography, YouTube storytelling, podcasting, and digital design — that highlights creativity and strength in different communities. I’d design on the road, host creative workshops, collaborate with global designers, and build a following around design-meets-lifestyle storytelling.
Three Questions:
How would I balance constant travel with my need for stability and routine?
Would I still feel fulfilled creatively without a “home base” or team?
How could I turn this into a sustainable, income-generating lifestyle?
Rating: 7/10 – It’s an inspiring dream and fits my love for creativity and adventure, but it might be too chaotic long term.
Reflection:
All three plans share the same themes — creativity, community, empowerment, and design. Plan A grounds me, Plan B challenges me, and Plan C inspires me. What I’ve learned is that there’s not just one “right” life; each version has meaning and possibility. The best version for me probably blends stability with creative freedom — building something of my own while staying open to where life leads.
Student C
1. Plan Office mama
Year 1) get degree and look for job.
Year 2) Get engaged and plan wedding, design wedding things to say that I did.
Year 3) Get established in big girl career, get house to build life and family in.
Year 4) Start remote/hybrid in job, get pregnant and start planning for me and family
Year 5) be hybrid or remote in job in a very high up position, have home office and be a stay at home mama while working.
5 stars, love love love.
Am I happy? (yes) Can I financially support me and baby if anything happened to husband? (yes) Will I be professionally satisfied? (yes)
2. Plan Children's book Illustrator
Year 1) Get degree
Year 2)Create more original drawings and build a bigger illustration portfolio. get engaged
Year 3)Network with authors who align with my art style. get married
Year 4) Be a part of a published children's book and make that my personality for a while.
Year 5) Get pregnant and have other books published and fill nursery with my books.
5 Stars yippee! Am I happy? (yes) Can I financially support me and baby if anything happened to husband? (no) Will I be professionally satisfied? (yes)
3. Plan DYI Agency
Year 1) Degree, planning what my agency should be for and draft its foundation.
Year 2) Create agency brief/strategic plan and research. Marketing for business plan , get engaged
Year 3) Find people to join agency and save money for a place to host agency
Year 4) Rent and design space, make money get married
Year 5) Big boss lady for agency and start family.
Am I happy? (maybe) Can I financially support me and baby if anything happened to husband? (no) Will I be professionally satisfied? (yes)
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