While my every night doomscrolling ses, I came across Ali Abdaal taking about "The Odyssey Plan", a five-year planning framework. It seemed interesting to me, let's do it together.

What is The Odyssey Plan?

The Odyssey Plan is rooted in the Design Thinking framework, originally developed by engineers at Stanford and adapted by Bill Burnett and Dave Evans in their book Designing Your Life. The exercise draws on the concept that our lives are "design projects" that can be iteratively shaped by creatively envisioning, prototyping, and testing different versions of our futures.

The plan helps people avoid "decision paralysis" by imagining multiple potential life paths, making it easier to explore choices without fear of making a "wrong" decision. The name itself references The Odyssey, an epic journey full of challenges, discovery, and self-realization—mirroring the personal journey of exploring possible futures.

The Three Paths

1. Current Path

continuing on your current track

The steady-as-she-goes path. Keep to what I know, what I’ve built up so far. Project out the next five years in this same groove. The plan? Grow within the fields I’m familiar with. Deepen my skills, maybe a promotion here, a side project there. Maybe add some mentorship or teaching. Imagine five years from now, climbing up that familiar ladder. A solid path, predictable, but a foundation nonetheless.

2. Alternative Path

exploring a different career or passion

A gentle deviation, this second path. What if I took what I know and bent it toward something else? An industry shift or new niche—taking existing skills and weaving them into something close but fresh. Could be consulting, freelance gigs that tap into untapped skills, new collaborations. Five years from now, I could look back and see I followed my interests more flexibly, with a hand in many places but still within reach of a solid foundation.

3. Wild Card Path

an adventurous or unconventional option

The big leap. Call it the moonshot, the offbeat trajectory, the "what if I just went for it?" path. Maybe it’s diving into a completely different career, something I’ve only daydreamed about but never touched. A life out of left field, unpredictable, but thrilling. This one would mean letting go of what I know, even if it’s risky or a bit absurd. In five years, who knows? But maybe that’s the point.

The Timeline

Each path gets its own five-year spread—one column for each year, just a simple breakdown, nothing too detailed. Think of it like a rough timeline, loose yet promising: Year 1 as the jumpstart, Year 3 as the anchor, and by Year 5, something fully realized.

• Year 1: First moves. What skills, resources, or connections do I need? Begin.
• Year 2-3: Foundation setting. Gain traction, learn, maybe pivot.
• Year 4: Solidify the path or adapt as needed.
• Year 5: A place to arrive, but more likely, just a new launchpad.

Rating the Paths

For each path, I’ll keep it simple. Rank each with a quick check-in:

• Resources: Do I have what I need? Can I get it?
• Excitement: Does this fire me up or feel obligatory?
• Meaning: Is it true to my values or just shiny?
• Sustainability: Could I see myself here long-term?

Reflection

The ultimate question: where’s the pull? Not the “should” or “must” but the “could,” the kind of path that resonates even if it doesn’t make perfect sense. I might take one step forward in each, a single toe in the water, and see which way the current moves me. Or I could jump headfirst into one, chart a steady course, and let the rest drift as ideas I may return to, someday.

So here it is—the Odyssey Plan, stripped down, bare bones, but mapped out in possibilities. There’s something thrilling about committing to a few maybes, giving each a bit of space to breathe. A guide, a rough sketch, a map-in-progress. And maybe, just maybe, one of these paths will take me somewhere I hadn’t planned, but exactly where I want to be.