Your future, 3 ways
How to create your Odyssey Plan, no cyclops or shipwrecks required
Hi there! You’re reading the Bonfire newsletter from Kevan Lee & Shannon Deep. Each week, we highlight learnings from our experience as in-house marketers turned agency owners who think a lot about creativity, our relationship to work, and how all of that impacts our identities.
Wishing you a great week!
“No plan for your life survives first contact with reality.”
That’s a tenet of the Stanford Design Lab’s Odyssey Plan, conceived by professors Bill Burnett and Dave Evans. I ran across it in a video, which is part of this larger series on designing your life.
The whole thing is an interesting glimpse into design thinking applied at a personal/professional level. And while it’s definitely created with college students in mind, I recommend it as food for thought! The method breaks life down into 6 common transition points, one of which they’re calling the “Odyssey Years,” which seems to be the time after college graduation.
But this Odyssey Plan can seemingly apply to any moment of transition, including what Burnett and Evans call an Encore Career: a second, later career that’s for meaning rather than money.
And if that doesn’t sound like a lot of what we’re unpacking week in and out in this newsletter, I don’t know what does!
I’m not going to go through all the different aspects of the Odyssey Plan, but there’s a key brainstorm/thought experiment at the center of it that I want to highlight as particularly valuable/insightful: the 5-Year Timelines.
The premise is simple: instead of trying to figure out the single best path forward, you design three completely different versions of your future into the next 5 years. Not three versions of the same life—“I could work for tech company X, tech company Y, or tech company Z!”—but three genuinely different lives.
When most of us think about the future, we only imagine one scenario: The life that happens if we keep doing what we’re already doing, but, like, better. With a promotion. Plus money and a partner. Add in some achievements. But that’s still the same basic trajectory. The Odyssey Plan asks you to imagine two more radically different timelines that could still be yours, even if only for the sake of pushing mental boundaries.
The Odyssey Plan calls them timelines, but you could think of them as directions or paths. I also think that if you’re just doing this as a thought experiment, you don’t even need to consider only the next five years. Could be short term, could be even longer term. Pick a time horizon that’s meaningful to you now!
Here are the three paths the Odyssey Plan entails:
Path 1: What happens if I succeed at what I’m doing right now?
This might seem obvious or simplistic, but I think it’s actually sneaky-complex. Especially when we’re full-on in the middle of our plans and goals, we can get a little myopic, losing the forest for the trees.
So this first path asks you to extrapolate your life as it is today into the future.
The set up: If you keep doing what you’re doing, what will your life look like, personally and professionally? Or if you achieve what it is you’re working towards right now, what will it look like then?
Paint a picture: Imagine where you live. Picture what you do for work and how much time you’re working. Who are you spending time with? Who are your primary relationships? How much free time do you have and what do you do with it? What responsibilities and possibilities come with succeeding at what you’re currently working toward?
Now: Staying in this same future, how do you feel on a daily basis? Is it where you want to be, what you want to do, how you want to feel, or are you going somewhere on autopilot? If your current ambitions are fully realized, what has changed and what stays the same from your life now? What problems do you have that you don’t have today?
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Path 2: What if I did something completely different?
This question sometimes feels irresponsible or irrelevant to ask. Because you’ve (perhaps) invested years into your current path, built expertise, credibility, identity, maybe even momentum.
And yet!
This is just a thought experiment, so…What if none of that existed? What would you do, realistically, if you weren’t trying to maximize the return on your previous decisions?
You’re going to repeat the questions in the first path, only you can’t keep doing what you’re currently doing. That option no longer exists. If you’re currently a social media manager, pretend like the whole idea of social media was obliterated from existence. If you’re living in City A—guess what? You can’t anymore. You must do something different. Now…what is it?
The set up: If you had to do something completely different with your life, what would it look like, personally and professionally? If you couldn’t do/have/be what you are now, what is the next most appealing option?
Paint a picture: Imagine where you live in this alternate reality. Picture what you do for work and how much time you’re working. Who are you spending time with? Who are your primary relationships? How much free time do you have and what do you do with it? What responsibilities and possibilities do you have now that you’ve done something completely different?
Now: Staying in this same upside-down future, how do you feel on a daily basis? Is it where you want to be, what you want to do, how you want to feel? Does it feel significantly more or less aligned than your current reality? If these “alternative” ambitions are fully realized, what has changed and what stays the same from your life now? What problems do you have that you don’t have today?
Path 3: What would I do if money didn’t matter and nobody was watching?
The first two questions are about your current life and near alternatives. This one is about pure desire.
On this path, you do not need money. And no one is watching you. No LinkedIn announcement. No family questions. No audience.
The idea here is that in those conditions, the answer to the quest of what you spend your time on is a set of activities that feel intrinsically meaningful to you.
The set up: All your material needs are taken care of, and everything you spend your time doing is done privately. Not exactly in secret, but free from judgement, commentary, and feedback. So what does your life look like now?
Paint a picture: Imagine where you live without the barrier of cost or input from others. Are you still working? If so, what work are you doing? Who are you spending time with? Who are your primary relationships? How much free time do you have and what do you do with it? What possibilities do you have now that you’re untethered from resources and other people’s regard?
Now: How do you feel on a daily basis? Is it where you want to be, what you want to do, how you want to feel? Does it feel significantly more or less aligned than your current reality? If you didn’t need to earn money and wouldn’t or couldn’t be observed by others, what has changed and what stays the same from your life now? What problems do you have that you don’t have today?
The power is in the comparison
In the actual Odyssey Plan exercise from Stanford, you pick your “preferred” timeline and then you blow it out into a 10-year vision and you give it a symbol and the whole nine yards. But they do encourage you to look at all three paths side by side, and I think this is where the real power of this exercise comes in.
When Path 1 and Path 3 are radically different
If your current path leads to becoming a VP, founder, partner, or executive, but your money-doesn’t-matter-and-nobody’s-watching life involves gardening, writing poetry, teaching, restoring old houses, or spending afternoons with friends, there’s a question worth asking:
How much of my current ambition is mine, and how much of it is borrowed from other people?
That doesn’t mean you should quit your job and become a shepherd. But it may mean you’ve been optimizing for status, security, or external validation while neglecting something(s) important.
When Path 1 and Path 2 are radically different…on the surface
Consider whether your differences in Path 1 and Path 2 are superficial or not.
Let’s say today’s version of your future might involve running a company, and your alternate reality version is becoming a therapist. Those feel (and are) meaningfully different paths, but I challenge you to find the similarities. In this example, maybe they both involve:
Deep, one-on-one relationships
Teaching/guiding
Helping people navigate change
Independence
Building things from scratch
You might discover that you’re attached to a particular vehicle (build a company!) instead of the thing you actually want (build something from scratch!).
When Path 1 and Path 3 are easy to see, but you struggle to imagine Path 2 at all
This is also data! What it could mean is that you aren’t choosing your current path because you love it; you’re choosing it because it’s too difficult to imagine a realistic alternative.
A lack of options is different from a genuine preference, and this exercise helps distinguish between the two.
When Path 3 looks suspiciously simple
You might expect that if money didn’t matter, you’d be living some extravagant fantasy.
Instead, you might discover you just want things like:
Lots of time with friends or family
Time to read, make art, or pursue a hobby
Being in nature
A small community
To only work on something that makes an impact
The gap between that simplicity and the complexity of your current life can be…revealing. And it’s not because simplicity is inherently better, but rather because it forces the question: If these are the things I say matter most, and they’re so simple, why are they receiving so little of my time now?
When you find similarities in all three paths
Commonalities between the paths tell you something important! Maybe all three involve creativity. Maybe all three involve community. Maybe all three involve autonomy. So while the specifics change, the themes don’t. That’s a major signal of what’s at the heart of your life, dreams, and desires.
I suppose for students, this Odyssey Plan exercise can help them concretely plan for a specific future. But for the rest of us, it’s just helpful to unpack the assumptions that have perhaps been secretly designing our lives!
Over to you…
Did you try this exercise? What about any of your imagined paths surprised you?
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