What's next
Sketch three possible futures
A thinking exercise to see more than one way forward, and learn from how each one feels
Write three quite different five-year paths for yourself, including one you'd follow if money didn't matter, and notice how you react to each.
- About 45 minutes
- Just you
- Once a year
- Worksheet
Why this can work
Most people carry one version of their future around and judge it against nothing. Sketching three very different paths loosens that single story, and your reactions, the one you keep defending, the one that tires you just reading it, tell you more than a list of pros and cons. You don't have to pick one; comparing is how you learn what you want.
Read moreHow to write an odyssey plan
You’ll come away with three rough five-year sketches and a sense of which one pulls at you.
- Set aside 45 minutes and a blank page.
Somewhere you won't be interrupted. This works better as a sketch than an essay: bullet points, a rough timeline, even a doodle.
- Draft your three futures.
One is where your current path leads if you keep going. One is what you'd do if that path vanished tomorrow. One is what you'd do if money and other people's opinions didn't matter. For each, give it a short title and a few lines on where you'd be in five years and what a normal week looks like.
Stays in this browser only. Nobody else sees it.
Tip: Make them genuinely different. If the second is the first at another company, push further.
- Notice your reaction to each.
Read them back. Which one did you want to keep writing? Which made you tired? Then rate each quickly: how much you like it, how confident you feel you could do it, and whether it fits what matters to you.
- Pull out the questions each path raises.
What would you need to find out before any of these felt real? Would I like the day-to-day? Could I afford the first year? Who has done this? Those questions are more useful right now than a decision.
- Read them aloud to someone you trust.
A friend, partner or mentor. Watch where your voice changes. Ask what they noticed rather than which one you should choose.
You“Which one did I sound most alive describing?”
Good times to repeat it: once a yearwhen you feel stuckbefore a big career decision
Making it work for you
Every workplace is different. Here’s what to think about before you start, and what might get in the way.
Things to think about
It's rarely the whole plan, but it often contains one true ingredient, a kind of work or a setting, that you could bring into a more practical path.
What might make this harder
Start with path two: if your current job disappeared tomorrow, what would you do? A forced constraint makes the other paths easier to imagine.
Questions people ask
What is an Odyssey Plan?
An exercise from Bill Burnett and Dave Evans's book Designing Your Life. You sketch three different five-year versions of your life and compare them, to widen your options rather than to pick one right away.
How do I imagine different career paths for myself?
Write three that are genuinely different: where your current path leads, what you'd do if it disappeared, and what you'd do if money didn't matter. Then notice which one pulls at you, and why.
What if I don't know what I'd do if money didn't matter?
Start small. Think about what you'd spend a free week doing, or what you loved before work got busy. A rough answer is enough to learn from.
Why this works, and where it comes from
The hunt for the one right answer tends to freeze people. Every option gets compared to an imaginary perfect one, and nothing measures up. Sketching three futures turns one impossible decision into a comparison you can actually make. You stop asking whether a path is right and start asking which one pulls at you, and why.
This adapts the Odyssey Plan from Bill Burnett and Dave Evans's book Designing Your Life. In their version you write three alternative five-year lives, give each a title, list the questions each raises, and gauge each on resources, how much you like it, how confident you feel about it and whether it hangs together with what you believe. The three here follow their shape: the life you're on, the one you'd build if it vanished, and the one you'd live if money and appearances didn't matter.
The real output isn't the plans, it's your reactions. People are often surprised by which future they keep defending, or that the sensible one leaves them cold. Those reactions are some of the most honest information you have about what you want, and they're easy to miss when you only think in your head. Reading the three aloud to someone helps; you tend to hear your own enthusiasm before you're ready to admit it.
It's the wrong exercise when a choice is already in front of you, a layoff or an offer with a deadline. Then you need to compare the real options, not invent new ones. And no sketch settles anything on its own. The questions each path raises are the next step, which usually means talking to someone who lives one of them or trying a small piece of it.
Other simple things to consider
What to do next
More in What's next
Know what you actually want
Do it with Truest and it goes on your permanent record, in a Career Vault your employer doesn’t own.
See how Truest worksAlready a member? Log in- The longer sessionCareer Compass is the guided session for working out what you want next.
- A living page in your VaultKeep it as one page you add to, next to your reviews and your files.
- A reminder beforePut it on your calendar and Truest reminds you before it starts.
Read this alongside your role page
Tell Truest what you’re dealing with
We read every one, and we write guides for the things that come up most. Leave your email if you’d like to hear when we do.
Written by Truest, based on Designing Your Life (Bill Burnett and Dave Evans). Last updated September 25, 2026. We sell a career membership; where that’s relevant above, we say so.