Three Five-Year Plans, or One Plan With Three Salaries?
Stanford's official Odyssey worksheet has one instruction almost everyone skips: make each of the three plans wildly different. Most engineers write three price tiers of the same life instead. Here is the incompatibility test and a prompt that attacks your plans.
- #career
- #international
- #life-design
- #planning
The official Odyssey worksheet from Bill Burnett and Dave Evans — the Stanford professors behind Designing Your Life — carries one line that decides whether the exercise works at all: "The goal is to make each Odyssey wildly different." Almost nobody obeys it. When I watch Brazilian engineers do this, I get three plans that are the same plan with the salary knob turned: senior here, senior at a gringo company, staff at a gringo company. Three price tiers, one life. There is no decision inside that, so there is nothing to learn from it.
What the exercise actually is
Burnett and Evans co-founded the Stanford Life Design Lab, which still ships Odyssey Planning as a video series and an edX module. The exercise is three separate five-year plans, one per prompt:
- Life One — the trajectory you are on now, or the idea you have been sitting on for a while.
- Life Two — what you would do if Life One stopped being available tomorrow.
- Life Three — the wildcard: what you would do if money and image were no object.
The elements the blog-post versions quietly drop are the ones doing the work. The worksheet distributed by Colorado State's Career Management Center, licensed from Burnett, Evans and Stanford, spells all four out. Every plan needs a six-word title; a drawn year 0→5 timeline that includes non-career bucket-list events, not only job moves; two to three questions the plan addresses — and the worksheet is explicit that these are curiosities you might satisfy by living that way for five years, not questions about whether the plan is feasible; and a dashboard of four gauges: Resources (do you have the time, money, skill and contacts?), I Like It (cold→hot), Confidence (empty→full), and Coherence (is this consistent with your Workview and Lifeview?).
Coherence is the gauge everyone cuts, and it is the one that keeps "wildly different" from turning into "random".
The Brazilian version, written to conflict
For a dev or EM based here, three plans that genuinely cannot coexist look something like this.
Life One — you grow where you are. Salary in reais, a promotion ladder you can actually see, a network built face to face, Portuguese all day. The curiosity: how far does local seniority really take me?
Life Two — Brazil stops being your market. You are hired by a company abroad while still living here: USD or EUR, a contract through an EOR, your calendar bent to overlap someone else's timezone. The curiosity: can I hold a foreign performance bar, in English, every day, with no office to carry me?
Life Three — you leave the track. Money is not the constraint: your own product, teaching, an AI practice with your name on it, or physically moving countries. The curiosity: is the part I love the engineering, or the building?
Treat those as examples, not as your answer. Which three you pick matters much less than whether they can be true at the same time.
The test: same first step, same plan
This is what I would add to the worksheet. For each plan, write the one concrete thing you would start in the next six months. Then put the three first steps side by side.
If two of them are the same action, you have two plans, not three.
"Get my English up, build a portfolio, apply abroad" funds all three paths at once — which means it is not a plan, it is table stakes. Do it regardless. A real Life Two first step spends something Life One needs: shifting your day to overlap US hours costs you exactly the in-person visibility that gets you promoted locally. A real Life Three first step burns the thing that is compounding in Life One — the specialization you would stop deepening the month you start.
Use the model as the adversary, not the author
The obvious move is to ask an LLM to write your three futures for you. Don't. Ask a model for three five-year plans for a Brazilian engineer and it will regress to the median of everything it ever read about Brazilian engineers, and hand you three flavors of one safe path — the exact failure the exercise exists to prevent. The plans have to come from you; you are the only one holding the inputs.
Where a model beats a friend: it will keep hammering a plan long after a friend has started being kind about it. So hand over the three you wrote and ask it to break them.
You are stress-testing three five-year plans I already wrote. You are not writing
plans for me and you are not encouraging me. Assume each plan is wrong until the
evidence says otherwise.
MY CONTEXT
- Role, level, years of experience:
- Where I live; my currency and current salary:
- Savings runway in months; who depends on my income:
- English, honestly: reading / writing / speaking:
- Hours per week I can genuinely protect for this:
MY THREE PLANS (six-word title + 3-4 sentences each)
- Plan 1, current trajectory:
- Plan 2, if plan 1 disappeared:
- Plan 3, money and image no object:
STEP 1 - INCOMPATIBILITY CHECK. Before anything else: are these three plans, or
one plan wearing three hats? Compare them by the resources they consume and the
skills they compound. If any two could be pursued with the same six months of
effort, name those two and stop. Tell me what would have to change for them to
be genuinely incompatible, then wait for my rewrite.
STEP 2 - Then, for each plan, in this order:
a) What would have to be true for this to work? List the assumptions and tag each
one "I control this" or "the market controls this".
b) What would I have to learn, and how would a hiring manager abroad verify that
I learned it?
c) What does it cost - money, time, relationships, and the optionality I give up.
Name what this plan makes harder later.
d) The cheapest test in the next 90 days that could prove this plan wrong. Not a
step forward: a falsification.
STEP 3 - Fill the four gauges per plan and justify each with one line: Resources
(0-100), I Like It (cold-hot), Confidence (empty-full), Coherence (0-100, fit
with how I want to work and live).
STEP 4 - Tell me which gauge I am most likely lying to myself about, and what in
my own answers made you think so.
RULES
- Never invent facts about my situation. If you need something, ask me for it.
- No motivational language. Be specific or say nothing.
- If a plan cannot be falsified within 90 days, call it a wish, not a plan.
- Close with one paragraph: what you would test first if this were your life,
and what you would refuse to do.
Feed it real numbers — actual salary, actual runway, actual English level, the timezone you could survive for two years. Vague inputs buy you a vague attack.
Today
Write three six-word titles. Nothing else — no timeline, no gauges, no prompt yet. Six words each, and they have to describe three lives you could not possibly live at the same time. If you cannot get three that conflict, that is the finding: you have one plan, and the next five years are already decided.
Sources
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