A toolkit, not a recipe. Most decisions don’t need any of this — the point is knowing which ones do, and reaching for the right tool when they show up.
Step 1 — Triage (always do this)
Before anything else, classify the decision:
- Reversible? One-way door (hard/impossible to undo) or two-way door (cheap to reverse)? Two-way doors get a minute of thought, not a week.
- Stakes? Will this matter in a year? In ten? Or is it noise that just feels big right now?
- Time pressure real? Most “urgent” decisions have more slack than they appear. Ask: what actually happens if I decide this tomorrow? Next week?
- Whose decision is this? If it’s not actually yours to make alone, stop and figure out who else is in it.
Default: if it’s reversible and low-stakes, just decide and move on. Optimization here is the trap. The rest of this doc is for the ones that survived triage.
Step 2 — Core walkthrough (medium/high-stakes)
Run these in order. Skip steps that don’t apply.
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Frame the actual question. Write the decision as a single sentence. If you can’t, you don’t understand it yet. Watch for:
- Hidden binaries (“should I do X?” when the real question is “what should I do about Y?”)
- Wrong altitude (debating the tactic when the strategy is the real choice)
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Widen the options. If you have two options, you probably have a false dilemma. Force a third. Ask: “what would I do if neither of these were available?” Also worth: “what would I tell a friend in this exact spot?”
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Name the assumptions. What would have to be true for option A to be the right call? For B? Which of those am I just guessing? Can I cheaply test the guess before committing?
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Pre-mortem. Imagine it’s a year from now and this decision went badly. Write the story of how. The failure modes you can articulate are the ones you can defend against.
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Check the gut. After all the analysis, what does your gut say? If gut and analysis disagree, that’s information — usually one of them is missing context the other has. Don’t auto-override either.
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Decide. Set a review date. Write down the decision, the reasoning, and when you’ll revisit. The review date matters more than people think — it’s how you learn whether your decision process is any good.
Step 3 — Specialty tools (pull when relevant)
- Expected value — for probabilistic bets.
P(win) × value(win) − P(lose) × value(lose). Useful when you can roughly quantify; dangerous when you fake the numbers. - 10/10/10 — for emotionally charged decisions. How will I feel about this in 10 minutes? 10 months? 10 years? Cuts through recency bias.
- Regret minimization — for big life decisions. Project yourself to 80. Which choice do you regret not making? (Bezos’s original Amazon decision.)
- Eisenhower matrix — for prioritization, not decisions per se. Urgent×Important grid. Most “decisions” about what to work on are actually triage problems in disguise.
- Opportunity cost — what am I not doing by doing this? Especially for time commitments.
- Reversibility test — if cheap to undo, just try it. Bias toward action on two-way doors.
- “Hell yes or no” — for optional commitments. If it’s not a clear yes, it’s a no. (Derek Sivers.) Use carefully — guards against overcommitment, but can also be an excuse for inertia.
Common traps
- Analysis as procrastination. More research feels productive but past a point it’s avoidance. Set a decision deadline.
- Sunk cost. What you’ve already spent is irrelevant to whether to continue. Only the marginal next step matters.
- Status quo bias. “Don’t decide” is itself a decision, with all the same consequences. Default-no is still a no.
- Optimizing the wrong thing. Easy to optimize the metric you can measure (salary, hours) instead of the one that matters (energy, time with Max, learning rate).
- Solo on a non-solo decision. Big ones touching Alana, Max, family logistics — loop her in before, not after, the analysis.
Log
Form a decision log. Reviewing past decisions is how a framework gets better.
- Template:
YYYY-MM-DD — [decision] — [reasoning in one sentence] — [review date]