life-premortem

Life Premortem Skill

Optimism is required to start big things and dangerous once you've started — because a mind committed to a plan goes blind to how it fails. The premortem flips that: instead of asking "what might go wrong?" (which the committed brain swats away), it says "it's a year from now and this failed — tell me the story of how." That small framing change unlocks honesty the forward-looking question can't. This skill runs it at life scale — the move abroad, the marriage, the career pivot, the sabbatical, the year's resolutions — turning a vivid failure story into a short list of real risks and the often-cheap things that would prevent them.

What This Skill Produces

• A failure narrative: a specific, vivid story told from one year (or the relevant horizon) in the future, in which the thing went wrong — concrete, not a risk list in disguise
• An extracted risk list: the real failure modes the story reveals, sorted by likelihood × how much they'd hurt
• Cheap preventatives: for each real risk, the small thing available now that would defuse it (most disasters have a five-dollar prevention that feels stupid to do and obvious in hindsight)
• Early-warning signs: the specific things that, if you notice them in month 3, mean the failure story is starting — so you can course-correct instead of discovering it at the end

Required Inputs

Ask for (if not already provided):

• The big thing being committed to, and the horizon that matters (a year? the end of the sabbatical? the first year of the marriage?)
• Why it matters and what "success" would look like — you can't fail a goal you haven't named
• What the user is quietly worried about but talking themselves out of (this is often the real risk, pre-rationalized away)
• What's reversible vs not, and what's already committed

Framework

1. Tell the failure as a story, not a list. The magic is in the narrative frame: "It's a year later. The move to Lisbon fell apart. Walk me through how it went." A story recruits honesty and detail that "list your risks" never does — the committed brain will defend a plan but will happily narrate a hypothetical failure. Make it vivid and specific.
2. Mine the story for the real risks. The narrative will surface failure modes the user actually believes in (the isolation, the money running out faster than planned, the relationship not surviving the stress) as opposed to the generic risks they'd list defensively. Extract those, rank by likelihood × pain.
3. Find the stupidly-cheap preventative for each. Most real risks have a small, almost embarrassing prevention: the friend you'd have called before it got bad, the three-months-more savings, the conversation you'd have had, the trial run. The gap between the cheap prevention and the expensive failure is the whole ROI of this exercise.
4. Name the early-warning signs. For each risk, the observable tell that the failure story is beginning — the month-3 signal (the loneliness that isn't lifting, the burn rate that's off, the resentment building). Catching the story early is how you rewrite it; the premortem hands you the alarms.
5. Keep it a bet, not a veto. The premortem de-risks; it doesn't talk the user out of brave things. The output ends by weighing the (now-mitigated) risks against the reason for doing it — because the point is to go in clear-eyed, not to not go.