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
- 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.
- 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.
- 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.
- 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.
- 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.
Output Format
## The failure story (one year on)
[A vivid, specific narrative of how this went wrong — told as a story]
## The real risks it revealed
| Risk | Likelihood | How much it'd hurt | (ranked) |
## The stupidly-cheap preventative for each
[Risk → the small thing available now that defuses it]
## Early-warning signs (your month-3 alarms)
[The observable tells that the failure story is starting]
## Still worth it?
[The mitigated risks weighed against why you're doing this — go in clear-eyed]
Quality Checks
Anti-Patterns
Related
[[premortem-assassin]] is the project/plan version; [[future-self-interview]] is the
hopeful mirror; [[the-time-capsule]] to log the predictions; [[franklin-decision-ledger]]
and [[regret-minimizer]] for the decide-or-not layer.
1---2name: life-premortem3description: Write the failure story of your year, relationship, move, or big life bet in advance — imagine it's a year later and it went wrong, tell that story vividly, then mine it for the real risks and the cheap things that would have prevented them. Use when someone says 'I'm about to make a big life change', 'what could go wrong with this', 'de-risk my year', or is committing to something large and irreversible. Produces the failure narrative, the extracted risk list with preventatives, and the early-warning signs to watch. The life-scale sibling of a project premortem.4---5
6# Life Premortem Skill
7
8Optimism is required to start big things and dangerous once you've started —
9because a mind committed to a plan goes blind to how it fails. The premortem flips
10that: instead of asking "what might go wrong?" (which the committed brain swats away),
11it says "it's a year from now and this failed — tell me the story of how." That small
12framing change unlocks honesty the forward-looking question can't. This skill runs it
13at life scale — the move abroad, the marriage, the career pivot, the sabbatical, the
14year's resolutions — turning a vivid failure story into a short list of real risks
15and the often-cheap things that would prevent them.
16
17## What This Skill Produces
18
19- A **failure narrative**: a specific, vivid story told from one year (or the relevant
20 horizon) in the future, in which the thing went wrong — concrete, not a risk list
21 in disguise
22- An **extracted risk list**: the real failure modes the story reveals, sorted by
23 likelihood × how much they'd hurt
24- **Cheap preventatives**: for each real risk, the small thing available *now* that
25 would defuse it (most disasters have a five-dollar prevention that feels stupid to
26 do and obvious in hindsight)
27- **Early-warning signs**: the specific things that, if you notice them in month 3,
28 mean the failure story is starting — so you can course-correct instead of
29 discovering it at the end
30
31## Required Inputs
32
33Ask for (if not already provided):
34- The big thing being committed to, and the horizon that matters (a year? the end of
35 the sabbatical? the first year of the marriage?)
36- Why it matters and what "success" would look like — you can't fail a goal you
37 haven't named
38- What the user is quietly worried about but talking themselves out of (this is often
39 the real risk, pre-rationalized away)
40- What's reversible vs not, and what's already committed
41
42## Framework
43
441. **Tell the failure as a story, not a list.** The magic is in the narrative frame:
45 "It's a year later. The move to Lisbon fell apart. Walk me through how it went."
46 A story recruits honesty and detail that "list your risks" never does — the committed
47 brain will defend a plan but will happily narrate a hypothetical failure. Make it
48 vivid and specific.
492. **Mine the story for the real risks.** The narrative will surface failure modes the
50 user actually believes in (the isolation, the money running out faster than planned,
51 the relationship not surviving the stress) as opposed to the generic risks they'd
52 list defensively. Extract those, rank by likelihood × pain.
533. **Find the stupidly-cheap preventative for each.** Most real risks have a small,
54 almost embarrassing prevention: the friend you'd have called before it got bad, the
55 three-months-more savings, the conversation you'd have had, the trial run. The gap
56 between the cheap prevention and the expensive failure is the whole ROI of this
57 exercise.
584. **Name the early-warning signs.** For each risk, the observable tell that the
59 failure story is beginning — the month-3 signal (the loneliness that isn't lifting,
60 the burn rate that's off, the resentment building). Catching the story early is how
61 you rewrite it; the premortem hands you the alarms.
625. **Keep it a bet, not a veto.** The premortem de-risks; it doesn't talk the user out
63 of brave things. The output ends by weighing the (now-mitigated) risks against the
64 reason for doing it — because the point is to go in clear-eyed, not to not go.
65
66## Output Format
67
68```
69## The failure story (one year on)
70[A vivid, specific narrative of how this went wrong — told as a story]
71
72## The real risks it revealed
73| Risk | Likelihood | How much it'd hurt | (ranked) |
74
75## The stupidly-cheap preventative for each
76[Risk → the small thing available now that defuses it]
77
78## Early-warning signs (your month-3 alarms)
79[The observable tells that the failure story is starting]
80
81## Still worth it?
82[The mitigated risks weighed against why you're doing this — go in clear-eyed]
83```
84
85## Quality Checks
86
87- [ ] The failure is told as a specific story, not a risk list wearing a narrative hat
88- [ ] The extracted risks are ones the user actually believes, including the quiet
89 worry they'd rationalized away
90- [ ] Each real risk has a concrete, cheap-now preventative
91- [ ] Early-warning signs are observable and time-anchored (you'd notice them by
92 month 3), not vague
93- [ ] It ends by weighing risk against reason — de-risking, not vetoing the dream
94
95## Anti-Patterns
96
97- [ ] Do not let it become a generic risk checklist — the story frame is the engine;
98 without it the honesty doesn't come
99- [ ] Do not use it to kill the user's brave thing — the goal is going in clear-eyed,
100 and a mitigated risk is a reason to prepare, not to quit
101- [ ] Do not surface only comfortable risks — the quiet, pre-rationalized worry is
102 usually the real one; go there
103- [ ] Do not skip the cheap-preventative step — a risk named without a defuse is just
104 anxiety
105- [ ] Do not confuse this with catastrophizing — it's one structured story with exits,
106 not a spiral
107
108## Related
109
110[[premortem-assassin]] is the project/plan version; [[future-self-interview]] is the
111hopeful mirror; [[the-time-capsule]] to log the predictions; [[franklin-decision-ledger]]
112and [[regret-minimizer]] for the decide-or-not layer.
Mohit Aggarwal