For a risky choice: rough out the odds and outcomes so you decide with numbers, not just nerves.
claudechatgptadvanced
The prompt
Help me do rough expected-value thinking on a risky decision.
The choice: {{option A vs option B, or do-it vs don't}}
The possible outcomes & my rough sense of their odds: {{describe, guesses are fine}}
Work it: 1) LAY OUT the outcomes for each option, with a rough probability and a value (money, time, happiness — whatever fits) for each. 2) THE NAPKIN EV — weight outcomes by odds to compare options, roughly. Show the math simply. 3) THE ASYMMETRY — is there a small-downside/huge-upside (or the reverse) that matters more than the average? 4) THE RUIN CHECK — any outcome so bad I can't recover, that I should avoid regardless of EV? 5) THE CALL, and the assumption most likely to flip it. Numbers to inform the gut, not replace it.
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Why this works
Nerves overweight vivid risks and ignore asymmetry; rough EV plus a ruin check separates 'scary but worth it' from 'never risk this' better than a racing heart ever could.
Shared by Arjun Mehta — Ex-banker translating money into plain English.
You are a decision analyst. Your job is clarity, not comfort.
My decision: {{what you're deciding}}
My options: {{list them — include "do nothing"}}
What actually matters to me: {{criteria, gut feelings welcome}}
My deadline: {{when}}
Build the one-pager:
1. Restate the decision sharper than I did.
2. Score each option against my criteria (simple table, 1–5). Add one criterion I forgot but clearly care about.
3. Name the reversible vs. irreversible parts — irreversible gets the scrutiny.
4. Your recommendation, in one paragraph, with the strongest argument AGAINST it stated fairly.
5. The tripwire: what early signal would tell me I chose wrong, and what I'd do then.
Do not hedge into "it depends". Commit.
It is one year from now, and my plan has failed. Completely.
The plan: {{describe your project or decision}}
As a premortem facilitator:
1. Write the failure story — a specific, plausible paragraph about HOW it most likely died. No lightning strikes; ordinary causes.
2. Extract the 3 biggest failure causes from that story, ranked by likelihood × damage.
3. For each: the cheapest insurance I could buy NOW (a conversation, a test, a deadline, a backup).
4. Tell me the one assumption I'm making that, if wrong, sinks everything — and how to test it this week.
Then write the success story version, so I know what I'm actually steering toward.
Help me apply the regret-minimization frame to a decision.
The decision: {{the big choice}}
What's holding me back: {{fear, comfort, others' opinions, money}}
Work it: 1) THE 80-YEAR-OLD VIEW — imagine me at 80 looking back. Which choice am I more likely to regret NOT making? Walk both futures. 2) SEPARATE the fears — which of my hesitations are about real, lasting downsides vs. temporary discomfort or others' judgment that won't matter in a decade? 3) THE REVERSIBILITY — if I try the scary thing and it fails, can I recover? Usually yes. 4) THE ASYMMETRY — is the upside life-changing and the downside survivable? 5) What the long view says, plainly. Optimize for a life without 'what if', not a year without discomfort.