Pressure-test a decision with a pre-mortem

Prompt

Run a pre-mortem on a decision I'm about to make.

The decision: [what you plan to do, e.g. quit my job to freelance full-time]
My goal: [what success looks like, e.g. matching my salary within a year]
Context: [constraints and facts, e.g. 6 months of savings, two clients lined up]

Imagine it's [time frame, e.g. one year] from now and the decision has clearly failed. Looking back:

1. List the 7 most plausible reasons it failed. Cover different kinds of cause: money, time, people, demand, execution and my own blind spots. Make each reason specific to my situation, not generic advice.
2. Rank them by likelihood × impact, top 3 first.
3. For each of the top 3, give an early warning sign I could spot within the first month or two, and one cheap thing I can do now to make it less likely.
4. Suggest 2 tripwires: clear, measurable signals that should make me stop or change course.
5. Make the strongest honest case for not doing this at all, then say what would have to be true for that case to be right.

Be direct. I want to find the problems now, not be reassured.

If any detail in square brackets is still unfilled, ask me for those details in one short message before you start.

Variation: Compare options

Help me choose between two options.

My goal: [what success looks like, e.g. a junior developer job within a year]
Option A: [first option, e.g. a 12-week coding bootcamp]
Option B: [second option, e.g. self-study while keeping my job]
What matters most to me: [your priorities, e.g. cost, speed, keeping my income]

1. Compare the options in a table on cost, time to results, risk, how reversible each choice is, upside, and anything else that matters for this goal.
2. Name the assumption each option depends on most, and how I could test it cheaply this week.
3. Tell me which you'd pick given my priorities, and why, in 3 sentences.
4. Tell me what new information would change your recommendation.

If there's a clearly better third option I haven't considered, mention it briefly at the end.

If any detail in square brackets is still unfilled, ask me for those details in one short message before you start.

Variation: Quick gut check

Give me a quick, honest gut check on a decision.

The decision: [what you plan to do, e.g. take a job that pays more but has a longer commute]
Why I'm leaning toward it: [your main reason, e.g. 20% more pay]

In under 150 words:
- The 3 biggest risks or downsides I might be underweighting.
- The one question I should be able to answer before I go ahead.
- Your honest read in one sentence: go, wait or rethink, and the main reason.

If any detail in square brackets is still unfilled, ask me for it before you answer.

Open in

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• DeepSeek ★Step-by-step reasoning(copies the prompt, then opens the site)