Free Decision Making Prompts

My decision: [PASTE]. Tell me whether it's a one-way door or a two-way door. Probe: 1) cost to reverse in time, money, reputation, 2) what info I'd gain by deciding fast, 3) what info I'd gain by waiting. If two-way, what's blocking me from deciding in the next 24 hours? If one-way, what's the homework I owe before deciding?

Run an expected-value calc on this choice: [PASTE]. For each option, estimate: probability of best case × payoff, probability of base case × payoff, probability of worst case × cost. Surface where my probability estimates are guesses vs grounded. End with the option with highest EV and the assumption most worth testing first.

Apply the 10-10-10 rule to my decision: [PASTE]. 1) How will I feel about it in 10 minutes? 2) In 10 months? 3) In 10 years? Identify which horizon I'm overweighting and which I'm under-weighting. End with the choice my 10-years-from-now self would respect.

Walk me through filling out a decision-journal entry for this decision: [PASTE]. Cover: 1) the choice made, 2) the alternatives considered, 3) what I expected to happen and probabilities, 4) emotional state, 5) timing constraint, 6) the date to review and what success/failure would look like. End with the review-date question.

I'm stuck on this decision: [PASTE]. Diagnose the real blocker. Candidates: insufficient information, irreducible uncertainty, fear of judgment, fear of regret, competing values, identity threat. End with the option-shaped question I should answer first, and the decision deadline I'll set so I stop spinning.

My decision: [PASTE]. The two values pulling: [PASTE]. Help me name the trade honestly. 1) Which value am I tempted to over-weight and why. 2) Which I'm under-weighting. 3) The version of the choice that respects both partially. 4) The version that picks one cleanly. End with the choice I'd respect myself for at age 70.

Big decision: [PASTE]. Help me build a ladder of smaller, more reversible steps that produce the same information. For each rung: time/cost, info gained, risk to relationships/reputation. End with the 1-2 rungs I should climb before the big call.

My decision: [PASTE]. Apply Bezos's regret minimization. 1) The regret of doing it and failing. 2) The regret of not trying at all. 3) Which would I be more able to live with at 80. 4) What story I'd tell about the choice in 20 years. End with the choice and the precommitment that keeps me from re-litigating it.

Here's a decision I'm seeking input on: [PASTE]. Honestly: am I asking for advice or seeking permission? Identify the tells. If permission: who am I really asking and why does their approval matter? If advice: what specific input would actually change my mind? End with the cleaner question to ask.

Let me consult an imagined panel of three trusted voices on this decision: [PASTE]. Pick voices with different styles (e.g., a pragmatist, a philosopher, a friend who knows me). For each: their question, their advice, their warning. End with the synthesis - what they'd agree on, where they'd disagree, and what I'd do.

Decision to commit: [PASTE]. Help me pre-set kill criteria so I don't get stuck escalating commitment. 1) The 2-3 measurable signals that mean "stop". 2) The check-in dates. 3) The person who can call it on my behalf if I'm in denial. 4) The off-ramp message I'd send. End with the trigger I'm most likely to ignore.

I want to "sleep on it" before deciding: [PASTE]. Make the night productive. 1) The single question I'll write down before bed. 2) The 5-minute reread tomorrow morning. 3) The deadline tomorrow by which I must decide. 4) The rule against checking opinions overnight. End with the morning question that resolves it.

My current default in [SITUATION] is [PASTE]. Audit whether it's still serving me. 1) Why I chose it originally. 2) What has changed since. 3) What an active choice today would look like, even if it's the same default. 4) The trigger that would make me re-evaluate. End with the version of the default I'd consciously re-adopt.

My hourly value (or aspiration): [PASTE]. Tasks I'm doing weekly: [PASTE]. For each, decide: keep (it's strategic or joyful), outsource (cost vs value), or eliminate. Justify in one line. End with the 1 task I should outsource this month and the rough budget.

I keep re-opening this decision after making it: [PASTE]. Walk me through closing the door. 1) The reason I made the choice (in my words at the time). 2) What new info, if any, has actually emerged. 3) The cost of re-opening vs accepting. 4) The mantra or precommitment to use when the doubt returns. End with the rule for when I'd legitimately revisit it.