Questions to Ask Yourself Before Making a Decision
For anyone who has made the same choice three times this week and unmade it each time, whether it is a job offer, a move, a relationship or a commitment that will be hard to walk back. The 47 questions run in the order a decision usually does: pin down the choice and its deadline, tell what you want from what you feel you ought to want, widen the options, count the cost and the risk, weigh the people advising you, then look ahead to living with it. Write your answers down, and expect a few to send you off to check a fact or ask someone before you can finish.
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The questions
Each question, and why to ask it
The choice
What exactly am I deciding, in one sentence?
Why ask it
Write it as a choice between named things: 'take the Denver job or stay where I am', not 'what to do about work'. If the sentence will not come out clean after three tries, the going back and forth is about the question itself, and that is the thing to settle first.
When do I actually have to decide by, and who set that date?
Why ask it
A date printed on an offer letter, a lease renewal or an enrollment form belongs to someone else, so ask them how firm it is before you let it rush you. One that comes from your own impatience, or from a person who would simply like an answer, can usually move.
What happens if I decide nothing?
Why ask it
Doing nothing is a choice with a result of its own: the offer lapses, the lease rolls over, the relationship carries on as it is. Describe that result in as much detail as the others so it gets weighed on purpose instead of winning by default.
Is this one decision, or several I have tied together?
Why ask it
'Should we move in together' holds at least three: where to live, how to split the money, and what it means for the two of you. Pull them apart and one is often already settled, which leaves a smaller question than the one keeping you awake.
Is this mine to decide alone?
Why ask it
List who has to live with the result: a partner, children, a co-signer, a business partner. Anyone on that list should hear about it while you can still be moved, since being told afterward feels very different from being asked.
What do I not know yet that I could find out this week?
Why ask it
Make the list, then mark every item a phone call, a visit or an hour with a spreadsheet would answer, and go get those before thinking any further. Whatever is left cannot be known in advance by anyone, so stop treating it as homework.
Will this still matter in five years, or mostly for the next few months?
Why ask it
The answer sets how much of your attention the decision has earned. Something you will barely remember by next summer deserves an evening, and giving it a month is its own kind of cost. Save the long deliberation for the choices that set the shape of your days.
How long have I been stuck on this, and when did I last learn anything new about it?
Why ask it
If the last three rounds of thinking turned up nothing new, a fourth will not either. At that point the decision needs a missing fact, a small trial or a date, and more hours of weighing the same two lists only wears you down.
What I want
If nobody would ever find out what I chose, which would I pick?
Why ask it
This takes the audience away. When the private answer differs from the one you have been leaning toward, the gap is made of how the choice would look, and you can decide how much that is worth to you.
Which option do I think I should want, and whose voice is that 'should' in?
Why ask it
Usually it has an owner: a parent, a group of friends all taking the same path, a plan you made at twenty-two. Inherited shoulds can still be right. Name the owner anyway, then ask whether you would have reached the same view on your own.
What does my gut say when I picture saying yes, and when I picture saying no?
Why ask it
Catch the first reaction before the reasoning arrives: relief, dread, excitement, a sinking feeling. Treat it as one piece of evidence, not a verdict. Relief at the thought of saying no is worth a follow-up about what exactly you would be glad to escape.
If I tossed a coin, which side would I be hoping for while it was in the air?
Why ask it
You are not agreeing to obey the coin. Assign the options, toss it for real, and notice whether you feel a small lift or a small drop when it lands. Wanting best of three tells you the same thing.
What am I afraid of in each option?
Why ask it
Write one fear under each choice, then sort them. 'The work might bore me' is about the option and can be checked. 'I might not be good enough' is about you, and it will come along whichever way you go, so it should not get a vote.
Am I heading toward something, or mostly getting away from something?
Why ask it
Getting away is a fair reason to act, but it only tells you what to leave. If most of the pull is escape, check that the new option actually lacks the thing you are escaping, and is not simply the nearest door.
What matters most to me here, and which option serves it best?
Why ask it
Pick three things, such as security, time with family, room to grow or being near certain people, and force them into an order. Score each option against the first one only. If that is a tie, go to the second, and notice how rarely you need the third.
Which option fits the person I am trying to become?
Why ask it
Describe that person in a line or two first: how they spend a weekday, what they are known for, who they are around. Then hold each option against the description. A choice can pay well, be easy to defend and still lead away from it.
Would I choose the same thing if I were not tired, hurt or angry right now?
Why ask it
A choice made in the worst week of the year tends to be about the week. If a rested version of you would answer differently and the deadline allows it, wait for that version. If the answer holds on a good day too, the mood is not what is deciding.
Options
Which options have I left off the list?
Why ask it
Stuck decisions are often a yes or no on one thing. Push the list to five, including the ones that sound silly or expensive. The useful one is frequently a blend of two, and it only appears once the obvious pair is on paper.
What are the pros and cons of each option, and which two or three carry real weight?
Why ask it
Make the lists, then cross out every line that would not change your mind alone. Counting what is left misleads, because one heavy item, such as living a flight away from your kids, can outweigh six light ones. Circle the heavy ones and decide on those.
Could I try this on a small scale before I commit to all of it?
Why ask it
Rent in the new city for a month before selling the house, take one course before changing fields, make a long visit before a long-distance move. Ask the other side whether a trial is possible. It is often not offered because nobody asked for it.
Could I do both, or one now and the other later?
Why ask it
The 'or' is sometimes an assumption nobody tested. Find out whether the second option really expires. If it will still be open next year, you are choosing an order, and that is a much lighter decision than choosing a life.
If the option I am leaning toward disappeared tomorrow, what would I do?
Why ask it
Your answer shows the real runner-up. If it comes easily and does not feel like a loss, the favorite may be ahead only because it was the first one you looked at closely. If you feel a jolt, that counts as an answer too.
What would have to be true for each option to be the right one?
Why ask it
This swaps an argument for a checklist. Under each option write the conditions: the pay covers the rent, the relationship survives the distance, the new manager is as good as the interview suggested. Then go and find out which conditions hold.
Have I asked for the change that would make one option clearly better?
Why ask it
A stuck choice sometimes hinges on a single term: the start date, the length of the contract, who covers which cost, how long you have to answer. Ask for it once, in one clear sentence, and base the decision on the reply you get instead of the one you imagined.
Cost and risk
What will each option take from me every week once the novelty has worn off?
Why ask it
The first month is not the cost. Count the commute, the upkeep, the hours, the evenings spent on the phone, the money that leaves each month. Put the weekly figure for each option side by side, because that is the version you will be living in.
What does saying yes to this mean saying no to?
Why ask it
Name the particular thing the same money, years or weekends would otherwise have gone to. 'Other opportunities' is too vague to weigh. 'The down payment' or 'being near my sister while her kids are small' can be weighed.
Can this be undone, and what would undoing it cost?
Why ask it
Few choices are truly one-way, and few are free to reverse. Price the road back: a broken lease, a lost year, an awkward conversation. Where a contract, a loan or a notice period is involved, the exit terms differ from one to the next, so read yours or ask before you count on a way out.
What is the best this could realistically turn out, and how much do I want that?
Why ask it
Describe the good version as plainly as the bad one: what you would have in two years that you do not have now. If the best case leaves you only mildly pleased, the risks under it are buying very little. If it is something you have wanted for a long time, say so, because that belongs on the scale too.
What is the worst outcome that could realistically happen, and what would I do the month after?
Why ask it
Keep it realistic: the outcome a level-headed friend would call possible, not the middle-of-the-night version. Then write the first three things you would do about it. A worst case you can describe recovering from is a risk. One you cannot is a reason to change the size or the timing of the bet.
What is the most likely outcome of each option, not the best or the worst?
Why ask it
It is easy to hold the best case of one choice against the worst case of the other. Describe a plain Tuesday a year into each: where you wake up, who you talk to, what you are worried about. The comparison usually gets closer and more honest.
Does this still work if it takes twice as long or costs a good deal more than I expect?
Why ask it
Plans get made on the smooth version. Rerun yours with a slow start, an extra expense and a few bad months, and see whether it bends or breaks. If it only works when everything goes right, look for a cushion before you look for courage.
Who else pays for this, and have I asked them what it costs them?
Why ask it
Their cost is theirs to state, whether it is a partner changing jobs, children changing schools, a parent seeing you less or colleagues picking up the work. Guessing it for them tends to run low when you want the thing and high when you are looking for a reason not to.
Am I leaning this way because of what I have already put in?
Why ask it
That spending is gone under every option, whether it is years in a relationship, tuition already paid or a deposit you would lose, so it cannot be the tiebreaker. The test is whether you would pick this today if you were starting from zero.
Other people
Whose advice am I leaning on, and what do they stand to gain or lose from my answer?
Why ask it
A parent who would miss you, a friend who made the same choice and needs it to have been right, a recruiter paid when you accept. Having a stake does not make someone wrong. It tells you how much salt to add.
Have I talked to someone who has done this, including someone it went badly for?
Why ask it
People considering a big move mostly hear from those who are glad they made it. Find one person on each side and ask both the same thing: what an ordinary week looks like now, and what they would check first if they were deciding again.
Am I asking for advice, or collecting votes for what I have already chosen?
Why ask it
Look at who you have not asked. If you have been steering around the one person likely to disagree, you know what they would say, and you suspect it has something in it. Ask them, then decide what to do with it.
What would I tell a close friend who brought me this exact problem?
Why ask it
Say the advice out loud, in the words you would use with them. It usually comes quickly, and it is usually kinder and clearer than what you have been telling yourself. Then ask what makes your own case the exception.
What would the person who knows me best say I always do in situations like this?
Why ask it
Ask them outright; they will have an answer ready: you play it safe, you bolt, you wait until the choice is made for you, you say yes and resent it. Then check whether this decision is the pattern again or one of the times it does not apply.
Who will be disappointed whichever way I go, and can I live with that?
Why ask it
Some back and forth is a search for the option that upsets nobody. When there is no such option, the decision becomes which disappointment you can stand behind, and that is easier to face once you have said it in those words.
Has anyone pushed me to answer faster than I wanted to?
Why ask it
Pressure to answer today, before you have slept on it or shown anyone else, is worth noticing whoever it comes from. Ask for the days you need and watch the reaction. If asking for time makes the offer vanish, you have learned something about the offer.
Looking ahead
A year from now, which choice will I be glad I made?
Why ask it
Picture the date on a calendar and yourself looking back at today. Ask it twice, once assuming the choice went well and once assuming it went badly. The option you could defend to yourself in both versions is usually the stronger one.
Which would I regret more: trying this and having it go wrong, or never finding out?
Why ask it
Do not assume the bold answer wins. Never finding out is a real regret, and so is spending savings you needed or hurting someone you love. Say both regrets in full sentences and see which one you flinch at.
If this went badly within a year, what would the most likely reason be?
Why ask it
Your first answer is often a risk you already half know about: the money runs short, the two of you want different things, the role is not what was described. Having named it, ask what you could do this month to make it less likely.
How will I tell, six months in, whether this was a good call?
Why ask it
Write two or three signs now, while you are calm: what you would expect to see if it is working and what would worry you. Put a date in the calendar to read them. Without that, a hard first month and a real mistake look exactly alike.
What would change my mind?
Why ask it
Try to name it exactly: a number, a sentence from a particular person, a result from a trial. If you can, getting that answer is your next job. If nothing on earth would shift you, the deciding is over and what remains is saying so.
Once I have chosen, what is the first thing I do, and on which day?
Why ask it
A decision with no action attached is still a preference. Make the step concrete: sign, call, give notice, book the viewing, tell the person. If the day comes and goes twice, go back to the questions about what you want, because something there is unanswered.
What will I do when the doubt comes back after I have committed?
Why ask it
It will, usually on a bad day. Decide your response now: reread the reasons you wrote down and ask whether any fact has changed. A new fact reopens the question. A bad day does not.
How to work through these when you are stuck
Practical guidance for the conversation itself
Before you answer anything
Answer on paper
A decision turned over in your head comes back around in the same order every time. Written answers stay where you put them, and you can see that the list of reasons for staying has had the same three lines since March. A notes app is fine. Thinking harder is not a substitute.
Take The choice first
The first group looks like the dull one. Do it anyway: a question that is really three questions, or a deadline nobody actually set, cannot be weighed its way out of. Get the one-sentence version and the date before you touch the rest.
Size the effort to the stakes
For something small and easy to reverse, the one-sentence question, the coin, the weekly cost and the first step are enough. Anything that changes where you live, who you live with or how you earn deserves the whole list, over two sittings a few days apart. Compare the two sets of answers: the ones that changed are where the uncertainty lives.
Set a decide-by date before you begin
Choose it now and write it at the top of the page. If someone else has set a deadline, put yours a day or two ahead of theirs so the last hours are not spent in a panic. A date you chose calmly is easier to keep than one that simply arrives.
Reading back what you wrote
Mark the answers that surprised you
Most of what you write will be things you already knew. The two or three lines that made you stop, such as the side of the coin you hoped for or the name that came up when you asked whose 'should' it was, carry more weight than the rest of the page together.
Find the question you skipped
There is usually one you left blank or answered in four words. Go back to it. Often it is the question about who else pays or about what you would choose in private, and the reluctance is the reason it matters.
Sort facts from forecasts
Put a mark beside every answer that is a guess about the future: how you will feel, how someone will react, what the market will do. Then see how much of your case rests on those. Any forecast that one conversation could turn into a fact should be turned into one before the decide-by date.
When the reasons and the feeling point different ways
Do not overrule either one straight away. Ask the feeling what it knows that the list left out, and ask the list what the feeling is ignoring. A strong pull toward an option that fails on cost calls for a cheaper version of that option. A sound-looking option you dread calls for a second pass through What I want.
If the answer still will not settle
The options are close
When two choices score almost the same after all this, the price of picking the slightly worse one is small. Take the one that is easier to reverse, or the one the coin made you hope for, and stop. More analysis of a near tie buys very little.
You are waiting to feel certain
Large decisions rarely arrive with certainty attached, for anyone. Aim for a choice you can explain in two sentences and whose worst realistic case you have a plan for. That standard can be met. Feeling completely sure often cannot.
The same worry keeps returning
Write the worry as a question and work out who or what could answer it. If something can, go and ask. If nothing can, because it depends on a future nobody can see, say that out loud and let the decision be made with the worry still in the room.
It is bigger than a list
Decisions that turn on a contract, a loan, an immigration status, a medical choice or a custody arrangement depend on rules that differ by place and provider, so ask someone qualified how it works where you are. And if a decision is tangled up with feeling unsafe or unable to cope, bring in a person you trust or a professional before you go any further alone.
Once you have chosen
Write down why
Three or four lines, dated: what you chose, what you knew, what you were unsure of and what tipped it. This is the note you reread when doubt turns up, and it stops a later version of you from remembering the decision as careless.
Tell the people it lands on first
Anyone who appeared in your answers under Other people should hear it from you, early and directly, before they hear it sideways. Give them the decision and the reason in plain words. You are informing them at this stage, so do not reopen the vote unless they bring a fact you did not have.
Judge the decision apart from the result
A careful choice can turn out badly and a careless one can get lucky. When you look back, ask whether you used what you knew and checked what you could. That is the part you can do better next time, and it is the only fair thing to grade yourself on.
Keep the review date
On the day you set for the six-month check, read the signs you wrote in advance and answer them plainly. If the worrying ones have come true, you now have a new decision, and this list works for that one as well.