Questions to Ask About the Future
Questions to ask about the future, whether it is a partner's, a friend's, a parent's or your own. They start with hopes and plans, move through work, money, home and family, and reach fears, getting older and the world ahead once the easy ground is covered. The home and family group ends with the ones to ask when planning your future with a partner. The last group is written to put to yourself when deciding a future, whether that is a course, a job or a city, though most of it works on someone else too.
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The questions
Each question, and why to ask it
Hopes and plans
What do you think your life will actually look like in five years?
Why ask it
The usual five-year question gets the hoped-for version. 'Actually' asks for a forecast, and the distance between the two is the interesting part. If the prediction is bleaker than the hope, come back to that later.
What are you most looking forward to in the next few years?
Why ask it
Anticipation is pleasant to describe and needs no plan behind it, which makes this the gentlest way into the subject. If all that comes to mind is a vacation, the bigger things may feel stuck, and that is worth asking about once the conversation has warmed up.
What do you most want to be different a year from now?
Why ask it
A year is close enough that people answer concretely: a job, a living situation, a habit, a person. Longer horizons tend to bring out the polished answer saved for job interviews.
What is the biggest goal you have set yourself?
Why ask it
Some people answer in one breath and others find they have several small goals and no big one. Both are worth hearing. If a goal is named, ask how they will know it is done: 'get fit' and 'run the half marathon in May' are not the same kind of goal.
What dream have you not given up on?
Why ask it
The wording admits that some dreams have been given up, which makes this easier to answer honestly. Ask what would have to be true for it to happen, and you find out whether it is a plan or a comfort.
What are you working toward at the moment that nobody really asks you about?
Why ask it
Evening classes, a savings target, a manuscript in a drawer: plenty of plans go for years without an audience. This may be the first time it has been said out loud, so hold back any opinion on how realistic it is.
Are you more of a planner, or do you decide things late?
Why ask it
Low stakes, and it explains a lot of friction between two people making a decision together. It also changes how to read their other answers about the future, since someone who decides late may truly have no five-year picture to give you.
What is at the top of your bucket list?
Why ask it
Get the top item, then one that would surprise the people who know them. What would it take to do the first within two years? A list with no dates on it tends to stay a list.
Where do you most want to travel that you have not been yet?
Why ask it
The place matters less than where the idea came from. A grandparent's stories, a film seen at fourteen or a friend who moved there each make for a different trip. It is also a good one to reach for when a heavier question has just landed.
If money stopped being a reason, what would you spend your days doing?
Why ask it
The lottery version of this gets a beach and a big house. Asking about days gets the activity itself, and a small version of it is often within reach already: teaching one evening a week, a bench in the garage, a semester of classes.
Describe your ideal day ten years from now, from waking up to going to bed.
Why ask it
Walking through a whole day forces details that a goal never does: when the alarm goes off, who is at breakfast, whether there is a commute. Notice what is missing from the day, a job, a city, a person, and ask about that.
What do you want to be good at in ten years that you are a beginner at today?
Why ask it
A language, an instrument, running a business, cooking for twelve. Ten years is a long runway for any of them, which makes this one of the few wishes about the future that comes with an obvious route. When is the first lesson?
Work and money
What kind of work do you want to be doing a decade from now?
Why ask it
Leave it open and see what they reach for: a title, a kind of day, a set of people, or not working at all. Someone who answers with hours and freedom instead of a role has told you what their next job decision will turn on.
Is there a different career you still think about trying?
Why ask it
It tends to come out with a laugh, as if it were a joke. Ask what the first real step would be and what it would cost. A course fee or a pay cut turns a daydream into a decision that can be made either way.
Would you ever want to work for yourself?
Why ask it
A quick yes or no with a long story behind it. A yes generally comes with a particular business in mind, so find out what it is. A no often traces back to someone else's experience: a parent's shop, a friend's bad year.
What does success mean to you now, compared with ten years ago?
Why ask it
The comparison is the useful half. Definitions often move from being seen to do well toward time, health and who is around, and knowing where someone is on that road explains choices that look odd from outside, such as turning down a promotion.
How much money would be enough for you?
Why ask it
The answer can be a figure or a life, such as a paid-off home and no boss. A target that has never been named has a habit of moving every time it gets close. Keep your own view of the number to yourself, since what counts as enough depends on where they live and who relies on them.
What are you saving for, if anything?
Why ask it
A plain question about what the nearer future is being built toward: a down payment, a trip, a cushion, a child's education. 'Nothing in particular' is common and no failing. With a partner it is worth knowing whether that is a choice or because nothing is left over at the end of the month.
Would you rather have more money or more free time in the years ahead?
Why ask it
Time is the easy thing to say, until the free week they describe turns out to cost money. Neither answer is wrong. The trade comes up at every raise and every promotion, so it helps to know in advance which way someone leans.
When would you like to stop working, and what would you do with the first year?
Why ask it
Retirement ages and pension rules differ by country and employer, so stay with the picture and leave the arithmetic for another day. The first year is the telling part. Some people have it planned to the week, and others find they have only ever imagined the farewell party.
Home and family
Where would you most like to end up living?
Why ask it
Listen for whether the answer is a place, a kind of place, or near a person. 'Close to my sister' and 'somewhere with a garden' are different sorts of plan, and the second can be met in a hundred towns.
Is there somewhere you have always wanted to live for a year, just to try it?
Why ask it
A year is short enough to say out loud without sounding as though you are leaving everyone behind. What has stopped them so far? A school year, a lease and a job are real obstacles, and all three have end dates.
Is owning a home something you are aiming for?
Why ask it
Some people have wanted this since childhood, and some see a house as an anchor they would sooner not drop. Ask what owning would give them that renting does not: security, a garden, the right to knock down a wall. What is realistic depends on prices where they live, so keep to the wish and leave the sums alone.
Is marriage part of the future you picture?
Why ask it
From a friend this is simple curiosity. From a partner it weighs far more, so be clear which you mean before you ask. A long pause is not a no: plenty of people have never been asked directly and are working it out as they speak.
Do you picture children in your life, your own or other people's?
Why ask it
Adding other people's children makes room for anyone who will not be a parent, by choice or otherwise, and still intends to be an aunt, a godparent, a coach or a teacher. Never answer a no with 'you might change your mind'. Ask what they want that part of life to hold instead.
What do you hope we are still doing together years from now?
Why ask it
This works with a partner, a sibling or an old friend, and it tends to get a small, specific answer: the Sunday walk, the yearly trip, arguing about the same film. Whatever they name is the part of the relationship they would miss first.
Which friendships do you most want to still have in twenty years?
Why ask it
Getting two or three names is the point. Long friendships often run on one person who keeps making the call, so ask who does the calling at the moment and whether that could be shared.
How do you expect things to change with your parents as they get older?
Why ask it
For a lot of people this is the largest part of the future they did not choose. Who lives nearest, who has the spare room and who has already been asked are usually known and seldom said. Go gently if a parent is unwell, and let a short answer stay short.
What do you hope the next generation keeps from you, and what do you hope they drop?
Why ask it
The second half is where this gets honest. A temper, a way with money, a habit of leaving things unsaid: most people can name something they inherited and would sooner not hand on. Naming it is enough, so do not press for how they plan to fix it.
Which family tradition do you want to outlast you?
Why ask it
A small question with a long reach. The tradition named, a meal, a trip, a way of marking birthdays, often rests on one person doing the work. Who is that now, and who would pick it up?
If one of us were offered a job in another city, how would we decide?
Why ask it
Far easier to talk through as a hypothetical than in the week an offer arrives. Listen for the rule each of you assumes: whoever earns more, whoever moved last time, whoever wants it most. Two people can carry different rules for years without finding out.
How close do we want to live to each of our families?
Why ask it
Distance settles a good deal else: who helps with children, who hosts the holidays, who is nearby when a parent needs care. 'Close' can mean ten minutes to one of you and a two-hour drive to the other, so put a number on it.
If we could afford only one of the big things in the next five years, which would you pick?
Why ask it
A house, a wedding, a child, a year abroad and a change of career will not all fit into the same five years for most couples. Choosing one brings out the order each of you has been carrying around. Stay with the ranking, because how to pay for any of it is a separate conversation.
What timeline do you have in your head that you have not said out loud?
Why ask it
Engaged by thirty, a child before thirty-five, out of this apartment by spring. A private deadline turns into quiet resentment when the other person does not know it exists. Hearing one is not agreeing to it, but it does mean nobody is running late by a clock they cannot see.
Which of our plans have we both assumed and never actually agreed?
Why ask it
Where the holidays are spent, whether the spare room becomes an office, who cuts back at work if a baby comes. An assumption feels like an agreement until the day it is tested. Name one each and leave the arguing for another evening.
What part of your future do you want to stay yours, whatever we plan together?
Why ask it
A shared plan can swallow the things only one of you wanted: the degree, the band, the months spent near a grandparent. Asked early, those get built in. Asked late, the same wish tends to arrive as a complaint.
Fears and aging
What scares you most about the years ahead?
Why ask it
Expect money, health, or someone else's health sooner than anything abstract. Resist the urge to reassure. Agreeing that it is a reasonable thing to worry about keeps people talking, where comfort usually ends the subject.
How do you cope with not knowing how things will turn out?
Why ask it
Some people plan harder, some lean on faith, some stay busy and some simply do not look. None of these is wrong. It is a fair guide to how someone is likely to react when a plan falls through, which is useful to know before it happens.
Do you think the future is mostly decided for us, or mostly made by what we do?
Why ask it
This sounds like philosophy and turns out to be practical. A person who thinks life is mostly luck plans differently from one who thinks it is mostly effort, and two people who differ on it can argue about saving, risk and blame for years without seeing why.
If you could know one thing about your future, what would you pick?
Why ask it
The choice points at whatever is most uncertain for them right now: whether a relationship lasts, whether the money holds out, how their health goes. Some people would rather know nothing at all, and their reason is an answer too.
What is your plan B if the main plan does not work out?
Why ask it
Having a fallback is not pessimism, and for some people it is what makes the first risk possible at all. If there is none, ask what would be first to go if things got tight. That answer is a plan B in miniature.
How do you feel about getting older?
Why ask it
Answers split between people who dread it and people who are relieved by it, and both usually have a specific reason: a parent's decline, a body that already hurts, or relief that the pressure they felt at twenty-five has gone.
Would you want to live to a hundred?
Why ask it
Hardly anyone gives a plain yes. The conditions people attach, a working mind, a partner still alive, enough money, not being a burden, add up to a list of what they fear about old age, reached without asking about fear at all.
Which older person do you know whose life you would be glad to have?
Why ask it
A real example beats a description. Ask what that person was doing in the middle of their life that led there, because the answer is rarely dramatic: they stayed in touch with people, kept moving, held on to some work they liked.
What do you hope is still true of you at eighty?
Why ask it
Curiosity, a sense of humor, getting up a hill unaided, being the one the grandchildren call. Whatever is named is something they value in themselves already, so the natural follow-up is which of those is getting the least care this year.
What would you do differently if you knew you had five years left?
Why ask it
A short horizon takes away the long-term reasoning and shows what is being put off. The honest reason it has not started is more often money or fear than time. Skip this one with anyone who is ill or has lost someone recently.
What do you want the people who know you to remember about you?
Why ask it
A plainer way of asking about legacy, a word that invites grand answers nobody means. Listen for whether they name something they did or a way they treated people, and whether an ordinary week of theirs has much of it in it.
The world
Are you more hopeful or more worried about the future than you were five years ago?
Why ask it
Comparing with five years ago gets a direction of travel instead of a temperament. Ask what moved it. Often it is not the news at all but one event close to home: a birth, a layoff, an illness in the family.
Do you expect your life to be easier or harder than your parents' was?
Why ask it
This reaches money, class and generational worry without using any of those words. Because the comparison is with two real people, the reasons come out concrete: the price of a house, how secure work was, how much help they had.
What do you think will have changed most about everyday life in twenty years?
Why ask it
After the personal questions it is a relief to look outward for a while. Listen for whether the picture is one they are resigned to or one they think is still open to change.
Which change in technology are you looking forward to, and which one worries you?
Why ask it
One of each stops the answer turning into a speech in either direction. The worry tends to sit close to the person's own job or their children, which brings a very large subject back to something they have a stake in.
What do you think this town will be like in thirty years?
Why ask it
Nearer than the planet and easier to picture: the main street, the price of a house, the weather, who can afford to stay. People are specific about a place they know well, and the answer often gives away whether they expect to be living there to see it.
What will children today find strange about how we live now?
Why ask it
A lighter way to talk about change, and usually a funny one. Driving ourselves around, carrying cash and typing on glass all come up. Under the joke is a real opinion about which of today's habits deserve to go.
What problem do you most hope gets solved in your lifetime?
Why ask it
The answer is often personal underneath: an illness that runs in the family, the cost of housing where their children live, something they see every day at work. Ask what first made it matter to them, and keep off party politics unless you both want to go there.
What gives you hope, and what is that based on?
Why ask it
Asking for the basis keeps this from becoming a pleasant platitude. Hope that rests on particular people, or on progress they have seen for themselves, stands up to a second question. If nothing is behind it they will usually say so, and that is a fair answer too.
Ask yourself
What are you doing now that you think you'll be glad about in twenty years?
Why ask it
This turns from wishes to current behavior, which is harder. Putting a little money aside, staying in touch with one friend and keeping fit are the usual candidates. If nothing comes to mind, stay with the blank for a minute before reaching for an easy answer.
What are you doing now that your future self will have to pay for?
Why ask it
Less comfortable than listing what you are getting right. Sleep, debt, a neglected friendship and a postponed check-up are the usual answers. Pick one to do something about, not the whole list, and never supply the answer for someone else.
What would your future self tell you to stop worrying about?
Why ask it
It is easier to start by looking back. What were you anxious about ten years ago that came to nothing? The same pattern probably holds today. That does not make the worry vanish, but it does put a size on it.
What would you write in a letter to yourself, to be opened in ten years?
Why ask it
Worth doing for real, on paper, sealed and dated. Notice which kind of sentence comes first: something you hope is still true, or something you hope is over by then. The second kind shows what is weighing on you this year.
Which of your goals are really yours, and which did you pick up from someone else?
Why ask it
Parents, teachers, a group of friends or a whole industry can hand over a goal that then gets chased for years. One test is whether you would still want it if nobody ever found out you had done it. Worth asking in the last years of school and the first years of work especially.
What would you try if you were not afraid of looking foolish?
Why ask it
The better-known version asks what you would do if you could not fail, but failing is seldom the real brake. Being seen to fail is. Working out whose face you picture when you imagine it going wrong can take some of the weight off.
What do you think you'd regret not doing?
Why ask it
A regret that has not happened yet can still be avoided, which makes this more use than raking over old ones. Notice whether the answer is something to achieve or someone to spend time with, because the two call for very different next steps.
Which decision are you putting off because either answer changes a lot?
Why ask it
Whether to move, whether to stay in a job, whether to have a hard conversation with a relative: there is generally one waiting. Naming it is enough for today. If you put this to someone else, you are asking for the name and not the verdict.
If you flipped a coin between your options, which side would you hope for while it was in the air?
Why ask it
The coin decides nothing. Its use is the second before it lands, when a preference you already had makes itself felt. Feeling nothing either way is information too: the options may be closer in value than the agonizing suggests.
Which of your options could you undo in a year if it turned out to be wrong?
Why ask it
A course can be changed, a lease runs out and most jobs can be left, while a few choices cannot be taken back at all. Sorting them this way shows which decisions have earned a long deliberation and which can simply be tried.
Who is already living the future you are considering, and what is an ordinary Tuesday like for them?
Why ask it
A career or a city looks different from inside a normal week than it does in a prospectus. Ask one of them for twenty minutes, and ask what they would warn a newcomer about. The dull details, the commute, the paperwork, the hours, are the ones that decide whether you would like it.
What do you need to find out before you can decide, and who could tell you?
Why ask it
A stuck decision is often just missing a fact: what the course costs, whether the visa allows work, what the job pays after two years. List the unknowns and put a name or an office beside each. Fees, visas and funding differ by country and school, so ask how it works where you are headed.
What would you have to give up to get what you say you want?
Why ask it
Every plan has a price that goes unmentioned: evenings, a salary, a city, a version of yourself that other people like. A plan that has been priced and is still wanted can be believed. One that has never been priced is still a wish.
What is one small thing you could do this month toward the future you want?
Why ask it
Small enough to be real: a phone call, an appointment, an application form, a conversation that has been avoided. If you asked someone else, offer to check in on it later and then do. The check-in is what makes the question count.
Having this conversation well
Practical guidance for the conversation itself
When these questions work
One group at a time
The list is long on purpose, and nobody should hear all of it in one sitting. Choose the group that fits the day, work and money on a long drive, home and family over a slow meal, and take five or six questions from it. The first five under hopes and plans are safe openers with almost anyone.
Long stretches, no audience
Car journeys, walks and late evenings suit this list because nobody has to hold eye contact and there is time for a slow answer. A dinner party is the wrong room for it: with a table listening, answers about the future get performed instead of thought about.
Not while a decision is pending
If the two of you are mid-argument about moving, marrying, or changing jobs, these questions get recruited into the argument. Have that conversation directly and save these for a week when nothing is being decided.
Planning your future with a partner
The closing run of home and family is written for two people: the job in another city, how near to live to each family, which big thing comes first, the timeline nobody has said aloud. Take it on a quiet weekend, both answer every question, and write down what you agreed and what you did not. A difference found now costs an evening, and the same one found after the lease is signed costs a good deal more.
Trade answers
Questions about regret, aging and what someone wants to be remembered for are unfair to ask one way. Answer each one yourself, at similar length, or it becomes an assessment.
With a teenager or a student
Leave out retirement and aging and stay with the next year, what they want to be good at, and whose goals they are chasing. 'I don't know yet' is an honest answer at seventeen. Treat it as one and the conversation stays open for next time.
What to listen for
- The gap between what someone expects and what they hope for. That distance is often the most useful thing they will tell you.
- Whether the future they describe has other people in it. Plans described entirely in the first person sometimes mean a relationship is not being counted on.
- Deferral language: after the kids, once work settles, when things calm down. Ask what specifically would have to happen, since often nothing ever will.
- Silence after a question rather than a quick answer. The considered answers are worth the wait, and filling the pause loses them.
Questions to ask yourself when planning your future
Write the answers down
The last group is written to work without a second person. Answer on paper, in full sentences, with the date at the top. A thought that stays in your head gets revised without your noticing, and a written one cannot be. The letter to yourself is the same idea with an envelope.
Read them again in a year
Keep the page and come back to it at the same point next year. What changed, what did not, and what you had forgotten you wanted are more use than a fresh set of resolutions.
When a choice is still open
Some of this group is for the weeks when you are deciding between futures: which course, which offer, whether to go or stay. Start with the coin, which is quick and shows which way you lean, then ask what could be undone, then take the two that send you off to find something out. Answer them again a week later and see whether anything moved.
Then tell one person
A plan that somebody else has heard is harder to drop quietly. Pick someone who will ask how it is going without nagging, and offer to do the same for them.
What to avoid
Reassuring away a fear
Telling someone their worry is unlikely ends the subject without addressing it. Ask what they have already thought about doing, which treats the fear as reasonable and often turns it into something practical.
Judging their timeline
Someone with no five-year plan is not necessarily adrift, and someone with a detailed one is not necessarily secure. Ask how their approach has served them rather than suggesting a different one.
Turning it into advice
The moment you start proposing solutions, honest answers stop. If you have suggestions, ask at the end whether they want them, and accept no.
Pushing optimism
Insisting on hope from someone in a hard stretch reads as being told their situation is not real. Sitting with the bleak answer is usually what earns the more hopeful one later.
Pressing on marriage and children
These two questions weigh more than the rest, and the same words land differently from a friend, a parent and a partner. Ask once and take the answer you are given. Arguing with a no, or putting a deadline on a maybe, closes the subject for a long time.