101 Questions to Ask in Your 20s
One hundred and one questions for a decade when most things are still open, covering whose plan you are following, the first years of work, what your money is actually doing, friendships that need effort to survive, dating, becoming separate from your family, health you are borrowing against, and what you want to be true at thirty five.
The questions
Open any question for the note
Whose plan am I currently following?
Why ask it
A great many twenty-somethings are executing a plan set by a parent, a school or a degree choice made at seventeen. Naming the author is the first step to deciding whether to keep it.
What would I be doing if I had never told anyone what I was going to do?
Why ask it
Public declarations create obligations that outlast the interest behind them. The answer is often something you have quietly wanted for two years.
What am I doing because I am afraid of falling behind?
Why ask it
Behind whom, exactly, and on whose timetable. Making the comparison explicit usually shows it is against three specific people you follow online.
What did seventeen year old me get right about what I wanted?
Why ask it
Early instincts about people and subjects are often better than the ones you adopted later to sound sensible. Look for anything you enjoyed before you knew whether it was impressive.
What am I still doing only because I started it?
Why ask it
A degree, a city, a relationship or a job can continue on momentum long after the reason expired. Sunk cost is a much stronger force at this age than anyone admits.
What would I need to see in a year to know this was the right direction?
Why ask it
Naming the evidence in advance is how you avoid either quitting in a bad month or staying for five years. Write the sentence down where you will find it.
What do I already know that I am pretending to be undecided about?
Why ask it
Some decisions are made and only need announcing, and the delay is about other people's reaction. Notice the discomfort at this question rather than the answer.
What is the most interesting thing that happened to me this year?
Why ask it
If the answer is nothing, your twenties are quietly turning into a holding pattern. Interesting is not the same as good, so accept a difficult answer.
Where do I actually want to be living, as opposed to where I have ended up?
Why ask it
Cities get chosen by a first job or a university and then keep you for a decade. If the honest answer is somewhere else, work out what is genuinely holding you.
What do I want that I would be embarrassed to say to my friends?
Why ask it
Money, a conventional life, children young, leaving the city, becoming religious, becoming famous. Peer group shapes stated ambition more than anyone likes to think.
Who am I trying to impress, and do they know I exist?
Why ask it
It is frequently a former teacher, an ex, a parent or a stranger online. Once named, the effort often loses its grip.
What would change if I assumed nobody was watching my twenties?
Why ask it
This decade gets performed more than any other. Ask which of your choices are for the record rather than the life.
What is the actual job of the person two levels above me?
Why ask it
Most people aim at a title without knowing what the work consists of, and it is often nothing like their current role. Ask one of them to describe last Tuesday.
Would I want my manager's life?
Why ask it
Their hours, travel and stress are your likely future if you stay on this path. If the answer is no, the question is where you get off, not whether you work harder.
What am I learning here that transfers, and what only counts inside this company?
Why ask it
Internal systems, jargon and relationships evaporate when you leave. The transferable list is what you are actually building.
What could I do in six months that would make me hard to replace?
Why ask it
Specific and slightly unglamorous answers are the good ones: the thing nobody else understands, the process nobody else will own. Vague answers mean you have not looked.
Who at work would take my call in three years?
Why ask it
Careers move on relationships more than performance, and this is the age at which they are cheapest to build. If the list is short, that is the project for this year.
What feedback have I been given twice?
Why ask it
Repetition from unrelated people is usually accurate even when badly delivered. Write down the version you find hardest to argue with.
Am I underpaid, and how would I find out?
Why ask it
Salary bands, recruiters and honest peers all exist. Not knowing is the single most expensive habit of a first decade at work.
When did I last ask for something at work?
Why ask it
A raise, a project, a title, a course, a day off. People who never ask are usually surprised by how often the answer is yes.
What would I do if my whole industry shrank?
Why ask it
It is a useful exercise rather than a prophecy, and it tells you how narrow your skills currently are. A blank answer is a to-do list, not a catastrophe.
Is this job a step towards something, or just a job?
Why ask it
Both are acceptable and the mistake is confusing them, then feeling guilty about a job that was only ever paying rent. Name which one it is.
What is the longest I am willing to stay somewhere I have stopped learning?
Why ask it
Setting the limit in months, in advance, is what prevents three years disappearing. Put the date in your calendar.
What kind of work makes the time disappear?
Why ask it
Absorption is a better career signal than enjoyment because it is repeatable. Note the activity, not the job title it came inside.
What am I bad at that will eventually matter?
Why ask it
Writing clearly, speaking to a room, negotiating, saying no, managing people. In your twenties these are cheap to learn and later they are expensive.
Would I rather be paid more or work less, right now?
Why ask it
Answering honestly at twenty five saves a decade of optimising the wrong thing. The answer is allowed to change, but it should be a choice.
What work would I do for free, and what does that tell me?
Why ask it
It usually points at an audience or a craft rather than a career. Treat it as information about direction rather than a plan to work unpaid.
Who do I know that I have never asked how they got their job?
Why ask it
People explain their path readily and the real sequence is always messier than the public version. One coffee a month is a career strategy.
What did I spend last month, by category, without guessing?
Why ask it
The exercise is dull and it is the highest-return hour available to most twenty-somethings. Almost everyone finds one category two or three times larger than they assumed.
What is my rent as a share of what I take home?
Why ask it
It is the single number that decides how much freedom you have, and it can be changed. Anything over a third makes every other financial decision harder.
What do I owe, at what rate, and what is the payoff order?
Why ask it
Rates differ enormously between student loans, cards and car finance, and the order matters more than the effort. Write the list once and follow it.
How many months could I cover with no income?
Why ask it
This number is what converts a bad job into a job you can leave. Three months buys more freedom at this age than almost any purchase.
What would I do if I lost my job next month?
Why ask it
The plan is usually short: cut these costs, ask these people, apply to these places. Having written it down removes a background hum of dread.
What am I paying for monthly that I have forgotten about?
Why ask it
Subscriptions, storage, apps, an old gym, insurance for something you sold. Twenty minutes of checking usually recovers real money.
What did I buy this year that I still think was worth it?
Why ask it
The pattern in your good purchases is more useful than a budget, and it is often cheap and boring. Spend more on whatever appears here.
What am I spending to look like someone I am not yet?
Why ask it
Clothes, rounds of drinks, holidays and a postcode all show up here. Naming it is not an argument for austerity, just for choosing deliberately.
Have I started saving anything for a pension, and do I know what happens if I do not?
Why ask it
Money put in during your twenties has decades to compound, which is an advantage you cannot buy back later. Find out what your employer will match and take all of it.
What money conversation with my family have I been avoiding?
Why ask it
Support being given or expected, a loan, an inheritance assumption, who pays at dinner. Vagueness here causes years of resentment in both directions.
Do I know what I am worth to another employer?
Why ask it
Interviewing occasionally, even without intent to move, is how you find out. People who never test the market are paid what they were worth three years ago.
What would I do with an extra five hundred a month?
Why ask it
The answer shows whether your instinct is safety, freedom or status. It is also a useful target once you know where your money is currently going.
What am I saving for, specifically?
Why ask it
Saving without a purpose becomes anxiety and spending without one becomes leakage. A named goal with a rough figure survives a bad month much better.
What did I learn about money by watching my parents?
Why ask it
Secrecy, generosity, panic and refusal to look are all inherited before they are chosen. Naming the inheritance is what lets you keep the good parts.
Which of my friendships are only surviving on shared history?
Why ask it
Some are worth maintaining anyway and some have quietly ended. Being honest about which is which frees up real time.
Who do I see because I want to, and who because it is arranged?
Why ask it
University and work friendships run on proximity and dissolve the moment it stops. This is the decade in which that becomes visible.
Which friend have I not seen since we both got busy?
Why ask it
The friendships that fade in your twenties usually fade by accident rather than decision. One message is often enough to restart it.
Who is going to be at my fortieth?
Why ask it
It is a blunt way of asking which friendships you are prepared to maintain deliberately. Most of the people on that list need some effort in the next two years.
Am I the one who organises things, or the one who gets invited?
Why ask it
Both roles are fine and only one of them keeps a group together. If nobody in your circle organises, the group has a few years left.
Who do I call when something goes badly?
Why ask it
If the same name comes up every time, that person is carrying a lot. If no name comes up, that is the more urgent finding.
Which of my friends would tell me I was making a mistake?
Why ask it
A circle that only encourages is pleasant and not much use. Name the one person who would say it and ask them things more often.
What kind of friend am I when I am busy?
Why ask it
Most people go quiet and their friends read it as cooling. Deciding on one thing you keep doing regardless protects the friendships you want to keep.
Am I still making new friends, or only maintaining old ones?
Why ask it
The mechanisms that supplied friends automatically stop working after university. If you cannot name someone new from the last year, that needs deliberate effort.
What do I contribute to my group of friends?
Why ask it
It might be organising, listening, humour, or a spare room. Knowing it makes you less anxious about your place in it.
How much of my social life happens on a screen?
Why ask it
Messaging maintains friendships and does not build them, and it is easy to mistake one for the other. Count the hours spent in the same room as someone this month.
Who do I envy, and what specifically do I envy about them?
Why ask it
The specific object of envy is a clear signal about what you want, and it is usually narrower than the whole life. Take the signal and drop the resentment.
What am I actually looking for right now?
Why ask it
Company, sex, a life partner, a distraction and something to tell people are all different, and being unclear wastes other people's time as well as yours. It is allowed to change, but say it to yourself first.
What did I learn about relationships from watching my parents?
Why ask it
The lesson is in what they did rather than what they said about it. This is the age at which you can still choose which parts to keep.
What did my last relationship teach me about myself, not about them?
Why ask it
The version of the story where the other person was simply wrong teaches nothing. Look for your own repeated behaviour instead.
What pattern do I keep repeating in who I choose?
Why ask it
There nearly always is one, and friends can usually name it faster than you can. Ask one of them.
What would I not compromise on in a partner?
Why ask it
Two or three items, specific, is a useful list. Twenty items is a way of avoiding the question.
Am I in this relationship, or in the habit of it?
Why ask it
Long relationships that started at nineteen can continue for years on momentum. Ask whether you would choose it now, from scratch.
What do I need from a partner that I have never asked for out loud?
Why ask it
Unspoken requests get read as moods and cause resentment in both directions. Write the one sentence you would want them to hear.
How do I behave in an argument, honestly?
Why ask it
Shouting, going silent, going cold, over-apologising. Knowing your own pattern is what lets you warn someone instead of surprising them.
Do I want children, and by roughly when?
Why ask it
It affects who you should be dating, how you save and where you live, and it is easier to think about calmly at this age than at thirty five. Uncertain is a legitimate answer to hold deliberately.
What would make me end a relationship?
Why ask it
Knowing your own limits in advance is what stops you discovering them years late. The answers are usually about how you are treated rather than what happens.
Am I ready to be someone's partner, or do I need a year alone?
Why ask it
Some of the most useful years in a twenties are spent single on purpose. Asking the question honestly is more useful than dating out of momentum.
Who am I when I am single?
Why ask it
If the answer is unclear, that is worth knowing before the next relationship rather than after it. It is also the answer that makes you easier to be with.
What do my parents expect of me that I have never disputed?
Why ask it
A career, a religion, proximity, grandchildren or a certain kind of respectability. This is the decade in which those expectations get either accepted or renegotiated.
What do I need to say to a parent while I still can?
Why ask it
Gratitude, a grievance, a question about their own life. People in their forties consistently report wishing they had asked sooner.
What do I not know about my family's history?
Why ask it
Grandparents' stories go undocumented and then unrecoverable, and your twenties is when most of them are still available. Ask one specific question at the next family gathering.
How much do I want my family involved in my daily life?
Why ask it
The answer is allowed to be less than they want, and saying it plainly once is kinder than gradual withdrawal. Say what you will keep rather than only what you are cutting.
Which of my parents' habits am I repeating?
Why ask it
Temper, avoidance, generosity, secrecy about money, working too much. Naming it is most of the work of not passing it on.
What have I forgiven them for, and what am I still holding?
Why ask it
The held item is worth naming even if you never raise it with them. Ask what would count as settling it.
What responsibility for my family will fall to me eventually?
Why ask it
Care for a parent, a sibling who needs help, a family business, a house. Knowing it is coming changes how you plan your thirties.
Am I financially independent, and if not, what would it take?
Why ask it
Support from family is common and unremarkable, and the risk is only in not knowing the terms. Ask what the arrangement actually is and when it ends.
What do I do at family gatherings that I would not do anywhere else?
Why ask it
Old roles reactivate: the difficult one, the peacemaker, the child. Noticing the role is what makes it optional.
What family tradition do I want to keep, and which am I letting go?
Why ask it
The second half is rarely stated and is usually practical rather than a rejection. Deciding now is easier than improvising when you have your own household.
What am I doing now that my forties will bill me for?
Why ask it
Sun, smoking, teeth, alcohol, sleep debt and untreated injuries all compound. This is the cheapest decade to change any of them.
Have I registered with a doctor and a dentist where I actually live?
Why ask it
Vast numbers of people in their twenties have not, and then find out during an emergency. It takes twenty minutes and one form.
What do I use to take the edge off, and how often?
Why ask it
Drink, weed, screens, food and shopping all do the same job on a bad evening. Counting the frequency is more useful than judging it.
How much am I sleeping, and what is actually stopping me?
Why ask it
It is usually the hour before bed rather than the bed. Almost every mood question in this decade sits downstream of this one.
What kind of movement would I still be doing in ten years?
Why ask it
Enjoyment is what makes it repeat and discipline is what makes it stop. If nothing comes to mind, the task is to try several things, not to try harder.
Is there a health thing I have been meaning to get checked?
Why ask it
The deferred appointment is usually the one you are quietly worried about. Booking it is the entire answer.
What does my body do when I am under real stress?
Why ask it
Jaw, stomach, sleep, skin, appetite. Learning your own signals turns them into an early warning system rather than a surprise.
Am I eating like someone who is going to be alive for sixty more years?
Why ask it
The question is about the ordinary weekday pattern rather than the occasional excess. Notice the timing and the tiredness, not just the food.
What have I never learned to do that most adults can?
Why ask it
Cooking five meals, basic finances, changing a tyre, swimming, saying no. Filling one gap a year is a decade well spent.
How much of my day is spent looking at a phone, according to the phone?
Why ask it
Guessing is always wrong and the real figure is usually startling. Compare it with the things you say you have no time for.
What would I learn if there were no exam and no career benefit?
Why ask it
This separates genuine curiosity from credential-collecting, and the answer often points at work you would be good at. Give it two hours a week and see whether it survives.
What skill would be most useful to me in ten years?
Why ask it
Language, code, writing, a trade, statistics, or how to run a meeting. Choose for leverage rather than for interest, and expect the honest answer to be unexciting.
What am I willing to be visibly bad at in front of other people?
Why ask it
Adults avoid the beginner stage more than the effort, which is why new skills stop arriving after university. Naming one thing is the real commitment.
What do I read, and is any of it changing my mind?
Why ask it
Reading only what confirms you is a form of entertainment. Look for one source you disagree with and can still respect.
Who could teach me something if I simply asked?
Why ask it
Older colleagues, relatives and neighbours are generally willing and rarely asked. The specific request works better than a general offer of coffee.
What did I quit that I should probably restart?
Why ask it
An instrument, a language, a sport, a piece of writing. Restarting is faster than starting and most people underestimate how much is retained.
Should I be studying formally, and what would it actually buy me?
Why ask it
Postgraduate study is sometimes the right move and sometimes an expensive way to postpone a decision. Ask three people who did it whether it changed their options.
What do I want to be competent at by thirty?
Why ask it
One or two named things, with a rough standard. It is a far better target than a job title.
What do I want to be true about my life at thirty five?
Why ask it
Two or three specifics rather than a mood, written down and dated. Reading it at thirty is instructive whichever way it turned out.
What would I regret not having tried before I had responsibilities?
Why ask it
Some things, a country, a risky job, a long trip, a bad idea, get very hard once there are children or a mortgage. Pick the one that would sting most and cost it out.
What am I postponing until I feel ready?
Why ask it
Readiness usually arrives after the first attempt rather than before it. Name the smallest possible version and do that instead.
What would I do differently if I knew this decade would go quickly?
Why ask it
It does, and the answer is usually about people rather than achievements. Act on whichever name appears first.
What is the one habit I would most like to have by thirty?
Why ask it
Consistency over years matters more than intensity now. Choose something small enough that a bad month cannot break it.
Who do I want to become, described as behaviour rather than adjectives?
Why ask it
Kind is not actionable and calls his mother on Sundays is. Write three behaviours instead of three traits.
If nothing changed for five years, what would bother me most?
Why ask it
This locates the single thing worth real disruption. Everything absent from the answer probably deserves less worry than it gets.
Using These in Your Twenties
Practical guidance for the conversation itself
How to Get Something Out of This
Answer With Facts Where Facts Exist
Rent as a share of income, last month's spending by category, hours on your phone, months of savings. Half of these questions have a factual answer and a flattering answer, and only the factual one changes anything.
Take One Section, Not the Whole List
The sections cover where you are, work, money, friendship, relationships, family, health, learning and the next ten years. One section and an hour beats an ambitious evening that produces a hundred shallow answers.
Convert Two Answers Into Appointments
A doctor, a dentist, a coffee with someone whose job you want, a pension form, a message to a friend who faded. Reflection that produces nothing in the diary tends not to survive the week.
Ask Someone Who Will Disagree
On patterns in relationships, on how you behave in arguments and on what you are bad at, other people are better witnesses than you are. Pick the friend who will not be diplomatic.
Traps Specific to This Decade
Optimising a Path You Have Not Chosen
It is easy to spend five years getting better at something you never decided to do. Ask whose plan you are following before you ask how to execute it faster.
Mistaking a Timetable for a Life
Comparing yourself against a schedule, promoted by this age, married by that one, mostly measures you against a handful of people you follow online. Name them and the comparison usually loses its power.
Waiting to Feel Ready
Confidence generally follows the first attempt rather than preceding it. If a question here produces some day, find the smallest version that could happen this month.
Treating Every Answer as a Commitment
These are meant to be revisited, not signed. Answers given at twenty three should look wrong at twenty nine, and that is the point of dating them.
Making It Worth Repeating
- Date every set of answers and keep them all in one place, because the comparison is where the value is.
- Pick five questions to answer on the same day each year, and resist changing the wording.
- Write one sentence describing what you expect to be true in a year, then read it in a year and mark whether you were right.
- Keep a separate list of the questions you skipped, and treat it as the agenda rather than as a failure.
- Note which answers came from you and which came from a parent, a partner or a peer group.
- Read your twenty three year old answers at twenty nine before you write off the decade as wasted. Most people have moved much further than they think.