Questions to Ask Yourself About Your Career
For anyone taking stock of their working life, whether restless, quietly bored or weighing up an offer: 54 questions to ask yourself about your job and where your career is heading. They run in the order a review goes: the job as it actually is, how it feels, what you are learning, money and limits, a group of career questions to ask in your 30s, and what to do next. They lean on evidence from the last few weeks more than on imagining an ideal job, and several are uncomfortable on purpose.
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The questions
Each question, and why to ask it
The job now
What was my best day at work in the last month, and what was I doing?
Why ask it
Starting from a real day stops you inventing an ideal career that has never existed. When the best you can name is a day spent away from your desk, or no day comes to mind at all, you already have a finding.
Which tasks do I quietly push to Friday afternoon?
Why ask it
What you put off is a fair map of what you dread, and the pattern matters more than the individual task. Admin you avoid is an annoyance; avoiding the central work of your role is a different problem.
If my job description were rewritten to match what I actually do, what would it say?
Why ask it
Roles drift, usually toward whatever the organization is short of. Writing the honest version shows how far you have moved from what you were hired for, and whether the drift has been toward work you want more of.
What did I spend most of last week on, and how much of it did I choose?
Why ask it
Look at your calendar rather than your memory, which flatters the interesting parts. A week that is mostly other people's meetings explains a feeling of pointlessness better than any question about purpose.
What do colleagues come to me for, and do I want to keep being that person?
Why ask it
Your reputation is built from these requests, and it quietly decides which work reaches you next. Being the reliable fixer for something you are tired of is how people end up ten years into a specialism they never chose.
Which part of my job would I keep doing if nobody were checking?
Why ask it
Whatever you would do unprompted is the part that still belongs to you. An honest answer of nothing is not proof of laziness; more often the job has turned into meeting other people's deadlines and little else.
What did I make, fix or decide this month that I could point to?
Why ask it
Some jobs leave a trail of finished things and others dissolve into messages and meetings. With nothing to point at, work out whether the role is built that way or this particular month was eaten by other people's priorities, because the remedies differ.
Who do I deal with most days, and would I choose them again?
Why ask it
The two or three people you talk to daily shape your mood more than the organization chart does. Keep them separate from the company at large. Liking the first and distrusting the second is common, and so is the reverse.
How do I describe my job to a stranger, and which part do I leave out?
Why ask it
The edited version shows what you are proud of, and the omission shows what bores or embarrasses you. Leading with the employer's name instead of the work suggests the name is doing some of the holding.
How it feels
Am I bored, exhausted or in the wrong job?
Why ask it
The three feel alike from the inside and call for different responses: more scope, rest, or an exit. Mistaking exhaustion for a wrong career can lead to a large change with the same tiredness waiting on the other side. Exhaustion that a proper break does not shift is one to take to a doctor before a recruiter.
What do I complain about most, and could it be fixed where I am?
Why ask it
Write the complaint down, then say who would have to do what for it to stop. Some answers turn out to be one conversation away, and others reveal that the thing you dislike is the business model, which no new manager will change.
How do I feel on Sunday evening, and how long has it been that way?
Why ask it
A flat Sunday now and then is ordinary, and the same dread every week for a year is a pattern. Try to date when it began. A feeling that started with a reorganization, a new boss or a change in duties is pointing at its own cause.
Have I felt this way in a job before, and what happened after I left it?
Why ask it
A feeling that has followed you through two or three employers is partly about the kind of work, or about how you work, and another move of the same sort will carry it along. Relief that lasted a year and then faded points the same way. A first-time feeling is better news, since it is more likely to belong to this particular place.
If my manager changed tomorrow, how much of the problem would leave with them?
Why ask it
The question sets one person against the whole job. If most of the trouble would go, the problem is narrower than your career, and managers do move on. If little would change, look at the work or the employer instead.
What does this job cost me outside working hours?
Why ask it
Count specific items: sleep, evenings spent recovering, a short temper at home, exercise dropped, friends not seen. A job you would rate as fine while sitting at the desk can turn out to be an expensive one once those are on the page beside it.
When did I last feel proud of something at work, and who knew about it?
Why ask it
There are two answers in here. A long gap since the last time says something about the work, while pride that nobody saw says something about recognition, which is the more fixable of the two and something you can raise.
Do I believe in what my employer sells or does?
Why ask it
You do not need a calling. Still, working against your own judgment every day wears on people in a way that is easy to mistake for tiredness. 'It is useful enough' is a perfectly good answer, and changing the subject when friends ask about the product is not.
What would I miss if this job ended next month?
Why ask it
Ask it as a counterweight to the list of complaints. Particular colleagues, control over your day, predictable hours and a short commute are typical answers. Whatever you name belongs on the list of things a next job has to offer too, and it is the list people forget to check.
Growth
What have I learned in the last six months that another employer would pay for?
Why ask it
The answer separates progress from accumulated tenure. Come back to it every six months: a blank answer twice running is worth taking seriously, especially in a field where skills date quickly.
Which of my skills only make sense inside this company?
Why ask it
Knowing an internal system, a legacy process or a particular set of politics is valuable here and worth little elsewhere. When most of your expertise is of that kind, your options are narrower than your seniority suggests, and the repair is to learn one thing the wider market has a name for.
Whose job here would I want next, and what does it mean if the answer is nobody?
Why ask it
Look at the actual people one and two steps above you and not at the ladder on paper: their hours, their meetings, what they talk about at lunch. When none of those lives appeals, promotion here is not what you want, however good the title would look.
What am I getting better at by staying, and what am I getting worse at?
Why ask it
Most jobs quietly erode something: writing, technical depth, patience, contact with customers. Naming the loss gives you a specific reason to act, rather than a general restlessness you cannot argue with.
When was I last properly out of my depth at work?
Why ask it
Being stretched is uncomfortable, and it is also how new ability arrives. A gap of years means the job has become one you can do half asleep, which is restful for a season and then starts to cost you.
Who gives me honest feedback, and what did they last tell me?
Why ask it
Feedback you cannot quote is probably feedback you are not getting, and a polite annual review does not count. You may have to go and ask one person one narrow thing, such as what you should stop doing in meetings.
If I applied for my own job today, would I get it?
Why ask it
Read how the role is advertised now, here or at a competitor, and compare yourself with the posting. Getting it easily suggests you have outgrown it. Falling short suggests the field moved while you were busy, and the posting names what to catch up on.
What do I want to be known for in five years, and is my current work building it?
Why ask it
Choose something another person could say about you in one sentence, then hold the last three months of work against it. A job hands you a reputation whether you pick one or not, so the alternative to choosing is being known for whatever landed on your desk.
Is there a ceiling here, and how close am I to it?
Why ask it
Look at where people in your kind of role have gone over the last few years: up, sideways or out of the door. A small firm or a flat team can be a good place to work with nowhere to go, and it is better to know that than to wait for a promotion with no position behind it.
Money and limits
How much money do I actually need each month, and when did I last work it out?
Why ask it
A salary requirement can outlive the life stage that set it: the rent of a city you have left, a loan since paid off. Doing the arithmetic sometimes reveals more room than expected and sometimes confirms that a pay cut is not available, and either result is useful.
What would I have to be paid to still be doing this in five years?
Why ask it
A sharper version of asking whether you are underpaid. Name the figure, then check whether you believe it. No realistic number making five more years acceptable means the problem is the work and not the pay, and a raise would only postpone the decision.
Do I know what this job pays elsewhere, and where did my number come from?
Why ask it
A colleague's guess or a figure from three years ago is not a number. Look at current postings that state pay, published salary surveys for your region and what recruiters quote, and treat the result as a rough range. Being paid well for the market is a legitimate reason to stay, provided you call it that.
If an offer arrived this week, what would it need besides more money for me to say yes?
Why ask it
Write the conditions before any offer exists, because a real one comes with a deadline and a flattering number attached. Three or four is enough: the work itself, who you would report to, the hours, the room to grow. An offer that only beats your pay moves the same complaints to a new building.
If I lost this job on Monday, who would I call, and is that list long enough?
Why ask it
The answer measures something you can only build slowly, so it is better tested while you are still employed. A list made up entirely of current colleagues is the mark of several heads-down years, and one coffee a month with somebody outside the building starts to mend it.
How long could I go without this paycheck, and what does that number let me risk?
Why ask it
Divide your savings by what a bare month costs you, and the result sets the size of experiment you can afford. A short runway is no verdict on the idea; it means the change gets made while you are still employed. Notice pay, severance and unemployment support depend on your contract and your country, so check them before counting on any.
Which of my constraints are real, and which did I inherit from someone else?
Why ask it
A mortgage, a visa, a child's school year and a health condition are real. A degree you feel obliged to use, a parent's idea of a proper job and an industry you have simply always been in are not, though they can feel identical.
Who else depends on what I earn or the hours I keep, and have I asked what they would trade?
Why ask it
It is easy to assume a partner or a family needs the whole salary, when some would trade part of it to have someone home at six and others would not. Ask instead of guessing, because their answer is one of the facts in the decision.
Which benefit or date am I holding on for?
Why ask it
A bonus, shares that vest, pension terms, parental leave, a visa or a course the employer is paying for can each be a sound reason to wait. They differ by employer and country, so read your contract and ask HR how it works where you are. Then check that this is not the fifth such date in a row.
In your 30s
Ten years in, would I pick this field again knowing what I know now?
Why ask it
You chose it with almost no information about the daily work, and you now have a decade of it. A no is not an instruction to leave. It is a prompt to list the parts you would keep, since a move to something adjacent is usually more available than a blank start.
Do I want to manage people, or get better at the work itself?
Why ask it
This fork tends to arrive in your thirties whether you invited it or not, often as a promotion offered as a compliment. Managing is a different job and not a prize for doing the old one well. Find out whether your employer has a senior track without a team, and if not, whether others in the field do.
Which doors are open now that will be harder to walk through at forty-five?
Why ask it
Retraining, a move abroad, a pay cut to start somewhere new, a long course: none of them closes on a birthday, but each tends to get more expensive as obligations pile up. List only the ones you care about. The point is to price them, not to panic.
Am I still chasing a goal I set at twenty-five?
Why ask it
It might be a title, a salary figure or a particular firm's name. Check whether you still want it or are only still pursuing it. Old goals keep their grip long after the person who set them has changed, and retiring one frees a surprising amount of attention.
Who am I measuring myself against, and would I want their week?
Why ask it
By now your classmates' paths have spread far enough apart to make comparison a daily habit: one made partner, another started a company, a third works three days. Before envying the outcome, ask what their Tuesday looks like and what they gave up for it.
How does my work fit the next ten years at home?
Why ask it
Children, aging parents, a partner's career and where you want to live often press on this decade in particular, and jobs differ in how far they bend on travel, shifts and leave. Answer for the life you expect, which may include none of those. Ask how leave and flexible hours work at your employer instead of assuming.
Have I become too expensive or too specialized to move easily?
Why ask it
Seniority can narrow your options, because fewer roles exist at your pay and a deep specialism may have only a handful of buyers. Count the employers in your region who would hire you at your present level. A short list is a reason to widen your skills while that is still optional.
What did I want from work at the start that I have quietly stopped expecting?
Why ask it
Perhaps to make things, to be useful to someone you could see, or to learn from a person better than you. Some hopes you dropped for good reasons and others just wore away. Sort them into those two piles, because the worn-away ones are often what the restlessness is about.
What next
Am I trying to get away from this job, or toward something I can name?
Why ask it
Both are honest reasons to move, but they shop differently. Getting away makes almost any offer look good, including one with the same problem under a new logo, while moving toward something gives you a way to tell two offers apart. With nothing named yet, naming it comes before any applications.
What have I turned down in the last year, and what was I protecting?
Why ask it
Refusals show your real priorities more accurately than any list of values. A year with no refusals in it has probably been spent on other people's plans.
Is the change I am considering a new employer, a new role or a new field?
Why ask it
Those are three sizes of move, costing roughly a job search, a sideways step and a period of retraining. Pick the smallest one that would fix your main complaint about the job you have. The biggest is the most satisfying to daydream about, which is not a point in its favor.
What exactly would I ask my manager for, in one sentence?
Why ask it
Until it is a sentence, nobody can grant it. 'More growth' is not a request, while 'let me lead the next client project' or 'four days a week from March' is. Writing it also shows whether the thing you want is something this employer could give at all.
What am I afraid would happen if I asked for what I want, and how likely is that really?
Why ask it
Write the feared outcome as a sentence, then estimate its odds and its cost. Often the realistic worst case is an awkward conversation and a no, a lower price than another year of not asking. Where you have watched people be punished for asking, that is information about the employer and belongs in the decision.
If I stay another year, what has to be different by the end of it?
Why ask it
A vague dissatisfaction becomes a test with a date on it. Write down the two or three specific changes, put a reminder in your calendar, and treat their absence as a decision rather than as bad luck.
What is the smallest version of my next idea that I could test without quitting?
Why ask it
A move can usually be tried as an adjacent step before a leap: a side project, an internal transfer, a course, one client, two weeks of shadowing someone. Read what your contract says about outside work before taking a paying client. An idea whose smallest test still feels too big may be a daydream you enjoy more than a plan.
Who is already doing what I think I want, and what have I asked them?
Why ask it
An hour with someone in that work replaces weeks of speculation. Ask about their worst week and what a newcomer earns now. If you have been turning the idea over for a year without contacting one such person, sending that message is the next step.
In ten years, which would I mind more: having tried this and failed, or ten more years exactly like this one?
Why ask it
It is only a fair question once you have a specific change in mind, so answer it about that one. The comparison does the work: staying has a cost too, and this is where you find out whether it is the safe option you have been treating it as.
What one thing will I do about this in the next seven days?
Why ask it
Keep it small enough to finish: a salary lookup, a message to a former colleague, a meeting booked with your manager, an hour on your resume. A career review that ends without a dated action tends to be repeated word for word a year later.
Doing This Reflection Properly
Practical guidance for the conversation itself
How to Get Honest Answers
Take the six groups in order
The job now and How it feels are about evidence, and they are the questions to ask yourself about the job you have before you think about any other. Growth and Money and limits measure what staying is worth and what leaving would cost. Only then does What next have something to work with. Skipping straight to the last group produces a plan built on a mood.
Count the In your 30s group from when you started, not from your birthday
That group is written for someone roughly a decade into working life, when the choice between managing and specializing turns up and life outside work starts making claims of its own. If you began late or changed fields, count from when you entered this line of work. Someone three years in can leave the group for later, and someone at forty-two will find most of it still applies.
Do it on an ordinary Tuesday
Answers written the evening after a bad meeting recommend quitting, and answers written after a good review recommend staying. Pick a normal week, and if something dramatic has just happened, wait two weeks.
Separate the job, the manager, the company and the field
Usually only one of the four is the problem, and the fix differs completely: a change of team, a new manager, a new employer, or retraining. Going straight to the largest option is how people end up making an expensive change that solves nothing.
Use your calendar and your bank statement as evidence
Both are records of what you actually did and what you actually needed, and both contradict the story you tell yourself. Read the last month of each before answering anything about time or money.
Write the answers down and date them
The value comes from rereading them in six months, when you can see whether nothing has changed or whether you have simply stopped noticing. Undated reflection tends to be repeated indefinitely.
Talk to two people who left, not two who stayed
People still in the job tend to defend the choice they are living with, while people who left can tell you what they gave up and what they got for it. Ask them what surprised them and what they would not do again.
Two Ways to Use These
A two-hour session, on paper
- 1Twenty minutes on evidence: last month's calendar, what you actually spent your hours on, what you avoided.
- 2Thirty minutes answering The job now and How it feels, without deciding anything.
- 3Ten minutes labeling what you have written: fixable here, fixable elsewhere, not fixable.
- 4Thirty minutes on Growth, then Money and limits, with real numbers. Add In your 30s if it fits.
- 5Twenty minutes on What next, ending with the one-year test: what must be different, and by when.
- 6Ten minutes choosing one action for this week, small enough that you will actually do it.
Testing a change without quitting
- 1Name the specific thing you think you want more of, in terms of tasks rather than job titles.
- 2Find someone doing it and ask what their worst week looks like.
- 3Get a small piece of it: an internal project, a volunteer role, one paying client, a short course.
- 4Give it a fixed trial period and note whether you look forward to the hours or resent them.
- 5Decide at the end of the period, on what happened rather than on how you felt at the start.
Common Traps
- Deciding in the week of a performance review, a bonus, or a reorganization. Strong feelings make good notes and bad decisions.
- Treating a raise as the answer to boredom. It buys some goodwill for a while and leaves the work exactly as dull as it was.
- Asking only people in your own field. They chose to stay in it, so leaving tends to sound like a loss when they describe it.
- Comparing your worst days with other people's public accounts. Nobody posts about the parts of their work they avoid until Friday.
- Waiting to feel certain. Certainty tends to arrive after a change rather than before one, so the practical question is whether the smallest next step is reversible.
- Answering as the person you were when you chose this work. Preferences at twenty-two are a poor guide to what suits you at thirty-five, and much of the guilt about switching comes from honoring them.