Questions to ask about a meaningful career

Which hours in the week do you hope nobody cancels?

Think of the meetings, tasks or stretches of time you would protect if your calendar got cut in half. They point to the work you still care about.

• Look at last week's calendar. Which entry would you have been sorry to lose?
• Think about a week when one hour made the rest worth it. What was happening in it?
• Name a recurring hour you'd still show up for on a bad day.

Which parts of your work would you still want to do under a different title, somewhere else?

This separates the work itself from the job wrapped around it. Name tasks, not roles.

• List three things you did this month that you'd happily do for a different company.
• Think about a task you'd explain with pride to a stranger at a party.
• Picture your next job. Which of today's tasks do you hope it includes?

When in your workday do you feel most like yourself?

Look for the moments when you stop watching the clock. Those hours say something about what fits.

• Think about a week when time went fast. What were you doing?
• Is it a time of day, a kind of task, or a certain person nearby?
• Finish this line: 'I feel like myself at work when...'

Which problems do you pick up even when they are not yours to solve?

The problems you keep coming back to often show what you care about most. Small ones count.

• Think of the last time you fixed something nobody asked you to fix.
• What do colleagues come to you for that isn't in your job description?
• Which kind of mess bothers you enough that you step in?

What part of your work did you fall into rather than choose?

Some of what you do now came from habit or a default next step. Name one piece you never really picked.

• Think back to how you got into this line of work. What did you say yes to without much thought?
• Which task would surprise you if you saw it on a list of things you chose?
• Finish this line: 'I never decided to... I just ended up doing it.'

Which responsibility would you hand to someone else tomorrow if you could?

Name the thing you'd give away first. You don't need a plan for who takes it.

• Think about the task you put off until the last possible minute.
• Which part of your week leaves you most tired, out of proportion to its size?
• If you had an assistant for one day, what would you give them?

What are you tired of having to justify at work?

This is about the parts of your work you keep having to argue for. Write down the first thing that comes to mind.

• Think about a conversation at work you've had more than three times.
• Is there a choice you make that people keep questioning?
• What do you wish you never had to explain again?

If this job ended on Friday, which part would you be glad to never do again?

Picture the last day and notice what you feel relieved to leave. Be as specific as you can.

• Think of the email, meeting or report you'd happily never see again.
• What would you not miss on a Monday morning?
• Name one task you'd leave off your next job's list on purpose.

What does a workday you would repeat look like, from the first hour to the last?

Describe an ordinary good day, not a perfect one. Start with when it begins and walk through it.

• Think about a recent day you'd happily have again. What happened in the morning?
• What time do you start, and what's the first thing you do?
• How does the day end, and how do you feel when it does?

How much of that day do you want with other people, and how much on your own?

There's no right mix. This helps you notice how much company keeps you going and how much wears you out.

• Think about a week when you came home with energy left. How much of it was spent with people?
• Would you rather have long stretches alone or short ones between conversations?
• Picture your ideal day as a pie chart. How big is the 'with people' slice?

What pace could you keep up for a whole year without wearing down the rest of your life?

Think about a speed of work you could keep going, not one you'd survive for a month. Sleep, family and health count here.

• Think about a stretch when work felt busy but steady. What made it feel like that?
• When did a busy season start to take from your evenings or weekends?
• How many late nights a month feels fine to you, if any?

Where would you most like to spend your working day?

Place shapes a workday more than people expect. Think about home, an office, outdoors, on the road, or a mix.

• Think about the setting where you've done your best work.
• Picture where you'd like to sit down with your first cup of coffee.
• How far are you willing to travel to get to work each day?

Who is better off when you do this work well?

Name real people or groups, even if you never meet them. It helps to picture one person.

• Think of a time someone thanked you for your work. Who were they?
• Who would notice first if you did the job badly?
• Finish this line: 'Because of my work, someone can...'

Whose problems do you want to keep working on?

Think about the people whose problems you'd still want to work on years from now.

• Think about a client, customer or colleague whose problem you enjoyed solving.
• Which kind of person do you most want to see do well?
• If you switched fields, whose problems would you miss?

Who would you want to work alongside in a normal week?

Think about the colleagues who make the work better. Name types of people if no names come.

• Think about a teammate who made hard weeks easier. What were they like?
• Do you want to work with people who are like you, or different from you?
• Who do you leave a meeting feeling better about?

Where does it matter to you that people know your work by name?

Some people want to be known widely, others only within a small circle. Either is fine.

• Think about a time someone recognized your work. Who was it, and how did it feel?
• Is it your team, your field, your town, or somewhere else?
• Whose good opinion of your work would mean the most?

What are you curious about that this job barely touches?

This makes room for interests your current role doesn't use. Hobbies and side reading count.

• Think about what you read or watch when nobody's asking you to.
• What topic could you talk about for an hour without notes?
• What did you want to know more about five years ago that you still wonder about?

What would you practice if nobody needed a finished result from you?

Think about a skill you'd like to work on without a deadline. It can be small.

• Think about something you'd be happy to be bad at for a while.
• What would you sign up for if a class were free and close to home?
• Picture a slow afternoon with nothing due. What would you work on?

What do people already trust you with that you want to take further?

Start with what you're already known for, then picture the next step up.

• Think of the last thing someone asked you to handle because 'you're good at this.'
• What do you get asked to review, fix or teach?
• If you went one step deeper in that skill, what would it look like?

What skill have you put off learning because your job never needed it?

Name one skill you keep meaning to learn. It doesn't need a reason.

• Think of a course, book or tool you've bookmarked and never opened.
• What skill do you admire in someone else?
• Which skill would make a different kind of work possible for you?

What would any change have to keep safe in your life?

Before you picture a new role, name what has to stay safe. These are your limits.

• Think about what your household relies on from you each month.
• Is there a place you don't want to leave, or a schedule you can't give up?
• Which people need you close by or available?

Who is counting on you to stay steady while you sort this out?

Name the people affected by your choices. This is about seeing them, not about guilt.

• Think about who you'd talk to first if you made a big change.
• Who would feel it if your income or hours changed?
• Who could support you while you work this out?

If you left the part that no longer fits, what would you miss?

Changing one thing can cost you something you value. Name it now so you can plan for it.

• Think about a colleague, routine or perk you'd miss in a new role.
• What do you get from this job that you rarely notice?
• Picture your first month somewhere new. What would you wish you'd kept?

If you could change only one thing about your work this year, what would it be?

Picking one thing makes a change easier to try. Keep it small enough to start.

• Think about the change that would make Monday mornings easier.
• Is it a task, a person, a schedule, or a place?
• What could you try in the next month to test it?