Retirement
Questions to ask about purpose in retirement

These questions are for anyone planning retirement, and for the coaches who help them think it through.
There is no right answer hiding in the list. Write on the ones that catch. Leave the rest.
What you want to keep
The job can end without the useful parts of it ending too.
Which parts of your working days still feel like yours?
Think about what you'd want to carry into retirement from your working days. Tasks, habits and moments all count.
- Think about a week at work when you felt most like yourself. What were you doing?
- Which part of your day would you happily keep without the pay?
- Finish this line: 'Even after I retire, I want to keep...'
What do people already come to you for that you would miss if it stopped?
This is about being useful in ways people already value. Small things count.
- Think of the last time someone called you for advice. What was it about?
- What do friends or colleagues rely on you to do?
- Which kind of request do you secretly enjoy getting?
What have you gotten good at that you still want to use, even if nobody is paying you to do it?
Your skills don't stop at retirement. Name the ones you'd still want to use.
- Think of something you can do that others find hard.
- Which skill would you hate to lose?
- Picture using it for a neighbor, a group or yourself. What does that look like?
What do you want to keep in your life once work no longer sets your schedule?
Some of what work gave you can outlast it. Name the people, places and habits you want to hold on to.
- Think about the coffee spot, walk or lunch friend tied to your workday.
- Which routine gives your week its shape right now?
- Who would you hate to lose touch with?
What you want to leave behind
Some of what you are tired of was never a choice you made.
What have you kept doing because it was expected, not because you wanted it?
Some habits came from a role, not from you. This is a chance to notice them.
- Think about a task you do because 'that's what someone in my job does.'
- Which obligation would surprise people to hear you dislike?
- Finish this line: 'I only do this because...'
Which responsibilities are you ready to put down?
Name the duties you're ready to stop. You don't need to explain why.
- Think about the task you put off most often.
- Which meeting or role would you be relieved to hand over?
- What will you be glad never to be on call for again?
Which responsibility would you feel guilty putting down?
Some duties are hard to let go even when you're tired of them. Naming them helps you decide.
- Think about someone who depends on you for something regular.
- Which commitment would you keep out of loyalty?
- Is there a role you'd hand over only once you knew it was in good hands?
What kind of busy are you finished with?
Not all busy is the same. Name the kind that drains you.
- Think about a week that was full but empty. What filled it?
- Is it rushing, juggling, waiting, or something else?
- Which kind of busy would you still welcome?
Without your job title, what part of how you act at work would you be glad to drop?
Many roles come with a way you're expected to act. This asks which parts of that you won't miss.
- Think about how you speak or dress at work that isn't quite you.
- Which expectation of your role do you find most tiring?
- Finish this line: 'Once I'm retired, I won't have to...'
How you want your days to feel
An empty calendar is not the same thing as a good day.
What would a good ordinary Tuesday look like if you planned it yourself?
Picture a normal day, not a vacation. Walk through it from morning to night.
- What time do you wake up, and what do you do first?
- Who do you see, and where do you go?
- How do you want to feel when you go to bed?
How much of the day do you want planned, and how much do you want left open?
Some people like a full calendar, others like open space. Most want some of each.
- Think about a weekend that felt just right. How much of it was planned?
- Do you feel better with a list or without one?
- Picture an empty day. Does it feel restful or restless?
Where do you want to spend most of your days?
Place shapes retirement days. Think home, nearby, a new town, or time split between places.
- Think about where you feel most at ease.
- Is it close to family, near nature, or in a busy town?
- Picture an ordinary afternoon. Where are you?
What pace of day feels right to you?
Without work setting the speed, you get to choose it. Notice what feels comfortable.
- Think about a slow day that felt good, and one that felt too slow.
- Do you like to start early or ease in?
- How many things in a day feels like enough?
Which hours of your week do you want to keep for yourself?
Once you retire, others may assume you're free. This helps you name the time you want to protect.
- Think about the time of day you feel sharpest or calmest.
- Which activity would you want to block off and keep?
- Who might ask for your time, and when would you say yes?
Who you want to be around
Work put a lot of people in your week that you did not choose.
Who do you want more time with now that work is no longer arranging the week?
Work decided a lot about who you saw. Now you get to choose.
- Think about someone you keep meaning to call.
- Who do you see too little of right now?
- Which friendship would you like to grow?
Who do you feel most like yourself around?
Some people help you relax into who you are. Name them.
- Think about the last conversation that left you lighter.
- Who can you be quiet with?
- Who knew you before your career?
Who do you still feel you can't fully be yourself around?
This isn't about cutting people off. It helps you notice where you can relax and where you can't yet.
- Think about a gathering where you felt you had to act a certain way.
- Which version of you do certain people expect?
- Who would you like to be more open with?
Where would you like people to know you by name?
Belonging can be small: a café, a club, a street. Think about where you'd like to be a regular.
- Think about a place where you'd like someone to greet you by name.
- Is there a group you've wanted to join?
- Where were you known before, and do you want that back?
If you went quiet for a month, who would you hope reaches out?
This helps you name the people you most want in your circle. It's a list to grow, not a test.
- Think about who checked on you the last time you were sick or away.
- Whose message would you be most glad to get?
- Who would you like to be closer to a year from now?
What you want to contribute
Being useful does not have to look like the job you are leaving.
What have you learned that's worth passing on?
Your experience can be useful to others. It can be a skill, a lesson or a way of seeing things.
- Think about advice you wish you'd heard at 25.
- What do younger colleagues ask you about?
- Which mistake taught you the most?
Who would you most like to pass it on to?
Picture the person or group who'd gain the most from what you know.
- Think about a group you care about, like a school, trade or neighborhood.
- Is there someone just starting out who reminds you of yourself?
- Who would you be proud to help?
What still has your attention when nobody is asking you to look at it?
What you notice on your own time points to what you care about.
- Think about the news story or problem you keep following.
- What do you find yourself fixing, sorting or noticing?
- Which topic do you bring up with friends?
How many hours a week could you give to that before it started to feel like a job?
Giving your time can be good until it starts to feel like an obligation. This helps you find your limit.
- Think about a volunteer role or favor that grew too big.
- How many mornings a week feels like enough?
- What would tell you it had turned into a job?
If the next ten years were for one thing, what would it be?
Pick one thing to give these years to. You can change your mind later.
- Think about something you've said 'one day' about for years.
- What would you want to tell a friend you did in this decade?
- Picture yourself ten years from now. What are you glad you made time for?
SAMPLE
Try a sample from the book
The opening pages and one full theme from Finding a Meaningful Retirement, as a PDF.
Foundpath is a guided written interview that turns answers like these into a written brief. Read the retirement sample, or start your own report.