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FIFTEEN CHAPTERS

Work Love Friendship Money Parenthood Caring for a parent Something ending Waiting on something Measuring up Who you are becoming Where you came from Home The body Faith and meaning An ordinary day

Work20 QUESTIONS

  1. What are you counting down to?
  2. Who at work knows what you are actually like?
  3. What are you good at that your job has no use for?
  4. What is the last thing that made you feel competent?
  5. What is the story your calendar tells about what you value?
  6. What did you used to be good at that nobody there knows about?
  7. What does a good day at work actually consist of, hour by hour?
  8. What are you working toward, and is it still the thing you want?
  9. What did you say yes to that you should have thought about longer?
  10. What would you be doing if the last five years had gone differently?
  11. When did you last do something at work you were proud of, and who saw it?
  12. What would your closest colleague say you are best at, and would you agree?
  13. Who is depending on you at work, and does that feel like weight or purpose?
  14. What are you better at than this job will ever need, and where did you learn it?
  15. When did you last go a whole day without tension anywhere, and what was that day?
  16. What did you think this job would be before you had it, and when did that change?
  17. What would you tell someone about to take this job, and what would you leave out?
  18. What would you want to be doing at fifty-five, and what would have to change first?
  19. What is the difference, for you, between liking the work and liking being good at it?
  20. What part of the job would you miss if you left tomorrow, and does anyone there know that?

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Love20 QUESTIONS

  1. Who were you when you met?
  2. Who are you being patient for?
  3. When did you last choose them on purpose?
  4. What do you do that makes them feel known?
  5. What do you know about them that nobody else does?
  6. Who is waiting alongside you, and do they know it?
  7. Who did you think about today, and did you tell them?
  8. What would you want to be doing together in ten years?
  9. What would you miss most, and have you ever told them?
  10. What would a good week between you actually look like?
  11. What is the thing you do for them that nobody else would notice?
  12. When did you last ask them something you did not know the answer to?
  13. When did you last feel chosen, and what did they do that made it land?
  14. Who do you feel most like yourself with, and what makes that possible?
  15. When did you last say the true thing out loud, and what did it cost you?
  16. What do you need that you have not asked for, and what stops you asking?
  17. What did somebody get right about you recently, and did you let them know?
  18. Who makes you feel like the good version of yourself, and why that person?
  19. What has somebody done for you recently that they would not even remember?
  20. What have you got better at in this relationship, and what have you got worse at?

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Friendship20 QUESTIONS

  1. Who have you known the longest?
  2. Which friendship survived something?
  3. Who have you been meaning to write to?
  4. Who has been consistently kind to you?
  5. Who did you used to talk to every day?
  6. Who has changed more than you expected?
  7. What do you do when a friend is struggling?
  8. What was the last good conversation you had?
  9. What group of people do you miss being part of?
  10. Who did you lose touch with for no reason at all?
  11. Who do you keep meaning to introduce to each other?
  12. What do you do together that you would not do alone?
  13. Which of your friendships is easiest, and why that one?
  14. What did you last do for a friend that took real effort?
  15. Which friendship takes effort now that used to take none?
  16. Who would you call at two in the morning, and have you ever?
  17. What did a friend once say to you that you still think about?
  18. What would your friends say you are like, and would they be right?
  19. Who have you not seen in a year that you would still call a friend?
  20. What do you talk about with your friends that you talk about with nobody else?

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Money20 QUESTIONS

  1. What are you building that is not money?
  2. When did you last feel that you had enough?
  3. What are you owed, and have you asked for it?
  4. What is the money for, once the bills are paid?
  5. What does the money actually represent right now?
  6. What did you go without this year, and did it matter?
  7. What are you saving for that you can actually picture?
  8. What are you paying for that you no longer use or want?
  9. What are you putting off that is not actually about money?
  10. If the money were the same, what would you rather be doing?
  11. What does not being able to afford it actually mean to you?
  12. What did this year cost, and what did you actually get for it?
  13. What have you told yourself you will do when you can afford it?
  14. When did you last feel generous, and what made it easy that day?
  15. Who is better with money than you, and what do they do differently?
  16. What did you say no to this year that you wish you had said yes to?
  17. What are you working toward that you could not explain to a stranger?
  18. What is the smallest luxury that makes a real difference to your week?
  19. Who in your life talks about money honestly, and what have you learned from them?
  20. What would you do with a year of not having to earn, and how long before you got restless?

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Parenthood20 QUESTIONS

  1. What are you tired of that nobody sees?
  2. What will they remember about this house?
  3. What are you looking after that needs you?
  4. What would they say you are like in the mornings?
  5. What do you want them to remember about this year?
  6. What are you getting right that nobody has mentioned?
  7. What do they already understand that you did not expect?
  8. What do you want to still be doing together in ten years?
  9. What have you let go of that you thought you never would?
  10. What do you know about them that nobody else has noticed?
  11. What did you plan to do differently, and how is that going?
  12. What are you doing that your parents did, without meaning to?
  13. What are you proud of in them that has nothing to do with you?
  14. What did you give up that you did not expect to mind giving up?
  15. What would you want them to know about this year when they are thirty?
  16. What did somebody do for you as a child that you are doing for them now?
  17. When did you last have a thought that was only yours, and where were you?
  18. What did today actually look like, and what would somebody watching have noticed?
  19. What has been harder than anybody warned you about, and who could you say that to?
  20. What has surprised you about yourself, and would anyone who knew you before believe it?

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Caring for a parent20 QUESTIONS

  1. What still makes them laugh?
  2. What did they used to be like?
  3. What made you laugh this week?
  4. What small thing makes it easier?
  5. What would you do with a free day?
  6. What does a good day look like now?
  7. What do you talk about with them now?
  8. What has surprised you about yourself?
  9. What did they teach you that you still use?
  10. What do you do to get through an afternoon?
  11. What does anybody outside this not understand?
  12. Who have you leaned on, and have you thanked them?
  13. What is the thing you are most tired of explaining?
  14. What was a good moment this week, even a small one?
  15. When did you last do something purely for yourself?
  16. What do you need that you have not asked anybody for?
  17. What is the kindest thing anybody has said to you about this?
  18. What have you found that helps, that you would tell somebody else?
  19. What assumption about this situation do you find yourself correcting?
  20. What do you want to remember about them that has nothing to do with this?

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Something ending20 QUESTIONS

  1. What have you outgrown?
  2. What have you replaced it with?
  3. What did you find out you could do?
  4. What are you glad you did, even now?
  5. Who has been good to you through this?
  6. Who understood without having to be told?
  7. What has got easier without you noticing?
  8. What would you go back and say differently?
  9. What would being over it actually look like?
  10. What did you keep that you should have let go of?
  11. When did you last think about it without meaning to?
  12. When do you still catch yourself, and what sets it off?
  13. What do you want the next version of this to look like?
  14. What are you doing now that you could not have done before?
  15. What would you do differently, and what would you do the same?
  16. What would you tell somebody one week into what you went through?
  17. What did it give you that you would keep, even knowing how it ended?
  18. What is the first thing you did afterwards that felt like yours again?
  19. What is still true about them that you would say out loud to a stranger?
  20. What do you want to be different next time, and what would you have to change to get it?

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Waiting on something20 QUESTIONS

  1. Who is waiting on you?
  2. What did you assume would have happened by now?
  3. What have you already built while you were waiting?
  4. What would you do this month if the answer never came?
  5. What would this year look like if you stopped counting?
  6. What does settled mean to you, and who taught you that?
  7. What have you been promising yourself you would get to?
  8. What did you turn down, and would you turn it down again?
  9. What has waiting taught you that arriving would not have?
  10. What would you tell someone else in exactly your position?
  11. What would you tell somebody who has been waiting even longer?
  12. What is something you thought you would have figured out by now?
  13. What is the smallest piece of it you could have started already?
  14. What are you saying no to while you wait, and is that on purpose?
  15. What are you doing in the meantime that you would keep either way?
  16. What would make this year count even without the thing you are waiting for?
  17. What would somebody who disagreed with your decision say, and are they wrong?
  18. What advice would you give somebody in your exact situation, and why is it hard to take?
  19. What has happened while you were waiting that you did not plan for, and would you keep it?
  20. What did twenty-two-year-old you expect this year to look like, and what did they get wrong?

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Measuring up20 QUESTIONS

  1. Whose praise do you still replay?
  2. What are you good at that nobody rewards?
  3. Who do you want to impress, and why them?
  4. Whose ordinary life do you actually admire?
  5. When did you last stop scrolling and feel worse?
  6. Who would be surprised by how your life turned out?
  7. What do you notice first about other people’s lives?
  8. What did you want at twenty that you no longer want?
  9. What do you have now that you once would have envied?
  10. What would you do with a year nobody would hear about?
  11. What have you done that you have never got credit for?
  12. When did you last feel behind, and behind what exactly?
  13. What are you behind on that only you are keeping track of?
  14. What have you achieved that you have not stopped to notice?
  15. What does success look like for you now, as opposed to then?
  16. What would you post about, and what would you never post about?
  17. What do you assume other people have worked out that you have not?
  18. Who have you stopped comparing yourself to, and when did that happen?
  19. What do you have that somebody else would envy, and do you notice it?
  20. Which part of your life would look worst from outside, and is it actually bad?

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Who you are becoming20 QUESTIONS

  1. What have you got braver about?
  2. What do people get wrong about you?
  3. What did you get right about yourself early?
  4. What are you good at that you never mention?
  5. What are you no longer interested in explaining?
  6. What have you changed your mind about this year?
  7. What would change if your job did not have a title?
  8. What are you curious about that has no use whatsoever?
  9. What did this year cost you, and what did it give you?
  10. What do you know now that would have helped a year ago?
  11. What did you think would feel different once you got here?
  12. What would you want someone to know before they loved you?
  13. What would you be doing right now if nobody ever found out?
  14. What would you do if you were not worried about looking foolish?
  15. What did you believe at twenty-five that you would argue with now?
  16. What would the version of you from five years ago think of this year?
  17. What are you doing now that would have embarrassed you at twenty-five?
  18. What would you be doing if nobody ever asked what you do for a living?
  19. What would somebody who met you last year say you were preoccupied with?
  20. What have they taught you about patience that you did not want to learn?

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Where you came from20 QUESTIONS

  1. Who did you learn to apologize from?
  2. Who told you this was how long it takes?
  3. What did you inherit, and what did you build?
  4. Who taught you what you believe about earning?
  5. What was the house like on an ordinary evening?
  6. What is the thing you swore you would never do?
  7. What did somebody see in you before you saw it?
  8. What do you do at their age that they never did?
  9. What have you kept of theirs, and why that thing?
  10. What would they make of how you spend your time now?
  11. What has changed between you in the last five years?
  12. What would a good conversation with them look like now?
  13. What would a good version of this relationship look like?
  14. What did you learn to do because nobody else was going to?
  15. What are you responsible for now that you did not used to be?
  16. What do you do at Christmas because it is what was always done?
  17. What do you catch yourself saying that you swore you never would?
  18. What did a good day look like when you were ten, and who else was in it?
  19. What are you becoming that would surprise the people who knew you first?
  20. Who in your life is having a harder year than you, and what do you know about why?

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Home20 QUESTIONS

  1. Which room do you avoid?
  2. What do you do first when you get in?
  3. What have you made here with your hands?
  4. What makes somewhere feel like home to you?
  5. What did you imagine your home would be like?
  6. What is the best room you have ever lived in?
  7. What is the best thing about the morning here?
  8. What did home smell like when you were a child?
  9. What do you always mean to do here and never do?
  10. Which neighbor do you know, and which do you not?
  11. What is the story of how you ended up in this place?
  12. Where do you imagine yourself in ten years, physically?
  13. Which place have you only visited and still think about?
  14. What is the noise of this place that you no longer hear?
  15. What have you moved from house to house without ever using?
  16. What is the furthest you have lived from where you started?
  17. If you could keep one view from your life so far, which one?
  18. What would you miss about where you live if you left tomorrow?
  19. What do you love about this place that you would struggle to explain?
  20. What would you change about where you live if money were not the issue?

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The body20 QUESTIONS

  1. What are you looking after well?
  2. When do you feel most at home in it?
  3. Where in your week do you actually rest?
  4. What does rest actually look like for you?
  5. What are you grateful your body did this year?
  6. What did you used to do that your body misses?
  7. What time of day do you feel most like yourself?
  8. What have you been meaning to ask someone about?
  9. What have you got worse at, and does it matter to you?
  10. What did this week cost you, and what did it give back?
  11. What does tired mean for you, and is that the word for it?
  12. What have you been meaning to change for longer than a year?
  13. What have you been meaning to book, and what is stopping you?
  14. What does your body do differently than it did five years ago?
  15. What would you do with more energy, and what does that tell you?
  16. What do you buy when you are tired, and what is it standing in for?
  17. What is the most alive you felt this month, and what were you doing?
  18. When did you last move for the pleasure of it rather than for a reason?
  19. When did you last feel properly rested, and what was different that week?
  20. What would you like to still be able to do at seventy, and what would it take?

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Faith and meaning20 QUESTIONS

  1. What are you hoping for?
  2. Who do you think of as good?
  3. What is your version of a Sunday?
  4. What do you do on the worst days?
  5. What have you stopped arguing about?
  6. What makes you feel part of something?
  7. Where do you go when you need to think?
  8. What ritual do you keep, however small?
  9. What makes you feel small in a good way?
  10. What do you want to be doing when you are old?
  11. What do you find yourself thanking, when you do?
  12. What is the last thing that made you feel lucky?
  13. What feels bigger than you, in a way you do not mind?
  14. What gives you the sense that things might be all right?
  15. What is the most generous thing anybody has done for you?
  16. What are you doing with the part of life that is not work?
  17. What practice have you kept that you cannot fully explain?
  18. When did you last change your mind about something important?
  19. When did you last feel certain about something that mattered?
  20. What do you do that connects you to people you will never meet?

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An ordinary day20 QUESTIONS

  1. What are you glad you can still do?
  2. Who helped and did not make a thing of it?
  3. What did this week look like from the outside?
  4. What does a good morning feel like, physically?
  5. What is the best part of an ordinary Tuesday for you?
  6. What does your body do well that you never acknowledge?
  7. What would you tell somebody about the street you live on?
  8. What routine would you defend if somebody tried to take it?
  9. Who helps you with them, and have you thanked them properly?
  10. What do you own that you would replace the same day if it broke?
  11. What is the best half-hour of your week, and what makes it good?
  12. What have you learned this year that has nothing to do with work?
  13. What does your body do well that you have never once thanked it for?
  14. What has changed in the last year that you did not notice happening?
  15. What would a good Saturday look like, and when did you last have one?
  16. What is the most useful thing anybody ever taught you, and who was it?
  17. What would a stranger think you were good at, watching you for an hour?
  18. What are you reading or watching, and what does it say about where you are?
  19. What are you better at than almost anyone you know, and does it ever come up?
  20. What is the most ordinary part of your week, and what would you miss about it if it stopped?

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