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Questions Worth Sitting With — A Year-End Reflection Guide

These questions are worth returning to at any time of year — though they’re particularly useful at transitions: the end of a year, the start of a new one, a birthday, or any moment when you want to get a clearer sense of where you’ve been and where you’re headed.

You don’t need to answer all of them. Read through slowly and notice which ones land. Sometimes a single question that stops you is more useful than working through the whole list. You might journal your answers, sit quietly with them, or talk them through with someone you trust.

Before you begin, you might find it useful to try the Clearing a Space focusing practice — a short guided practice for setting down what you’re carrying and creating some inner quiet before you reflect.


Looking back

  1. What is the most important lesson you learned this year?
  2. What is the best thing that happened?
  3. What challenges did you overcome?
  4. What new skills or capacities did you develop?
  5. What did you enjoy the most?
  6. What was your favourite moment?
  7. How did you have fun?
  8. What new habits or practices took root?
  9. What are you most proud of?
  10. What did you learn about yourself?
  11. How did you live by your values — and where did you fall short of them?
  12. How did your relationships evolve — with family, friends, colleagues?
  13. What was the best decision you made?
  14. How did you fail — and what did that teach you?
  15. What got in the way?
  16. What would you do differently?
  17. How are you different than you were a year ago?
  18. What did you do for your physical and mental health?
  19. Who or what had the biggest impact on your life?
  20. What did you let go of?
  21. What did you leave unfinished — and was that okay?
  22. What are you grateful for?
  23. What was the best compliment you received?
  24. What energised you? What drained you?
  25. How did you practice self-compassion?

Looking forward

  1. What is your intention for the year ahead?
  2. What do you want to continue?
  3. What do you want to change?
  4. How do you hope to be different by this time next year?
  5. What would it mean to step outside your comfort zone?
  6. What do you want to experience?
  7. What do you want to accomplish?
  8. What will your focus be?
  9. Which relationships do you want to invest in?
  10. What opportunities do you want to create?
  11. How will you contribute to or support others?
  12. What qualities in yourself do you want to strengthen?
  13. What do you want to learn?
  14. How will you take care of yourself?
  15. What will you say no to?
  16. Who will you ask for help and support?

A note on how to use these

Reflection works best when it’s unhurried. If you can, set aside an hour — somewhere quiet, with something to write in. You don’t need to be systematic about it. Start with whatever pulls at you and see where it leads.

And if you notice a question that you’d rather skip — that’s often the one worth staying with a little longer.

If the reflection surfaces something about anxiety or how you’re managing your mental health, the free Name It to Tame It anxiety course is a good self-paced starting point. And if what comes up feels like it deserves more than a journal entry, individual counselling is available in Squamish and online across BC.

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