10 End of Year Reflection Questions


The best way to begin the new year is to reflect carefully on the old one.


1. If you had to sum up the past year in one word, what would it be?

This is an exercise in perspective taking. Most of the year we’re in the weeds dealing with issues as they come up. Now’s a chance to zoom out and observe the shape of the forest, not just individual trees…

  • What were the major patterns or trends over the past year?
  • Did your year have a story arc?
  • What word best captures your hopes or aspirations for next year?

2. Who or what got too much of your time in 2025?

Opportunity costs are everywhere: every yes hides a thousand nos.

3. What’s something you want to let go of next year?

For each thing you identify, ask yourself: What do I get out of holding on?

If you don’t understand what need a habit or pattern fills, it’s difficult to get that need met in a healthier way.

4. What’s your favorite memory from the past year?

What does that memory tell you about your values?

5. What’s something you wish you had said this year but didn’t?

Here’s a good New Year’s resolution:

  • Identify 12 important conversations you know you should have but have been avoiding.
  • Have one per month next year.

6. What are you most ashamed of this year?

Our culture (especially mental health culture) seems to think shame is a bad word—and an emotion we shouldn’t feel. I think it’s one of the most important and useful emotions we have. We all do things we’re ashamed of—or avoid doing things we could have been proud of. Getting better requires leaning in.

7. What are you most proud of this year?

Especially for those of us who are good at and enjoy solving problems, it’s easy to get stuck in a habit of immediately moving on to the next problem as soon as we’ve solved the previous one without any pause for reflection and self-commendation, thereby eliminating the opportunity to feel a sense of pride, and all the benefits that come with it.

8. Who helped you the most this year?

Who did you help the most?

Who needed your help most this year?

If there’s a difference, why is that?

9. What’s something you changed your mind about this year?

If you can’t think of anything, what does that mean? What would have to be different next year for you to readily have 3-5 serious answers to that question at the end of the year?

10. What could happen to make next year the best year of your life?

C- Answer: Some amazing thing happens to you.

A+ Answer: You do something amazing.

What kind of story will next year be? What kind of protagonist will you be—hero or supporting character?


Next Steps

If you like this essay, here are a few more from me you might enjoy: