I believe a year is good when you spend more time doing the things you want to be doing than the things you don’t want to be doing. This is a simple definition, of course, but it’s just one measuring stick to evaluate the subjective “goodness” of the year.

With that, here are some questions I’m asking myself as the year winds down to identify what I’m glad I did and what I wish I hadn’t done. I hope they’re helpful to you, too.

1. What’s something you said yes to that, as the day approached, you regretted committing to?

2. What’s something you really wanted to attend but couldn’t that, as the day approached, you were relieved you didn’t go?

3. What did you have to do this year that you weren’t looking forward to that after you did it, you were really glad you did?

4. What did you consistently do this year that, if asked to share, you’d be embarrassed to tell the person you respect the most? (Embarrassed not as in “I take bubble baths every Sunday,” but embarrassed as in, “I can’t believe I’m still lashing out like that,” or, “I can’t believe I spent $4,500 on Door Dash.”)

5. What books, movies, or other forms of media/entertainment had a profound impact on your worldview? Did a specific character or storyline have a unique impact? Why?

6. What opportunities did you miss out on this year that, as it turns out, were for the better? Did you want to move forward with the opportunity, and the other side pulled out? If so, what blinded you to seeing the potential downsides? Or did you decide not to move forward for a specific reason? If so, what did you see that were red flags or potential second-order effects that you didn’t want to encounter?

7. What’s an area of your life that you spent an enormous amount of time on and are glad you did? What did you sacrifice to spend that time? Was it worth it?

8. What area in your life did you neglect the most this year? Will you neglect the same area in 2024 so you can focus on other things, or were there big problems with neglecting this area in 2023 that you want to prevent?

9. What was this year's biggest problem or “thorn in your side”? Did you create that problem? If so, how can you prevent that from happening in the future? If not, how are you handling the effects? Are you focusing on elements you can’t control or trying to make the best out of the situation you’ve been given? Are you resentful, wishing things were some other way? (They aren’t and never will be, so stop being resentful and try to do your best with what you have. Things probably won’t change overnight, so stop wishing they would.)