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.)




Some questions to ask yourself

- Was there an objective reality that existed whether or not we could ever observe it?
- Were there laws that restored strict causality to phenomena that seemed inherently random?
- Was everything in the universe predetermined?
- When do political parties start being a bad idea?
- Why don't we want the government controlling the internet but we're okay with them controlling our education system?
- How is it that outcomes can be likely and not happen and outcomes can be unlikely and still happen?
- Is a democracy possible in the information age? Or has social media and technology changed the way humans function in a "democracy" and policy hasn't caught up yet?
- Where do jokes come from?
- How many people do I admire that are actually miserable?
- Which people know what the right answers are, but no one listens to because they either 1. Don't look the part 2. Don't act like the part 3. Don't talk like the part?
- Is there really a difference between a more-disciplined person and a less-disciplined person, or do they just experience their temptations in different ways?
- Why isn't anyone building something like the Statue of Liberty, The Eiffel Tower, or The Great Bridge anymore? The coolest thing in recent years may be modern looking skyscrapers.
- How is it some things existed in the past but there's no record of them in the present (online)?
- There are a certain set of questions/problems that every person is faced with: how to choose a spouse, how to pick a career (and when to leave the one you're in), how to deal with difficult family members, how to deal with losing someone you love, how to enjoy life outside of work, and many more. Why is there no *Thesis on Life* or an almanack that answers these questions? Tim Ferris's *Tribe of Mentors* is the closest thing I'm aware of and it's still a long way of. This would be a really, really fun project to work on.