End-of-Year Reflection Questions for the Procrastinating Perfectionist

There’s an adage I heard once that says, “If you don’t think you have time for a ten-minute walk, you need a twenty-minute walk.”

I originally heard it in the context of taking care of your health, but I think it’s true of reflection, too. If I don’t feel like I have five minutes to plan my day, I probably need ten.

But just because I know this doesn’t mean I’ve been good at it. For the better part of the last decade, I have taken meticulous notes on my own life. I’ve tracked my time both manually and using digital time tracking tools. I’ve journaled regularly, including keeping bullet journals with impressive-for-me consistency since 2016. That all disappeared this year. My life feels like it’s moving faster than ever, and rather than slow down to reflect I… did not do that.

Now that 2023 is ending, I want to take stock of my year, but I don’t have the same meticulous notes that I usually do. So I made an end-of-year reflection for the procrastinating perfectionist, and I wanted to share it with everyone here. If you take me up on this and post it on Medium, tag me! I want to see how it works out for you. But regardless of how you use them, here are some prompts to get you thinking about how 2023 has gone.

I list a few of these prompts as optional. Technically, they all are. But I wanted some to be optional even for myself, depending on if I have the energy to dive deep when I work through this, and I wanted to make that option available to anyone who uses these.

1. In what ways did your year get documented? Think beyond any attempts at planners: social media, Goodreads, emails sent and received, texts, photos, documents, projects in places like Canva… even without taking the time intentionally, it’s likely your life was documented. Write these down as ideas on where to look to reflect on 2023.
2. Which of these would be most helpful in reviewing your year? Don’t hold yourself to specific percentages, but think of the 80/20 rule here: which 20% of possible documentation locations hold 80% of the data you need to reflect?
3. Using only the sources you decided on in step two, document your year month by month. Make a list of what you find: projects started or finished, vacations taken, new work, fun moments, little accomplishments, big shifts, mindset changes, anything that feels relevant. Don’t comment on anything at all at this point. Just list it.
4. OPTIONAL: Looking at each month as a whole, what moments stand out to you? What were, in hindsight, your linchpins? Moments things changed, whether they felt big at the time or not. Did anything change that’s become such a big part of you since that you can’t believe it was less than a year ago?
5. OPTIONAL: What hard moments do you see? Is there direct evidence of them, or are they more evident as a lack (of pictures, planning, emails sent, etc.)? How did you work through these moments?
6. We’ve talked a lot about what you’ve done and experienced, but what did you stop doing? This can be 100% for the better (smoking, assigning moral value to food, saying yes when you meant no), or a definitive step back for you (daily walks, yoga if you usually like it, planning, writing), or something more neutral.
7. OPTIONAL: Choose a few things you stopped this year to write about in more detail. What made you stop? Was it intentional or accidental? Gradual or cold turkey? if it’s a win, take time to celebrate it. If it feels missing from your life now, how can you reinstate it?
8. OPTIONAL: If you started 2023 with any kind of intentions (goals, resolutions, words to live by), or ended 2022 with a reflection on that year, look at them now. With Past You in mind, write a letter to who you were on January 1, 2023. Would that person recognize you? How would they feel about your choices? About how you handled setbacks and challenges?
9. Less tangibly, did you learn anything about who you are or who you’re becoming? how have you embraced the person you’re uncovering?

Again, please let me know if these questions helped you as you reflect!