One prompt a day. Thirty-one entries. A year of your life, finally examined.
December has a strange quality. The year isn’t over yet, but it already feels past tense. You start thinking in summaries. What happened? What changed? What didn’t?
Most of us wait until New Year’s Eve to reflect. Then try to create new goals and a few champagne-fueled resolutions.
This happens to me every year. I have a vague sense of what I want to be different, by the second week of the New Year, most of us are right back into auto pilot.
This year, try something different.
The 31-Day Reflection Challenge gives you one journaling prompt for each day of December. Some days you’ll write for five minutes. Some days you’ll need twenty. By December 31st, you won’t just remember your year—you’ll understand it.
How to Use This Challenge
Keep it simple. Answer one prompt per day. Don’t overthink it. Write what comes up, even if it surprises you.
Don’t skip the hard ones. Some prompts will make you uncomfortable. That’s the point. Growth lives in the friction.
Look for patterns. By the end of the month, read back through your entries. What themes keep surfacing? What did you avoid writing about? What surprised you?
If you are reading this too late, no worries. You still can do it. A year review doesn’t have to happen in December only.
The Prompts
Week 1: Looking Back
December 1: What’s the first thing that comes to mind when you think about this year? Don’t filter it—just write.
December 2: What was your biggest win this year? Not what should have felt like a win. What actually did.
December 3: What’s one thing you tried this year that didn’t work? What did it teach you?
December 4: Who had the most impact on your life this year—for better or worse?
December 5: What habit did you successfully build this year? What made it stick?
December 6: What habit did you try to build but couldn’t? What got in the way?
December 7: Look at your calendar from January. What were you worried about then that doesn’t matter now?
Week 2: The Emotional Ledger
December 8: What made you genuinely happy this year? Not content. Not okay. Happy.
December 9: What disappointed you this year? Be specific.
December 10: When did you feel most like yourself this year?
December 11: When did you feel furthest from yourself?
December 12: What conversation do you wish you’d had this year but didn’t?
December 13: Who do you need to forgive—including yourself?
December 14: What are you still carrying from this year that you need to put down?
Week 3: Relationships & Connection
December 15: Who showed up for you this year? How did they do it?
December 16: Who did you show up for? What did that cost you? What did it give you?
December 17: What relationship deepened this year? What made the difference?
December 18: What relationship faded? Was it intentional, or did you just let it happen?
December 19: What’s one thing you learned about someone you love this year?
December 20: If you could write a letter to one person from this year—living or not—who would it be and what would you say?
December 21: What do you want the people closest to you to know about how you experienced this year?
Week 4: Looking Forward
December 22: What do you want to feel more of next year?
December 23: What do you want to feel less of?
December 24: What’s one thing you’re afraid to try next year? Why?
December 25: What would you do next year if you knew you couldn’t fail?
December 26: What’s one pattern from this year you refuse to repeat?
December 27: What skill or knowledge do you want to develop next year? Why does it matter?
December 28: What does your ideal ordinary Tuesday look like next year?
Week 5: Synthesis
December 29: In one paragraph, summarize your year. Then read it out loud.
December 30: What advice would December-you give to January-you?
December 31: Write one sentence that captures who you’re becoming. Let it be unfinished.
What to Do With 31 Entries
Here’s where most reflection challenges fail: they end on December 31st and you never look at what you wrote again.
You now have a dataset. Thirty-one snapshots of your inner life across a single month. If you just close the notebook, you’re leaving insight on the table.
Read back through your entries and look for:
- Recurring themes. What topics kept coming up, even when the prompts were different?
- Emotional patterns. Did certain days feel heavier than others? Why?
- Contradictions. Where did you say one thing and mean another?
- Silence. What did you avoid? What prompts did you skip or write the least for?
The patterns in your writing reveal the patterns in your life. Most people journal for years without seeing them.
Reflection That Actually Goes Somewhere
If you completed this challenge, you’ve done more intentional reflection than most people do in a decade. But what happens next?
At Reflekt, we built a journaling app that doesn’t just store your entries—it helps you understand them. Our analytics surface the patterns you’d never see on your own: mood trends over time, connections between what you write and how you feel, themes that keep emerging across months and years.
Your entries mean something. We help you see it.
Start the new year with a journal that journals back. Try Reflekt free →