winter sunset

20 questions for a New Year’s Eve reflection

It’s time for our annual 20 Questions post! We pull it up here on the blog every New Year’s Eve, and I love hearing from you all how you use it. After tweaking and adjusting this list for the past five-ish years, we finally settled on a good master list of solid questions to help you reflect on the past twelve months.

As you end this new year and move on to the next, take a bit of time to review, to contemplate, to meditate. Post-eggnog, it’s easy to want to speed forward with gusto, pack up the ornaments until next year, and juice-cleanse your system from all the holiday indulgence.

But ease your foot onto the brake just for a few days, and gift yourself the space and freedom to reflect on the past year.

I’m all about starting a new year fresh, making a few goals, finding that one special word, or whatever helps you clean out the cobwebs from the corners. But all that stuff is much more meaningful when you look behind you at the bends in your road.

Honor the past year by celebrating your joys, mourning your losses, and shaking your head at the wonder of it all. Isn’t it amazing another year has passed? And so the earth goes round and round, about to orbit once more.

Whether you’re headed to a party or headed to the living room with a bowl of popcorn, New Year’s Eve is a great day for reflection. A whole year has passed since the last one. You’re a year older. Are you a year wiser?

Use these next 48 hours to reflect on the past 365 days.

20 questions for a New Years Eve reflection. Download and print to journal solo, discuss with your spouse, or chat with friends at a low-key gathering. It's an annual tradition for us!

20 questions for a New Year’s Eve reflection

1. What was the single best thing that happened this past year?

2. What was the single most challenging thing that happened?

3. What was an unexpected joy this past year?

4. What was an unexpected obstacle?

5. Pick three words to describe this past year.

6. Pick three words your spouse would use to describe your year—don’t ask them; guess based on how you think your spouse sees you. (If you’re not married, have fun guessing the answers from other friends and family, or just skip this question.)

7. Pick three words your spouse would use to describe their year—again, without asking.

8. What were the best books you read this year?

9. With whom were your most valuable relationships?

10. What was your biggest personal change from January to December of this past year?

11. In what way(s) did you grow emotionally?

12. In what way(s) did you grow spiritually?

13. In what way(s) did you grow physically?

14. In what way(s) did you grow in your relationships with others?

15. What was the most enjoyable part of your work (both professionally and at home)?

16. What was the most challenging part of your work (both professionally and at home)?

17. What was your single biggest time waster in your life this past year?

18. What was the best way you used your time this past year?

19. What was biggest thing you learned this past year?

20. Create a phrase or statement that describes this past year for you.

Download the 20 questions as a free PDF.

Want to answer these questions solo? Grab a cup of coffee and a pen, and use the space provided on the first three pages of the free download.

Want to chat over the answers with your spouse or with friends? Use the last page of the PDF to cut each question into squares, and then toss them in a hat to draw, one at a time.

And new last year—a set of questions for your kids! Pass it along to them for a personal reflection exercise, or you could cut up the questions, toss them in a jar, and pull them out to answer as a family.

Download the kids’ questions as a free PDF.

Tomorrow, I’ll share another round of annual questions that’ll help you think about the upcoming year. Have any dreams? Hopes? Goals so big they make you laugh? I hope so.

Cup of coffee

Also, what would you like to happen for you personally, for your children, for your family? I’m also currently giving away part of my Upstream Field Guide free right now—a simple guide to help you create a Purpose Statement for your family. This has been the key to helping my family narrow down who we are, what we’re about, and what matters most to us. It’s the most helpful tool in our arsenal to help us say no to the good-but-not-best, giving us more time and freedom to say YES to the best.

I’d love for you to have it. Head here to receive the download to help you create your Family Purpose Statement and get next year off to a great start.

For now, happy reflecting! And pass over that bowl of popcorn.

Tsh Oxenreider

Tsh is the founder of this blog and just finished traveling around the world with her husband and 3 kids. Her latest book is Notes From a Blue Bike, and believes a passport is one of the world's greatest textbooks.

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  1. Ah, a good reminder. I feel like I slam straight into achieving all my goals rather than stopping to just breathe and reflect.

  2. Great questions! And I love the addition of the kid’s questions. This has been an absolutely packed year of many changes for us so the reminder to stop and reflect is a much needed one.

  3. Important reminders, Tsh, to stop and reflect instead of barging ahead. I’ve printed these out and will bring them to a kid-friendly New Year’s Eve party. Thank you for putting this together in a beautiful and practical way!

  4. This is a tough list. It means I would actually have to sit down and think. 🙂

  5. Thanks for these reflection questions, Tsh. I will definitely use both the adult and kid questions (my son is 4.5) over the next couple of days just to give our family a time to talk about the year that is coming to an end. I will try to remember to come back to this conversation to share the results. Happy New Year! Caitlin

  6. Yesterday I printed your 2010 download, but now I printed the kids questions and CAN’T WAIT! for the 2014 hopes and dreams download. Thank you! it has become a great tradition.

  7. As I commented last night, I love your end of year & new year thought prompts! My husband, newly one year old son, and I are completing day 15 of a holiday road trip and we enjoyed going thru these together (though son slept!).

  8. Thank you for these questions! We have done them the past 2 years, and it’s always a positive experience. I think reflecting is important in order to learn and remember.

  9. I was hoping you would put this list up today! My hubby and I now have our date-night dinner conversation plan!
    I’m curious to see how the questions go for the kids… (two boys, ages 4 and 5.5)

  10. Wonderful reminder to reflect before racing into the year ahead. Thank you.

  11. What a great idea! We’ll be skipping the big party hupla tomorrow and spending a quiet evening in……think this is the perfect accompaniment to a fire and hot chocolate.

  12. I love these questions. It seems so easy to put the previous year into a good/bad box. This is a great chance to think about it, appreciate it, and think about the coming year, as well.

  13. Thanks so much for the post. It was a great way to think back on the year. I’m not a huge fan of New Year’s as a party day, but I like the idea of using it to plan for a better next year!

  14. I love your questions, Tsh. The last few Decembers I write up a quick summary of the year: blessings, lessons learned, but I haven’t taken time to do it this year, but this post from yesterday and today’s post are reminding me that January won’t be too late! I plan to use some of your questions over family dinner tonight.

  15. Tsh,
    Thank you for this–I do some reflecting, but this list goes above and beyond. I appreciate it!

  16. Thank you so much for posting this list again. I actually was thinking of this and hoping I could find last year’s post because I really enjoy and need this reflection. Thank you for reposting!

  17. Thank you so much for sharing this tradition. I’ve completed your worksheets the past three years and had an epiphany this time! For the last 3 years, the hardest thing I have experienced has also been the thing I was most grateful for. What a lovely reminder of the transformative power of difficult experiences.
    I wrote about it on my blog, if you are curious to read it:

  18. Really useful questions. Thank you.

  19. Hi again,
    So, I’ve asked my son a couple of the questions that you provided and got some really cute and memorable answers. I decided to buy a journal to record his responses each year. Hope I remember to do it each year! Also, I’ve used the questions for adults you provided this year and last and really appreciate how well it gets me to think of “the big picture” and starting DREAMING BIG! Thanks again Tsh!

  20. Hi there! This is a wonderful idea. I hope you don’t mind that I featured you in my blog. You are worthy of the recognition and the share. Thank you for the inspiration.

  21. Love this list! Thank you. And thank you for this blog, such an amazing source of encouragement. Happy New year to you all!

  22. Tsh, thank you so much for sharing these again.. I think I’d downloaded last year’s from here as well and both the New Year’s Eve and New Year’s ones are perfect for helping us plan a year of intentional growth and reflect on the past year with gratitude, for the good and the not-so-good:)

    Happy New Year to you and the family.. Excited to see what 2015 holds for AoS 🙂

  23. I Wonder if it sounds weird to say I’d like to become more intentional this year. Does that make sense? I spend so much time with things happening to me versus doing things. I can’t grow like this and I’m nowhere near performing to my potential. That I even speak of it is a little step forward. Thanks for facilitating that. Happiest of New Years to you.

  24. Thank you for providing pdf format of your good questions. I need time to reflect on 2014 and your ?s were exactly the guide I needed to get 2014 in perspective and now move on

  25. I so feel like wife in our relationship sometimes. I discovered your blog in August and it just spoke to me. I am constantly forwarding my wife your posts. This one is no exception. I am big on year end review. John Piper says each new year we get to practice death. I like thought, because on Jan 1, we are usually still alive and get to try again. Happy new year to you and your family.

  26. My partner and I did this together today. Made us think some for sure. Thanks!

  27. Kimberly Locke says:

    We’re bringing this to a family dinner tomorrow, and I’m adding the question, “If you could magically gain a skill or talent in 2016, what would you choose?”

    I would become a master knitter who can play the guitar. 🙂

  28. It is true that last night of the year will not come again. So we have to enjoy the day and remember til the next New year. Making New year revolution to make life more meaningful.

  29. its True Great questions. Thank you

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