20+ Questions For a New Year
It’s time for our annual 20 Questions! I re-release it here around every New Year’s Eve, and I love hearing how you all use it. After tweaking and adjusting this list for several years, I’ve finally settled on a good master list of solid questions to help you reflect on the previous twelve months.
As you end this new year and move on to the next, take some time to review, to contemplate, to meditate. Post-eggnog, it’s easy to speed forward with gusto and juice-cleanse your system from all the holiday indulgence. I’m a future-oriented thinker, so I love new year planning, goal-setting, and getting excited about the next twelve months.
But ease your foot onto the brake just for a day or two. Give yourself the space and freedom to reflect on the past year.
I’m all for starting a fresh new year, dreaming big, finding that one special word, or whatever helps you clean out the cobwebs in the corners. But all this is much more meaningful when you remember the bends in the road behind you.
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 New Year’s Eve
- What was the single best thing that happened this past year?
- What was the single most challenging thing that happened?
- What was an unexpected joy this past year?
- What was an unexpected obstacle?
- Pick three words to describe this past year.
- Pick three words your partner or close friend would use to describe your year.
- Pick three words your partner or close friend would use to describe their year.
- What were the best books you read this year?
- Who were your most valuable relationships with?
- What was your biggest personal change from January to December of this past year?
- In what way(s) did you grow emotionally?
- In what way(s) did you grow spiritually?
- In what way(s) did you grow physically?
- In what way(s) did you grow in your relationships with others?
- What was the most enjoyable part of your work (both professionally and at home)?
- What was the most challenging part of your work (both professionally and at home)?
- What was your single biggest time waster in your life this past year?
- What was the best way you used your time this past year?
- What was biggest thing you learned this past year?
- Create a phrase or statement that describes this past year for you.
Want to journal through these questions alone? Grab a cup of coffee and a pen, and use the space provided in the free download. Or, write your answers in your own journal (that’s what I do).
Want to chat over the answers with your family or friends? Use the last page of the download to cut each question into squares, then toss them in a jar to draw, one at a time.
Questions for Kids!
Do your kids want questions of their own? Pass this along to them for a personal reflection exercise, or cut up the questions, toss them in a jar, and pull them out to answer as a family.
And, for New Year’s Day…
For years, I used an annual planning guide I created to help me dream about the next 12 months — even though I’ve never been a big fan of the idea of “resolutions,” I still held on to the idea of setting a lofty goal to inspire confidence until the next December.
I don’t prescribe to that anymore. I just don’t find it useful. Instead of inspiring me, it’d make me feel trapped, daunted, or overwhelmed right at the start of a new year, when my insides felt hopeful and refreshed with a new beginning.
Now, I set 90-day goals. It’s a short enough amount of time for goals to feel (and actually be) do-able, which gives that boost I need to still care, keep heart, and course-correct for the following 90 days.
I set these in conjunction with what I call Think Days — little gifts I give to myself four times a year. They’re exactly how they sound: they’re days I set aside to do nothing but think. They’re magic.
Instead of a set of daunting annual questions to lead to daunting annual goals, this is simpler, sweeter, and more human. Here are the nine questions I use for my quarterly Think Days:
- What was the best thing about the past 90 days?
- What was the biggest challenge?
- How was life in the following realms: work, relationships, money, health, community, and home?
- What’s something, big or small, that brings pleasure in my life right now?
- What’s most valuable in my life right now?
- Is there anything that feels missing in my life right now?
- How would I like things to be 90 days from now in the following realms: work, relationships, money, health, community, and home?
- How can I make a SMARTER* goal out of 1-2 of these areas?
- 90 days from now, how will I recognize or celebrate my life as it stands?
*This stands for Specific, Measurable, Actionable, Risky, Time-Oriented, Exciting, and Relevant.
(Also, as an aside… my favorite book about all about is Atomic Habits, which flips the script on the idea of setting Big Hairy Goals for yourself. It’s really pretty mind-blowing in its simplicity and its effectiveness. I plan to make this an annual read for me, probably around this time of year.)
Enjoy your New Year celebrations, friends! We’ll be living it up big-time in our living room with games, movies, and a ball-drop countdown for whoever’s still awake. I’ll see you here in the new year!
p.s. Listen to the podcast episode about this post.
p.p.s. I’ve got a new podcast coming in early 2020, called The Good List. In it, I talk about the small, everyday things that make life better — you know, like stuff that’s in these questions you’ve come here for. If you’re into this sort of stuff, I think you’ll really like the podcast.
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