20+ Questions For a New Year

I’ve dusted off and republished this list of 20 reflection questions for the end of a year for ten years now — almost as old as this blog itself. It’s quite fitting that it’s the penultimate post! Here it is again for you to use this year, and the next, and the next, and the next… And check back tomorrow for AoS’ final goodbye post. It’s been an incredible 12 years, and I’m glad for every minute of it. (p.s. I’m not going anywhere.)

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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 planning, goal-setting, and getting stoked about what lies ahead.

But ease your foot onto the brake for a day or two. Give yourself space and freedom to reflect on the past year.

I’m all for starting a fresh new year, dreaming up ideas, finding that one special word, or whatever helps you clean out the cobwebs in the corners. But all this is 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.

Whatever you’re doing to celebrate, 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 your last few hours of the year 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.

Download the 20 questions as a free PDF

👆 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.

Download the kids’ questions as a free PDF

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 still 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.

Note: It’s helpful for me to first review, reflect on, and make tweaks to my Rule of Life because it helps me remember what matters to me in the first place. There’s no point in setting goals I don’t actually need or want. (If you’ve never written your own unique Rule of Life, here you go.)

For these 90-day goals, I use 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:

Past:

What was the best thing about the past 90 days?
What was the biggest challenge?
How was life in the realms of work, relationships, money, health, community, and home?

Present:

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?

Future:

How would I like things to be 90 days from now in the realms of work, relationships, money, health, community, and home?
How could I create one or two goals* from these desires?
90 days from now, how will I recognize or celebrate my life as it stands?

*Only one or two because if we over-plan here, we hijack our good intentions with a performance-oriented posture about life — an exhausting way to live for anyone. But one or two goals, and goals for only the next 90 days, provides traction and motivation to make helpful changes, one doable step at a time. This brings us closer to who we want to be.

Every January I also like to re-read some combination of Atomic Habits, Essentialism, and The Simple Path to Wealth. These keep my head screwed on straight when I’m tempted to plan for All The Things at the start of a new year. (Also, here are my favorite books for clear-headedness.)

Enjoy your New Year celebrations, friends! Our usual modus operandi is living it up big-time in our living room with games, movies, and a midnight countdown for whoever’s still awake. You too?

XO, Tsh

p.s. If you’d like to keep up with my writing, podcasting, pilgrimage-leading, and other sundries in my work, make sure to get my free weekly email called 5 Quick Things, where I share five things from the week i either created or loved.