As we head into the holiday season, we are approaching what for many of us is a time of deep contemplation and introspection. After this crazy year we’ve all had, it may be tempting to “check out” through the next several weeks as we await what will hopefully be a brighter, less-fraught 2021. But it would be a shame to end the year on a negative note, or to let 2020 slip by without acknowledging the lessons it has gifted us. 

To that end, these next several weeks will find me devoting significant time and mental space to intentional soul-searching, self-examination, and reflection. For those of you who are also feeling pensive these days, I’ve compiled a list of contemplative questions to guide us as we reflect on the year we’ve just had and make plans for the holiday season and beyond. 

There are no rules for these questions: embrace those that are valuable to you, and leave the rest. You can take them to your journal, discuss them with a partner or friend, or simply spend some time pondering your answers while sipping cocoa next to a cozy fire. The goal isn’t clearcut answers, but a general sense of clarity and uniformity of heart, mind, and soul as we close the chapter on one year and prepare ourselves for whatever lies ahead.

As we enter the Thanksgiving and Christmas Season . . .

1| How will your holidays look different this year? How do you feel about those differences?

2| Is there anything you can do to make the holidays seem more “normal”?

3| Embracing this year’s circumstances as a catalyst for change—are there any new traditions you might consider adopting, or old traditions you are happy to say goodbye to?

4| Are there any steps you can take to prepare your heart and mind for the holidays you hope to experience this year?

5| What is one practical thing you can do NOW to set yourself up for success this holiday season?

Reflecting on the year we’ve just had. . .

1| What did you learn this year—about yourself and the world around you?

2| What were your biggest disappointments or regrets of 2020? What were your biggest joys?

3| What were the biggest surprises of this year? What didn’t surprise you?

4| What were some of your favorite discoveries of 2020? (Purchased items, new recipes, television shows, podcasts, books, etc.)

5| What worked for you this year? What didn’t work?

6| Does your faith/spiritual life look different today than it did one year ago?

7| Where did you see God’s kindness and provision in 2020?

8| How have you grown or changed in the past twelve months?

9| What are some habits, attitudes, or beliefs you would like to leave behind as we enter the new year?

10| What single word or phrase best sums up your 2020?

Preparing for a fresh start in 2021 . . .

1| What new habits, atittudes, or beliefs did you adopt in 2020 that you hope to carry with you into the future?

2| Are there any relationships you would like to deepen in the coming year? Are there any relationships you need to say goodbye to?

3| Do you have a one-word theme for 2021?

4| What is one thing (or five, ten, or twenty-one things) you would like to accomplish in 2021?

5| What are you most anxious about in the coming year? What can you do to relieve that anxiety?

6| What is something you are looking forward to in 2021?

7| How can you serve others this year?

8| What steps do you need to take to care for yourself over the next few months?

9| What are your plans for growing mentally and spiritually this year?

10| What about your current life do you hope will look different one year from now?

As we prayerfully consider our answers to each of these questions, my hope for myself—and for you, too—is that this mindful posture towards 2020 may redeem the hardest parts of this year and set the stage for a new year marked by gratitude, intentionality, and hope.