17 End-of-Year Reflection Questions (inspired by the Wizard of Oz)

Ready to set aside time for some end-of-year reflection questions?

Whew, what a year, right? Certainly one for the books, and I think, one worth exploring with some fresh writing prompts. (Of course, I totally understand if you just want to close this particular book and move on.) But before you do, consider for a minute that there’s actually evidence to support taking time for end-of-year reflection questions, and looking back as a path to both healing and increased well-being.

The trick is to do it in a way that focuses on meaning-making, self-identity, and self-compassion. Which, by the way, is exactly what these reflective questions are all about.

Even better: these end-of-year reflection questions are inspired by the Wizard of Oz.

Do you remember the Wizard of Oz? The original movie has been around a long time and never really lost its popularity. Before the days of streaming it was broadcast once a year on network or cable TV.

When I was growing up it was an annual event, and it was huge for me. I’d park myself on the floor in front of the TV with wild anticipation. And my heart leapt each time that crazy tornado thrust Dorothy into Oz, a land both beautiful and terrifying, from which she thought she’d never find her way back home.

By the end of the movie the little girl me was flushed with cathartic tears, as Dorothy said good-bye to her companions and finally made her way home.

Dorothy’s story is a classic quest story and transition myth. I like to think of it as a good frame for our own particular journeys through the years and decades of our lives.

So with a grateful nod to those who have done deep and important psychological research on this topic (like Carol Pearson and Joseph Campbell), away we go.

Your journey starts in your familiar world, in the comfort and safety of home.

But in every quest story there’s a call that tugs you away from home.

In real life we experience this both literally and psychologically. It might be a yearning toward something you can only name in a metaphorical, symbolic fashion (like Somewhere Over the Rainbow). Still, you know (perhaps subconsciously) that something needs to be changed. Something’s not quite right, maybe within yourself.

In myths and fairytales there may be a pending disaster that precedes the call and tells you all is not right with the world, like the drought and tornado in the Wizard of Oz.

And so, like Dorothy’s swift crossing from Kansas into Oz, each year pulls us from the familiar into the unknown in some way.

It might seem both scary and exciting. And even though you may not know exactly what’s pulling you, you feel captured by it.

Dorothy’s longing is all about her heart’s desire, and in its most elemental form, we’re in the land of the life force here: desire, fascination, passion, curiosity. Along with big doses of overwhelm and uncertainty.

End-of-year reflection questions to help you explore your yearnings during the past year:

• During the past year I yearned deeply for…
• During the past year I most desired…
• During the past year I was overwhelmed when…

Then suddenly, you’re not in Kansas anymore.

The thing is, to follow any call, inner or outer, mythical or real life, you have to enter the realm of wisdom. It’s pretty different here: mysterious, confusing, scary and anxiety-provoking.

There may be deep forests, dark caves, magical people, mystical creatures. And forces of good and evil.

But along the way you discover companions and helpers that provide support on the journey, because you simply can’t do it alone.

You find the strength to persevere in this strange mysterious place by partnering with others, just like Dorothy hooked up with the Scarecrow, Cowardly Lion and Tin Man.

End-of-year reflection questions to help you identify your helpers during the past year:

• During the past year I was supported by…
• During the past year I persevered when…
• During the past year I felt hopeful and resilient when…

At this point, things get really hard.

Almost every journey takes a turn at some point. Although things may look encouraging at first, they often don’t work out exactly as you planned. You’re thwarted by situations you can’t control. And just like in quest stories, you’re blocked along the way by mythic archetypes, both internal and external.

In Oz, Dorothy encountered a very bad witch. Trees that didn’t like her. And evil flying monkeys.

She was almost put to death in a field of poppies.

And she risked life and limb to get a broom to help her get home, only to discover that the wizard who could help her wasn’t really a wizard at all.

End-of-year reflection questions to help you explore your challenges and disappointments this past year:

• During the past year I was thwarted by…
• During the past year I was tested by…
• During the past year I was disappointed by…

Who knew you’d have a bottom of the barrel experience, where the only way out is up.

You’ve reached your Dark Night of the Soul, where things go from bad to worse to the absolute worst. At this point hope is in short supply. Well, okay, hope has pretty much deserted you.

The wizard flies off in the balloon without her, and Dorothy feels abject grief at the prospect of never getting home again.

And then, a miracle happens. You experience the universal paradox of quest stories (and often life): that in the act of giving up hope and releasing everything, hope suddenly reappears.

In Oz, Dorothy discovered that all she had to do was click her heels three times to go home, and she had the power right from the beginning. She finally recognized what was in her all along.

So renewal and rebirth are on the horizon. Personally, you discover an inner well of power, resourcefulness and resilience. You suddenly understand that it was there within you, but like Dorothy, you weren’t able to see it until now.

End-of-year reflection questions to help you explore how you reclaimed hope this past year:

• During the past year I felt hopeless when…
• During the past year I felt renewed when…
• During the past year I reclaimed my hope, resourcefulness and inner strength by…

Finally, you discover you can go home again. But you’ve changed.

As you make your way toward home, you move through the threshold passage reflecting on all you’ve been through.

You recognize that you’re carrying a lot back with you, and transformation always comes with both rewards and battle scars. Or gifts and wounds, if you will.

And sometimes the gifts are buried in the wounds.

But like Dorothy, you discover you can finally, always, come home to yourself.

End-of-year reflection questions to help you claim your rewards and gifts from past year:

• The rewards and gifts I’m taking from this past year into the next are…
• The wounds and battle scars I’m taking from this past year into the next are…
• The gifts of my wounds are…

Now it’s time to bring on the celebration. And gather a little wisdom for the coming years.

You made it! You’re back home again, like Dorothy, surrounded by whom and what you love. There’s happiness and rejoicing, as well as the sober realization that it’s been a difficult journey at times.

Looking back, though, you’re grateful to have gained a bit of wisdom that will serve you well in future years.

End of year reflection questions to help you claim your wisdom from this past year:

• If could go back and visit with myself a year ago, the wisdom I would most want to share with me is…
• As I cross the threshold passage into the next year, the wisdom I most want to carry with me is…

I don’t know about you, but after writing this I can’t wait to watch the movie again.

And after this past year, I’m so ready to bathe myself in some of those cathartic tears this story provides, as I write the quest journey of my own mythic year.

If I ever go looking for my heart’s desire again, I won’t look any further than my own back yard. Because if it isn’t there, I never really lost it to begin with.

-L. Frank Baum, The Wonderful Wizard of Oz