The End-Of-Year Reflection Ritual I Use to Get Ready for Planning

Stephanie Wasylyk
5 min readDec 13, 2022


Last night we finally got our first snow. My Christmas shopping is almost done, and this is the last blog post until the new year. This weekend we’ll put up our tree, and next week will be a short work-week. The family group text is filled with who is bringing what for the epic charcuterie board we have planned. All the pieces for a beautiful holiday season are falling into place. But of all the lovely things I will do over the next few weeks, I will honestly tell you with no word of a lie that my year-end reflection process is my favourite.

I know it sounds like I’m just saying that, but truly I mean it. Let me tell you how it goes.

Every New Year’s Day I make sure to find a few hours to myself. That used to be easier pre-kid, but it’s worth the effort to make it happen. I get out the notebook I specifically created for this (with my own artwork on it), I find my favourite pens, sit in a comfy spot, and get into it. Every year I debate whether to re-read past years first, or just get into writing. Usually my curiosity of the previous year wins, though.

My ritual isn’t fancy or complicated because I couldn’t sustain it if it was. Sometimes I get interrupted and have to go back to it. Last year and this year it was even easier since I had been tracking my accomplishments and celebrating all year (see my template for that in this post here).

The reflection itself is also quite simple. Over the years I have curated a list of questions and prompts I really like, so I just go through those, journalling the answers. I don’t feel pressure to write a lot or a little, I just go with what comes. Usually my hand starts to cramp, and then I just keep going, knowing the family will be back soon to break the silence.

Before I share the questions I use, let’s just give this a little context. Instead of me telling you why reflection is important, pause for a second and think about the answer for yourself.

What about reflecting feels important?

How does taking time to reflect inform your goals and plans for the coming year?

What barriers do you have for a reflection practice?

What would make it most impactful for you?

What might happen if you don’t take any time to reflect on the past?

And now, without worrying whether you’re getting this “right” or following what I do, let’s think about what a meaningful practice could look like for you.

What makes you feel the most calm and centred?

How do you like to process your thoughts? (written, spoken, something else…)

Do you want to do this alone or with others? Freestyle or in a facilitated space?

When would you like to reflect? Is the end of the year the right time, or some other time?

Would you like archives of previous years to look back on?

Are there certain parts of your life you feel most drawn to reflect on?

What could a meaningful reflection practice look like for you?

There is no right way to do this. There is no “reflection police” who will check on your work. You get to create this how you like, or not do it at all. But I’m assuming if you’re reading this you’re at least somewhat interested in some part of this!

I should also mention that I don’t really do a separate reflection process for my life and business. When I reflect I lump it all in together and process it all at the same time. That’s not to say I don’t look at finances and stats separately, but this is more of an intuitive/emotional process I do. For a more detailed reflection on my business I do an annual report which Laura Posey facilitates in Plan to Win.

Once you’ve truly given this practice some thought for yourself, you can have a look at the questions I use below. They originate from two places.

First, I go through a few of the questions I saved from Michael Hyatt’s course “Best Year Ever”. I took it years ago and from what I can tell it doesn’t exist anymore, but he turned it into a book. (It has stuff about goal setting too, but Laura Posey’s stuff about planning and goals is way better.)

The questions are:

· What movie genre would best describe the past year?

· What 2–3 themes kept recurring in your life last year?

· What accomplishments are you most proud of achieving last year?

· What do you feel you should have been acknowledged for but weren’t?

· What disappointments or regrets did you experience last year?

· What was missing from your life last year if you look back? Look at major areas of your life.

Then I just make note of other reflections or things I want to remember before moving on.

For a few years that’s all I did, but in 2020 I listened to a great interview with Courtney Martin on the Hurry Slowly podcast and she opened up a whole new list of questions for me. I won’t re-type them here, but you can find them all listed in this post here. They really go deep so be prepared for some pretty cool insights you might not otherwise get.

And that’s it! It really is that straightforward. Simple and easy, just the way I like it.

After this I go through the Plan to Win process I’ve mentioned before to get my business plan all ready for the coming year (usually on a different day), but this reflection process gets me fired up to do that.

What will you do? What do you already do? That’s the most important part. Enjoy!

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