4 ways to do a year reflection

December 23, 2021

The year’s end is an opportunity to zoom out from the daily chaos and see the bigger picture of where your life is going.

• What worked well for you this year?
• What surprised you?
• What do you want more or less of in your life?

Learn about yourself

I’m doing a reflection every year. I like to mentally close whatever I fucked up last year and move on towards the sweet sweet failures awaiting me in the next one.

Take an hour or two to reflect on your year. It is worth your time and energy to learn about yourself. That’s the engine correcting the course of your life.

But maybe you’re not into analyzing events and decisions. That’s okay. I’ve included some easy and fun ones for you.

These are the four ways of doing a yearly reflection. I gave them personalities based on their style. Feel free to jump to the one that speaks to you:

1. Detective
2. Artist
3. Improviser
4. Navigator

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Detective

Collect evidence to make a conclusion.

Let’s investigate. If you use a calendar, journals, or notebooks, go through them chronologically and list everything significant from last year.

Write down anything that feels important: events, changes, big decisions (or small decisions that turned out to have a significant impact).

You will remember things you don’t have in your notes as you go through them. Write them down too. You’re collecting evidence of what happened.

After going through this, the mental image of your last year will be as sharp as it can be. You will use that to answer questions.

How to do this step by step:

1. Go through your calendar from January to December day by day, and write down everything significant.
2. If you have a journal or other notes, use them too.
3. Once you’ve made a list of everything that happened, answer these questions:

• Good stuff: What worked well? What made you happy? What did you do right?
• Not as good stuff: What didn’t work? What made you unhappy? What did you do wrong?
• What surprised you?
• What/who influenced you the most?
• What did you learn?
• What do you want more of in your life next year?
• What do you want less of in your life next year?
• What are you going to do to make these changes happen?

Artist

Visualize the essential things.

This is a fun one. If you’re not into analyzing things, I offer you a more ‘creative’ approach I enjoy using.

For three years in a row, I drew my year like this:

“Drew” is a strong word. It’s more like a word cloud or a mind map with tiny images here and there.

You can go nuts and be much more creative with picturing your year.

How to do this step by step:

• Get a big piece of paper (A3 works fine)
• Think about your last year: “What are the important things from last year?”
• Start drawing/writing whatever comes to mind
• Stop when you’re done or bored

*Secret: I was lying to you. I never used this approach for reflection. I always did it as an aspiration. I drew what I want my next year to be like.

You can choose whatever you prefer. Or do both.

A cool thing about drawing your future year is that you can then hang it on your wall to remind you what’s important. I always did that.

Improviser

Keep it simple. Just think out loud.

Maybe you see some value in reflection, but the idea of browsing through your calendar makes you a little sick, and drawing isn’t your thing.

Then I have a zero overthinking option for you.

How to do this step by step:

• Pick a pen and a random piece of paper. A napkin is a fun one. Toilet paper works too. I don’t judge.
• Ask: “So what happened last year?”
• Start writing whatever first comes to mind and see where it takes you.
• Stop when you don’t have anything else to say. It doesn’t need an end.

This method is spontaneous and doesn’t have to take long. And, at least for me, there is always value in writing down my thoughts, even if it’s just the equivalent of taking out the trash.

You could also do this as a conversation with someone. Or on your own, if you like walking in a circle talking out loud to yourself like I do.

Navigator

Review previous paths and adjust the course ahead.

Now it’s getting heavy. I call this ‘navigator’ mainly because it sounds fancy, and I wanted to keep the naming convention. But I haven’t done this method yet.

I’m going to try this one over Christmas.

It’s called YearCompass, and it’s a pre-made template of questions and exercises which will coach you through a deep reflection on your last year and planning for the next.

I’m giving this a try because more than one friend recommended it, and I’m in the mood for something heavy this year.

There is no need to tell you how to do it because the template will do a better job: Download the PDF, print it, and follow the instructions.

I expect this reflection to take me at least 4 hours. And I want to do it in one stretch because the mindset you get after right after reflecting for hours is difficult to replicate later.

So the real challenge here is blocking out enough uninterrupted time to do it properly.

Share your reflection with someone

It’s fun and useful to share the highlights of your reflection with someone in your life. (Only the parts you want to share, not everything.)

I’m planning to share it with my girlfriend. We will do the YearCompass separately and then talk about it later.

I just need to find some way to bribe her into filling the 20-page PDF.

Sharing your insights with someone is another way to learn about yourself. Because hearing yourself say out loud what matters to you is different than writing it. So give that a try.

Find a buddy and suggest that both of you do the reflection and then talk about it. Eat some cookies and have fun.