Gearing up for an annual review

It’s that time of the year again. December is about to knock on the front door; before you know it, it’ll be January.

Over the past few years, I’ve come around to my friend Justin Weiss’s ( thinking on yearly quarters.

Q4 is a lie! It isn’t a quarter; it’s made of Holidays!

Once December starts knocking on the door, you’ve got ~two full weeks of work (in between Holiday planning) before the holidays arrive. And then it’s a new year.

Put another way, 2022 is going to be over dramatically soon. How did your 2022 go? What are you doing to think and reflect on 2022 and prepare for 2023?

My process for annual reviews

With December almost here, I’m starting to think about my 2022.

Each year, I set aside time at the end of the year to ask myself questions and reflect on the year as a whole. I’ve been doing an annual review of one form or another for the past ~ten years.

I do this process for both my business and personal life.

What I’ve found is that taking a few (non-concurrent) days at the end of the year and reflecting on how the year went helps me:

  • Better understand the shape of the year
  • Practice gratefulness for the ups and downs
  • Identify what I want to do differently next year

In the past, I’ve used and enjoyed Chris Guillebeau’s Annual Review questions. These days, I like to start with these short, sweet, and simple retrospective questions.

  • What went well?
  • What could have gone better?
  • What will I do differently next year?

My process is simple. I’ll:

  • Start a new document (in Notion, Text Edit, or Google Docs – any tool works)
  • Drop in those questions
  • Start free-form writing and responding to the questions

Then, after an hour or two, I’ll close the document and put it away for a few days to return later with a fresh mind.

If I end up needing some additional constraints, guidance, or questions for the writing or thinking, I’ll:

  • Review my quarterly plans for the year
  • Think about what happened each month
  • Use my Business Health Analysis questionnaire to spark new insights (The Business Health Analysis is the detailed questionnaire I use with all of my 1-on-1 growth coaching clients –

I’ll iterate on my annual review a few times until it feels like I’ve gotten all the relevant bits in there.

Then I’ll reflect on the year, think about what I want to get done (or do differently) next year, and capture those insights.

Would you like to talk one-on-one about your business’s 2022?

If you’d like to talk through your business’s 2022 and what you’d like to do differently to market, grow, and generate leads in 2023, I have a limited number of one-on-one calls available in December (

On a one-on-one call, we can:

  • Talk through your business’s 2022
  • Capture what went well + what could have gone better
  • Define a plan for what you want to do differently in 2023

All calls are optionally recorded. At the end of the call, you’ll get my notes, a recording (if desired), and the plan for what you want to do differently in 2023.

You can book a one-on-one call right here: