How I Do My End-of-Year Review

Most New Year’s resolutions fail, so I try to avoid setting hard resolutions.

Instead, I reflect on the past year and how I’d like to improve my life in the upcoming year.

I focus on two questions:

  1. How can I do more of the things I enjoyed most last year?
  2. How can I do less of the things that I enjoyed least, or got in the way of the things I enjoyed most?

I mix together personal and professional life because I view them as intertwined, but you may want to do them separately.

The first step is figuring out what things I enjoyed most and least.

What Did I Enjoy Most? Least?

This process is based on Tim Ferriss’s ‘Past Year Review’.

  1. Grab a piece of paper or notebook.
  2. Create two columns: Positive and Negative.
  3. Write down all the people, activities, commitments, trips, etc. that spurred the most consistent or powerful positive and negative emotions in their respective columns.

Places to find material:

  • Calendar: go through week-by-week and think about the emotions various entries trigger.
  • Memory: your strongest memories are good indicators of strong emotions, positive and negative.
  • Journal.

Questions to think about:

  • What were the most memorable moments of the year? Why?
  • What were the things I dreaded most this year?
  • What commitments did I really enjoy? What commitments did I dread?
  • What were the repeated activities that made me happy? Which did I hate being committed to?
  • What did my perfect days look like this year? Perfect weeks?

Once I’ve gone through this process, I have a page or two of bullet points about the highlights and lowlights of my year. Then I move on to the next step.

Healthy, Wealthy, Wise & Crazy

This is where I get creative and start thinking about potential goals and habits.

It’s a simple process: under each of those headings, brainstorm all the potential ideas you have related to that category.

They can be goals or habits, whatever you like.

These aren’t commitments, so feel free to put anything you’ve considered doing.

For me, Healthy consists of all the things that relate to my fitness, diet and overall physical health. 

Examples are things like:

  • Do a 3-day fast once per quarter.
  • Run a marathon.
  • Do pushups every day.

Wealthy consists of all the things related to my work and money. Often this could overlap with other categories, but don’t worry about that. Just brainstorm.


  • Get 1 consulting client outside my regular work.
  • Start a YouTube channel and produce 5 videos.
  • Write 1 blog post a month.

Wise consists of all the things related to learning and my mental health. Often there is overlap here with Healthy.


  • Journal daily.
  • Cook a 3-course meal for 6 friends every quarter.
  • Spend one weekend a month in nature.
  • Learn a new language.

Crazy answers the question: “What are the craziest things I could do this year?”. It’s a mental trick to help me think bigger, and get at some of my core desires (which seem “crazy” sometimes). 

The other question you can ask is: “What could I do to 10X ____?” Questions like:

  • What could I do to travel 10X more this year?
  • What could I do to 10X my income this year?
  • What could I do to be in 10X better shape?


  • Put all my stuff in storage and work remotely while traveling.
  • Create a video every day of the year.
  • Don’t purchase anything aside from food and essentials.
  • Quit my job and start Lambda School.

At the end of this, you should have bulleted lists of potential goals or habits you’re interested in for the upcoming year.

What Does My Perfect Day Look Like?

Just as it sounds, I write out what my perfect day looks like. I’ll often write out what the perfect workday and weekend day look like too. Being specific is important.

For all days, I think about questions like:

  • How does my morning start? What time do I wake up?
  • What things do I do first?
  • Where am I?
  • How much time do I spend on things?
  • What do I eat?
  • Who do I see and talk to?
  • How do I spend my day? My evening?
  • What does before bed look like?
  • What time do I go to bed? How much sleep do I get?

For workdays:

  • What do I work on?
  • What type of work am I doing?
  • What does my schedule look like?
  • How do I know if I’m succeeding?

I often expand and add things that make the perfect week or month too.

What Does My Life Look Like in 5 Years?

This is similar to the perfect day exercise, except I describe my life five years in the future.

The same questions apply:

  • Where am I?
  • What am I doing?
  • Who am I spending my time with?
  • What kind of place do I live in?
  • How do I spend my time?

The more specific, the better.

This exercise helps me think about my long-term goals. 

Doing it year after year lets me see how my priorities shift, and it helps me think about where I need to invest my time.

Time to Choose

At this point, it’s time to revisit the original questions:

  1. How can I do more of the things I enjoyed most last year?
  2. How can I do less of the things that I enjoyed least, or got in the way of the things I enjoyed most?

After the exercises above, I have a much better idea of what things I enjoyed most and least, and where I would like to invest my time.

Now I can set goals, plan habits, and think about strategies for reaching those goals.

These should be based on the answers to the following:

  1. How can I reduce friction for the things I want to do more of?
  2. How can I increase friction for the things I want to do less of?

In the next post, we’ll get into detail about how to form successful habits for reaching your goals.

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