TL;DR: This article gives an overview of the reflection and planning ritual I go over at the end of each year. I have been doing this in different forms for a few years now and find it a rather great way to "recalibrate my north star" and with that shape a better and more concrete plans for the upcoming year. I do this in two main steps: 1) "look back" and reflect on the year ending (look at what happened, what I learned, what worked and not worked, etc.); 2) "look forward" - based on all insights and learnings from 1), I visualize and describe the key "aspirations" I want to invest/develop/prioritize in the upcoming year. The last step making sure I translate the aspirations defined in 2) into actionable things in my system for execution (i.e.: set clear outcomes and projects & habits for the upcoming year, which enable me to move forward towards my aspirations. I review and recalibrate these often on my month and quarter reviews). People tend to overlook this very last element, which in my view is a recipe for staying in "dreamland" and never actually moving towards that.

Notes: the elements shared in this article can be used to guide end-of-the-year reflections in any shape and form. I use and recommend implementing this in a system such as PPV, by August Bradley. The reason is that it has the notion of “Year” where we can systematically include this Year Review & Planning. Furthermore, this system enables connecting this exercise to all relevant elements of the “Life Operating System” PPV offers to this (including Projects and other things to get the “aspirations” in motion, but also the regular reviews and elements that enable us to keep things meaningful and on track). Find my quick overview of PPV in this article.

End of Year Recalibration

End-of-year review (and planning of upcoming year) can be a very powerful ritual to zoom out from the busy day-to-day routines and reflect on the year ending. This “recalibration” ritual enables us to learn from the many things we did over the past year and whether those are helping us move forward or not (also “what moving forward” actually means - in my view that is too continuously changing and evolving). This reflection provides a great framing to visualize and shape how to approach the upcoming year.

I have been doing this exercise for a few years now and it gives me a lot of energy to close the year ending by looking at all things I learned (good and bad) over the past year. This reflection also enables planning the upcoming year with a clearer framing of what are the important things one wants to focus on. That enables shaping more specific actions for execution and moving forward towards one’s aspirations. I think this last part is key: people tend to reflect and dream (which is nice), however, it is key to define clear and tangible outcomes and projects to move towards those aspirations.

Review & Planning

The figure below provides a high-level overview of my ritual. In the following sections, I provide some details on the two main parts of this ritual: 1) Year Ending Review; 2) Upcoming Year Planning, and the multiple steps in each part (which I highly advise following in the sequence described so that you incrementally build up the reflection).

Notes: I will share some snippets of my own “template” as I describe the different steps. I normally do my “Year Ending Review” at the end of the year, and then create a new Year entry on my system, where I fill in the “Upcoming Year Planning” parts.

End of Year Ritual

1: Year Ending Review

1.1: Review numbers and insights

The very first thing I do when starting my Year Ending Review is to go over the things I did over the past year. This can be many different things, for example:

  • objectives set in the previous year (and target outcomes. I tend to look at those on the three major pillars of my life: 1) Work & Career; 2) Home & Family; 3) Personal & Growth);
  • projects I worked on (and outcomes);
  • things I learned (try to list all things here);
  • reviews & statistics (e.g.: if you do weekly reviews and track your “week score” you can look at them. The same for monthly and quarterly reviews. It is interesting to look at summaries and “refresh” your mind with those elements);
  • etc.

This is a screenshot of the types of things I look into in this step.

Review Numbers and Insights

💡The goal here is: refresh your mind with important things that happened over the past year and how did it go in general. I also like to get some numbers down, e.g.: how many articles did I publish on my blog; how were my “week scores”, etc.). I do write some notes and “insights” per each element I look into (it becomes a sort of documentation - but also helps me to further set those ideas in my mind, which I find important to better approach the next steps of the ritual).

1.2: Perform End-of-Year Reflection

After reviewing the numbers and insights of the past year, we have a much fresher and clear mindset to approach the next step of the ritual: perform the actual End-of-Year reflection.

I do this by answering several questions that enable me to have a deep reflection on the year that is ending. This is my current template (highly influenced by questions from several people).

End of Year Reflection

This is a rather long list of questions. Some may not make much sense for some people. However, I think (and noticed) they provide a great framing for a deep reflection. Don’t overthink your answers, go with the things that come to your mind when answering these questions (they will most likely reflect the insights and mindset shaped in the previous step).

💡The goal here is: reflect on things we are grateful for in the year ending; accomplishments and challenges; things that made us happy and sad; things that we got excited about; things that brought happiness and joy; things we learned; and finally what has helped us to grow the most. Doing this should enable a deeper reflection on the year that is ending.

2: Upcoming Year Planning

2.1: Framing Reflection

In 1.2 we did a review of the previous year, which allows us to make clear what were the most important things happening in the year that is ending. This puts us at a great starting point to approach the upcoming year planning.

I use the word “planning” with the intuit of “reflecting and shaping”. Namely: reflect and shape the direction on important topics and things I want to focus on in the upcoming year. This is not a “rigid” or step-by-step plan. This plan should (and will) be changed and improved as we move forward, do things and learn. We will be “re-adjusting” this plan regularly. However, it is key that we explicitly think about it using all sorts of learnings and insights to make it as clear and actionable as we can.

The first step on this is what I call “New Year Framing Reflection”. Below you can find the questions I use to approach this step.

Upcoming Year Framing Reflection

💡The goal here is: reflect on very important elements in one’s life, namely: people with whom I worked and spend time; things I care about; who I want to become; things I can improve on; things I regret doing; and what I learned from last year. These are great framing questions to go over to start “designing” the upcoming year.

2.2: Upcoming Year Design

This step focuses on “designing the upcoming year” (from all the framing done in the previous sections).

It should take some hours to complete. It is key that we don’t rush, as this is my view is the most important step of the whole ritual, as it consolidates all things into explicit aspirations that provide us with clear direction on how to move forward. The exercise here is really about re-assessing and adjusting aspirations for the upcoming year. That should enable shaping concrete and measurable outcomes to drive actionable projects to move towards those aspirations.

These are the questions I ask myself in this step.

Upcoming Year Design

As you can see the questions sort of build on each other, so it is important to answer them sequentially. Again, do not overthink, answer the questions with the things that are in your mind. They tend to be the most “important things”, and in general will be the outcome of the reflections on the previous steps.

💡The goal here is: look forward, visualize and describe important things to consider on the different important pillars. By going through these questions one starts visualizing the things that really matter and should be considered and worked/developed in the upcoming year. This step culminates in the questions: “describe what my life will be like in 12 months”. In this question, we can describe as clearly as possible those “aspirations”, including defining accomplishments (outcomes) we should have achieved if things go according to plan.

2.3: Set System Implementation

The very final step of this ritual focuses on translating the reflections and aspirations of the previous step (especially the “description of my life in 12 months”) into tangible and actionable outcomes that we can use to drive concrete projects and habits in the upcoming year.

As part of this exercise, make sure those elements are made explicit on your “system for execution”. This can be whatever tool and method you use (digital or analog). The important thing is to make sure it is not just an “aspiration”, but it becomes actionable to enable actual progress. Find below an overview of the sort of things I to over on my own system (I share some details and link to the template in the next section).

System Implementation

On my system I go over the following main parts:

  • Start by updating the more “long term aspirational” elements: such as my “North Star” - which describes my long-term ambitions for all my key pillars. This is rather aspirational and longer-term, and I do not limit myself with “how” and “when” questions;
  • Then I go into shaping aspirations I will focus on this upcoming year: these are the “Value Goals” - similar to “Objective” in the “Objective and Key Results” (OKR) framework. They describe things that enable me to move towards that “North Star”. They are rather aspirational, and one should not be bothered on being extremely tangible, e.g.: “Become very active in the DevOps Community”;
  • After that set “measurable outcomes” to move towards aspirations set for the upcoming year: these are the “Goal Outcomes” - which are sort of the “Key Results” part in the OKRs framework. Example: “Write 1 original article each month on DevOps innovations”. Here, be very concrete and tangible. These should be measurable and contribute to a Value Goal.
  • Finally set the projects and habits to enable progress: here we set very concrete projects and/or habits to accomplish the “measurable outcomes” set in the previous point. Example: “Write Product and Tech Collaboration Patterns article”). Every project and habit should contribute to a Goal Outcome. This is key to making sure we are spending our efforts on the things we deem important.

💡The goal here is: to make sure we translate the aspirational framing into very actionable things. That should trigger execution (and learning) on the things we deem as important. We do not want to make this a “day-by-day planning” for the whole year (that never works). However, we do want to set things in motion for the coming days, weeks, and possibly months with projects (and/or habits) that enable us to move forward. As we progress in the year, we should revisit these elements and adjust them (especially “Goal Outcomes” and “Projects”). An effective way to do this is to have regular review moments (e.g.: Weekly, Monthly and Quarter reviews - where one can revisit these elements and with all the learnings one has, update them to enable better execution).

Final Remarks

Some final remarks to consider when performing and implementing this ritual:

  • Approach this ritual with the flow/sequence described in the article. The different sections build on each other, and as such doing the different reflections with the suggested flow should lead to good outcomes.
  • You can find the complete template I refer to in the previous section here: End of Year Review Template - Notion or End of Year Review Template - Google Docs. The Notion template is part of my Life Operating System (Life OS) setup. My Life OS implementation is highly inspired by the PPV Life OS method developed by August Bradley (who has also shared his template and instructions for his end-of-year ritual here). I have experimented with many different methods and tools over the years and found that PPV is the one that fits my needs the best. It is comprehensive and provides a lot of elements that bring clarity on what we should be moving towards (makes that explicit), and then elements that enable sharp focus on execution to forward “day by day”. However, I think the template - its flow and questions - can be equally useful in any other setup (e.g.: simply doing the reflection on the year ending and visualization and planning of upcoming year, including clear projects to work on).
  • One last time: make sure that you do not stop on the visualization and aspirations. It is key that you define clear and actionable things to execute and move forward. To make this effective, do regular reviews and “re-calibrations” (we are always learning and with more insights can better prioritize where to spend our time).
  • Credits to the many people that influenced this flow and template, namely: August Bradley, Patrick Kua, Marie Poulin, among many others.