Fewer resolutions, more goals

New Year’s and personal planning

For years, when December 30 or 31 rolled around, I would set a couple of resolutions to guide me in the New Year — “listen more”, “be less self-conscious,” and other well-intentioned but vague formulations. I often forgot about them after the month of January.

I believe that many people feel the same way about resolutions, which may be why many people stop setting them at all, or at least treat them with cynicism.

Although my approach to New Year’s resolutions wasn’t working for me, I have always liked the idea of using the period leading up to New Year’s as a time to reflect and set my sights on the year ahead.

In the past couple of years, I have replaced the haphazard resolution-setting process with a more through approach to personal goal setting. This approach is more integrated with the rest of my life than my resolution-setting ever was. It requires a lot more work and thought. But it has also helped enrich my life much more than any resolution ever has.

In this post I will share the current iteration of my personal planning process. The process has evolved each year over the past three years, and I expect it will continue to do so as I find ways to improve it and discover parts about it that aren’t working. I am sharing this because (1) others might find it useful (2) I’m hoping that talking about it publicly will make me more likely to follow through (3) I hope it might prompt others to share their personal planning strategies / tools so that I and others can learn from them. I don’t go so far as to share my actual goals here, as many of them are personal and, for better or worse, I am not yet ready for that level of transparency.

The process I use may or may not work for you, but I hope it will get you thinking about ways to improve your own personal planning and therefore enrich your life.

The process below took me about 10–15 hours this past year, which I completed during this past holiday break. However, some of the elements to the process (e.g., daily journaling, keeping a reading list of books with notes) are considerably more labour-intensive, and require commitment in the year leading up to the holiday.

The goal setting I describe here includes relatively little about professional goals. In my case, that is because the vast majority of my professional life is consumed by the company I co-founded, Common Wealth. At Common Wealth, we have our own fairly intensive approach to setting annual goals, informed by the “OKR” (Objectives and Key Results) approach that Andy Grove pioneered at Intel. Most of my professional goals are subsumed within Common Wealth’s goals.

Step 1: year in review

The first step in my process is to reflect on the past year. I do this by:

• Re-reading my journal entries from throughout the year. I write in a journal most days, usually in the morning. Some of my entries are relatively structured (e.g., lists of questions, lists of recent mistakes (inspired by Ben Franklin’s “Errata”), things I am grateful for, things I am anxious about, things that went well or didn’t go well in the past 24 hours). Others are free-form reflections and observations of varying degrees of quality. Re-reading these entries reminds me of insights I had, gives me a sense of where I was spending my mental and emotional energy throughout the year, and provides lessons on the process of journal writing and self-reflection itself (e.g., this year’s review helped me realize that “post-game” analyses of how a day went often yield more insight than “pre-game” analyses, leading me to want to shift more of my journal writing to the evening).
• Reviewing my calendar from the year. I go week by week, giving me a much more accurate picture of how I spent my time than if I try and go from memory. As I review the calendar, I try and think about the things I spent my time on that gave me the most positive feelings, and the things that gave me the most negative feelings. I borrowed this technique from Tim Ferriss.
• Reviewing my goals for the previous year and evaluating my progress against those goals. For me, this also involves reviewing the process by which I set those goals and thinking critically about it.

Some of the questions I ask myself, and take notes on, during the year in review, include:

• Are there worthwhile goals / ideas I had that I haven’t yet executed on that I should prioritize for the coming year?
• What were the main “successes” or positive things about the year? What were the main things that didn’t go well or that resulted in negative feelings?
• What are the areas in my life where I am on auto-pilot and am not really living consciously? How can I be more deliberate about these areas?
• What routines or experiences have made the biggest difference in enriching my life over the past year? Why?
• Am I spending my time and mental / emotional energy on the priorities that are most aligned with my values? If not, why not?

Step 2: develop a process for goal-setting

I prefer to be very conscious about the process I use to set my personal goals, varying it from one year to the next on the basis of what seems to be working. This year, based on my review of 2017, I decided the following:

1. I would break my goals into five themes related to my values and priorities: relationships, learning, health, giving/service, and finances.
2. I would focus on three ways to advance each of these themes: (i) results / objectives (ii) routines (iii) experiences / experiments.
3. I would develop the following tools to supplement my annual goals: (i) a revised weekly routine (ii) a reading list (iii) a list of things to do on the weekends.

Step 3: set goals

This step involves filling out a table that looks like the one in the image below:

Personal goals table 2018

• Results / objectives are outcomes you want to achieve (e.g., average 12,000 steps a day of physical activity, donate $X to charity, read 40 books and document the results). This is a powerful way to set goals, and is informed by the OKR approach and other outcomes-based thinking from the business world. The limitation I have found with this approach, especially in the realm of personal planning, is that the goal or result does not tell you what to do in your day-to-day life to achieve it. That’s where routines and experiences / experiments come in.
• Routines are things you will commit to do on a regular (i.e., usually at least once a week) basis (e.g., meditate 4x per week, stretch for 10 minutes 5x per week, have a weekly date night with my partner). The nice thing about routines is that, ideally, you don’t have to think about them one they have been designed and you have gotten in the habit of following them. Routines might be the most powerful way to achieve personal goals. I have found that they become even more powerful the more specific you get in designing the routine. For example, “mediate 4x per week” is much less powerful than “do 15 mins of meditation on Mon, Tue, Thu, and Fri, from ~6:45 am after writing in a journal and before eating breakfast.”
• Experiences / experiments are things I want to try once or no more than a handful of times during the year. They are more periodic than routines, and therefore, for me, must be scheduled in advance or they don’t tend to happen. An example of an experience is a father-son canoe trip I want to take with my eleven-year-old this coming summer. An example of an experiment is a gathering I want to convene on personal finance with a group of friends — a follow-on to another related experiment I tried this past year.

Step 4: develop supplementary tools

Once I filled out the table, there were a few other tools I went on to develop. These remain works in progress and I will continue to evolve them throughout the year:

• Weekly routine: This involves designing a template weekly schedule that builds in the “routine” items listed in the matrix above. In my case, this year’s routine is similar to the one I used last year, but with some minor adjustments. It includes elements like regular journal writing, exercise, and weekly planning sessions on Sunday evening. The focus of these routines, for me, is what I do first thing in the morning, before the rest of my family wakes up, and what I do in the evening once they have gone to bed. These are the times over which I have the most control.
• Reading list: One thing that has really enriched my quality of life over the past few years is increasing both the volume and deliberateness of my reading. I love to learn, but until recently I found myself reading relatively little and fairly randomly. Every time I would finish a book, I would have to think about my next book, and would often end up picking the first thing that crossed my desk without really thinking about it. Creating a reading list based on learning goals (some of mine this year relate to software, management, community building, and Indigenous perspectives) and recommendations from friends and other people you admire is a great way to be more deliberate about what you read and what you learn. Perhaps I will share my reading list in a future post once it is in better shape. Another game-changer for me has been audiobooks, which I listen to during commutes to and from work and while doing chores like laundry and preparing school lunches. I have also started to take notes on the books that I read, inspired by Farnam Street’s excellent blog posts, and Mortimer Adler and Charles Van Doren’s classic book, on becoming a more active reader. My goal this year is to take a least of page of notes on each book I read, so I have a catalogue of the main things I took away from each thing I read.
• Weekend list: I realized this last year that I was paying too little attention to my weekends. This was a stark contrast to my work week which I would carefully plan each Sunday evening. A got a wake-up call after reading fellow Torontonian Katrina Onstad’s The Weekend Effect, whose description of busy city dwellers sleepwalking through their Saturdays and Sundays hit close to home, helping me realize that my family and personal life was suffering due to my lack of attention. Onstad’s book is a compelling call to action to pay more attention to our precious weekends. In my case, I’m going to try to be more conscious about weekends by making a list of things to do on weekends throughout the year and planning things out in advance, while leaving an element of spontaneity that my family and I love about weekends.

Gaps / continuous improvement

I’m excited to get started on my 2018 goals and new processes. I can already sense that there are a few things that will need to be improved or tweaked:

• I probably have too many goals
• The goals could be more tightly connected to a higher-level, longer-term statement of purpose, similar to the one Clayton Christensen talks about in his excellent book How Will You Measure Your Life?
• I still haven’t figured out a reliable system for holding myself accountable to the goals I set at the beginning of the year

This is part of the fun and challenge of personal goal-setting — it forces you to be more conscious about how you live your life, and you learn a great deal in the process.