Hello my new and long-time subscribers,
The Substack community has expressed such exuberant interest in my recent article on creating a habit tracker in Obsidian that it took me by surprise. A common question I received from readers was “Why do I abandon tracking my habits after a while?” I assume that the question behind this question here is not tracking, but habit formation.
Therefore, in today’ newsletter, I discuss why habit tracking fails, the nature of habit, and how to plan your self-tracking projects. I also experiment writing this blog in English from time to time, please let me know what you think about this. I will share more about the motivation behind this decision in my upcoming posts.
Enjoy!
I. Why habit tracking fails
One of the most common misconception about habit tracking is that it either fails you or transforms you for good. This oversimplistic view is partly due to the rise of self-tracking technologies and the creator economy that paint a rosy picture of your perfect future self - if only you use their apps, consume their content, or buy their products.
This commonly held belief can result in adverse psychological effects, including:
Unrealistic expectations: When you track your habits for a certain number of days, you want to be able to tell yourself that “I’ve got it. Now I {desired behavior} every day!”. But as the old saying goes, life happens when you’re busy planning, so does your tracking project. When life kicks in, you revert back to inconsistency and become too discouraged to track again.
Tool dependence: While proper tools and gadgets can be critical in a successful self-tracking project, it can not replace self-reflection and deliberate planning. Neglecting these qualitative factors can result in not using tools effectively to reach your desired outcomes.
Shiny Toy Syndrome: When you fail to use self-awareness skills to motivate yourself along the nuts and bolts of your behavior change journey, you might fall into the trap of changing apps constantly in search for a perfect solution to your self-control problems.
Over-justification effect: Recently, a student in my lifestyle change class shared that he used to enjoy his morning jog until he signed up for a lifestyle program that asked him to track his exercise with a mobile app. He started tracking his daily physical activities, and this became a source of stress. Exercise (and tracking) became something he had to do instead of willing to do out of pure joy. This exemplifies the over-justification effect, where intrinsic motivation is undermined because an external incentive is introduced.
One of the biggest reason why tracking fails is because we do not treat them as a personal project that requires deliberate planning. What we often do is simply find an app and start tracking.
Habit-tracking does not make or break your habit. If habit-tracking does not work for you, maybe it is time to step back and do some good planning.
II. What is the nature of habits and why does this matter?
Habit is something you do repeatedly without having to think about it.
Brushing your teeth in the morning, putting on your helmet when you are on your bike, opening your notebook while at class,… are some examples of habits. Now, imagine you want to have a habit of opening your notebook after having a long day at work in your late evening when your child has finally slept. Could this be a habit? I would venture to say: Could be, but very hardly.
Whenever people tell me they want to form a new habit, what they often want is that effortless quality of a habit. But most of the habits we want to pursue are too complex to become a habit, such as writing or exercising. These activities are complex because they comprise more than two other behaviors that occur in a sequence.
For example, when you sit down to write, you do more than simply typing words on the screen or paper: you need to brainstorm, outline ideas, revise outline, and do your research, to name a few. Now, imagine writing at the end of the day when your will power is drained.
Ironically, for a habit to be effortless, the breakdown of it might look effortful. If we are to write out the statement for the habit of brushing your teeth, it should look something like this:
Every morning, after I wake up at 6:00 AM, I go to the bathroom, put toothpaste into my toothbrush (cues), and start brushing my teeth (behavior), so that I achieve a sense of freshness before starting my day (reward).
Therefore, to be successful at habit formation, you need to have two mindset shifts:
First, acknowledge the complexity of the behavior change you want to create. Every change is not the same, so they need different approaches to tracking.
Second, self-tracking is a complex behavior on its own right, so we need a plan. Such planning process is far more important than the tool you use, the behavioral metrics you track, or even whether your tracking project achieves a desirable outcome or not.
III. How to plan your self-tracking projects?
Because not everything you track need to be a habit, I would refrain from saying the term habit-tracking. Instead, I will use a broader term, self-tracking.
Self-tracking is the act of collecting a wide range of data about yourself, whether it is your behavior, time use, physical (ie. heart rate) or mental status (ie. emotion), often with help of technology, to increase self-knowledge, manage health conditions, or provide insight for research and interventions.
A good self-tracking plan comprises five key elements: purpose (why), timeframe (when), behavior (what), tool (how), and reflection (what next).
PURPOSE
Define your purpose for self-tracking by asking yourself: “Why do I want to track this?” or “What is the outcome I desire to have by the end of this project?” Clearly articulating your motivation for tracking provides a philosophy for choosing tracking methods and the tools you use.
Some examples of self-tracking goals include:
Self-knowledge: Understand my exercising patterns so I can build a sustainable training routine.
Health habit: Learn how different types of food affect my blood sugar level so I practice mindful eating and keep my diabetes 2 condition in check.
Self-development: Learn a new skill, such as brainstorming with Gen AI, by applying it to something you are interested in, such as writing.
Curiosity: Playing with an interesting app.
TIMEFRAME
Like any other project, your self-tracking plan needs a start date and an end date. This will keep you focused during the tracking period. It will also give you an anchor point to review and learn from your project rather than letting it spill into mindless tracking. A good rule of thumb is to limit your timeframe from one week to several months.
BEHAVIOR
It does not matter if you want to track a habit, a routine, or physiological status, it is critical that you know what behavior you want to observe. Note that is often an ongoing process with trial and errors. Deliberately ask yourself the following questions can give you more ideas:
What behavior do I want to observe here?
Which metrics is the most suitable for this project? Why?
Among all the possible metrics, which one is the easiest, most reliable, and most relevant to my goal now?
What is the baseline (current status) of the thing I want to track?
Do I want to change this baseline, or do I simply want to observe for now?
When you brainstorm on ideas on what to observe, it is also helpful to consider the tools you have at hand.
TOOLKIT
Tools does not make a successful self-tracking project. But it can be the missing piece that you have been waiting for to kick start a project that is otherwise ready to go.
One example is my most recent experiment with Beeminder.
Beeminder is a goal-tracking tool that combines habit tracking with commitment devices. It allows users to set goals and pledge money to stay on track. If they fail to meet their goal, they lose the pledged money. Beeminder provides a visual graph to track progress, reinforcing consistency and holding users accountable by applying financial consequences when goals are not met. It’s designed to help with various personal goals like fitness, productivity, and learning.
I have been using a read-it-later app called Readwise Reader to collect articles I want to read in my spare time. However, over the years, my library has piled up to a thousand because the number of articles I add every day while browsing the net is always more than the number of articles I can process. An obvious goal for me is to declutter my to-read inbox to regain my mental clarity.
Beeminder has been on my radar for a while, until one day, I found that there is an auto-integration with Readwise Reader, which makes it frictionless for me to track my reading. I have also recently invested in an e-reader that feels gentle to the eyes, allowing me to read more digitally without more screen time.
Everything has fallen into its place. The toolkit is now ready to help me consolidate my reading routine. I created a goal to clear my Shortlist inbox from 74 articles to 10 articles in one month by clearing two articles a day, given that I do not add any new articles to the list.
The best thing about Beeminder is their data visualization, which is crucial in a self-tracking project. It is also fun to look at a dozen of metrics telling you how you are doing.

SELF-REFLECTION
Self-reflection is the act of looking at your data and asking yourself “What do I learn about my X behavior? What can I do next?” While quantity and consistency is good to keep you going, you must, at some points, pause and ask yourself “How do I become better at this?” The whole point of quantified self is to help you increase your self-knowledge through numbers. Without taking notes of what you learn, you fall into the trap of tracking for tracking sake, which is the exact reason why tracking fails.
The downside of habit tracking occurs when you mistake consistency for mastery. This means you keep taking the action, but your skill has leveled off and stagnated.
Therefore, a good habit tracking is not enough. An idea is to tie it to a specific goal with a deadline. This is how goal tracking apps such as Beeminder come into play. When you have a goal attached to your daily actions, your attention become both intensively focused and persistently diffuse. This is the sweet pot between productivity and creativity.
That’s it for this week. See you next Tuesday.
If you find this article helpful, please do not hesitate to share it with others.
Have you ever start a self-tracking project? What habit or condition did you track?