From Aristotle to Apps: The long history of habit tracking

Here's a confession: I'm obsessed with habits. I've been trying different habit apps for over a decade. I've had multiple 1,000+ day streaks. And I even built my own habit tracking, which I use every day. If you're looking for a habit tracking app, there are dozens out there and there's likely one to help you achieve your goals.

If you're reading this, you've probably also wondered where the obsession with habits and the desire for all of these habit tracking apps came from. I did, so I dug in. I did it to hopefully better understand myself and why habits work so well for me, but also to know what to focus on with the habit tracking app I was building to help others also.

So, it turns at that habits and habit tracking has a long history, from Aristotle all the way to habit tracking apps. So lets dive in!

The history of habits & habit tracking ⏪

In an era when “tracking habits” usually means tapping a smartphone, it’s easy to forget that the quest to build better habits is as old as civilization itself. Two and a half millennia ago, the Greek philosopher Aristotle was already considering how repeated actions shape character. He noted

“We are what we repeatedly do. Excellence, then, is not an act but a habit.”

- Aristotle

In Aristotle’s view, virtuous habits formed through practice were the key to an excellent life. Ever since, philosophers and psychologists have probed the power of habit and ordinary people have sought ways to use it to achieve their goals. Habit tracking is the practice of recording one’s behaviors to promote positive change.

Habit tracking (and especially habit tracking apps) may seem like a modern craze, but the roots run deep. From handwritten journals and Benjamin Franklin’s charts to the rise of bullet journals and habit tracking apps, the tools have evolved, but the intent is the same: to understand and improve ourselves by taking control of the patterns of our daily lives.

Early reflections: Habits & virtue in philosophy 🧐

Long before anyone carried a calendar or clicked a checkbox, thinkers like Aristotle laid the groundwork for understanding habits. In Aristotle’s Nicomachean Ethics, he argued that moral virtues are acquired by habituation, that is by acting as the kind of person one wishes to become. He believed that by repeatedly performing just and temperate actions, a person becomes just and temperate. “Excellence is an art won by training and habituation… We are what we repeatedly do,” he reasoned, emphasizing that virtue isn’t innate but achieved through consistent action.

Ancient Stoic philosophers similarly advocated daily reflection on one’s conduct as a way to build virtuous habits. The Stoic teacher Epictetus suggested that “progress” in life comes from “daily examination” of one’s deeds, an idea later echoed in early Christian practices like Saint Ignatius’s Examen, a ritual of reviewing each day’s behavior. For these early sages, the focus was on why habits matter: Habits were the invisible architecture of character.

Our habits are the invisible architecture of our character.

These ideas are great, but not particularly actionable. How would I apply this? How do I track my habits? The advice was largely introspective, urging us be mindful of our actions rather than quantitative. Still, the notion that one should pay regular attention to one's behaviors was a key philosophical seed that would blossom centuries later into formal habit tracking. If excellence comes from repetition, it stood to reason that one might need to monitor those repetitions 💡

Bundles of habits: The psychology of habit formation 🌱

By the 19th century, the discussion of habits moved from philosophy to early psychology. Psychologist and philosopher William James devoted an entire chapter to habit in his book Principles of Psychology (1890), famously declaring that “living creatures… are bundles of habits”.

James observed that much of animal and human behavior is governed by repeated routines, from the daily paths we take to the way we tie our shoes. He was fascinated by how actions that start as deliberate choices gradually become automatic. “Any sequence of mental action which has been frequently repeated tends to perpetuate itself,” James wrote, noting that we are “automatically prompted to think, feel, or do what we have been before accustomed to” given the same circumstances. In other words, "habit loops" are the recurring cycles in which a certain cue triggers a routine behavior followed by some reward. These habit loops dominate our lives, often outside of our conscious intent.

James also recognized habits as the “enormous fly-wheel of society” that keeps societal order by locking people into predictable roles and routines. He saw habit as a double edged sword: it provides stability, but it can also entrench us in ruts by our thirties, after which “the character has set like plaster”, as he put it.

To James, this made deliberate habit formation in youth vitally important. He even offered practical advice for self-improvement that still sounds modern: suggesting that to form a new habit, one should “launch ourselves with as strong and decided an initiative as possible” and “never suffer an exception” until the habit is securely rooted. Each lapse, James warned, “undoes more than a great many turns will wind again”. In essence, he was advising a proto-“don’t break the chain” approach: once you start a positive streak, keep it going at all costs! As I've learned, streaks are incredibly helpful, but also have a dark side, more on that later...

By the early 20th century, behaviorist psychologists like B.F. Skinner took the understanding of habit a step further with controlled experiments. Skinner’s work in the 1930s and 40s with rats and pigeons demonstrated how operant conditioning (rewards and punishments) shapes habits.

In a classic experiment Skinner put hungry pigeons in a box with a lever that dispensed food when pressed. The pigeons quickly learned to peck the lever to get pellets. Skinner found that if a behavior is regularly followed by a reward, animals (and by extension, humans) will repeat that behavior until it becomes habitual. Interestingly, the pigeons kept pressing the lever even after the dispenser stopped giving food, implying the action had become ingrained as a habit.

From such studies, behaviorists distilled the now familiar loop of stimulus → behavior → reward as the engine of habit formation. A trigger (the lever or, in our lives, maybe an alarm or a location) cues the routine, and a payoff (food, or perhaps a sense of satisfaction) cements it in the brain’s circuitry. Habits, Skinner showed, could be deliberately built by reinforcement. This scientific work gave habit trackers an important insight: consistently rewarding yourself for completing a habit, even if just with a satisfying check mark or gold star, leverages basic brain chemistry to make the behavior stick!

At the same time, psychologists were also discovering the flip side: cues and context are powerful. In 1901, Russian physiologist Ivan Pavlov had shown how an external cue (a bell) could trigger an automatic response (a dog salivating) even without an inherent reward, through classical conditioning.

Later research by psychologists like Wendy Wood would reveal that a huge portion of our daily actions happen on autopilot. One study by Wood and colleagues found about 43% of people’s daily behaviors were habitual (done without thinking) in response to situational cues. That means nearly half of what we do each day, from brushing teeth to checking our phone, we do simply because we’ve always done it in that context! These findings underscored why tracking habits can be valuable: much of our behavior is mindless repetition, so bringing those patterns into conscious awareness is the first step to changing them.

The first habit trackers: Benjamin Franklin’s virtue diary 😇

If psychologists provided the theory of habits, many ordinary individuals over the centuries took a more hands-on approach to practice better habits. Perhaps the most famous early example is Benjamin Franklin, who in the 1720's embarked on a personal quest for “moral perfection.” Finding that good intentions alone weren’t enough “to prevent our slipping” into old ways, Franklin devised a systematic habit tracking method to keep himself accountable. In his autobiography, Franklin describes creating a small journal with charts to monitor his adherence to 13 virtues such as temperance, industry, frugality, and humility.

Franklin’s method was ingeniously analog and quantitative. “I made a little book, in which I allotted a page for each of the virtues,” he wrote. He ruled each page into seven columns for the days of the week and 13 rows for the virtues. Each day, he would place a little black mark in the chart for every slip-up or fault against that virtue. The goal was to have as few marks as possible.

He focused intensively on one virtue each week. For example, in week one, he’d try to keep the temperance row clear of any marks. In week two, temperance and silence, and so forth, cycling through all 13 virtues in 13 weeks. “Like him who, having a garden to weed, does not attempt to eradicate all the bad herbs at once… but works on one of the beds at a time,” Franklin believed this focused approach would yield steady improvement. Over multiple 13-week cycles, the hope was to see the marks (indicating faults) gradually disappear with a cleaner character emerging on paper and in life.

This 18th-century habit tracker was essentially a spreadsheet in ink. It gave Franklin concrete data on his behavior. And indeed, he reported that the experiment, while humbling (he discovered himself “fuller of faults” than expected), was fruitful: “I had the satisfaction of seeing them diminish”, he noted, as he tracked his progress. He even refined his tool, transferring his paper charts onto a reusable ivory tablet where he could wipe off the marks each cycle instead of rewriting the grid, an early innovation in analog tracking technology!

Franklin’s virtue diary illustrates why people started tracking habits: to bridge the gap between aspiration and action. He recognized that simply wanting to be virtuous wasn’t enough, he needed to measure his behavior and see his progress (or lack thereof) in black and white. The act of tracking introduced both awareness and accountability. Each black mark was a moment of reckoning, a cue to do better. In modern terms, Franklin set up a feedback loop for self-regulation. As he wrote, “the mere speculative conviction that it was our interest to be completely virtuous, was not sufficient to prevent our slipping”. Rather, “the contrary habits must be broken, and good ones acquired and established,” which required a methodical approach. His little book provided that method.

Franklin was far from alone. Inspired by such ideas, many people in the 18th and 19th centuries kept journals or tally sheets to monitor personal virtues, vices, work and prayer routines, or other behaviors. Victorian-era diarists, for example, sometimes used daily logs to track temperance (staying sober), church attendance, or charitable acts as a way to cultivate good habits and pious character.

These early habit trackers were analog and often tied to moral or religious goals. They used checklists and calendars in pursuit of self-improvement, much as we do now, but with pen and paper. A notable thread through all of them was the belief that “monitoring leads to improvement.” It’s a very old intuition that turns out to be largely true, and would later be confirmed by research.

Analog innovations: From checklists to bullet journals 📝

Fast-forward to the 20th century: the idea of tracking habits gradually secularized and expanded beyond moral virtues into everyday productivity and health. By the mid-1900s, keeping logs or charts of one’s behavior became a staple technique in many self-help and therapeutic settings, such as:

• Dieters were told to keep food diaries
• Smokers trying to quit might tally each cigarette
• Doctors asked patients to record taking medications
• People on fitness plans may track exercise or activity

In the 1960s and 70s, behavioral therapists formally incorporated self-monitoring as a tool for behavior change, asking clients to record occurrences of the behavior they wanted to change. Simply recording, they found, often produced improvements by itself – an effect so common it earned a nickname: “reactivity,” meaning people change their behavior in response to observing it.

One meta-analysis of goal tracking published in 2016 would later quantify this: on average, interventions that encouraged people to monitor their progress significantly improved goal attainment (with a medium effect size), especially when that progress was recorded or made public. In short, “what gets measured gets managed” was proving true.

Outside of clinics, the average person in the 20th century might not have graphed their habits with quite the zeal of a Benjamin Franklin, but many adopted simpler analog tracking tricks. Wall calendars and agendas became ubiquitous, and with them the practice of marking daily accomplishments, such as:

• Students put gold stars on homework charts
• Athletes logged training miles in notebooks
• Families used chore charts on the fridge

Even the humble checklist popularized in World War II for pilots and later in business by management gurus is a close cousin of habit tracking, turning repeated tasks into a list of items to tick off each day or week. Checking the box ✅ provides that little jolt of satisfaction (a mini-reward) that reinforces doing the task again.

One modern analog method took these elements and gave them a stylish, flexible twist: the Bullet Journal. In 2013, digital designer Ryder Carroll introduced the Bullet Journal system, which is a method using a blank notebook to create a personalized planner, tracker, and diary hybrid.

Bullet journaling quickly took off as a “mindfulness-meets-productivity trend” that equates organized journaling with an ordered interior life. Users create calendars, to-do lists, and most importantly, habit trackers. These are often beautifully drawn grids or charts to color in each day they stick to desired habits (water intake, exercise, meditation, etc.).

As an aside, I've noticed mostly women into Bullet Journals on Instagram due to the art/design/calligraphy aspect. The examples I've seen really are quite beautiful, pieces of artwork themselves. I also get the impression that the act of taking the time to beautifully make an entry in a Bullet Journal is itself a meditative act. This is in contrast to most habit tracking apps, which try to make the act of tracking a habit as simple/fast as possible, more utilitarian.

By the late 2010s, bullet journaling had a huge cult following (more than 8 million Instagram posts by 2019) and had turned the analog tracking of habits into an art form, as described above. Enthusiasts say the tactile act of writing and decorating their journals keeps them engaged and accountable in a way that generic pre-printed planners or digital apps don’t. Each month’s habit tracker page offers both creative outlet and personal report card with a meditative benefit.

Interestingly, the Bullet Journal craze emerged well after the dawn of smartphone apps, almost as a counterbalance for those who felt digital tools were too impersonal or distracting. It shows that even in the digital age, many people still swear by pen and paper to shape their behavior.

The bullet journal’s popularity also underscores a key psychological element of habit tracking: making it enjoyable. Drawing a neat spread, using colored pens, and getting the satisfaction of coloring in a square each day can turn the grind of habit change into a gratifying daily ritual. This echoes Benjamin Franklin’s insight that one should “envelop your resolution with every aid you know” to launch a habit. In a sense, bullet journalers are doing just that: leveraging aesthetics and creativity as “aids” to reinforce their new habits.

The emerging throughline here is essentially hacking yourself by doing whatever it takes to do the right things, and these could be different for everyone. But one of the most effective hacks, which is even used at a core feature in multi-billion dollar comapnies like Duolingo, is the streak, which we'll dive into next.

Don’t break the chain: Streak tracking catches fire 🔥

Alongside journals and diaries, another analog technique gained fame in the late 20th century: calendar chain tracking. This method was popularized by comedian Jerry Seinfeld, who reportedly used it to maintain his daily writing habit. As the story (recounted in a 2007 Lifehacker interview) goes, a young comic asked Seinfeld for advice, and Seinfeld revealed his system: get a big wall calendar, and every day you do your writing, put a big red “X” over that day.

After a few days you’ll have a chain, and your job is “don’t break the chain.” Keep the streak alive! The brilliance of this simple method is that it externalizes your progress in a stark visual way. A calendar full of X’s becomes a motivating badge of consistency, and the longer the streak grows, the more painful it feels to break it. Seinfeld’s tip struck a chord; “Don’t break the chain” became a mantra for many writers, artists, exercisers, and habit builders. People hung up calendars for everything from practicing guitar to going sugar-free, proudly extending their streaks.

This approach added a new psychological carrot (and stick) to habit tracking: streak pride. There’s something about an unbroken streak that humans find deeply satisfying and conversely the prospect of resetting to zero (losing your streak) can be a powerful deterrent to lapsing.

Modern behavioral science recognizes this as tapping into loss aversion (we really hate losing what we’ve accumulated) and the power of small wins (each day checked off is a mini-win that reinforces identity and motivation). By the 2010s, many digital tools would adopt the streak idea, giving users counters or badges for consecutive days of habit adherence, directly inspired by this streak strategy. In fact, this streak method stands as a perfect bridge between the analog and digital eras of habit tracking: a low-tech technique so effective that high-tech apps built it into their core design.

There’s an app for that: Habit tracking in the digital age 📱

As smartphones and the internet took over daily life, habit tracking exploded into a high-tech industry. The Quantified Self movement, born in 2007 when two Wired magazine editors coined the term, encouraged people to treat their own lives as sources of data to be collected and analyzed.

Soon, tracking one’s steps, sleep, diet, and habits became not just a personal project but a cultural phenomenon. By the 2010s, app stores were flooded with habit tracker apps promising to help users build better routines. There were minimalist apps that simply logged checkmarks, and gamified apps that turned your habits into role-playing game quests (like Habitica, which rewards your real-life habits with virtual points and monsters to defeat). There were also social habit trackers that let friends spur each other on, and ultra-simple ones like Streaks that focused on the classic calendar X’s. The options multiplied quickly.

Why this surge of digital tools? Partly because smartphones solved two perennial challenges of habit tracking: with you everywhere, and automated reminders. Instead of needing to remember to pull out a journal each night, an app could ping you at 9 PM: “Did you floss? Don’t break your streak!”

The phone’s always-on presence also allowed more detailed data collection. Some apps let you log not just “yes I did it” but how many reps, or how you felt, and then produce slick charts of your progress over weeks and months. Others integrated with sensors. By the late 2010s, wearable fitness trackers like Fitbit and the Apple Watch automatically recorded steps, heart rate, even sleep quality, tracking health habits without any user effort.

Apple’s own Health app and Watch “Activity rings” turned meeting daily exercise, movement, and standing goals into a visual game (close those rings!). The convenience and instant feedback of these technologies brought habit tracking to people who might never keep a paper journal.

Importantly, digital platforms also supercharged the reinforcement loops that keep habits going. Apps send celebratory animations when you log a task, award points or badges for hitting milestones, and email you weekly summaries of your accomplishments.

Each of these is a little reward, leveraging the same principle Skinner used with his pigeons. If an analog tracker gives you a gold star, a digital tracker might give you a virtual trophy. The effect on the brain’s reward system (a hit of dopamine) is similar. Over time, the habit itself becomes rewarding, but these extras help you get over the hump of early days when the new behavior hasn’t yet become second nature.

By the numbers, habit tracking’s digital boom is impressive. The global market for habit tracking apps was estimated at nearly $10 billion in 2023, projected to triple to over $30 billion by 2032. Millions of users now download habit apps in hopes of eating better, studying more, or quitting bad habits.

Companies and developers have latched onto behavioral science to design apps that will engage users: incorporating streaks (chain tracking), smart reminders (cues), stats dashboards (progress feedback), and even social accountability, where you can share your goals with friends or a coach. In a sense, these apps package the wisdom of centuries (know your habits, keep score, reward yourself) into pocket-sized assistants.

Community and competition have also entered the mix. Services like StickK (founded by behavioral economists) let people put actual money on the line (you lose a wager if you fail your habit) adding a punishment incentive. Others pool users’ money and reward those who meet step counts or weight-loss goals. The habit tracking ecosystem now spans from solo self-reflection to massively multiplayer behavior change.

Habit tracking methods through time ⏳

To summarize how tools for tracking habits have evolved, below is a timeline of different methods, their format, typical goals, and what we know about their effectiveness:

As the table suggests, the core goals of habit tracking have been consistent, whether in 1800 or 2025, people track habits to foster personal growth, health, virtue, and productivity. What’s changed dramatically is the format and scale. We’ve gone from a lone individual marking a private notebook to millions of people collectively logging into servers to quantify their lives. Each new tool, from Franklin’s ivory tablets to AI-powered apps, builds on past insights about what helps habits stick.

Why do we track? The psychology behind the practice 🧠

What drives this enduring practice of habit tracking? On the surface, it seems obvious: we track habits to make sure we do them (or don’t do them, in the case of breaking a bad habit). But on a deeper level, several psychological motives are at play:

• Accountability & awareness: Writing something down makes it real. A habit tracker forces you to confront your behavior daily. Did I do what I said I would? If not, there’s a blank space or a sad face staring back at you. This accountability to oneself can be very powerful. Many people find that if they promise to run three times a week, it’s not until they keep a running log that it actually happens. The act of tracking shines a light on behaviors we might otherwise conveniently forget or rationalize away. (Who hasn’t vaguely assumed they’re eating healthy or exercising “often” until a log shows the gaps? )
• Motivation through feedback: Seeing progress is motivating. So is seeing streaks and stats improve. Habit tracking gives tangible proof of improvement, evidence of momentum. For example, if you’ve read zero pages of books for months, and then you start a reading habit and see in your log that you read 100 pages last week, that concrete progress fuels your desire to continue. Many trackers speak of the little thrill in adding another entry to the log, akin to crossing an item off a to-do list. Psychology calls this the reinforcement effect: the behavior (reading) gets positively reinforced by the satisfaction of recording it and seeing the progress bar inch forward.
• Structure & routine: Filling in a habit tracker can become a ritual that anchors your routine. If every night before bed you reflect on your day and tick off habits, that process itself signals closure of the day and primes you for tomorrow. The tracker acts like a gentle drill sergeant, providing structure amid life’s chaos. People often start tracking during times they feel life is unruly or they’re not living as intentionally as they want. The tracker is a self-imposed structure to ensure priorities don’t get lost. It externalizes your intentions so they don’t drown in mental clutter.
• Reward & dopamine: As mentioned, even trivial rewards can train our brains. Habit tracking leverages this with gold stars, streak counts, “karma points,” and other gamified elements. Checking a box seems so minor, but neuroscientists note that even these small satisfactions likely trigger a bit of dopamine release, which is our brain’s way of saying “yes, that was good, do it again!” Over time the habit and the reward become associated, and eventually the habit may continue even when one stops formally tracking, because it’s been internalized.
• Identity & commitment: On a lofty level, tracking habits is a way of changing one’s identity. Author James Clear (in Atomic Habits) argues that the most effective habit change happens when we adopt identity-based habits, so doing the habit confirms the kind of person we want to be. In other words, it’s one thing to say “I’m tracking how often I write,” but another to say “I am a writer, so I write daily and my log is proof of that.” Each logged entry becomes, as Clear puts it, “a vote for the type of person you wish to become.” Conversely, an empty log is dissonant with that identity. Clear writes, “The key to building lasting habits is focusing on creating a new identity first. Your current behaviors are simply a reflection of your current identity… To change your behavior for good, you need to start believing new things about yourself”. By tracking a habit, you reinforce the narrative “I’m the kind of person who keeps track and improves.” This can strengthen resolve, especially when motivation flags. It’s no longer just about the streak, it’s about who you are. Indeed, seeing months’ worth of entries in a journal can instill pride and a sense of personal growth because "I am someone who can commit and follow through", which often spills over into confidence in other areas of life.
• Problem solving & optimization: Finally, some track habits to glean insights and optimize their routines. This is more prevalent with digital tools that allow data analysis. For instance, someone might track their mood alongside habits to discover correlations (e.g. “On days I meditate and run, my mood is higher”). The Quantified Self community loves the aspect of using habit data to run self-experiments and adjust for better outcomes. Even a simple tracker can help identify patterns: “I notice I tend to skip workouts on Wednesdays, so maybe that day is too busy. How can I adapt?” In this way, tracking isn’t just about discipline, it’s about learning one’s personal patterns and tweaking the environment or habit to set up better success (a strategy behavioral scientists call “habit design” or making the good habit easier to do).

Given these motivations, it’s clear habit tracking fulfills both an emotional and a pragmatic role. It gives a sense of control, such as "I am managing my life, not just drifting." This is deeply gratifying in itself, especially when so much of life feels uncontrollable. It’s telling that during times of upheaval (like the COVID lockdowns), interest in habit trackers and journals spiked, as people sought structure and small wins amid uncertainty.

Does habit tracking really work? Benefits & pitfalls ⚖️

After all the effort of logging and journaling, the big question remains: does it pay off? It seems the answer is yes...but with caveats.

Numerous success stories attest that habit tracking can be transformative. It has helped people lose weight, learn new languages, get in shape, save money, you name it. The mechanisms by which it works are backed by research: making a commitment, monitoring progress, and getting feedback significantly increase the chances of achieving a goal.

A comprehensive 2016 meta-analysis of 138 studies found that interventions prompting people to monitor their goal progress led to higher rates of goal attainment than in control groups, with a notable effect size. The effect was even stronger when the records were physically recorded or shared publicly (as opposed to just mental notes), which supports the idea of habit tracking. In other words, writing it down works, and sharing with others (or even just a device) adds accountability that boosts success.

For building specific healthy habits, tracking often shows measurable improvements. Consider weight loss: studies in behavioral medicine consistently find that food journals (tracking what you eat) correlate with more weight loss. Similarly, pedometers or step-counting apps often lead to increased daily steps compared to no tracking, as people get competitive with themselves to meet targets. Even in addiction recovery, something as simple as counting days sober and collecting sobriety chips provides motivation through visible progress.

However, habit tracking is not a panacea, and it doesn’t work the same for everyone. There are some potential downsides and limitations to be mindful of:

• Obsessing over data: For certain personalities, tracking can slide from helpful structure into unhealthy obsession. If one becomes overly fixated on the numbers or never allowing a single day off, it can induce anxiety. The process that’s meant to reduce stress and create order might backfire. Some people report that once they started meticulously tracking, they felt a “performance anxiety” about it – turning even leisure activities into a source of stress. For example, one individual shared that watching TV, which used to be relaxing, became an anxious activity once he set a goal of limiting screen time and tracked each episode watched. It “became a task to complete rather than a pleasure… turning a leisure moment into a source of stress”.
• Loss of spontaneity: Along similar lines, habit tracking can make life feel too regimented for some. When every hour or action is accounted for, people may feel they’ve lost a degree of spontaneity or freedom. Not everyone enjoys living by charts, some find greater happiness by not tracking and allowing more flow. It depends on the person and the habit. A creative free-spirit might find a habit log stifling, whereas an analytical type finds it comforting.
• All or nothing mindset: The streak concept, while motivating, can also be brittle. If someone has a long streak and then inevitably breaks it (life happens, you get sick or an emergency comes up), the psychological fallout can discourage further effort. One missed day shouldn’t negate 30 good days, but the human mind often reacts as if it does, leading to a “what the heck, I failed” abandonment. Good tracking systems often explicitly build in “forgiveness”, encouraging users not to panic over a break and maybe focusing on consistency over a weekly average rather than unbroken perfection. But it’s easy to fall into the trap of chasing perfection.
• False sense of accomplishment: Sometimes people get addicted to the ritual of tracking more than the habit itself, and may end up gaming the system. For instance, someone might choose very easy, quantifiable habits just to fill their tracker and feel productive, while neglecting harder but more meaningful changes. Or one might check off “drink water” and “take vitamins” diligently (good things, to be sure) yet avoid tackling that big project or difficult habit that isn’t as fun to log. Tracking is a tool, but what you choose to track matters! It can become a form of productive procrastination if not aligned with genuine goals.
• Privacy concerns and over-quantification: In the digital realm, sharing your habit data or having it stored by third parties can raise privacy issues. Not everyone wants their life data on a server. And trying to quantify every aspect of life (the extreme end of Quantified Self) isn’t everyone’s cup of tea. It can make life feel like a spreadsheet, neglecting qualitative aspects like emotions, creativity, and relationships that don’t fit neatly into a habit tick box.

Yet, for most people, these pitfalls are avoidable with a balanced approach. The key is using habit tracking as a servant, not letting it become the master. Flexibility is important: if a particular tracking method is causing more stress than benefit, it’s okay to modify or drop it. In fact, some experts recommend tracking in “streaks” or bursts rather than indefinitely, at least until a habit is ingrained. For example, track meticulously for the first 60 days (the approximate time some researchers say it takes to form a habit on average) and then, if you feel the habit is pretty solid, you might not need to keep tracking unless you notice yourself slipping. Habit formation has a natural arc: early on, you need external scaffolding (like a tracker) to support the new behavior. Later, the habit can often stand on its own, having become part of your routine or identity.

From the research perspective, one fascinating finding is that the act of tracking can change how we think about the behavior. When we monitor ourselves, we become more objective about our actions (less “ostrich effect” of sticking our head in the sand). One study mentioned in the Handbook of Behavior Change notes that prompting self-monitoring consistently leads people to align their behaviors closer to their goals. Essentially, tracking forces a confrontation between current self and goal self, and most people will adjust behavior to reduce that discrepancy (a concept rooted in self-regulation theory).

So, the balance of evidence and anecdote suggests habit tracking does work for many, as long as it’s approached with the right mindset. It’s not magic, you still have to do the exercise, writing, studying, or quit smoking, but it is a proven aid in making those changes stick. As one behavioral scientist quipped, “Monitoring is like the thermostat of behavior change: you have to check the temperature to know whether to heat or cool.” In other words, tracking keeps you calibrated toward your goal.

The habit loop & beyond: The science of sticking with it 🔁

No exploration of habits would be complete without examining the habit loop, a concept that underpins why habit tracking works. In 2012, journalist Charles Duhigg synthesized decades of psychology and neuroscience into a catchy framework in his bestseller The Power of Habit. He described the Habit Loop as consisting of three stages: Cue, Routine, Reward.

The cue is the trigger that initiates the habit (time to go to bed, so you brush your teeth; or you get an email notification, so you automatically open your inbox). The routine is the behavior itself (the tooth brushing, the email checking), and the reward is what you gain from it (minty fresh feeling and no cavities, or the resolution of curiosity when you see the email content). Over time, this loop becomes so ingrained that the cue will almost involuntarily lead to the routine, as the brain anticipates the reward. We see this in our own lives: the 8am alarm rings (cue), you put on your running shoes and jog (routine), and then you feel great afterwards (reward). Eventually, your morning isn’t complete without that jog.

Habit tracking can be thought of as an external support to this internal loop. How so? First, a tracker often serves as an additional cue. The presence of a habit tracker (whether it’s a journal by your bedside or a reminder ping on your phone) is itself a trigger that says: “Hey, remember to do X.” It piggybacks on your environment. For instance, a habit app’s reminder at 7pm becomes the cue to practice guitar for 15 minutes. Over time, you might not need the reminder because 7pm itself (or finishing dinner) becomes the cue. But at the start, the tracker’s job is to be a reliable cue.

Second, the act of recording provides a reward. Checking off the habit or filling in that bubble gives a small sense of accomplishment (some call it the “gold star effect” from childhood). That positive feeling can stand in as a reward until the intrinsic reward of the habit kicks in. Many habits, especially healthy ones, have delayed rewards: the future benefit of exercise is great, but the immediate feeling might be fatigue or soreness. A tracker can inject an immediate reward (“Yes! I did it, look at me go!”) to help bridge that gap. Over time, as the habit becomes ingrained and the person experiences more of its intrinsic rewards (e.g. strength, confidence, stress relief from exercise), the need for the external reward diminishes. But in early stages, it’s critical and I've relied on this mechanism myself many times.

Finally, tracking helps with what one might call “habit hygiene” to analyze and adjust the loop if it’s not working. If you consistently fail to perform the routine, you can tweak either the cue or the reward. Maybe the cue isn’t strong enough and you keep forgetting, so you add a second reminder or tie it to an existing routine (this is called habit stacking, e.g. “after I brew my morning coffee, I will meditate for 2 minutes”). Or maybe the reward isn’t compelling, so you promise yourself a bigger treat if you hit a streak of 7 days. The tracker provides the record that something’s off in the loop, enabling this kind of troubleshooting.

Modern apps increasingly incorporate behavioral science hacks to optimize habit loops. They use techniques from BJ Fogg’s Tiny Habits (making habits so small and easy that you can’t not do them, to overcome initial resistance) and implementation intentions (cue-action plans like “If it is Monday, Wednesday, or Friday at 6pm, then I will go to the gym”). Some apps use identity priming, asking you at signup to envision your goal (“I am becoming a runner”) so that every time you log a run, it reinforces that identity. In essence, they blend the old wisdom and new research: cues, repetition, rewards, and self-identity.

One emerging angle is the use of AI coaches or smart habit trackers that adapt to the user. For example, an AI-based tracker might notice, “You usually fail to journal on Saturdays,” and proactively suggest a solution (“Would you like to set a reminder earlier in the day on Saturdays, or maybe change the time of your journaling on weekends?”). This is the frontier that the next generation of habit trackers is exploring, which is a kind of personalized behavior change coach in your pocket, using your tracking data to give tailored advice.

Throughout all these developments, the throughline remains behavioral psychology 101: to change a habit, you need to identify the behavior, routine-ize it with cues, and reward it so it sticks. When problems arise, often it’s because one of those elements is missing or misaligned. Habit tracking assists at each step: helping identify (self-awareness), routinize (schedule + cue), and reward (satisfaction of progress).

From ancient wisdom to modern self-mastery ⏩

Habit tracking may seem like a simple practice (put a mark on the calendar when you do the thing) but as we’ve learned, it carries the weight of centuries of wisdom about human behavior. Aristotle understood that we become what we repeatedly do. Benjamin Franklin proved that what we repeatedly write down, we will do. Modern science confirmed that what we measure, we improve. And today’s technology amplifies these truths to help us change even the most stubborn behaviors.

In a very real sense, the evolution of habit tracking reflects our evolving understanding of ourselves. Early on, it was rooted in moral philosophy and the desire for virtuous character. Then it became a tool for self-made individuals like Franklin to reach personal excellence. In the 20th century, it was adopted by science as a method to improve health and productivity, recognizing that we are, as William James said, “mere bundles of habits” that can be re-bundled with the right techniques. And in the 21st century, it has become democratized and ubiquitous so anyone with a smartphone (which is billions of people) has access to a “pocket life coach” to monitor and encourage their habits.

Yet, for all the innovation, one is struck by the continuity. A Roman Stoic or an 18th-century Founding Father would readily grasp the point of a bullet journal or a habit app since it might be a different medium, but it's the same idea. We still seek, as Franklin did, “the encouraging pleasure of seeing… the progress made”. We still struggle against “the force of perpetual temptations” and use daily examination to guard against backsliding. What's so interesting is this negative "Force" is reminiscent of "Resistance" from Steven Pressfield's 'The War of Art', which is one of the most memorable books I've read. From the book:

“Every morning you wake up and the dragon’s there and you’d have to slay that dragon anew every morning. The only difference is that after you’ve done it enough times you now are confident that it can be done, but it never goes away, and there’s no magic bullet.”

- Steven Pressfield, The War of Art

But doing the hard work and pushing through the "Force" as Franklin called it or the "Resistance" as Pressfield called it, makes it more manageable over time, it has cascading positive effects. That is, a good habit can be a foundation for another (Franklin noted temperance made it easier to achieve silence, order, etc., just as today we talk about “keystone habits” that cascade into others). And we still find that when we fall short, “with mere good intentions, hell is proverbially paved,” as James wryly commented, it’s the consistent actions that count. We just have to put in the work, that's the only way.

Perhaps the biggest change today is that we can see, in aggregate, how our habits shape us as a society. The data from millions of fitness trackers tells public health researchers how active or sedentary we are. Our collective screen-time reports raise societal questions about digital well-being. Habit tracking is not just personal anymore, it’s increasingly part of conversations in workplaces (employee wellness programs), schools (students tracking study habits), and healthcare (apps for managing chronic conditions). We’re quantifying ourselves at every turn, for better or worse, and learning a lot in the process.

In the end, habit tracking is a means to an end, and that end is a better life. That could mean a healthier body, a calmer mind, or a more virtuous character. The beauty of habit tracking is that it acknowledges a humbling fact: change is hard (we’re fighting ingrained neural circuits, after all), but it then empowers us with a simple, concrete strategy to do something about it. Track it, and you can change it. As one Bullet Journal aficionado put it, “It’s not about making life a spreadsheet. It’s about writing your own story, one day at a time, and actually reading it.” That sentiment connects right back to the ancients: live examined days, and you will live a better life.

"The unexamined life is not worth living."

- Socrates

That is, be not just a passenger drifting where the winds carry you, but an active participant, this is your story, you're the main character. Act like it.

So whether you choose a Moleskine notebook or the latest habit tracking app, the act of habit tracking carries a bit of ancient wisdom in its modern guise. It’s a handshake between your present self and your aspirational self. It’s a daily nod to the idea that we are indeed what we repeatedly do, and that with a little vigilance and a pen or phone in hand, we can repeatedly do what we want to be.

A personal reflection 🤔

Researching this article took a couple weeks off and on. Since I'm building a habit tracking app myself, it gave me pause because all habit tracking apps are pretty similar, they just have different styles, rewards, gimmicks, etc. But it forced me to ask 1) why are there so many habit tracking apps and 2) why do I feel compelled to build yet another one?

There are so many habit tracking apps because tracking habits is a deeply personal activity that varies person to person. In a way, finding one that works for you is learning how to hack yourself, and everyone is wired differently. That's the challenge and the opportunity.

There's also a low barrier to entry to build habit tracking apps (they are simple), so anyone who can write half-decent code (which isn't really even a requirement anymore thanks to vibe coding) can build their own that uniquely scratches their own itch. It's also a huge market with abvious demand.

So, why do I feel compelled to build yet another one? Well, I've used dozens of them over the years and have multiple 1,000+ day streaks. I've learned what is amazing at day 60 or even year 1, but counter productive at year 2 or 3. I want to fix those things by achieving implicit flexibility through intentional simplicity, so what works for me will also work for others.

There's also no clear winner in the habit tracking category, but I plan to make us that winner. If a billion people can use the same iPhone, I can make a habit tracking app that a billion people use as well. Interestingly, I think that's also the only way to solve it since, leveraging the power of AI, you can now finally have enough data points to understand/guide personalized habit formation, integrate meaningful life domains, use adaptive difficulty levels, use community for accountability and share AI-powered insights to give users 80% of the results for 20% of the effort.

So the simple answer is, it wasn't possible to solve this millennia old problem until now, so building the dominant habit tracking app also wasn't possible until now, and we're the perfect ones to do it. This is a long game of investing in what won't change: bending the arc of human behavior to give us all more fulfilling lives.