How To Help Users of Task Management Apps Have Fun At Every Level

Why do people enjoy playing games? That’s easy… they provide a huge bang for the attentional buck — lots of engaging fun opportunities for learning — in return for a very small investment.

While this is well-known, it may come as a surprise to think that they hope to have the same experience while using task management apps such as Todoist, Wunderlist, or Google Tasks.

In this article, I explore why they are often left disappointed. Instead of getting what they want, they get what designers give them: efficiency, visually attractive interfaces, or non-essential features such as links to their team-mates.

As a result, users don’t become “players”. In other words, their game-play is thwarted.

This is a lost opportunity. After all, task management is more than a mere diversion. There’s a thrill we all experience from the completion of our most important tasks and goals. It’s more natural than the artificial act of finding and capturing Pokemon.

In fact, the key to living a fulfilled life is related to setting and completing challenging objectives in all spheres of life: in this context, a task management app is a critical tool.

In my prior article, What Task Management App Developers Can Do to Catch Up with Pokemon Go I described ways to gamify task management at all levels of a player’s journey. This time around, we take a deeper dive into each level and the games people hope to play. The payoff is huge: designers who appreciate the desire for engagement can produce apps which meet deep psychological needs. It could turn an interesting app into a mainstream, runaway hit rather than a tool for productivity geeks.

Lessons from a Holocaust Game

Is it possible to turn these tools, which operate like dull databases, into games? Consider an extreme example: the gamification of a tragic experience in order to survive its throes.

While this may sound farfetched, it’s precisely the premise of the fictional movie, “Life is Beautiful.” (Spoiler alert.)

According to Gamification: How to Save a Life the movie includes a life-changing game played between the father (Guido) and his son (Giosué) while they are prisoners at a Nazi concentration camp.

In order to protect Giosué, as well as his innocence, Guido pretends the trip is a gift for his birthday and turns the camp into a game: hide from the guards, keep quiet, and you earn points; cry, want to see your mother, ask for extra food or get caught by the guards, and you will lose points; the first team to earn 1,000 will be able to go home and will win a new tank.

While I watched the movie for the first time, I didn’t notice these elements at all — maybe because I was crying so much. That realization only came later, which led me to watch it again. This time around, I noticed all the elements… and still cried.

If you are a person with an interest in gamification, it’s hard not to walk away from this experience without wondering about the power of this technique. If it’s possible to use it to transform an awful experience, what could it do for everyday boredom? Or tedium? Or even the practice of using an app to manage your tasks?

Why Users Construct Games to Play

To explore that question, let’s look at the reason Guido and others prefer gamified environments and go out of their way to create them.

Case in point: Army veterans who join the corporate world sometimes complain that they miss the discipline of After Action Reviews. These are structured efforts undertaken by teams to analyze a just-concluded exercise with a view to learning what worked, and what didn’t. Veterans wonder why the corporate world has no such equivalent, leaving employees devoid of feedback.

Recent college graduates repeat the complaint. Accustomed to short gaps between actions and feedback (such as taking tests and receiving a grade) they often feel lost in their first jobs. Learning how they are doing in objective terms is hard.

By contrast, in the typical video game this gap is reduced from days to mere seconds. The player’s performance is always available — clearly stated — allowing for short, rapid cycles of learning and improvement.

It’s human nature to want an answer to the question of “How am I doing? So it’s no surprise that we gravitate to activities such as games and sports which give us rich answers.

By contrast, as important as task management apps are to our daily activities, they tend to offer precious little feedback to their users. Instead, they merely act as databases, possessing only the information we have already entered.

In other words, they don’t tell us anything we don’t already know. Therefore, users rarely become players, it’s only when they create their own Guido-like reality. If you search the productivity blogs you can find the exceptional individual who does so on his/her own, without much help from the app he/she happens to use.

Overarching Games

In my prior article, I suggested that there are two kinds of task management games we all intend to play before we even consider the use of an app. One has to do with our overall journey from the lowest to highest of six levels, while the other has to do with our game-play at each level, as shown below.

With respect to the former, in our prior discussion we looked at the “Time Demand Capacity Game.” (A time demand is a self-imposed task.) To recap, it’s a game of matching your volume of time demands with your capacity. In other words, it’s an effort to find a perfect balance between your commitments and your skills. When you win at this game, you avoid unwanted symptoms such as feelings of overwhelm due to the slippage of a task through the cracks, never to be completed. Some may relate to this as a “Zero Slippage Game.”

In reality, most people play the Time Demand Capacity Game in fits and starts, using techniques and tools drawn from more than one of the six levels. Most people are not purists... their self-taught habits lead them to use multiple techniques, some of which are limiting.

It’s understandable. Their knowledge of these is incomplete, so their self-made solutions are ad-hoc and uneven. In this article, to simplify the discussion, I downplay this reality, but do keep it mind. It hinders their game-play, getting in the way of progress from one level to the next.

However, as universal as the Time Demand Capacity Game might be, it’s not the only game played at all six levels. There are others. One way to discover them is to pick apart the fundamental practices which players use to manage tasks. To accomplish this delicate task, I’ll borrow the framework from my book, Perfect Time-Based Productivity — A unique way to protect your peace of mind as time demands increase.

The framework consists of a number of practices used to manipulate time demands. Let’s highlight a few.

Capturing — the activity of converting a time demand from its birth as a psychological object (such as a passing thought) into a safer, more solid state. This activity is the first step you take to preserve a task, so it can be completed later. Errors occur when this conversion fails so that a time demand is accidentally forgotten.

A Capturing Game: people who become expert at Capturing play a “Failure-Free Capture Game.” They set themselves a goal of writing down, recording or typing up every single time demand that comes to mind, without exception. (It’s a form of the Zero Slippage Game mentioned earlier.)

Emptying — the activity of removing a time demand from a point of initial capture (like a paper pad) and recording it somewhere safe in your system e.g. in your To-Do List or digital calendar.

An Emptying Game: While playing the “Inbox Zero Game” you ensure that none of your points of initial capture ever become overfull. Instead, each one is reduced to a vacant state on a regular basis.

Scheduling — the activity of converting a time demand into a scheduled task in a calendar. Most people do this invisibly using a “mental calendar”. When it becomes overwhelmed with too many tasks, they migrate to a paper or digital calendar in search of greater reliability.

A Scheduling Game: When you play the “Feasibility Game,” you ensure that your written or mental calendar is, at all times, realistic. Winning this game means reducing the time it takes to recover from unplanned disruptions.

Switching — the activity of ending one task and, after some consideration, beginning another.

A Switching Game: The “Best Choice Game” is one in which you always pick the optimal task to execute after the completion of a prior task. In general, you want to make smart choices based on data in your personal memory, schedule, lists, capture points, etc. You may also want to avoid poor choices, such as devoting time to unwanted tasks such as social media, video games, or television. (I recently published an article for designers on “The Informed Self” which speaks to this practice.)

Even if you are not a time-based productivity designer, you may notice that this list is incomplete. There are lots of other overarching games people play in task management. You may also notice some gaps in how well some of these games are played. Many are hard to engage in because there is little support from devices or software.

By and large, as an unconscious player of these games you are likely to be unaware of their origins, making it impossible to for you to explain to a designer who happens to give you a call. As Clay Christiansen (the “jobs to be done” guru ) advises us: you cannot uncover the job user/players are trying to get done by simply asking them direct questions.

He argues that it takes a special crafted approach to understand what is important to user/players and why. When it’s used, you can find points where their game-play is obstructed and come up with new methods, apps, devices or tools.

Players who benefit from these products may respond by up-leveling their skills, in keeping with the “Time Demand Capacity Game.” As they up-level, they take a path from Level 1–6 as shown in the diagram above. If it’s accurate, then as a designer of products at any level, you may be able to predict the path a player will take.

Their drive to increase the number of time demands they manage may come from technology advances. Many people simply follow the practices of others.

It may also come from their inner motivation. Recall this statistic from the prior article: about half of all employees are dissatisfied with the amount of time they have available to complete their tasks. They are ripe for a change.

However, let’s take a moment to consider the fact that the other 50% are quite happy. Is this the end of the road for them, in terms of improvements?

My observations suggest that if they are highly motivated they continue to craft continuous, incremental improvements. The only difference is that it takes place at a single level.

Not to be overlooked, they play an “Implement-Check-Fix Game” in which they manage their lives to produce a constant volume of time demands. In short, they have no need for higher levels.

With an understanding of these overarching games, let’s examine some of the specific games played at each level.

The Games People Play At Each Level

To help us understand these games, let’s review the core attributes of a well-designed game which I shared from my prior article. They each have:
- Objective Goals
- Easy to comprehend score-sheets
- Feedback mechanisms
- Autonomy to make choices
- Coaching

Whenever one of these elements is missing, your experience as a player is possibly thwarted, leading to frustration. However, it also points to a possible commercial opportunity. A smart developer who discerns the gap correctly might carve out a novel solution.

To see these gaps, let’s once again use the Clay Christensen framework. According to him, we need to analyze the job which users of task management apps are “trying to get done.” In order to achieve this end, users “hire” particular solutions to solve problems at each of the six levels.

Level 1 Games — Memory

From our conversation about Capturing, we discovered that when we create time demands we need to capture them in a place that’s reliable. Without fail, the first capture point we teach ourselves to use as adolescents is memory. Psychologists would say that we hire “prospective memory” which is defined as the memory you use to complete activities in the future. (Retrospective memory, by contrast, is all about remembering past occurrences.)

While it’s our first choice, there are many adults who never escape this level at all which limits their capacity in later years. As one participant in a recent workshop said: “Before now, I thought that I should be able to remember everything!” She was playing an impossible “Remember Everything Game.”

While this game is recognized by most modern professionals as one that’s limiting, there happens to be an entire sub-field of psychology devoted to improving prospective memory. Experts in this area often focus on seniors who, for example, must find ways to remember to take their medication.

A few have gone on to develop games like Virtual Week, which try to improve the prospective memory of elderly patients.

But games like this are rare. Most people play the Remember Everything Game without a real score-sheet, relying on feelings and hunches. It’s vague. When they remember to complete time demands, they feel “on top of things.” When they forget and stuff falls through the cracks, they feel overwhelmed.

These are poor indicators. They don’t allow for good game-play, which is one of the reasons most adults up-level. As they look to do so, contemplating the practices required at higher levels, they may balk. For them, the use of a tangible “prosthesis” like a To-Do list or calendar is a sign of weakness.

Most adults do appear to make the switch, even though most of us resort to using memory to different degrees, depending on the situation.

Level 2 Games — Paper
The player who decides to up-level from Level 1 to 2 faces a few unique challenges. One is that unlike the narrow confines of a computer game like Angry Birds, up-leveling requires the use of different physical tools. This complicates the transition because it requires the adaptation of new habits, practices and rituals.

Also, bear in mind that failure can be costly.

When I played Angry Birds I failed to get past a very, very low level. Apparently, there were two year-olds who were doing so with ease.

While that failure was embarrassing, it’s entirely different than failing to undertake a task such as paying your phone bill. In this case, the stakes are much higher.

From what I gather, becoming a better Angry Birds player is a function of “failing fast and failing often” in order to develop the right skills. Failure to progress has more to do with personal pride and devoting more time to succeed.

However, allowing your phone service to lapse because you were making a transition from one level to the next is different. It’s more like changing the wing on an airplane in mid-flight. You must still perform an essential function (managing your tasks,) even as you attempt to upgrade your skills. Therefore, failing fast and failing often isn’t an option.

If you decide to up-level from Level 1 to 2 perhaps the first challenge you face is the need to carry around a new physical object — a planner which has a To-Do page of tasks, for example. It’s a “Carry Around My List Game.” Back in the early 1990’s (when levels 3–6 didn’t exist) people who always had their leather planners by their sides were seen as being productive, and serious — they were the winners at this game.

Another new practice that becomes important in this particular transition is the need to instantly write down each task. It’s a version of the “Failure-Free Capture Game” mentioned earlier which takes place when someone learns the skill of Capturing.

There also happens to be a “Crossing Out Game” you may remember if you have ever used a paper list. Players of this game like the kinesthetic and psychological experience of crossing out a completed task on a paper list with a pen or pencil.

People who use paper in today’s world probably feel pressured (or tempted) to up-level. While fascinated at the possibilities, they may have felt some resistance to the idea of handing over their precious tasks to a piece of software or hardware “owned” by an unseen third party. They rightly recognize that ownership could be a problem if the device or software breaks. By contrast, hiring a paper solution has no ownership problem.

At the same time, I vividly remember the moment when I decided to “fire” paper as a solution. Landing in a foreign country, I came off the plane without my planner. Left in the pocket of the seat in front of me, it was gone.

I quickly bought a Personal Digital Assistant (PDA) and never looked back.

Level 3 Games — Simple Task Apps

The widespread availability of the mobile internet means that there are more players jumping to this level directly from Level 1 than ever before. They skip the use of paper lists altogether.

It’s the first of our six levels that requires you to develop skills such as keeping a device charged, implementing appropriate upgrades and evaluating software/hardware companies’ trustworthiness. These practices collectively represent a “Manage My Mobile Device Game.”

Simple Task Apps offer you, as a user, no more than basic list-making, syncing and cloud storage. But they represent a powerful improvement over prior levels. For the very first time, you are encouraged to play a “Total Task Entry Game.”

It’s simple enough to understand. Now, you can feasibly enter every single task that comes to mind without any limits. At the two prior levels there were practical limits. With cloud storage, your entries are perfectly safe. If you sync your data, you are never far away from it.

Fortunately, if you perfected Level 2, you may have already mastered the practice carrying around your and entering tasks immediately. These are skills which are learned, and never abandoned.

You only begin to contemplate the next level when your list becomes too long. This happens to be true of all six levels — when the number of tasks you are trying to manage exceeds a particular threshold, you start looking around for alternatives.

Level 4 Games — Complex Task Apps

As a player who upgrades from Level 3, you are probably already comfortable with digital technology. In fact, you already played a multi-level “Cognitive Offloading Game” which involves the use of as little personal memory as possible.

In my first article, I explained that the primary reason to “hire” a Complex Task App is to break up a single long list into shorter lists. (If you have questions about why we make this switch, check out my answer on Quora.) In my answer to the question “What ways do people prioritize their To-Do list?” I outline a hypothesis developed from my research: people tag their time demands with a surprisingly large number of subconscious attributes. (This idea is explained in my book.)

For example, a time demand may be written as “Remember the Milk.” At the moment of creation, you subconsciously tag it with attributes such as:
- where it should be purchased
- how long the task takes
- when it may be due
- how urgent it might be
- how much you intend to pay
- its level of importance 
Plus there may be others.

To make life easy, you only consciously focus on a tiny subset of these attributes on a daily basis. (Usually it’s just one.) As a consequence, you use only one attribute to tag your tasks in your app. This choice of attribute is not random — you use the one which represents your scarcest resource. It’s the one you care about most.

Most Complex Task Apps allow you to choose your own tag, granting you the ability to manipulate tasks in useful ways. The use of these tags when you are Switching, for example, is one way to master the “Best Choice Game” mentioned earlier.

You also become a better player of a new “Complex Execution Game.”

It’s one that is based around a simple fact: when a time demand is created, you usually have an idea of when you wish it to be executed. It may be envisioned as an exact moment e.g. 6:00 PM today, or as a time-frame e.g. this evening.

Skillful players of this game experience a close match between their intentions and their realization i.e. they complete tasks “on time.” But this game isn’t limited to temporal attributes. It can easily be extended to other attributes e.g. completing all your @Home tagged tasks when you are located at home.

Playing the Complex Execution Game well obviously relies on the quality of your tagging. If we dig a little deeper to understand what skillful tagging looks like, we find three sub-skills: selecting the right attribute to use, attaching the correct tag , and remembering to tag every task at the right moment. Collectively, these three sub-skills makes up a new game — “Attaching the Best Task Tag”.

However, while many kinds of tags are possible, they are not all equal in impact. For many people, temporal attributes (e.g. duration, start time, due date) become the most important. Here’s why.

If you continue to increase the number of time demands you try to manage, you run into a predictable problem — a lack of time. Whereas time pressure is not an issue for everyone, it’s one that afflicts anyone who creates a lot of tasks.

The symptoms are clear. You start running out of free time as tasks begin to slip through the cracks. Even if you keep an appointment calendar, your mental calendar used to manage all your other tasks becomes impossible to manage. It increasingly dominates your attention.

Like most people, you probably respond by trying to make the most of the temporal tags offered by some Complex Task Apps, such as due dates and task durations. Perhaps, you reason, if you can tag each task with these temporal tags, and religiously sync your tasks with your appointment calendar, you might be able to expand your capacity.

This tactic works well for a while…but not for every long. As I described in the prior article, if unwanted symptoms persist you must up-level.

Level 5 Games — Calendar of All Tasks

At this level you replace the combination of task lists, an appointment calendar plus your mental calendar with a single digital calendar. As you may imagine, this is a big change.

In order to become a better player of the Cognitive Offloading Game and the Time Demand Capacity Game you start to engage in a new practice: “Total Task Scheduling.” This skill involves the placement of all your tasks in a calendar before you execute them one by one. (In this context, lists are only used on an occasional basis to support your calendar e.g. the use of a grocery list.)

If you are one of the fortunate few to implement this technique successfully, you experience a newfound power. For the first time, you are able to find all your commitments in a single, time-optimized location. This allows you to play some brand new games such as a realistic “Life Balance Game.” You can mindfully and proactively apportion time spent at work, with family, on your own and in self-improvement so that your well-being is handled.

You can also play an “Energy Balance Game” in which you try to schedule tasks according to your biorhythms — a measure of your internal energy.

Lastly, different “Task Coordination Games” which are related to project management become possible. You find yourself able to build and execute long sequences of dependent tasks.

After you make the switch, you quickly learn that Total Task Scheduling isn’t easy because it requires other new games. For example, you must learn to play a “Calendar Puzzle Game” which involves doing a rapid re-shuffle of your schedule when circumstances change. (I liken this challenge to solving a 1,000-piece jigsaw puzzle.)

Because things change so much from today to tomorrow, it’s a game you must learn to initiate every single weekday morning. At least. You sometimes need to play it more than once each day. Playing it well requires specialized tactics and also a fair measure of discipline. In an environment which is full of surprises or disruptions, you spend more time than you’d like playing it.

Kevin Kruse, author of The 15 Secrets Successful People Know About Time Management, showed that Total Task Scheduling is a popular practice of CEO’s, millionaires and Olympians. They often possess Type A personalities, showing a high propensity for time stress.

Also, Computer Science professor Cal Newport, showed that the technique is critical for doing what he calls “Deep Work.” It’s an immersive state, quite similar to the Flow state described by Mihalyi Csikszentmihalyi.

Unfortunately, most people who try to make the transition to Total Task Scheduling fail. The tools are hard to use and the habits are even harder to learn. It’s lonely trek — most who try to reach this level must do so on their own. There are precious few helpful resources.

Also, there is no community of Total Task Schedulers in existence. While there are others who have mastered this skill, they don’t appear to be organized in any single place.

Perhaps it’s the reason why there is a rather long list of authors who specifically advise against this approach.

Yet, there are players who persist. Like them, I played these games, struggling with calendars which were really designed to be appointment calendars, rather than a calendar of all tasks. Then, just after my book was published, I was introduced to a brand new level emerged I had only imagined.

Level 6 Games — Auto-Scheduler

After I published Perfect Time-Based Productivity in late 2014, I planned to offer explore the help to people attempting to conquer Level 5. Fortunately, a colleague interrupted my plans by introducing me to SkedPal.

Like other auto-schedulers, it’s a program which cuts the time required to re-juggle a schedule from hours to seconds. Transforming Fast Recovery Game, it’s an AI enable programs which generates a lot of data — a first. In the future, these apps will use this data to generate an unprecedented amount of quality feedback.

As I have shown, wherever we engage in regular routines, our tendency is to create games which lead to experiences for fun and learning. With better data available, we can play more sophisticated games which leads to faster improvements.

Given the new possibilities which Level 6 opens up, I’m going to devote the third and final article in this series to games played at this level.

How Designers Can Be Helpful

Once again, just in case you missed it… this list of games is hardly complete.

For example, you may realize that none of the games I have mentioned in this article are competitive. I don’t mean to deny the existence (or power) of games that involve beating other people. It’s just that task management is primarily a solitary activity and a time demand (by definition) belongs to the individual. So the first games we need to define appear to start with one person battling the internal forces of inertia, procrastination and inefficiency.

However, it’s not hard to imagine ways to expand the games I mentioned above to include other people. Many great games start out as solo efforts, later turned into competitions by building leader-boards. As a designer, this is certainly an option.

To learn other games players enjoy that don’t fit the traditional mold, spend some time analyzing the most popular apps. If you apply gamification principles, you will find that they are heavily gamified. But I doubt that designers started out with these principles in mind. It’s more likely that innovators like Mark Zuckerberg, whose favorite games are Risk and Civilization, attempted to replicate prior experiences in some intuitive way. (Or maybe he was just lucky!)

To make great task management games that people love, arm yourself with a deep understanding. In this article, I have argued that people want to play engaging games, creating them wherever they can. If you dig deep, you can find them, unearthing the game mechanics, dynamics, and aesthetics like a modern-day archeologist or anthropologist.

The fact is, users want your help to transform their experience of task management… even if they don’t ask you for it. (Beware: They may even tell you they don’t want it!) Your job is to go deeper than superficial impressions, to analyze the job they are trying to get done so you can uncover the experience they crave.

After all, people aren’t using task management solutions idly. At all six levels, they are trying their best to fulfill their personal potential in the parts of their lives which are most important. They care. The onus is on us as members of the design community to meet them exactly where they are with the best solutions we can envision. When we do so we make a profound difference.


What other games can you see that I have not mentioned? Do share them in the comments below.

I’ll be publishing the third and final article in the series on Medium and on my website — If you are a developer/designer and would like to be notified when they become available, visit this page to sign up for updates —

If you are not a developer, you can also receive an immediate update by to downloading my article — “8 Edgy Ideas from Time Management 2.0” — at

I hope you have found my article to be useful. Please leave me a comment on Twitter — or on Medium’s Comments. I look forward to hearing your thoughts.

Thanks to Beth Avery, Jolene Brown, Brendan Bain and Suzy Wycoff for their help in editing this article.

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