What Designers of Task Management Apps Can Do to Catch Up with Pokemon Go

Why aren’t task management apps as popular as Pokemon Go? If it’s true that every single functioning adult on the planet manages their tasks using a method of some kind, why hasn’t at least one app achieved the popularity of a game which recently hit 25 million users per day?

After all, completing tasks is far more important than catching Pokémon, visiting Pokéstops, and doing gym battles. We all hate it when we don’t get stuff done, even if the task is only a fun one, like catching Pikachu.

The easy answer would be to blame users’ superficial need for fun.

But how can designers of task management apps make their programs more engaging? Are there practical answers to this question that would make a difference?

In this article, we start by stepping away from bits, bytes, and interface designs in order to focus on behaviors. Doing so helps us clearly distinguish the games people play as they take the journey from novice to expert in task execution. Armed with this deeper understanding, perhaps there is a way designers could enhance the user experience. Maybe they could make it more game-like, engaging and fun.

If that were to happen, perhaps fewer newbies would abandon task management apps such as Todoist, Wunderlist and Google Tasks because they fail to have a meaningful “Ah-Ha” moment — a clear experience of the product’s benefit.

To answer these questions we’ll tap into two impulses each person has with respect to apps they download: 1) an intention for it to make a material difference and 2) a hope that the experience might be interesting and even fun. To reach these twin goals, we’ll bring together two schools of thought: one developed at Harvard Business School (HBS) and the other originating in computer gaming.

Two Schools: Innovation Meets Gamification

The first school of thought originates from HBS Professor Clay Christiansen. He’s an expert in disruptive innovation and helped create the idea that a customer needs to be seen as “someone who is trying to get a job done.” He discourages companies from focusing too much on features and benefits of their software, products, and services.

Instead, they should help users improve the way they try to do their core jobs. See them as “hiring” solutions for short-term purposes, he says. John Dubbin explains the principle in an article entitled: “For what job would you hire a milkshake?” We rephrase the question to suit our purpose and ask: “For what job would you hire a task management app?”

The second school of thought is that the best solutions to customer problems are, by definition, gamified. In other words, they offer a deeply engaging , entertaining experience in which customers’ actions are clearly linked to obvious feedback. This response encourages more actions, setting up a compelling cycle which is hard to break.

A properly gamified system has the following core attributes which support this cycle:
- Objective goals
- Easy to comprehend score-sheets
- Feedback mechanisms
- Autonomy to make choices
- Coaching

Most effectively gamified systems start by strengthening and building the individual’s intrinsic motivation, rather than rushing into the popular game elements which have been so popularized: Points, Badges and Leader-boards (PBL’s.) These boost extrinsic motivators: helpful, but they are not essential.

As we merge the ideas from HBS and gamification into one, we can imagine that users who are trying to get a particular job done start by hiring a task management method or app. They continue to use it if they have an engaging experience. But that’s not all.

Unlike board or computer games, task management apps serve a higher purpose than mere entertainment. They exist in a context where the stakes are high. Poor task management is a precursor to failure in all practical aspects of life, bar none, acting as a powerful antidote to life’s randomness. Pay attention to this skill and the door swings open to a fulfilling job, well-being, beneficial relationships, and career.

So task management is a job and a game at the same time. People who use them are users and players. We know from the design of engaging video games that they also include a Players’ Journey — the movement from one level of skill to another. If task management also happens to include a journey, what are its stages and when does it start and end?

The User/Player Journey

Most online gamers are familiar with the idea of the Player’s Journey. This growth from lower to higher levels is marked by measurable shows of achievement, the addition of special powers and a capacity to learn and execute new skills. Well-designed games keep players hooked by making this journey clear, along with the milestones needed to get to the next level.

My research at 2Time Labs shows that there is actually an organic journey that all customers of task management apps embark on when they are children. The journey’s job and game-like nature remain hidden from most: as we illuminate the pathway in this article, keep this in mind. Today, neither user/players nor designers are aware of its existence. With that in mind, let’s look at the genesis of this journey starting when we are children.

As kids, we learn the concept of time from other people at around the age of eight or nine. It sets the stage for an event which happens a few years later: the creation of our first “time demand”, one of the psychological objects we bring into being as we mature. Each time demand is defined as an “internal, individual commitment to complete an action in the future”. It’s the kind of task we assign to ourselves for completion — a self-made promise.

Given the absolute importance of time demands to a successful life, we continue to create them as long as we retain the mental capacity to do so. Furthermore, from the moment we realize their value, we engage in a relentless drive to generate more.

This sets up a lifetime struggle. As the number of time demands we create continues to increase, we look for new ways to accomplish them. We come to see this increased capacity as crucial to the accomplishment of bigger goals.

The experience of creating more personal capacity in order to get more done may be a familiar experience. Anyone who has played computer online games like Diner Dash may recognize a similarity. (Ironically, it belongs to a genre of entertaining apps called “time management games”.)

In this particular game you play the role of the manager of a diner. The simulation feeds your customers in a continuous, increasing flow. Your job is to keep up with higher volumes by changing your tactics for assigning them to tables, taking orders, serving meals and collecting payment. With each round, and level, the task becomes more difficult.

It’s a very popular genre, with lots of similarities to real life, with just a few exceptions. One is that these games have a clear end — you can “win” by serving the last customer at the highest level. In real-life, there is no end-point… you can play the game of managing time demands until you arrive at death’s door.

Another difference is that the game is the sole source of customers and tasks. In a given round, it decides how many to send you. In real life, however, you are the source of your time demands. Plus, your mind isn’t as considerate… it doesn’t naturally stop creating more time demands than you can handle. This reality pushes many into feelings of overwhelm.

The final difference is that there is no “final level” other than the end of the game in Diner Dash. That’s the very opposite of real life. My research shows there are people who are happy and productive at all levels of the player’s journey involved in managing time demands. (It’s backed up by research showing that approximately half of all employees report that they have enough time to get everything done.)

They don’t have a problem because they resist the urge to create more time demands, striking up a perfect balance in which little changes. As a result, there’s no need to up-level. In fact, some actually down-level when they reach retirement, a fact I point out in my book, Perfect Time-Based Productivity.

But one key similarity with Diner Dash is that in the beginning, improvements come easily. In the six levels I will now describe, the gains also become progressively more difficult to accomplish.

Level 1 — Memory

In the beginning, as young adolescents, we teach ourselves to remember time demands. After all, each one originates in the mind so it’s only natural that we would store them for later retrieval in our internal memory bank which psychologists call “prospective memory.”

This works well when there are only a few things to remember. However, as our goals grow in size and number, they call for the creation, management and completion of more time demands. Then, we have a problem. Some of them start slipping through the cracks… to our consternation. This is the first time we face this problem, but it’s one that features at every level. It can be distressing, especially if we believe that it’s a problem we had already dealt with a long time ago.

I have met a few adults who never confront the problem, attempting to rely on memory for the rest of their lives. If they are illiterate or have a disability, it might be the only method they ever use. More often than not, they simply lack role models.

However, most professionals teach themselves a new technique and progress to Level 2 or 3.

Level 2 — Paper

Most of us who are Baby Boomers, Gen X and Gen Y’ers migrated from the memory usage of Level 1 to the use of written To-Do Lists (i.e. paper) of the next level. However, many of today’s adolescents probably skip the use of paper altogether and go straight to the next level, which involves the use of a digital task manager.

Level 3 — Simple Task App

Often, the first tool we pick up to replace a paper To-Do List is just a digital version of the same tool we have been using. It offers a few more conveniences but essentially bears the same basic features.

If we add more time demands, our lists become too long to manage in this way. We look for a substitute. Noticing the power of more complex apps, we make a switch. (Examples of both Simple and Complex Apps can be found in this article https://zapier.com/blog/best-todo-list-apps/.)

Level 4 — Complex Task App

At this level, complex task apps enable us to manage long lists by allowing us to add important information to each task. There are many choices, but the typical user only chooses one or two attributes.

Some prefer location-based information (i.e. contexts) like @home or @computer, as promoted by the popular book, Getting Things Done. Others prefer to use the Eisenhower/Covey Matrix in which we use two attributes — priority and urgency. A third much smaller group employs temporal information such as a due date or duration.

Apps in this category provide varying degrees of flexibility in their choice of attribute, but the underlying fact is that a time demand is an intricate creation with a long list of potential attributes.

Today, we have a few hundred apps to choose from. They are ubiquitous and inexpensive, often sharing the same core features. On many tablets, laptops, smartphones and watches, either a simple or complex task app comes pre-installed. Most are available in some form for free.

However, sometimes these apps are just not enough. Many of us who show Type A behavior continue the game of creating more time demands and bump into a predictable limit: we run out of time.

Even if a Complex App allows us the ability to place tasks on a calendar, that technique eventually falls short. The problem isn’t one of placement. The fact is that each day, week, month and year is limited in duration and anyone who attempts to schedule tasks in a calendar must account for their available time. It’s the only way to avoid obvious errors of over-commitment and coordination.

For a while, most of us who approach this point compensate by trying hard to manage a mental calendar of tasks and appointments. Doing so helps us say “No” when we need to, plus make realistic promises and set reliable due dates. When an unexpected disruption occurs, we mentally re-juggle this calendar, but this task becomes harder to accomplish as more time demands are added.

Actually, truth be told, this mental calendar has been our companion all along, at all three lower levels. It just didn’t come into the foreground because, up until now, we had enough spare time to recover from errors. Now, the high volume of time demands takes away this buffer. We have less free time, and the shortcomings of this particular practice become obvious. We become stressed.

We start to wonder… what would it be like to replace this mental calendar with its digital counterpart? What if we used Outlook, Google or a smartphone to schedule more than just appointments? These questions push us to consider an upgrade.

Level 5 — Calendar of All Tasks

Once we tell ourselves that there should be a way to successfully manage all of our time demands in a calendar system, we are contemplating “Total Task Scheduling.” In its purest form, this skill eschews the use of a To-Do List, only relying on a calendar of tasks. (In fact, a calendar is just an enhanced To-Do List, but for the purposes of this article, let’s keep them separate.)

Those of us who actually attempt this technique experience a rude surprise.

We discover that it takes a monumental effort to convert all our commitments into a feasible schedule. It’s a manual, tedious process that involves a large number of variables. Putting it together for the first time can be exhausting.

However, there is a comfort that comes from observing our first complete result. It represents an optimal plan — one that takes into account everything that needs to be done in a single, visually clear place. There are no overlaps. Or conflicts. Nothing is left out. It’s much easier to juggle tasks and appointments. Its very existence is more likely to produce a better outcome than a mental calendar ever did.

Unfortunately, that happy feeling is often short-lived. Depending on our work environment, the first disruption occurs within hours or even minutes, rendering our carefully crafted schedule obsolete. Now, we must react.

Should we immediately update the entire calendar? Or wait until the following day? Or week? After all, changing a single due-date or appointment can produce a multi-day ripple effect that can take a long time to re-juggle... the better part of a day, in fact.

Even if there are no disruptions, the following morning brings inevitable decay: the whole calendar must be updated with tasks which are new, completed or deleted. All this overhead adds up so that many of us quit Total Task Scheduling after only a few days. A large number correctly foresee the difficult nature of the challenge and don’t even try.

However, there are a tiny few who figure out the intricate habits required. They reap the benefits but must make a considerable investment in perfecting new behaviors.

When I published my book, I thought that this was the end of the journey and so may you. Fortunately, I was wrong. Like others, I found Total Task Scheduling to be a huge challenge and even though I had implemented it to some degree, I was ecstatic when a new level emerged.

Level 6 — Auto-Scheduler of All Tasks

Apps such as SkedPal Beta (which I use daily and also do work for), Timeful (which was acquired by Google in 2015) and others are some of the tools used to reach this level. They are all designed to automatically juggle your schedule using Narrow Artificial Intelligence. With robot-like precision, they produce an optimized schedule within seconds.

Since making the switch about a year ago, I have been able to handle far more time demands than ever before. It’s a new experience — so new that the third article in this series will focus exclusively on Level 6 games.


I’m hopeful that, over time, there will be new levels. But for now, these six represent the entire journey we take in our efforts to improve our task management capacity. As you can see, as users we “hire” very different tools for each level of the journey. It’s the only way to get the job done. When we detect that our current methods are failing, we go looking for a new level, without even being aware of their existence.

I certainly did so when I found myself struggling after I moved from Florida to Kingston, Jamaica. I simply could not keep up. After reading a convincing testimonial from a proponent of Level 4, I changed my daily practices.

Unfortunately, things became dramatically worse. Within a few months, I re-adopted my old practices.

Now, in retrospect, you may understand why. With absolutely no knowledge of the six levels, I unwittingly started at Level 5, switched to Level 4 and then went back to Level 5. A wild goose chase.

But it’s not uncommon. When players aren’t aware of the six levels, they make these mistakes. And they are not alone. Bloggers also make the error of urging readers to follow their personal example. So do gurus who imagine that their personal level is the ultimate, final, perfect one that can be attained.

These are well-meaning people who are sincerely trying to help others but fail to do enough.

What about designers? What happens when they don’t understand the six levels? What products get developed if the movement from one level to the next is obscured in the minds of users and those who design task management apps?

How This Knowledge Can Help Developers

When any professional who helps people cope with time demands doesn’t understand the entire journey, things can become difficult.

For example, there are psychologists who are devoted to helping people improve prospective memory without the use of “prosthetic devices” i.e. task management apps and paper lists. Without an understanding of the entire journey, they cut their clients off from a useful source of help.

Also, designers of paper planners who only understand a single level also get stuck, to their detriment. They probably face a shrinking market, even though some of the advertising I have read tries to convince the public otherwise.

They aren’t alone. Much of the marketing content I have read for tools, apps and devices implies that the task management solution being advertised is the final answer: the ultimate one-size-fits-all tool for users trying to get a job done.

A better approach is to understand actual user/player motivation and behavior. Charles Duhigg, author of Smarter Faster Better, was recently quoted in a Fast Company article entitled “Why the Most Productive People Constantly Change Their Methods.” In describing them he said: “Constantly cycling through systems forces (them) to think about (their) own productivity.”

In light of what we know about the 6 levels, his observations make sense. The most savvy users are always preparing themselves for the next upgrade. However, the people he describes aren’t, for the most part, doing so for idle reasons. Instead, they are trying to get a job done that is essential to their life working. They have surrendered to the fact that any solution they select is subject to psychological and technological pressures.

A full discussion about our innate drive to achieve more is beyond the scope of this article, and so are the reasons why some of us show Type A traits, while others do not.

At the same time we are all subject to the cumulative changes driven by technology. A rapid expansion in social networking and the mobile internet provide us with an incessant link to triggers for new time demands. They are intentionally engineered to capture our attention, and keep it.

Beyond these factors, there is a simple truth. It feels good to get high-quality stuff done: we like to create time demands and to complete them. Lots of them. In the extreme, it’s Type A behavior, as I mentioned before: they are the ones who probably scale the six levels faster than their colleagues. If this were a competition, Type A’s might be the ones trying hardest to win.

In fact, there is something game-like taking place around these six levels. A designer who understands these inner dynamics should have an advantage in making task management apps more like a popular game. Here is the method they could use.

Designing for Game-Play

During the course of this article, I have hinted at a single game everyone plays that spans all six levels. For simplicity’s sake, let’s call it “The Time Demand Capacity Game.”

As we explore this multi-level game, you can probably come up with other games which are naturally being played. These will be the subject of my next article in the series, but for now, let’s apply each of the five core attributes of a gamified system introduced earlier to this example and see where it falls short.

  1. The goal of the Time Demand Capacity Game is to match the volume of time demands a player wants to complete with the appropriate personal capacity. This, in turn, is defined by a conscious choice of practices and tools.
  2. Unfortunately, a real score-sheet does not exist that indicates how well we are doing. All we have to use are a blend of intuition and gut feelings. We know something feels wrong, for example, when time demands start falling through the cracks. When other unwanted symptoms show up we start looking for answers. They include lateness, falling behind email, not spending enough time on relationships, experiencing a work-life imbalance, missing due dates, not entering the flow state/deep work and suffering from a ruined reputation. A good score-sheet would send us an alert when these problems started happening.
  3. To make things worse, the feedback mechanisms are haphazard. When the symptoms mentioned before start happening, they show up in drips and drabs, making them easy to ignore. It’s easy to misinterpret them, believing they are either coincidental or caused by random factors.
  4. Fortunately, in this game, most players have the autonomy to choose their own level. Few companies impose the use of task management tools, leaving the user to up-level as needed.
  5. There is very little coaching available in playing the Time Demand Capacity Game. Most coaches, authors or trainers use a “follow my example” approach, leading users to get stuck at their preferred level.

So in summary, this overarching game which covers all six levels is, today, a difficult one to play well. For most people, The Time Demand Capacity Game is hidden from view. Key elements are missing. As a result, it’s often played badly as you may recall from my wild goose chase from Levels 5 to 4, then back to 5.

To my knowledge, there isn’t any task management software that helps a user understand these levels. In fact, current designs actually hinder users’ game play. Instead, how can designers help?

They can start by doing the following:

  • Educate user/players on the entire journey they are on. This would build loyalty.
  • Help their users move on to the next level when the time is right. By anticipating user/players’ needs, they can add new features from the next level. Some paper planner companies, for example, are digitizing their solutions.
  • Reach out to players at lower levels who are ready to upgrade, helping them see the early warning signs.

These three steps require a willingness to discover the job users are trying to get done. As you can see from our discussion, this approach can be used in depth, in order to yield sound insights. Unfortunately, the distinct impression I have is that many companies in this space are fixated on their competitors at their level. The result is that few stand out and none are particularly engaging.

My belief is that the first company which teaches its user/players to see all six levels and their place within it will benefit from a new degree of loyalty. Also, it may spur the design of the first “all level task management app” which would rely on a wide-ranging understanding of the user/player’s needs. If it were successful, a user who enters the app’s ecosystem may never leave. Plus, they would have a reason to invite other people, regardless of their perceived level.

On the flip side, companies which ignore these levels will suffer from an unhappy phenomenon. They may be unwittingly encouraging their user/players to look elsewhere for solutions, reflecting the behavior that Duhigg described. Furthermore, those which only focus on making improvements to their current solutions may be doing themselves a disservice. They may be encouraging the user/player to add more time demands even faster. As we have discovered, doing so can lead them to look for a solution at the next level, shortening their usage of the current product.

Should app designers encourage user/players to “graduate” to the next level if it’s one they don’t currently serve? I think this is a strategic decision you and your company need to make, with all its pros and cons. However, I know how lost I felt when I went on my wild goose chase. If there were an app that helped me understand my dilemma, I would be very grateful.

A company that was serious about helping user/players see the entire game might help them track the number of tasks being successfully completed as a fraction of all tasks. If that number is falling, it may be a sign that it’s time for the player to move on to the next level. That would be an awesome indicator.

Richard Branson is quoted as saying: “Fun is being on top of things.”

While he is probably talking about the feeling that comes from winning the “Time Demand Capacity Game,” there is another positive experience we have when we contemplate a move to the next level. In that moment, our hopes are raised. A new possibility beckons which inspires us to put up with the pain of learning new habits and adapting ourselves to new tools.

A company that attaches itself to this moment is one that will earn a reputation for putting the needs of its user/players first. Initially, it may not be the most profitable approach, but it’s one which would be uniquely memorable because it lines up so well with the job the user/player is trying to get done.

Imagine, there are millions of dollars being spent today on secret and hidden information in digital computer games. Perhaps people would appreciate a few insights into the task management games they play every day. Could an app offer information that transforms the user experience?

My Next Two Articles

This definition of the “Time Demand Capacity Game” is just a start. In my next article, I’ll show that there are other games afoot, some of which I can see. Several of them will probably look familiar to the average professional, but the article should help designers gamify their current solutions.

The third and final article in the series will focus exclusively on Level 6. It’s the newest and the most intricate level, with knowledge that is fast emerging, so it will be the most challenging.

While I haven’t focused much on the fun people experience when they play these games, I don’t mean to leave it out. While these are called “serious games” which have a real purpose they can be as much fun as any other game because the outcomes are so meaningful.

If we put our heads together, we can do a lot to help people navigate the task management that’s required to reach complex goals. It just takes a certain willingness to see the jobs users are trying to do, so we can appreciate the games they are already playing. If you can already see some of these games, please share them in the comments below.


I’ll be publishing the upcoming articles on Medium and on my website — http://2time-sys.com. If you are a developer/designer and would like to be notified when they become available, visit this page to sign up for updates — http://www.2time-sys.com/application-designers/

If you aren’t a developer, you can also receive an immediate update by registering to download my article — “8 Edgy Ideas from Time Management 2.0” — at http://www.2time-sys.com/special-report-8/ .

I hope you have found my article to be useful. Please leave me a comment on Twitter - http://twitter.com/fwade or on Medium’s comments below. Last thing… make sure to Follow this publication. I look forward to hearing your thoughts.


Thanks to my team of editors who helped with this article: Monisha Longacre, Estee Solomon Gray, Dale Pilgrim-Wade, Misha Maksin, Brendan Bain, Marcia Oxley, Doug Toft, Arlene Henry, Joyce Kristjansson, Paul Mittendorf