The Evergreen Guide to Choosing Your Next Task Management App

Have you reached the point where you need to look for your next approach to managing your tasks?

If you have had this thought, there may be trouble on your horizon. It may mean that our current combination of task management aids (i.e. apps, habits, devices and platforms) has started to develop shortcomings. As you might have done a few times in the past, you are approaching the point where you need to make some changes. If you make the right ones, you want to arrive safely at a new level of effectiveness, and hopefully avoid having to implement another improvement for at least a few years.
But times have changed.

Today we are inundated with options: an avalanche of alternatives which are fighting for your attention. These aids range from gurus touting methodologies like GTD, to apps like Todoist or Wunderlist, to devices offering capabilities such as voice recognition to new technologies like AI and cloud computing. Some proponents even argue that your choice of platform, such as iOS vs. Android makes a difference. How do you decide which combination will make you as productive as you can be… without stressing you out?

Don’t Believe the Hype

At the very least, you probably know not to trust advertisements. You actually can’t because nowadays they send contradictory signals. On one hand there’s the app that claims to be the best. And then there’s the productivity author who argues back, saying the app you use (or device or platform) doesn’t even matter.

They do share one thing in common — a desire to get into your pocket. (As a productivity author with a material interest in an app mentioned in this article, I cop a full mea culpa!)

But you are probably past that point anyway. I’m guessing that you stopped buying into the one-size-fits-all mindset some time ago. You know people are complex and everyone is unique. There is no simple answer to the question of which combination of aids a person should use.

So how do you decide?

One obvious option is to keep reading articles promising the “Top 10 Best Task Management Apps” which cherry-pick a few choices, laying out a list of features. They use comparison shopping to help you make up your mind.
But they only provide temporary answers. Remember when we were worried about the right Blackberry to purchase? All it takes is the arrival of some new technology for the best top 10 article to be hopelessly outdated. Should you go searching for a fresh listicle every few months? Is that the best way to decide?

I offer a different approach — you won’t find a recommendation for a single app or device. Instead, I’ll give you a way to classify all task management apps by their capacity to meet your most important need: to avoid costly errors.
Then, I’ll help you determine whether or not you should even be considering a change at this time. And if you decide that you are ready to make some improvements, I’ll tell you how to figure out which upgrade is your best bet. This will help narrow your choices tremendously so you can actually start shopping around with a list of the stuff that really matters: A minimalist approach to choosing your next app.

Let’s get started by looking for some criteria that would make the choice an easy one.

The Basic Design Principles of a Sound Solution-Finder

If (like most adults) you’ve changed one of your aids before, you know that the transition to a new combination can be time consuming and while you are making the shift, life must go on. Your need to continue to manage your tasks effectively means that upgrading your system is a bit like changing a plane’s wing in mid-flight. Precarious stuff.

Perhaps what you are missing is not a specific suggestion to acquire a particular app, device, habit or platform. Even if it comes from a trusted friend you should be wary. When they inevitably change, should you? Just because you like them?

Instead, we need a framework built on enduring principles that stands the test of time, making it evergreen. Let’s call it a “solution-finder” for your next choice of apps, habits, devices and platforms.

If we were to build such a gizmo, what design principles would we use?

Principle #1 — One Ultimate Answer for All Time? It Does Not Exist
Up until not very long ago, there were some fans of different aids who would argue that their choice is the “final” answer.
For. All. Time.
Thankfully, that’s changed, mostly. Now, we can agree that the ideas in a book which hasn’t been updated in the past couple of years or an app which is not being recently refreshed probably has not kept up.
Therefore, it’s not helpful to pretend that today’s specific recommendations will be useful for more than a few months. Our solution-finder needs to be flexible, helping us not only now, but also in years to come.

Principle #2 — One Answer for Everyone Also Does Not Exist
Let’s also agree that your cup of tea might not be mine. The variation between all of us isn’t just about taste, personality or culture. A more important factor is capacity.
Case in point: the guy who refuses to write down any of his tasks anywhere but insists on relying on his memory is probably going to cause trouble everywhere he goes… unless he’s 12 years old. If he’s a knowledge worker with adult responsibilities, he’ll be a problem to himself and others.
This gives us a clue to the design of our solution-finder: under certain conditions, some approaches are just more suitable than others for “hard”, quantifiable reasons.

Principle #3 — Switching Habits is Hard
App developers have a convenient tendency to oversimplify the effort it takes to change entrenched behavior. In spite of their claims, there’s a ton of research suggesting otherwise. Also, there’s a big difference between learning a brand-new habit and changing an old one which has been around for some time. Guess which is harder?
Changing an old habit is a challenge because research shows that just about everyone who reads this article above the age of ten, already has a task management system in place. Each person has a unique combination of aids.
And, while there are helpful hints intended to implement behavior changes, there has been no huge breakthrough. Our solution-finder must take this into account.

Principle #4 — Sometimes, No Changes Are Needed
Just because it can be empirically proven that another aid is better (i.e. faster, easier to use or less expensive), doesn’t mean you should automatically switch. Instead, you may be better off saving your cognitive resources for changes which are absolutely required. This means ignoring the ones which don’t make much of a difference to you.

Here, we’ll follow the “Herbie” principle from the book “The Goal” by Eli Goldratt. His idea is that every complex system has a capacity bottleneck, so interventions made in other places don’t enhance your productivity. They are just distractions.

Also, if your overall combination of aids is working fine, there may not be a compelling reason to make a change. As you look to the future, you may decide that you aren’t likely to see a big increase in the number of tasks you must manage each day. That’s further evidence to leave well enough alone and focus on improving other parts of your life. Our solution-finder needs to be able to recommend that we maintain the status quo when appropriate.

Principle #5 — Each Choice is a Complex Blend
Every choice of task management aid brings with it other inescapable consequences. One is that your decision is part of a combination: apps + habits+ devices + platforms.

For example, when you choose to switch to a particular task management app, there are brand new behaviors which have to become habitual. Fail to learn them and your system won’t work.

Some aids may be more suitable to your needs than others, just because some apps are device and platform-specific. For example, OmniFocus is offered only on the Apple iOS platform. However, it’s one of the rare exceptions. (For the sake of simplicity, let’s assume for the rest of the article that your choice of device and platform are tied together.)

Furthermore, some methodologies require apps which offer certain features.

For example, some task management apps don’t have contextual tagging, making them hard for GTD’ers to use.

They also probably shouldn’t pick up a tool like SkedPal which is designed to help them schedule all their tasks. It explicitly breaks the GTD rule around calendar use and our solution-finder realizes this fact.

Combining These Principles into Something Useful

Our ideal solution-finder would follow all five design principles perfectly and never suggest combinations that didn’t make sense. You should be able to plug in some personal information, wait a few seconds and receive a customized answer. However, until a developer invents such software, we will have to muddle through, coaching ourselves. We simply need to be as nuanced and principled as our solution-finder would be.

To do so effectively, we have to appreciate the overall message behind the five principles. We are each on a long journey traveling on individual, slow-moving vessels. They all start from different places and have unique destinations, anchoring in any number of ports along the way, sailing at their own speed.

Logically, this means we must begin with an accurate diagnosis to determine where we are today. Once we have done so, the next steps in our journey might be more obvious. However, the difficulty of making simultaneous, combined improvements in all our aids at the same time implies that we should be conservative in our expectations, and maybe even cautious.

Thankfully, all the research around complex, personal behavior changes affirms this notion. Success comes from taking small steps. In this context, you probably shouldn’t waste too much effort trying to find “The best system in the world.”


Well, by the time you figure out your next improvement and finish making it, there will probably be a brand new “Best System in the World.” We change our aids slowly, even when we’re highly motivated. In other words, the options available to use for consideration are changing that fast.
Unfortunately, if you love quick, simple and easy answers, I have bad news. Uncovering your next improvement will take a lot of time and attention… probably more than you expect. So let’s apply a four-step shortcut we use at 2Time Labs: ETaPS.

Your First Evaluation

To begin, start your self-coaching by answering the following questions.

Question 1 — Which aids do I use?

Here is a short explanation of each aid we’ll use to complete our first step.
1. Memory — All of us start by committing tasks to memory. What percentage of your tasks today are you using memory to store?
2. Paper list or calendar — how many tasks end up being stored temporarily on paper?
3. Simple Task App — how many are kept in a simple task management app or program? They are sometimes called “Grocery List apps” due to their simplicity — examples include Google Keep and Apple iOS’s Reminders. (They don’t allow you to categorize your list.)
4. Complex Task App — if you use one of these apps (such as Todoist, Wunderlist or OmniFocus), how many tasks end up there? (The fact that you can categorize or tag tasks at will earns them a place in this category.)
5. Digital calendar — Do you use a digital calendar on Outlook, iOS or Google? How many of your tasks are placed on your calendar? (Don’t include appointments in this percentage.)
6. Auto-schedulers — if you use one of these AI driven tools, how many tasks end up here? Examples of these apps include SkedPal, Focuster, Sheldonize, TimeTo and SELFPLANNER.


Most people use a range of aids to store their incomplete tasks. In the table below, check all the ones you currently employ. Then, in the next column, enter the approximate percentage of your total tasks which sit in each location at this moment in time. (Disregard habitual tasks like brushing your teeth which don’t require cognitive resources.)


Question 2 — How many errors am I experiencing?

Let’s try to take an objective look at how many errors you currently experience. In this exercise, we’ll examine “unwanted symptoms” and how often they show up in your experience.

Here are two instruments you can use.

The Holmes-Rahe Life Stress Inventory offers an interesting way to estimate the amount of stress in your life. It offers a list of unwanted, unexpected events (such as a death in the family, or a layoff) and instructions to summarize the combined effect they have had on your life. I suggest that this metric is a proxy for the number of new tasks which have come into your world recently. As a result, you are experiencing more errors so an improvement is needed.

The second instrument is a calculator I have invented. It takes a look at your email load as well as your task burden to estimate how many unwanted symptoms are being experienced.

You can access the calculator here, on my website. Here are a few of the questions and outputs.

Some of the questions asked in the email and task calculator

If you use the calculator, either an email score of more than 50 points or a task score of greater than 150 points may indicate that the time is right for you to make an upgrade.

Question 3 — What is my current capacity?

Now that you have an idea whether you actually need an improvement in your aids, let’s look at one way to complete your quick self-evaluation.
In our work at 2Time Labs, we have trained hundreds of people to evaluate their skills in eleven “Fundamentals”: Capturing, Emptying, Tossing, Acting Now, Storing, Scheduling, Listing, Interrupting, Switching, Warning, Reviewing, and two “Executables”: Flowing and Habiting.

However, we haven’t found a way to convert this evaluation into a simple online quiz, even after several years of effort. Why not?

At the moment, it takes two days of training or 15 chapters of a book or more than ten hours of online learning to understand the Fundamentals and Executables. Furthermore, each skill is broken down into several sub-skills, as you can see in the following example showing the output from a fictional participant, Gerry.

This summary chart shows his personal evaluations in the 11 Fundamentals. Each of them is arrayed in the left column, and the evaluation is performed using our preferred method: a belt system borrowed from the martial arts ranging from a White Belt at the lowest skill to a Green Belt at the highest.

While this kind of in-depth self-analysis is beyond the scope of this article, we have noticed certain patterns from hundreds of data points collected.

One is summarized in the diagram below which shows that when it’s time for a major improvement, people follow a predictable path from one level to another.

Vector Road Infographic Design Template. Elements are layered separately in vector file.

Compared to the in-depth evaluation done in class, this diagram is a dramatic simplification which generalizes people’s actual choices.

Following the description of each level provided earlier, the basic idea is that people find themselves at six different levels. Also, they jump from one level to the next in a search for additional capacity: to reduce unwanted symptoms.

We all start by using memory (Level 1). At different times in our career, we consciously decide to change our aids and progress through the five other levels shown in the diagram. While our model has its origins in our classroom data, it’s backed up by our secondary research of academic studies.

Fortunately, it preserves a few key principles and ideas we have discussed.

One is that when people make successful changes to their aids it doesn’t happen randomly. They follow a pattern, driven by the need for more capacity.

When that need doesn’t exist, they either make no changes or stick to a single level.

Another fact our model embodies is the notion that two people experiencing the same symptoms may require different solutions.

Consider the fact that there are some illnesses whose treatment varies even though the symptoms are the same. Prostate cancer is one example which varies by age. Also, a large number of common illnesses experienced by pregnant women must be handled carefully.

In the case of task management, a similar nuance exists. Your next improvement depends not only on the unwanted symptoms you experience, but also on which level you currently occupy, from one to six.

Unfortunately, most people have never seen a map like this so they flail around. I certainly did. In the mid 2000’s, in the space of a couple of years, I unwittingly jumped down from Level 5 to Level 4 and back up to Level 5. In a desperate search for more capacity, I had no idea how to make improvements.

As you imagine, it’s also possible to skip a level in the pursuit of greater effectiveness. In the next section, I’ll explain when that might be a good idea.

Your Evergreen Guide: A Matrix of Transitions

As you take a look at the above chart, and compare it with the table you completed in Question 1, it may be easy to identify which level you occupy.
It brings us to a new question: Should I seek a higher level?
There are three possible answers to this question.
Answer #1 — No. Don’t change a thing. Your scores from the stress index and calculator are low which indicates that you have few unwanted symptoms.
Answer #2 — Make a minor change, staying at the same level. If this is your decision, you should limit your search for aids which occupy the same level. Define clearly which unwanted symptoms you are attacking. Just don’t expect a major increase in your ability to manage more tasks.
Answer #3 — Make a jump to a higher level. If this is your choice, fasten your seatbelts.

As I mentioned before, each of the jumps to a higher level is not the same. In fact, here’s a matrix of the changes you can make from one level to the next reflecting the difficulty of the upgrade. The darker the color, the harder the improvement.

As you can see, there are a few anomalies.

For example, if you are Level 4 it’s easier to skip Level 5 and go directly to Level 6. The invention of new auto-schedulers which occupy the highest level are specifically designed to help you manage all your tasks in your calendar. They are much easier to use than a stand-alone digital calendar.
But for the most part, the standard recommendation is to make your improvements one level at a time. There are critical skills to be learned along the way, so someone who tries to jump to Level 6 from Level 1 is likely to bump into a steep learning curve. They might have the right app and the most expensive device, but the required change in habits would probably lead to failure.

So… take a moment to identify your current and next level.

Next Steps

Based on your self-coaching, at this point you should have completed the first step of ETaPS: Evaluate. Let’s complete the second: Target.

Now, you must set precise goals around the aids to be included at the next level.

Habits: As I mentioned before, these are the most difficult to implement. Start here with the kind of in-depth analysis I described above and base your new habits on the behaviors that are most limiting — the bottlenecks.

Apps: Do a search for software that fits the next level. As you do so, determine the choice of device and platform which makes sense. Be prepared to go with decisions which are practical, rather than optimal, because of the limitations of current-day apps.

Once you have determined your improvement, you have defined the target behaviors you want to implement. Here are the next two steps.
· Plan your improvement by breaking the target down into small steps spread over time. Then, set a final due date.
· Support your changes with more assistance than you think you need. We routinely under-estimate the duration and difficulty of these changes and don’t build in enough support. For example, schedule recurring reinforcements in your calendar.

These steps will set you on a personal improvement path that is all yours. Now, when you come across a new app, book, device or tip, take a deep breath. As attractive as it may be, where does it sit within the 6 Levels? What are the assumptions embedded in its design? And finally, does it fit in with your personal improvement path?

Your success only comes when improvements which apply to your needs have been implemented. Until then, you must manage your path carefully, as if it is powerful but fragile.

Further Help

Be prepared… one day there will be a Level 7 and it just might be the right one for you. As such, you need to be ready for the journey from one level to the next to be ongoing, and to be multifaceted. In other words, you may want to keep looking out for fresh combinations of aids at the next level.

Your biggest asset in your journey is your own self-coaching. Using the steps I have outlined, your approach will be evergreen, independent of any particular app, habit, device or platform.

But this is just a start.

If you want some assistance in making smaller changes based on the comprehensive, in-depth analysis I have described, here are three suggestions. Use the contents of my book, Perfect Time-Based Productivity. It’s based on the same principles as my elearning program, MyTimeDesign Plus+ and live training, NewHabits Foundations.

If you happen to be one of the few people at Level 4 looking to make the transition to a higher level, consider taking my specialized online training. It’s called A Course in Scheduling and it’s best completed after the completion of one of the prior training courses.

To follow the progress of the ideas described in this Evergreen Guide, follow 2Time Labs on Twitter, or search for #scienceoftimemanagement.

If the ideas I have shared can be improved in any way, let me know! If you read the past stories I have written here on Medium you will see how they have evolved over the past few years.

I hope to hear about your journey and wish you all the best as you make your next choice of app, habit, device and platform.

If you found this post to be valuable, it would mean a lot to me and others associated with 2Time Labs if you could click on the “applause” icon below. It would help encourage us to keep going!

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