3 Ways to Improve Your Task Management As a System vs. a Collection

Francis Wade
2Time Labs
Published in
10 min readMay 21, 2021

Why experienced productivity enthusiasts need systems thinking and self-diagnosis to make further improvements

Pete is stumped. He’s read all the important books and attended many classes on productive task management. Like most folks, he found them helpful in the beginning. As he became aware of practices such as capturing tasks, adding them to lists and scheduling them in his calendar, his excitement grew!

Now, much later, he appreciates the value of these early lessons and even uses a task management app. However, recent life changes in the last two months have left him confused.

First, his company finally promoted him to the role of staff supervisor, a week before his wife gave birth to twins. All of a sudden, the number of tasks in his app spiked upwards. Now, he feels as if he’s been taken back to the past.

Feelings of overwhelm he hasn’t had in years have crept in. He’s behind on several projects, and can’t remember the last time he exercised. His family tells him he seems stressed. And his new direct reports have started making jokes about his poor memory; a few important tasks slipped by, causing them to laugh, but not forget.

He’s gone back to read and re-read the advice from some of his favorite gurus but they just aren’t helping like they used to. Now, he spends precious time on Reddit, Quora and Medium, while clicking on advertisements for shiny new apps.

What IS going on? What should Pete do?

His situation isn’t all that peculiar: most of the help in task management focuses on assisting beginners. As newbies, they reap a lot, making spectacular gains. Some become instant productivity nerds. However, more experienced people like Pete don’t gain from such introductory principles. These basic lessons have already been absorbed into their regular routines.

What he’s experiencing is similar to what happens when a trainee car mechanic is confronted with a problem on a high-end motor vehicle. While he can solve the most common problems on an average, lower-end automobile, he has his limits. There comes a point where he must gain deeper diagnostic skills and use a computer if he wants to work on complicated, expensive vehicles.

Like a trainee mechanic, Pete can’t benefit any longer from basic lessons. He longs for the thrill of non-stop insights, but few can explain exactly what’s going on with him at this later stage. The gurus aren’t helpful, as they merely repeat their core messages intended for first-timers.

Therefore, he is unable to understand his situation, let alone the tools he needs. In this article we’ll address the missing element in his mental schema: that in task management, scale matters.

Why Task Management Presents Unique Scaling Problems

Most people like Pete who progress beyond the basic level soon discover that there is no such thing as a one-size-fits-all solution. In other words, no single app or set of detailed practices work for everybody. But the question that gets rarely asked is “Why?”

At 2Time Labs we have isolated the cause from other culprits such as style, personality or culture: it’s task volume, and how it grows. To understand why, let’s start by looking at this particular problem we all face, and how we attempt to solve it.

We human beings have a headache on our hands with regard to future tasks. These are “psychological objects” which, unlike our physical creations, don’t persist in the way we want. Without constant vigilance, they simply disappear.

We make this unconscious discovery in adolescence. Disappointment when tasks disappear from our attention leads us to cobble together bits and pieces into a makeshift system: the only way to get the job done. We wind up with ad hoc combinations of personal memory, paper, digital apps, other people, and routine behaviors. The result is an individual, custom mélange, uninformed by any training. Unlike Pete, most folks don’t ever take classes, read books, or hire coaches, and use these teenage methods well into retirement.

It’s unfortunate. With some exposure, they’d be just as excited as Pete was. Plus, they’d enjoy the luck beginners have, when almost everything they try seems to help. It’s no wonder. When you begin with a self-made system in any discipline, a little expert guidance goes a long way.

However, that initial thrill would wear off, as usual, due to increased task volume. Why? The law of diminishing returns in task management steps in. Simply put, the more tasks you can manage effectively, the harder it is to realize further gains. Not that this is unusual: in most fields of human endeavor, the amount of energy required to make improvements at advanced levels only increases.

What most don’t realize is that this law is compounded by another shared human tendency.

Slightly Type-A individuals (like Pete) fall in love with task management upgrades for a reason. They become productivity nerds because they yearn to complete more tasks, projects and objectives. So as fast as they gain more capacity, they use it up. Just witness the number of motivated CEO’s who race in marathons and Ironman triathlons in their “spare” hours.

Unfortunately, their ambition often isn’t appreciated by others. Most productivity experts have little advice for these impatient but high-performing individuals. Few venture into their world to direct their hunger for more task capacity.

Therefore, when diminishing returns are combined with Type-A Tendencies, perplexity ensues. People like Pete find themselves in a tricky spot. Where should he begin?

The best approach is to stay close to home: to examine his current practices with a fresh lens. But that’s easier said that done — it’s not as easy as picking up a blood-pressure monitor at the pharmacy. Instead, he requires a fresh mental model.

How Are Tasks Manipulated?

Like a trainee car mechanic, Pete needs to move from perceiving a collection of components to using a “whole-system-at-once” approach. To illustrate, before the first day of automobile class, a beginner may know how to measure:

- gas in the tank.

- coolant overflow.

- tire inflation.

- oil levels.

- battery strength.

This is enough component knowledge to fix the most basic issues on simple vehicles. However, if our trainee were to deal with complex problems, he’d need to understand the sub-systems: engine, fuel, ignition, transmission, electrical, cooling, lubrication and chassis. Each of these are designed to interact with, and support, each other. Even worse, hard-to-solve problems impact multiple sub-systems simultaneously, making a diagnosis difficult.

Clearly, knowing cars are created as a system (vs. a motley collection) gives a mechanic the power to effect sophisticated diagnoses and repairs. He can now take a “whole-system-at-once” approach to his repairs because he is using a better point of view, or lens.

In like manner, Pete needs to see his current setup differently (i.e. as a system), by adopting a new mental model of task management. For example, in the beginning, he was taught three separate core practices you may recognize:

- capturing a task on paper instead of personal memory.

- deciding and assigning a captured task to a schedule or list.

- executing tasks on his list/schedule.

While this model is sufficient for a beginner, today he needs a new one. Without it, he lacks the ability to do something magical: take the overwhelm, lateness, life-balance, stress and memory problems he’s having and diagnose them. To tackle these symptoms, he requires some advanced knowledge, just like the trainee mechanic. To highlight some of what he’s missing, let’s draw three analogies to describe the “whole-system-at-once” lens he needs.

1. Appreciating System-Wide Operations

In terms of the bigger picture, Pete was never taught that his task management comprises an interconnected system. To him, it’s like the modern pentathlon: a collection of separate disciplines. (The Olympic event includes fencing, freestyle swimming, equestrian show jumping and pistol shooting.)

Instead, he needs to think like a swimmer who discovers that every single movement in the water is connected to all the others. They work together (or against each other) to affect (or retard) forward motion. And, they are all occurring at the same time.

With this appreciation, he could understand a common dilemma. Performing the three core practices he was taught each day is not enough to solve his problems. Neither is an effort to improve them separately. If he’s not managing how they interact as a whole-system-at-once, he could even make things worse by optimizing the wrong practices.

2. Performing System-Wide Diagnostics

If you have long passed the beginner stages of task management, you may be like Pete: your task volume has also surpassed low levels. You also face a future of hard-fought gains.

Now, you need an ability to diagnose your system as a whole, in order to pinpoint improvements or repairs.

Remember that trainee mechanic? If a car won’t start, he’d only be able to predict the most obvious causes…including some wrong ones. With a whole-system-at-once understanding, he could learn how to do an end-to-end diagnostic, followed by a precise intervention. This is exactly what you may need.

Let’s take another look at the symptoms Pete’s experiencing: overwhelm, lateness, life-balance, stress and memory problems. While some would advise him to cut his task volume by refusing the promotion, leaving his job or hiring a nanny, these would only work for a while, if at all. Eventually, his appetite for managing more tasks would re-create the original problem. And so might yours. Perhaps you share a human tendency to use up new capacity as soon as it appears.

A superior approach would be to find ways to continually increase your capacity: the total number of future tasks you can effectively manage. Here are three steps you (and Pete) should take which use a whole-system-at-once approach.

First, he needs to use a better mental model. For example, the one used here at 2Time Labs encompasses 13 practices: Flowing, Habiting, Capturing, Emptying, Tossing, Acting Now, Storing, Scheduling, Listing, Switching, Interrupting, Warning and Reviewing. While this is an expansion on the 3 core practices Pete learned, its greater precision allows for the higher quality diagnoses in my book and online assessment training.

Second, he must learn that the three core practices he was “taught” are actually used unconsciously by all functioning adults. (So are the 13 practices used at 2Time Labs.) As such, his learning was really a discovery of practices he was already doing, but did not realize.

The researched fact is, we humans teach ourselves task management, usually with no instruction. This self-taught feature means that most of us possess uneven skills which have never been diagnosed. Therefore, they have never been contrasted with best-in-class performance in a rigorous way so we have no idea where we stand.

Third, when we come to grips with our end-to-end system, we can inject some magic and rid ourselves of symptoms like Pete’s. While each of the 13 practices can be improved in isolation, they are not all made equal. For example, changing the tires on your car has no effect on getting it to start when it won’t. In task management, specific problems warrant special diagnoses. These produce Pareto Improvements: small efforts which result in big upgrades.

Once Pete has taken these steps, he can concentrate his attention on specific improvement areas. However, he also needs to understand where the analogy breaks down: why changing a core practice is not like replacing a tire on his car.

3. Psychological vs. Physical Systems

Can Pete outsource changes to his task management system? After all, he prefers to drop his car off rather than tinker with it himself, especially when new parts are needed.

But tasks are not physical objects, like cars. By definition, these psychological objects originate in the mind, not in the material world. So do the processes to manage them.

Case in point: as we saw, most adult don’t update their teenage methods, even when errors start appearing. They simply don’t trace these problems to its source: the fact that their new task volume overwhelms their (once effective) practices.

At this point they need to wean themselves off all mental reminders. However, most focus on the tangible or digital replacements: diaries, paper lists, apps and devices.

They mistakenly overlook the fact that this is primarily a psychological transformation in which the elements work together differently than physical and digital objects. This fact alone makes diagnosis and Pareto Improvements challenging.

Can an Expert Help With Pete’s Transformation?

In specific circumstances, for short periods of time: “Yes”. But what happens the next time he has a spike in task volume? Will he be prepared to make changes on his own?

The truth is, Pete remains the ultimate owner of his system of psychological objects and processes. He’ll use it every day until he can’t, due to the eventual loss of his faculties at an older age.

Therefore, it’s far better for him to develop the skill of making his own improvements than to be dependent on experts. In this context, the advice of others may be somewhat useful for a limited time. But this is not like leaving his car at the mechanic’s shop for repairs.

Instead, he must become a great diagnostician and implementer. Some additional skills he will need to master include filtering outside recommendations. When others suggest that he adopt a new behavior, paper planner, task management app or virtual assistant, he shouldn’t react hastily. On the contrary, he should return to his self-diagnosis, and see if these ideas make a difference.

It’s the only way to tackle the unwanted symptoms he’s facing.

Fortunately, Pete is not alone, and neither are you. The most experienced, productive professionals see themselves as the instigators of their growth. Like them, he should use great diagnoses to look for Pareto Improvements while developing his nascent whole-system-at-once lens.

Summary

The good news is that help is coming. Only a few years ago, it was unthinkable that the everyday car mechanic would use on-board scanners and computers.

In the same way, we can expect to see whole-system-at-once diagnostic tools emerge which help us pinpoint the best changes to our task management systems. That means we’ll react better to unwanted symptoms which pop up. Instead of frantic searches, we’ll have specific, personal plans that cover several months.

We’ll finally be able to relax, and spend time focused on the Pareto Improvements we need to make next. Unlike the Petes of the world, we won’t be distracted by bright, shiny improvement “opportunities” which aren’t relevant to us. Instead, the thrill of making continuous changes which make a difference will return.

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For more information on the MyTimeDesign Rapid Assessment based on “whole-system-at-once” thinking click here

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Francis Wade
2Time Labs

Productivity/Strategy - Founder of 2Time Labs and author of Perfect Time-Based Productivity. Also