Learning to Optimize Each Day’s Plan from the Controversy between Listers and Schedulers [Research]

What is the best way to track an outstanding task? Depending on your personal experience, the answer may be a simple no-brainer. What you may not know is that the technique you use puts you in the middle of an ongoing controversy. It’s a noisy battle, with opposing groups on either side.

The two extremes are represented by whom I call, “Listers” and “Schedulers”. As the names imply, Listers advocate the use of To-Do lists, while Schedulers advocate the use of calendars. Both are strong believers that people should use their preferred tool when a new task arises.

These are extreme positions because most people are just like you; they use a combination of both tools to varying degrees. In this article we’ll focus on the outliers, the purists who focus on one technique, making only a nodding glance in the direction of the other.

We’ll look at the reasons why the controversy between Listers and Schedulers exist and continues unabated. Once that’s clear, we’ll show how it can be resolved. Underneath what appears to be disparate techniques, they share the very same intent and it’s one we can learn a great deal from.

The Current Controversy

The argument between makers of lists and schedules has reached a fever pitch in online forums. (To see a list of active time management discussions, check this infographic.) At times, the debate has an almost political or religious fervor, with irreconcilable, impermeable beliefs.

The most ardent Listers argue that it’s a big mistake to place a task directly on a calendar, unless it forms part of a “hard landscape,” meaning tasks whose time cannot be changed easily. David Allen, best selling author of ‘Getting Things Done, popularized the term. According to his 2001 book, tasks that go on a calendar should only be those which are difficult to reschedule because they involve other people, such as a meeting with a team of colleagues.

Their opponents, Schedulers, argue that this approach is flawed. Instead, a new task should be placed directly on a calendar. Lists should only be used in select circumstances, like the times when we go shopping and need a tally of items for purchase. They argue, from experience, that a task with no due date is far less likely to be completed.

The few Listers who concede the point contend that just because a single task benefits from having a due date doesn’t mean the technique will work for all tasks. There is no way to turn this finding into a set of workable practices.

The anecdotal evidence supports their contention. Ordinary people experience great difficulty in managing a calendar that encompasses ALL their tasks. Some Listers go even further, predicting that the efforts of Schedulers are doomed for failure. One shouldn’t even try this technique, say a vocal few. As you may imagine, this point of view rubs ardent Schedulers the wrong way.

Where are you in all this? You may find yourself already agreeing with one side or the other, and while you aren’t an extremist, you may want to know what exactly is the best technique? Are there special circumstances in which one technique works better than another? Beyond the controversy, where does the truth actually lie?

Beyond the lack of first-hand evidence, neither side gets too much into behavioral research by experts such as Drs. Peter Gollwitzer and Key Dismukes. It’s a pity because it’s supported by colleagues like Dr. Dan Ariely, who shows that students who are given deadlines perform better than those who are not. Similar studies at NYU show an increase in completion of 40–50% by people who use due dates versus those who don’t.

These research results rely on much more than just the ability to fire up a Wordpress blog and dream up your own answers. Instead, they come from controlled experiments involving thousands of people. Unfortunately, as I said before, many bloggers and residents of chat rooms haven’t even tried both Listing and Scheduling, let alone dug into the research.

The paucity of first-hand experience, plus the ignorance of hard data may be the reason the argument has degenerated into religio-political tones. However, that doesn’t mean we should politely step away because this is a discussion that (unlike politics and religion) cannot be avoided. There is an important inescapable fact at play- human beings can’t avoid task making.

To explain why, I’ll introduce a definition I use called a “time demand,” an internal, individual commitment to complete an action in the future.

According to the research conducted at 2Time Labs, we develop our first time demands in adolescence. As teenagers, in response to our natural impulse to get more done, we create time demands in larger numbers alongside the habits required to manage them. By the time we become adults, these early habits have hardened into practices used to cope with even more obligations.

Without exception, time demands form a necessary link between our goals and future actions intended to realize them. We are the ones who own them in all cases — they lie within the segment of all tasks whose creation we control. Unlike tasks, all time demands are, by definition, generated by the individual. This isn’t true of all tasks according to our popular usage of the term “task.” We sometimes use “task” as a verb e.g. “I tasked him with completing the report.”

Given the importance of our commitments, it’s clear that the debate is really about the best way to manage time demands. As a species, we see time demands as critical to survival and success, which translates to a deep, emotional concern. In today’s world, this concern is abiding because we must manage and execute more time demands than our ancestors ever did. Their playbook, developed before the introduction of the Internet and mobile technology, is no longer relevant.

Listers and Schedulers care about the same thing — creating time demands and making sure they get completed. All of us translate this concern into plans for a day, week, and/or much longer periods of time. For many of us, this concern is born just after we wake up and start to ponder the nature of our day in terms of the time demands we need to complete. Given the constraints we live under, we hope our plan will help us complete the optimal number of time demands in the right sequence in order to call the day a success.

Why We All Make Daily Plans

We all want, without exception, to manage our time demands skillfully. Seeing them disappear into the cracks can make us feel terrible, especially if they are important. Also, being late for appointments and developing a reputation for being an unreliable flake is awful. As a result, we feel guilty when we don’t execute time demands well.

However, as we enter the adult years and our lives become more complex, the fear of failure often grows. Our list of obligations grows longer and the challenge of managing everything increases.

Managing time demands is not like managing a garden. They happen to be psychological objects, intangible creations of the mind. Each is unique, with its own level of priority and importance for a start. (In my book I identify over ten other attributes.) Our minds aren’t limited by the number of hours we have in a day.

As a result, we often create more time demands than we can complete within the constraints of 24-hour days and 168-hour weeks.

This constraint is exacerbated by the fact that we tend to be weak at estimating how long each time demand takes. This problem only worsens when time demands need to be executed in a set sequence. One small error can, in the case of an involved project, ripple out past the estimated due date, leading to disaster.

The net effect is many of us rarely accomplish our daily plans. Day-to-day success becomes a rare, fleeting experience.

That doesn’t mean we give up. Instead, we try harder to optimize our plans, even though it’s a difficult task for even a powerful computer. We only possess the computing power of our minds, as MIT PhD Cal Newport points out in his article entitled, Spend More Time Managing Your Time. Newport (a computer scientist) states, “It’s hard work figuring out how to make a productive schedule come together.” For many, the normal complications of adult living (work, family, health, community, etc.) make the job overwhelming.

A handful of people respond by not even trying. They don’t make plans and instead, float through the day doing whatever happens to strike their fancy in the moment. It’s a thrilling, freeing experience. However, most people don’t have the luxury of this approach. We must make a plan that includes picking up the kids, buying the groceries, and stopping at the mall. We dash home before the ice cream melts and the kids get too tired to do their homework.

Breaking a single step in this chain results in a problem. You probably are not the only person to pull up in your driveway only to discover our child isn’t sitting in the back seat… you forgot to pick her up.

It’s an adult problem; something that happens when we experience an increase in time demands. While we learned to mentally plan our day as teens, somewhere in adulthood the practice began to fail us, even when the stakes became appreciably higher. Here’s why.

How We Plan Our Days

According to research outlined in my book, there is no single best way to make plans comprising time demands. We are constrained to using the following four tools in our efforts to optimize our plans:

Tool 1. Our Mind, as used by Memory Users

All of us start in the same place I mentioned before. In our teens, we learn to keep a mental list of time demands with the intention to use it to help us accomplish our goals. Some continue this practice all their lives, never using any other technique.

Tool 2. A To-Do List, as used by Listers

Many people migrate to the use of a To-Do List (in either single or multiple forms.) Lists help users keep track of all time demands to be optimized. At their most basic, To-Do Lists consist of a set of actions to be performed. Some go further, tagging each action with attributes such as priority or intended location (also called a context by followers of Getting Things Done.)

Tool 3. A Paper or Digital Calendar, as used by Schedulers

A calendar makes it easy to set up an initial time-optimized schedule. It’s innate temporal design accounts for not only the action to be taken, but also its duration and intended start time. Also, it helps to preserve the time-based sequence of events if that is an important attribute. The most skillful Schedulers manage their calendars with such precision that they don’t use a To-Do List at all. They use lists sparingly — as shopping lists and checklists, for example.

Tool 4. An Auto-Scheduler, as used by Digital Optimizers

A Digital Optimizer is someone who has outsourced the creation and maintenance of their daily plan to a program that uses Artificial Intelligence (A.I.) This tool automatically produces an optimal schedule based on certain inputs. While the idea has been around for decades, recent advancements in computer power, cloud computing and calendar features have led to the invention of breakthrough products. (I am a year-long user of such a program called SkedPal, which is currently in Beta, plus a member of the Advisory Board.)

These tools are all used to produce the same end-result — an optimized, feasible plan for a day, week or month. They all reduce the “cognitive activity” that Masicampo and Baumeister reference in their work. In other words, it’s likely that a person who belongs to each user-group feels their approach works because it gives them a break from the stress of managing lots of time demands, plus some assurance their plan won’t fail. They have positive, first-hand evidence.

Is the best approach just a matter of taste?

Faithful Listers and Schedulers don’t agree. They each believe their tool of choice is not only better, but also rules out the use of alternatives. They imagine and amplify all the worst aspects of other approaches, finding it hard to imagine how someone could follow them. It’s not difficult to imagine that Digital Optimizers could also join in this kind of “My Way Is The Only Way” thinking. There’s no reason to think they’ll be immune.

How can the seeming impasse be resolved? Let’s answer the question by looking through the lens of a question: How do people in each group react to the need to re-make their plans in the middle of the day, in response to a disruption?

How Each Group Responds to Disruptions

For the average person who has made a plan for the day, reality hits when he/she is subject to their first unplanned event. It might show up as a surprise meeting, a sudden drop in motivation or energy, an emergency, or even a fresh opportunity. Let’s suppose it’s severe enough to disrupt the most carefully made plan.

We all know the best response isn’t to whine. Instead, it’s to get busy with a Plan B.

This might be obvious, but the heart of the disagreement between Listers and Schedulers surrounds what to do once a disruption becomes apparent. They react to disruptions differently.

Let’s imagine a typical disruption — a request from your boss to start on a new project “as soon as you can.” With that in the foreground, how do you respond? It depends on your preferred approach.

Like everyone else, there is a common tool you use to respond to disruptions — your mind. Picture what you do after a disruption, as you sit down to re-optimize your plan. You may set your mind to the task, cutting out all audible and visual distractions. That helps because re-balancing a disrupted calendar is tough work that can be draining with a lot of tough decisions that must be made, one after the other. As Newport says, the task requires “some serious thinking.” The tiredness that results is known as “ego depletion” or “decision fatigue.”

Before someone learns to use any kind of external tool or device, he/she starts off by storing time demands in only one place — memory. Psychologists call it “prospective memory.”

A Memory User who is confronted by a disruption starts by trying to remember the details of the mental plan created earlier. It’s a tough task, unless they have a small amount of time demands to manage. A middle school adolescent may not have a problem, but an adult’s powers of recall fade as they enter middle age.

A skillful Lister responds to the disruption by retrieving a list, rather than using memory. An ordinary list, as I mentioned before, would only include actions (and not due dates, durations or any other temporal information.)

If there were a calendar of appointments, as I discussed earlier, that would help. However, the vast majority of the basic information needed to re-make their plan (i.e. durations and planned start times) would have to come from their memory. As a result, many Listers face a hard challenge as they search for an answer on the spot, with their boss looming behind them.

Schedulers would probably react by opening up their calendar and reviewing the pre-planned sequence of time demands. They may even show their boss the current schedule. The calendar can be adjusted accordingly, moving items around until a new optimal plan is created.

Many users of paper calendars struggle, understandably, when too many changes are required. Even users of the most sophisticated digital calendars can end up hating this chore. As a result, a lot of Schedulers revert to being Listers simply because the activity becomes overwhelming.

Digital Optimizers probably have the easiest time of all. They simply enter a new time demand in their auto-scheduling program, then hit the “optimize” button. If the resulting plan isn’t immediately acceptable, they change a few parameters and run the program again, repeating the cycle until a feasible calendar emerges. For someone with a large volume of time demands and/or disruptions, this may be the only way to go. With a boss waiting impatiently, this process can be a quick “what-if” activity: an opportunity for joint problem-solving.

I can share from personal experience that none of these four approaches offers a one-size-fits-all, perfect solution. Why is that true when I have plainly stated that Digital Optimizers face the “easiest” challenge?

The picture is more nuanced than I suggested. In fact, research at 2Time Labs shows that each approach appears to be best for a particular number of time demands and disruptions, as shown in the diagram below.

If you have read Perfect Time-Based Productivity, you may recognize this diagram and notice it’s been changed dramatically. Now, it includes a new set of bubbles in the far right corner — “Auto-Optimizing.” (This is the same technique afforded by the A.I. tools used by “Digital Optimizers.”)

The thesis is simple — there is a step-function between each of the four sets of techniques. In other words, regardless of whatever tool/technique we use, there happens to be a limit to the number of time demands that can effectively be handled. Once this limit is hit, the only choice is to evolve to the next level. That involves learning the habits, practices, and rituals required to effectively use the new tool.

From experience, I can attest that it’s hard to move up the curve while trying to keep abreast of an increase in time demands. Some liken it to changing a wing on an aircraft in mid-flight.

One failure stands out: early in my career, I made the mistake of jumping back to being a Lister from a Scheduler, thinking it would yield an improvement. To my shock, it made things worse. From the diagram, you can see why. I still had the same number of time demands to manage, but now I was using a less suitable technique.

While I failed for obvious reasons, some people do need to head in the opposite direction as their time demands fall. For example, a newly retired ex-CEO or an entrepreneur who falls ill might both want to manage fewer time demands and disruptions. The right choice would be to “devolve” his/her skills and go back down the curve.

Surprisingly, they find it’s not easy either. The lesson is that it’s always difficult to change ingrained habits, regardless of whether one is moving up or down the curve.

With this distinction in mind, it’s understandable why one shouldn’t conclude that being a Digital Optimizer is best. For many people, it’s not practical.

Instead, my research shows that your “perfect” choice is a match between the volume of time demands and disruptions you must manage each day and one of the four choices of tools. As you evolve from one technique to another (in any direction) you must keep asking, “is the new investment in time, energy, and money worth it?”

Bear in mind, there’s a simple wisdom in using the simplest tool possible for the job at hand.

Perhaps it’s understandable that our preliminary survey of SkedPal Beta shows that the most successful Digital Optimizers are, in fact, former Schedulers who use digital calendars. By contrast, someone who uses their memory or a paper To-Do list has a far more difficult transition.

It’s therefore not crazy to delay an upgrade to a different technique or tool for a more appropriate time. But how do you know when the time is ripe?

Each person is different and your individual timing must be self-determined. In my book I lay out a detailed method for evaluating your current skill-set so you gain the most benefit from behavior changes that require the least effort.

You can tell whether or not you should even undertake this kind of self-examination by answering some of these questions:

- Do you find yourself unable to keep track of all your time demands?

- Have you experienced an escalation in the number of time demands or disruptions you face each day?

- Are your daily plans going unfulfilled?

- Is your peace of mind around time demands suffering?

In Summary

The ongoing controversy between Listers and Schedulers is therefore just a skirmish. It’s a distraction from the big picture. If you must deal with more time demands and distractions, you may have to contend with the limits of the approach you currently use.

In all cases, it’s never about blindly following the proclamations of Listers, Schedulers or any other group. The key action is to determine where you are now and the best pathway to a new future state. This is a decision only you can make as you match tools and techniques with your present and future needs. This self-diagnostic step is all-important and far more subtle than just following a particular school of thought and sticking with it, no matter what.

It’s best for us to be watchful and aware of the need to make changes when the time comes, while possessing a rough idea of the likely next step in our development. Then, even though the problem of managing an increasing number of time demands doesn’t go away, at least it becomes understandable and bearable.

P.S. There is some emerging evidence that a Digital Optimizer can view their plan in two ways: either as a list or a schedule. I imagine therefore that there’s a direct pathway from being a Lister to becoming a Digital Optimizer, without becoming a Scheduler first. While that has not been the path most have taken to date, the disruptive nature of Auto-Scheduling tools means that old pathways are likely to become obsolete. This is a topic I’ll be exploring in a future post. Be sure to sign up for early notification and other updates by downloading any publication from my book’s website or at 2Time Labs.

Originally published at 2timelabs.quora.com.