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Part IV How To Maintain A Well-Oiled To-Do List System

Your master task list, context lists, and daily to-do lists are components of a broader system. Their effectiveness depends on that system’s integrity.

If you have a well-oiled system in place, your lists will help you to get important work done faster and with more efficiency. If your system is faulty, your lists can actually hurt your workflow, sabotage your time management, and demolish your productivity.

In the following sections, I’ll show you, step by step, how to maintain an effective to-do list system. Most of these tips build upon core concepts we’ve already covered in previous sections. A few introduce new concepts. All of them are essential to creating a system that guarantees your to-do lists help you to get your important work done. Tip #1: Keep A “Tiny Task” Batch List

I mentioned the use of a batch list in Step #5 of the section How To Create The Perfect To-Do List. The purpose of a batch list is to organize all of your tiny tasks in one place. Tiny tasks are items that take less than 10 minutes to complete. The idea is to batch them together and address them during a single work session.

Tiny tasks don’t belong on your daily to-do list. Remember, your daily list should be limited to seven items. Save the space for high-value tasks that require more time to complete (a minimum of 15 minutes).

Nor should tiny tasks remain on your master list. They’ll just end up cluttering it.

Instead, place them on a separate batch list. When you have extra time, choose a few to work on. Cross the items off your list as you complete them.

Following are examples of tiny tasks that belong on a separate batch list:

Make the bed Start a load of laundry Email client Record yesterday’s sales data Empty the dishwasher Schedule a meeting with coworker Make a dinner reservation Check voicemail Take out the trash Update the boss on an ongoing project Return a phone call Declutter your workstation Pay bills online Update software

Each of these tasks can be completed in a few minutes. The problem is, when you address them sporadically throughout your day, you risk them becoming distractions. They’ll interrupt your workflow, derailing your momentum and destroying your creativity. They’ll tempt you to multitask, which will introduce task switching costs. Switching costs negatively impact your performance and cause your productivity to plummet.

The solution is simple. Batch these tiny tasks together. Set aside 30 to 45 minutes to work on them. This will allow you to focus on the items, one by one, without distracting you from your important work. You’ll have set aside a separate work session to address them.

Whenever possible, batch together tasks that are related by context. For example, if you need to return several emails, treat each one as a separate to-do item and handle all of them during a single batch session. Likewise, if you need to do several chores at home, batch them together and address them at the same time.

Working on related to-do items minimizes switching costs. As a result, you’ll get more done in less time and make fewer errors along the way. Tip #2: Remain Vigilant Against Feeling Overwhelmed

One of the biggest threats to any task management system is the feeling of overwhelm.

You’ve no doubt experienced it at some point. For example, you’ve checked your email and become discouraged after seeing hundreds of messages sitting in your inbox. You’ve looked at your master to-do list and become disheartened by its length and lack of task-level context. You’ve looked at your daily to-do list and become demoralized after discovering the items you’ve included are vague projects rather than actionable tasks.

The good news is that you can eliminate - or at least minimize - these problems by implementing the steps we covered in the section How To Create The Perfect To-Do List. A solid to-do list system will help you to efficiently manage your workload.

But the threat of feeling overwhelmed will always be present. If it gains a foothold in your mind, it will siphon your enthusiasm, extinguish your motivation, and block your creativity.

For these reasons, it’s imperative that you remain vigilant against it. You must always be on your guard. Circumstances will conspire to make you feel overloaded with work. For example, your boss may foist more and more responsibilities onto your shoulders. Your coworkers might attempt to delegate their to-do items to you. Your spouse may add to your growing list of obligations without realizing that you lack the bandwidth to handle them in a timely manner.

Your to-do lists will help you in this regard. Assuming you’re creating lists as described in the section How To Create The Perfect To-Do List, you’ll be able to gauge your availability and take on new tasks - or deflect them - accordingly.

Don’t underestimate the demotivating power of feeling overwhelmed. It will raise your stress levels, make you more susceptible to distractions, and prevent you from getting important stuff done. Tip #3: Define Your To-Do Lists By Context

We’ve covered this concept in detail already. But it bears repeating as we explore how to create and maintain an effective to-do list system.

In Step #6 of the section How To Create The Perfect To-Do List, I mentioned that every task on your master list should be accompanied by contextual details. For example, you should specify the project with which the task is associated; the type of activity (analytical, creative, etc.); and whether there are any location-based constraints attached to it.

Noting these details may, at first, seem like a waste of time. But they’re crucial to sustaining a smoothly-operating to-do list system. When you add context to the tasks on your master list, you can quickly identify the ones you should work on.

For example, suppose you’re responsible for a high-priority project that has a looming deadline. You would focus on the tasks that move that project forward (project-based context).

Or suppose it’s mid-afternoon and your energy levels are low. You’d do well to focus on mindless work (e.g. data entry, decluttering your desk, etc.) rather than analytical or creative work (activity-based context).

Or suppose you’re at the office. You would focus on to-do items that can only be done there (location-based context).

Task-level context informs your decisions regarding what you should do next. While providing contextual details upfront takes time, doing so streamlines the decision-making process later. It’s a good investment.

I recommended earlier that you maintain multiple lists by context. This is an approach that works for me. I suspect it will work for you as long as you apply it with consistency. Tip #4: Conduct Weekly Reviews

Weekly reviews are critical. They make the difference between a system that motivates you to get important stuff done and one that encourages you to procrastinate. They determine whether you successfully keep track of everything you need to do or let items fall through the cracks.

Most people neglect to conduct regularly-scheduled reviews. They think them unnecessary. They assume they have a solid grasp of their workload, and thus formal reviews would be a waste of time.

This may indeed be the case for you. Suppose your master list has fewer than a dozen items on it. You can probably keep track of everything without conducting weekly reviews.

But chances are, you have far more than a dozen tasks to monitor. If you have any responsibilities or goals at all, your master list is sure to grow past the point of being manageable without periodic review sessions. Count on it.

Imagine that your to-do list has more than 100 items on it. Without periodic reviews, you won’t be able to accurately gauge your progress on them. Nor will you be able to mentally organize them according to context. It’s too much to keep track of.

This is the purpose of holding a weekly review session. It gives you an opportunity to evaluate the extent of your progress toward your various goals. It also gives you a chance to reprioritize tasks as needed.

I conduct my weekly reviews on Sunday evenings. You should choose a day and time that accommodates your circumstances. Note that you’ll need to focus. So, set aside 45 minutes during which you can work undisturbed.

How do you conduct a weekly review? Here are the basic steps:

Gather all of your to-do lists. This includes your master list and context-based lists. Do a brain dump of all the tasks and projects floating around your head. Add them to your master list. Break down new projects into individual tasks. Separate new tasks according to context (project, type, and location). Create new context-based lists, if necessary. Clear out your email inbox. Send responses if they’re necessary. If an email requires you to take action, but isn’t urgent, make a note of it on your master to-do list and archive the message. Also, archive emails that don’t warrant a response or action, but may be needed later. Delete the rest. Review your master list and context-based lists. Purge tasks that are no longer necessary or important. Note the tasks that are both important and urgent. Mark them as candidates for your daily to-do list. Note the tasks for which you’re waiting on input from others. Write down the person’s name and the date you expect to receive his or her input. The date will tell you when to follow up if you don’t receive it. Review your current deadlines for high-value tasks. Make adjustments if necessary. Assign deadlines to new tasks you’ve added to your master list and context-based lists. Review your calendar for the coming week. Create your daily to-do list based on your availability.

The above may seem like a lot of work. In truth, it is. But it’s a good investment. A weekly review is integral to maintaining a well-oiled to-do list system. It will ensure you focus your limited time on the high-value items that will move forward the work that is most important to you. Tip #5: Update Your List Of Goals

Your goals dictate how you spend your time. They give you clarity about what you want to achieve, in the short run as well as years down the road.

They make you accountable. When you know what you’re trying to achieve, you become aware that every decision you make either moves you closer toward your goals or further away from them.

Goals also help you to focus on what’s important. In Step #2 of the section How To Create The Perfect To-Do List, I recommended assigning a specific goal to each task on your list. The purpose of doing so is to give yourself an incentive to act. When you know the reason a particular task needs to be done, and the reason is consistent with something you want to accomplish, you’ll develop laser-sharp focus on the task. You’ll treat it as a priority.

First, create goals that are specific. Most people’s goals are vague. That’s a problem because, without specifics, it’s difficult to gauge one’s progress toward achieving them.

Take a look at the following example.

Vague goal: retire early.

Specific goal: retire by your 60th birthday with $2 million in liquid investments and a $5,000 monthly income.

Note how the vague version makes it nearly impossible to track your progress. There’s no way to tell how close you are to achieving it because you haven’t clearly defined the metrics by which you gauge success.

In contrast, the specific version provides trackable metrics.

Second, write down your goals. You’ll be less likely to abandon them.

In 1979, graduates of Harvard’s MBA program were asked whether they wrote down their goals. Eighty-four percent admitted they had no specific goals; thirteen percent claimed they had goals, but had not written them down; three percent wrote down their goals along with their plans to achieve them.

In 1989, the interviewers followed up with the graduates. They noted two remarkable findings. First, the 13% who had goals earned more than the 84% who had no goals. Second, the 3% who wrote down their goals earned 10 times as much as the 97% who did not write them down.

You can see there’s power in committing your goals to paper.

To recap, you’ve created goals that are specific. And you’ve written them down.

Now what?

The third step is to review them monthly. Set aside 30 minutes at the end of each month to track your progress and reevaluate whether any of your goals have changed. If they have, make notes accordingly.

Your to-do list system is driven by the things you want to accomplish in your life. Some of your goals will be short-term in nature - for example, you might want to earn a promotion at work this year. Others will be long-term in nature - for example, retiring by the age of 60 with $2 million in liquid investments.

Review and update your goals each month. Doing so will help keep your to-do list system running smoothly. Tip #6: Avoid Getting Bogged Down In Methodology

It’s common for people interested in being more productive and learning how to better manage their time to try numerous systems. We discussed some of those systems as they relate specifically to to-do lists in the section 10 Most Popular To-Do List Systems. When we broaden the spectrum to include systems related to time management in general, we encounter the Pomodoro Technique, timeboxing, the Franklin-Covey system, Zen To Done, and others.

Trying different systems is important. It’s the only way to determine which ones complement the way you work. It’s also a great way to discover individual tactics you can include in your own approach.

This is essentially what we’ve done in this action guide; we explored several of the top to-do list methodologies with an eye for the features that seem to hold the most value. We then created a to-do list system using some of those features.

But there’s a dark side to productivity and time management systems: it’s easy to get bogged down in them. We become so focused on the methodologies created to help us manage our time that they begin to negatively impact our productivity. This is a version of the problem we discussed in the section The Productivity Paradox: How Your To-Do Lists Are Hampering Your Success. The systems designed to help us end up holding us back.

The purpose of any productivity system, including your to-do list system, is to help you get the right things done on time. The goal is to increase your efficiency and ultimately make your life easier to manage.

When you focus on methodologies to the point that they become the priority, you risk forfeiting these goals.

You probably know someone who fits this description. She adopts every new time management system she comes across. Or she uses a system that is so complex and requires so much time to maintain that it ends up hampering her productivity. (To see examples, visit YouTube and search for “time management binder systems.”)

Your to-do list system is there to support you. It’s there to help you get the important stuff done and move you closer to your goals. It’s not there to rule your life.

Don’t become so bogged down in the methodology that you forget its purpose. Be open to modifying aspects of your to-do list system as your needs change. Be willing to adopt new features as you discover better, more efficient, ways of doing things.

Just remember your to-do list system is there to aid you, not control you. Tip #7: Build And Follow A System That Works For YOU

There is no perfect to-do list system. The approach that works for others may not work as well for you. This is a point I’ve stressed throughout this action guide.

While the basic building blocks of an effective system - e.g. deadlines, task-level context, and separation of current and future tasks - have universal value, other aspects are less crucial. They can be modified or swapped out for others.

In fact, you should modify or swap them out if doing so improves your ability to get things done.

The aim of this action guide is not to force you to work within the constraints of a single system. On the contrary, its aim is to help you to create a system that works for you.

Note our progress thus far…

We discussed the most popular to-do list strategies used today, highlighting their best features. We also covered the fundamentals of effective lists, all of which are vital to creating a successful system. And we’re now discussing the core features of a solid support structure that will ensure your system works smoothly over the long run.

The concepts we’ve covered have had a single goal: to help you create your personal to-do list system, a methodology that works for you. Your approach is going to look different than my approach. That’s as it should be. Our circumstances are different. Our work processes are different. Our predilections and proclivities are different.

It follows that our respective to-do list systems will be different.

It’s worth repeating that the basic building blocks, covered in the section How To Create The Perfect To-Do List, are the same. They’re essential to creating an effective system. But your application of them will differ from mine.

The most important thing is that your approach complements your workflow and circumstances. Tip #8: Be Consistent

Your to-do list system will only be as effective as the consistency with which you apply the principles we’ve discussed in this action guide. Consistency is the key to success in any endeavor, and maintaining a successful task management system is no exception.

It’s one thing to know how to create effective to-do lists. It’s another thing entirely to apply the basics on a daily basis. Doing the latter will mean the difference between a smoothly-operating system and one that eventually overwhelms you.

The challenge is twofold. First, consistency requires habit change. Left to our own devices, most of us are inclined to give ourselves too much latitude. We need to build the habit of taking action on a regular basis. It doesn’t come naturally to us.

The second challenge is that skipping a day or two can have a snowball effect. Once you skip a day, it becomes easier to skip forthcoming days.

You can probably relate to this from experience. Ever notice how postponing an unpleasant activity - for example, visiting the dentist - makes it easier to postpone that activity again and again? The same thing can happen if you fail to apply the steps and tips explained in this action guide with consistency.

If you struggle with being consistent, I recommend you use the “Jerry Seinfeld” strategy. Here’s how it works (I’ll explain its history in a moment):

First, learn the 10 steps to creating an effective to-do list system. (These steps were explained in detail in the section titled How To Create The Perfect To-Do List.)

Second, memorize the eight tips for ensuring your system runs smoothly over the long run. (These eight tips are found in the current section titled How to Maintain A Well-Oiled To-Do List System.)

Third, buy a wall calendar that displays the entire year on a single sheet. Also, buy a red pen.

Lastly, apply the steps and tips you’ve learned to your master list, context-based lists, and daily to-do lists each day. After you’ve successfully done so, cross the day off with the red pen.

Seinfeld used this strategy when he was on the comedy club circuit. He would write jokes each day, crossing the day off on his calendar. The red “X” marks eventually formed a chain, which he made certain to never break. Seinfeld credited this “chain” strategy, which encouraged him to write consistently, to becoming a skilled comedian.

Until you develop the habit of consistent execution, try Seinfeld’s approach. I used it to train myself to exercise. It worked perfectly. I’d be willing to bet you’ll have similar success using it to maintain your to-do list system. What To Do If You Fall Off The Wagon

In the previous section, I noted that you must be consistent with your to-do list system if you want it to be effective. The problem is, being consistent, day after day, is difficult. It’s tempting to let things slip here and there.

Unfortunately, letting things slip can quickly lead to a spiral of decline. Before you know it, your system has crumbled and you’re trying to dig yourself out from under it.

This is more common than you might imagine. Many people fall off the productivity wagon. They let their systems collapse around them, even though doing so carries a considerable cost.

Why does this happen? It happens because any productivity system, whether it’s focused on task management or workflow efficiency, is a series of learned behaviors. Keeping it running smoothly requires developing new habits and applying them with consistency. It takes commitment and resilience.

Expect to face challenges as you work to keep your to-do list system running smoothly. There will be times when you feel like throwing in the towel. That’s understandable. Replacing bad habits with good ones is tough work.

The key is what you choose to do when you stumble.

Some people give up. They figure it’s too difficult to maintain their to-do list systems, and point to their failure to successfully keep them going as evidence. With a defeatist attitude, they let their systems crumble and surrender to the consequences.

Others take the opposite approach. They acknowledge that perfection is a pipe dream. A delusion. They expect to stumble occasionally. Instead of giving up, however, they forgive themselves and get back in the proverbial saddle.

I encourage you to take this latter approach if, or when, you stumble. Don’t beat yourself up; self-guilt has no value. Instead, brush the dust off and forgive yourself.

Then, try to determine the reason you stumbled. Was it a lack of clarity regarding some aspect of your to-do list system? Was it a lack of energy that induced you to neglect your weekly reviews? Are you trying to do too much given the limited amount of time at your disposal?

Once you know the reason (or reasons) for your slip-up, you can make changes to correct the underlying problem.

A properly-developed and consistently-executed to-do list system will improve your productivity as well as your quality of life. You’ll experience less stress and enjoy more free time to connect with those whom you love. You’ll also enjoy more freedom to pursue personal interests.

But it’s important to realize you’ll encounter challenges. What you do in the face of these challenges will determine whether your system does its job over the long run.