Step Up Your Time Management Game: How to Match Complexity with the Right Tools

It’s no secret that everyone’s time management system needs to be different—after all, we all have different lives and workflows. What works for one person simply won’t work for another.

However, many people don’t take this into account when looking for a time management tool or technique. They find a system that looks good on paper, but it doesn’t take into account the level of complexity in their lives.

In this blog post, we’ll discuss why your time management system should be as complex as your life!

Unlocking the Toolbox of Time Management: From Simple to Complex

There are two enduring myths about time management.

The first is that there’s one right way to do it.

The second is that the one right way to do it will be effective forever.

But research tells us that neither of these myths is true, because:

1) Time management works if and only if it fits your home and work environments^​1–3​

2) Time management works if and only if it fits your personal preferences^​4,5​

The reality is that your lifestyle, work environment, and personal preferences change over time. People go to college, have kids, change jobs, move to a different country, and so on.

As your life changes, so should your time management system.

So the idea that there’s a one-size-fits-all system, or even that a single system will work for you over the course of your entire life, is naive at best.

One thing that changes as your life evolves is its level of complexity.

Think about it. When we were teenagers, life was not always easy, but from a time management perspective, it was fairly simple. We had school, weekends, maybe a part-time job and extra-curricular activities—all of which could be managed with just a simple to-do list.

But when we become adults, life gets more complex. We have jobs and careers, families to manage, financials to consider, home maintenance to oversee.

To make things even more complicated, our job and lifestyle can change overnight. Maybe your new job calls for international travel, or you’re now managing a team of people.

The point is that our lives can become more or less complex over time, and our time management system needs to adjust accordingly.

In what follows, we’ll discover the three stages of time management sophistication and the tools and techniques you can use to manage each one.

Keeping it Basic: The Power of To-Do Lists for Simple Workflows

Checklists are simple, but they save lives. Literally. In The Checklist Manifesto, Atul Gawande explains how checklists are used in the medical field to reduce fatal errors^​6​.

How? Here again, complexity is key. Healthcare is becoming increasingly complex, and skipping steps can lead to severe consequences. The same is true for many industries, such as aviation and construction.

That’s why to-do lists are so powerful: they keep track of what needs to be done, systematically. This is important, because as our lives become even slightly more complex, failure and forgetfulness become costlier.

Imagine you have to remember to call your insurance provider and make sure you have the right coverage in place.

There’s nothing wrong with relying on memory for something simple like this—but if life is more complex and you need to do 10 different things related to your insurance, it becomes impossible to keep track of everything unless you use a list. And each of the 10 different things becomes a potential disaster if it’s forgotten.

I’ve said it before and I’ll say it again: the main purpose of a to-do list isn’t for you to complete everything on the list. It’s to make sure nothing slips through the cracks.

In other words, if you can’t finish everything on your to-do list, that’s totally fine. I did an entire Ph.D. on time management and, on a good day, I can only finish 80% of what’s on my list.

But the 20% I didn’t do? I either reschedule them or delete them if, on second thought, they weren’t that important. But the most important thing is to be aware of what’s done and what’s not done—that’s how you make sure nothing falls through the cracks.

Not everyone needs fancy time management tools and apps, but everyone needs a to-do list.

That’s because even if your life is relatively simple, you can still benefit from the mental clarity, peace of mind, and reliability that come with having a list.

Before we move on to the next stage, here are a few tips that can help you get the most out of your to-do list:

• Be clear, explicit, and use action verbs. “Insurance” is not a to-do item. “Call Henry from ABC Insurance to discuss coverage” is. The reason is simple: to-do lists are supposed to help you get information out of your head and into the list. If the item is too vague, you might as well have kept it in your head. Clear items help you free up cognitive resources to focus on more important things.
• Make it chronological. Constantly choosing what to do next can be overwhelming, so consider ordering your list according to when things need to be done. This will allow you to quickly decide what to do next.
• Listen to your to-do list. It’s okay to not be able to finish everything that’s on your to-do list. But if you consistently find yourself unable to finish even half of the items, that’s a sign that you need to simplify your life and scale back on commitments.

If you’re looking for particular tools, I recommend the following to-do apps:

• Todoist: Free, intuitive, easy to use, and understands natural human language (e.g., if you input “water plants, every 10 days at 7 p.m.” or “reach out to close friends every other Sunday,” it will understand).
• Keep: Free, great for quick, easily accessible lists (e.g., grocery lists), and works well with voice assistants.
• Literally any note app on Android or iOS

At this level of complexity, the tool you use doesn’t really matter. Remember: time management isn’t about making sure everything on your list gets done; it’s about avoiding mistakes, freeing up cognitive resources, and reducing stress. And with just a simple to-do list by your side, you can make sure that you don’t miss a beat.

Stepping it Up: How Combining To-Do Lists and Schedules Can Improve Your Productivity

To-do lists are a great time management tool, but they have their limits. The main weakness of to-do lists is that they don’t provide a timeline for completing tasks.

In other words, to-do lists don’t show you, visually, when things need to be done and how long they will take. They’re simply a list of tasks.

And that’s very important, because as our lives become more complex, we typically have more things to coordinate. That means, in turn, that we need to be more mindful of how much time we actually have. To-do lists aren’t particularly good for this.

Before we talk about a better approach, let’s explore a little-known fact from research in linguistics.

In most languages, including English, French, Spanish, and countless others, we use spatial words to talk about time^​7–10​. That’s why we say “a long time ago,” “pushing deadlines forward,” or “fitting something in.” The reason for this is that our brains are hardwired to think about time in spatial terms.

So if the most intuitive way for human beings to think about time is in spatial terms, then the most intuitive way for us to manage time is to visualize it.

Enter schedules and calendars.

Schedules and calendars are essentially a visual representation of what your time looks like. You can use them to block out time for specific tasks, plan ahead, and have a better sense of how much (or how little) free time you actually have.

In other words, schedules and calendars help you develop a more realistic understanding of what you can accomplish in a given day and when things need to be done. And that is the key to effective time management: thinking about time realistically.

Does that mean to-do lists are useless? Absolutely not. The trick is to combine the two approaches in a way that works best for you.

I call this the schedule mirror technique.

It simply consists in this: any event in your schedule or calendar should have a corresponding to-do list item. You’ve scheduled some time for a project tomorrow? Add it to your to-do list as well.

But wait, isn’t that redundant? Why should I have both a schedule entry and a to-do item for the same thing?

There are two simple answers.

First, people get a motivation boost from ticking items off a to-do list. You don’t get that same feeling of accomplishment from a schedule or calendar.

The second reason is more practical: to-do lists allow you to add tasks that are too small to be worth scheduling. For example, if you need to send an email in the morning, it doesn’t make sense to add it to your schedule. Watering plants, a quick call to your mom, taking out the trash, and so on; these are all tasks that can easily be added to a to-do list but don’t belong in your schedule.

Why? Remember that the most intuitive way for human beings to manage time is to visualize it. And that works fine if your schedule mostly includes events that are at least 30 minutes long. But if it’s full of short tasks, it will look cluttered and you won’t be able to get an accurate sense of how much free time you have in a day—visual clutter defeats the purpose of scheduling. (That’s also why the schedule mirror technique consists in making sure your to-do list reflects your schedule, but not the other way around).

So how can you implement this strategy? It’s quite simple.

At the end of every day, just make sure that whatever is on your schedule or calendar for the next day is also reflected on your to-do list. And if you have any small tasks that don’t belong in the schedule, add them to your list as well.

You don’t even have to do this manually. Many to-do apps, such as Todoist, now seamlessly integrate with your calendar, which means that every time you add an appointment to your calendar, it will automatically show up as a to-do list item.

Combining schedules and to-do lists can help you deal with the complexity of modern life. But if your life and work involve many projects and collaborating with other people, then you might need to take your time management game to the next level. That’s when dedicated project management platforms come in handy.

Taking Control: How Project Management Tools Can Keep You On Track

As our lives become increasingly complex, a combination of to-do lists, calendars and schedules might not be enough.

The reason is simple: if you’ve ever worked on multiple projects with different deadlines, especially in collaboration with other people, then you know the importance of having a big-picture overview of how all the moving parts fit together. And the reality is that to-do lists and schedules just aren’t designed to provide this kind of overview.

That’s where project management tools come in handy.

These tools don’t replace to-do lists and schedules–they just provide an additional layer of organization and collaboration on top of them. (By now, you’ve probably noticed that as life becomes more complex, time management tools don’t replace each other–they complement each other.).

What does this mean, exactly? It means that an effective project management tool, at the very least, should provide you with a to-do list, a schedule, and a calendar. My favorite tool is ClickUp, because it can be as complex, or as simple, as you need it to be. (Of course, you should use whatever works best for you; there are tons of relatively easy-to-use project management tools out there, such as Asana and Trello.)

But project management tools wouldn’t be very useful if all they did was provide a to-do list, calendar, and schedule.

That’s why at least three additional features I consider crucial to deal with complexity:

• Information management. One of the defining features of the modern world is how much information we’re expected to process every day. Emails, texts, social media posts, project plans, and so on—it can be overwhelming. And that’s why project management tools should provide a way to capture, store, and process all the information associated with any given project. In other words: keep track of everything in one place. Tools like OneNote and Notion already offer this kind of feature, but many project management tools also provide it as well. I’m not a big fan of using multiple tools, so I prefer using a project management platform that also provides an information management system (ClickUp’s docs, for example).
• Collaboration. Project management tools should also make it easy to collaborate with other people, in real time or asynchronously (for example, by leaving comments on tasks). Collaboration should be straightforward and efficient, so that you can get work done without having to jump through too many hoops. Importantly, project management tools should ideally have platform-agnostic collaboration, meaning that you can still collaborate on a project even if your colleagues are using different tools or platforms.
• To-do-list-per-project architecture. The thing when you have a basic to-do list is that it can quickly get cluttered and overwhelming. That’s because a basic to-do list is designed to help people navigate a fairly simple workflow. But if you have more complex workflows and projects, you can’t afford to put tasks from different projects all in one place. (For instance, if you’re juggling three different projects, it’s not a good idea to cram all their tasks onto the same list because it’ll be too difficult to track them all). Instead, project management tools allow you to dedicate one to-do list per project, so you can keep track of tasks associated with each one. And if your project management platform is any good, it should have a “cockpit” or “command center” view that lets you easily see all the to-do lists associated with your projects. That’s the big-picture view that’s so important when dealing with complexity.

I don’t actually believe that project management tools are the pinnacle of time management systems. In the years to come, I strongly expect artificial intelligence to play an increasingly important role in helping us manage our time (e.g., intelligent calendars that automatically schedule events that fit your individual preferences).

But for now, the best way to deal with complexity is by using a project management platform that offers you all the features described above. That said, don’t be afraid to experiment and find out what works best for you—everyone’s time management needs are different.

How to Transition From One System to Another

When our lives become more complex, we’re often reluctant to go into a higher gear and adopt more powerful tools. That reluctance keeps us from effectively adopting the systems we need, and leaves us stuck in a less-than-ideal situation.

There are at least two reasons for that.

Problem #1: I don’t have time to learn yet another tool

This is one of the most damaging cognitive biases in the time management game.

People focus too much on how long it will take them to learn a new tool and too little on how much time that new tool will save them in the long run.

In other words, people see time spent learning more powerful tools as a cost when, really, it’s an investment. And like all good investments, the amount of time you initially spend learning a new system is exponentially repaid back to you.

Another thing to watch out for is that we often overestimate how long it will take us to learn a new system. In reality, modern platforms are designed to be as user-friendly as possible—all you have to do is give them a try and see what works for you.

Solution: Make time to make time. That means taking the time to learn more efficient tools and techniques so that you can save yourself time in the end.

Failing to do so will only leave people stuck in a time trap: they feel pressed for time, but never invest the time necessary to break out of that time trap of their time management rut.

It’s also important to see this through an investment lens. Sure, you may have to spend an hour or two getting up to speed with a new tool, but those investments will pay off handsomely in the long run.

Problem #2: I’m afraid the new system won’t be compatible with the way I do things now

We all have a “stack,” that is, a set of tools and techniques that we use to manage our lives.

As people, we’re creatures of habit—we like the familiarity of the processes and workflows we’ve built over time. So it’s only normal for us to feel hesitant about changing our tried-and-true systems.

Solution: Try a “parallel” approach. This means that you don’t have to abandon your old system completely in order to give a new one a chance. Instead, try using both systems simultaneously and gradually transition from one to the other as you become more comfortable with the new tool or technique.

For instance, if you’re planning to switch from a “to-do list + schedule” stack to a full-fledged project management platform, take a couple of weeks of parallel usage to ease into the transition.

In practice, this could mean integrating your schedule and calendar with your project management tool, and slowly but surely transferring all of your tasks from your to-do list over to the new tool.

Conclusion: Evolving Your Time Management Is The Key to Unlocking Your Productivity Potential

A complex life doesn’t mean a complicated life. With the right time management systems, you can go from feeling overwhelmed to being in control. And that’s exactly how time management enhances mental health and wellbeing: by making people feel in control of their time^{​11–13​}

The key is to find the tool or technique that works best for you, and then adjust it as your life changes. No system is perfect—but if you take the time to customize a solution that fits your needs, you’ll be amazed at how much more reliable, productive, and stress-free you can be.

It’s time to level up your time management game and unlock your productivity potential.