To-do list survival guide

Gerben Oostra
14 min readApr 23, 2021

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Getting more and more responsibilities results in different kind of tasks, full agenda’s and less time to focus. As I explained in the Skill Stack, being effective and efficient is a foundational behavioral competency. In this guide I combine some best practices from GTD, Habits, Time-Blocking, and Calendar management to improve your efficiency and effectiveness.

A lot has been written on task management. Everyone seems to highlight one aspect and presents it as a silver bullet. I prefer to pick the best aspects and mix and match for my personal preferences. In this guide I’ll show what that entails for me. Then you can focus on the aspects that resonate most with you. With your own system in place, you automate your process. You can then spend your energy on the actual work.

The 3 aspects of task management

Task management always seems easy, but ends up being either complicated, or even fails completely. That’s because general task management tries to solve three different problems. While some methods focus on one, you need a solution to each of them to become effective. The three challenges are:

  • Having an overview of tasks (ie, not forgetting tasks)
  • Selecting tasks to execute (ie, prioritization)
  • Creating situations (time and focus) to execute tasks (ie, execution)

You need an overview of tasks to not forget things. When the number of tasks on your list increases, the risk of forgetting items increases. Especially if tasks aren’t relevant now, but have to be done at some point. Like sending a birthday card, which you can’t do a month too early. The simplest overview is one big list, ideally prioritized. The complexity lies in the variety of tasks. Tasks have different sizes, some have due dates or deadlines, and some require certain context or situations.

Knowing what to do is one thing. At some moment you need to select tasks to execute. Will you just go down your to-do list by order? Ideally you would. Some tasks are actually part of projects, with it’s own prioritization. Some tasks are small and easy, some require long focus periods. The challenge in selecting tasks to execute, lies in matching the task urgency with execution readiness. For example, a non-urgent email can be sent between two meetings, but painting your house can’t.

This brings us to the third aspect in task management: creating situations to actually execute your tasks. Just following your prioritized list can result in a lot of context switching and inefficiency. You can improve your throughput of tasks by grouping similar tasks, for example all your groceries items or all e-mails you need to send. Other tasks require long focus periods, which you need to create in your day schedule. The main challenge is thus to create execution readiness for all of your tasks in your day schedule.

3 approaches to task management

You’ll probably have your own preferred way of organizing your week. In talking with other people and reading books and blog posts about personal efficiency, I see a few recurring approaches. These all address the previous three challenges (task overview, task selection, and situation creation) in their own way. I try to mix these to combine their benefits. When my efficiency drops, it is usually because I’m ignoring one of these themes. The three main ingredients to task management are:

  • Task lists
  • Habits
  • Time blocking
Three main ingredients to task management. Image by author.

Task lists

This is the most logical one, that also seems the most simple. Just keep a list of all the things you have to do. This gives you an overview of all your upcoming tasks. The biggest challenge is to keep the list clean and clear.

Dividing tasks across time and projects. Image by author.

Some advocate one big prioritized list of all tasks. However, many tasks are actually related. They are part of a bigger project, resembling a sequence of tasks to do. Besides these task dependencies, you’ll also have tasks that you shouldn’t forget, but can’t yet do. For example extending your phone subscription. Or following up on a task you delegated to someone. In my task management I divide my tasks in current vs. future, and individual vs. projects.

With a lot of separate lists it’s difficult to see what actually is the first thing to do. Therefore I also create a separate list for the week. This gives me a clear summary of what I want to achieve this week. Don’t make this a list of what you might do, as that’s already in your other lists. Really make this the top few items.

Habits

Habits are actions you repeatedly and frequently take. For example going for a run three times a week, starting the day at office with responding to emails, or taking a walk after lunch. These actions vary from your general task list. You indeed shouldn’t forget them, but as soon as you’ve done them, the next instance appears. They are a special kind of actions. By making these repetitive actions habitual, you can do them with less effort.

Until habits have become really habitual, you need to put effort into them. For me there are two things that help. One is to track how successful I am in performing the habit. This gives me feedback on my progress and I challenge myself to keep the streak going. The second is to make my intent explicit and plan it in my day or week. This prepares me mentally to actually do it. Then during the day, it’s a task I plan somewhere, instead of relying on it just happening.

It is commonly said that it takes three months for a habit to build. My experience is that there are a few stages in my mindset. I start with enthusiasm, expecting some benefit, and happy to add some new variety in my schedule. As soon as the newness wears off, motivation drops, and I more often skip the habit. I usually need to taper a bit down, for example going for 2 runs a week instead of 4. Or meditating 3 times a week instead of 7 times. If I find that new sustainable baseline, I can maintain my habit quite long. But even then, I need to deliberately chose a moment in the day or week to make it happen.

Suppose I want to go out for a walk after lunch every afternoon. That intention first needs to be clear. Then on each working day, I prepare to have a walk after lunch. Its (almost) at the top of my mind, I look forward to it, and I take it into account when scheduling other events during the day.

Another example: suppose I want to build a habit to go out jogging twice a week. Every week, I think ahead which two days are best for running. I again prepare to keep time available for jogging on those days. Other events can intervene, but then I just adjust my plans to still meet two days.

This ‘flexible agenda’ is probably something you already do in your mind, with events and tasks that aren’t in your calendar or task list. But instead of keeping a ‘I should really go outside today’ in your mind, make it a bit more concrete and change it into ‘I’ll go out for a walk after lunch’.

Time blocking

Time blocking is assigning periods of your day to certain group of tasks. For example an hour of ‘email’. In that hour, you’ll send emails, send reminders, and follow up on replies: a lot of small tasks. Another example is to spend two hours of focus time writing a draft proposal. Just one task, which requires a continuous block of attention and focus.

Without time blocking you have the risk of allowing small tasks or meetings to interrupt the attention and focus required for bigger tasks. The result would be a busy day, with many to-do’s done, but no big results. The small tasks are spread around the day and week, and your bigger projects are divided in fractions, which are spread around the day.

The alternative is to first plan your bigger chunks and try to group the smaller tasks together. I now have the following process. At the beginning of the week, I define a few ‘big topics’ I want to make progress on. Each one requires a lot of hours, ideally in bigger chunks. I assign those to the days of the week. Here I take into account the available time (outside meetings) in my calendar. I tend to assign them mainly on Monday-Wednesday, at most one both in the morning and afternoon. This allows spillover to Thursday and Friday. Experience has taught me that new (often urgent and small) tasks will arrive, just as ad-hoc meetings. Thus first a rough sketch of the week.

Rough sketch of the week. Image by author.
Each day, a just-in-time more detailed view. Image by author.

On each day, I draft (with pencil) a sketch of my day. The meetings I have, the blocks of focus time for my bigger projects, some smaller blocks for ‘doing small tasks’, some calls I have to make, the after lunch walk, and the jogging session.

Improving your task management

Goal setting

The previous time blocking forces you to first assign the bigger blocks, to ensure that they get done. This is assuming you know which things are important to work on. Goal setting is about prioritizing the important (non-urgent) tasks. What bigger things do you want to achieve? What will you focus on in this period?

The Eisenhower matrix, source.

Setting goals has two benefits. Firstly, it ensures you keep the target in mind while doing tasks. This improves ad-hoc task prioritization, preventing getting lost in rabbit holes. Second, it ensures you think about what you find really important. Tasks can be divided between urgent vs non-urgent and important vs non-important tasks. The resulting quadrants are known as the Eisenhower matrix. Thinking about goals, focuses your mind on the Important row.

If you’re really goal oriented, you can define year goals, quarterly goals, monthly goals and then weekly goals. Related goals can be seen as milestones of a project. These projects are nice containers for all your tasks, moving towards your milestones. Each goal is input to your weekly time blocking, ensuring you spend time on those goals. Within those time blocks, you can then work on the most important tasks.

For me those long-term goals are too artificial, usually not realistic, and feel a bit enforced. I prefer to think about themes. I can have a theme to be more active, with associated target of jogging three times a week. Another theme can be a side project. It has no deadline, the more time spent the better, but it still needs to be on the top of my mind. These themes are topics, or projects, where I can move forward and make progress. When planning my week, I use goals or milestones, to focus my attention on the right things.

Besides themes there are also spinning plates. Projects, or initiatives, where I don’t really have to individually contribute. I do however need to keep an eye on the progress, reach out to people, and communicate a lot.

Thus I have high-level overarching themes. On a day-to-day basis, I have projects with upcoming goals/milestones. There are also initiatives I am associated with, but not as an active participant. These I regard spinning plates, which I frequently check to discover tasks I can do to.

How about a calendar?

The most commonly used tool to schedule time is probably your calendar. I only use my calendar for appointments. Events that have to happen at a certain moment, often because other people are involved.

You could use your calendar for your full week and day planning. I’ve tried to do this in my digital calendar. That forced me to be too explicit and precise, which took too much time. Whenever I needed to adjust, I either didn’t adjust my digital calendar, or I spent too much time fiddling around with the task-appointments. However, this is highly personal. I know people who do utilize their digital calendar for this. The main advantage is that other people can see that you’re not available because of important work.

I don’t use a digital calendar for time-blocking, because for me it’s key that my day detail schedule is flexible. Therefore I use pencil on paper, to easily move things around. Urgent important meeting arrives in the morning? Focus block is moved to afternoon and I relocate some smaller blocks to fill up the time around the meeting.

I also don’t use a digital calendar for habits. If I’m going out for a walk after lunch, or read emails in the beginning of the day, they don’t have a really fixed precise moment. I intend to do them somewhere in the day, but the suitable moment depends on the day.

I also don’t use a digital calendar for the last item: to-do items. An approach to ensure you get tasks done, is to create a calendar item for each task you commit to doing. You then add these to your digital calendar, filling up the weeks to come. It works for some people, but for me it felt like Tetris. Every meeting that is to be planned, required all my to-do items to move around. As they usually are prioritized, adding one meeting required the full list of subsequent tasks to be moved. This doesn’t scale really well. Next to playing Tetris, I’m also really bad in estimating the required time. This meant that every block was never the right size. Adjusting all the other blocks to this was too much of a chore to me.

I do however create (with pencil) a draft schedule for the day. This captures my intent and plan for the day, while I can still easily adapt it to new events as it progresses.

Resulting system

I’ve so far covered to-do lists, habits, time-blocking, and goals. Let me dive a bit deeper in how this works together.

To-do list

The first main aspect is on curating your to-do list. As mentioned before, I group related tasks in projects. If a project is big enough, it can get it’s own separate list. I also select tasks to do in a certain week, leaving all other tasks for the future. This results in the following flow. It might look a bit complex, but it works actually quite simple. In short, select tasks to do for this week, while keeping all other tasks stashed away in lists:

Flow of tasks. Projects are sources of tasks, some tasks are delayed indefinitely or till a certain moment. In this case future tasks are divided into remaining tasks (Future Tasks) and task with specific return date (Not relevant yet). Image by author.

With a few separate lists, it’s easier to prioritize tasks (the second challenge).

The week plan

The third challenge is to enable execution. Here we create a rough week & day plan, ensuring that our habits get a place and that we spend time on our important goals. Thus we specify our intent and create our plans accordingly:

Tasks, Goals, Habits combined into a rough week planning and flexible day plan. Image by author.

Tools

The most important thing is to develop your own system. System trumps tools. However, tools can be beneficiary. I’ll shortly cover the tools I use, as I often get questions about it. But other similar tools might suit you better.

I use Asana for task management. I’ve created projects for each list (Future tasks, current projects, specific projects and future projects). Selection for the week is done by assigning tasks to myself, resulting in a clean ‘My tasks’ view. The ‘My tasks’ view consists of a section ‘Today’ which holds my top prio tasks to do asap. The other tasks for the week are in the ‘Upcoming’ section. Tasks that become relevant at a certain date are in the ‘Later’ section, all with a due-date.

I use boomerang to improve my email habits. I only get emails in my Gmail account at 9:30, 13:00 and 16h (with an exception for emails from my manager). If I send an email of which I expect a response, I mark the email to be put back in my inbox if I don’t get a reply. If anyone says ‘I’ll come back within a week’, I’ll never forget to remind that person a week later. These are thus not in my asana lists.

My reading material also deserves its own list, for which I use Pocket. If I find something interesting which takes more than a few minutes to read, I add it there. Then I reserve some ‘reading blocks’ in my agenda of the week to read whatever is on the list. It’s also great for commuting or unexpected waiting time. Much better than mindlessly scrolling some social media feed.

To plan my week & day I first used my A5 sized paper notebook. Recently I’ve switched to an erasable Bambook, but there are more erasable notebooks out there.

Books I want to read are all in Amazon wish lists (by category). Recently I’ve been moving to Goodreads, where I also select a few books for the next year or so.

Take it easy

This system might seem a bit over optimized, and perhaps it is. The advantage is that if you are able to operate with such efficiency, you can also slightly let go of the process while still maintaining sufficient efficiency. By going a bit too far for a short period of time, allows you to take it a bit easy, without losing too much efficiency. This does require to go all in for a short while. Learn your personal system. Then relax a little bit.

Also think about why you want to become efficient and effective. For me, it is about getting al the chores done as easy as possible, such that I can spend more time and focus on the interesting parts. It’s similar to a software engineer automating all repetitive tasks. As that should result in more time for novel challenges, instead of just being able to do more mundane tasks.

Resources

The idea’s here originate from a few sources:

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