Definition of a to-do list: A long list of tasks whose primary purpose is to overwhelm you into numbing inaction.

A typical to-do list is literally just a dump of everything that’s on our minds on any given day. What we usually think of as our to-do list is actually just a ‘capture’ list.

A typical to-do list may be a good place to capture everything you need to get done. But it is a bad place to actually start getting this stuff done.

Why does a to-do list make you less productive?

Well, there are a number of reasons.

First, a long list can overwhelm you, leading to decision fatigue and procrastination. The pressure to complete every item induces stress and anxiety. Especially as you’re coming up to the end of your day and you realise you’ve barely even begun on your list.

Second, items in a to-do list can be too vague and not actionable enough. This can make it difficult to know where to even start or even how to prioritize your tasks.

A typical to-do list prioritizes quantity over quality, encouraging checking off tasks quickly and creating a sense of false productivity. This can result in a lack of focus on truly important tasks.

Planned vs unplanned tasks

Most days we end up working on unplanned tasks that weren’t even on our list. While this unplanned work may be urgent and even important, it increases our sense of frustration because it keeps us from working on what was already on our list.

On the other hand, rigidly following a list can hinder flexibility and adaptability to changing schedules, priorities or unexpected opportunities. This tension between planned and unplanned work can lead to frustration and a feeling of being out of control.

To-do lists lack context

Ultimately, to-do lists lack context. We could have everything from grocery shopping reminders to completing a work presentation on the same list. When you look at a to-do list that includes tasks from across the spectrum of all areas of your work and life, almost everything seems important, making it impossible to effectively prioritise.

Given all these issues with typical to-do lists, what should you do?

Firstly, we just need to accept that on any given day we’re going to work on stuff that we’ve planned to work on, and we’re going to work on stuff that shows up on that day. We’ll rarely ever get to knock off all items on any given day and that’s ok. In fact, it’s good to not try and check everything off, and keep some time and mental space open to deal with crises and opportunity as it shows up.

Next, you need to convert your to-do list into a when-to-do list. A when-to-do list is a to-do list but with dates and context.

Here is a 4-step process on how to make a when-to-do list work for you.

1. Add context and categories to your tasks

We have tasks across multiple areas of work and life. Specific project-related tasks, general administrative tasks, replying to emails, team management, business development, personal or family-related tasks etc.

We also have different contexts in which we’re performing these tasks. Tasks that need to be done at home, in the office, during a commute, in a supermarket, at a mall, on the weekend etc.

When you look at a to-do list that includes tasks from across the spectrum of all areas of your work and life, it is almost impossible to prioritise.

Make a list of all your categories and contexts

Instead, you need to look at your life and make a list of all the categories and contexts that apply to you. These contexts and categories need to be set up as lists, projects or tags in your task management system of choice. Next, every task in your list needs to be assigned to one (or more) of these categories. This can be done in most to-do list apps by adding tags to the task, or by moving tasks to a specific list.

Now, tasks from each specific category can be viewed together. Such shorter category-specific lists avoid the overwhelm of staring at the jumbled-up word salad that is your typical to-do list. This allows you to prioritise more effectively within a category of tasks.

You can now work on similar tasks together, also known as ‘batching’, Batching is a proven way of getting these tasks done both faster and better, and with lesser errors too. For example, If you’re focused only on business development tasks for a fixed period of time, you’ll do a higher quality job than if you had to keep switching between business development tasks and personal admin tasks.

2. Rewrite each task to be as specific and action-oriented as possible

Give yourself very clear instructions, as if you were delegating the task to someone else. Leave no room for misinterpretation or confusion. This will automatically lead to breaking down some tasks into smaller more actionable steps – which is exactly what we want.

This step creates a certain clarity about each task, minimizing any friction or procrastination and making it that much easier to get it done when you actually get around to it!

3. Pre-allocate blocks of times to categories

At the beginning of a week, you should sketch out roughly how much time you’d want to spend on any category or functional area.

These could be full days or blocks of time within a day. For example, Mondays and Thursdays could be mostly business development or marketing tasks. Tuesdays could be for more focussed deep work on cognitively demanding tasks such as writing, making a presentation, creating a financial model or coding. Wednesdays could be for team catchups, meetings and calls, Fridays for office or personal admin etc.

Whatever your categories, try and spread them out into pre-determined time blocks over your work week. Assume you’ll only have 2-3 hours to work on pre-determined time blocks. The rest of your day will fill up with requests, meetings etc that you can’t control or other urgent stuff that can pop up anytime.

4. Now turn your ‘to-do list’ into a ‘when-to-do list’.

Go through your list and assign dates to each task based on your pre-determined blocks for when you’ll work on that category. So if today’s marketing day, put the more important marketing tasks on your list for today.

Make sure it’s not more than 2-3 hours of category-specific work for today. You need to leave space for other critical or urgent tasks that will also need to be done today. Since there are only so many things you can do in one day, assign the rest of the tasks to the coming days. For example, if Friday is your day for finance/ admin tasks then schedule all finance/ admin tasks for the coming Friday.

Once you’ve applied this framework to your long list of tasks, you end up with digestible, actionable chunks of similar tasks scheduled throughout the week. Your weeks will have a rhythm, and you’ll end up working on important areas of your work and life holistically, rather than just chasing urgent tasks that pop up every day.

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