Your calendar is a lossy to-do list

May 30, 2022

Table of contents:

  1. What is a calendar?
  2. How do people use calendars as to-do lists?
  3. Why do calendars not work as to-do lists?
  4. How is a calendar a lossy to-do list?
  5. A calendar is just an output target

One of the most popular ways people manage the things they need to do is via a calendar. A common expression you might have heard is, “if it’s not on the calendar, it doesn’t get done”.

In certain situations, a calendar can be the perfect way to manage your tasks. If everything you need to do revolves around events pre-scheduled for fixed points in time, a calendar is the perfect tool for the job.

But for most people, using a calendar as a to-do list is a terrible solution.

If you are currently managing your tasks via a calendar, but you’re feeling overwhelmed and not making progress, you might be using the wrong tool for the job.

What is a calendar?

Before we get too far into the weeds of using a calendar as a task list, let’s just take a moment to really understand the job of a calendar.

I’m going to take it for granted they you’ve used a calendar before as it’s probably one of the most common types of software that comes pre-installed on every computer. It also comes bundled with just about every email account.

A calendar is essentially a system that is used for organising dates and times. A calendar is a grid divided into sections that represent different periods of dates and times. The grid can represent hours, days, weeks, months, or years. Typically you will view a calendar at a level of abstraction, for example a single day, a week, or a month.

Your events (or tasks) are arranged on the calendar by when they should happen. The location of the event (or task) is such that it appears in the location represented by that date or time. For example, if you had an hour-long meeting with a client at 10am on a Monday morning, the event would appear in the 10am to 11am period box in the Monday column.

How do people use calendars as to-do lists?

As you can see, a calendar is the perfect tool to represent the relationship between things that should happen at a specific date and time. However, problems arrise when you try to use a calendar for a job it’s ill-equipped to handle.

Typically the problem occurs in one of these 3 scenarios:

Calendar + disorganised tasks

In this situation, the person uses a calendar for their date/time-based events, but is generally disorganised with their other tasks.

This means calendared events are given the highest priority, whereas everything else is completed in an ad hoc fashion, usually by trying to fit them in between the cracks of whatever is on the calendar.

This can work if you are a manager or sales person that spends the majority of their time in meetings. However, if the value you bring is not directly tied to you attending meetings (ie creating something) you’re doing yourself a disservice.

Calendar + separate to-do app

The second situation is where the person uses a calendar for their date/time-based events, and a separate to-do app for all other tasks they have.

This means the person now has two sources of truth when they are looking to evaluate what they need to do, which leads to conflicting, or overlapping scheduling between their date/time-based events and everything else they need to do.

This lack of visibility makes it much harder to communicate your availability to others as there are now multiple places to check. This usually leads to the situation where date/time-based events are given default highest priority, despite that not always being the case.

When your work is scattered across multiple places, it’s much more difficult to find a sense of calm and confidence in what you have to do.

Everything on the calendar

The final situation is where everything that needs to be done is added to the calendar, even if there isn’t a reason why a certain task should happen at the given date or time.

Once again, date/time-based events are given the highest priority, and everything else is slotted in between.

This means that tasks are scheduled into the available space, not by when would be the best time to complete this particular task.

When tasks are pre-scheduled in advance into a fixed calendar, it makes the whole method very inflexible and fragile. Things inevitably change, overrun or need to be moved around. It also doesn’t make sense to pre-schedule tasks far in advance when priorities or objectives are very susceptible to change.

Why do calendars not work as to-do lists?

So as you can see, the primary function of a calendar is to organise events by periods of dates and times. Events are a specific type of task and so it’s important to recognise and understand not just how events can be scheduled, but how they fit into the broader view of everything you need to do.

A calendar is an output target for a given list of things to do, where date and time are given highest priority to the detriment of everything else.

The prioritisation of a task is not always determined by the date and time it should happen, in fact doing so can be extremely detrimental to your productivity.

How is a calendar a lossy to-do list?

When you describe something as “lossy”, it means there’s a loss of data, or context. For example, lossy video compression means the file size is smaller because you lose some of the quality that is transmitted.

A calendar is a lossy to-do list because by prioritising date and time over everything else, you lose the nuance of the task.

A task is not just the description of something that needs to be done. A task is made up of a rich profile of characteristics, each of which has a huge impact on the optimal way to complete the task.

By forcing a task into a calendar, you are elevating potentially an unimportant characteristic of the task, and losing the nuance of how best to complete the task.

A calendar is just an output target

Now, I’m not saying calendars are bad. A calendar can be a wonderful tool for your productivity when used correctly. A calendar is probably the most intuitive way to visualise what you’ve got going on at specific points in time, and what is coming up in the future.

When you look at a calendar, you get an immediate sense of how busy you are, or how much time you have available by looking at the white space (or lack of) between items.

But a calendar is just an output target for a given list of events. It’s just another way to visualise what you’ve got going on. Critically, it’s a way to visualise tasks where date/time is given the highest precedence.

Unless everything you need to do is predicated on fixed scheduled dates and times, you are using the wrong tool for the job when attempting to use a calendar to make the most out of your productivity.

Philip Brown


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