Prioritizing Calendar Management and Task Categorization for Productivity

So, you’ve decided to get yourself better organised. What would be the best way to start? That’s the question I am answering this week.

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Script | 324

Hello, and welcome to episode 324 of the Working With Podcast. A podcast to answer all your questions about productivity, time management, self-development and goal planning. My name is Carl Pullein, and I am your host of this show.

Whenever I begin working with a new coaching client, one of the first places we often need to start is unpicking the old system that is not working and transitioning into a system that does work. 

Everyone is different. We have different times when we can focus, and we do different kinds of jobs. I recently watched an interview with J P Morgan Chase bank’s CEO Jamie Dimon, who wakes up at 4:30 to 5:00 am each morning so he can read the financial news, exercise and have breakfast before the day begins, which inevitably involves back-to-back meetings. 

Waking up at 5:00 am may not work for you. You may prefer working late and waking up around 8:00 am. 

But wherever you are in your productivity journey, if you want to develop a system that works for you, it will inevitably mean tweaking your old system at least somewhat. That being the case, where would you start? 

And that means it’s time to hand you over to the Mystery Podcast Voice for this week’s question.

This week’s question comes from Frank. Frank asks, Hi Carl, I’ve decided to get myself organised. I’ve tried everything over the years, and I have bits of all sorts of systems everywhere. If you were to start all over, what would you do first?

Hi Frank, thank you for your question. 

I approach this by looking at the hierarchy of productivity tools first. There are three tools we can use to help us become more productive: your calendar, task manager, and notes. Of those three, your calendar is the top one. That’s the one tool that is never going to deceive you. 

It shows you the twenty-four hours you have each day and tells you what you can realistically do given that time. 

Your task manager is the most deceptive tool you have. You can load it up with hundreds of tasks, yet it never tells you if you have the time available to do those tasks. It doesn’t even tell you which tasks would be the right ones to do at any given time. Perhaps AI will help us in the future there, but I doubt it.

I doubt it because while AI could see everything and may know what deadlines you have and where your appointments are, it will not know how you feel. You may be coming down with a cold, might not have slept well, or had a fight with your significant other. Any one of those could derail your effectiveness, and they are things you cannot plan for. 

So, when starting out, get your calendar fixed first. 

What does that mean? 

It means first letting go of all your double-booked times. You cannot be in two places at once, and if you do see a scheduling conflict on your calendar, these need fixing first. This may mean you need to renegotiate a meeting or move something to the all-day section.

I’ve seen people putting their daughter’s driving lesson on their calendars. This often leads to seeing an appointment with a client at the same time as the daughter’s lesson. If you need to know your daughter has a driving lesson at 3:00 pm, put it in your all-day section of your calendar with the time in brackets—preferably in a different colour. You will find this cleans up your calendar significantly. 

The next thing I suggest you do, Frank, is to look at all the tasks you have to do and categorise them. It’s likely you will have tasks related to communications—emails, messages and follow-ups, admin, and chores. Beyond that, it will depend on the kind of work you do. A journalist will spend a lot of time writing, a designer will spend time designing, and a lawyer will likely spend a lot of time writing contracts or court documents. 

Whether you’re writing, designing, or doing something else, you want to group similar tasks together. 

In a task manager such as Todoist and Things 3, you can assign labels or tags to a task. You would use these labels or tags to assign a category to your tasks. This way, you can easily group all similar tasks together. 

The next step is to look at your calendar and assign blocks of time for these categories. Some may not need specific time blocks, but I encourage people to allocate blocks of time for communications and admin. These will always need doing. The problem is that if you do not have time assigned for them, the next day, instead of requiring forty minutes or so, you will need double that time just to catch up. This is not a good time management strategy. 

One question I often get is about dating tasks. I do recommend that you date tasks, but only for tasks you know need to be done this week. 

There’s a lot that can change between this week and next, and what you may think needs to be done the following Thursday could quite easily change to either need to be on Monday or not at all. If a task does not need to be done this week, place it in your next-week folder and forget about it. You can come back to it when you do your weekly plan. 

While we are on the subject of dating tasks, beware of the things that are not tasks that can end up in your task manager. Your bill payment dates, your son’s graduation and your next dental appointment are not tasks. These are events and should be on your calendar. 

You may need to know day-specific information on a given day. This information should always be on your calendar. I have my wife’s exam week dates, when my parents-in-law are staying, and public holidays on my calendar. None of these would qualify as a task unless I needed to do something on them. 

Most of these are simple tweaks anyone can make to their system without the need for a complete overhaul. 

The biggest challenge I find people struggle with is stepping away from firefighting addiction. This is where a person is hooked on running around panicking about everything they have to do. This just does not work. It leads to only doing easy, so-called urgent tasks and never getting anything meaningful done. 

The next thing to look out for is the dilemma of being able to do anything, just not all at the same time. There’s something inherently faulty with our brains. We believe we can do a lot more than we actually can. No, you cannot complete fifty tasks and attend seven hours of meetings in a day. Not only is it unrealistic, but it’s also a guaranteed way to burn out. 

Part of the problem is we like to see twenty, thirty or more tasks on our daily to-do list. It makes us feel important and useful. Yet it’s a delusion. You cannot do that number of tasks with a high level of competency. 

I find it interesting that people feel ashamed when all they have on their to-do list are three or four tasks. Yet, that is what you want to be trying to get to. 

You can accomplish this by moving towards a time-based system and away from a task-based one. This means instead of counting the number of tasks you have to do, you instead allocate blocks of time to specific categories of tasks. 

This then allows you to dedicate an hour to responding to your messages, for instance. Then, instead of having a lot of email tasks in your task manager, you have a single task telling you to clear your actionable email folder. Similarly, you can do this with projects. Rather than having fifteen or more tasks related to multiple different projects each day, you have a single task telling you which projects to work on that day. 

You will finish more projects faster if you focus on one or two projects each day instead of diluting your effectiveness by trying to work five or six projects each day. 

You can then use the third tool in your toolbox, your notes. This is by far the best place to manage your projects. You can keep project and meeting notes, links to documents and emails and checklists of things that may need doing. You then only need to link the project note to the relevant task in your task manager for a single click and in experience. 

The advantage here is you avoid the possibility of being distracted by something else. You see a task telling you to work on the next board meeting presentation, and click the link that will take you straight to your project notes, where you will find links to the presentation file, your research and other relevant information. 

The alternative is to be clicking around, looking at a long list of tasks which will only demotivate you and waste a considerable amount of time looking for something to do instead of being directed towards the exact task that needs doing next. 

Now, what about all your old stuff? 

The first thing to know is that the way everything is right now may not be as bad as it first looks. I strongly suggest you consolidate your tools into three—a calendar, task manager, and notes app. If you have multiple different apps, choose one for each and combine everything into one. You do not want to be wasting time trying to remember where everything is. 

Then, go through your tasks in your task manager, deleting old tasks that are no longer relevant and cleaning up your calendar. 

Your notes are less important. These can be kept as you don’t know which ones may be a source of inspiration in the future. You can move old notes to an archive. There, they will be out of the way but still searchable if you ever need them.

I hope that has helped, Frank. Thank you for your question.

And thank you to you too for listening. It just remains for me now to wish you all a very very productive week.