Dark stories, tales of whimsy and random brain droppings.

Just Do It

In my last post, I waxed upon personal task management in general. This week, I want to get specific about one of my favourite tools: Microsoft To Do.


Here’s how I have my task management system wired:

I use Microsoft To Do with my college account. It’s connected to Outlook Tasks on the back-end, so I don’t have to do anything there. It just works. As it should.

But I never use Outlook Tasks. Microsoft is deprecating it in favor of To Do anyway.

On my iPhone

I installed Microsoft To Do on my iPhone and as a desktop app from the Windows Store. I also use the web version frequently, as my workflows move increasingly to the browser.

I also configure iOS Reminders on my iPhone. This happens anyway when you setup your iPhone for email.

But I never, ever use iOS Reminders itself. I even turn off the notifications.

However, I do use Siri when I need to yell at my iPhone to remind me to do something. And that needs iOS Reminders.

“Hey Siri. Remind me Friday at 9am to do that thing for that person because it makes the world better.”

Siri picks it up, drops it in iOS Reminders, which is connected to Outlook Tasks, which then shows up in Microsoft To Do.

Now, if Microsoft To Do ever gets native Siri integration, these shenanigans would no longer be required.


The reason I don’t use Outlook Tasks and iOS Reminders directly is that there are some features, most notably subtasks, that are not backward compatible. You can create a task in iOS Reminders, but don’t edit one there.

So once you To Do, you don’t go back. You won’t want to anyway.

Here’s how the workflow of Microsoft To Do works:

All your tasks go to a list called Tasks. You can make other lists (and maybe you should), but the default “List of All the Things to Do before You Expire” is called Tasks.

There is this special list at the top called My Day and a prompt for you to pick a few items from Tasks to a list of what you’ll actually want to accomplish TODAY. If you don’t get a prompt, you click the lightbulb and and some suggestions will appear with plus-signs. You can always right-click a task anywhere and add it to My Day.

If you’re an agile software developer, you’ll recognize Tasks as the equivalent of the Backlog and My Day as the equivalent of the current Sprint.

There’s a bit of a ritual and cadence to using To Do this way. It’s meant to cultivate a daily practice of planning and establishing clear outcomes for the day.

What’s the definition of a great day?

When you’ve cleared out your My Day.

I have a daily calendar reminder to prompt me to do this first thing every weekday morning. More on my planning rituals another day.

Another special list under My Day is called Important. Pretty much what it says on the tin. If you Star a task, it’ll show up under Important.

I make it a practice to pick at least one or two Important items to add to My Day.

Another special list is called Planned for all the tasks you put a due date upon. This is pretty handy.

The list below it is Assigned to Me and that’s for shared tasks within To Do and Microsoft Planner. We’ll discuss shared tasks and Planner another time.

And then we have my favourite part of Microsoft To Do. There is a special list for Flagged Email. Because, face it: we all use our email inbox as a way to capture tasks. If you flag an email, it shows up in To Do.

And here’s the best part. You can add items in Flagged Email to your My Day. Which means you can actually get through the 170 flagged email you have accumulated. You can Star them as Important as well.

Below that is Tasks and then any other list you might have created or been shared with you.

Pro-Tip: You can edit the subject line in Flagged Email to identify the actual task or next action. Because an email titled “Board Report” isn’t enough of a tasks. Rename it to “Read/Review: Board Report for Jim because details matter” and add a date to it.

Note: If you’re still marking email as Unread so you can find them later instead of Flagging them, then we’ll have to talk. But not today.


The Anatomy of a Task

  • Circle. It dings when you click it to complete a task. Pavlovian, yes. But I don’t care. I’ll take my dopamine hit any way I can get it.
  • Title. As I said in my last post, a task is best stated as a mini-story. What for Who because Why. Action and purpose.
  • Star. All things are important, but some things are more important than others.
  • Steps. Some tasks are too big and it’s demoralizing to look at elephantine tasks. If it was more project-like, you could use a separate list or a tool like Planner. But if it’s just a big-ass task, why not break it down into steps? Gotta write that big planning document? Then break it down into steps for Research, Draft, Edit, Peer Review, and Polish. Each step gets a Circle, so there’s that.
  • Remind me. This is kind of like a Start Date. This is really a personal thing when it comes to tasks. If you’re a procrastinator, like me, then this is a prompt to prevent the ‘oh crap’ moments when you realize you have to do a 4 hour task in 30 minutes.
  • Add due date. Sometimes tasks have ‘em; sometimes they don’t. This is what makes a task show up in Planned.
  • Repeat. Setup the frequency and each time you complete the task, a new one shows up. Kinda like Purgatory, but in a productive sort of way.
  • Add file. Great for a reference document and where attachments show up in Flagged Email.
  • Add note. I like this one, because I can put website links here.

Way down at the bottom is a Trash Can for when you cry uncle on a task and just want to erase it from existence. Don’t feel bad. Sometimes, letting the ball drop is a good thing. It can test whether or not the task was actually important or not. It may have made sense two weeks ago, but doesn’t now.

I hereby give you permission to delete the crap you’re not going to do anyway.

Next week, we’ll take a look at Sticky Notes and how they fit in with Outlook and OneNote.

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