I redesigned the personal task manager

Alexander Obenauer
6 min readOct 19, 2017

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For a long time, I’ve thought that task apps should look a lot more like calendars. Here’s my idea for what that might look like.

It’s like Mail Pilot, but for tasks. That is — it completely re-interprets the task management app based on how we actually use tasks.

With a better understanding of the fundamentals of how we create, think about, and use tasks, I’ve designed a productivity app that is meant to significantly close the semantic gap between people and their productivity software.

It’s that gap that causes people to go in to a new task app firing on all cylinders, only to abandon it within weeks.

Instead, this design gets into the user’s head. It would allows us to visualize and interact with our tasks the way we think about them.

The Month View

We’ll dive into all the views, but I’ll start here because this one helps convey some of the initial concepts and motivations for this task app idea.

Here’s the month view. Thinking about tasks based on when you’ll do them allows you to be more systematic and prepared. It allows you to be more productive by not looking at a single, huge, daunting task list or backlog of things to do. It builds momentum by allowing you to see how much you’ve already gotten done this week, month, etc. It helps you see gaps in your planning.

It also allows you to find out the answer to the question, “what did I do last week?” Or last month. Or last February.

Besides regular tasks, you could define recurring tasks that need to land on specific days.

One of the most used features in Mail Pilot is reminders, with usage spiking at around 4 - 5 pm. Most days, some things have to be deferred. And that should be okay. Here, you can just drag items to other days.

Just like having multiple “calendars” in your calendar app, you could have multiple “calendars” here. Some could be shared with others, or they could be set up to sync tasks from other tools like Trello. You can toggle some off to focus on one area of your life, or you can toggle all of them on to see all the tasks you have to do — regardless of team or project — on one screen.

In most task apps, you’d have to back out of one project’s board, find another, and open it up. Without one central spot with all of your tasks, you can’t answer the question “what do I have to do today?” without a lot of cumbersome fumbling around an interface. Because of this, many people maintain separate personal to do lists, then have to update their project boards at the end of the day or week.

Having multiple calendars in one interface solves this problem in a really elegant way.

Week View

This week view allows you to plan your week and track your progess.

On Monday, you can design your week, seeing some things that have to be done by certain dates, and planning out all of the things you want to get done.

This view then allows you to, after putting a large task on a specific day, see if you have enough time to do prerequisite tasks, and add those to days prior so you know you’ll have everything done that you need to get done, on time.

When you’re planning out your week, you can see if you’re being realistic; if you overload a day, it’ll be visually obvious, and you can correct the issue in advance, without guilt or stress.

Tasks aren’t random. So why do task managers treat them as random, disparate bits of information?

When you’re planning your week, or when you’re in a meeting, use the notes tab to take all the notes you need.

Typing “*” followed by a space anywhere in your note creates a task.

Later, you can just look at all of the action items from the meeting, brainstorm, or other note.

When you drag tasks from notes into your calendar, they remain connected. You can click the context button on the task to see the note it came from.

And when you check off the task, it’s reflected in both places, so you can always check up on the status of your action items in a note, or on a day, without worrying what you put where.

Anywhere in your note, you could type “#” followed by a space to create a collection of related tasks (dare I say, “list”). Instead of one mega task that has subtasks hidden behind it as is the case in most task apps, this allows you to break something big down into achievable chunks, assign those chunks to different days, and still track the progress of the larger task from one place.

Not all tasks can be put on a day just yet. These three buckets would exist for such tasks:

  • Inbox — tasks you need to jot down, but don’t want to worry about placing just yet.
  • Blocked —tasks you need to get done, but that you’re waiting on something or someone else before you can place it on the calendar and begin on it.
  • One Day — tasks you’ve decided to defer to a later time, but you just don’t know when yet.

Day View

The day view is all about focus and context.

Let’s dive in.

The left is for context (and motivation). You can see this week’s notes and create new ones.

The right is for today’s tasks. Starring them allows us to focus in hard. And speaking of focus, you can go to “focus mode” which simplifies things way down:

This view pulls up just what we’re working on right now, and what we will work on next.

So that’s my idea for a task app. I call it “TaskCal” and I look forward to hearing your thoughts on it.

2020 Update: Guess what? This thing is happening.

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