Previously on C. Kennedy Design, I described staying productive and included some detail on how I use Microsoft Planner and Microsoft To Do. I've continued to contemplate how I plan projects and move them to completion and I couldn't help but wonder... Is perfect planning/tasking software possible? And if so, what would my perfect look like?

Current take: my planning/tasking life has two core necessities:

  • A way to organize tasks into logical groupings: categories, subcategories, projects, buckets, etc.
  • A way to queue tasks so I know what to do next.

There are no major deficiencies in how the Microsoft Planner/Microsoft To Do solution approaches organizing tasks, and I don't think I have major insights on the matter.

Queue organization is something that is still very unsolved.[1] Honestly, it's something I hadn't considered explicitly until now. If there is perfect out there, my perfect needs to get queueing correct.

While visualizing how my process has evolved to move tasks from discovery to completion, I ended up with this:

Task-Pyramid---Original-1

This was my aha moment! I cleaned it up and dubbed it the Task Pyramid.

The Task Pyramid
Task-Pyramid---Whole

Two core components of my queueing system are:

  • Capture all the tasks that come into my life,
  • Promote tasks through a number of stages, from ¯\(°_o)/¯ to Do This Today.

Personally, if I'm not careful, each task that enters my life tries to capture my full attention and cut to the front of the line. Every task can feel important, and many are, but not every task can get done. With the queueing method I use, every task that enters my life gets pushed into the first stage of the queue... no cutting allowed.

Ground Floor - The Entry Point
The ground floor of the pyramid is the entry point and default position for all tasks.

Task-Pyramid---Ground-Alt
We start at the bottom...

These tasks all live in Microsoft Planner.

Task-Pyramid---Planner-1

A task can happily live here indefinitely with no issues, which is good because these tasks can be literally anything. In my actual Planner account (not pictured above) I have:

  • Tasks waiting for me in case I ever build my ultimate dream house. (It has a tennis court/event space for the first 2 stories.)
  • A task noting what I would do if I had USD 1,000,000,000 to spend.[2]
  • A task to create a 1975 Album of the Year post.

I'm more likely to create the 1975 post before getting a billion dollars to spend; at the moment, both tasks are on the ground floor, because I'm not doing either of them soonish.

For the record...

  • This level lives in Planner.
  • Right this second, I have 168 tasks at this level in my personal account.

2nd Floor - Soonish Tasks

The second floor of the pyramid contains the tasks I would like to do soonish. This is my "Oh that's right -- I should really do that..." level.

Task-Pyramid---2nd-Alt-1

To promote a task to the 2nd Floor/Soonish Tasks, I browse Planner and assign tasks to myself, which creates a linked task in To Do.

Task-Pyramid---Planner-assigned

Tasks in Planner that I've assigned to myself

Task-Pyramid---Todo-assigned
Auto-created tasks in To Do, which are linked to the original Planner tasks

If I don't already have bite-size tasks ready to push a project forward, the promotion from the Ground Floor to the Second Floor is when I break large tasks into actionable bits. When I'm promoting something to the 2nd Floor of the pyramid, it should be something I could check off my list tomorrow.

A pre-pandemic example: a ground floor task like "Make desserts for party" might get split into:

  • Make dessert 1
  • Make dessert 2
  • Make dessert 3
  • Make a grocery list for desserts [Gets promoted]
  • Go grocery shopping for desserts [Gets promoted]

I try to keep the number of 2nd Floor/Soonish Tasks reasonably limited; the second floor is basically a small menu of self-explanatory items, ready to be completed.

For the record...

  • This level lives in To Do, in the "Assigned to you" task list.
  • Right this second, I have 5 tasks at this level in my personal account.

3rd Floor - The Short List
The 3rd floor of the pyramid has all of the tasks I would do today, if today were long enough.

Task-Pyramid---3rd-Alt

To promote a task to the 3rd Floor/Short List, I find it in To Do's Assigned tasks and also star-toggle it to include it on the Important tasks list.

Task-Pyramid---Todo-assigned-starred

Assigned tasks in To Do, with two of them starred

Task-Pyramid---Todo-important

Starred/Important task list

I use Planner to plan and organize projects; when it's time to roll up my sleeves and complete tasks, I use To Do exclusively.

In a perfect world, the 3rd Floor would be the top floor of the pyramid. In this world, I often don't complete everything I might want to in a given day.

At the office, where I'm more likely to get unexpected tasks added to my list, I might populate the 3rd floor at the end of the work day, grabbing tasks that I would love to do tomorrow, and wait until the next morning to promote tasks beyond the 3rd Floor.

For the record...

  • This level lives in To Do, in the "Important" task list.
  • Right this second, I have 2 tasks at this level in my personal account.

Top Floor - Today Tasks
The 4th and final floor of the pyramid holds the tasks that I'm doing today.

Task-Pyramid---Top-Alt

...now we're here.

To promote a task to the top floor, I find it in the Important tasks list, and also add it to My Day.

Task-Pyramid---Todo-important-my-day

List of Important tasks, with one added to the My Day list

Task-Pyramid---Todo-my-day

The My Day list

At the office, I might look at the 3rd floor in the morning and decide which one or two things I definitely want to accomplish. Even if those tasks are relatively quick, I may only promote those two things to the Top Floor. If I get distracted or pulled away, it's nice to come back and only see the two things I decided were most important. (And if I complete those things quickly, I can always pull more tasks to the Top Floor.)

For the record...

  • This level lives in To Do, in the "My Day" task list.
  • Right this second, I have 0 tasks at this level in my personal account.
    • In theory I would love to have the item "Edit Task Pyramid post" at this level, since that's what I'm actually doing today; please see "Chipping Away" below.

Considerations
Some notes/considerations about this task queueing method.

The important of blinders
The most helpful thing about this system is that I physically see fewer options as I get closer to the tasks I want to do today. Since each queue stage lives in its own, distinct interface, there's no fiddling with filters to remove the excess. It's fast and focused and it doesn't visually (or emotionally) overwhelm with all the tasks I could be doing.

Chipping Away
Here's an example of the most common, unsolved problem I encounter with my current queueing process: A post like this one requires many rounds of editing. It's useful to have an item like "Edit Task Pyramid post" work its way through my queue. How do I both A) have that task in my queue until it's done and also B) have a task I can check off when I complete a round of editing?

Reading and editing a piece again, and again, and again isn't exactly a large task that needs to be broken into smaller tasks... it's a single task that gets repeated until I decide it's done. Unfortunately, single tasks don't temporarily-but-indefinitely repeat all that well. I have some ways I try to work it in, but honestly I'm just winging it. [3]

Knowledge-as-Task Kills Dashboards
Not all planning data are tasks. I sometimes have notes, considerations, or reminders to keep near tasks.

Task-Pyramid---Notes-with-Tasks-1

A screenshot of Planner, with some persistent notes stored in task cards

I use tasks to store this non-task information, which is mostly fine. The information is there when I need it and it doesn't really get in the way. It does, however, make the dashboard of undone tasks inaccurate.

Task-Pyramid---Dashboard

A screenshot of a Planner dashboard; note there are really only 2 items Not Started, since one of those items contains notes and is not a task.

The dashboard might list 30 undone tasks, and 7-10 of them aren't true tasks... they're notes, saved websites, reminders.

This isn't the biggest deal: I've never felt hindered without the dashboard. But it also means I never use the dashboard.

Does Perfect Exist?
So what about my happily planner after?

I'm not sure anyone would be able to build something significantly better than the Microsoft Planner and To Do process I've evolved for myself... not better enough to warrant transferring my projects and tasks to a different piece of software.

Microsoft Planner and Microsoft To Do feel like a 75% solution for a problem that could very well be specific to how my brain works. Provided they don't make any changes that break what I'm doing, I'm fairly pleased.

That's not what I expected coming into this exercise... I thought there could be an obvious road to a better, more unified solution. But Planning/Tasking is just complicated; personally, I feel like I'm activating two different parts of my brain when I'm doing one or the other. Even if there were a single piece of software handling it, I don't think the two activities are close enough to each other to have a shared interface. And if that's the case, Planner and To Do feel most-of-the-way there. There may be a road to a better solution, but it's not obvious to me.

For the record, if I were designing from scratch here are some nice-to-haves:

  • A single database, obviously. That said, the link between Planner and To Do has always been fine.
  • I might like a way to archive completed Plans/Buckets in Planner. (Right now deletion is the only option.)
  • A dedicated option for storing non-task info alongside tasks.
  • If I were literally designing this software only for myself, I might put in a UI that looks like a pyramid, so I could drag and drop tasks between floors.

  1. As far as I've seen. ↩︎

  2. That's $1B after taxes. If anybody has a clean billion dollars they want me to spend, slide into the DMs. ↩︎

  3. This sounds like the problem with daily "good for me" tasks I tackled earlier in the year. ↩︎