The Solution to Task List Woes

I've never been able to get task lists to work for me, regardless of what app I used. So I threw all my lists and apps out and tried something entirely new.

I'm a pretty easygoing guy (most of the time). I don't hate many things. But I hate to-do lists.

Hate them.

Task List Woes

For years and years I've worked with an array of different applications to track the increasing number of responsibilities in my life. I've tried using Wunderlist, Todoist, Google Keep, Evernote, among others. I've even tried pen-and-paper planners. I even read the Getting Things Done book to adjust my process.

Nothing ever felt right. Any combination of solution and process just felt ... forced.

After about a decade of searching, I finally learned to-do lists just don't work. (That is, they don't work for me, but I'm guessing they don't work for you, too, if you're reading this!) They are inherently flawed right out of the gate. And that's not because of the applications I was using, either. While certainly not all apps are created equal, even the slickest of to-do apps can't solve the flaws inherent to task lists.

When it comes to working with to-do lists, there are three major problems that any of the apps (or even pen and paper) just can't seem to solve:

1. Due Dates and Priorities

Due dates for tasks are either crucial to that task or completely meaningless -- there's virtually no in-between. For example, if you have tasked yourself with buying a birthday present for little Jimmy, you must do that before his birthday party, when you're going to give him the present. If you don't, you've failed at that task. On the other hand, suppose cleaning your basement is on the top of your list and you added a due date of Sunday to get it done. What happens when Monday rolls around and you haven't finished it? Perhaps nothing. The date didn't actually matter.

The trouble with task lists is that its due date implies its priority, when it actually has nothing to do with priority until it does. If Jimmy's party is two weeks away, but cleaning the basement is weighing more heavily on you, then cleaning the basement is the higher priority, even though it has no meaningful due date. Purchasing and wrapping Jimmy's birthday present only becomes the higher priority when it has to -- when you have to perform the task to avoid it being late.

And yet, task lists tend to be so narrowly connected to the due dates within them. When a date is upcoming, all of a sudden that task becomes crucial, when it may still not be the highest priority. And tasks without due dates are easily lost even when they may be of high priority.

2. The Absence of State

Task lists tend to not have a natural mechanism for tracking state. What I mean by state is what is happening to the task at this moment. A task is typically in one of five states relative to you:

  1. It's something you want to, have to, or should do in the future.
  2. It's ready to be started.
  3. You're actively working on it.
  4. It had been actively worked on, but now it is waiting on some force outside your control.
  5. It's done.

Most apps don't have a good (or efficient) way of handling state. The method I've seen most often is to use a feature like labeling or tagging to show state. While that works, it's often not easy to see all tasks within that state while maintaining priority order.

3. Managing Multiple Lists

Most of us have a lot of tasks in our list. It seems like the older we get, the more there is to do. So it makes sense to break up tasks into their own groups by some methodology.

For many apps, groups are their own lists. And a list is just another way to view tasks. The problem is those tasks are still part of a larger system and it can be difficult to see priority across multiple lists (especially if you're using tagging/labeling to represent state).

These three problems make to-do lists inherently flawed. Even the most clever of apps have a difficult time solving for these issues because lists can't solve these problems.

Lists are great for things that are all on the same level, like shopping lists, pros/cons lists, or a list of ideas. But when you add the complexity of due dates v priority, the absence of state, and managing multiple lists without losing visibility into priority and/or state, lists are not the answer.

A Different Type of System

One morning I was reading in bed instead of getting up and being productive. I came across an article that struck my attention. (I can't seem to find the article -- if only I had a list). It was about throwing out to-do lists and using Trello to manage personal tasks. Trello uses the Kanban style of management in which cards (each representing a task) are physically moved across columns on a board as the state of the card changes.

At the time, I had been practicing this style of working with one of my company's clients. They used this awful product called Rally (I guess now it's called CA Technologies). As clunky as the thing is, it had gotten me used to the kanban style of working (we were technically using the agile approach, but it's similar enough to kanban).

This approach to managing personal tasks with the kanban style of management felt different. It felt unique in taking a project management tool and applying to personal life. It felt like it was at least worth a shot.

I must also mention that at that time I hated Trello. (I am apparently filled with more rage than I knew.) I'd tried Trello for a few different projects and it never seemed to stick. But, I had a theory that the reason Trello had yet to work for me was more of a people problem than a software problem, and that it might just work if I was open to a personal process change.

And it turns out it stuck. It was one of the best decisions I made last year. It has completely transformed the way I manage the tasks in my life. I have a nine-month-old baby that made her way into my life, and yet I feel like I'm getting more done than I was even before I had a kid.

The New System

So let's look at this system, and let's do it against the task list woes:

1. Due Dates and Priorities

In Trello (or with any kanban app or physical board) cards are arranged in a vertical column. Thus, the order of the cards can imply priority. And cards can have or not have a due date. It doesn't matter because the priority is set by the order of the column from top to bottom.

2. The Absence of State

Each column represents a state of a card. As mentioned, there are five states for any given task, so I have five columns:

  1. Backlog: Cards not ready to be worked yet.
  2. Queue: Cards that are ready to be worked.
  3. Active: Cards I'm actively working.
  4. Waiting: Cards that are waiting for something external before they can move forward.
  5. Done: Cards and the tasks they represents are complete.

To add to this, because the columns represent state, that frees up the ability to use labels to represent some other form of organization. This also means that in one view I have a clear understanding of the state and priority of every task, regardless of its "list" (more on this below) or its due date.

It's worth mentioning that this is an ongoing Trello board and it can feel cluttered if cards never go away. Every week -- usually on Monday morning -- I "groom" the board. I archive all cards in the Done column, so that column is fresh. And I rearrange from right to left, ensuring state is correct (it's in the correct column), priority is correct, and whether Backlog items are ready to be worked yet.

3. Managing Multiple Lists

When I've used to-do lists, I often worked with multiple lists. The closest I ever got to being organized and efficient was when I had a list for each "hat" I wore (role I played) in life. So there was a list for Husband/Father, Developer, Writer, Musician, etc.

With Trello, there's an idea of projects or boards. But they are completely separate from one another, so it doesn't make a lot of sense to use separate boards unless there are truly separate projects (more on that below).

Instead I use the labels (or tags) feature to specify the type of task it is (representing the role I play when I'm working on that task). It's not totally meaningful, but it helps me break up the tasks in my mind to retrieve the state of my life with a quick glance at the board.

That being said, the kickers that I must follow if this system is to work well are:

  1. Do not use labels to represent state in any way. Kanban immediately breaks down when labels become something other than an organization bonus. State is entirely determined by what column the card is in, and by that alone.
  2. When I have to do something at a particular time, it goes on my calendar. Something that is to be done at a particular time is more of an event more than it is a task. Trello is about managing tasks. If I have to take the trash out every Monday and I can't remember to do that, then I put it on my calendar. When I have to pick up the baby on a different schedule than normal, I put it on my calendar.

Quick, let's go back to the multiple boards. I do actually have two boards that I manage. One of them I call Personal Task Manager (PTM), while the other is Writing. My goal is typically to write about five articles each week -- three for Cobwwweb and two for this blog. Originally I was using cards on the PTM board for each article. But that also meant I was storing ideas for writing in the Backlog column. Eventually there was enough activity with writing alone that it made sense to pull out those cards into a completely separate board.

In other words, we could say that the rule is to use one board until it becomes too much. If one task has a set of subtasks, that's one thing -- Trello has a checklist feature for that. But if there's a large project to complete, the PTM's other cards may get in the way of being efficient while working on that project's tasks. For example, let's say I was going to build a deck in my backyard and am doing all the work myself. With everything else going on in life that could take a couple months to complete. It might make sense to pull out deck tasks into its own project and share those tasks with others that will be involved.

I've been following this new approach for several months and I've seriously never been more efficient, and this is at a time when I've also never had more going on than I do right now.

The Kanban style of management is brilliant in that it uses visuals more than data to help you stay organized and focus on the things that matter.

Try it. It's worth a shot.

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