KISS or “Keep It Simple Stupid“ is a phrase I’ve heard regularly. The phrase is often used to warn against the use of an application or process that has a complexity to it.

I do believe that simplicity is a hallmark of maturity.
However, I think the simplicity referred to is not necessarily within the instrument itself. I prefer Einstein’s comment:

“Everything should be as simple as possible, but not simpler.” – Albert Einstein1

Unfortunately, by the nature of the idea that simplicity is not always the answer, I cannot resolve this post into some pithy comment.

A task management system perhaps can be likened to a ship. The more robust a ship one builds, the more maintenance it requires, but potentially the further the travels possible. Meanwhile, if it is too large, it cannot be steered nimbly and becomes difficult to move at all. Regularly considering the attention it requires to maintain is crucial.

We hope to minimize the upkeep, perhaps even giving it a sense of self-perpetuation where possible. The less attention we need to devote to maintenance without negatively impacting its sustainability, the more attention is available for other pursuits.

Simplicity may well be a hallmark of maturity. But, it is not often a first step. Instead, it is a character of mastery gradually woven into our endeavors and lives.

As we attempt any new project or craft, we build supports, not fully knowing their upkeep or maintenance. How could we know? We haven’t done it before.
While we could take the word of those who claim experience before us, and it is certainly important to hear their thoughts, we must also experience it for ourselves. Without grounding in the self, we are without play, and therefore without mastery.

As we continue our paths of work, reviewing, repeating, and building iteration into our systems, we learn and re-learn the basics. We find new ways of constructing and creating. In the process, costs of our supports become more readily known.

Only then can we fully consider,

“Is this worth its cost?”

When asked regularly, the question prunes the gardens sown into any sought simplicity.

I put together an example of a list I sometimes use for practicing piano, to help me keep track of what needs practicing and when. It wasn’t something I created quickly or when I first began using a task system. But with practice, it became a useful simple place to turn, despite the complexity underlying it.

An Example in OmniFocus

As an example, I can describe my use of OmniFocus in creating a practice perspective. Here is an example of what I see when I practice:

It is arguable a very simple list. However, there is a complexity behind the scenes. Each of the tasks have a different repeat frequency, catering to the practice schedule I want for any individual piece. I can always increase or decrease those frequencies.
Panning the camera back for a moment, I can show a section called Available Now:

If I open the disclosure triangle next to it, you can see a number of pieces that I might want to add to the practice hopper simply by adding today’s date to the Defer date field:

Which could result in:

So, I guess what I advocate is a simplicity in use with only the necessary and sustainable complexity to support it.