Sometimes it may feel mysterious as to why a person cannot keep their tasks organized. Just thinking about it leads to a sense of shame. As soon as you approach, you see that it’s a mess. The Inbox has a bunch of stuff in it. The today list doesn’t look like stuff you need to do. Overdue items are sitting there, still undone.

This appears to be clear evidence that you don’t know what you are doing, and that perhaps you never will. There’s just something wrong with you. You’re just a disorganized person.

I believe these awful negative feelings are just another reason why some “fall off the wagon” of Omnifocus, GTD, or any other system for that matter.

But the issue is that the perspective is off. Any amount of misalignment in the system resonates with a long-standing history of disorganization. This can lead to avoidance, which in turn, leads to greater misalignment and more negative feelings.

The reality is that the system will nearly always be disorganized, no matter who you are.

There is only one time that a task system is aligned well with your reality. That is the moment you have completed working on it, and even then only if you’ve done so exhaustively.

Whenever we leave a system to journey into the day, we and the world change. Meanwhile, the system stays the same. As a result, every time we approach the system it should absolutely be out of whack. You will have completed some things. Other things will no longer be relevant. Stuff will be waiting in the Inbox, some of which you may not even remember what they’re about.

That is natural.

But then you might ask, “Ok, so what’s the point of planning? If everything is just going to change, why bother setting up anything?”

“In preparing for battle I have always found that plans are useless, but planning is indispensable.” D. Eisenhower

The act of working on the system is what helps us determine our next actions. Sure, a well-tuned system will do a better job of prompting us about what, when, and where you might want to do something. That is a practice we can build over time. But, thinking through our work, weighing one thing over another, deferring and deciding, is where the real work happens.

So you might then wonder, “If I have to rearrange the whole system every time I approach it, doesn’t that take time?”

It does take time. But not terribly long, especially with practice. And, once you really have a sense of what it feels like to make a clear decision, acting from a settled state of mind rather than from impulse, tuning a system can feel quite liberating and well worth the time put in.

Certainly, one can use planning as a means of procrastination. Anything can be. As always, it is useful to pause and reflect, consider whether there is anxiety or other feeling one is trying to avoid from work. No tool will replace self-reflection.

As a general frame of reference, if it has been only a short time since I was last at my system, for example an hour, it might take only a moment or two to get things re-aligned.

When it has been some time, perhaps several hours or a day, I can still get it together in about 5-10 minutes. If I really need to review a bunch of projects and other parts of the system, the process may take up to 30 minutes, which is about what I take during my weekly review. These are, of course just general numbers. More likely, it depends on what type of work I’m doing.

Write post – the approach – sometimes you may feel overwhelmed by looking at the mess of your system – it’s evidence that you are a disorganized person – but it’s not – everytime you approach the system it will be out of whack – that is the nature – something happens in the planning – plans are useless, plans are everything