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This intentionally provocative statement could be construed as self-defeating, given our goal to help people be more productive. Presumably, part of being more productive is actually meeting your deadlines.

But “deadlines” are one of the big downers of task managers because they are overused and misused, applied to everything as if everything could be managed in terms of time.

You enter a task. You studiously assign timeframes: deadlines, start dates and alarms. The dates are often meaningless, but you fear that if you don’t, you’ll completely forget about it. Then, when the dates roll around, you end up with a big pile of overdue tasks. You clearly cannot deal with all of them now and you still don’t have a good way to ensure that you won’t forget about them. So instead, you constantly carry around the baggage of a long list of overdue tasks. Oftentimes, overdue tasks turn into moot tasks. Stuff you never got to and then it was too late and well, looks like it wasn’t really that important. (This is perhaps the most common reason people give for why they just don’t need a task manager.) But when you first thought of the task, it would have been like pulling teeth to admit that, so you dutifully entered it and set a due date anyway.

Trying to guestimate when you’ll actually do things and how long it will take you and by when you’ll have them done, aka time management is an exercise in futility…as far as “knowledge work” is concerned.

It’s absolutely essentialy for things like dentist appointments and paying your rent. But the benefits are less clear for tasks that start with verbs like Brainstorm…Look into…Evaluate…Think about…Follow up on…

This is not to say that there aren’t hard deadlines for the end-goal of all your Brainstorming and Looking into.

And a “responsible” person would leave themselves plenty of time to brainstorm before the product of that brainstorm needs to be handed in as a concrete deliverable. But the reality is, trying to quantify how much brainstorming (3 hours) you need to do and when you’re going to do it (2 days before the write up is due) is an exercise in futility.

Which is why many people don’t bother trying to record and track these random one-off thoughts in any kind of an organized system (unless you count email as organized.) Instead, they’re strewn across desks on little bits of paper, desktops in text files, emails, sticky notes, napkins and last but not least, your brain.

The problem for a growing number of people is, there is too much of this “stuff” to keep track of in your head and still no good way to keep track of them outside of your head. Traditional task management solutions designed for “concrete” tasks are too structured. Not very structured solutions like paper notebooks and text files are well, not very structured.

Chandler attempts to walk the line by offering just enough structure to get you “organized enough” without imposing so much structure that managing the solution becomes a task in and of itself.

“Avoiding the futility of time management” is precisely why the LATER section in Chandler does not offer more granularity. It was intentionally missing options for designating more granular sub-sections like Tomorrow, Next Week, in 2 Weeks. You can always assign alarms to items so that they automatically pop back into NOW on a particular date. But unless you have a very specific date in mind, the idea is that really, you have no idea when you’re going around to thinking about this again.

On the other hand, we have seen that users quickly accumulated so much stuff in LATER that they begin to see the LATER section as a black hole. If you want to forget about something, put it in LATER.

In Part 2 of this post, I will get go into more detail about how we might reconcile these two opposing forces in the user experience.