My to-do lists get more and more complex over time.

I’ve explained here why I like My Life Organized (or “MLO” for short).  Briefly, MLO allows you to organize your tasks into a hierarchy, so that bigger tasks can be divided into smaller tasks and tasks without an organizing principle can be grouped into higher-level “projects” or simply “folders”.

But a consequence of this for me — and I think for any PIM-head who takes this stuff seriously — is that the list of tasks invariably grows and becomes more complex.

Most PIM software has a way of ranking or sorting tasks: by “importance”, by “urgency”, by overdue-ness, by all of the above.  It would be nice to build in to the PIM software some kind of scoring for simplicity as well.  One PIM tree is simpler than another if it isn’t as deeply nested, or if there isn’t a large degree of co-dependence between the various tasks, or <pick your simplicity function here>.

You could then have the software detect and warn you if you were adding on complexity at an alarming rate, and give you some tactics (or even semi-automated processes) for simplifying your PIM tree.

Be careful what you wish for, I guess.  I used some PIM software for a while which would actually put your tasks into the calendar based on the importance sort (and available time slots: each task had to be assigned a length).  Tasks could be split up to some extent, and it was nifty for a couple of days, but then it really got like Dr. Evil’s “unattended killer machine” that was supposed to do in Austin Powers and never did.  It was a major task trying to re-jigger the tasks so they would fit into the schedule where I knew they should go anyhow.  And finally, to achieve simplicity, I threw the software overboard and moved on.

Maybe a simplicity automaton would work better than an automatic scheduler, but I suspect it too could be become a tyrant if wholly automated.  Best to make software our companion and not our master.