Many of the tools for personal organization miss the mark, because they try too hard to simplify the complexity of our lives into forms and features. They often make it worse.
I coached an executive twenty-odd years ago, a Palm V user, and while that device is obsolete now, nothing about the problem has changed. He still couldn’t really make it work the way it looked like it was supposed to. There were too many options, too many fancy connections that on first look seemed like they might be useful. But in the “war zone” of real work, those features were much too cumbersome to maintain in any complete, consistent, and current fashion.
We were able to customize a system for him using Outlook (synching to his Palm V—any of you old enough to remember?) but we had to intelligently “dumb it down” so he could work with simple lists that were easy to add to and review, on the run.
Most of the fancy features of most organizing software still go unused, as do most forms and lines and boxes provided in paper-based planners. Is this the lack of intelligence and diligence of the users, or the inappropriate and unnecessary complexity of the tool?
There is a very fine balance point of maximum effectiveness between simplicity and complexity of systems. How much detail, how much cross-referencing, how much coding and categorizing is enough, without becoming too cumbersome? Most of what’s out there to help is grossly overbuilt. Once you realize that you only need to define your projects and the next actions on them and keep track of them in a complete but simple set of lists, you won’t need to bother yourself with much else. You’re better off being a good carpenter with a simple hammer than a novice with a garage full of unused power tools.
In anything at all, perfection is finally attained not when there is no longer anything to add, but when there is no longer anything to take away.-- Antoine de Saint-Exupery

I was looking to find the name of an old GTD software I used to use. Actioneer. It was the best. I found a comment I made in a GTD forum 2008
Indeed, what a great little tool it was. I used it years ago with my Palm V. I seem to remember there being issues with the GTD Add-In and compatibility. I think many folks strayed from the Palm/Palm Desktop format exclusively into Outlook and/or Lotus Notes. Your comment did bring a smile to my face as I fondly remembered Actioneer and my Timex watch that would sync with Schedule Plus! I think I got that from the Covey Leadership Center before the merger with Franklin Planner. Yes, long ago and far away...
I spent 25 years in the Toyota orbit and one of the things that sticks with me are the various wastes outlined as sins in their culture. And the one waste I see everywhere is the waste of overproduction. It's why I find most PowerPoint centered presentations like fingernails on a chalkboard.
I found a great solution for my to-do list that I've been using since version 1.0 (version 4.0 is reportedly in development) which is enough, but not too much. And it tracks towards the minimalist side of software.
1000% agree with your thoughts on how we can get lost in our tools.