When analyzing other aspects of my life such as spending, I have tools to show me what I've done in the past, and those tools can help me improve (e.g. spending reports). This is admittedly reactionary, but I find it useful nonetheless. Track enough other "stuff about stuff", and I think the data could become interesting over time, providing similar "hindsight" that in turn can be used to improve oneself.
Of course, this means it will be necessary to have button things all over the place...