Managing regrets

Here's a subject that has always fascinated me. Regrets are a commodity available to all of us if we are courageous and open enough to help ourselves.

I conduct that search on a pretty regular basis, often to return empty-handed from my quest, which in and of itself is quite good.

Conventional wisdom asserts that we regret inaction more than action; in other words, not the things we do, but those we fail to achieve.

More recently, psychologists are making an interesting distinction between what they call the “ideal self”, that is what we'd be if we fulfilled all our goals and ambitions, and the “ought self”, as if we were more focused on meeting our obligations to others by taking the high-road, and living a stricter moral life.

They claim that people regret ideal-self failures – in short, not pursuing their dreams – more than ought-self failures, such as failing to visit a sick relative or failing to do what's morally right. This is because we can always “fix” the later whereas the opportunity to attain the former is often long gone and can't be regained.

This segmentation isn't far from Carl Jung's suggesting that we shouldn't be asking what we want from life, but what life wants from us; another twist that further complicates the ways we ought to plan and direct our own destiny.
This said, since my stash of regrets isn't that big, should I even worry about these subtle and complex distinctions?