Some one asked me recently, “What does ‘mourning for your sins’ look like?”
Below is what I answered. It is only my best guess. Certainly those with more experience would know better.
There is a sorrow, a godly sorrow, that leads to repentance. This sorrow is for sins (specific misdeeds or attitudes, or mistakes or failures) that I have committed. This sorrow (when it is rightly experienced) leads to repentance. However, there is also a different kind of sorrow that is not for sins so much as it is for sin (the condition of brokenness experienced not only by me personally, but which is the experience of every human being: the brokenness of fallen human nature). So often when the Fathers are speaking about sorrowing for your sins, they are speaking about a kind of continuum that begins with our experience of personal failures, leads to ever deepening repentance (which is the changing or transforming of our minds and our turning to God) and results in a profound knowledge of human brokenness for which one bears a certain sorrow, but a sorrow mixed with hope and even moments of joy in that God has become man and healed the broken nature of man—even if it has not yet been realized in the lives of many people (nor will be realized, perhaps, in many people until the eschaton). So mourning for your sins is not necessarily just one thing. It is a journey. It is a movement from personal to universal and back to personal again as we learn to see ourselves as personally accountable for the brokenness of all of human nature.