On the use of regret to live a more virtuous life:

To “live life without regrets” is impossible because we are imperfect. There are thoughts, words, and deeds which all of us must repent. “Regrets, I’ve had a few but, then again, too few to mention,” sang Frank Sinatra in the incalculably pompous song, “My Way.” In Edwin O’Connor’s wonderful old novel, The Last Hurrah, the story’s hero, Mayor Frank Skeffington, lies dying as friends gather around, and one old political rival, who announces that if Skeffington had it to do all over again, he’d do it very differently. We want to cheer as Skeffington marshals the strength to say, “The hell I would!”

As much as we might admire the pluck of Frank Skeffington, we should, if granted a second or third or fourth chance to correct our errors, resolutely do so, secure in the knowledge that virtue often proceeds from regret rightly acted upon. Regret – accompanied by restitution and resolve – are not undesirable, but, on the contrary, are the wellspring of the examined life which, in turn, leads us to know, love, and serve God.

In 1984, Pope John Paul wrote (in Reconciliation and Penance): “The restoration of a proper sense of sin is the first way of facing the grave spiritual crisis looming over man today. But the sense of sin can only be restored through a clear reminder of the unchangeable principles of reason and faith which the moral teaching of the Church has always upheld.”

To have “a proper sense of sin” leads to the regret that converts sinners into saints. As we approach the remembrance of Christ’s death and resurrection this week, we should also keep in mind that through Him regret can be transfigured into joy.

Another way to think about yesterday’s Kierkegaard excerpt on regret is to first distinguish between regret and remorse, and then to distinguish between things you authentically regret and the recognition of which and resolve to live differently can positively change your life, and the sort of fruitless regret that Kierkegaard tends to be speaking toward, which is the regret of opportunity cost more than lack of living as a good person.