Scrupulosity does no one any good. To concentrate only on one's sinfulness and not turn outward toward God's mercy and reconciliation defeats the purpose of Jesus' death and shuts one off from the suffering of others.
We should be sorry for our sins, no question. Guilt and sorrow can lead us to reconciliation but if we never go past them then we are not advancing in holiness. Jesus reminds us that those who seek personal reward and recognition have only that (cf. Matthew 6:1-6).
John spent his early life in dissolute living and when he turned to God, his scrupulosity got the better of him. He sought martyrdom, and when dissuaded from that he publicly beat himself, publicly begging for mercy, and other non-rational actions (he was committed) trying to repenting for his past life.
With strong spiritual guidance he was able to come to understand true humility, that it was not all about him and his sinfulness. He then turned outward, serving the sick and poor and inspiring others to do the same. Only then, did he find the true peace of reconciliation and true mercy.
Pray that we will be guided, like John, to open ourselves to God's love, to eschew scrupulosity, embrace God's mercy, and do good for others - especially during the season of Lent.
If we look forward to receiving God’s mercy, we can never fail to do good so long as we have the strength. For if we share with the poor, out of love for God, whatever he has given to us, we shall receive according to his promise a hundredfold in eternal happiness. What a fine profit, what a blessed reward! With outstretched arms he begs us to turn toward him, to weep for our sins, and to become the servants of love, first for ourselves, then for our neighbors. Just as water extinguishes a fire, so love wipes away sin.
-- From a letter
Things to Think About