If one does a cursory reading of the life if St. Gregory whose feast we celebrate today, it can sound luxurious. The biographies speak of being born of a noble family, being a Roman senator at 30. What you have to keep in mind is that it was the Middle Ages. The Western Empire has fallen. Rome has been sacked on multiple occasions, and devastated by plague. Most importantly the seat of real power has moved to Constantinople. The Rome we might imagine was no more.
It is no wonder that after his father's death he would convert the family home in Rome into a monastery. He knew how fleeting the things of this world are. And he would have been content to live out his life as a monk, but God had something more for him to do.
He would be one of only three Popes to be recognized by the church as "the Great." The other two are Leo the Great and Nicholas the Great. He was elected Pope by acclamation.
Despite all that had happened to Rome, he did not despair. He set about rebuilding, rebuilding the Church's liturgy and it's unity. He rekindled the missionary spirit of the Church. Perhaps the most famous of the missionaries were those he sent to Christianize what we call England. In what some would call the Dark Ages he was a shining light.
On the memorial of St. Gregory the Great let each of us pray that we might be that same beacon of light and hope to those around us and thereby spread the Good News of Jesus Christ.