In our own time of societal decay, it is important to try to get into Benedict's mindset, first remembering several vital facts: First of all, Benedict was a layman. He saw a need and took the initiative to start his communities. While he did nothing contrary to the teachings of the Church, and did not rebel against the rightful authority, he also did not sit around waiting for a priest or bishop to give him a job. With the grace of his baptism he simply got on and did what he was called to do. Details in his famous rule suggest that Benedict was somewhat cautious in his relationship with priests and regarded them as necessary, but not necessarily trustworthy.
It is also important to understand the monastic relationship to culture. A monk sees the decaying culture and believes the only possible response is withdrawal. He despises any Christianity that compromises with the decadent society, and he does not think "dialogue" is either desirable or possible. He does not believe that prophetic imprecations and predictions of God's judgment on the immoral culture are useful. Like St. Anthony of the Desert and the first monks in Egypt, the traditional monk believes that withdrawal from the world is the only way to save the world.
The third thing to remember about Benedict is that he probably never anticipated the great resurrection of learning, culture, and spirituality that would flow from his decision to live simply in the Italian hills following a life of prayer, work, and study. In other words, he was faithful where he was with what he could do. Whether it came to something or not wasn't his to decide. The fact that his movement eventually produced phenomenal accomplishments in virtually every area of human achievement, was the foundation for a new civilization, and changed the world forever was not something he either anticipated or predicted.