In this section of Paul's letter to Corinth we discover that there was a 'severe letter' which he had previously sent the church. When we place this together with other references to his own letters throughout 1-2 Corinthians, it seems that there were at least four occasions of correspondence from Paul to Corinth alone (some scholarship has reached five). It is clear that it took a lot for Paul to send the 'severe letter' to the church at Corinth, and he mentions how he initially regretted sending the letter (v. 9), because of the outcome he is no longer bothered by it.
This, in some circles, is the notion of tough love - caring enough to do what is necessary for another person even when it is not a popular or feel-goody action. This may come (as in Paul's case) through words that we use, or in actions that must be taken in a given situation. While Paul felt that such a course was necessary, it clearly was something that disturbed him deeply when he committed himself to it. Why? Because the work of pastoring for Paul is, on this level, the same for ministers today: surrounded in the context of defensiveness and distrust.
And . . . let's face it, nobody likes to be told where they're wrong, not even a 'gentle' rebuke is welcome news. Perhaps the biggest difference between Paul's world and our own on this point is that we sorely miss pastors and elders and leaders in the church who are willing to do the right thing, bring someone to the grief of their own choices, in the face of unpopular opinion. This leads some situations to become out-of-control congregations that do whatever they want, and others to have the one or two willing spirits to feel isolated and lonely in the work of the kingdom.
Notice here, however, what Paul is doing. He is causing his fellow believers in Corinth to suffer grief for their situation. He admits this himself, and displays the weight of this ministerial work. But he does so because the situation in Corinth needs to take this journey in order to find the path of God's righteousness again. The important piece of this to remember is that the story of Corinth doesn't stop at the point of grief. Rather, Paul's difficult language to them causes a 'godlike' grief which leads them to repentance. And this is the ministry of reconciliation to which Paul has been speaking throughout the letter.
This, however, might not always be the case . . .
Although Paul's words had an impact of grief leading to repentance, there are undoubtedly many situations where nothing follows the grief. And a more 'worldly' grief is allowed to overtake any hope of repentance. Sometimes we can see this coming a mile away. It might make us cringe a bit, but it still remains necessary that those who minister do the work of the kingdom. After all, whether repentance follows is not ultimately about our conjecture of a given situation, but the Spirit's ability to transform hearts, minds and lives.