What does 2 Corinthians 11:16 mean?

Corinthian culture was competitive. This was true in sports, but also in philosophy and performance. People expected speakers to be entertaining, dramatic showmen. They assumed such men would boast about their accomplishments, their education, and their skillful arguments. They also expected these intellectual competitors to tear down their philosophical opponents. That was a sign of strength and confidence in one's position.

Paul's contrasting approach seems to have confused the Corinthians. In person, especially, he may not have been impressive. He also tended not to brag about himself or his own achievements. He nearly always pointed to the power of Christ and the grace of God, while openly acknowledging his own suffering. In the culture of Corinth, this looked like weakness. Perhaps this was why the Corinthians were so captivated by Paul's impressive-sounding, confident opponents.

Beginning in this verse, Paul, for the sake of argument, agrees to compete on the terms of his opponents and the culture. He asks his readers not to think he is really so foolish as to talk as a boastful fool would talk—his intent is merely to make a valid point. When he does start "boasting," in the following verses, his boasts continue to be about things beyond his control: his birth, his life before Christ, his suffering, the things God has shown him, and God's strength through him. Paul makes a mockery of his opponent's self-glorifying boasting by imitating it to reveal his own weakness and God's great power.