Paul said if he was going to boast (and he did like to boast), then he would boast about his weakness. His weaknesses were the only things about himself that he was willing to boast about. It made him glad to be weaker than his followers.
Paul was delighted to be weak, because boasting about weakness gave him the power of Christ. So being weak actually made him strong. But why would he want that power and strength, if he really liked being weak so much?
Paul boasted an awful lot about how tough he was for someone who’s supposed to be proud to be weak. And he even said he was ashamed to admit that he was too weak to tolerate the kinds of behavior that his followers tolerated.