I think by “boasting in weakness” Paul means that we ought to own our weakness. To own up to it. It does not mean throwing a pity party. It does not mean having a martyr’s complex. It does not mean being Debbie Downer. It does not mean the kind of self-conscious self-deprecation that actually brings more attention to one’s self. It is not a false humility. It simply means owning up to the reality that if it were not for Jesus Christ, everything about us would blow apart in the gale-force hurricane of our own sin and frailty.
