The man who rolls up his shirt sleeves is rarely in danger of losing his shirt.

This proverb-like saying links “rolling up one’s sleeves” (getting to work, taking practical action) with “not losing one’s shirt” (avoiding ruin or heavy losses). Its point is that people who actively engage—especially in hands-on labor, problem-solving, or management—tend to notice risks earlier, control outcomes better, and are less likely to be blindsided by failure. The humor comes from the literal image of protecting a shirt while working and the idiom about financial loss. As a piece of folk wisdom, it praises diligence and personal responsibility over passivity, implying that effort and attentiveness are forms of self-protection in both business and life.