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Like a Boss, makin' copies and stuff....like a boss! Boss’s Day is celebrated every October 16th as a time to recognize and appreciate leaders in the workplace. Whether you're honoring a traditional bossman, a boss lady, or anyone in a leadership role, Bosses Day is about acknowledging hard work, vision, and guidance. While “bossy” has sometimes been used negatively—especially toward women—modern culture is reclaiming it. Today’s women bosses embrace confidence, strength, and leadership with pride. Celebrating Bosses Day is a chance to show gratitude and support for all types of bosses, especially women who lead with boldness and grace. Let your boss know they’re truly appreciated.