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Web check out our boss's day sign selection for the very best in unique or custom, handmade pieces from our signs shops. Web boss's day (also written bosses day or boss' day) is generally observed on or around october 16th in the united states. It has been pitched as a day for employees to thank their bosses for being kind and fair. Web october 16 is national boss’s day, a chance to celebrate the people who keep us gainfully.