eg Tom is out of pocket. He has paid for something (with money out of his own pocket) that someone or some organization should have paid for. He will be reimbursed in normal cases. eg A salesman pays with his own money for a client's lunch. He is out of pocket. He then submits an expense claim to his company, and they pay him ba
Well Urban Dictionary seems to know about it, but says (in Definition 1) it's "a new business catchphrase" but is incorrect. Then (in definition 2) it says "old businessmen" use it that way. (Bolding is my own)