To find a solution to or help recover from a particularly difficult situation, especially one created by a mistake, misfortune, or ill judgment. The line cooks had a huge amount of orders to fill, so the manager helped them plate the food to dig them out of a hole. My little brother is always getting in trouble with the law, and it's always me who has to go dig him out of a hole! We made a few bad investments last year, and we've been digging ourselves out of a hole ever since.