Generally this refers to doing something that is usually not allowed but sometimes if you ask you can get permisson. So if you want to do this thing the question you ask yourself is; "should I ask for permission and maybe get turned down or should I just go ahead and do it and ask for forgivness afterward. Example: When Mary (a young teenager) goes out on a date the rule is she has to be home by 9 pm. However tonight there is a big party going on that will surely last till midnight. Should she ask permission to stay out late tonight or should she just go ahead to the party, come home at midnight and say she's sorry. The way I used the phrase was; "its easier to ask forgivness then to ask for permission". One of my favorite little phrases.
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