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The actual sentence is: "Keep in mind that you can't apologize your way out of being an ass." What does it mean?

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  • "Being an ass" is being really annoying and, usually, self-centered, being totally insensitive to the needs and feelings of other people. – Hot Licks Jul 29 '15 at 23:48
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    The point, I think, is that, whereas some difficult social situations can safely be navigated by using a combination of caution and humility and (in the worst case) profuse apologies, the underlying condition of assness is nonnegotiable. – Sven Yargs Jul 30 '15 at 8:01
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Try parseing the sentence differently, and it makes more sense. To "Apologise your way out of" a problem is to make a bad situation better by apologising for an earlier mistake. The sentence is saying that it is of no use to apologise if people still think you are an ass.

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    No, it is saying that apologising does not magically transform people's present perceptions about you (based on your poor track record). OP's quote is from Rework: Change the Way You Work Forever by Jason Fried, David Heinemeier . Two sentences after OP's is: 'Everything you do before things go wrong matters far more than the actual words you use to apologise.' – Edwin Ashworth Dec 24 '14 at 10:55
  • It's like "If you put lipstick on a pig - it's still a pig." – Oldbag Dec 24 '14 at 11:06
  • @Edwin Ashworth - I've edited my post so hopefully it's clearer. – Simon B Dec 24 '14 at 11:18
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It's an idiom.

"He made his way out of the church."

"She argued her way out of receiving a parking fine."

"He wheedled his way out of doing the washing up."

"She's so weak, she couldn't fight her way out of a paper bag."

etc.

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