If you must tell someone it is sarcasm, don't. — Nassim Nicholas Taleb

If you must tell someone it is sarcasm, don't.

Author: Nassim Nicholas Taleb

Insight: There's something deflating about having to explain your own joke. The moment you say "that was sarcasm," you've already lost—the humor collapses, the wit feels forced, and now the other person is just listening to you defend something that should have landed on its own. Good sarcasm works because it creates a small moment of shared understanding, a flicker of recognition between you and whoever gets it. The people who do get it don't need the explanation. The people who don't, well, explaining it won't really help anyway. This applies beyond humor, though. It's a useful test for whether something you're saying is actually clear or clever, or just confusing dressed up in irony. If you constantly find yourself clarifying that you were joking, the real problem might be that your delivery was muddled, or you're using sarcasm as a shield instead of a tool. There's also a subtler point lurking here: constantly explaining yourself—about anything—can be a sign you don't actually trust what you're saying. The strongest communication often requires the least footnotes. Sometimes the best move is to let what you said sit there and see who understands it naturally.

Source: The Bed of Procrustes: Philosophical and Practical Aphorisms, 2010