When you are monitoring yourself in real-time, like when using headphones for tracking, the difference in perception isn't quite as bad as when listening back. When you're singing, you still are getting that bone conduction and chest resonance Bob mentions. It's only your ears that get what the headphones are putting out.
Maybe it's because I've done it so much, but I never really noticed much "disconnect" in my voice with real-time monitoring, like headphones or stage monitors. Certainly not to the same extent it took getting used to hearing back my recorded voice later.
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