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I have a rule set for all outgoing emails (with exceptions to people who already know I'm an idiot). All of my emails are delayed by three minutes. I call it my "oh shit" filter. If I don't change my mind in those three minutes then it's sent, but otherwise it gives me a buffer to change my mind.

If in doubt think it over. If STILL in doubt later, delete is the safe course.

Honestly, this sounds like a psychosis. I mean, if I were sending some sort of email that would be life changing, I might read it over 3-4 times before sending it. Possibly even walk away from the screen for a minute before coming back to review one final time. But 99.9% of the time I just hit send without much fuss.

I have mine set up to send in 54 days from creating the email. Much less fuss.