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You don’t need a guide to tell you the ettiqete on sending an email at 2 AM, but just in case…
DON’T SEND IT.
Just because you’re up doesn’t mean they are. You’re much better off waiting until the morning. Well… their morning. Don’t forget to check what time zone the reader is in.
As far as what time of day, or what day of the week? There are a few mixed signals out there, but SuperHuman has provided the most compelling research I’ve seen. My recommendations are a blend of their research and others, and empathy for the reader.
You should try to email in rhythm with the reader’s schedule.
Miss your window? Catch them between meetings aka “between the fives”: