I like this idea. I'd make it the ability to schedule messages to anyone, not just me. And a special page where only I can see all my scheduled messages with the ability to change the date if I want.
For Example, I want to remind someone that irritates me just how much they irritate me after I'm dead and gone. I can write them a message and schedule it for 6 or 8 months out. Then if I die they will get it from dead me. If I am not dyin at that time I can change the date to another 6 or 8 months out.
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