I have a major habit of emailing myself. I don’t consider it a huge problem really, but it is just dumping something at my future-self to deal with without much structure. So I’ve been weaning myself off it.
I use Things for my to-do lists, which are structured, and have due dates and context. So if the thing I’m emailing myself really belongs there, I put it there.
But more importantly, there is a good chance the thing I’m emailing myself is a tiny, tiny thing. It’s a reminder to do something else, like “text the landlord about the drawer.” It seems silly thinking about that, because writing myself an email about that takes about just as long as writing the dang text itself.
I forgive myself to some degree, because writing to yourself is very low-stakes. Communicating with another person is higher-stakes. You need to make sure you understand yourself exactly what you are saying and then make sure you say it in a clear way. It’s not every second of the day you’re in that headspace.
Still. I’m trying to use the Getting Things Done-rooted 2 minute rule. If the thing takes less than 2 minutes to do, just do it. That includes actually writing the email and not dumping it on future-me. So far so good. I prefer keeping those tiny-weenie things off actual to-do lists, lest they become more overwhelming than they really are.