I love scheduling emails to be sent later. Boomerang is great, but the free version limits how many emails you can schedule for later. I used another gmail extension called Send Later at one point, and a few years ago Google built a native version into gmail.

Recently I realized that this feature is great for another use case: replying difficult emails.

I have a bad habit of worrying about how to reply difficult emails. Sometimes it might be an important or delicate situation. Other times I’m not sure what to write, or simply don’t want to reply.

I’ll often mark the email as unread, where it sits there for hours or sometimes days, and then finally grit my teeth and deal with it. The degree that I don’t want to reply is roughly correlated with how long it sits in my inbox, and how many utils I lose from seeing it in my inbox repeatedly. This is not great, and it happens more often than it should.

The problem with an unprocessed email is that it’s an open thread in the back of my mind. I know it’s there, and it occupies a sliver of my RAM and ups my stress levels. Add a few emails together and the hit to RAM and stress can be non-negligible.

The solution I’m excited to try out is to reply these types of emails when I first read them, but schedule the reply to be sent later. This does two things:

  • The delay adds a bit of mental distance, so the reply isn’t as hard to write. After all, the recipient won’t see it immediately. This lowers the activation energy just a bit, and it’s a nudge in the right direction.
  • Sometimes I don’t want to reply an email too quickly. The extra delay directly addresses this.