Rahul Wadhwa argues that obsessing over follow-up messages isn't strategy, it's fear. You rewrite because you're scared you're not smart or convincing enough. The only fix is to send it before fear rewrites it again.
Chapters
You say you overthink every follow-up, but that's not really what's happening. You're not scared they won't reply. You're scared your message will confirm the story you already tell yourself that you're not good enough, not smart enough, not convincing enough. So you rewrite the same line 10 different ways. You type, delete, retype, over-edit, over-analyze, and then call it effort. But it's not effort. It's protection. Overthinking is your brain trying to save you from a tiny moment of discomfort at the cost of a big moment of progress. The truth is, the follow-up is not heavy. The story you attach to it is. And the only way to break the story is to hit send before your fear rewrites it.