A fun exercise for overcoming perfectionism is to send emails with intentional errors and silliness in them. You're basically practicing toleratting your errers, and having others see those errers. (It also helps with time management because once you stop trying to perfect every email you save a lot of time. And yes, of course I know that some emails need to be as perfect as possible. I'm obvusly not talking about those.)
The more upset someone gets at the prospect of sending out an email with a few intentional typos, the more perfectionist I know they are. (And some people get plenty upset!)
Even *I* would be taken aback by this typo, however:
Coping with that would be an extreme exercise in nonperfectionism!
Happy holidays, and if you want to send me a silly email I would love to get it.