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Morendil comments on The True Rejection Challenge - Less Wrong
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Keep a private blog, and consider posting to a public one those essays that you're particularly proud of.
See 3), I have an ugh field around looking at my writing that means if I waited until I felt proud of something I wrote I would never publish anything. My current workaround, which I've used for academic coursework, involves pre-committing to aiming for a minimum level of quality rather than trying to be happy with my work. After sufficient time has passed since writing, I can usually look at it more objectively. Which suggests that I should commit to posting privately and then revisiting posts a week or two later after the ugh field has faded
Maybe set things up so that, once you write something for the blog, it's automatically released to the public three weeks later unless you come back at least one week after initially writing it and manually keep it private? That way, the embarrassment acts as a reminder to review and revise.