Dear reader: cringe as a signal of taste

The first of a series answering curiosities that readers send in

“I think I write okay. I know I really enjoy it. And I couldn't agree more with your views on writing with conviction. But I really struggle with overcoming this fear of sounding inauthentic, pretentious, or worst of all...cringey. Did you also feel this way when you first started writing? What helped you break past this? How do you deliberately build ‘…