Recommendation: I enjoy the writings of Daniel M Lavery (previously Daniel Mallory Ortberg of The Toast). He writes fun but thought-provoking things about his white, queer, American, academic/writerly transmasculine experience.
He has a memoir out called "Something That May Shock and Discredit You", which I haven't read yet, as well as a blog. The blog has some "paid subscribers only" posts, but many posts are free. Sometime when I'm less socially anxious I may take Lavery up on his offer to share individual paid posts for free with people in financial hardship.
Lavery is also the advice columnist "Dear Prudence" on Slate.com, but tbh I haven't enjoyed those as much. Every other post is behind a paywall and I don't always agree with his advice. Still worth mentioning, though!