Dear Dr. Trainwreck, I've been relatively successful as an artist, but still, I often feel less than. In a world that is becoming more inclusive and understanding of diversity, economic diversity is still somehow frowned upon. I grew up pretty poor in LA. I've had several friends decide not to introduce me to their higher-net-worth friends or collectors. They say that explicitly. I hate to make...

I have a notebook from this obnoxious British heritage brand called Smythson, and on the front cover it says, in gold leaf, “Charming in Character and Appearance.” The only thing in this particular notebook is pages upon pages of what I call “unforgivable things”: confusing Frankenstein and Frankenstein’s monster; referring to anything as “edgy"; when a bartender asks me, “Vodka or gin?” when I...