





If this was one of those “living or dead” scenarios, I’d have to go with Mark Twain. But as it may not be, and I wouldn’t want to have dinner with a box of bones, I’d say Chuck Palahniuk, or — in nonfiction — David Brooks.
I will admit that I’m quite jaded, but the only place I need my faith in people COMPLETELY restored is online. Almost anytime I interact with real people in the real world I come away with a sense that people are generally good and mostly trying to do right (in as much as they can determine what “good” and “right” mean in our complicated world.) However, as soon as one allows for anonymity, shittiness blossoms — whether that anonymity is due to the nature of the online world or because one is otherwise not interacting face-to-face or because one (while not strictly anonymous) is homogenized by life inside an echo chamber.
Huh, maybe I do need my faith in people restored because I guess I’m saying that people in the light of day are loveable but in the dark they slouch toward depravity. Maybe we’ll figure it out. For most of humanity’s existence, anonymity was not an option. There’s no hiding in a tribe. It’s all part of what our species is working out, I suppose. I suspect that most people if given the choice between having the ill-gotten gains of their anonymity or being truly and deeply seen would opt for the latter.

Diogenes the Cynic would be a hoot. Alternatively, Zhuangzi (莊子.) Obviously, my tastes run toward a philosopher that could teach me about how to be free, rather than to teach me some sort of rigorous approach to thinking. I’m stocked up on the latter, but in deficit of the former.
(I’m assuming this to be a “living or dead” question scenario. Usually, I prefer to talk to the living, but I don’t think modern academia has been good to the crazy sage philosopher. I might be able to find a Daoist hermit in a cave somewhere or maybe a Tibetan Nyönpa, but I couldn’t say what his or her name would be.)
First, I would have to figure out what my community is.
Captivate: The Science of Succeeding with People by Vanessa Van EdwardsAny successful standup comic. To gain a practical understanding of the downside and the struggle.
I wouldn’t care to be a billionaire because it would be just my luck that it’d be the day people wised up and the revolt began, and I could say the same thing with respect to world leaders.
Those who don’t take many things seriously, themselves least of all.