Two selections of his incessant prattling caught my attention.
Bob Chipman said:
We “work on” a lot of things, but the number one thing I find myself trying (often failing) to get a handle on is a deeply painful sense of emptiness and emotional need.
I would almost sympathize with Bob here, but I know that it would be a waste. This emptiness might be from the fact that he knows that on some visceral level that his "work" give him no joy or fulfillment. Why would it? Does anyone remember Shakespeare's critics four centuries after the Bard shuffled off this mortal coil? Of course not! No respectable university or college course is going put his videos, blog posts, or his shitty book down as required reading on the syllabus.
As for the emotional need: could it be validation? Bob appears to be seeking affirmation from all the wrong source. Any "friendship" he seeks to have with Zoe Quinn, Brianna Wu, etc. will be transactional and completely conditional. He was willing to throw his boss and friend under the bus for ideology's sake and Quinn/Wu/Whoever would do the same to him in a Boston minute. Additionally, he seeks emotional validation of the Elites or "Intellectuals" who will never recognize his so-called gift and I imagine that is a factor in why Bob lashes out at "the Wasteland." He has "worked" so "hard" to get where he is now, but it is will hanging by a thread because he could still get fired or lose his Patreon bucks.
Maybe he is feeling this harsh bout of imposter syndrome because that is what he is: an imposter. He claims that he is this insightful and witty renaissance man of refined tastes and sublime intellect, but he is just one of the rubes. His friendships are superficial; no studio is going to listen to his ideas; and his knowledge of pop culture is more feeble than he would care to admit.
But wait! There's more.
Bob Chipman said:
I feel alone a lot. Not “impostor” alone or “monophobic” alone or evenly necessarily “lonely” (though I do feel that more and more as the years pass – it used to be less pronounced, but I grew up in a busy house and now… it’s just me, more and more.) But isolated, misunderstood, suspicious that I’m (more) disliked than I’m told I am and – always – on the precipice of losing whatever stability, friends, colleagues, advancement, growth, status, etc I’ve managed to achieve for myself.
Isolated? For Christ's sake, Bob! You were at your sister's wedding in Cancun--surrounded by family--and you were hunched over your phone at the table. If you felt isolated, then that's on you. Imagine the kind of life you could have if you weren't such an angry sperg. And no, you're not misunderstood. You make it crystal clear to anyone with half a synapse that you are a spiteful, petty, and hateful little man who takes delight in the misfortunes of those you detest and exploit the suffering of others for your self-aggrandizement. There is no need to be suspicious of being disliked. You ARE disliked by many people that are better than you or your sociopathic cohorts.
Spare me the self-pity, Bob. You don't really want to change. You're too comfortable in your self-inflicted misery.