I have not read Infinite Jest. I have only read selected essays from Consider the Lobster and A Supposedly Fun Thing, a couple of short stories from Curious Hair, and a few other essays that I've found online that were published in various periodicals.
I say this partly as an apology, as the following opinion is necessarily based on lack of exposure. However, what I have
read has not left me wanting more.
I find his essays unpalatable. It's not because I think he was a poor writer; quite the opposite. He had an undeniable skill with the English language. There's a certain rhythm and cadence to his prose that is intimate, for lack of a better word. Reading his words leaves me with the feeling of being spoken to softly by an old friend, and he had unmatched insight and sensitivity.
But it was the insight of somebody whose perceptions were robbed of color by depression. Sure, it's easy to say that in hindsight, knowing how he battled with it, employed unusually powerful medication in vain, and was eventually robbed of his life by it. Even after compensating for that bias, I find the taste of depression in his work to be unmistakeable. For a lesser intellect, it's a mood disorder; with Wallace's penetrating intelligence in control, it is magnified to existential levels.
Many of his musings, particularly the title pieces of A Supposedly Fun Thing and Consider the Lobster, describe his difficulty finding pleasure in things that other people find pleasurable. His critical thoughts in the face of simple recreation strike me as particularly intense expressions of anhedonia and rumination. For a tennis player to say, "Midwest junior tennis was also my initiation into true adult sadness," in the context of his other essays, is almost like a cry for help.
There's a tension in mental health between looking at disease (such as depression) as a fault with the sufferer, endogenously, as a neurochemical imbalance or personality maladjustment; vs looking at it simple incompatibility with a social environment ill-suited to meet the sufferer's emotional needs. Is it the person who is broken, or is the person unhappy because the environment sucks?
This tension isn't simply academic, though. It's not just a topic for theorists and scientists. It's something that people with severe intractable depression have to deal with on a very personal level. For any activity, the basic question is, "Is this a thing worth doing?" which involves weighing the bad, painful, saddening, effortful aspects of an activity against the joy and happiness and benefit to mankind and long-term good. If you are habitually incapable of feeling pleasure, and - perhaps more importantly - incapable of feeling empathy for those who do feel pleasure, then your calculus is going to be dramatically imbalanced. The job of the therapist, and ultimately the job of the sufferer, is to dismantle the habitual focus on the negative and develop an ability to see the positive.
To a sufferer of depression, this sounds like willful ignorance. Why should I
look away from the abyss? The abyss is real
. Don't delude yourself! (Wallace's inability or refusal to ignore certain perceptions and cognitions is a recurring staple of his writing - it is the motivation behind the title and major themes of Consider the Lobster, for instance.) But this is an oversimplification - it's not about ignoring the bad entirely, but practicing mindfulness towards your the distortions of your own perceptions, how they can distract you from pleasures that are no less real, no less deserved.
Wallace was so eloquent that it is easy to forget that his descriptions of recreational activities were simply the interpretations of one man. His unhappiness with lobster eating, or cruises, or junior tennis each appear to reflect deep corruption bubbling under the surface of those respective activities. The sheer bleakness of his worldview is alluring. It's like a siren song, calling me to see the world of humanity as a wasteland. He was a man staring into the proverbial abyss every day of his life. Eventually that abyss swallowed him. I don't want to follow him there.