Personal Essays

My Life in Jest

When floating through post-collegiate limbo, you can use an anchor. Recalling when a very large book played a very large role in life.

When David Foster Wallace died last weekend, on the eve of my 29th birthday, I tried to avoid seeking some kind of selfish symbolism in the timing of the tragedy. But that his life should end just as my 30th year was beginning seemed crudely coincidental.

For a dozen years, Infinite Jest—impenetrable, self-righteous, kind of absurd—has held a special appeal to overeducated twentysomethings harboring a certain amount of bemused future-dread. Wallace’s compassionate satire and enviable wit attracted post-adolescents reeling from that first bitch-slap of the real world, and trying to shake off—or hold on to—their impossible expectations for themselves and their society.

I bought my secondhand (of course) copy of Infinite Jest at the end of college, with that kind of self-congratulatory, ready-to-conquer-the-world optimism provoked by graduation. At the time, I’d no doubt imagined a future of Work that Made a Difference, supplemented by Important Casual Reading. But for months after graduation, the book sat unread on the shelf, haughty and huge, its fat, orange spine glowing like a construction-zone caution sign.

It was 2001, and the world had other things in mind than being conquered by optimistic, educated me. Things crumbled and fell apart that fall, and not just because for the first time in 18 years I didn’t have a new notebook or a life purpose when the leaves began to change. By October I was unemployed, couch-surfing around greater Boston, and digging myself into a credit hole from which I’ve yet to recover. I had a festering wound of a broken heart buried under layers of guilt for feeling sad; after all, a terrible new world had revealed itself, one that made my privileged post-college problems seem all the more petty and inconsequential.

I was stuck in a structureless limbo between my old adolescent, student life and the new routines of adulthood. I didn’t have a class schedule or a paper due, but I couldn’t find a job or sign a lease, either. And so, I floated. I spent whole days in cafes, drinking copious amounts of coffee and staring out the window. I took epic walks, traced the length of Massachusetts Avenue from Somerville to the South End. I tried to lose myself, as fledgling adults are wont to do, by drinking cheap beer and dancing furiously to songs that were hits when I was a comfortable and confident 8-year-old.

But I wasn’t much of a drinker or a dancer; I needed something more. I needed a project to absorb the hours, something that would anchor and entertain me. And there it was, gaudy and overconfident, the favorite book of the boy who broke my heart. This was dangerous territory, I knew, but I had no choice: I heaved the blue and orange behemoth off the shelf and held on for dear life. If I could not conquer the world then I was going to conquer 1,079 pages of unwieldy modern literature.

I threw myself in, and was consumed. It was a prematurely monogamous relationship, bordering on co-dependent, too much too soon. I brought it with me wherever I went. I talked out loud to the book, and this conversation was complex. It went way beyond the narrative—tennis school, Canadian freedom fighters, toxic waste, a science-fantastical Boston metro system, entertainment, advertisement, addiction—the plot points were mere footnotes to my relationship with the text.

I walked the streets of Cambridge, Allston, and Infinite Jest all at once. Ceramic virgins, Inman Square, dogs behind chain-link fences, Green Line train tracks: This was my landscape on the page and off. I got mixed up. Sometimes on a hazy, subconscious level I couldn’t tell if something I remembered, an image I had, was from the book or from my life. Sometimes I accidentally referenced the book in real life, used it as a basis for small talk, or bored my friends with obsessed musings, like a girl, again, stupidly infatuated.

The doctor felt around and said it was nothing. “Have you been carrying something heavy around?” she asked. “Maybe drinking a lot of caffeine?”

There was a din of voices there. In addition to Hal and Gately and Joelle Van D., the guy who’d owned the book before me and made irritating pseudo-intellectual notes in the margins was there, and the boy whose favorite book it had been was there, all insensitive and condescending, and DFW himself too, as a kind of smart, saintly, stained-glass incarnation of that boy—on steroids. The lot of us argued, made pretentious comments, and sneaked around behind each other’s backs with deceit and malice, curiosity, and compassion. We were just trying to figure each other out, for those thousand pages, trying to find our stories in the narrative.

In my dreams at the time I screamed, sobbed, and threw furniture as my subconscious processed the loss my privilege-guilt wouldn’t let me acknowledge. I developed a chronic pain in my right shoulder and convinced myself my seething rage had finally crystallized into a tumor. I went to a clinic to get it checked out, but the doctor felt around and said it was nothing. “Have you been carrying something heavy around?” she asked. “Maybe drinking a lot of caffeine?”

By December, Gately was laid up in the hospital with a gunshot wound, refusing narcotics, and I had developed the decidedly less dramatic (and very post-adolescent) affliction of chronically infected wisdom teeth. I didn’t have insurance to cover general anesthesia for their extraction, but the sympathetic, elderly oral surgeon I’d found in the Yellow Pages threw in nitrous oxide for free at the last minute. Still, I kicked and cried as he wrestled the teeth from my mouth. Under the gauze of the drug I hovered in pain with Gately, haunted by wraiths and the disembodied voices of nurses. I couldn’t tell if I was dead or alive, me or him, fiction or real.


There are books I’ve loved more than Infinite Jest, but there are none I found so harrowing to live through. When friends ask whether it’s “worth” reading, I have a hard time answering. I have no idea what it would be worth to them. I lived in those pages, and learned so much. I learned about humans, and tennis and crack and I learned new ways of thinking, and of thinking about thinking. But I also learned about myself. What would someone else take from the story? I have no idea. What would it be like if I picked it up next week? No doubt, a different book altogether.

This is a novel that blares at you like a television possessed by a poltergeist; it doesn’t address you sternly from a lectern under a spotlight, telling you what you must think, what you must learn. It’s up to you to wrestle control of the remote, or to give yourself over to the current and be carried along. There are chunks of prose so dense your mind can’t help but wander, inserting trivialities from your subconscious like invisible footnotes. And there are characters so real, sentences so funny and touching that they stick with you when you shut the book and go about your real-world day.

I was recovering from my oral surgery when I finished Infinite Jest and stuck it back into its cavernous spot on the shelf. I had a new room in a house full of gender-bending, hallucinogen-experimenting roommates, a crush on a barista at my favorite cafe, and a new job—in retail. I was drained and sore, elated and light, and maybe it was the Percocet, but I felt ready to take on the world again. As when Hal is hit, on page 896, with a “telescopically self-conscious panic…[e]verything came at too many frames per second. Everything had too many aspects. But it wasn’t disorienting. The intensity wasn’t unmanageable. It was just intense and vivid…. The world seemed suddenly almost edible, there for the ingesting.”

Only it wasn’t the old world, where right answers got good grades and hard work yielded certificates of accomplishment. In this one, you had to carve a twisted route through distractions and diversions, and read between the lines. There were horrible moments, and moments of simple, brilliant beauty, and there was hopelessness and there was hilarity—sometimes at the exact same time.