Since I told my wife I wanted to read more David Foster Wallace, she got me "Consider the Lobster," for my birthday. It's a collection of his essays. She didn't know the first one was a revulsive 50-page rant on porn. I read "Big Red Son," 3 times, not only because it's a Gonzo-style dive into a 1998 adult film conference, but because several times a page, Wallace blows my mind as a writer.

Wallace takes something that you've always seen in black-and-white and turns it into a color photo.

In the circle of writers I know online, we use an acronym called "POP Writing"– Personal, Observational, and Playful. Wallace is a master at crafting memorable observations. He uses relatable metaphors, makes unlikely associations, and looks under the rocks that most people walk past. He re-wires how you see the world. Pencil in hand, I scribbled all over his essay to figure out how he does it.

Here are 6 ways you can inject memorable observations into your writing (also, warning: R-rated excerpts ahead):

1. Express scale through metaphors, not numbers.

"Let us not forget Vegas's.. beating heart.. Caesars Palace. The granddaddy. As big as 20 Wal-Marts end to end. Real marble and fake marble, carpeting you can pass out on without contusion, 130,000 square feet of casino alone."

Most people don't have a concept of how big 130,000 square feet is. I'm an architect, and it's even fuzzy for me. But since Wallace uses "Wal-Marts" as a unit of scale, it's easy to grasp the magnitude of this Vegas casino. Metaphors help the reader see what you mean. I drive by Wal-Marts in strip-malls all the time. They're massive. Now imagine twenty of them side-by-side. Point made.

2. Time-travel through history to get perspective.

"Whether the framers of the US Constitution might, in their very wildest imaginations, have been able to foresee things like Anal Virgins VIII or 900-666-FUCK when they were thinking of expression they wanted to protect is obviously a thorny question and outside this article's purview."

Time brings odd mutations. Rarely do we think of George Washington and hardcore porn in the same thought. These references around freedom of speech are centuries apart. It's a superpower to take an idea out of context and find historical parallels. You'll find combinations that are surreal, funny, and thought-provoking.

*Side note: This riot of a sentence is a footnote in his essay! (I finally get why Wallace's footnotes are so legendary).

3. Make your comparisons human.

"..Far and away the CES's most popular venue, with total attendance well over 100,000 every year, is.. the Adult Software exhibition, despite the fact that the CES itself treats the Adult tradeshow kind of like the crazy relative in the family and keeps it way out in what used to be the parking garage of the Sands hotel."

Most people have a crazy aunt who's bound to make a scene at Thanksgiving. Our day-to-day lives are filled with situations like this. Wallace uses them like a codex. He translates the complexities of the world through situations that everyone gets. When you're at the scale of institutions, philosophies, theories, and frameworks– try bringing it back down to the human. It's the ultimate context clue. You can make sense of the excerpt above without knowing what CES stands for.

4. Unpack the meaning behind words.

"But of course we should keep in mind that vulgar has many dictionary definitions and that only a couple of these have to do w/ lewdness or bad taste. At root, vulgar just means popular on mass scale. It is the semantic opposite of pretentious or snobby.. It is Nielsen ratings and Barnum's axiom and the real bottom line. It's big, big business."

Words grow stale, fast. After using one a hundreds times, it's easy to settle in to the most common definition. It's natural and practical. But words often have deeper wells of forgotten meaning. When you dive into alternate-interpretations, translations, and origins, you'll be surprised with what you find. Sometimes these discoveries shed light on our culture. Since everyone has heard the phrase, "sex sells," the definition of "vulgar as popular" makes complete sense.

5. Reveal the backstory of ordinary objects

"All of 1998's marginal print journalists are together at Table 189 at the very back of the ballroom. Most of these reporters are from the sort of men's magazines that sit shrink-wrapped behind the cash registers of convenience stores, and they are a worldly and jaded crew indeed, but Schimmel gets a couple of them-- whose noms de guerre are Harold Hecuba and Dick Filth-- laughing so uproariously that people at the Anabolic Video table nearby keep looking over in annoyance."

I never put much thought into what goes on behind a grimy gas station magazine. Wallace confirms what you'd expect– editors with filthy pseudonyms, sitting around a table behaving like apes. When writers add extra layers of depth, it changes how readers see the world. Think about all of the things you and your reader come across on a given day– and realize how rarely we investigate their backstories.

6. Debunk the assumptions of our culture

"Because porn films' worlds are so sexualized, with everybody seemingly teetering right on the edge of coitus all the time and it taking only the slightest nudge or excuse-- a stalled elevator, an unlocked door, a cocked eyebrow, a firm hand-shake-- to send everyone tumbling into a tangled mass of limbs.. there's a bizarre unconscious expectation/dread/hope that this is what might happen in Max Hardcore's hotel room. [I] find it impossible to overemphasize the fact that this is a delusion. In fact.. [it] makes no more sense than it would make to be hanging out with doctors at a medical convention and to expect that at the slightest provocation everyone in the room would tumble into a frenzy of MRIs and epidurals."

The fusion of sex and film leads to ambiguity. Even though porn-watchers known they're watching entertainment, they may have a delusional sense of what happens off-camera. A good writer can poke holes in theses invisible assumptions. Our culture is filled with situations where beliefs get hypnotically transferred. Writers have an opportunity to shed light on beliefs that are unclear, unspoken and unarticulated.

tldr; Make unlikely associations. Look behind the scenes.

Dean's List

Wallacisms: The Art of Memorable Observations