David Foster Wallace on Why You Should Use a Dictionary, How to Write a Great Opener, and the Measure of Good Writing

“Readers who want to become writers should read with a dictionary at hand,” Harvard psycholinguist Steven Pinker asserted in his indispensable guide to the art-science of beautiful writing, adding that writers who are “too lazy to crack open a dictionary” are “incurious about the logic and history of the English language” and doom themselves to having “a tin ear for its nuances of meaning and emphasis.” But the most ardent case for using a dictionary came more than a decade earlier from none other than David Foster Wallace (February 21, 1962–September 12, 2008).

In late 1999, Wallace wrote a lengthy and laudatory profile of writer and dictionary-maker Bryan A. Garner. A correspondence ensued, which became a friendship, which sprouted a series of conversations about writing and language, eventually published as Quack This Way: David Foster Wallace & Bryan A. Garner Talk Language and Writing (public library) — an unparalleled record of the beloved writer’s relationship with language and with himself, and the source of his ideas on writing, self-improvement, and how we become who we are.

At one point, the conversation turns to the underappreciated usefulness of usage dictionaries. Wallace tells Garner:

I urge my students to get a usage dictionary… To recognize that you need a usage dictionary, you have to be paying a level of attention to your own writing that very few people are doing… A usage dictionary is [like] a linguistic hard drive… For me the big trio is a big dictionary, a usage dictionary, a thesaurus — only because I cannot retain and move nimbly around in enough of the language not to need these extra sources. As a teacher, about 90% of my job is getting the students to understand why they might need one.

True to his singular brand of intellectual irreverence, Wallace offers a delightfully unusual usage of the usage dictionary:

A usage dictionary is one of the great bathroom books of all time. Because it has the appeal of trivia, the entries are for the most part brief, and you end up within 48 hours — due to that weird psychological effect — actually drawing on exactly what you learned in some weird, coincidental way.

The conversation then turns to the structure of a winsome piece of writing:

A good opener, first and foremost, fails to repel… It’s interesting and engaging. It lays out the terms of the argument, and, in my opinion, should also in some way imply the stakes… If one did it deftly, one could in a one-paragraph opening grab the reader, state the terms of the argument, and state the motivation for the argument. I imagine most good argumentative stuff that I’ve read, you could boil that down to the opener.

With an eye to the Aristotelian tenet that a good story has a beginning, a middle, and an ending, Wallace agrees with Garner that “the middle is the biggest puzzle” and considers the perplexity of the middle:

The middle should work… It lays out the argument in steps, not in a robotic way, but in a way that the reader can tell (a) what the distinct steps or premises of the argument are; and (b), this is the tricky one, how they’re connected to each other. So when I teach nonfiction classes, I spend a disproportionate amount of my time teaching the students how to write transitions, even as simple ones as however and moreover between sentences. Because part of their belief that the reader can somehow read their mind is their failure to see that the reader needs help understanding how two sentences are connected to each other — and also transitions between paragraphs. […] An argumentative writer [should] spend one draft on just the freaking argument, ticking it off like a checklist, and then the real writing part would be weaving it and making the transitions between the parts of the argument — and probably never abandoning the opening, never letting the reader forget what the stakes are here… Never letting the reader think that I’ve lapsed into argument for argument’s sake, but that there’s always a larger, overriding purpose.

In how this larger purpose is conveyed, Wallace argues, lies the true measure of good writing:

Reading is a very strange thing. We get talked to about it and talk explicitly about it in first grade and second grade and third grade, and then it all devolves into interpretation. But if you think about what’s going on when you read, you’re processing information at an incredible rate. One measure of how good the writing is is how little effort it requires for the reader to track what’s going on. For example, I am not an absolute believer in standard punctuation at all times, but one thing that’s often a big shock to my students is that punctuation isn’t merely a matter of pacing or how you would read something out loud. These marks are, in fact, cues to the reader for how very quickly to organize the various phrases and clauses of the sentence so the sentence as a whole makes sense. […] The point where that amount — the amount of time that you’re spending on a sentence, the amount of effort — becomes conscious, when you are conscious that this is hard, is the time when college students’ papers begin getting marked down by the prof. […] One of the things that really good writing does is that it’s able to get across massive amounts of information and various favorable impressions of the communicator with minimal effort on the part of the reader. That’s why people use terms like flow or effortless to describe writing that they regard as really superb. They’re not saying effortless in terms of it didn’t seem like the writer spent any work. It simply requires no effort to read it — the same way listening to an incredible storyteller talk out loud requires no effort to pay attention. Whereas when you’re bored, you’re conscious of how much effort is required to pay attention.

Complement the altogether wonderful Quack This Way with Wallace on the meaning of life, death and redemption, the perils of ambition, and the greatest definition of leadership, then revisit this growing library of great writers’ advice on the craft.