Yesterday Letters of Note, one of the essential reads of the Internet, posted a letter from David Foster Wallace, who had just completed but not yet published Infinite Jest, to Don DeLillo, asking for advice:

Your note of 9/19 was heartening and inspiring and also made me curious about several things. I would love to know what changes in yourself account for “And discipline is never an issue (as it was in earlier years).” I would love to know how this education of the will took place — would that you could assure that it was nothing but a matter of time natural attritive/osmotic action, but I have a grim suspicion there’s rather more to it. I’d love to know how the sentence quoted above stands in relation to “The novel is a killer. I try to show it every respect.”

I think my fiction is better than it was, but writing is also less Fun than it was. I have a lot of dread and terror and inadequacy, now, when I’m trying to write. I didn’t used to. Maybe the terror is part of the necessary reverence, and maybe it’s an inescapable part of the growing-up-as-a-writer-or-whatever process; but it can’t — cannot — be the goal and terminus of that process. In other words there must be some way to turn terror into Respect and dread into a kind of stolidly productive humility.

I have a hard time understanding how Fun fits into the Dedication-Discipline-Respect schema. I know that I had less fun doing IJ than I did doing earlier stuff, even though I know in my tummy that it’s better fiction. I think I understand that part of getting older and better as a writer means putting away many of my more childish self-gratifying notions of Fun, etc. But Fun is still the whole point, somehow, no? … How do I allow myself to have Fun when writing without sacrificing Respect and Seriousness, i.e. going back to the exhibitionism and show-offery and pointless technical acrobatics?

(Note to the persnickety: I omitted two curse words.)

The importance of “fun,” which I interpret broadly as “enjoyment” or “fulfillment,” can’t be overstated. Life is short and often unforgiving of small mistakes, as it was when Steve Jobs briefly delayed his cancer treatment. As Jason Kottke (another essential read of the Internet) notes, Jobs’ death has been “inspiring some people to turn away from the lifestyle & choices that made Jobs so successful & inspiring in the public sphere and to attempt the path that Jobs did not.”

It brings to mind the famous interview of renown bankruptcy lawyer Harvey Miller on his decision not to have kids: “You have to have time to give them love, and I didn’t.” It’s fashionable to sneer at the concept of work-life balance, but, as I’ve discussed before, the concept is nothing more than a simple reminder that you cannot live your life devoted to work and family. You will have to make one yield to the other at critical times; the only part that matters is that you actually make the choice, instead of letting the choice happen to you.

Once you’ve reached the right level of balance, there’s the issue, as Wallace lamented, of “fun.” In our professional lives we obviously can’t have “fun” — not even defined broadly as “professional fulfillment” — all the time. It rarely pays the bills. It only sometimes develops a career. So how do we develop that “stolidly productive humility” that allows us to consistently do the work we need to do?

Via The Browser, another essential read, I recently saw an article about “flow,” described by Sally Adee at The New Scientist as “that feeling of effortless concentration that characterises outstanding performance in all kinds of skills,” which sounds to me just like the ‘stolidly productive humility’ that Wallace wanted:

[Psychologist Mihaly Csikszentmihalyi] interviewed a few hundred talented people, including athletes, artists, chess players, rock climbers and surgeons, enabling him to pin down four key features that characterise flow.

The first is an intense and focused absorption that makes you lose all sense of time. The second is what is known as autotelicity, the sense that the activity you are engaged in is rewarding for its own sake. The third is finding the “sweet spot”, a feeling that your skills are perfectly matched to the task at hand, leaving you neither frustrated nor bored. And finally, flow is characterised by automaticity, the sense that “the piano is playing itself”, for example.

Alas, the second and third encompass the very problem we’re trying to solve: the lack of “fun.” We need “autotelicity” and the “sweet spot” — a juxtaposition of jargon and plain English that Wallace probably would have appreciated — but how do we get there?

Ironically, it seems Wallace himself later found the answer he was looking for in his letter to DeLillo. As Maria Bustillos profiled at The Awl (an article included in Longreads, another essential read, Best of 2011 collection), “humility” was a particular obsession of David Foster Wallace’s, and a key to his success:

I gotta tell you, I just think to look across the room and automatically assume that somebody else is less aware than me, or that somehow their interior life is less rich, and complicated, and acutely perceived than mine, makes me not as good a writer. Because that means I’m going to be performing for a faceless audience, instead of trying to have a conversation with a person. […] It’s true that I want very much—I treasure my regular-guyness. I’ve started to think it’s my biggest asset as a writer. Is that I’m pretty much just like everybody else.

As Bustillos summed it up:

[A]ll his life Wallace was praised and admired for being exceptional, but in order to accept treatment he had to first accept and then embrace the idea that he was a regular person who could be helped by “ordinary” means. Then he went to rehab and learned a ton of valuable things from “ordinary” people whom he would never have imagined would be in a position to teach him anything. Furthermore, these people obviously had inner lives and problems and ideas that were every bit as complex and vital as those of the most “sophisticated” and “exceptional.”

After Wallace died by his own hand, his articles and books were catalogued, including his copy of Ernest Kurtz’s The Spirituality of Imperfection, in which he had underlined: “Humility—the acceptance that being human is good enough—is the embrace of ordinariness.” Wallace himself had summed up, and perhaps foreshadowed, the problem himself: “The parts of me that used to think I was different or smarter or whatever, almost made me die.”

Maybe those “parts” that thought he was “different or smarter or whatever” eventually did kill him. But he was, I think, on the right track: he was such a good writer, and was able to keep producing so much, because he keenly interested in the core of his work — the experiences of humanity — and did not assume that a stranger’s “interior life is less rich, and complicated, and acutely perceived than mine.”

Every line of work has, like writing, its fair share of tasks that have little apparent “Fun” and require “Dedication-Discipline-Respect.” Law is certainly no stranger to work that no one would ever want to do but which must be done. The solution, per Wallace, is to approach the job with humility, and to find the human side underlying each and every boring step of the law — the ‘rich, complicated, and acutely perceived’ justice of the situation — and use it to reanimate the task as the same epic contest of principles and interests and stories that the justice system is intended to resolve.

I return to my post about The Glamour and Glory of Being a Lawyer often because the story, to me, emphasizes the part of the law that lawyers need constant reminding about. Everyone can see how truly great it would be to prevail at trial. But we often forget that some of the biggest changes and the most fulfilling victories come from the most banal tasks, like, as in the story, reviewing foreclosure paperwork. It’s that sort of humility and appreciation for the humanity of the law that can propel us through the drudgery of what we really do.