I’ve now made my argument for why deep work supports abilities that are becoming increasingly important in our economy. Before we accept this conclusion, however, we must face a type of question that often arises when I discuss this topic: What about Jack Dorsey?
Jack Dorsey helped found Twitter. After stepping down as CEO, he then launched the payment-processing company Square. To quote a Forbes profile: “He is a disrupter on a massive scale and a repeat offender.” He is also someone who does not spend a lot of time in a state of deep work. Dorsey doesn’t have the luxury of long periods of uninterrupted thinking because, at the time when the Forbes profile was written, he maintained management duties at both Twitter (where he remained chairman) and Square, leading to a tightly calibrated schedule that ensures that the companies have a predictable “weekly cadence” (and that also ensures that Dorsey’s time and attention are severely fractured).
Dorsey reports, for example, that he ends the average day with thirty to forty sets of meeting notes that he reviews and filters at night. In the small spaces between all these meetings, he believes in serendipitous availability. “I do a lot of my work at stand-up tables, which anyone can come up to,” Dorsey said. “I get to hear all these conversations around the company.”
This style of work is not deep. To use a term from our previous section, Dorsey’s attention residue is likely slathered on thick as he darts from one meeting to another, letting people interrupt him freely in the brief interludes in between. And yet, we cannot say that Dorsey’s work is shallow, because shallow work, as defined in the introduction, is low value and easily replicable, while what Jack Dorsey does is incredibly valuable and highly rewarded in our economy (as of this writing he was among the top one thousand richest people in the world, with a net worth over $1.1 billion).
Jack Dorsey is important to our discussion because he’s an exemplar of a group we cannot ignore: individuals who thrive without depth. When I titled the motivating question of this section “What About Jack Dorsey?,” I was providing a specific example of a more general query: If deep work is so important, why are there distracted people who do well? To conclude this chapter, I want to address this question so it doesn’t nag at your attention as we dive deeper into the topic of depth in the pages ahead.
To start, we must first note that Jack Dorsey is a high-level executive of a large company (two companies, in fact). Individuals with such positions play a major role in the category of those who thrive without depth, because the lifestyle of such executives is famously and unavoidably distracted. Here’s Kerry Trainor, CEO of Vimeo, trying to answer the question of how long he can go without e-mail: “I can go a good solid Saturday without, without… well, most of the daytime without it… I mean, I’ll check it, but I won’t necessarily respond.”
At the same time, of course, these executives are better compensated and more important in the American economy today than in any other time in history. Jack Dorsey’s success without depth is common at this elite level of management. Once we’ve stipulated this reality, we must then step back to remind ourselves that it doesn’t undermine the general value of depth. Why? Because the necessity of distraction in these executives’ work lives is highly specific to their particular jobs. A good chief executive is essentially a hard-to-automate decision engine, not unlike IBM’s Jeopardy!-playing Watson system. They have built up a hard-won repository of experience and have honed and proved an instinct for their market. They’re then presented inputs throughout the day—in the form of e-mails, meetings, site visits, and the like—that they must process and act on. To ask a CEO to spend four hours thinking deeply about a single problem is a waste of what makes him or her valuable. It’s better to hire three smart subordinates to think deeply about the problem and then bring their solutions to the executive for a final decision.
This specificity is important because it tells us that if you’re a high-level executive at a major company, you probably don’t need the advice in the pages that follow. On the other hand, it also tells us that you cannot extrapolate the approach of these executives to other jobs. The fact that Dorsey encourages interruption or Kerry Trainor checks his e-mail constantly doesn’t mean that you’ll share their success if you follow suit: Their behaviors are characteristic of their specific roles as corporate officers.
This rule of specificity should be applied to similar counterexamples that come to mind while reading the rest of this book. There are, we must continually remember, certain corners of our economy where depth is not valued. In addition to executives, we can also include, for example, certain types of salesmen and lobbyists, for whom constant connection is their most valued currency. There are even those who manage to grind out distracted success in fields where depth would help.
But at the same time, don’t be too hasty to label your job as necessarily non-deep. Just because your current habits make deep work difficult doesn’t mean that this lack of depth is fundamental to doing your job well. In the next chapter, for example, I tell the story of a group of high-powered management consultants who were convinced that constant e-mail connectivity was necessary for them to service their clients. When a Harvard professor forced them to disconnect more regularly (as part of a research study), they found, to their surprise, that this connectivity didn’t matter nearly as much as they had assumed. The clients didn’t really need to reach them at all times and their performance as consultants improved once their attention became less fractured.
Similarly, several managers I know tried to convince me that they’re most valuable when they’re able to respond quickly to their teams’ problems, preventing project logjams. They see their role as enabling others’ productivity, not necessarily protecting their own. Follow-up discussions, however, soon uncovered that this goal didn’t really require attention-fracturing connectivity. Indeed, many software companies now deploy the Scrum project management methodology, which replaces a lot of this ad hoc messaging with regular, highly structured, and ruthlessly efficient status meetings (often held standing up to minimize the urge to bloviate). This approach frees up more managerial time for thinking deeply about the problems their teams are tackling, often improving the overall value of what they produce.
Put another way: Deep work is not the only skill valuable in our economy, and it’s possible to do well without fostering this ability, but the niches where this is advisable are increasingly rare. Unless you have strong evidence that distraction is important for your specific profession, you’re best served, for the reasons argued earlier in this chapter, by giving serious consideration to depth.
Chapter Two
Deep Work Is Rare
In 2012, Facebook unveiled the plans for a new headquarters designed by Frank Gehry. At the center of this new building is what CEO Mark Zuckerberg called “the largest open floor plan in the world”: More than three thousand employees will work on movable furniture spread over a ten-acre expanse. Facebook, of course, is not the only Silicon Valley heavyweight to embrace the open office concept. When Jack Dorsey, whom we met at the end of the last chapter, bought the old San Francisco Chronicle building to house Square, he configured the space so that his developers work in common spaces on long shared desks. “We encourage people to stay out in the open because we believe in serendipity—and people walking by each other teaching new things,” Dorsey explained.