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On Writing Immersive Nonfiction & Idea Generation with 'The Fifth Risk' Author Michael Lewis

Author Michael Lewis of The Big Short, Moneyball and his latest, The Fifth Risk, lays out his formula for generating ideas and writing immersive nonfiction in this extended Writer's Digest interview.

Whether by luck or an innate synchronicity, Michael Lewis often finds himself on the precipice of moments that shift the axis just slightly—but reshape the world in their wake.

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Through the collapse of the housing market in 2010’s The Big Short, the introduction of big data to the nation’s pastime in 2003’s Moneyball, or the root of behavioral economics in 2016’s The Undoing Project, Lewis rides the seemingly imperceptible edges of epochs to chronicle the point where the tide ebbed, often discovering riches hidden underneath.

It’s a skill he’s been honing for decades. The 58-year-old nonfiction bestseller first cut his narrative teeth as a bond salesman, witnessing the heady descent of the investment bank Salomon Brothers from Wall Street juggernaut to financial sector cautionary tale, detailed in his 1989 debut, Liar’s Poker.

Inherent curiosity ultimately led Lewis to cover several notable trends that helped define the late 1990s and early 2000s, fortuitously capturing them at their height. From the dot-com boom in The New New Thing (1999) to the rise of offensive linemen in quarterback-protection football in The Blind Side (2006), Lewis blends immersive reporting with his trademark observational wit, fueled in part by an unlikely cast of characters that drive the narrative with panache. His ability to distill complex topics has translated well to the silver screen: Three of his books have been adapted into star-studded films, collecting Academy Awards nominations and trophies along the way. The late, great Tom Wolfe—himself a sage of narrative nonfiction—once said of Lewis: “In my pantheon, [he] is the highest-ranking young writer.”

For his latest, The Fifth Risk, Lewis has centered his focus on the most vulnerable point of the Republic: the peaceful transition of power between presidential administrations. By chronicling the inauguration of President Donald Trump and the somewhat chaotic assembly of his cabinet, Lewis reveals the inner workings of some of the most overlooked federal agencies and how they impact our daily lives.

Providing abundant detail into facts from how the Department of Commerce predicts the weather to the Department of Energy’s role in preventing nuclear war, Lewis narrates his civics journey through the opaque avenues in which the government serves its citizens. Set against the backdrop of the early days of the Trump administration, he also details the potential peril that can lurk when those operations are overlooked or left in disrepair by absent leadership.

Lewis sat down with Writer’s Digest to talk about The Fifth Risk, his approach to structuring a narrative, and the genesis of book-length ideas.

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You have a gift for taking the Byzantine and making it both accessible and entertaining to readers, but the federal government is a uniquely complex beast. What made you want to explore that subject?

When Trump was elected, I had this sinking feeling and it took me a while to identify what was bothering me. I had just come off writing The Undoing Project, which was in part about how people are really bad at evaluating risk. And, in particular, there was a kind of throwaway line in the book: These two Israeli psychologists had pointed out that people aren’t really good at understanding catastrophic risks. That if you take something that’s a one-in-a-million risk and make it a one-in-ten-thousand risk, people don’t really feel the difference.

I was aware that Trump—who I think of as a weirdly risk-loving person—was largely ignorant of the federal government, and was being handed the federal government. And the government was this portfolio of, among other things, catastrophic risk. I guess at some point, I connected the sinking feeling in the pit of my stomach with that and I thought, This is kind of interesting. You have this guy who is really a machine for amplifying all sorts of risks being handed this portfolio of risks.

So I started poking around, and it was this very odd situation. A combination of Obama’s sense of responsibility and new federal law required an outgoing president to prepare for a transition—prepare essentially a course in how various parts of the federal government worked for the incoming administration—[and] led to this really wonderful course in how government work was being created. And the Trump administration just had not shown up to take the course. They basically didn’t show up for the transition. So then I had an idea, and the idea was: I’ll go take the course. I’ll go figure out what the hell the federal government does that the Trump administration doesn’t know it does, and that’s what led to the book. It led first to a couple of pieces in Vanity Fair, and then led to me wandering further inside the federal government.

The story is a bunch of things at once, but it’s me looking for hidden risks. Risks that people may not appreciate are being managed by the Trump administration, or mismanaged, and it’s also giving myself a little bit of a civics lesson of what the hell does the Department of Commerce actually do. And when you get into these places, I mean, it sounds strange to say— they’re riveting. There’s no part of the federal government that doesn’t have some serious purpose. And in most cases, when you ask the average American citizen what it does, they have no idea. So I felt there was a kind of literary opportunity created by Donald Trump potentially mismanaging this whole enterprise, and that threat just electrified the material.

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In terms of timeline, we’re not even two years removed from the inauguration itself. You've turned this book around pretty quickly. I know The Undoing Project took years of legwork to put together. How does your approach to research change from book to book?

There are a couple of big differences between these last two books. One was that this one is shorter. It’s half the length of The Undoing Project. And second, it’s reportage. It’s me really wandering around trying to see what’s going on. So there was very little required in the way of historical research, whereas with The Undoing Project, I had to dig into the history of Israel and the history of these two guys, one of whom is dead, and the material was a long way away. In addition, The Undoing Project—one of the reasons it took so long is it took me a long time to believe that I was actually qualified to write it. I just thought, There’s got to be someone else who is better suited to be doing this.

In the case of The Fifth Risk, I didn’t really have that thought, just because I felt like I’m as qualified as any citizen of the United States to go to try to understand my government. I was coming at it from the point of view of an innocent, whereas with The Undoing Project, I didn't have that luxury. I had to get up to speed at kind of a graduate level on a field, cognitive psychology, that I knew nothing about. So although the federal government is sprawling and incomprehensible and impossible to get your arms entirely around, once you’ve performed the trick of deciding where inside you want to go and why, and limiting it that way, it wasn’t nearly as hard to do.

What was hard about it was getting people that were inside the government to want to talk on the record. [They were afraid] they were going to lose their jobs. I left stuff undone that I could have done. There were two or three other places that I would have kind of liked to have gone, but I was just trying to give the reader a general idea. I don’t have to be comprehensive here. So the selection was the difficult part. Once I decide I’m going to write about the Department of Agriculture, it's not that hard. You start calling people and you pull on one thread in a hairball and the whole hairball comes unraveled. Once you’re inside the place, you quickly get to what the story feels like it should be. Having said that, if I was a more diligent person, I would have turned it around even faster. It was probably an honest nine months work, or a year’s work, and it’s taken me two.

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In your books, of the sources you talk to, you typically find some that serve as central characters. They appear prominently, pushing forward the through-line. When reporting, how do you know when you’ve found a person who could be that central character?

You are absolutely right, I hook up with people and I let them tell my story. I'm in the market for teachers. And when you were in school, you can remember when you would walk into the classroom and you were just entranced by the person at the podium talking to you about whatever subject it was, and you can remember when it was just dreary. And there are people who are gifted teachers and there are people who are just not very good at it. And so you kind of know when you meet a gifted teacher, and that’s exactly what I'm in the market for. It’s what I was in the market for this story as much as any. When I wandered into Energy or Agriculture or Commerce, the White House, I was looking for someone who really could just explain things to me and explain them in an interesting way.

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Finding that person … it’s not a science, but the way I find the people is I talk to 50 people to find one. So if you walk into the American stock market to write a book about the American stock market, there are a lot of people who say, “You have got to go talk to Brad Katsuyama over IEX. He’s got a story and a way of looking at this that’s just really interesting.” [Editor’s Note: Katsuyama is a central character in Lewis’ 2014 book, Flash Boys, about high frequency trading.] So people lead you to the main character.

One of the themes linking your books is the question of how we, as humans, assess value: the value of people, places, commodities. Does The Fifth Risk continue that trend? What makes value assessment such fertile ground for exploration?

The answer is yes. I was intrigued, in particular, by the disconnect between the value of federal employees and what they’re paid, and what people think of them. They’re people doing things that are mission critical to society who are paid modest sums of money, and who are routinely kind of shat upon. That really interests me. In some ways, they are the mirror image of a Wall Street guy who makes millions of dollars a year who doesn’t actually make any contributions to society at all. But the other thing that really captured my imagination in the very beginning was the way people valued the risks. The way society is misjudging the risks it’s running, and is doing it because—I think—we’ve essentially lived through a historically unprecedented period of decades of relative peace and prosperity. We’ve forgotten what real trouble looks like. So we’re courting real trouble in ways that we never would if we had a living memory of it. So it’s a misevaluation of the risks. That interested me a lot.

I think one of the threads through some of my books, anyway, is markets. How markets function or don’t function. And much of what I’m writing about that the government does is stuff that the market wouldn’t do. The reason the government is doing it is because the market doesn’t. That doesn’t mean it’s not important. Collecting all the data that we need to predict the weather is really important, but the market wouldn’t do it by itself. The story certainly reflects my interest in where markets kind of fail, because that’s where government steps in.

For The Undoing Project, you met psychologist Daniel Kahneman (a main character in the book) in 2007, which is right around when you were working on The Big Short. When you’re sorting through your bucket of ideas, how do you know what idea you want to pursue next?

You’ve asked me at a good time, because I finished this book last week and I’m already thinking about what I want to go to. When I’m working on something like The Fifth Risk, I will see things that will interest me [and] will make little manila folders with the idea on them. And I’ll toss them into a pile next to my desk and I’ll forget about them. So I’m now on the road. I’m going home tomorrow, but on Monday I will literally take this giant pile of manila folders with ideas and go through them and say, “Are any of these where I want to go next?” And if I feel a flicker of interest and passion about it, I’ll start out on one.

I’ll call my magazine editor and I’ll say, “What do you think about me trying to do 10,000 words on this subject?” And if he thinks it’s great, I’ll start in on that. And if it ends up being really fertile, it becomes a book. If it doesn’t, it might not even become a magazine article. There’s a lot of trial and error. But it’s funny because if you ask me what I want to write next, generally, I would say I want to write a sports book. I want a break from financial crises and government, and I would like to go have some fun with sports. But if I don’t have a subject that’s compelling, then I won’t write a sports book. So I have these theories about what I would like to write about, and sometimes it just doesn’t pan out.

It’s a bit like romance, right? When you’re single, all of a sudden weird things walk into your life that otherwise wouldn’t walk in your life. I’m now single and open to romance with ideas, and now moving through the world, kind of making eyes at them at the bar. And whatever happens happens.

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In structuring your books, characters will often be introduced in somewhat unexpected ways. It shows a lot of patience in laying out your narrative. How do you plot that out when trying to get from A to Z?

It’s the hardest question. I don’t find myself able to start until I know where I’m going to end. Another way of saying it is: I can’t start until I know the structure of the thing. And I play forever with that. Some stories have very simple structures, and some have very complicated [ones].

The Big Short was one that was very complicated because I had not one main character, but basically three. Threading them together, it took me forever to figure out who goes where. But I also find when you recognize there is a structural problem or a structural challenge, that it often reveals stuff about the material. Like The Big Short, in realizing that I was looking for ways you might have gotten to the right answer when Wall Street came to the wrong answer about what was going on in the markets—and there were these three different ways to get the right answer [embodied by my three characters]—it focused my mind much more sharply on the particular way the people who were the heroes of The Big Short had gotten to the right answer.

I agonize over structure. I’m never completely sure I got it right. Whether you sell the reader on turning the page is often driven by the structure. Every time I finish [a book], I have this feeling that, “Oh, I’ve done this before, so it’s going to be easier next time.” And every time, it’s not easier. Each time is like the first time in some odd way, because it is so different.

A lot of your work in Vanity Fair tends to foretell your books. You did a piece on Daniel Kahneman before The Undoing Project came out, for instance. What are the biggest differences between a magazine piece and a novel? How do you know when an article could be blown up to novel length?

Sometimes, I go to write a magazine piece and realize while I’m writing it that there’s a book here. This isn’t a 10,000-word thing—this is a 50,000- to 100,000-word thing. So that starts the process. For me, the magazine world is R&D: That’s the research and development. I’ve never had a subject where I thought, Oh, by the way, this is a book, and I know it before I’ve written a word of it. Always, it started as some minor thing.

So Moneyball, for example—in the end I did not run a magazine piece in advance of it, except the excerpt to the book—but it started with me talking to The New York Times Magazine editors about writing a piece asking whether there was now class warfare inside of a baseball clubhouse, because some people get paid $8 million and some are getting paid $200,000. I wondered if the left fielder was pissed off when the highly paid right fielder dropped a fly ball. And that got me into baseball. That magazine piece that never happened got me to Moneyball as a subject. So the magazine stuff is my way of getting out of bed in the morning and getting to work—that’s the role it plays. And if it becomes a book, it becomes a book just because I think it’s got that level of interest, it’s worth writing at that length.

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You recently signed a deal with Audible to do some of your magazine work in an audiobook-style format. Talk about what drew your interest there, and how that approach is unique.

Not only some: I am going to all of my magazine work for Audible, because it’s not that much. I’ll tend to do one or two big pieces of magazine work a year, and I’m just going to do them [with Audible] now. The reason I’m going to do it that way is, first, I find when I read—when I have to read something aloud to an audience or to myself in a recording—I see all kinds of stuff that I don’t see if I don’t read it. I mean, I see mistakes, I see infelicities, I see unnecessarily complicated sentence structure and words. I see devices that creep into a piece of writing that I think are more likely to be repaired if you have to perform the piece.

Second, the pressure up front of knowing you are going to have to entertain an audience that’s listening rather than an audience that’s reading, I think it’s kind of a higher bar to jump over. That’s going to raise the standards of what I write about. I’m already finding that when I’m thinking about subjects, I’m requiring more of the subject thinking about it as an audio-magazine piece than I would have if I was thinking of it as a written-magazine piece. I kind of like that. The short answer is: I think it’s going to make me better. And my editor for Vanity Fair, who I adore, moved to Audible, and I wanted to continue to work with him.

What drew you to nonfiction, as opposed to fiction or poetry or any other kind of form?

There’s a kind of writer who’s the stereotypical writer, who knew he was going to be a writer from the age of 6. And everybody said, “Oh, he’s got a way with words,” or “Oh, he’s bookish,” or “All he does is sit in his room and read,” or “He writes great poetry.” And that person is naturally channeled into literally thinking they are writing fiction and writing stories. And I was never that kid. I was a jock. I loved to read, but I did not define myself by my relationship to the printed word until I got out of college. So I was already starting in an odd place. I hadn't studied creative writing. I never thought of myself as a writer, I just started to see things that were interesting to write about. It was an engagement with the world, coupled with a love of putting words on the page, that got me going in first place. So nonfiction was a natural place to start.

Having said that, I do think that the distinctions that we make in this country between fiction and nonfiction are a little overblown, in that most good novelists are drawing on direct experience of the world and often go off and research things in a way that a nonfiction writer does. And nonfiction writing requires, if you do it really well in a narrative way, some of the tricks of a fiction writer. The lines get much more blurry in other countries. We have a sharp divide between them. I never felt like there were a lot of things that I have to say that I can only say in a fictional form. I feel like what I have to say I can get across in nonfiction.

What advice would you impart to writers looking to break into book-length nonfiction?

I would start small. I wouldn’t just start by trying to write a book. I’d start by publishing pieces online or in magazines or newspapers—wherever you can get them printed. There are two kinds of general pieces of advice I would give young writers. One is: Make sure what you want is not to be a writer, that what you want to do is write. You see this a lot in colleges and creative writing programs—all these people who love the idea of being a writer who actually don’t particularly want to write. And so they moan and groan and kind of preen as writers, but they don’t actually write. If you want to be a writer, write. Think of yourself as a tradesman; don’t think of yourself as an artist. If the artistry comes, great. But it’s going to follow on the heels of lots of training in your craft.

The second thing I would say is it’s very hard to write without having things to write about. You can write about your navel, you can write about your dreams you had last night and other things that nobody is going to have any interest in but your mother. On the other hand, you can get out in the world and find things that are interesting to write about. That doesn’t mean necessarily going out as “a writer.” You could go work on a Chinese fishing boat, but having experiences that interest you in the world are a good first step to having material.

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