NAME: Annie Duke
CLAIM TO FAME: A former professional poker player and World Series of Poker champion, Annie is a public speaker and expert in the science of smart decision making. She is also the author of five books, including her most recent, Thinking in Bets.
WHERE TO FIND HER: On Twitter, Amazon, and on her website.

Let’s start with the basics: What time of day do you start writing?

As a pretty busy mom, it is hard to have a set time of day for writing. The time of day I start writing is when I’m free which is, generally, mid-morning. I am very protective of dinner time and weekend time with my family, so that leaves weekdays when the kids are at school for most of my writing.

Do you listen to music when you write, or do you prefer silence, or something else in the background?

I am really bad at processing more than one channel at the same time. For example, I have difficulty having a conversation in a car with someone if I have the music going. So for writing, I need total silence…no music, no television, no conversation in the background.

Do you write every day? Or do you write in spurts or only when there is a specific project? Do you have a sense of how much of what you produce ever sees the light of day?

I don’t write every day, but I do read every day which I think counts as preparation for writing. When I’m working on a particular large-scale project (like a book), I attempt to write every day, though that generally doesn’t include weekends. When I don’t have a large-scale project, I’m writing as needed for upcoming talks or my newsletter, as examples.

Even when I am working on a big project where I have committed to writing every weekday, I recognize that sometimes I need a few days off. I find this prevents writer’s block. When I see that I am struggling to sit down and get the words on paper, writing will start to feel like a chore and I will feel resentful for being made to do the chore. By taking that little bit of space, I can come back to it fresh and enthusiastic and much more open to the process.

I would say about thirty percent of what I actually put on paper sees the light of day. The reason that percentage is so high is because I do a lot of drafting in my head and I workshop the material with other people before I ever put pen to paper. (Fingertips to computer?) By the time I sit down to write, I’ve already put in time on what I want to say: something I’ve written or spoken about in the past, new applications or directions, things I’ve read, discussions I’ve had with people close to me testing out the material and getting input.

Do you have any pre-writing rituals or habits?

No rituals but definitely habits—pre-committing to when I want to write the next day, setting goals for how much I want to get written, setting my own deadlines with my editor, etc.

One of the most successful habits I have developed is setting my own deadlines for turning in work with my editor rather than allowing my editor to set them. By telling my editor when I will turn in the draft of each chapter, I own the deadline. I create the terms of the contract, which makes the contract much harder for me to break. When someone else sets the deadline, it’s easier to rationalize breaking the contract: it’s an unreasonable deadline, or they don’t need this much time with the material, or I’ll save them time by taking longer. It’s a lot harder for me to rationalize those things when I am the one who set the deadline.

What was the best money you ever spent as an author? What did you do with your first book advance?

I’ll answer the specific question of what I bought with my advance. This is a type of question I got a lot in poker: What did you do with your money from a particular tournament win? My answer, which is the same as it was then, is “nothing in particular.” I’m not buying anything beyond what I would normally be buying. I don’t think of a book advance—or a big poker win—as a windfall. I treat it as the paycheck I’m working for, just one that comes in a lump sum instead of regular intervals. So how I spend money from a book advance is the same as how I would spend a regular paycheck. At least that is the goal.

I recognize that’s a boring answer, but it’s the same answer I gave when I was playing poker and was asked how I had spent a big tournament win (and I felt then that people were often disappointed by that answer).

Is there a time you feel like you are most productive as a writer? Mornings? Late at night?

I have a big dip in the clarity of my thinking late in the afternoon and early in the evening so I try to avoid writing at that time.

One of the things that’s really important to me is that I try to invade family time only as necessary. So once my kids are home from school and my partner is home from work, I try to protect my time with them as much as possible. Only when I absolutely have to, because of an impending deadline that I am in danger of not meeting otherwise, will I work late at night, after everyone is in bed.

My peak period, roughly mid-morning to mid-afternoon, when I tend to be most alert, is also right after I’ve worked out and I find that I’m really at my mental best after I’ve worked out. What that means is that my most productive writing time and the time I most value spending with my family don’t overlap much, which is fortunate.

Finding a great idea for a book can be one of the most challenging aspects of an author’s life. How do you find book ideas? How did you come to the idea for Thinking In Bets?

I started speaking to business and professional groups about decision strategy in 2002. Since 2012, after I retired from professional poker, that’s been my main work. Those speeches were the starting point for the ideas in Thinking in Bets. The conceptual themes of different speeches overlap, but I want my approach to always be fresh. I’d get bored giving the exact same speech I was giving in 2002—or even repeating the exact speech I gave a month ago. So I am always trying out different ways into the material, new narratives to bolster the concepts, fresh ways to organize the material.

Doing this in front of an audience, piecemeal, as I’m giving different speeches, makes generating new ideas much less daunting than having to develop an entire book’s worth of material in one fell swoop. Trying out new ideas and approaches to material through the speaking process acts like a workshop for those ideas.

In terms of Thinking in Bets, I certainly had developed a lot of these ideas over the course of many years through my speaking. That being said, there are a lot of windows into a book on uncertainty, bias, and how to be a better decision maker. Finding the best window into the topic was a process that required a tribe. I had a tribe for Thinking in Bets.

First, the audiences I’ve spoken to acted as part of the tribe. Seeing how those audiences responded to differing approaches into the material helped me immensely in the development process. Second, my literary agent, Jim Levine, was a key part of the tribe. The process of writing the proposal forced me figure out how to translate material that I had mainly delivered in a spoken word format into the more linear format of the written word, which changed the framing in significant ways. Jim’s input sharpened and refocused the material, taking the proposal in new and unexpected directions before we went to publishers. Third, Niki Papadopoulos, my editor at Portfolio, was tremendously helpful in guiding me toward “the betting window.” In the book proposal, thinking about decisions as bets was a prominent theme but she made me see that as the headline. And, of course, all the amazing thinkers with whom I’ve had the privilege of interacting were invaluable in helping to develop the ideas.

Just as feeling out how audiences respond is important to developing the material, being really open minded to how the really smart people around me saw the material was helpful in terms of figuring out the window through which I should be looking at these issues.

As one of the more successful poker players in history, you have insights into strategy and decision making not many will ever have. How do you apply strategy to your writing routine? Where do most aspiring authors fail when it comes to this area?

The main thing I think that I take from poker into writing is this idea of defining “the goal of the game” at each part of the process, and being motivated by wanting to win at that particular game. For example, I think that for most writers it’s incredibly painful to do a big edit of their work. You turn in a first draft and your editor invariably says it’s too long (at least mine always does!). As authors, most of us have a surplus of ideas and are encouraged—and rightly so—to develop our ideas and not be afraid to go where they lead. We’re all capable of getting excited about our ideas, falling in love with our ideas, and doing almost anything to avoid killing off words that we have so diligently put to paper. The editing process can be painful. It’s painful to let go of work that we’ve written and crafted and love.

Editing for me was not a particularly painful process because I shifted from “the writing a manuscript game” to “the editing game.” That allowed me to be less endowed to my own words (something important in the manuscript game) and do my best to win at the editing game. To win that game, I had to slash things I previously crafted as “persuasive” because they were also “repetitive.” I had to recognize where “thorough” was “going down rabbit holes.” I had to find where “detailed” was “too technical.” To win the editing game, I had to be good at cutting, refining, condensing, and letting go. So those were the goals that I set for myself and I got pleasure out of doing that well.

I am just as susceptible as any other author to admiring and wanting to preserve the full expression of what I labored over and submitted. But one of the great moments in the writing process was when Niki reviewed my edited draft (after she told me the manuscript was much too long) and said, “Wow, you cut out 10,000 words. That’s hard for a lot of writers.” For me, it was, “Yes! I won the editing game!”

I apply that throughout writing: the organization game, the deadline game. Figure out what it takes to win that game, and don’t get stuck playing part of the game that’s over or where the rules have changed.

When you think about your writing life, you’ve cut across genres. You’ve written an autobiography, poker strategy books, and now a general strategy book. Do you have different routines or habits for different formats? How does your approach change genre to genre?

For my autobiography, I had an assigned coauthor. As a result, I didn’t feel as invested in that book. My process was just sitting down, telling someone the story of my life and they helped me write it.

The poker strategy books and Thinking in Bets had a much different process then my autobiography did, but a similar process to each other. I had been teaching poker seminars for several years. The three poker books came out of those seminars, in which I developed a framework to communicate my approach to the game to my students. Those seminars then evolved into book form.

Thinking in Bets developed out of many years of thinking, speaking, and consulting, figuring out how to communicate these concepts to audiences in a way that held their attention. In this way, the approach was very similar to the poker books I have written. Where the approach diverged was in seeking out experts in decision making for Thinking in Bets. In the poker books, I was communicating my way of thinking about the game. Thinking in Bets is much more a combination of my way of thinking about decision making developed through my academic life and my time at the poker table, and the decades of work done by researchers on the subject.

How has spoken word storytelling improved your writing? What’s the main thing you’ve been able to take from your experiences with The Moth and elsewhere and apply to writing?

The Moth was a very scary thing for me to do. I’ve done a lot of speaking, but it’s generally been driven by ideas and strategies. That’s different than having to hold an audience with a narrative about your own life. The Moth has wonderful directors who helped me understand how to craft a good narrative. I hope that experience in spoken-word storytelling shows through in Thinking in Bets. The material is idea-driven material, but there are a lot of narratives supporting the more explanatory sections of the book. That came out of understanding the power of spoken-word storytelling.