Who: Chris Bailey

Claim To Fame: Chris Bailey has been intensively researching and experimenting with productivity since he was a young teenager, in an effort to discover how to become as productive as humanly possible. To date, he has written hundreds of articles on the subject, and has garnered coverage in media as diverse as The New York Times, The Wall Street Journal, GQ, The Huffington Post, New York Magazine, Harvard Business Review, TED, Fast Company, and Lifehacker. He is the bestselling author of two books about productivity: Hyperfocus, and the international bestseller The Productivity Project. Chris writes about productivity at Alifeofproductivity.com, and speaks to organizations around the globe on how they can become more productive, without hating the process.

Where To Find Daniel: His Website, Amazon, Twitter

Praise For Chris: “Here’s a book [The Productivity Project] that promises, in the title, to pay for itself. And, the truth is, it will, in just a few days. And you’ll even enjoy the journey.” — Seth Godin, Author of 18 best-selling books, including The Dip, Linchpin, and Purple Cow

When and where do you like to write? Are you the same-thing-every-day kind of guy or can you write anytime, anywhere?

For some reason, I can only work on books while at home or at a coffee shop (usually wearing noise-canceling headphones). I’d love to be able to write while I travel—I’m on the road about half of the time—but while away I typically focus on something else, like a talk I’m giving or an upcoming interview.

Do you have any pre-writing rituals or habits that you do before you sit down to write?

I do. I like to drink a coffee loaded with three or four shots of Bailey’s Irish Cream. (Kidding)

Here’s the pre-writing ritual I almost always follow:

[*] Enabling Freedom (my distractions-blocking application of choice);

[*] Making a cup of matcha, black coffee, or herbal tea (if it’s later in the day or I’m resetting my caffeine tolerance);

[*] Putting on noise-canceling headphones (particularly if I’m working outside of my home office).

Some other important conditions: my phone is almost always in another room, and I’m often disconnected from the internet. I find it essential to tame distractions ahead of time. That includes doing everything I can to reduce the temptation to check my email or tinker online instead of writing.

What do you do on days when the writing doesn’t come easy? Do you struggle at all with that dreaded enemy of writing: writer’s block? Do you think such a thing exists?

Writer’s block doesn’t exist in my opinion. If I’m struggling to string words together, it’s likely I haven’t thought through the idea in enough detail. Instead of trying to write in these moments, I step back and let my mind wander, or work on the outline of what I’m writing.

For this reason, I spend as much time on the outline of a book as I do writing the book itself. The writing part is easy and writer’s block-free once I have a framework for what I want to say.

Of course, like most writers, I do experience resistance to writing. The process of writing is rarely as satisfying as having written something. I experience less resistance these days, but I force myself to take more frequent breaks when this dreaded feeling does rear its ugly head. Resistance is a sign that my mind needs to recharge, and that I need to do some more thinking.

Do you find that you write differently or that your routine varies for short-form work versus your longer form books?

It does.

I typically have a few bullet-points I riff on while writing short-form things. It’s more extemporaneous and less structured.

Book writing is far more structured. My long-form writing starts by creating a detailed outline from my research notes. For my last book, I had around 25,000 words of notes, which made their way into the outline, and eventually the book. I also define a target word for each chapter based on how many words of research notes I had made for said chapter. That helps the information density of the book stay similar throughout, so that some parts of the book aren’t too dense or light on research.

In all your researching and writing on productivity, what have been the greatest insights you’ve applied to your writing routine?

This one’s easy: that I need to account for how lazy I am. We all need to account for our laziness when we write, or do anything else, for that matter.

Here’s one example of my own laziness: I’m not writing these words while sitting in front of the lovely adjustable bamboo desk in my home office. I’m mashing them out while lying on the couch eating leftovers. (My tiny vacuum bot is keeping me company, gently bumping into everything in the house.)

It’s all about accounting for this laziness in advance by completing that pre-writing ritual I mentioned earlier. I need to eliminate all distractions so I give myself no choice but to write.

Deciding on an idea to pursue writing about can be the most challenging aspect for a writer. How do you come to the point of ‘this is something I need to write about’ as opposed to ‘this is something I enjoy reading about’?

I love this question!

I typically let curiosity drive my work. If I’m curious enough about a topic, I try to do a deep dive to learn more. If I find there’s not enough good information out there, I sometimes decide to sink my teeth into the topic during a book or blog post. As a kid, I would buy magic tricks—not to perform them, but to figure out how they were done. I feel similarly about certain topics. I research them not only to hone my craft, but also to discover how and why something happens.

I also like being able to write on behalf of my readers. For my first book, I made myself the guinea pig for pretty much every productivity experiment under the sun, sharing with readers what actually worked. For my second book, I dug deep into the research surrounding how our attention works to figure out how we can get our stubborn brains to focus. Big projects need to both satisfy my curiosity and be something I can hunker down on in order to benefit my readers

What books or writers have most influenced the way you think and the way you write?

There are so many books. A few that come to mind: Getting Things Done, by David Allen; How Not to Die, by Michael Greger; and Mindfulness in Plain English, by Bhante Gunaratana.

Three authors inspire my writing every time I read them: Malcolm Gladwell, Seth Godin, and Stephen King. Their prose is contagious. I’m not sure of the extent to which they have influenced how I write, but I’d imagine that it’s a good amount.

What are the best pieces of writing advice that you’ve ever received or read?

You’re toast if you don’t have a deadline.

I hate letting people down, and I use this to my advantage. My editor at Viking/Penguin is one of the most intelligent people I’ve ever worked with, and the last thing I want to do is trip up his workflow by submitting a late chapter.

I also work with my team to set deadlines. After all, what’s worse than someone who writes about productivity missing a deadline?

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