Age when he started: “I don’t remember a time when I didn’t want to be a writer.”

Our favorite of his work: The Resilient City

Let’s start with the basics: What time of day do you start writing? Is it easier for you to write early in the morning? Late at night?

I definitely believe in writing rhythms.  Especially in New York City, I write best in the early morning or late night and I find the energy is too distracting to write during the daytime unless there is major breaking news on deadline. But when the city is asleep, you can focus for sustained periods of time.  Otherwise, the adrenaline of New York is just too intense.

What’s your preferred tool for writing—a word processor like Microsoft Word, Google Docs, etc.? A pen and paper?

Microsoft Word on a Mac laptop.  I’ll occasionally scratch notes or outlines on a piece of paper or cardboard next to my keyboard.  My only real peculiarity in terms of the mechanics of writing is that I write and think better at a standing desk as opposed to sitting down.  I’ve got one at home, which I bought with the advance of my first book, and a smaller version in the office.

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

I’ve got a theory that most writers are either frustrated musicians or painters – and which of them you are depends on whether you write for the ear or the eye.  As a former musician and former speechwriter, I definitely write for the ear. I listen to music all the time for inspiration and energy. I tend to make playlists as the sound track for writing different books.  They serve as snapshots in time.  So, I’ve got one for Wingnuts – lots of The National, Drive-By-Truckers, Radiohead and Randy Newman – and one for Washington’s Farewell that’s more classical, jazz, the Americana series by Chris Thile, Yo-Yo Ma and Edgar Meyer and the soundtrack to Hamilton.

I’ve belatedly realized that when music has lyrics it’s subconsciously distracting while writing.  Some of core writing tunes: Miles Davis’ In a Silent Way; Sigur Ros and Philip Glass’ “Heroes” Symphony. Guilty pleasures are soundtracks to Inception, Pollack, Glory, Milk, Cinderella Man and The Social Network. Hans Zimmer’s Time from the Inception soundtrack is probably the song I’ve written most to over the past few years. But I’m always looking for new music to write to – it’s a great and weird sub-genre. And as you can probably tell, I love talking about music.

Do you have any pre-writing rituals or habits?

Not really. Coffee and seltzer water – music playing and the relevant research piled up beside me.  If it’s late, maybe a bit of bourbon.

How many words a day do you produce, or try to produce? How much of that ever sees the light of day?

Even when I’m writing a book, work that I’m sandwiching into otherwise crowded days, I don’t have a set number of words I aim for.  I basically write as much as I can until the need for sleep starts clobbering my synapses.  If the words are coming slowly, I’ll try dictating first drafts, but I’m still not entirely convinced that this nets out in terms of time saved.

When you first sit down to write, how do you start? What goes through your mind when fingers are first meeting keys (or pen hits paper)?

I’ll pick up where I left off or perhaps read the last few paragraphs, mentally situate myself and try to pick up on the thread of the idea, or perhaps music behind the idea.

What’s your process for editing your work?

I’m an obsessive editor and, to my great discredit, I still can’t resist editing while I write, which clearly cuts back upon my ability to achieve maximum output.  It’s a terrible habit to constantly tweak, aiming for precision. After I’ve written a significant amount, I’ll edit that section with paper and pen, rearrange, etc. On some level, I’m taking dictation for the unwritten script that’s in my head, and I know when something sounds right or sounds wrong.  When it’s time for something resembling a final draft, I’ll read it aloud to Margaret and find all sorts of new mistakes and room for improvement.

Do you have an author whose voice or style you’re trying to emulate when you’re writing?

I’d like to think I’ve outgrown that. Ultimately, you’ve got to be un-self-consciously yourself and grow into your voice to the point where you’re not looking over your shoulder and comparing yourself to other writers. But I’ve definitely used writers to kick start my inspiration, and I can hear their voice in different paragraphs, particularly some of my earlier books.  I love reading Jimmy Breslin, Murray Kempton, Jim Harrison, David Remnick and historians like David McCullough.

But the writer who I use the most for this purpose is almost certainly Martin Amis – but his journalism and non-fiction rather than his novels.  I’ve read the pieces from The Moronic Inferno and Other Visits to America dozens of times, particularly when I was writing Wingnuts in an insane three-month sprint right before I got married. One of the most surreal, terrifying and gratifying events of my life was sitting next to Amis flying out to cover a presidential debate in Wisconsin, and he was reading Wingnuts next to me. It was like having the professor you most admire grade your work silently in front of you.

Do you struggle at all with that dreaded enemy of writing: writer’s block? Do you think such a thing exists?

I’m superstitious about writer’s block to the extent I don’t particularly feel like devoting a great deal of time to dwelling on it.  It seems like getting stuck in a desert, a nightmare. But there are definitely times when the inspiration flows more freely than not. It seems to me that writing is a muscle: it gets stronger the more you use it.  If you let yourself fall out of the habit, it can be hard to get back in form. Writing a regular column keeps you limber and sharp and guarantees that any fear of writer’s block is kept at bay.

Do you have any favorite books about writing and the creative process?

The Writer’s Chapbook edited by George Plimpton has excellent little snippets of advice. I’m not a horror fan, but Stephen King’s On Writing is full of durable wisdom. I love the shop talk of writing.  I’ve got a coffee table book of photographs by Kurt Vonnegut’s wife, Jill Krementz, which shows the desks and writing rooms of great American authors, which I find strangely comforting, although most of them have been put through a museum standard of cleanliness, which seems utterly unrealistic and therefore, un-relatable.  Ultimately, the best advice about writing is pretty simple and self-evident: write the book you want to read.

When did your aspirations to become a writer begin?

I don’t remember a time when I didn’t want to be a writer. There were certainly times as a kid when I was more fixated on becoming a baseball player, an NYPD detective or even president, but books were how I immersed myself in those worlds. So when I got excited about other topics, it was always through the medium of books and writing.  There is a terrible power in its ability to memorialize the moment that’s best approached with kindness.

You were a speechwriter for Mayor Giuliani on 9/11. Tell us what writing during that fraught period was like.

It was a defining time of my life and I felt grateful that I had something constructive to do with my emotions that could perhaps help other people. I’m proud of the work we did, particularly writing hundreds of eulogies for the fallen firefighters and police officers with our small team of speech writers which included Owen Brennan and Matt Lockwood. Ultimately it was an extreme example of the opportunity writing provides, which is to help make the moment mean something transcendent. When you watch thousands of people be murdered, it’s about trying to salvage some meaning and deeper purpose amid the shock and loss.

I remember going down to City Hall the next day and walking down to St. Paul’s Chapel across the street from Ground Zero and walking on the perimeter pf the building to see if any windows were broken. They weren’t. That became a central metaphor we used for the resilience of New York City at the prayer service at Yankee Stadium. An essay I wrote about my experience as the mayor’s chief speechwriter after 9/11—which I was going to call The Eulogist because unfortunately, I’ve probably written more eulogies than anyone else—was selected to conclude the anthology of writing about New York called Empire City.  It’s called The Resilient City, and it captures what that time was like directly. I think it holds up.

You’ve written for print newspapers; you’ve written online. Do you find yourself writing differently for medium as opposed to the other?

I don’t write for different mediums differently, although obviously I love the reported column, which is why I put together the Deadline Artist anthologies with my friends, Jessie Angelo and Errol Louis. We consulted Jimmy Breslin and Jack Newfield, who was working in the New York Sun newsroom at the time. The books still provide enjoyment and inspiration. At one point when I was writing for the Daily Beast, CNN and the Sunday Telegraph of London, I was able to make the columns sufficiently different because I was writing for decidedly different audiences. I did reported columns for The Daily Beast, while CNN was a more 50,000-foot view of a trending topic that got me fired up in the realm of politics. For the Telegraph, it was really explaining that week in American politics to a British audience.  And once you figure out the different altitudes of the audiences that go with different sides, it’s easy to adjust.

You’ve done both short-form columnist work and written books. How do you approach one of your books? What’s that process look like, given your day-to-day responsibilities? In other words, how do you get the book writing done, when the deadline isn’t nearly as pressing?

Writing a book with a more than full-time job and two small children is a thoroughly insane process, but as with all books, I was glad I did it once it was done.  You’ve got to find time to squirrel away early in the morning or late at night. Your vacations become based around writing, particularly if you have an understanding, tolerant and supportive bride, which I do. You cannot let it affect the responsibilities of your day job. It’s got to take a back seat, which is why you’ve got to work when other people are sleeping. But the work ends up being a break from the intense day-to-day pace of the news cycle. I looked forward to spending time with Washington and Hamilton and Madison. Everyone needs a hobby, and I suppose mine is writing books. There are certainly worse ones; at least you get a marker of your time on the shelf when you’re done, and hopefully create something that readers can love as much as you do.

How did you come up with the idea to write a book about Washington’s farewell address?

I kept bumping into Washington’s Farewell Address. My first book, Independent Nation, quotes Washington’s Farewell Address in the opening chapter. I closed Wingnuts with an extended quote from Washington’s Farewell and his warnings against hyper partisanship and polarization. Here was this famous but forgotten founding document, both timely and timeless. For all the times that people in American politics try to appropriate the Founding Fathers to excuse whatever ideological agenda that they have, here you have a clear warning from the first Founding Father about the forces he felt could derail our democratic republic; hyper partisanship, excessive debt and foreign wars. And as a former speech writer, I gravitated to the greatest team of ghost writers in history—first James Madison and then Alexander Hamilton—and the way you can see the interplay of their ideas throughout the various edits.

Ultimately, if you look at Independent Nation, Wingnuts and Washington’s Farewell, they are all different angles on the same idea. The common theme—the absolute vitality of the vital center—is a mainstream of American thought despite the current polarization and hyper partisanship. There is a deeper and older tradition that’s the foundation of American political wisdom.  It’s something that we’ve lost, but it needs to be found again.  And that’s the case I’ve been trying to make, approaching the same problem from different perspectives. Again, the core rule applies: Write the book you’d like to read.