This piece is different than the usual. I’ve received enough inquiry about my writing (and creative) process to justify a short newsletter. Learning how to write and finding my own voice has been one of the best investments I’ve ever made. Here are three things that I’ve learned along the way.

My Approach: Leaving the Shire

Writing is an intensely personal activity. Sure, I think there are some fundamentals: you have to write a lot (a million words, at least) before you really start finding out who you are and what you have to say. No substitute for that. And there is indeed a craft—some things are objectively bad, like poorly-pounded-in nails on a new house. But as far as ‘routines’ and style go, I find that most advice is stifling rather than liberating. I’m not here to do that.

What I do hope to convey is a sense of the spirit with which I like to approach my work—the pre-conditions that make writing something worthwhile possible for me in the first place.

The places and people around me matter intensely. That’s because my approach to writing involves spending a lot of time outside of the home, preferably in new or unknown environments that stimulate my mind and my spirit.

Traveling internationally with me can be maddening because my favorite thing to do is flâneur—to get lost down back alleys and find a table somewhere to write when the inspiration strikes. I never leave home without my writing instruments because I never know when I might find the right place and time. (“Tickets? Screw ‘em! What’s the refund policy? [insert Rick Steves rant from me].)

For the three years that I lived in Europe, my favorite place to do this was in piazzas or tucked-away coffee shops or pubs.

Before the pandemic, at least, I was always out and about writing in unlikely places. Now I’m now back to doing it, albeit a bit less frequently.

In the States, I’m the solitary figure sitting alone in a restaurant between lunch and dinner service, alternatively staring out of a window and typing away measuredly on an iPad, or drawing diagrams on the backs of napkins.

There’s something about being immersed in everyday life while I’m writing that brings ideas and words down to earth. I also find it a never-ending source of inspiration and observations.

My writing process is non-linear. A high-level story (or essay) arc forms in my mind (passive voice intentional here—because creativity is not something that happens from me but something that happens through me), and that high-level arc is usually all I have to work with. I just start writing. I don’t worry about the details. I let each sentence lead me into the next.

I’ve learned never to spend too much time on outlines because I write in such an iterative way that my outlines never amount to much, kind of like business plans. Once I take action on something, whether it’s a business or a book, everything changes. Emergent possibilities open up. My body changes. My thinking changes. I believe this is true for everyone. To quote Heraclitus: “No man steps in the same river twice.” Time continues to flow, and so do we. We’re not who we were yesterday.

I teach an introduction to business course to (mostly) college freshman. When my students come to talk to me about business ideas for startups, my common response to whether I think their pitch is good is: “I have no idea.” I ask them to take some concrete action to move the ball forward, then come back to me when they’re done to continue the conversation. At that point, I’ll then give them 1–2 more actions to take. Each time we chat, we’ve learned so much that it’s like the first conversation happened in a different universe, a different space and time. Because it did.

Action changes everything. This has been as true for me as an author as it has been as an entrepreneur. The book proposal I submitted to my publisher and the book I actually wrote are two entirely different things. The finished book barely resembles the chapter outline I submitted because I realized in the process of writing the book that there was a much better path to take.

(I suppose I wouldn’t have known that, or even gotten there in the first place, had I not at least tried to make out a pathway on paper. That may be the best case to make for writing a proposal: to make sure you and an editor are on the same page, at least, or to force yourself to try to articulate what’s in your head to find out if you can even begin to get another human being interested in it. Once you do that, the journey takes as many twists and turns as Frodo and Sam’s. The outline/proposal/pitch may be a necessary beginning, but it’s only that: a beginning.)

Alright, back to this strange “writing in public places” quirk of mine. It’s curious. I’m a relatively introverted person on the whole, but I still feed off the energy of other people for creativity. Maybe that’s because I’m not necessarily talking to or interacting with them—just absorbing things. Maybe that’s why, as DFW noted, every real writer is at heart a bit of a creep. (How else to observe reality while maintaining a kind of spiritual distance to it…other than to observe reality without fully engaging in the reality of others, which would kill the ability to write about it in the moment?)

A caveat: the public space is better for certain kinds of writing—not necessary all of it. It works best when I’m either staring at a blank page or when I have nothing to do but ruthless edits. All of the in-between stuff does often happen in a more traditional setting (I do indeed have a home office). But I don’t know what I’d do if I had to do all of my writing between those four walls, without getting out into the wild.

I think writing in these places affects my style. At my best I like to make you, my reader, feel like I’m your buddy, bellied up next to a bar talking about life. I don’t want to talk “at” anyone. I want to write as a fellow traveler who is exploring how the world works, with you as my fellow interlocutor. I hope some of that casualness and friendliness of a man having a cold beer after work comes through once in a while. If so, it’s because I may have been literally doing that when I wrote the words.

If I had to name three things that really characterize my writing process at this point in my life, they would be:

1. Speak the truth no matter what the cost. If you write worried about what every critic thinks, you’ll write the lowest-common-denominator work possible. And nobody wants to read that except for those suffering from Twitter-Brain, in which “content” passes for thinking.

2. Limit your sources (and your mimetic “Source Anxiety”). At some point, you have to put down other books and sources—all aids, all crutches—and walk. Often, the more you try to absorb and “incorporate” everything into your writing, the more convoluted it sounds. Just write. Don’t try to do too much. I came to a point in my research when I realized that there would always be more rabbit holes for me to go down—more reasons to gather and hoard more information—but I moved forward and wrote on my own terms. Trust yourself. Trust yourself to say something new, in your own voice. You have to let go and step away from the boat.

3. Exercise restraint. Writers—especially new writers—try to do too much. We want to flex every muscle in our brains in every sentence, every chapter. That’s a huge mistake. There is an order—a natural unfolding—to everything. Learn it. Try to put yourself in the place of your reader. My agent, Jim, once told me that there are three different drafts of every book: 1) the one you write just to figure out what in the hell you’re trying to say; 2) the one you write for your editor; 3) the one you write for your reader. The last one is the most important. Books that aren’t written for readers are called the worst term imaginable: “self-indulgent.” Indulge yourself with your favorite foods on Sunday; not with your own words.

Alright. These are a few of the things that have helped me along the way. I share them here because we’re all writers at heart. We all want to communicate something to others.

You’ll develop your own tactics as long as you’re paying attention to what works and what doesn’t—and to what brings out the best in you. Attend to reality. Attend to yourself. Attend to your reader.

Your tactics will be different from mine. After all, in all these years, I’m yet to see a fellow agonized writer hacking away on his laptop next to me in the corner of a restaurant between lunch and dinner service. But I’m always on the lookout. Maybe I’ll see you there. Or here.