.Well Traveled: Jeff Greenwald Revisits ‘The Size of the World’

Thirty years ago, Jeff Greenwald became unenchanted with airplanes. 

As an established travel writer who crisscrossed the globe on assignment for a variety of magazines, he had already logged more miles than Magellan, Marco Polo and Christopher Columbus combined. Yet, as he approached his 40th birthday, an idea intrigued him. What if he could circle the globe without ever leaving the Earth’s surface? 

Inspired by Tibetan Buddhist perspectives, the journey would be a kora, a circumnavigatory pilgrimage around a sacred site, in this case the planet. That is, Greenwald would start at his home in Oakland, then journey around the globe, and eventually return to his home in Oakland—all without boarding one single airplane.

The resulting book, The Size of the World: Once Around Without Leaving the Ground, was published in 1995 and documented Greenwald’s entire journey. A brand new 30th anniversary edition has just emerged, with Greenwald looking back on a lifetime of travel, especially the ever-changing ways that travel is documented. He appears in conversation at Book Passage Corte Madera on Saturday, Oct. 18.

Greenwald launched his journey in December of 1993, during the initial stages of the World Wide Web. The following month, in Oaxaca, Mexico, he posted the world’s first travel blog when he dragged an HP OmniBook into a Telmex office and uploaded a dispatch to the Global Network Navigator, an early website run by O’Reilly Media, the Sebastopol tech-book publisher. For the rest of the journey, he sent back various dispatches from the road.

Aside from capturing a harrowing journey around the planet, replete with jail time, cargo-ship stowaways, encounters with human slaves, a meeting with legendary writer Paul Bowles and all sorts of trouble, the book takes us back to an optimistic era, when the web was an untapped global frontier, a brand-new digital space invented to connect everybody, everywhere.

“There was this fascination—I remember writing about this in the book—this fascination with information and how weightless it is and the ability to carry so much information around on something like a small laptop,” Greenwald said. “And meeting hundreds of people in the world who had no idea what the internet was, had never heard of email, certainly didn’t have email addresses and could not imagine that in 20 years’ time, they’d all have this thing in their pocket called the smartphone that would transform their lives completely.”

Any true pilgrimage, in theory, must hurl the traveler into a series of hardships and temptations. In Greenwald’s case, they came in the form of unfriendly borders, religious fanaticism or vodka-swilling Turkish babes half his age. In New York, he finagled his way onto a cargo ship across the Atlantic. In Senegal, he overcame a nightmarish sequence of events in trying to escape Mauritania by crossing Western Sahara, an area still riddled with landmines. It was in Mauritania that he encountered people who still actually kept and sold human slaves. 

In a heartening chapter from Tangier, Greenwald busts in on the author Paul Bowles, then 83 and in poor health. After decades of irksome fanboys mischaracterizing him as a Beat Generation dude, Bowles actually gave Greenwald much more time than either expected. They hit it off and spent a few days talking shop about life, writing and travel.

Throughout the book, Greenwald weaves the 20 original web dispatches into the main narrative of his journey around the planet. On the actual day of his 40th birthday, he was marooned in the Sahara, uploading a blog before that word even existed.

“The OmniBook (laptop) weighed about four pounds,” Greenwald recalled. “It had a pop-out mouse that was absolutely adorable, and the most wonderful thing about it was that you didn’t always have to find a converter.” 

Even better, the laptop ran on AA batteries for nearly a week. That helped when stuck on a boring cargo ship for days on end.

“A lot of the parts of the book where I’m crossing, for instance, the Gulf of Oman for 12 days, or going across Saudi Arabia where there’s no way to plug in, it was absolutely a miracle to have this little laptop that was still able to record and write,” Greenwald said. “It had a black and white monochrome screen. It was smaller than any laptop I’ve owned since. That laptop is what made all those 20 dispatches possible.”

The OmniBook, however, nearly landed Greenwald in serious trouble. In Tangier, Greenwald was typing away in a bar when two secret police then approached him and wanted to know what he was writing. He wouldn’t tell them, so they dragged him away in an unmarked car and threw him in jail. They’d never seen a laptop, and they thought Greenwald was tinkering away on some sort of spy equipment. He had to phone back home to his editor in San Francisco, who then verified to the cops that Greenwald was on the up and up—a travel writer, not a spook.

After he circled the globe, in and out of hysterical or harrowing predicaments, Greenwald crafted the book with additional Tibetan Buddhist terminology. We get various chapters named according to various bardo states of transition: “Bardo of Fried Egg Sandwiches,” “Bardo of Rock ’n’ Roll” and even “The Bardo of Johnny Walker Red.”

“I chose to use the word more metaphorically to mean any difficult or unpredictable passage between one point and another, and to the entire trip,” Greenwald said. “I was very focused on the idea that this was a pilgrimage, and going around the world without leaving the ground was something I was doing to honor the earth, to sort of understand its true size and to challenge myself in an extremely difficult way for my 40th birthday as a travel journalist.”

Now a septuagenarian, Greenwald looks back on a book from 30 years ago with a tremendous sense of wonder, as any lifelong traveler would. He feels privileged to have captured a key moment in time, a world that was totally different and changing, and to have been part of the change himself, technology-wise.

These days, younger tech-savvy travelers often ask Greenwald for advice. He usually says the same thing.

“Wherever you go, wherever you find yourself, take at least a day or two to completely disconnect and, just yourself, be steered by whatever strange travel suggestions and encounters happened to you that day,” he said. “Don’t look at your phone. Don’t go online. Plant yourself firmly in the place that you are and focus outward rather than this sort of digital inward that we’ve all become somewhat accustomed to.”

Just don’t forget the OmniBook. 

Jeff Greenwald in conversation with Michael Shapiro, 4pm, Saturday, Oct. 18, Book Passage Corte Madera, 51 Tamal Vista Blvd.