People have asked me to explain why I left a successful career as a New York Times staff writer. Other people wondered about the genesis of Roadmonkey. They’re two sides of the same coin, really. Here’s the story:
I’ll start with a sentence I wrote, in 2010, for MindFood, an Australian monthly that asked me to write a first-person piece on “My Story”:
In 2008, while still on The New York Times staff, I started Roadmonkey Adventure Philanthropy on the idea that I had a clear but time-limited chance to begin a new career that would create adventures of the sort that made me boil with envy when I read about other people having them.
At that point I had been at The Times for 9 years, most of them on the Metro desk, where most young reporters began. During that time I’d covered the New York City jail system at Rikers Island – reporting which led to The Times nominating my work for a Pulitzer Prize. I’d covered the state of Connecticut. I’d covered the post-9/11 anthrax attacks. And I’d gone to Iraq during its most violent period, mid-2006, to report on the war from a fortified bureau across the Tigris River from the depressing, bureaucratic dust-bubble known as the Green Zone. After that, on loan to the Washington bureau, I’d covered the military justice system and several high-profile courts martial and trials of American servicemen accused of crimes in Iraq & Afghanistan.
I had a good career and a solid reputation for noteworthy investigative reporting at the finest news gathering outfit on the planet. But in 2008, with the military trials fading from the public’s interest, I was summoned back to Metro, a lateral move at a time when the paper was closing bureaus, eliminating jobs and struggling to survive the upheavals in digital media. The specter of Metro stood in uninspiring contrast to my dream work: foreign correspondency, and writing the narratives of extraordinary people, events and ideas in the farther reaches of planet Earth.
I understood the context of the politics of my new billet. I knew what it meant to be returned to Metro in my career prime. It meant being back in the land of the eager & very talented young guns from Yale & Princeton waiting to be plucked away by Washington or Foreign to cover this presidential campaign or that overseas conflagration while I remained at HQ with everyone who had spouses and mortgages and kids to support.
The choice revealed itself: I could stay at the The New York Times, maintain my New York City lifestyle and ignore being shelved – the life of “quiet desperation” so many Americans end up living. Or I could do what I told myself, upon my arrival at The Times in 1999, that I had to do if I ever became one the people in the newsroom who stayed long after the paper had much of a use for them: I could leave and forge my own path forward.
For the previous 3 years, I’d been thinking about a company called Roadmonkey that would combine physically challenging outdoor adventures with hands-on volunteer projects that did measurable good in the world. I was inspired by that idea but as a Times reporter there was no room in my schedule to launch a business. As I perceived my fortunes at the paper diminishing, I thought more and more about this Roadmonkey idea. I tested the outlines of the business against the no-bullshit opinions of my friends and colleagues. No one told me I was crazy. Most of them encouraged me, inspired that I’d have the courage to leave The Times voluntarily during a period of great economic and financial uncertainty.
The more I thought of Roadmonkey, the more I liked it. The more I thought of adventure philanthropy, the more I got that quiet, fist-clenched “Yes” feeling in my bones. I thought on it some more – you don’t quit your perch at the highest levels of your profession on a whim. As I considered the arguments for staying and leaving, I became convinced that Roadmonkey was the once-in-a-decade, maybe once-in-a-lifetime chance for me to grab the brass ring and execute.
It was also my chance to reinvigorate my professional ambition and, in the process, overcome the identity-drowning inertia of the The New York Times. I’m very thankful for my career at The Times. But after feeling as I’d been sent to pasture – or at least to a holding pen far from the main stable – it was time to produce, on my own terms, the ambitious vision of my own radiantly imagined future.
In 2008-9, in between Metro articles about Mob-controlled school bus companies in New York, I ran Roadmonkey test expeditions during my accrued vacation time, to see if the idea had merit in the public sphere. Those expeditions were successful and encouraging. As 2009 began, the question for me became, Should I pull the trigger on a business I inherently believed in or would I stay put, take the stable paycheck week after week, live the New York life and eat my ambition for lunch every day in The Times’ light-soaked 14th floor cafeteria?
I wanted no part of any more financial uncertainty in my life. I’d worked hard for my professional reputation at The Times. Was I really going to give it up to launch a travel company during the gravest economic downturn in our lifetimes? Did I have the courage to face down all that uncertainty and do what I knew in my gut I had to do? Could I stand up, fight off the corporate inertia and be the person I told myself I wanted to be?
Could I be a roadmonkey?
You have but one life. Live it like you mean it. I use that phrase nowadays when I tell people what Roadmonkey stands for because I feel its urgency from that time when the easier choice was to stay put and get on with a comfortable but blunted career and vision for my future. Since leaving the paper, the energy I send out into the world has changed, I’m told. I and the ideas I’ve put into action inspire people to change their own lives. That is incredibly powerful and rewarding to understand. It’s what drives me to make Roadmonkey a success.
We’re onto something important and, dare I say, unique. It happened almost by stumbling from one epiphany to the next, not knowing what lay ahead, and pushing ahead anyway on the gut instinct that this has merit, and therefore worth, and therefore potential to change the world as we know it.