It was September 1993, and I was three hours into a five-month, 1900-kilometre solo cycling journey that would transform me and my view of – and place in – the world. Weeks earlier, I’d bought my ticket to Vietnam with the $1200 insurance payment from the Chicago taxi driver who had smashed into my car’s front end. I’d left my $16,000-a-year wire-service reporter’s job to explore via mountain bike a country that had just begun to reopen to Western, and specifically American, travellers. And I fancied myself a rugged young writer in search of his first foreign dateline.

Dreaming big on a shoestring budget, I was, in short, intent on machine-drilling a new life trajectory that would arc across decades of Livingstonian – or even Therouvian – adventures. And I was failing spectacularly. 
Or so I thought.

When you grow up in the cornfield-ringed suburbs of the American Midwest, not much happens that doesn’t also happen again in a few days’ time. Which is fine if you’re not me, whom I often wished I wasn’t. It was, after all, a predictable life that seemed to satisfy tens of millions of reliable, pleasant people. But following my post-university backpacking trip through Europe, in the summer of 1988, that life suddenly appeared far too small.

I was 26 and a cub journalist in Chicago. I was bored and anxious that this one and only life would ossify before it led me anywhere interesting, and I found myself anxious about my anxiety: why could I not be happy where I was, with what I had? I left for Vietnam – still known by Americans more as a war than a country and, thus, full of opportunity – to begin living up to my own radiantly imagined future.

It is a good idea to chart one’s life course periodically with what I call smart risks. For me, heading jobless to Vietnam turned out to be a fine example of a smart risk. It led directly, if rather circuitously, to a staff reporting job with The New York Times, where I had a hell of a good time covering New York City prisons, corrupt labour unions and eventually the war in Iraq.

To get there from my defeated state on that lonely road to Hai Phong, however, was not simple or easy. Upon returning to the States in early 1994, my Vietnam travels provided an opening to write a few well-received features for a mid-level southern California newspaper, which led to my acceptance to Columbia University’s Graduate School of Journalism, where I applied for and was granted a Fulbright scholarship to live and write in Berlin, which helped me land a job, one year later, at a small paper in upstate Albany, New York. There I exposed waste and fraud in state government thoroughly enough to allow an editor at The New York Times to take the chance 
on hiring me.

During my nearly 11 years at the best newspaper on the planet, my fortunes rose and fell more regularly than the Dow Jones Industrial Average. After The Times nominated my investigative series on privatised prison healthcare for a Pulitzer Prize, I thought I would stay forever. The chance to cover the Iraq war, in 2006 and 2007, at the height of the al-Qaeda-led insurgency, was as extraordinary an experience as I’ve had. It also, paradoxically, led me to leave the paper after it became clear that a regular foreign correspondent’s billet was 
not in my cards.

Exiting the paper felt like a divorce: six months to digest the reality that it was over, followed by a year to point my career in a new direction while pulling a salary as a now-distracted reporter, and finally the act once inconceivable: leaving.

In 2008, while still on 
The New York Times staff, I started Roadmonkey Adventure Philanthropy on the idea that I had, at age 41, a clear but time-limited chance to begin a new career that would provide adventures of the sort that made me boil with envy when I read about other people having them.

Roadmonkey is designed to take small groups of intrepid souls on journeys off the tourist path, in ways that test their limits, and combine that experience with hands-on volunteer projects working with members of local communities in need. 
The idea was to give people bored with the typical brand of vacation a chance to challenge themselves and offer something back to a needy world that had been relatively good to them.

In that way, Roadmonkey is a hybrid of adventure travel and sustainable volunteer work, with certain twists that distinguish it from any other travel or volunteer organisation. For instance, Roadmonkey raises money for the volunteer project that 
our clients complete in a novel way: by asking those clients to tap their social networks for tax-deductible donations. By the time we leave for Vietnam, Peru, Tanzania or Nicaragua, we routinely have $5000 to $10,000 raised for our 
custom-designed project.

Innovative? Assuredly. Saleable to the point of being profitable long term? Not yet sure. I am still a reporter more than an entrepreneur. But in my estimation, this 
is another smart risk in 
life that is eminently worth taking; boredom is simply 
not an option.

I started modestly, using my five weeks of paid holiday from The Times to organise and lead my first expedition – to Vietnam, in November 2008. Nine days of cycling through the rugged northwest, and four days spent building a playground for orphans born with HIV, 
at a facility west of Hanoi.

In July 2009, I next led a group to Tanzania to climb Mt Kilimanjaro and build a clean-drinking-water system and school desks for impoverished students outside Dar es Salaam. My clients spoke of a life-altering experience. This Roadmonkey idea seemed to have legs after all.

Ready to cast myself into the blue as a full-time social entrepreneur, I left The Times in September.

This year we have completed three of our six expeditions – to Nicaragua, where we learned to surf and built a playground for school children in the rural highlands; to Peru, where we rafted the Apurimac River rapids and constructed a dye house from traditional adobe bricks for Quechua women weavers; and, in June, to Tanzania, where another bold group of Roadmonkeys summitted Kilimanjaro and then built a revenue-generating fish pond and a library for a school.

Still to come in 2010: a second Tanzania expedition; a cycling and playground-building expedition to Vietnam’s Central Highlands; and by the grace of whatever god you believe in, an adventure philanthropy expedition to Cuba.

When I say ‘we’, I 
mean mostly me, a half-time assistant I’ve just hired and a few dedicated Roadmonkeys at heart who either barter their public-relations, graphic design and other services or simply provide them free.

It often feels wonderful to be charting the latest new course. I admit I feel quite satisfied that, lying on my deathbed, I won’t feel the dreaded regret for not having pushed life to the maximum.

And yet. There is more to life than career and achievement. Now 43, I turn to the lovable idea of having a family. The more I travel, the more I crave the stability of strong personal relationships. It is a huge relief to realise that, finally, I too want to be accountable to others. For years and years, I didn’t feel that urgency and was bothered by its absence.

Then came along a woman named Esther, who, merely by her presence, changed everything. I’m not sure how she did it, but I’m planning a new, simultaneous career as her partner. I am her version of a smart risk, and I’m thankful for that.

I’m still responsible for leading every Roadmonkey expedition; I will be away from home for about half of next year, hoping to grow a business model I invented with nary a business plan. I need to find a way to pull off 12 exhausting expeditions in 2011. Frankly I’m not sure how I will do it, but I realise that reams of successful entrepreneurs have overcome similar obstacles.

In a way, I’m right back on that road to Hai Phong, unsure where it will lead, wishing for a shortcut that I know does not exist. I embrace the uncertainty in order to defeat it, as I learned long ago that sometimes you need to give yourself up to the world and trust that it 
will guide you home.