I arrived in Afghanistan on the eve of the September parliamentary elections, concluding 30 hours of travel on a commercial flight that dropped toward Kabul in a steep spiral, as if down a drain, to avoid surface-to-air missiles.

I paid five bucks to ride the "free" bus to an outlying parking lot, where my driver and a translator commenced shoving and hip-checking my luggage, including my oversize bike case, into the trunk of their small sedan. We sped along a wide boulevard flanked by coils of razor wire, bullet-scarred barricades half-hiding new four-story homes with gold-plated eaves—the showy "narchitecture" of the nouveau riche, paid for with poppy money or graft from the billions in aid flooding into the country. At the Park Palace guesthouse, armed guards ushered me through three groaning steel doors and two- foot-thick concrete blast walls into a grassy courtyard lined with rosebushes. It was empty except for a blond woman sitting at a picnic table, writing in a notebook. When she saw me, she raised an arm and waved.

This was Shannon Galpin's sixth trip to Afghanistan since starting her nonprofit, Mountain2Mountain, in 2006. For a couple of years, Galpin, a 36-year-old single mom and former Pilates instructor with no prior aid-work experience, had organized fundraisers from her home in Breckenridge, Colorado, to support various NGOs, including the Nepal-based dZi Foundation and Greg Mortenson's Central Asia Institute. By the fall of 2008 she'd decided to focus primarily on women's issues in Afghanistan and, with barely a handful of contacts, bought a plane ticket and flew to Kabul.

"I didn't want to just sit on the sidelines and applaud," says Galpin, who is rangy and Nordic-looking, with light-blue eyes and straight hair trimmed at the shoulders. "Some people think it's crazy, I know, but I seem to thrive when I'm in over my head."

One might conclude, then, that she is flourishing. Galpin currently manages half a dozen projects, including building a school for the deaf, launching a rural midwife-training program, managing literacy programs in women's prisons, and financing a college training course for high school students. With a staff of one—herself—and an annual budget of $80,000, she's kept the projects tracking through private donations, a few impassioned volunteers, and her own charms. (A guy once handed her a $2,000 check after they'd struck up an hourlong conversation in a Vail coffee shop.) But it's been a fitful, month-to-month endeavor with more ideas than money and a future as clouded and uncertain as the country in which it will unfurl. "I'm better at doing than planning," she said at the Park Palace, holding up her notebook to reveal words and phrases, some bolded or double-underlined, scrawled in all directions and across the margins. "This is me," she said with a half-smile.

I'd come to Kabul keen to see how, or if, she was making an impact, and I wasn't sure what to think at first. Was this merely some quixotic attempt to bolster her own self-worth, or an efficient alternative to the lumbering bureaucracies of institutionalized aid?

I was equally intrigued by Galpin's intent to ride her mountain bike across the Panjshir Valley to the top of the Anjuman Pass—a 100-mile, 10,000-vertical-foot undertaking that would be part personal adventure, part peace mission, and, thanks to a handful of simultaneous charity rides organized by volunteers and friends in seven U.S. cities, part fundraiser. The ride was so brazenly ill-advised, so contrary to every convention people held about the place, that their reactions could be summed up in a few simple statements: "You can't," "You shouldn't," and "You'll die," not necessarily in that order.

We had a week or so before we'd find out, so I ate a plate of chicken kebabs with rice and curry and excused my jet-lagged self from the dining room. There was much anxious chatter from the hotel staff about potential election-day violence; the entire metro area was under a strict security lockdown—a situation expats refer to as "White City"—and a few threats had specifically mentioned the Park Palace. I was almost too tired to care.