As a child, camping meant staking out a luxurious acre inside the Ted Shed: my family’s Sears & Roebuck “Ted Williams Signature” tent, a Taj Mahal of canvas that could have sheltered a football team. When I fled the nest after college, I left behind the massive tarp and bought myself a real backpacking tent: A four-person, three-season REI dome that weighed five times what any experienced adventurer would have considered. To me, after the Shed’s heft of two-stone-eleven, it seemed feather-light. For its first real test, I shouldered it on a September trek around Mt. Rainier on the Wonderland Trail. After I set off alone into the forest, it began to rain. And rain. And then it poured. By the time I reached my first campsite, the properly christened Devil’s Dream, I was soaked. Worry and fear set in. My cold fingers fumbled with the grommets and poles. An hour was lost in the simple act of stove ignition. Dinner was freeze-dried and tasted it. Pooling water lapped at the edges of my tent. I tried to read my book. It was one I’d always meant to get to: Thomas Mann’s The Magic Mountain. It sucked. Capsuled inside a teddy-thin sleeping bag, I passed the night slowly in a wakeful shiver. And then finally, blessedly, dawn and a few rays of sun arrived. I had survived. Looking back now, after 20 years of adventures to the far north, to the South Pacific, to Central America, I realize I did nearly everything wrong that night at Devil’s Dream. But I have no regrets. Your first night doesn’t have to be perfect. In fact, it rarely is, but how else will you learn? Long ago, I rubbished that sheer sleeping bag in favor of a superwarm fatty. My tent now weighs less than my shoes. I carry food that’s real and delicious. My only books are old favorites—James Ellroy’s my go-to guy. Nowadays, when I hunker down in a tent, I’m warm and dry and home—and that awful night at Devil’s Dream was the first step to getting there.