William O. Taylor, proud Yankee builder of a billion-dollar company and as worthy a paragon of the Old Economy as I ever met, flashed his eye across the desk, sucked in through clenched patrician teeth and quietly blew me away with his response. “Golly,” he said. “I wish I were in your shoes.”

My shoes? My penniless, no-B-school, no-safety-net, bewildered-wife-and-kids-at-home, so-desperately-full-of-holes-I-was-almost-barefoot, pavement-pounding, risk-kicking shoes making tracks in the New Economy? The leap turned out to be much wilder than I ever imagined. But what a ride! Raw fear. Passion. Creation. Ecstasy and despair. Courageous comrades. Love tested, love proved. Glory and redemption. The whole grand, unbridled human drama as quick as you can say dot-com. This was living large.

And now The New York Times says forget about it. Its Sunday magazine, still stacked by the dog’s bed in my kitchen, devoted most of its first issue this month to a prolonged howl of homesickness for the ironclad certainties of the corporate old country. “Come back, Shane!” the Times seemed to cry out to the disappearing man in the gray flannel suit. Come back and chase away this awful free-agent economy, where every career bobs at its own anchor and nothing is guaranteed, except the chance to get out of bed in the morning and build something new!

We’ve officially arrived at the moment when the country’s media elite have begun to take stock of the digital age. It will be a fascinating contemplation. No one yet knows how such a fluid economy of opportunity and risk will play out as it is embraced far beyond Silicon Valley. You can hear the questions shaping up. Can we stand this much risk taking? These are good questions that we will be working out for years.

But some questions get answered primarily by doers. Imagine the urbane European commentators of the 18th century, relating with dismay how Americans lived rough in the woods, miles from a constable, or later in sod houses (sod!) on the open prairie. And yet they did live that way, and prospered. E-topia is not utopia. Not everyone is going to be a billionaire entrepreneur. Not every newly minted billionaire will still be a billionaire tomorrow. The Nasdaq will rise and fall. And lots of free agents who set sail from the old world to the new will get seasick in the crossing.

I did–in the early days you don’t hear about, before the celebratory press releases roll. It can get mighty chilly when the old salary stops, when your future hangs on a stack of credit cards as big as your fist. It can get dark and choppy when your house is on the line and friends wonder where you’ve taken your family and career and everything that once seemed sure. That’s what risk taking means. But let’s not confuse sunrise with sunset. The new order continues to rise up like a digital New World in our midst. One by one–some gleefully, some kicking and screaming–we are being transformed.

This is a story Americans know in their bones. Our immigrant forebears took a deep breath and crossed the water. Now it’s our turn. Today the little third-bedroom dream that I joined, HomePortfolio.com, has more than 100 voyagers on board, building a bustling Internet marketplace for home design. Our dream is happening. Millions of others have their own dreams great and small that will play out in the crossing.

So which wave are you in, pilgrim? What’s it going to be? Plymouth Rock? Ellis Island? A cold, late dash across the Rio Grande? Or will you stay home and read the newspaper? It’s a free country. Thirty years ago Tom Wolfe hopped on a bus with Ken Kesey and his Merry Pranksters to chronicle the explorations of a new generation of adventurers. Their pranks ran out, but their essential question lives on in every revolutionary time. Are you on the bus or off the bus? Because the bus, my friend, is moving.