Tiger Woods, dressed for a crisp autumn day, walks confidently down an uneven slope among trees ablaze with fall colors at their peak. High in the Blue Ridge Mountains outside Asheville, North Carolina, he stops at a white pole that marks the site of what will be the 18th green of his first golf course in the United States. Earlier, a helicopter whisked him from his private plane to this isolated mountaintop, where he is about to shovel some ceremonial dirt. The course itself won’t open for at least two years—probably a good thing given the dismal state of the economy, which has led to the worst golf market in decades.

Yet Woods is all smiles in front of a select crowd. He faces a clutch of photographers, public relations people, and developers, as well as a select group of buyers who would later admit that this moment, this chance to spend time with Woods, was what lured them into the deal in the first place. (View a slideshow about other top athletes going into business.)

“Okay, left foot on the shovel,” a photographer shouts, focusing the crowd’s attention on Woods’ left knee, which is still questionable from surgery. Woods’ career, and possibly the success of this particular patch of dirt, hinges on that knee. If it heals sufficiently, he’ll be able to continue playing at the top of his game, building his legend and thereby increasing the allure of his courses. If not, his marketability will take a ding.

On cue, Woods pushes his left foot down onto the shovel and loosens some dirt. He flicks it forward and flashes a cheesy grin. He switches to his stronger leg and digs two more times, then grips the shovel like a golf club and mugs for the camera. Finally, Woods hands the shovel to an assistant, shakes a few hands, and slides into the Range Rover that will shuttle him to his next commitment.

Woods sketched his first golf course when he was 11. Twenty years later, he founded Tiger Woods Design, which is handling the project in North Carolina. “I don’t do anything quickly,” Woods tells me when we sit down in the clubhouse of a nearby course designed by Jack Nicklaus, the golfer to whom Woods is most often compared. “I think through it. That’s one of the attributes I think that golf has allowed me to learn.”

The course near Asheville is one of three that Woods has under contract. The design and marketing efforts for those courses give the first indication of what his eventual post-pro-golf career may look like, in addition to his exceedingly lucrative endorsement business. “I made a note that I wanted to play all around the world before I got into the business,” he says. “I’ve played every different style of golf course you could possibly imagine.”

What Woods is now undertaking is on a scale unlike anything that he or any other athlete has attempted before. Uncharacteristically, his timing is terrible. He is entering the real estate business just as the economy seems moribund—and if anything, the golf business is in a worse state. The National Golf Foundation, an industry trade group, reported that 2008 was the worst year in two decades for opening new golf courses, with the sluggish real estate market as the leading negative factor. It also noted that 2008 was the third year in a row with “zero to slightly negative net growth in supply”—meaning that more courses went out of business than opened.

Home prices in Hilton Head, South Carolina—among the country’s top golf getaways—fell 10 percent in October, while the number of rounds of golf played there fell between 5 and 20 percent.

But Woods isn’t designing courses at Hilton Head or anywhere near it. His first course in the U.S. will be in the high-end project outside Asheville, the eighth development by Cliffs Communities. He is also designing Punta Brava, a course in Mexico. And his course in Dubai is expected to open later this year, even as declining oil prices have caused a real estate slump there too. All three were conceived in better days but are now sprouting amid massive economic shifts.

For Woods, the collapse of the global golf economy is nothing more than a bad break. Neither he nor his backers will be drawn into hand-wringing over the state of their ventures. But the economic pressures have nevertheless injected an unexpected element of uncertainty into Woods’ business plans, which have shifted from a sure thing to a riskier bet.