By JON WEINBACH September 22, 2006

For most people, work-life balance means packing lunch for the kids, doing solid work at the office and sneaking an occasional trip to the gym. For Zan Guerry, it means running a $280 million consumer-products company and still finding time to maintain his status as one of the country's top senior tennis players. The 57-year-old CEO of Chattem Inc. just won a doubles title at the U.S. Grass Court championships outside Philadelphia, and has been the United States Tennis Association's No. 1 singles player in three different age groups. "I just happen to love the game, and I like to win," Mr. Guerry says.

CEOs are paid millions of dollars a year, travel on plush private jets and are catered to by attentive staffs. Here's another reason to hate them: Some will also trounce you at your favorite sport. Senior executives from companies such as Bear Stearns, Micron Technology and Toyota are challenging themselves in competitive pursuits from golf and tennis to stunt flying -- and in some cases beating full-time professionals.

Anthony Hsieh, president of online mortgage giant LendingTree.com, with about $370 million in revenue last year, recently pocketed about $200,000 in prize money after winning a major competitive sport-fishing event. Ken Block, the co-founder and chief brand officer of DC Shoes, a division of publicly traded Quiksilver Inc., took the wheel of a rally racing car at this summer's X Games and went home with a bronze medal. There's even a cutthroat bowler: Dallas real-estate mogul John Amend employs a full-time coach, averages 220 and brings in top pros to play in a weekly league with guest bowlers that have included Texas Rangers owner Tom Hicks.

To find the executive suites' top competitors, we canvassed sports organizations and companies, focusing on "C-Level" execs -- such as chief executive officer and chief operating officer -- who've been recognized for excellence in their favorite pastimes. That means some talented vice presidents were ruled out, including Nissan North America marketing vice president Jan Thompson, a 10-handicap golfer. Also omitted were those who excel in activities where excellence is closely tied to spending, such as collecting art or wine, or whose pursuits don't lead to scores, proficiency licenses or rankings. (That meant passing on Chris Clarke, president of executive-search firm Boyden World Corp., who's also a world-class Scottish folk dancer.)

There have always been executives whose competitive streak extends beyond the boardroom, of course, including yacht captains Ted Turner and Larry Ellison, and balloonist Richard Branson. But the influx of top-flight executives into competitions mirrors a heightened national focus on fitness, and it also reflects the growth in competitions for runners, swimmers, even poker players. The number of triathlons, a preferred activity of "chief endurance officers" like Disney's CEO Robert Iger, has exploded: This year, USA Triathlon, the sport's governing body, sanctioned more than 1,900 races, up from about 400 in 1999.

There's even a growing business in catering to gung-ho execs. CEO Challenges, a Boulder, Colo., firm that organizes sports events for C-level managers, got its start five years ago hosting an Ironman race in Lake Placid, N.Y., that attracted 15 participants. Now, its five-event triathlon schedule draws about 40 corporate athletes. Next up, the company will stage its first nationally televised CEO Golf Challenge, and plans to host a CEO fishing tournament next January in Belize.

Management experts say many executives are looking for an outlet and a buffer from a BlackBerry-driven, 24/7 work life. At the same time, these are hard-charging personalities: They're impelled to reach the top of their company, and often can't stop once they get there. "They always need another target, another challenge that puts their off-the-chart energy to use," says Sydney Finkelstein, a professor of strategy and leadership at Dartmouth's Tuck School of Business.

But executives who play too hard or too publicly can find themselves in hot water. In 2001, for example, director Walter Hewlett raised the ire of Hewlett-Packard board members when he skipped a vote on its purchase of Compaq to play cello in a concert. That absence came after he missed a different meeting to bike in a 129-mile California event called the "Death Ride." An executive extracurricular activity can become a particularly sensitive issue at companies that are underperforming or weathering controversy.

"They don't hire you to be a CEO for your extracurricular skills," says Charles Elson, director of the Weinberg Center for Corporate Governance at the University of Delaware. "For the extraordinary amount of money they're making, it's reasonable to expect executives to focus on the job all the time."

A few executives with well-known side interests declined to be interviewed. According to the Web site for the U.S. Golf Association's computerized handicap system, Nationwide Bank CEO Jerry Jurgensen has played 20 rounds since late July, and is now better than a so-called scratch golfer, with a "plus" handicap of 0.6 strokes. And Lucent chief Patricia Russo has a 13 handicap. A spokeswoman for Ms. Russo said she hasn't been playing much recently because of the company's pending merger with Alcatel.

Others remain committed to their hobbies no matter what. Steve Appleton, the chairman and chief executive of Micron Technology, nearly died when his plane crashed when he was performing an aerial exhibition for a corporate video in 2004. His injuries included a broken back, a collapsed lung, torn cartilage throughout his sternum and a two-inch laceration on his forehead. "I'm obviously an aggressive person," says Mr. Appleton, 46, who has Federal Aviation Administration clearance to execute aviation tricks. "It's kind of a cliché, but I'd rather die living than die dying."

Here's a look at senior executives who are recognized as top performers in their extracurricular activities:

Rally Racing Ken Block, 38, co-founder and chief brand officer, DC Shoes, Vista, Calif.

There's no shortage of business and entertainment titans who have been smitten with fast cars. David Letterman has a stake in an Indy Racing League team, and veteran media executive Leo Hindery was part of a three-driver squad that won its division at last year's 24 Hours of Le Mans race. But few have competed as successfully against professional drivers as Ken Block.

At last month's X Games in Los Angeles, Mr. Block finished third -- just a few minutes behind winner Travis Pastrana -- in rally racing, an event that requires drivers to race against the clock on dirt courses, often in remote areas. (It's big in Europe and South America.) Mr. Block, who started driving rally cars only two years ago, won the 2005 Rookie of the Year in Rally America, the top U.S. series, and he's currently third in points this season out of more than 60 drivers.

He also works full time as chief brand officer at DC Shoes, the 150-employee company he co-founded in 1994. Quiksilver bought the company in 2004, and earlier this year Mr. Block gave up the role of company president, but he continues to review shoe designs and direct DC's marketing. (Mr. Block helped create many of the company's earliest skateboarding shoes.) Quiksilver, based in Huntington Beach, Calif., announced earlier this month that earnings per share for the third quarter decreased 80% compared with 2005, and lowered its fourth-quarter earnings targets, largely because of slower sales at its Rossignol ski-equipment brand. Mr. Block says his racing schedule -- about 10 weekends a year -- doesn't interfere with his corporate responsibilities. "I can work well with a laptop," he says.

Mr. Block has had at least two serious crashes during races, including a spill last year when his car hit a tree while turning a corner, spun 180 degrees and slammed into another tree. "We could slow down," Mr. Block says. "But then we couldn't be winning races."

Aerobatic Flying Steve Appleton, 46, chairman, CEO and president, Micron Technology Inc., Boise, Idaho

At most corporate retreats, team-building exercises tend toward karaoke nights and trust walks. At Micron outings, Mr. Appleton has led the memory-chip manufacturer's managers in full-contact ice hockey and off-road-vehicle racing on the coast of Mexico. During one event, a dirt-bike ride in Arizona, Micron's chief operating officer skidded during a turn and broke several ribs -- and had a second biking accident at last year's corporate retreat near Moab, Utah. "We're a hard-charging group," says the oft-injured operating chief, Mark Durcan. "It all starts at the top."

So far Mr. Durcan has declined to take part in his CEO's after-hours obsession: Mr. Appleton is one of the country's most accomplished aerobatic pilots. Only experienced fliers are allowed to take beginner aerobatics courses, and it takes several competency cards from the FAA to earn the right to do the kind of tricks that Mr. Appleton performs -- loops, rolls and inverted stalls at altitudes below 100 feet. Mr. Appleton's 2004 crash didn't end his aerobatic career, and he still flies at five to six air shows a year, often in a red Hawker Hunter fighter jet that he bought from the Singapore Air Force in the '90s.

Mr. Appleton jokes that one of the few things more hazardous than flying is the memory-chip business. He has diversified Micron Technology's product base, moving to become a key supplier of technology for camera phones and mobile media devices. The company's stock is up 33% since January. Douglas Freedman, managing director of American Technology Research in San Francisco, sees an investor benefit in Mr. Appleton's hobby. "He's more available than most CEOs because he can just fly himself to a meeting," Mr. Freedman says. "His travel agent is the FAA."

Triathlon Jamie Maguire, 46, president and CEO, Philadelphia Insurance Companies, Philadelphia

In a crowded field of executive triathletes, we gave the nod to Mr. Maguire, who'll likely complete six triathlons this year, including the Ironman World Championship in Hawaii next month. He qualified for that event by finishing fourth in his age group -- out of more than 219 racers -- at last December's Ironman Florida race, in nine hours and 54 minutes. That's faster than times posted by other notable triathletes, including Jarden CEO Martin Franklin, Denver Broncos owner Pat Bowlen and Citadel Group chief David Varwig, who once hired one of Lance Armstrong's advisers to build him a bike.

The insurance-company boss has used triathlons to motivate workers. The company pays entry fees and hotel costs for employees who take part in Ironman races, covers half the cost of gym memberships and allows lunchtime workouts. Three times a week, Mr. Maguire leads a group of managers in early-morning bike rides and midday pool sessions. So far, he says, about 100 employees have entered distance runs, and about 12 others will compete in triathlons this year. "If you can challenge yourself physically, that has overflow into the business world."

While training for his first Ironman race in 2001, the insurance-company boss suffered a broken neck, jaw, kneecap and left hand after a driver hit him during a morning cycling workout. With his jaw wired shut, he could eat only liquids for eight weeks. Though he says biking is still his strong suit, he returned to cycling with trepidation. "You just have to keep your cool because it's real easy to panic," he says.

Bridge Jimmy Cayne, 72, chairman and CEO, Bear Stearns Cos., New York

Mr. Cayne is the oldest member of our group, and likely the only one who hones his game while sitting at a computer, chomping on a cigar. But two or three times a week, the most powerful man at Bear Stearns can be found playing online bridge against competitors from around the world.

In many ways, he owes his Wall Street career to the game. For several years in his early 30s, Mr. Cayne was a professional bridge player, hustling games all over Manhattan. He eventually scored an invitation to play at the home of Laurence Tisch, the late former chairman of Loews Corp. When he got wind of an opportunity at Bear Stearns, he interviewed with Alan "Ace" Greenberg, then a rising company executive. The two men discovered their shared passion for bridge, launching a personal and professional relationship that continues to this day.

Mr. Cayne isn't as high-ranked as he was during the '70s and '80s, but he's won 11 national bridge tournaments in his career and has played in several "Bermuda Bowl" competitions, the game's most prestigious team event. At the Spingold tournament this past July, one of the three big events on the U.S. circuit, his team finished second. Over the years, he's ruffled some feathers by paying top players to compete on his team, though there's no prize money awarded at bridge tournaments. (Several other players "sponsor" teams as well; Mr. Cayne wouldn't comment on payments for players.) Mr. Cayne wishes more young people played bridge -- which he calls "mind-boggling and beautiful and frustrating" -- and laments the rise of poker, which he dubs a "semi-mindless game."

Bowling John Amend, 57, president, Amend Group, Dallas

Mr. Amend tends to do things in a Texas-size way. His real-estate company was one of Dallas's fastest-growing companies, and then downsized quickly after its biggest client, WorldCom, went bust. His home is a 10-acre replica of George Washington's estate -- it, too, is called Mount Vernon -- that once belonged to legendary oilman H.L. Hunt. So when he rediscovered bowling a few years ago, he built a $1.5 million, 5,000-square-foot home bowling alley with four lanes, a brick pizza oven and an 82-inch high-definition TV. He also brought in a full-time coach and began inviting the sport's top players for exhibitions.

His game soon improved dramatically. His average is 220 a game -- a perfect score is 300 -- and last year, he bowled a 258 to tie his guest Chris Barnes, who's won several titles on the Professional Bowlers Association tour. Mr. Amend says bowling has supplanted everything else in his exercise regimen, and that the sport is "almost aerobic" when he practices alone. Inviting others provides a different benefit. "Bowling enables you to relate to people in a way you can't at basketball games, football games, or even on the golf course," he says.

His Wednesday-night CEO league is now in its fifth season, and several Dallas-area business leaders have played, including Rangers owner Mr. Hicks and Marty Weiland, chairman of Northern Trust Bank of Texas. "It's gotten to the point where people aren't just competitive, but they're actually pretty good," says Mr. Weiland, whose average is around 175. "It's not just about standing there and eating nachos."

Tennis Zan Guerry, 57, chairman and CEO, Chattem Inc., Chattanooga, Tenn.

Mr. Guerry starred on the junior circuit and at Rice University. He turned pro briefly in the '70s, and once beat John McEnroe to qualify for the U.S. Open. He eventually went to Wharton Business School and settled at Chattem, where his father -- also a tennis player -- had served as president since 1958. In 1990, he took over the company, maker of Selsun Blue shampoo, Gold Bond powders and lotions, and the Icy Hot line of muscle-pain relievers. "I obviously test all the new stuff out," he says. One reason he can devote time to tennis: The publicly traded company, with a market capitalization of $650 million, manufactures about 60% of its products in Chattanooga, so Mr. Guerry doesn't have the travel demands of other CEOs. In 2005, sales increased 8% to $279 million.

While balancing work and a competitive schedule would seem to leave little time for anything else, Mr. Guerry's wife says her husband's commitment to tennis helps foster a balance between the office and home. "He says he's not attached to outcome, but he's in a better mood when he wins," says Julie Guerry, who was a competitive swimmer in high school. She says tennis also gives him a sense of individual control that can't be replicated in a team-oriented corporate setting. Her only rule: "I don't ever play with him," she says.

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Here are four other executive achievers:

Gabriel Schwartzman, 29, CEO, Barr Systems, Gainesville, Fla. Achievement: Became chess grandmaster as a teen. At 17, Mr. Schwartzman, a native of Romania, was the world's youngest chess grandmaster. But he gave up the idea of a career in pro chess after winning the U.S. Open of chess as an undergraduate at the University of Florida; the prize money was only about $5,000. After college, he began working at Barr, which makes software and hard ware for corporate printing networks and data systems; he was promoted a few months ago to CEO. He recently tried to use chess as a morale-builder, taking on 10 employees at once during lunch. "It was supposed to be a kind of teamwork exercise," he says. "But I whupped everyone pretty easily."

Jim Press, 59, president, Toyota Motor North America, New York Achievement: In May, swam a 50-meter freestyle race in under 30 seconds. Mr. Press says his hobby is running Toyota -- he's the first American to oversee all of its North American operations at a time when the company continues to gain market share against U.S. auto makers. But he says his real job is swimming. (He isn't straying far from the corporate playbook: Longtime Toyota CEO and Chairman Eiji Toyota was an enthusiastic swimmer.) Mr. Press fits in two pool sessions a day, 90 minutes to two hours each, and has been competing in Masters events since the early '90s. His assistants know not to arrange his schedule without leaving time for the pool. "I'm grumpy when I don't swim. The people around me probably like it when I can get in the water." Though he hasn't won big races, he says: "If I had more time, I could get on the podium. I'd like to be No. 1."

Curt Culver, 54, CEO of MGIC Investment Corp., Milwaukee Achievement: Once beat Arnold Palmer in nine holes. Among executive golfers, Mr. Culver rises to the top: He has won 25 championships at nine clubs and maintains a microscopic handicap of just over two strokes. Golf "makes me a better executive," says Mr. Culver, whose company manages nearly $170 billion in mortgage insurance. "If I couldn't play golf, I wouldn't do this job -- it keeps you real because it's such a humbling game." The real-estate market has been humbling, too. MGIC's revenues fell last quarter as many owners refinanced loans while interest rates were low, and didn't renew their mortgage insurance policies. MGIC's stock price is down about 16% since January, but Mr. Culver says he thinks revenues are on the upswing.

Anthony Hsieh, 41, president, Lendingtree.com Achievement: His boats have won over $1 million in sport-fishing tournaments. Mr. Hsieh has been hooking marlin for two decades and owns four boats, each named "Bad Company." In addition to weekend trips near his Newport Beach, Calif., home, he spends vacation time each July and October at tournaments in Hawaii and Mexico. His teams compete in about eight events a year; at the World Championship Billfish Release Tournament this May in Cabo, his boat caught 30 marlin in three days to win first prize. "The ocean is contagious," he says. Mr. Hsieh figures annual maintenance on his boats is "way beyond" the $1 million his teams have won. His company, a unit of Barry Diller's IAC/InterActiveCorp., has also been affected by the slowing real estate market. In the second quarter, Lendingtree.com's profit dropped nearly 30% compared with the same period in 2005.