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Tips for Coping with Life on the Road

© Marcela Restrepo / Jacky Winter
Can you imagine being away from home 250 nights a year? Hotels' most frequent guests find ways to love their lives on the road.

“When I run my card, the system automatically prompts the desk clerk to greet me with this exact statement: ‘Pleasure to see you again, Mr. Bingham.’ It’s these kinds of systemized, friendly touches that keep my world in orbit.”
—Ryan Bingham (George Clooney), Up in the Air

Many hard-core road warriors recognized a part of themselves in the Oscar-nominated 2009 film Up in the Air, which chronicled the mileage exploits of one Ryan Bingham, a loner who fulfills his quest to earn 10 million American AAdvantage miles and the ultimate ego feed: an engraved (but fictitious) metal card that allows him direct access to his own private flight operator, who greets him by name. George Clooney’s character plays the mileage game and wins, mastering the art of travel along the way. He swipes his top-tier elite loyalty cards with conviction and packs his sole carry-on with military precision.

The need to communicate

Up in the Air didn’t address the most reviled part of any upscale hotel stay: paying for Wi-Fi. At Bingham’s elite level, he probably didn’t have to—Gold and Diamond level members of Hilton’s HHonors now enjoy free Internet access, while other upscale hotel chains often waive the usual Wi-Fi fee for their best customers.

“It’s a paradox why the higher-level hotels charge for Internet service and the lower-end properties do not,” says Cleveland, Ohio–based Steve Belkin, a partner at Sunflower Solutions and a principal at Competitors, a vacation travel experience modeled after The Amazing Race TV show. “To me, it’s counterintuitive.”

Paying $15 a day for a faulty connection just adds insult to injury. When you’re abroad and can’t access your favorite movie or website or have trouble staying connected, use a Virtual Private Network (VPN), suggests Rob Lipman, executive vice president of Cedar Grove, N.J.–based Summit Management Services. A VPN enables users to establish an encrypted connection to their company networks, no matter where they are. On domestic trips, a Novatel MiFi creates a Wi-Fi hotspot anywhere a cellular connection is available, says Andy Abramson, CEO of Del Mar, Calif.–based Comunicano. Similar MiFis are available for overseas connections.

Road warriors say they keep in touch with folks back home via phone, email, text and social-networking sites, and by using local SIM cards to make calls from overseas. Seeing loved ones via Skype is heartening for a lot of travelers. “The technology is good enough now, so it’s actually something to look forward to,” says Bob Beachler, vice president of marketing, operations and systems design for Stretch, located in Sunnyvale, Calif.

Planning, planning, planning

One big challenge of traveling 250-plus nights a year is managing your time. “I can’t say enough how keeps me organized,” says Abramson. Before a trip, he forwards confirmation emails for his flights, hotels, rental cars and restaurant reservations to TripIt, which generates an itinerary on its website that Abramson can import into his computer and phone calendars, then share his trips through email or social-networking sites. and offer similar free services.

Million-miler Gregg Baron, president and CEO of the Success Sciences consultancy in Lutz, Fla., recommends developing a system: He always has a bag semi-packed with toiletries, meds, running shorts, a T-shirt, extra batteries, an iPod and power cords. “Don’t worry about investing a couple of dollars in a second power cord, audio device or set of toiletries,” he says. “It’s worth the convenience.”

Baron uses only a laptop, so he doesn’t have to adjust to different keyboards, and he calls his Tumi attaché case (which fits under an airplane seat) his portable office. Though he often has a GPS system in his rental car, his assistant also prints out large versions of MapQuest maps—so Baron can see them without reading glasses—to get him to his destinations, with the necessary addresses and phone numbers printed on top.

Baron also relies on checklists, so even if he’s distracted while packing, he stays on course. Checklists are also big with Carol Margolis, CEO of Orlando, Fla.-based Smart Women Travelers, who averages 150,000 miles in the air annually. Each of her checklists is a matrix, listing days across the top and clothing items down the side. “I try to wear each top or bottom at least twice to save on luggage space, yet have a different look each day,” she says. “The matrix shows me where I’m using everything and helps me see how jewelry or scarves can enhance the look.” She also schedules everything—even phone calls with friends. “If something’s not on my calendar, chances are it’s not going to happen.”

Keeping up with routines is another way to make a trip feel less wearying, says Ira Peppercorn, president of Ira Peppercorn International, a consulting firm in Alexandria, Va. “Each hotel brings with it the challenges of the lack of familiarity.” The remedy? Stay in the same hotels as often as possible. Troy Bienstock, a senior associate with PricewaterhouseCoopers in New York, says that he asks for the same room when traveling weekly to the same hotel long-term. He may also request restaurant menus ahead of time for an extended stay.

Your hotel’s location can greatly influence your enjoyment of your stay. Stretch’s Beachler, who travels mostly overseas and stays in non-chain accommodations, prefers the convenience and excitement of a thriving downtown, with plenty of access to restaurants and shops.

Seeking comfort

Perhaps the most popular feature in a hotel room is a good bed. “Every time I travel, I thank Barry Sternlicht [founder of Starwood Hotels] for the Heavenly Bed concept,” says Peter J. Bates, founder and president of New York–based Strategic Vision, a marketing communications consultancy. Bienstock concurs—he even ordered one of W Hotels’ beds for his home.

Other travelers put a comprehensive health club at the top of their must-have list for feeling good. A well-lit room, a comfortable chair, a flat-screen TV and a plethora of conveniently located electrical outlets also help make for a better stay. And who doesn’t like a nice robe, plenty of hangers and a powerful showerhead? Plus another essential: a quiet, functioning climate-control system.

Edward Pizzarello, chief executive manager at RMR Capital in Danville, Calif., recommends picking up a cheap humidifier for longer stays at hotels in locales with dry climates, such as Denver and Las Vegas.

Service and upgrades

Belkin, a Starwood Preferred Guest gold-level member, says, “I don’t even fight for status.” He spends enough on the Starwood American Express Card to achieve gold annually. “I get room upgrades 90 percent of the time.”

For the best service, several travelers note that they get to know hotel staffers. Belkin says he writes down who’s who on a “cheat sheet,” greets staff by name and tells them that he appreciates their service. “I get more incremental good service because I recognize them,” he says. “It’s a little effort with lots of payback.”

Consolidating stays at one hotel property or chain has its rewards, too. San Francisco has myriad hotels and deals, but Abramson says that he always stays at the InterContinental on Howard Street, where guest relations hands over his room key in the lobby or the executive lounge, since his credit-card information is already on file. After spending more than 70 nights at this one property, Abramson says he is warmly welcomed and meticulously taken care of during each visit. “This isn’t a hotel experience—they make my road life a ‘home away from home.’” Staff will arrange an airport or railway pickup for him, and he receives unlimited use of the executive lounge. “And, best of all, they have a bathrobe with my name on it waiting in my room for me, along with fresh fruit, chilled bottled water and the room set to the desired temperature before I walk in,” he says.

While very frequent guests usually receive the best treatment, travelers cite Asian hotels as having the best service in the world, regardless of status. At an upscale hotel in Tokyo, says Dan Nainan, a comedian who travels about 195,000 miles a year, “they had these ladies who did nothing all day except stand by the elevator and bow as you got in. It was unbelievable.”

Then there’s the concierge, who often provides restaurant recommendations to busy travelers. Some frequent guests say an honest concierge is a blessing, while others claim that the traditional role has been supplanted by online user reviews and reservation sites, such as


Traveling is a lifestyle some can’t imagine giving up. “Even after 25 years of business travel, I still love walking into a hotel that I’ve never been in before,” says Smart Women Travelers’ Margolis. “I check out the amenities in the bathroom right away and hope for a quality hair dryer and big, thick towels. When I see a robe and/or slippers, I’m always happy.”

What has Margolis learned about the travel lifestyle that she wishes she knew when she started out? “Patience—and don’t sweat the small stuff,” she says. “Whether it’s the kids not having matching outfits when they go to school or a plane that’s an hour late, it’s just not worth stressing over. No harm has come to my kids for not having Mom available every day, and I’ve also always gotten home—maybe late, but always safe.”

Very frequent travelers are somewhat “schizophrenic,” says RMR Capital’s Pizzarello. “I love getting on a plane, checking into a new hotel, experiencing a new city. But that can wear thin quickly, and then I’m revitalized by more time with my loved ones. I generally work as many hours as I can while away and sleep on planes. That gives me a few more precious minutes with family.”

Belkin says that he loves to travel but sometimes feels conflicted about how best to do it. He tries to immerse himself in local culture—he’ll take a rickshaw or a tuk tuk from the Delhi airport, even if it means a 45-minute drive in 115-degree heat—because that’s what the locals do. “But where does it take me? To a well-manicured Sheraton,” Belkin says.

With this in mind, he has some general suggestions for fighting a sense of isolation during business trips: “Get your butt out of the room. Spread yourself around the hotel. Have dinner at the home of your business associates.” Loneliness is a state of mind, not a matter of locale, says Belkin. “You can be lonely in a cubicle at home, or you can be gregarious 10,000 miles away.”

As for the character of Ryan Bingham in Up in the Air, Belkin says, “It wasn’t travel that was the problem for George Clooney. It was George Clooney. He chose to be disconnected.”

KAREN GOODWIN is a contributing editor of Executive Travel.