Tips for Coping with Life 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 TripIt.com 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. Traxo.com and Dopplr.com 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.