12 Lessons Learned From a Life On The Road

Traveling is hard work. Here's how to make the best of it

Rule No. 1: Travel is no fun
Really. If you think it’s all about smiling stewardesses attending to your every whim, friendly hotels offering fawning service, and romantic sunsets on the beach, it’s time for a reality check.

Your stewardess will probably stop smiling when you refer to her as one, because no one calls a flight attendant a stewardess and gets away with it today. Your hotel? They’ll be pleasant until you check out. The moment you complain about that surprise $20-a-day resort fee or the $5 charge for receiving a fax, then the grin on the manager’s face will tighten into a grimace of icy resolve. You’ll hear insincere apologies, but you will probably still pay.

And the sunsets on the beach? Last time I went to the beach, there was a hurricane.

Point is, travel can be hard work. Travel can be hard, period.

But when you do it for a living — when you’re a true blue, card-carrying, sleep-deprived business traveler — you learn the ropes quickly. By the time you’re a million-miler, and maybe sooner, you know travel isn’t always fun but you also know travel can be tolerable.

What lessons can you learn from these veterans of the road? I asked some of the most experienced travelers I knew to tell me what traveling has taught them. Here are a dozen of them, in their own words:

Expect nothing
That way, you won’t be disappointed. “Lower your expectations when you travel,” says Steve Powell, an Internet consultant in Orlando. It’s great advice, considering a recent Travelocity survey that found a near total disconnect between what air travelers expect and what they get. As a result, nearly two-thirds of the respondents said they would avoid using an airline altogether if they had a comparable choice. Ouch.

Be nice
Lisa Wiser, a computer consultant from Indianapolis, learned about the power of nice when her flight to Pittsburgh was delayed by weather. The gate agents looked stressed, so she bought them a $7 box of chocolates. “They looked up at me and said ‘What’s this for?’” she remembers. “I said, ‘Because it isn’t your fault, there’s nothing you can do ... but you will be catching hell for this all evening.” No only did she receive two food vouchers, but she also got an unexpected upgrade to first class. It’s true — nice pays.

Never pay cash
Wendy Margules, a real-estate agent from Newtown, Conn., lost $6,000 when she reserved a villa in Cabo San Lucas, Mexico. “The owner asked us to wire transfer the money and fax the contracts back to him right away, and we did,” she says. “Ten weeks later, there was no villa — and he was gone.” Putting your travel purchases on a credit card offers you some protection. Margules could have disputed the charge and received a refund.

Travel light
“The single most important lesson I’ve learned is, pack light,” says Michael Hollander, a manager of a marketing company in Torrance, Calif. “Ask yourself: ‘Can I live without this?’ If the answer is yes, leave it home.” This is particularly important, given that airlines are losing checked luggage at an epidemic rate, while some are beginning to charge their customers a fee for all checked luggage. The less you take, the less you pay for. And the less you can lose.

Have a Plan B
No matter how simple your itinerary, no matter how many times you’ve traveled the same road, no matter how sure you are that nothing will go wrong, don’t go anywhere without a backup plan. “You need a Plan B,” says Alan Brill, an information security consultant from New York. Sometimes, a backup plan can be as simple as looking for another way out. Case in point: a recent flight from Minneapolis to New York, which was canceled for mechanical reasons. It was the last flight of the day. “Long line of yelling passengers,” he remembers. Brill went to another counter, explained his predicament, and was immediately handed hotel vouchers, meal vouchers, and a ticket on the next day’s flight.

Be skeptical
“Don’t believe everything you read,” says Timothy O’Neil-Dunne, a managing partner for a technology consultancy in Claymont, Del. That applies to pretty much anything, from airline schedules to guide books to travel columns. “Do not put your ultimate faith in them. You will be disappointed,” he adds. Which isn’t to say they are totally untrue. O’Neil-Dunne says you should use them as a guide, instead. (As someone who writes a travel column, and has gotten it wrong a time or two, I completely agree.)

Don't trust a reservation
Inga Smith, a photographer from Columbus, Ohio, learned that lesson a few years ago, when her flight was delayed and she tried to check in to a Holiday Inn. “My room was given away to someone who arrived earlier than I did,” she says. “I was sent to another hotel, which was a real dump.” Getting something in writing helps, but always call to confirm. That’s particularly true for an airline reservation.

Visualize first class
Most of us are stuck in economy class, but not all of us stay there. How do people snag upgrades? Well, one of the secrets of frequent travelers is to look the part. “I wear a sport jacket,” says Jason Hupe, a project manager from Long Beach, N.Y. “If they are doing upgrades, then you have a better chance of getting one.” This is true. I’ve spoken with several airline folks who have admitted they’ll pick someone who looks like he belongs in the forward cabin.

Join the club
Even if you don’t plan to collect frequent flier miles (and my advice is to avoid becoming a collector, because points are as addictive as they are useless) you should still become a member of a loyalty program. Rick Damiani did, and it made his trips go a lot smoother. “Before signing up, I was getting selected for additional screening by the TSA,” says Damiani, an applications engineer for and educational computing company in Los Angeles. “But since I became a member, I’ve only been selected twice.”

Keep a photocopy of your passport
It will help you get a replacement much faster when you’ve lost it. Candice Sabatini lost her passport in Paris recently, but was able to secure a replacement within hours because she had a photocopy. “Now I’m always telling others to make sure they have a photocopy of their passport — just in case,” says Sabatini, a publishing consultant in New York.

Get plenty of rest
Travelers tend to be sleep-deprived. And worse, they’re often unaware of how tired and cranky they’ve become. Peter DeForest, a risk management consultant based in San Rafael, Calif., says the importance of a good night’s sleep can’t be understated. “Get some rest,” he advises. “In the morning, you’ll find that what set you off was maybe pretty minor and can be overlooked.”

Enjoy the perks
Despite all the recent cutbacks, travel still has a few things going for it. And even a few freebies. Don’t look the other way when they’re offered. “I steal the soap,” admits Jim Daniel, a traveling salesman based in Stockton, Calif. “I carry a preferred bath soap and shampoo, so I always throw the hotel amenities into the bag with dirty laundry. When I get home, I put them aside to donate to a local homeless teen outreach program.” Again, I’ve spoken with hotel people and they don’t mind their guests taking the soap. That’s who the soap is for, after all.

So there you have it — 12 tips from the people who are in the know. Take their advice with you on your next trip, and you never know. You might actually have ... fun.