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Working on the road is getting easier and easier as more and more people do it. I'm not talking about the seasoned road warrior necessarily. One in 5 vacationers works while away from home. Broadband connectivity is a given in most hotels. It's a deal breaker for me. Got have a big pipe if you want my business.
One way I get away with so much travel, short as the trips may be, is that I double up by working on the road. Granted my job and lifestyle accomodates working outside of the office but that's the way I planned it. To some degree many of us can. Think of it as extreme telecommuting.
A laptop and a cell phone are the bare essentials. Replace your laptop's battery if it can't hold a respectable charge, otherwise it's merely a paperweight on a long flight. With more and more people traveling with laptops these days, it's getting harder and harder to find an available outlet in the airport during layovers. Don't count of finding one. Make sure to pack a small, single outlet surge protector. Consider it cheap insurance.
I only book hotels with broadband in the room. Ask before hand if it's wireless. If not, take a short piece of CAT 5 cable with you. The front desk may or may not have one if the room doesn't. Call ahead if need be. I don't consider "free WiFi in the business center" doing me any favors. I want broadband in my room, preferably without a surcharge.
WiFi, often free, is available all over the place, not just Starbucks (though if you travel enough the Starbucks/T-Mobile alliance makes that friendly coffeehouse your ISP away from home.) Start by reading this guide to finding free WiFi. Google free WiFi hotspots before you leave home. It might inspire you to work in some really cool places.
A phone call is a phone call, geography be damned. Who cares if I'm on the road? It rings, I pick it up. I need to talk with someone, I dial the phone. I have a nationwide calling plan that makes roaming charges a thing of the past.
Do I need to mention the need to fully charge your phone before you leave town? I can't believe enough people don't to warrant the quick charge kiosks found in airports. I will confess to having purchased more than one car charger on the road over the years.
Kinkos and other copy shops augment your hotel's business center. I use eFAX so I never have to touch a FAX machine again, sending or receiving. And without a printer in my room I've FAXed things to the hotel's front desk so I get a hardcopy for free.
Pay attention to time zone changes, including the airports where you change planes. Consider configuring your cell phone to detect the local time automatically.
It's worth wandering around airports, hotels, even offices buildings to find a quiet corner away from noise and distractions. The upside is many such places come with nice seating, plants, views, and/or art. Be considerate, you're a guest.
I've found that adjusting your schedule to accomodate being on the road minimizes problems. Checking email quickly whenever I can makes up for the long stretches when I can't. Keeping up with voicemail helps too.