Top 5 Travel Tips for the Entrepreneur

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Business traveler

“Twenty years from now you will be more disappointed by the things you didn’t do than by the ones you did do. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover.” Mark Twain


Over the past thirty years or so, I have learned a thing or two about being a global traveler.

Entrepreneurs are known as ‘road warriors’. I’m constantly traveling to different countries around the world. Most oFather and son in Maltaf it is for business, but my family loves to travel too. When the kids were young, we took many long international flights, mostly to Europe. They loved it and still do!

Travel doesn’t have to be tiresome and unmanageable. True, no one can predict airline or other transportation delays, weather issues, crappy hotels with bad service, etc. But, with a good planning you can help make the journey a little more enjoyable. Today, I’ll be sharing some of the tips I have picked up over more than 40 years of travel.

If I had to pick one thing that might relieve some of the stress of traveling, it is: Pack lightly and properly. My prior Navy training has come in very useful in understanding the importance of folding and packing clothes. On board a ship, sailors are provided with a very tiny locker in which to store work and ceremonial dress uniforms. Folding clothes in good order will allow you to take the item and wear it right away without having to find an iron. Shirts, pants, and jackets are difficult to fold, so take a look at this video to find one way to do it.

Today, modern materials include clothing that is lightweight and wrinkle-free. For travel, always use wrinkle-free clothing whenever you can. Typically, whatever creases have appeared during the journey will drop out while on the hanger. Good business and casual shirts are available online from Charles Tyrwhitt, while Orvis has some nice casual choices in both shirts and pants.

I have been able to get my luggage for any length of business trip down to one carry-on suitcase and a messenger bag/briefcase. If you have a bunch of slide decks, catalogs, sell sheets, and the like, consider sending them to your hotel ahead of time.

Here are my top five travel suggestions:

  1. If you are planning to use an internationally sized carry-on suitcase, first plan what you will wear on the journey. For travel, I like to wear jeans with a Packing prepwrinkle-free shirt and a nice jacket. Wear comfortable shoes that will match the clothes you take. Pack one pair of pants and, if you are planning more formal meetings, a suit. Wear a light sweater under your travel jacket if the destination requires warmer clothing (and, sometimes the aircraft can be a bit chilly). Take at least 3 sets of T-shirts, socks, and underwear. Take two formal shirts. (Use the hotel laundry service so you always have a clean shirt for the next day. Most if not all hotels have same-day laundry service). Remember to pack cuff links if you have French cuffs on your shirt, a belt for your pants, and three ties if you wear them.
  2. I’ve got packing toiletries for travel down to a fine art. First, when it comes to taking liquids through security, I’m not a fan of using plastic Ziploc bags. Ziploc bags usually break after a few trips, so consider investing in a more substantial plastic quart size bag. Hair products, moisturizer (yes, your hands will thank you), toothpaste, deodorant and shaving cream (all travel size), will all fit nicely. Don’t pack anything over 3.0 ounces or 100ml because it will be removed and unceremoniously ditched by the security folks. For things like an electric shaver, clippers, toothbrush, hairbrush/comb, travel-size first aid kit, and essential non-liquid medications together with those for upset stomach, flu, motion-sickness, and the like can all be packed safely in a separate toiletry bag. I like the version that can hang of the back of the door. Include items such as cuff links, collar stays, and an emergency sewing kit (because you don’t want to attend meetings with a button missing). Most of these toiletry bags have zippered pockets for safe keeping of those small, loose items.
  3. Over the years I’ve noticed my younger colleagues are remarkably minimalist when it comes to a messenger bag/backpack/briefcase. Gone are the days of the large, bulky black briefcases stuffed with a heavy laptop, papers, and the like. I am not a fan of backpacks but I do like the new smaller, lighter messenger/shoulder bags such as those made by MacCases. They allow for easy packing of my iPad Pro, adapters, chargers, passport holder, a couple of files, earphones, and a small leather billfold with an emergency amount of cash. I found a really useful leather holder from Levenger for harnessing all those pesky cords, plugs, and adapters for your laptop or tablet.
  4. If there is one thing I have learned over the years is that loyalty pays off – in more ways than one of course, but for the frequent traveler, it can pay big dividends. Businesswoman hotelSign up for the frequent flyer program for an airline that operates international service from your closest airport. You will be surprised how quickly those air miles accumulate. The more miles you get, the more benefits you’ll receive. I like the American Airlines AAdvantage program. I linked my account with an AA MasterCard so I get points when shopping. But, I signed up for all the airline frequent flyer programs because you never know when you will need to use another airline. With hotels, for the most part while on business I stick to Marriott (now includes the prestigious Ritz-Carlton brand) and Hilton. Thompson Hotels are a firm favorite for both business and leisure.
  5. Finally, booking your flight and hotel takes time. When searching for the best flights, you really need to look at leaving and arriving at different airports. Even a layover might save you considerable money, so run the searches using different criteria. Also, once I find a flight or hotel that fits my budget on Kayak, Orbitz, and the like, I then check that flight or hotel directly with the airline or hotel website. Sometimes, the flights and hotel rooms are actually cheaper when booking direct and there may be other perks such as an upgrade. You can use your frequent flyer/loyalty points for both hotels and airlines, unless you are saving them up. Also, look at prices/schedules 3 days before and after. With hotels, if you want an unbiased opinion, you have to look at the reviews of other travelers such those posted on Trip Advisor (the best) or Yelp! User reviews will let you know what guests liked and didn’t like. You cannot rely on a hotel star rating. Sometimes it is meaningless. I write reviews on Trip Advisor for hotels and restaurants – good and bad. Entrepreneurs who contribute to these reviews support a great intelligence network for the Road Warrior!

international business dealBONUS TIP: When traveling to a new country, always remember to go with an open mind. People are different the world over. In my experience, the world is not nearly as dangerous as we think it is. Of course you have to be aware of your surroundings and be forever vigilant. Don’t flash money around in public places. Remember to take copies of your passport and credit cards (front and back), and take one copy with you while leaving a copy home with a friend or loved one. (If you lose your passport, contact the nearest US Embassy or Consulate for help, and provide them with the copy and two passport sized photographs so they can issue a temporary travel document or new passport.) Many people overseas are friendly, trustworthy, generous, and willing to provide help and assistance when needed. It is not true that people in all foreign lands hate those of us who come from America. Remember: you are an ambassador of your country when traveling to foreign lands. Please, conduct yourself accordingly!

Travel is exciting and meeting new people can be an enriching and rewarding experience.

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