Avoid the Unpreparedness Tax – and Other Things I’ve Learned in Airports

Because of my work as a speaker and teacher, I fly frequently - and after spending enough time in airports around the country, I’ve learned a few things through experience and recommendations from others that help make the travel experience smoother, less expensive, and a more enjoyable.

When Packing

  1. Travel light and don’t check luggage. Whether it’s a short overnight trip or you’re traveling internationally for ten days, you need to take less than you think. And carryon luggage is the way to go. It saves you checked bag fees and a ton of time avoiding the long wait at the baggage carousel. Sometimes I’ve been able to get on an earlier flight home because I had all my belongings with me (if not, gate agents won’t allow the switch). A rollaboard is what I use most often, but if it’s a short trip I might use a small duffel bag. Dress in layers, wear a fleece, and try to avoid bringing that big bulky coat in the winter if possible. (I almost always wear a zip up fleece hoody in non-summer months.) I don’t use a Kindle or e-reader, but I don’t bring large, heavy tomes either. Instead, I throw small books and magazines in my backpack.

  2. Pack the right tech: I always bring my AirPods Pro (any form of noise cancelling ear pieces or headphones are a gamechanger) and appropriate chargers.

  3. Bring a water bottle: Staying hydrated while you travel is important. Of course, make sure your water bottle is empty before going through security, then fill it up after you get through. (It’s amazing how many people will pay $8 for a bottle of water when it’s free if you bring your own). Always bring one. No exceptions.

  4. Pack only one extra pair of shoes (and wear your bulkiest shoes on the plane). Shoes takes up a lot of space in luggage and they’re weirdly shaped. I usually bring tennis shoes and dress shoes.

  5. Throw in some Emergen-C packs. I always bring some not because I am sick, but because I don’t want to get sick. I mix it in my water bottle each morning.

  6. Bring a small Ziplock bag. It’s small and lightweight and frequently comes in handy when I need it most.

  7. Pack a small picture frame of the family. I do this so I can take them with me. (ht: Dan Kimball)

When Flying

  1. Download your airline’s app. It makes it so much easier to find your gate, learn of delays or gate changes, and scan your boarding pass.

  2. Arrive at the airport in plenty of time. Some people like to cut it close. I absolutely do not. There are factors out of your control, such as traffic on the way and security lines when you arrive. Once you get past security you can relax and settle in: check email, read a book, make a phone call, go for a walk, etc. Nothing minimizes travel stress more than arriving at the airport in plenty of time.

  3. Always tip your driver. If you use airport parking, tip the driver before you jump off the bus at the terminal. If you take Uber or Lyft, always tip. These people work very hard and are often underpaid – and their livelihood is often dependent upon those tips.

  4. Get TSA Pre-check: if you travel more than 3-4 times a year I would strongly recommend it (or Clear). It eliminates wait lines (and thus, stress) and it’s relatively inexpensive.

  5. Pack snacks. Airport food is wildly expensive and often tastes like cardboard so I avoid spending money there as much as I possibly can. Additionally, it’s really difficult to eat healthily at an airport. With a little intentionality you can save money and time and avoid paying for overpriced hospital food. Packing an apple, banana, a KIND bar, or bag of nuts can hold you over for a while. Sometimes I’ll stop by Wawa and pick up a sandwich that I can easily pack in my backpack on my way to the airport. People who purchase food at the airport pay what I call the Unpreparedness Tax. Pro tip: when the drink cart comes down the aisle on my flight I often ask for tomato juice, as it’s heavy and can be like a liquid meal (ht: Dave Briggs). If I have to order food, I often enjoy ordering out of those refrigerated machines called Farmer’s Fridge which sell salads, grain bowls, wraps, and healthy sandwiches. They taste great and there’s no line.

  6. Remember airport etiquette. Be aware of your surroundings and think ahead. Remember, there are a lot of people around you in the airport and on the plane so it’s easy to be in someone’s way. Here are a few things I’ve learned and tried to embrace.

    -Have your boarding pass ready before getting to the gate agent to scan (and please, for the sake of the rest of us, listen carefully to the announcements so you board with the right group number!).

    -Don’t order a coffee right before boarding a plane, making it difficult for you to hold it while you are schlepping your things to your seat.

    -Be respectful of others around you by stepping out of the aisle so others can move past you (and I beg you: please make sure your backpack/purse/luggage/duffel isn’t banging those who are already seated in the head).

    -Don’t recline your seat (do you like it when the person in front of you reclaims theirs?) and make sure to use earbuds (your phone and iPad should not make noise that others can hear).  

    -When deplaning, thank the flight attendants for their service and, if you have the opportunity, shake the hand of the pilot to say thanks (your life was in his/her hands, so offering a polite thank you is the least we can do).

  7. Be intentional with your time. Decide deliberately whether you connect to the Wi-Fi, even if it’s free and readily available. Think about how you can best use this unique time and place on a plane to be purposeful. I can’t sleep on planes (though I wish I could) so I often prepare/review my notes on the flight to the event and then relax/replenish on the flight home – watch a movie, listen to a podcast, etc. (ht: Jon Acuff).

When Staying in a Hotel:

  1. If staying multiple days, look to see if renting an Airbnb makes the most sense. But if it doesn’t, a hotel is fine.

  2. Designate a specific place in your hotel room for important items. When checking into your hotel room clear off the detritus on the desk or dresser and lay out a small hand towel from the bathroom. On the towel place your important items: keys, wallet, phone, hotel room key, etc. It’ll be easy to know where to place items and know where to find them when you need them on your way out of the room (ht: Daniel Pink).

  3. Turn on the shower to hot and create a “steam room” to iron your clothes. As you unpack your clothes, put your wrinkled dress clothes on hangers and hang them in the bathroom for a few minutes. With the steam the wrinkles fall right out – and you avoid having to lug out that big ironing board.

  4. Hit the hotel gym. Bring workout clothes (and a plastic bag to put your sweaty clothes on the flight home), as it’s important to stay active on the road.

  5. If the light from the hallway coming from under your door is too bright for you to sleep (or if there is hallway noise) roll up a bath towel and put it at the base of the door to block light and noise.  

 When Visiting a New City:

  1. Research ahead of time. It’s amazing what a few minutes of a Google search or ChatGPT can tell me about where I’m going – the history, culture, notable landmarks, geography, and other fun facts. It adds some great texture and fun to the trip.

  2. Go for a walk. If the weather is nice, I try to take a walk (if I’ve been flying I’ve most likely been doing a lot of sitting) and I get to know the new context I’m in. This especially helps when I’m traveling across time zones.

  3. Ask locals what they love (and don’t love) about their city. People love talking about their hometown. I ask hotel clerks, baristas, Uber drivers, and waitresses. I often ask them for some great recommendations for eating. Speaking of that…

  4. Refrain from eating at chain restaurants. Oftentimes when a host picks me up he/she asks where I’d like to eat. I respond: “It doesn’t have to be fancy or expensive, but if we could go to place unique to the area, that’d be great.” I do all I can to avoid eating at “Anywhere USA,”, chains that exist in most places in the country (e.g. Applebee’s, Olive Garden, Chipotle, etc.). I atry the local flavor, the hole-in-the-wall Chinese place, the highly recommended restaurant the locals love, or that taco truck down the street from my hotel. It helps you get to know the region a bit more and make a great memory.

Most of what I’ve learned about travel comes down to one idea: be intentional with a little bit of preparation on the front end and it saves you a lot of money, time, stress, and frustration on the back end.

What about you? What’s the one travel tip you’d never give up?

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