Self assurance checklist for the anxious traveler

Travel has always meant possibility and change, and for some people, that means anxiety. Add to this non-refundable fares, tight connections and security theater courtesy of the TSA, and it's easy for the fun to turn into a literal nightmare.

There are people who will tell you to just get over it and enjoy travelling, but for some people, the real benefit happens if they can eliminate the things that trigger the biggest issues.

Some prophylactic measures to consider, extreme steps to transform your internal dialogue:

Five days before you travel, lay out everything you intend to bring with you, all in a special section of your room.
You're not going to be checking bags (that's my dad's first law of travel), so, first, relentlessly trim what you laid out. Second, if it still won't fit in a manageable, small, wheeled bag, ship it ahead of time. Get the name of the person at the bell desk at your hotel, and ship the things you can't live without via UPS or Fedex Ground. Track them and you'll know that they've arrived before you even leave.
Take a photo of everything you intend to pack, all laid out on the floor. In addition to helping you file a claim for some reason, the big bonus is that you never have to worry about whether or not you packed something, because you have a photo of everything you packed, on your phone.
While you're at it, go ahead and get a duplicate of your favorite pillow. Ship it ahead. No, we're not moving in, we're not staying at this hotel forever, and no, it's not the way easygoing travelers do it. But hey, you're not an easygoing traveler, and getting a good night's sleep is worth the few dollars it's going to cost you to add a pillow to the box.
Make a written checklist of everything you're going to do the day you depart. Include, for example, the phone number of the car service, checking the oven light and watering the plants. If it's written down, you don't have to keep it in your active memory so you won't forget it. And once you make the list, you can use it again and again, improving it as you go.
Get your boarding pass the day before. I think every airline offers this now. Get it as a printout, not on your phone, because a printout is easy to check off and put next to your passport, more peace of mind. Print a few copies, why not?
Use Yelp to find a restaurant within 4 miles of the airport. Go there for a meal a few hours before the flight is scheduled to leave. You'd feel stupid getting to the airport three hours early, but having a delicious bowl of tom yum three hours before feels just fine, and then you can completely forget about the issue of traffic.
While on Yelp, check out the neighborhood where you are staying. My guess is that they have stores! Remind yourself that if you need a bobbin or a notion or even a toiletry, you'll probably have no trouble picking one up.
When you park your car, put the parking ticket in your ashtray. After you lock the door, take a picture of where you parked, and email the picture to a friend. No worries about finding the car or the ticket later.
You're thinking of bringing more stuff and checking it. Don't. See #2. Only bring the smallest amount of stuff with you, no giant bags to argue about fitting in the overhead and such.
If you travel with people who get all uptight when they go through security, don't go through security with them. Let them go five minutes before you, and you'll have no issues.
Your favorite necklace that's really hard to take off that freaks out the security machines? Leave it at home. And those boots with 100 laces? Leave all of it at home.
You know that scrum to get on the plane first? Skip it. You have very little luggage, and you can just sit there and relax. No prize for getting on first.
You know that scrum to get off the plane first? Skip it. Particularly people who have trouble wrestling their bags, or racing down the aisle or who might need a wheelchair at the gate. Just let everyone else get off first while you take two minutes to check the email on your phone. No prize for getting off first.
So, there you go. For just a little extra cash and just a little extra time spent, you've eliminated fourteen of the things that get people all stressed in their rush to force reality to match their expectations (or to keep reality from matching their fears).

A bonus: Some people get peace of mind by hiring a car service to meet them at their destination. This always messes me up, because there's the hassle of figuring out where to meet the driver (upstairs? downstairs? which door?). I prefer the random access approach of finding a cab, but highly recommend you have Uber loaded and ready on your phone before you leave. It really does transform the way people travel. (Here's a free ride promo they're running for new users).

And another bonus: the now legendary wrinkle-free packing hack.

Have a good trip.

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