How to Travel Like a Neurotic Pro

This year, I’ve been on over a 120 airplanes and travelled nearly 100,000 miles. I am on a first-name basis with gate agents. It’s been like this for the last seven years. I am perversely proud of it. Here’s what I’ve learned.

Marry Your Vendors

  • Don’t spread your love around like a strumpet. Pick an airline and stick with it. Before long, you’ll have status, and that matters. You won’t get bumped, you’re first in line for standbys, you’ll have your own customer service queue (really!), and you’ll get free upgrades.
  • The same goes for car rentals and hotels.
  • Still, you should register for every Preferred program you can get your hands on, even if you never plan to use that vendor again. You’ll be glad you did, especially with hotels who can be very gracious after just a few stays.
  • Put their customer service numbers in your phone.
  • Put all your frequent flyer numbers in your phone.
  • Airlines often have frequent flyer deals with hotels and car rentals. I haven’t paid attention to this, but some people make a science of it.
  • Pay close attention to the specials they’re running. You can often buy into a higher status if you’re shy a few miles or segments.
  • AAA will pay for itself with your first hotel discount.

Choosing Flights

  • Early morning flights are more likely to take off on time, but the TSA lines are longer. Plan ahead.
  • Do not ever take the red-eye. It is never, ever worth it. Ever. Even if you’re 18 and full of recuperative powers, it will mess with your head.
  • If you must take the red-eye, don’t fool around. Hydrate. Avoid alcohol. I’ve found that 6mg of melatonin will put me down in a hurry. Don’t kid yourself and make plans for the next day. You’re going to be a lunatic until you get a good night’s sleep.
  • Don’t log into the airline’s website before you book your flight. I’m nearly certain they play games with the prices for customers they know.
  • Same goes for hotels and cars.
  • For each stop, think about where you’ll stay if the next plane doesn’t take off: if you’re in Atlanta, you’re screwed.
  • If you have your choice of airports for the departures, favor the ones with TSA Pre-Check.
  • Use ITA to find flights. Their UI is the best, and they have the truest data on what’s sold and what’s not.

Choosing Seats

  • Once boarded, your primary goal is to get out as quickly as possible. The difference between sitting in the front and sitting in the back can be 15 minutes. With a tight connection, that puts your plans at risk. Sit in the front of the plane.
  • Beware the seats in front of the exit rows and avoid the last aisle. Those seats won’t recline.
  • Domestic first class seats are great as an upgrade, but usually not worth paying for.
  • It’s easier to sleep in a window seat.
  • You get more horizontal space on the aisle, because you can lean out.
  • Many strongly recommend Seat Guru, although I find “up-front and on the aisle” is advice enough for me. Toan takes it to the next level: “Think about your seating strategy as it relates to your direction of travel and time of day. Flying from Austin to Chicago on a 6am flight? Sun will be coming up from the east so pick a port side seat unless you want the rising sun in your eyes while you try to catch some zzzz’s.”
  • It’s often easier to sleep face-down on your tray than trying to bobble-head.
  • Stick a pillow in the hollow of your back, it will make the seat much more comfortable.

Choosing Hotels

  • Again, stick with one chain to maximize your rewards.
  • Spend a couple dollars more. The differences between a Fairfield Inn and a Marriott Courtyard is definable and usually worth it.

On Checking Bags

  • Do not check a bag.
  • If you check a bag, it will make airlines reluctant to give you a different or earlier flight.
  • Do not ever check a bag.
  • Do not ever gate-check a bag. They won’t lose it, but it will cost you at least 10 minutes of waiting for the air-stevedores to pull it out of the plane.

Choosing the Carry-On

  • If you’re wearing a suit, prefer a garment bag. Clever YouTube videos about folding suits into a roller board will fill you with misplaced hope.
  • If you’re not wearing a suit, you will save your back, shoulder, elbow, and neck by using a roller board.
  • If you are flying on a Canadair Regional Jet, make sure you have a small roller board or carry your things in a duffle, like a gentleman. Most garment bags will fit. Otherwise, they’ll make you gate-check.
  • The Muji garment bags are magic and apparently no longer for sale. They zip in half, have two interior pockets, one massive exterior pocket, and you can still get on a CRJ if you overpack. They can be murder on your back, though. If it’s feeling heavy, it’s time to get a rolling garment bag.
  • I fly on a lot of CRJs, so I’m using the small version of the Muji 4-wheel Roller Board. I’ve lived out of one of these for ten days at a time. It’s not pleasant, but it’s possible.
  • Briggs and Reilly has a pretty fantastic rolling garment bag, U374. I recently picked one up, and I can’t think of any way to improve it. It’s so great, I’ll gate-check on a CRJ to use it.

Packing: The Carry-On

  • Plan your wardrobe around brown shoes. Wear one pair on the flight, and pack the other. They’ll go with almost everything. If you’re wearing sneakers and have black and brown shoes in your carryon, you’re doing it wrong.
  • Get little felt bags for your shoes and use them. Finding scuffs when I unpack makes me crazy.
  • Put your shirts in a folder. I use the Eagle Creek variety. It keeps them safe and relatively un-wrinkled and they’re totally worth the space they waste.
  • Sandwich-style packing is great for saving space.
    • If your roller board has hollows at the bottom, stick the shoes there to save space.
    • Roll socks, underwear and tshirts as tightly as possible.
    • Use the rolls to fill the gaps between shoes and elsewhere.
    • Jeans and trousers get folded two or three times, depending on the size of the bag, and placed atop the folder. Jeans first, then trousers.
    • If your carryon has a little compression flap, use that to wrap the whole sandwich.
    • In a pinch, you can fold a suit jacket over that tightly-packed wad.
  • If you’re not into sandwiches, packing cubes keep everything tidy. They come in many styles and flavors. The best have zippers on either side of the cube, so you can migrate dirty clothes on one side without contaminating the clean side.
  • The carry-on is for clothes. Papers, electronics, and toiletries go in the personal item. Otherwise, it will slow you down at the TSA and if, for whatever reason, you have to check the bag, you won’t have to repack.
  • Pack light. I mean it. Shirts can be worn again, really. Hotels have laundry services. With practice, you can go a week out of a small roller board.

Choosing the Personal Item

  • Choose a design that is TSA-approved, whether it’s a clamshell, a trifold… whatever you like. Just don’t go for your laptop and pull out a phone charger and a half a Snickers, because I will judge you. Harshly.
  • Backpacks are great for casual travel, but if you’re wearing a suit, it’s just a mess. Don’t wear a backpack with a suit.
  • Pick once. Choose one bag, and let that be your personal item forever.
  • Ideally, your personal item is the same bag you bring to work every day, plus toiletries and medication. If you’re repacking a personal item every time you travel, you’re wasting your time.
  • The Tom Bihn Checkpoint Flyer was my mainstay for a while. The tri-fold design made it easy through TSA, the pocket in the back slipped over the handlebars of my roller board, and the front pockets were crazy spacious. I tethered my 3-1-1 bag to the pocket, and could sail through TSA with one hand.
  • Unfortunately, rolling into formal meetings with the Checkpoint Flyer didn’t feel quite right, so I switched to the Jack Spade Nylon Laptop Briefcase. It’s a little spendy for me, but looks great in a formal business setting and holds nearly as much stuff as the Checkpoint Flyer.

Packing: The Personal Item

  • This is your constant companion, and the most important thing you’re carrying. Do not mess around.
  • Your personal item should hold everything you need to survive an overnight in the airport. This includes toiletries, medication, and all electronics. Especially the electronics, because the personal item is the only thing guaranteed to be under your control in all circumstances.
  • Buy and use a portable battery, so you don’t have to roam the airport looking for outlets like a runty antelope. I like the Morphie bricks.
  • Protein bars, peanuts, and almonds. You never know when you’ll be delayed and all the shops will be closed. Protein fills you up without the sugar tummy.
  • Consider using the hotel’s hair conditioner instead of packing shaving cream. It works!
  • Bring headphones. In-ear are best because they don’t take up space. I have been using the Zagg ear goggles for years.
  • I haven’t felt the need for the noise-canceling kind. Too bulky. I just use white- or brown-noise generating apps on my phone.
  • I keep a separate bag with a car charger, EZ Pass brick, and other accessories that I can pack if I’m renting a car.
  • Pack your passport in your personal item. If you lose your wallet, you can still get home.
  • Make sure your 3-1-1 bag and laptop are easily accessible or I will open fire on you with my mind-bullets.
  • Make sure your 3-1-1 bag and laptop are easily repackable. Most folks get the “accessible” part right, and then can’t get all the stuff back in promptly.
  • Practice: pack and repack a few times to take best advantage of the container. It’ll prevent awkward fumbling later and ensure that you’re making the best use of the space you have. I’m not kidding about this. Habit and ritual are what get you through the disorientation of travel.

Security and the TSA

  • Do whatever it takes to get into the TSA Pre-Check program. It’s like flying in 1987.
  • Wear shoes that come off easily. Don’t be the guy with boots. Everyone hates boot guy.
  • That rushed, harried feeling you have in the line for the scanner is trying to help you. Keep moving, and stay out of the way.
  • Do not argue with the TSA. They will insult you, they will be rude. They will stop you for a host of silly reasons. Unless you have four hours to spare before your next flight, let them do their thing and get out of there. The only exception is if they’ve violated you or otherwise broken the law. In that case, make as big a stink as possible, take photos, and blog that junk.
  • If you’re wearing a suit, don’t wear a belt. It probably looks better without a belt, anyway.
  • If you’re wearing a jacket, stuff the pockets with your metal items and send that through the machine. Easier than using your personal item.
  • Shoes first through the scanner. Put them on as soon as they come out.
  • If you’re flying in the morning or evening on a Monday or Friday, expect long lines.

At the Airport

  • If you wear sweatpants or a track suit to fly, you are a non-combatant in the game of life. Dress like a grown-up.
  • Record your parking space, hotel, and car arrangements in your phone. I use and enjoy TripIt, which makes this ridiculously easy. As a bonus, the TripIt calendar integration will block off your flight times from your calendar.
  • When flying into a new airport for the first time, ask the TSA guard by the exit about the usual wait times for your return flight.

Handling Delays and Rebooks

  • For every interaction with a gate agent, ask yourself: are they in a good mood? If they are not in a good mood, they will do you no favors. Be pleasant. Be funny. Make them feel good about helping you. Screaming, anger, being sullen: these get you absolutely nowhere. They get paid whether you fly or not.
  • If your flight is cancelled, you are now in a race for your life. Your only goal is to talk to a customer service person as soon as possible. Everyone between you and that CSR decreases your chance of getting the next flight and increases your chance of spending the night in an airport. So: walk immediately to the nearest service desk and simultaneously get on the phone with the airline. Now you have two chances to talk to a human instead of one.
  • If your flight is delayed, wait patiently. Do not sigh loudly. Do not make jokes about the quality of the airline. Absolutely do not get belligerent with the gate agents. The only person in control of the situation is the engineer, and they’re on the tarmac, not in the terminal. Sit there and read your book like a grown-up.
  • If a delay means less than 30 minutes to get to your connecting flight, you will be automatically rebooked on another flight. You will probably not like whatever flight they gave you. If the gate agent is harried or annoyed at this point, get on the phone. If they appear pleasant, ask them about alternate arrangements.
  • If your airline provides compliment cards that reward their staff, use them as bait. I’m brazen about it. If I need an extraordinary favor from an agent, I’ll pull a blank compliment card out and fiddle with it while I’m talking to them. It’s crass, but besides making them feel good about themselves, it’s the only incentive you have.

Eating and Drinking

  • No matter how good it sounds, don’t eat the pizza or the bean and cheese burritos. You’ll be smuggling them onto the next flight in your stomach, and that’s not good for anyone.
  • Stick to water, the vegetable boxes they sell out of refrigerated displays (Starbucks has the best of these), and bags of nuts and trail mix. Get a solid meal once you arrive.
  • Candy-belly is my mortal enemy. Swedish Fish and Mike & Ikes, especially. One 45-minute commuter flight later, and I have a pound of gelatin in my stomach. Learn from my mistakes, no matter how many times I make them.
  • I’m not kidding about staying hydrated. Force fluids.
  • Do not eat or bring a drink onto the plane. It slows you down, and it smells disgusting. I’m really not kidding. How were you planning to get your carryon into the overhead with a cheeseburger and large soda in your hand? So rude. You can wait 20 minutes to get a drink once you’re in the air.
  • This goes double for fried foods and Mexican. If you bring Mexican food onto a plane, you are first against the wall when the revolution comes.
  • Airplane food isn’t bad nowadays, but don’t pay for it. It’s all a rip-off.
  • Alcohol gives me leg jitters and prevents me from sleeping well. It’s often worth it.

In the Air

  • Don’t put your carry on items in the storage bin over your head. Use the space across the aisle instead. That way you can see them, and yell at the person squishing your laptop, balling up your jacket, etc.
  • Chat up your flight attendants. Ask them where they’re based, and which day of their three-day shift they’re on. They’re professional small-talkers, and they’ll appreciate your expertise.
  • I am not your personal entertainment system. Exchange a few pleasantries, and then shut up. This greases the wheels for later negotiations over armrest territory, and makes everything more pleasant.
  • If, for whatever reason, you want to strike up a conversation, give the other person an out: “Sorry, I know I like to be with myself on planes/in a terminal. Please feel free to go back to your business, but do you mind if we talk about X?”
  • The antidote to chatty seatmates is headphones. It’s an unambiguous way of indicating that a conversation is over.
  • Do your seatmates a favor and lift up the armrest so they can get by.
  • If you’re on the aisle, use the latch under the aisle-side armrest. Boom, two more inches of space.
  • Shut the bathroom door when you are done. Someone has to sit next to it.
  • When they tell you to turn off your electronics on the airplane, do it.
  • Don’t be Phone Guy.
  • When choosing what movies to watch on your tablet, remember that everyone three aisles back will be watching it with you. Keep it family-friendly.
  • Do not use the seat in front of you for leverage. Someone’s sitting there, and you’ll wake them up.
  • Do not use a seat-back to steady yourself in the aisle. Use the overheads instead.
  • Get off the plane ASAP. There are people waiting, and they’re in a hurry. You’re in a hurry, too, because you want to get to the taxi line before all these other jokers.

At the Hotel

  • Hotels on the high end will charge you for everything.
  • Mid-tier hotels without a gift shop will provide things like toothpaste, razors, etc. gratis. Stock up.
  • Use the plastic laundry bag to pack your gym clothes.
  • Forgot collar stays? Create your own bespokes with a room key and your dop bag scissors.
  • If you forget something at a hotel, they’ll store your things in a bag with a room number and a date. Call right away, and they’ll mail them to you. The process works.
  • Paul suggests “put your do not disturb sign on the door but fold the corner. that way after a long customer dinner and multiple different city tour, you find your room with a high level of assurance.”
  • Toan suggests “If you are traveling to the same destination for longer than a week, do yourself a favor and figure out a laundry mat nearby. No need to pay $6 for a pair of socks to get cleaned and no need to pack 2 weeks worth of clothing.”
  • A scientific survey of my co-workers yields three sleep-aid recommendations: Advil PM, melatonin, and Ambien. (YMMV, IANAD, etc.)

In the Terminal

  • As Merlin Mann says: “Keep moving. Get out of the way.” People have to catch their flights, and you’re making that difficult.
  • Do not, under any circumstances, suddenly stop walking in a terminal. 17 times out of 20, there is someone behind you who nearly spilled their coffee. 1 time out of 20, that person is me.
  • Do not look in one direction and walk in another. This isn’t Times Square, and you’re messing with the vector math I’ve done on everyone’s trajectory.
  • Speaking of Times Square: Parties of two or more should abstain from walking shoulder to shoulder. There is a high likelihood that someone wants to pass you, your grandmother and your children in order to make their flight.
  • This also means keeping yourself and your luggage on the right side of the escalator or moving walkway. Let people pass you.
  • You will always be in a rush, but don’t get caught up. You can be moving quickly and efficiently and still be calm inside. Breathe.

[Thanks to the Red Hat Public Sector team, who are some of the smartest people I know on this and many other topics. Especially: Toan Do, Dan McGuan, Paul Smith, Adam Clater, Bob St. Clair, Rick Ring, David Egts, Matt Jamison, and Justin Nemmers, who mentored me when I was a lowly Silver. Thanks also to Madhava Jay for the elevator expertise.]

2 thoughts on “How to Travel Like a Neurotic Pro

  1. Wow! Seriously so perfect! I agree with about 97% of this, the only remaining 3% being around small things like bag choice, etc. You forgot to mention doing your own TSA profiling – I always try to make sure I don’t end up in the same TSA line as the person who looks like they haven’t flown since the Eisenhower Administration – those people are ALWAYS the ones I have to shoot with my mind-bullets! :)


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