In Part 1 of this two-part article, I discussed some of the quirks and speedbumps you might expect when planning a business trip. What happens next? Time for the journey to begin. While some of these tips may apply to all forms of travel, I find it’s far more important to be organized and comfortable when traveling for business, as your schedule is usually not your own, and snafus can mean lost income or opportunities.

Packing Science

If you anticipate bad weather or a tight layover, DO NOT CHECK A BAG. Once a bag is checked, your ability to change flights or fly standby is reduced or removed entirely. Once you’re sure you’re boarding a plane you can usually still gate-check it for free due to overcrowded overheads.

You’re probably familiar with the TSA’s 3-1-1 rule. If not, go buy a box of quart-sized Ziploc bags. You can only bring toiletries in your carryon that fit (in total) inside 1 of those bags. No single toiletry in your carryon can be bigger than 3oz. Yes, it’s amazingly annoying and there’s no end in sight to the policy. Always keep at least one spare quart bag with you, as they tend to either break over time or succumb to a leaking bottle.

You’re also best off if you buy a set of toiletries exclusively for travel and keep this bag in your suitcase, as it’s the most time consuming thing to assemble and Tetris all the pieces back into the bag every time you pack. I have a bit of a Sephora addiction, and use their trial sets, travel sizes, and free samples for my travel kits.

Same applies to chargers – if you can afford spares, get them and keep them in your carryon. Chargers are easy to forget in a rush and a great pain to replace on the road. Make sure your phone charger is in your carry-on, as many planes now have USB or AC power.

Ladies, when traveling with a laptop I’m a fan of purse-nesting – packing my laptop bag with enough empty space that a small purse can fit inside. That way, when I cross security I can pull the purse out when getting coffee or checking my phone, and I can shove the purse back in when boarding (they usually tell you to consolidate back down to 2 bags when boarding.)

It may go without saying, but NEVER pack valuable laptops or other technology in your checked bags. Not only is it putting yourself at risk of theft, but certain battery types are illegal in the cargo compartment. If you’re not TSA Pre-Check, pack your laptop in the outermost pocket of your bag so you can remove it easily in the security line when it’s time.

I’m a big fan of packing cubes – fabric zippered rectangular prisms that you can use to compartmentalize your clothes. I only use 3 but they make a huge difference: one for all my tops, one for socks and underwear, and one for bras and larger socks. Then I can move the cubes around, not the individual pieces. The extra zipper pressure also helps you compress and pack more in, should you need to.

Tide Pens are a traveler’s second best friend, right behind scarves. I’ve had multiple pieces of clothing saved by these modern marvels. Don’t leave home without at least one, but make sure it’s handy as they work best if used immediately after the stain. These pens have literally removed black motor oil from my linen pants before. Magic.

And don’t forget hand sanitizer. Keep it easily reachable and don’t worry about the TSA requirement for this one in the states (I’ve never had them balk at a 1oz bottle of sanitizer outside the plastic baggie.)


I also make it a policy to travel with a basic set of medication. Advil, Immodium, Benadryl, Claritin, a few Day-Quil, Gas-X, Tums, and some Nuun or Emergen-C. If you’re visiting a developing country, see about getting a 3-day travel course of antibiotics (in addition to all the immunizations you’ll need anyway.) Some of these are easier to obtain than others while traveling, but there’s nothing worse than being sick at 2AM the day before a big meeting far from home, and not having the right materials.

BUT! If you are traveling internationally, CHECK YOUR DESTINATION COUNTRY’S CUSTOMS POLICIES. Some countries, like Japan, have strict rules about controlled drugs (like strong pain killers.) Other countries like Korea even control the amounts of over the counter drugs you can bring, like Benadryl. Whenever possible, bring prescriptions in the original containers marked with your names, even if you have to transfer them to a pill case later (Maybe don’t bring your whole 90 day supply in case something happens – bring what you need and leave the rest at home.)

Scarves: A Traveler’s Best Friend

I never leave home without some kind of scarf when I’m traveling, no matter the temperature. Scarves do it all:

  • Provide warmth, especially in an overly cold plane
  • Impromptu eye mask/tent for aiding sleep
  • Modesty layer or headscarf for unexpected trips to churches, mosques, or elsewhere
  • Impromptu face mask when you’re sitting two rows in front of the plague
  • Sun protection outside
  • A makeshift sling if you’ve had a REALLY bad day

I prefer a square scarf as they make great shawls as well as circle scarves depending on the arrangement. In Kenya, I found myself adjusting my scarf constantly; to provide sun protection or hair coverage when I didn’t want to draw attention to myself, and shoulder coverage when going indoors after the heat of the sun. But normal oblong scarves still have many uses.

When Your Plans Change

Most hotels will charge you one night’s stay if you cancel with less than 24-48hrs notice. Still, that can often be worth it. Prepaid hotel stays can be cheaper but nonrefundable, so you’re out of luck if a cancellation happens – be careful!
Flights are far trickier, and almost worth their own post. But always remember that ANY flight you book can be cancelled or changed for NO COST within the first 24 hours of booking. Often you have to call to take advantage of this rule, but it’s a law and even if the airline downplays this policy, you are entitled to this benefit. Once that 24th hour passes, you’re usually looking at $125 minimum PLUS the difference in fare. Notably, Southwest does not (yet) charge change fees. If you need to cancel or change your plans, they’ll give you a credit equal to your original fare to be applied to future travel. Great for the really volatile business travel situations.

Twitter can be your best friend while traveling by air. Most airlines have live customer service support on Twitter to head off problems before they go viral. In particular, I have had live exchanges with Delta, American, and Alaska. Delta was actually very helpful – I Tweeted in duress as an international layover of mine sat gateless at JFK. We were worried we wouldn’t make it through Customs in time for our tight turnaround. They asked for my confirmation code, then replied with the gate # I needed, an update and also put us on standby for the next flight should we miss the first one. (It worked out, but I was far less stressed with that information at my side.)

If all else fails, remember the Kindly Brontosaurus posture. Gate agents are generally more sympathetic to patient, polite travelers who appear to be on business, as business travelers spend more money over time on flights. Avoid yoga pants (as comfy as they are) or at least have a blazer handy to “look the part” if you find yourself at the mercy of the airline, and remember: lean in, take a deep breath, speak calmly, and smile slightly. Ask, don’t demand. If the line is long, call the airline while in line with the airline and have a customer service race.

Sleep, Jetlag, and You

Invest in a travel eyemask and earplugs. Often, these can help you catch some sleep on the plane, which is crucial on redeyes but always helpful. Also, they’re great barriers against overly chatty seatmates.
If you’re often on flights longer than 5 hours or do a redeye frequently, also consider getting an inflatable neck pillow (so much easier to drag around than an actual stuffed neck pillow, and way less touristy.)
Over the counter sleep aids should be used with caution – only on long flights, and be aware that often your body processes medicine at a different rate when in the pressurized cabin. You don’t want to arrive at your destination as a medicated zombie.

Hotel Safety

Don’t let hotels lull you into a false sense of safety. Always lock and deadbolt your door when in your room, especially when abroad. Use hotel safes whenever they are available. I have refused rooms before (as recently as this past business trip) when the deadbolt was not in working order.

Avoid speaking your room number aloud, and if your front desk agent does so, ask if they can switch your room if you are concerned others might have overheard. Most good checkin agents will make a point of NOT speaking your room number, instead saying something like “You’re on the fourth floor, here (pointing at a map)”.

If there is no safe in the room and you must leave valuables, you’re taking a risk, especially with company laptops. If you have no other choice, bury the device(s) under your unmentionables somewhere in a closed bag, and even better, leave the Do Not Disturb sign out to lessen the chances someone will enter your room. And if you don’t feel safe, find yourself a new hotel as soon as possible. We are at our most vulnerable in our lodgings. It’s never a bad idea to trust your gut.

Solo Sanity

Once you’ve taken a few business trips, you’ll find yourself with strong opinions about built-in hair dryers, strangely shaped seemingly useless decorative bed pillows, and complimentary toiletry brands.

You’ll also find yourself on your own in a strange city – rarely will every single meal you eat be booked. My coping strategies include reaching out to friends in the area in advance (if possible), bringing my Kindle to keep me company at the bar when eating alone, and making Skype calls to loved ones on nights where nothing’s planned.

Be careful about social media when traveling, especially if you’re visiting a sensitive client site. Don’t, for example, check in at Social Security headquarters if you’re doing a site visit for a partner.

The Dreaded Reimbursement

Assuming you’re traveling for a company that employs you, you’re probably going to have to go online after your trip and enter all of your expenses. It always sucks. There’s tons of little questions like “did you have a government employee at this meal?” that get super repetitive.

You can save yourself some pain by understanding your company’s receipt requirements fully. For example, Amazon requires receipts for any transaction over $25, which is a very low threshold. Most companies require receipts to be itemized (not the credit card slip but the actual receipt with items purchased), so make sure to grab those when making a purchase. Get in the habit of pulling these out of your wallet each night and storing them, or better yet use your phone camera to capture them if your expenses department accepts copies. I store receipts in a plastic baggie in my carryon as folders tend to bleed receipts after awhile.

I recommend making sure as many of your receipts (hotel, airfare, car) are in email format as possible, as they’re much harder to lose. Keep a note file on your phone for cash expenses like taxis. Don’t forget to note what tip you paid for business meals as the original receipt won’t include that amount. Keep track of the names and titles of anyone eating with you for business.

Bon Voyage

Whatever you do while traveling, take care of yourself and try and stay calm. If that means deep breaths, an extra glass of wine, or playing music in your headphones at all times – the calmer and happier you are, the better you will be treated (paradoxically.) And in a few days (or weeks), you’ll be back at home and appreciate home that much more. Enjoy the journey!