Travel Hacks for Road Warriors

Most of the readers of this blog know that I do over 100,000 air miles a year, all in the US/Canada.  After 1.5 million air miles, these are my favorite travel tips – I hope they make your business travel better (or if you’re a glass half empty type, I hope they make travel suck less).

  1. Always carry $200+ in cash when you are on the road – because bad things happen, and cash can fix it quickly in almost any situation. Also because the bellmen, servers, drivers, and others who wait on you have hard jobs and get treated like crap all of the time – so throw a $20 at someone who deserves it at least once a month ($240/yr)- it’s a great way to pay it forward and make someone’s day suck a little less.
  2. Be very nice to all of the people at your home airport -know their names, bring them brownies, cookies, and other nice things around the holidays. They don’t make much money, and they can make stuff happen for you when travel gets bad. Ask about the counter people’s families and know their kids names – it will pay off in spades.  Buy the people who clean the airport coffee from time to time, because it’s the right thing to do.
  3. If you’re elite with an airline, use those “attaboy” certificates for outstanding service strategically. Give them out to people at your home airport, and do it publically – this makes me very popular at my home airport.
  4. If you have to fly 50-seat regional jets on Delta, they can’t take the electronic drink tickets – so it’s open bar, if you have to fly on one of those for over an hour and don’t have Comfort+.  (JSYK, Woodford is the best bourbon available on Delta – sorry, Jack)
  5. Electronic Expense Reporting
    • If your company uses Concur, Zoho, or other web-based expense reporting software, get the app – it’s essential, and you can take pics of your receipts as you incur the expenses
    • Manila envelopes for receipts – scan them with your Concur app when you incur them, and get them into the expense report system. Keep the paper – you may need it to get reimbursed if you lose/drop your phone or if the pic is blurry.
    • If you don’t already have a web-based expense reporting app, 1Tap receipts from Receipt Bank is a great tool for organizing your receipts.  You can take pics of them, tag/organize them with, and you can then output them as a PDF file.  Bonus: The data is available as a PDF or as a CSV file.
    • Set up the bank feeds on your credit cards, and pay for everything with them. I try to put everything on my American Express, and it means that I can almost always expense/deduct charges on that card.
    • Also set up the e-mail address for inbound receipts – it lets you just forward the receipts from your e-mail to the address.
    • Print out a copy of your expense reports – if you think you missed an expense item, you can check it against the old expense reports quickly and easily in your home office.
    • Get a decent travel scanner for bulk receipt scanning/light document scanning on the road.  I use a Brother DS-620, but I’ve also used a ScanSnap S1100 in the past. While you won’t need it/take it on most trips, the scanner will do better with crappy printing on receipts than your smartphone camera.
  6. TSA PRE – pay for it, it’s well worth it. If you go to Canada a lot, get a NEXUS card and a Global Entry card so you can largely skip customs. Platinum AX will cover it, and it will save you tons of time and money in change fees when you’re cutting it close on departure times – AND – you can keep your shoes on almost everywhere. If you don’t have PRE, you’re in the amateur/tourist line, and are treated as a second class citizen.
  7. Airlines
    • Use to find the lowest fare which meets your schedule. While it doesn’t show Southwest fares, SWA doesn’t come to Knoxville (my home airport). While I usually travel almost exclusively on Delta (so I don’t have to pay for bag checks, seats, etc.), Kayak shows you the entire competitive landscape so you can avoid getting crushed when your airline pricing goes crazy.
    • You can get receipts on most airline websites from your frequent flyer account – and they’re already PDF’s.
    • Don’t take the last flight out when you’re headed out unless it is unavoidable. The last flight is the most likely to get delayed/cancelled when you have cascading delays due to weather in an area.
    • If you like being a tourist on other people’s money, head out early on a Sunday morning for a Monday AM out of town meeting. I’ve seen the country this way, and it also gives you time for things to go wrong in your travel.
    • When things go sideways in your travel, head for the airport lounge, and if you’re not a member, pay the one day admission price (usually ~$50). The travel fixers there can do things which the ones outside can’t do, and they’ll treat you like a king even if you don’t have any status on the airline – and you can get some decent food. For my money, the soup in the Delta SkyClub goes a long way toward the $50 when things have gone to crap on the road – and the seating is better, with very few screaming children.
    • Platinum AX has a network of lounges you can visit for free or cheap – but it’s a $450/yr annual fee. For that cost, you also get up to $200 rebated of airline fees (onboard food/drinks, seat fees, luggage fees) and they cover your Global Entry/TSA Pre fees, plus they have preferred memberships/discounts with rental car companies, etc.
  8. TripIt Pro is wonderful, and is well worth the $50/year it costs if you’re on the road a lot.
    • It texts you flight status, gates when you have to change planes, and has somehow better data on delays than the airlines.
    • It creates old-school itineraries you can print when you’re about to leave so you can have a paper backup in case you drop your phone, batteries die, etc.
    • It will alert you when you can save big money on an overpriced fare by reticketing.
    • It integrates with Concur, so your plans can flow through to the expense report (still need receipts).
  9. Rental cars – I use Avis a lot, but pick the one your company supports.
    • Preferred/Gold membership is worth it – they hassle you less, and you spend less time in line.  The aforementioned Platinum Amex provides elite frequent traveler status with many rental car and hotel chains.
    • At Avis, if you’re going to drive less than 75 miles, you can pay them $15 to refill the car with gas. While I don’t use this a lot, it’s wonderful when I have a tight time between when my course ends and I am close to missing the last flight out.
  10. Ride Sharing/Taxis
    • Uber always says it’s 5 minutes out, even when it’s 15 minutes out. Deal with it.
    • Order your Uber as soon as you have your bags and head toward the door – or others will get the available cars in small markets.
    • Platinum AX gets you “Uber Select” – basically, they vouch for you and get you the best drivers.
    • Lyft seems to have better drivers lately in big markets – but they may have fewer drivers in smaller markets.
    • Always have a “Plan B” for transportation – I’ve turned on my Uber/Lyft apps super early in the AM and have been told that cars are just not available.
    • TIP YOUR DRIVERS. Their jobs suck, they don’t make much money, and it’s the right thing to do.
  11. Trains/Public Transport
    • On the train, get the business class upgrade – it’s not much more, and it cuts out the riff-raff. I’ve never had a seatmate in a business class car, nor have I had any screaming children.
    • If you’re on Amtrak, get a coffee and take over a table in the dining car with your traveling mate. It’s more comfortable, and first come/first serve. Bring your own sandwich – the train food is pretty close to what you’d get at a convenience store.
    • When the flights are hosed in the northeast corridor, take the train to cities where the planes are flying. I’ve escaped two NYC blizzards which stranded me by air by taking the train to Hartford to catch a plane from there.
    • Google Transit is excellent for mapping your public transit trip. If you’re traveling light (rollaboard + computer bag) public transit is totally doable – but you may get a little sweaty humping your luggage up the stairs in the subway station.
  12. Other Hacks
    • Get an AAA membership – it will save you $5-$10/night on hotels if you ask for the AAA rate.  Another option – AARP will now let everyone join – no age limit- as long as you don’t mind getting mail about insurance plans you may or may not need yet.
    • Use apps like GeniusScan Pro ($10) as a scanner – you can use it to crop/straighten the images, and create nice PDF’s without bringing the scanner.
    • Carry a 10′, three outlet grounded extension cord with you at all times, as well as a small power strip (I use Belkin’s BST300, which has 3 AC plugs and two 2.1A USB outputs – This will let you sit where a seat is available, and being able to split off the current lets you talk your way into a full outlet and make some friends. Write your name on both – they will walk away.
    • Cheap earbuds are necessary because travel is loud. Avoid the big over the ear jobs, and skip the noise cancellation – just have something you can put in your ears.
    • OneNote is essential for taking your notes so you can get to them on the road. If you hand-write notes, scan them and put them into OneNote.  It also will sync with Microsoft OneDrive and OneDrive for Business.
    • MileIQ from Microsoft is amazing for keeping a business mileage log – it’s $60/yr, and well worth it.
    • If you present, have at least 2-3 ways to connect to a projector. I carry a number of devices so I have two ways to connect with any kind of digital input into a projector – HDMI, VGA, DVI – you should be able to use any of them.
    • Carry a 20′ HDMI cable with you – you can use the hotel TV as a second monitor for video calls, and it lets you use your NetFlix membership on the hotel TV. You’d also be surprised how often hotels/conference centers have bad cabling taped down, and you can save the day with this little cable. I carry this one
    • If your presentation has sound/video, work out the details of how the sound gets into the audio on the road.
    • I carry an Amazon Echo Tap with me so I can listen to local radio and my music on the road. This doubles as a backup speaker for embedded videos in my presentations.
    • Cocoon’s Grid It system is outstanding for taking all of your cables, etc. and getting them organized.
    • If you present for a living, carry two ultrabooks with you – I carry a Microsoft Surface Book and a Dell Latitude E7270. Have a backup power supply for the “primary” laptop (Surface Book), as it may be hard to get a power supply on short notice for your laptop on the road.
    • Life is too short for cheap luggage. If you’re a pro road warrior, you should be carrying premium luggage (black nylon) like Tumi, Briggs & Reilly, Victorinox (the good Swiss Army type), Travelpro, or Hartmann. I have carried almost exclusively Tumi, but it’s less expensive than buying Target luggage and replacing every year or so – I get about 7 years out of a set of Tumi, and they repair it for free when it breaks for 2-3 years. Monogramming is also free with Tumi. Tumi also has a luggage tracing system – if you register with them, your bag serial number is registered with Tumi, and the airlines can find you and get your bag back to you.