Travel Like a Boss: Expert Tips and Hacks for Remote Workers on the Go

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Remote work is here to stay, and travel is now roaring back. If you work at a remote-first company, it’s likely that you’ll be traveling at least a few times per year to get together with your coworkers or attend events. As we take to the skies again, here are a few favorite tips for an enjoyable, productive, and stress-free travel experience.

Travel Packing Tips

First, your travel experience starts when you pack. The key to packing for a stress-free trip is ensuring you have everything you will need, while avoiding anything extra that you likely won’t use. I’m a recovering excessive-packer, but I’ve found that travel is much simpler when you can pack and thrive with less. The less you bring with you, the easier it is to haul your luggage around! And remember, it’s not just getting your bags on and off the plane.

When you travel for work, you may need to take your bags with you if you checkout in the morning, attend meetings all day and aren’t planning on going back to the hotel before you hit the airport and fly home in the evening. If your bags will likely come with you to work on your last day of travel, it is far more convenient to have a small bag than a large one. For 4 days or less, make every effort to consolidate what you truly need to a carry-on size bag and a personal bag.

Another feature of flying carry-on only is—zero opportunity for your luggage to get lost by the airline if you have a connecting flight because your bag is always with YOU!

The best ways to make sure everything you need will fit without the need for a checked bag include:

  • Invest in high quality luggage that simplifies organization. Last year, I invested in a TravelPro Elite set with a lifetime warranty, and I’m so glad I did!
  • Use packing cubes to organize and compress your clothing to save space
  • Go simple on shoes. 1 professional pair and 1 comfortable pair is my limit. Plan outfits that will minimize the different pairs of shoes you need to bring, because shoes are awkward and hog a TON of space in your bag.
  • Minimize the liquids you need to bring. Obviously if you’re taking everything in a carry-on, you need to ensure it complies with the TSA 3-1-1 rule, but you need to ensure your personal products for your daily routine all fit. I love this toiletry bag that is 3-1-1 compliant and fits everything I need. For my soaps, these small travel containers hold more than enough for a full week. To save space in your 3-1-1 bag, remember that if it’s not liquid, it doesn’t need to be in that bag! Things like deodorant or powder makeup can stay outside the 3-1-1 bag.
  • For women, a quality tote bag that can fit your laptop and necessities is a must. For men, a functional backpack can be perfect for airport travel.
  • Invest in a Kindle to save space and weight by not having to pack multiple books. More on in-flight entertainment in a later section.
  • Pack a few snacks in your personal bag. Travel days and be long between meals and food seems to cost twice as much as normal inside security. It’s always a lifesaver when your stomach starts grumbling to have a protein bar or some mixed nuts handy.
  • Ensure you have a reusable water bottle in your bag, and make sure it’s empty when you arrive at the airport. You can’t bring a full bottle of liquid through security!
  • While you’re packing, ensure you have your airline’s mobile application downloaded on your phone, and ensure you check-in to your flight. Airline apps have real-time updates on your flight, mobile boarding passes, and typically have information and maps of the airport terminals.

Now that you’re all packed, let’s head to the airport!

Airport travel tips for remote workers

Getting to the airport can be stressful, especially if it’s early in the morning. Airports mean lots of people, waiting in lines, and waiting for your flight since airlines typically recommend you plan to arrive at the airport at least 2 hours in advance of your departure time.

Getting to your gate

When leaving home, my husband is usually able to drop me off for early morning trips. While it costs a little more in gas for him to drive both ways, it saves me around ~30 minutes to find a parking spot in the economy lot. Another option is to just take a ride share to & from the airport.

  • If it’s available in your area, use the “schedule a ride” feature on Uber or Lyft. Especially when you’re leaving at 4am to catch an early flight, this can be a lifesaver. Schedule it the night before, BEFORE you go to sleep. Then set your alarm to make sure you don’t miss your ride.
  • Plan to arrive at the airport at least 2 hours before your scheduled departure. This is about enough time to check-in, get through security, grab a bite to eat, and find your gate with a little extra wiggle room.
  • If you travel more than once per year, you need to invest in TSA Precheck (or Global Entry, which automatically gives you Precheck). Precheck makes security WAY easier—you can leave your 3-1-1 bag, laptop, and other items in your bag and just drop it on the conveyor belt. You also can leave your shoes and jacket on and walk right through the scanner. The line is also typically shorter and moves faster than the traditional security line, which saves you time. Several travel rewards credit cards include an annual credit for TSA Precheck or Global Entry registration. (And one registration is good for 5 years).
  • If you travel more than four times per year, I recommend getting Clear. In some airports, the TSA Precheck line can still be pretty long.  Clear allows you to basically cut in front of the entire line with minimal waiting. It also enables you to use biometrics for your ID, so you’re not fumbling to get your ID our or put it back in your bag as you’re trying to throw your bag on the security belt. With Clear if you aren’t checking a bag, you could safely cut your airport arrival time down to 1 hour prior to departure and still make it to your gate with time to spare. One of my favorite travel credit cards offers a CLEAR membership credit.
    • CLEAR + TSA Precheck is a magic combination, and can cut your security time down to just 5 minutes.
  • After you get through security, fill up that reusable water bottle you packed so you can hydrate in the airport and on the plane. Travel days tend to overly dehydrate, so drinking plenty of water is a top priority.

Now, if all went well, you likely have an hour to 90 minutes in the terminal to kill before you board your flight. My favorite way to spend this time is in an airport lounge, which typically has snacks, drinks, and Wi-Fi, as well as a quiet atmosphere away from the noise of the terminal.

Airport Lounge Hacks for Remote Work Trips

Several premium travel cards offer different airport lounge access. Here are a few ways to find a quiet refuge in your favorite airport:

  • Priority Pass has the largest collection of lounges and has come in clutch a few times for me. The first was on my way back from a vacation in Cancun, when I found out the airport didn’t have public Wi-Fi, but the lounge did (I didn’t want to pay for international cell service when my goal was to unplug for the trip). Minute Suites also offer the first hour free if you have Priority Pass. This was a lifesaver after a trip in Philadelphia when I had several hours in the late afternoon to burn before my flight without much sleep the previous night, and I desperately needed a nap. Many Priority Pass locations also include a restaurant dining credit to help you save on your airport food bill. The Amex Platinum, Capital One VentureX, and Chase Sapphire Reserve all offer free Priority Pass membership as a perk.
  • If you’re flying Delta, Delta Sky Club access can be a great perk. Since my home airport is a Delta hub, this club is my go-to. Both the Amex Platinum and Delta Skymiles Reserve offer free Delta Sky Club Access as a perk. As an added benefit, both cards also offer Centurion Lounge access when flying Delta. These clubs have complementary food and beverage, including Starbucks coffee and a bar. Even better, they offer great places to work and Wi-Fi to connect and knock out a few more tasks or meetings while you wait for your flight. It is SO MUCH easier to take a virtual meeting from a sound-proof booth or work with your laptop on a desk as opposed to on your lap in the main terminal.
  • If you live near a United hub, United Club Lounges are another great option. Very similar to the offerings found in a Delta Sky Club, you can get access to these clubs with a United Club card. Wi-Fi, clean workspaces, complementary food and beverage, and a quiet place to decompress before hitting the skies.

When you head to your airport lounge, double check that you know how long it will take you to walk to your gate. I recommend giving yourself 10-20 minutes before boarding starts, depending on how far you need to walk. If you’re planning to get deep in the zone for some focus mode work time while in the lounge, set yourself an alarm for when you need to get up and leave so you don’t miss your flight!

Tips for Passing the time on Your Flight

You basically have five options for in-flight entertainment. You can read, work, use the seat-back shows, sleep, or you can do something on your phone (the last option is least desirable because it drains your cell phone battery quickly).

  • Read: Pack a book (or two) depending on how long your flight is, and how long your trip is. Most trips for remote workers are less than a week and one book will suffice. I’m a relatively fast reader and I also like to switch between 2-3 books depending on what mood I’m in, so I invested in a Kindle Paperwhite and a Kindle Unlimited membership. It’s a slim device that has its own battery (so I’m not draining my phone) and I can load literally thousands of Kindle books on it for an awesome selection. I’ve had mine for almost 3 years, and I don’t go anywhere without it.
  • Work: If your plane doesn’t have Wi-Fi or you don’t want to pay for it, airplanes can be a great time to get work done in focus mode and without distractions. Most planes are now equipped with Wi-Fi so you can stay connected while in the air. If this is something that excites you, Delta started offering free in-air Wi-Fi for Skymiles members this year.
    • A great perk for free in-flight Wi-Fi is using the annual airline fee credit from the Amex Platinum ($200/year) or the Hilton Amex Aspire ($250/year) to pay for your in-flight Wi-Fi. These cards allow you to select ANY major airline, you just have to stick with the same airline for the entire year. Around January, you can change it if you choose.
  • Seat-back movies & TV shows: If you just want to decompress, this can be a great option. Remember to bring corded headphones, or you can usually get a backup pair from a flight attendant.
  • Sleep: If you’re a person who can catch some Zzz’s while sitting up straight and sandwiched between people, then go for it. I still haven’t figured out how to do that. If you fall asleep on me and I don’t know you, I may poke you or obnoxiously shift in my seat until you wake up and stop leaning on me…. sorry not sorry. Personal space is real.
  • Phone: Your phone can be an endless source of entertainment, from watching downloaded movies, to listening to music or an Audible audiobook, to playing a downloaded game. Just remember this drains your battery, so you may want to bring along a solid external battery pack for boosting your power.

After you land and grab your bag (if you just couldn’t resist checking one), then we’ll get into navigation and restaurant hacks!

Navigation, Transportation, and Restaurant Hacks for the Remote Work Traveler

When you arrive, you will most likely have a rental car, use a rideshare app, or local transit to get to your hotel or meeting location.

Here are a few tips to help with the final mile logistics:

  • Download both the Uber and Lyft apps before you leave. You can create a separate business profile with your work email, so the app will send your receipts (including driver tip) directly to your inbox for easy reporting later. Check both apps when you land to see which one offers a better price for transportation.
  • Use a card that gives you bonus points in the transit or travel categories in your Uber and Lyft apps so you can maximize your earnings. Two great cards for this are the Chase Sapphire Reserve and the Amex Green card, which both earn 3x points on Uber and Lyft.
  • If you have coworkers who are landing around the same time as you, plan to meet up at the airport and share a ride to the hotel or meeting location to save money. This transit is nearly always a reimbursable expense, but your company will still likely appreciate you saving them money.
  • If public transit is available, familiarize yourself with the transit options and routes before you leave to reduce stress and get a plan together. Google Maps can be very helpful for planning final mile travel using public transit.
  • Your company may plan group meals and put them on the corporate card, which is great because it is easy for you! However, there will likely still be several meals which you have to pay for yourself. Bring your Chase Sapphire Reserve or Amex Green card with you on your trip, because both cards also earn 3x points on all restaurants!
  • Some companies pay per diem and don’t require submission of food receipts, but other companies DO require you to submit receipts for food and incidentals. If your company requires receipts, remember to save them! An easy way to do this without stuffing receipts in your pocket or bag is to snap a picture on your phone and either upload it directly into your expense app or send it to your work email for ease of submission later.

The tips and tricks for traveling above can help you reduce the stress of travel and enjoy your time away from home. With less stress, it is easier to make the most of your trip and show up as your best self to support your team.

How to Make the Most of Your Travel as a Remote Worker

To make the most of your trip as a remote worker, here are a few final tips to make each trip a huge success:

  • Scope the trip purpose and an agenda before the trip. You should have a clearly stated purpose of what you plan to accomplish by traveling to the same location that couldn’t be accomplished (or at least not as effectively) virtually. By having a plan before you go, everyone will be on the same page and prepared to be effective when they arrive.
  • The purpose of the travel will nearly always have an objective-based outcome linked to team goals. However, if you work in a remote first company, the goal should also be building relationships!
  • Plan a team dinner or activity together. In my experience, virtual communication barriers are greatly reduced after team members have a chance to meet in person for a few days. They’re more willing to reach out to the people they need help with after they’ve spent some time together in person—and that time doesn’t have to be all about getting work done.
  • Include some down time in your schedule. Travel can quickly create a demanding schedule if you’ve planned full days. Be sure to plan in some breaks so your brain can recover, and while your team might want to stay up late, make sure you get enough sleep on your trip to bring the best version of yourself forward each morning.

As a remote worker, one of the best parts about travel is getting to see your coworkers or colleagues in person and build relationships. Grab a few of the tips in this article to help you reduce the stress of travel and focus on the joy of connecting.