The Freelancer's Guide to Business Travel

By Amanda Wowk

November 27, 2018

Freelancers are a unique breed of business traveler. We’re not bound by corporate travel policies; likewise, we’re not supported by travel and expense teams nor do we have access to cool company perks. And according to Upwork and the Freelancers Union’s most recent “Freelancing in America” study, there’s only going to be more of us in the future—with freelancers predicted to become the majority of the U.S. workforce by 2027. So, how can freelancers—or those aspiring to be—successfully navigate business travel without the resources big companies offer? I asked some veteran freelancers to share their expert tips. Here’s what they had to say.  

Build your freelancer business travel toolkit

As a freelancer, you know which tools you need to do your job. Photographers, you can’t work without your camera and editing program. Writers, you can’t make your deadline without your laptop and pages of notes. These items will be atop your packing list, but what about your business travel toolkit? Do you have everything you need to be successful away from home, too? Here’s what the experts recommend (hint: most of these won’t add any weight to your checked bag):

1. Apps

One of the easiest ways to get organized and stay productive already rests in the palm of your hand, now it’s just a matter of curating the right apps. Freelance writer and photographer Spencer Spellman shared: “I love apps that track and mainstream expenses, as they can do a lot of the financial heavy lifting that I would otherwise have to do every month. I also love to-do list apps, like Todoist. I set these up to send me notifications and email summaries of what I have to do for the day.” Other useful business travel apps our experts love include: TripIt—for keeping all of your travel plans organized in one easy to access spot; WorkFrom—for locating a space to work while traveling; Calm—for taking a break to meditate and refocus; XE—for accessing foreign exchange rates; and Uber—for getting around new cities easily.

2. Gadgets for on-the-go

Next, stock your toolkit with helpful travel gadgets. Spencer recommended always bringing a power bank or electronics charger with you on a business trip, since outlets at airports and on planes can be few and far between. His pro tip? “I especially like solar chargers, because I just set it by the window on the plane and it fuels up.” As a freelancer, you won’t always have the luxury of an ergonomically-friendly workspace. Susan Shain, freelance travel writer, shared: “I started getting neck pain from working on my laptop all the time. So I fixed it by purchasing an external mouse and keyboard and an amazing Roost laptop stand.” If you’re just starting out as a freelancer, some gadgets might seem more like luxuries than necessities. So, start with the basics for what you need now, then build your arsenal up slowly. And remember to always track your business-related expenses.

3. Travel credit card

Lee Abbamontetravel blogger, entrepreneur, and the youngest American to travel to every country plus the North and South Poles (whew!) recommended getting a credit card that rewards you for your business travel and spending as it relates to your freelance work. That way, you can maximize your rewards for the business expenses you’re accruing anyway. Most travel credit cards offer a host of additional travel-related perks, too. As always, do your research and ensure you choose a card that works for you, your budget, and your business.

4. Frequent flyer number

As a business traveler, you should sign up for (free!) frequent flyer accounts with every major airline you fly. You should also become a member of hotel loyalty programs. What’s the incentive here? “As an entrepreneur, I’m free to arrange my own travel. This is great for a few reasons, like managing miles and points accumulated on the airlines and hotels I choose. Without being limited by corporate rules and partnerships with certain airlines, hotels or even fare classes, I’m able to obtain status and upgrades with the airlines I prefer,” said Lee.

5. Known traveler program memberships

Finally, save time—and your sanity—by signing up for known traveler programs like TSA PreCheck, Global Entry, and CLEAR. These programs help you skip the long lines at security, reducing stress and ensuring your business trips run as smoothly as possible. Tip: When you become a TripIt Pro member, you receive a four month free trial of CLEAR. That’s four free months to test our experts’ advice—what do you have to lose?  

Develop a travel routine

Our experts agreed that developing a travel routine is critical for staying productive. Whether you work from the air (or not), prefer a coffee shop to a hotel lobby, or get the most creative work done when you’re disconnected from Wi-Fi, the key to success is defining the routine that works for you as a freelancer. “I find traveling to be my most productive time because you’re captive and it kind of forces you to work. I utilize airport lounges and Wi-Fi in airports and on planes. It helps to pass the time and it’s better than watching the same plane movie for the eighth time! Also I bring and use noise cancelling headphones. They really do help,” said Lee. On the flip side, both Spencer and Susan prefer flying without access to Wi-Fi. Spencer said: “I recommend turning off notifications and social media when on a plane. I'm most productive when I’m flying, in part because I've turned off notifications. Being on the plane is a great time to really get down to the work that requires my creativity and attention, like writing or editing.” And Susan agreed, adding that without Wi-Fi she has hours of writing time—without the distractions of emails, news, or Twitter. Personally, I’m a big fan of working on trains. I have access to Wi-Fi if I need to Google a synonym, the leg room is unparalleled, and there’s usually ample power outlets available if I neglected to charge my laptop beforehand. You’re not alone, however, if making time to work is a struggle when you’re on the road. Susan’s advice? “Don't over-schedule yourself. It's tempting to try to see and do everything, but I've found I'm much more efficient—and happy—if I block off full mornings for work, then leave meetings and sightseeing for the afternoon.” Of course, sussing out a travel routine won’t happen without learning a few lessons along the way. Mario Armstrong, Digital Lifestyle Expert, podcaster, and Emmy-winning talk show host, shared: “Don’t waste time finding a place to work from. Join a national co-working program like WeWork or find one located where you travel to frequently. If that’s too pricey right now, always find out what the hotel offers ahead of getting there—is there Wi-Fi? Is it available everywhere? Or only in the lobby or rooms?” Sorting out the details of when and where you’ll work on your business trip ahead of time will save you time—and money—once you arrive at your destination.  

Stay on top of your expenses and taxes

Speaking of money, when it comes to administrative tasks Spencer put it best: “Budget, expenses and taxes are the most challenging part about being a freelancer, and I'd venture to say that it's why more people don't freelance.” By a show of hands, who agrees? *author raises hand* But since you are a freelancer, it’s critical to stay on top of your business travel expenses and, of course, your taxes. The veteran freelancers agreed that hiring an accountant, having a clear budget in mind, and tracking every expense proved critical to sustaining a freelance life. Hannah Logan, freelance travel blogger at Eat Sleep Breathe Travel, shared her go-to trick for managing taxes: “Working as a freelancer I have numerous clients from around the world. Each pays in a different currency on a different schedule. I use Excel to keep track of the conversion rate into my local currency at the time I receive payment, which makes it much easier when tax season rolls around.”  

Cash in on (hard-earned) perks

As freelancers, we’re not tethered to the 9-to-5 world. If you’ve recently transitioned from a corporate job, a new style of working can take some getting used to. It can be easy to fall prey to constantly saying yes to work because we either need or want to make the money—or we don't know when the next assignment will manifest. This attitude towards work often leads to overworking and burning out. Most freelancers took to this style of work for the freedom. So it’s important to make the time to enjoy that hard-earned freedom, too. Those airline miles you’ve tallied up? They’re great for getting you to your next freelance assignment… or, your next vacation. If you decide to use a travel credit card for your business travel expenses, cash in on the points you’ve accrued for leisure trips or self-care activities. As a freelancer, how you spend your credit card points and airline miles is entirely up to you. Finally, let’s not forget about the most precious freelancer perk of all—time. Dictating when you do your work is as liberating as getting to dictate where. The key is to find what works best for you. A final tip from Hannah: “Try to find a balance. When I travel I want to explore, not spend my time holed up at a table with my laptop. However, that kind of attitude doesn’t pay the bills and basically defeats the goal of being a digital nomad. I work best early in the morning, so I get up early and do a few hours before heading out to explore.”   What tips do you have for freelancers traveling for business? Tweet us @TripIt.