Remote Work Life: Working While Traveling

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April 27, 2016

Traveling as a remote employee is a privilege, and should never be taken for granted. With the right head on your shoulders, and tools at your disposal, even the most unfathomable of locations can be a reality with a little elbow grease, due diligence, and patience.

A five part series written for remote professionals who want to take their life and careers to a new level. This is the final part in the series. New to the Remote Work Life series? Start at the beginning.

Being a remote worker brings with it quite a lot of responsibility. Both to your employer, but also to yourself. And yet when you get those responsibilities aligned and under control, suddenly a whole host of otherwise unavailable opportunities become options. One of those, most notably, is travel. Other perks may include midday breaks for fitness, afternoon cat naps, or the ability to pick up the kids from school without worry.

Before we jump right in, let me simply state that these thoughts and views surrounding travel tactics are my own. They represent personal experiences, successes, and in some cases, failures! Feel free to leave a comment with your own travel tips to further flesh out these thoughts within this guide to travel for remote workers.


Today I’m working from my home office. As I take a deep breath and extend my gaze up and across the room though the windows, I smile thinking about the options for exploring this world as a remote worker. One of the best things about no longer being tied to a cubicle—and a long commute for that matter—is the ability to explore new parts of our planet.

Exploring is important because it symbolizes that line between “work trip” and “vacation” in the best of ways. Exploring a new part of the country, for example, isn’t about leaving work behind and emails unattended while you unplug. It’s more so about taking work with you while seeing a new place.

Over the years we’ve built up an internal document at Authentic called the Playbook, and it outlines the differences between remote working, and off-the-grid time. Exploring would be an example of working while exploring: landing in a new city, getting to work the next morning, and exploring new spots while you work and over the weekend, for example. Maybe you’d even wrap it into a long weekend for more time in a new place.

In order to explore, though, we need to establish a few ground rules for ourselves, and for our company, so that everyone is comfortable with travel plans away from our typical location.

Preparation & Research

Let’s say I hear of an amazing spot on the west coast, only an hour or so from a major airport. I scan Airbnb for a few days and finally decide on making the trek. The plan is to fly in after work, drive to the rental by 10pm, and be up the next morning connected to my team from a new location.

This would be ideal if I made sure that the essentials were available long before booking the trip, preparing myself and my team for where I’ll be and for how long. But before taking off to any new destination, I always keep in mind a few major topics to check off the mental list before packing that trusty carry-on:


Relying on buses or other public transport is likely not the best move to get around a new place. You won’t know how well the local system operates, and thus could find yourself apologizing during your entire trip when you aren’t where you say you’ll be. Save the hassle and pop for a rental car, ensuring you can get to/from any destination quickly and without the reliance of someone else.

If a service like Uber or Lyft are readily available, that may work, too. Keep in mind those services, while handy here and there, get expensive if you use them a lot, or during peak hours when rates can skyrocket.

Fast Internet

It’s hard to believe in 2016 we’re still talking about Internet speeds that can maintain a connection to modern email apps, chat apps, and conferencing programs. But in certain areas of the country, this conundrum is painfully real.

Research the area’s Internet availability, and even dial up a couple of the coffee shops or co-working spaces you think you might find yourself. In addition, triple-check with your accommodations that the speeds are strong enough for the work you do.

In the past I’ve literally had the homeowner run a speedtest and post a screenshot so I know what they’re actually working with. Actually, that’s a must in my opinion.

Potentially the biggest crux in working while traveling is an Internet connection that flat out fails you. You’ll end up scrambling for plan B while having to apologize to your team. Being stressed while traveling, and even missing deadlines or meetings because of it, isn’t a situation you want.


Related to Internet availability, making sure your accommodations are comfortable is key. I once rented a single bedroom spot in Brooklyn, aiming to explore all things hipster in that area a couple years back, and realized I was on one of the most crowded corners in the city.

As I would try to sleep, I’d hear drunk bar-goers leaving their watering holes at 2am, screaming in protest about this or that, making it impossible to find rest.

To be fair, renting in a new city comes with some level of uncertainty, but with how detailed maps and online reviews are today, it would be rather easy to determine if your rental was in a “hot, active, young” neighborhood prone to Wednesday thru Saturday bar crawls.

Find where you think you want to be, then poke around. Ask a few questions, search the web, see who else has visited before, and find out what you can learn about those neighborhoods before signing on the dotted line.

One thing remains true for all travel I’ve partaken in over the last few years: cheap doesn’t mean you’re getting a deal. It probably means they’re getting a deal.

Travel Tools

The right mix of tools for your specific trips will be constantly evolving. In six months, this list may be entirely different, but these topics won’t change much.

You may recognize that my mind generally goes towards ways that money (and travel) can work for me, something that is evident in the last section of this article on travel hacking.

Travel Websites

When it comes to flights, I generally fly Southwest and United for travel hacking purposes. No matter what, though, I’ll always open new tabs and explore what deals may be there for the taking.

  • An old school favorite, Kayak gives me an instant pulse on what’s happening and where. It offers up to five other website’s to compare to, as well, which is great.
  • Google Flights came on scene not too terribly long ago, and this services provides a different way to find destinations: by dates, places, and personal interests. Give this a shot for a new way to explore.
  • If you want to get creative, Skiplagged is a way to find airfare that pulls search results that contain “hidden-city fares” as well as one-way or round-trip tickets that may go through your destination. In other words, it scans for inefficiencies and aims to pull a few deals for your specific trip.
  • A couple others to consider would be Airfarewatchdog and Skyscanner, if only for some last minute searches on cheap deals. I’ve had mixed results with these kinds of sites in the past, as well as the “cheap fare” alerts they fire off to my email. By the time the alert arrives, typically the deal is past. You may have better luck.

Hotels & Car Rentals

  • Sack up and signup for an account with a service like and reap the rewards when you get a free night. Sure, that might take a while, but you don’t have to do anything to get it for free, so why not?
  • When it comes to international travel, I’ll scan Hostelworld and for honest feedback about locations where I know my knowledge will be limited. Sometimes single rooms can afford similar accommodations (and even breakfast), giving you a better overall deal. Beware of loud patrons and the general vibe of many hostels around the world, though. This is one of those where you generally won’t know until you get there. That said, Internet is usually pretty strong in the hostel community.
  • A new concept on the scene we've been noticing these days involves a more nomadic approach to travel: co-living and co-working spaces. NomadPass is a great example of a company that offers unique places across the globe that have strong wifi and built-in communities. You may end up finding that this approach fits your travel style, and desire for community, a little more nicely.
  • I haven’t found too much magic surrounding car rental deals, other than checking website’s like Hotwire against a few of the top rental car companies’ websites at the same time. The rental car industry is pretty focused on the bottom line, so you might also try to find a promo code, or ask around about an industry code, offering savings of up to 20% off your total fee.

Airport Parking

Extended parking, midterm lots, long term parking... it’s all a game of math, right? Spend less time stressing about parking and more time figuring out what is the most economical.

The convenience of parking right next to the airport for an overnight trip is probably worth $20, but if my trip lasts ten days, no way! I’ll find other options.

Each airport is different, but figure out what companies service your city and then seek those coupon codes online. For example, The Parking Spot services Denver and often has coupons that cut the cost of parking down by a couple dollars a day. That adds up.

If my options are long term parking and drop off via city bus, versus cheaper long term parking with a nicer terminal drop-off experience, I’ll go with the latter. Do some sleuthing and find the best deal.

Luggage & Accessories

I’ll keep this section short and sweet, but the importance of a nice piece of luggage or backpack can’t be overstated. There’s nothing worse than struggling with a wobbly wheel, tangled headphones, or a cell phone that’s sitting at 2% when traveling.

Keeping your personal and business effects in order, too, is of the utmost importance. My motto when buffing up the travel arsenal is this: pay for comfort where it’s important to you, and keep it simple.

If you would travel 50% better with noise cancelling headphones, save up and get yourself a pair; then treat them like gold. If you need a carry-on that boasts a battery for charging your Instagram habit, invest in one that fits your style and charges your devices.

When it comes to organization, scan Amazon for cases, holders, and other organizers for your tech accessories and personal gadgets. Keep things organized and keep things simple to keep your “stuff stress” as low as possible.

Travel Hacking

At this point in time, many people likely know what travel hacking is. Or at the very least, a sense of what it means. But if you’re new to the concept, it goes something like this: “hacking” your way into free flights, hotels, and car rentals by redeeming points that you’ve earned in a rewards program or on a credit card.

A few years back I wrote a few extended posts on an introduction to travel hacking as well as a fall update on similar topics. The concepts noted are still relevant today, so you may find interest in those posts.

Doing a simple Google search on the topic will reveal thousands of posts on travel hacking, many of which could become of great resource for you in your endeavors.

Travel hacking has been the #1 way I’ve been able to get my money to work for me over the last handful of years. When I’m buying groceries, a new computer, or even a pizza, what’s my money doing for me? If it gets pulled off a debit card, the answer is likely, “nothing.”

When I realized that most legit credit card bonuses offered 25-50k points for $2-3k spending minimums in the first few months, a lightbulb clicked. You’re telling me I can figure out my near term travel goals, signup for an airline reward program or two, and bank points on things I’m already going to be purchasing? Yes!

Begin Here

I’m a big fan of Chris Guillebeau’s work over the years, and his Cards for Travel project was a great place for me to make educated decisions on my first travel hacking goal.

Once you get a better sense of your travel habits, and understand what travel hacking can do for you and your typical expenditures, this is the spot to check in with what’s being offered and when.

Travel (and Spending) Habits

If you have an issue with overspending, don’t open a credit card. If you already have bad credit, don’t open up a new account. If you’d be stretching your finances to hit a minimum spend target, revisit this at a later time.

If you are in a financial position to open and pay off a credit card each month, though, then defining your travel habits is the best next step.

By that I mean, where do you want to go? All over the United States? Maybe to Europe every year for a big trip? Different airlines—and airline alliances—offer different options.

Southwest Airlines is my airline for domestic travel, period. Their credit card offerings and companion pass program is hard to beat. And with flights that are already on the cheaper side, using their credit cards and banking points is a no brainer.

Because of their card offerings, United has become my current international airline. At times United can be downright abysmal, but if I’m not paying for the flight, somehow that stings a little less. With a myriad of options to earn bonus miles (and every day spending miles), points can rack up quickly.

Some credit cards allow you to transfer miles to multiple airlines, as well. For example, a credit card living underneath the Chase Ultimate Rewards program allows you to transfer to multiple airline partners depending on your travel needs.

In the end, knowing where you want to head, how often you want to head there, and (potentially) with whom, will determine the right direction for your own travel hacking plan.

Being Patient

Last but not least, it’s important to be patient when looking for travel hacks. Southwest’s offers for signing up vary from 25-50k bonus points, so be on the lookout for seasonal jumps, but don’t take the first offer you see.

Explore airlines’ reward charts, too, to get a sense for just how many miles/points you’ll need to take that trip or trips.

Using United as an example, I need 70k points for a round trip to Japan. If that’s my goal, I won’t immediately sign up for a card that is offering a minimum bonus. Rather, I’ll research what that card is known to offer and wait it out.

After all, there’s a huge difference between 25k and 40k+ points when they’re in the form of bonus points.

In Closing

Traveling as a remote employee is a privilege, and should never be taken for granted. With the right head on your shoulders, and tools at your disposal, even the most unfathomable of locations can be a reality with a little elbow grease, due diligence, and patience.

Truly living a Remote Life comes with heaps of opportunity, but also comes very real concerns and potential drawbacks. The trick for those of us in a remote working position is to lean into those difficulties, while taking the time to thoroughly enjoy the benefits that can come with such a lifestyle.

Working hard and playing hard; finding that delicate balance and firming up a personal ethos surrounding growth, fulfillment, happiness, and opportunity.

That’s what it’s all about, and you have those keys now, too.