How We Make a Living While Riding Motorcycles Around the World

Remote Work and Managing a Business from the Road

We – Jess and Greg – are the founders of  RUFFLY, which makes artisan outdoor dog gear and the K9 Moto Cockpit motorcycle dog carrier.

We manage and market RUFFLY while traveling around the world by motorcycle.

The purpose of this GORUFFLY journey is to put our dog gear to the ultimate test – and to raise $100K for Girl Up.

It’s a thrilling and unconventional lifestyle and remote work schedule that we absolutely love – but it’s also really hard to pull off!

Business Owners and Brand Ambassadors

To juggle our competing roles as the owners and the primary brand ambassadors for RUFFLY, we travel four days each week and then we stop to work from and AirBnB the other three days of the week.

This work-travel balance is the key to being effective in both roles, avoiding burnout, and always doing it with love and joy.

Four days traveling…

During the four days of travel, we spend as much time as possible off-road and beyond cell coverage, preferring to wild camp, picnic, and bathe in rivers.

This ‘travel’ part of the journey includes getting lost, facing challenging roads, overcoming breakdowns, and otherwise emmersing ourselves in the aventure of a lifetime. It also involves continually documenting and sharing the journey through photos, stories, and videos.

Much of these days is spent dirty, dusty, and with only a tent flap separating us from nature. It’s where we love to be and, by the end, we’re looking forward to being back in the ‘office’ for a few days.

Three days working remotely…

When we ride back into cell coverage, the social media notifications, reminders, customer emails, and WhatsApp messages from our RUFFLY team explode onto the smartphone screen.

It might not be everyone’s dream to respond to customer emails and coordinate order shipments from the side of a dusty road or a mosquito-infested wild campsite, but we love it!

It’s made possible in part with an international eSIM that covers us in each and every country, providing a fast local data connection wherever the signal reaches. These days, traveling without cell connection is a huge inconvenience while traveling – but it’s a total dealbreaker if you’re also trying to run a business!

At the end of the four travel days, we check into a pet friendly hotel or AirBnB to work for the other three days of the week.

This an opportunity for a comfortable bed, a hot shower, maybe some air conditioning, and the chance to do a load of laundry.

But this is not rest time.

We condense an ordinary five workdays (really seven workdays) into just three. That means we need to be ultra-productive with the little time we have.

It’s a wonderful and grueling schedule but we love it. The travel brings us joy while growing RUFFLY gives profound meaning.

Joy and meaning – isn’t that the purpose?

Resources, Technology, and Effective Practices for Remote Work

We adjust the four-days traveling and three-days working schedule when have more work to catch up on or when a travel stretch takes longer than expected. But that schedule is one of the key ingredients to our remote work success on GORUFFLY Around the World.

We discovered this schedule and the other resources, technologies, and practices that we use by repeatedly testing them out over a couple years. Our first travel and remote work trips lasted a week or two, then several, then over a month.

We’re always testing, learning, and adjusting as we go but there are some important lessons that are critical to our success.

Remote work resources…

Reading articles and videos like this one are a great way to get started. Most remote working travelers have RVs or vans, not motorcycles, which means they can pack a whole lot more equipment, technology, and luxury items than we can.

This is important because, to a certain extent, the more comfort you have, the more effective and productive you can be wherever you are. For example, it’s quite hard to get thoughtful work done semi-prone in a tent during a rainstorm compared to sitting at a proper table inside an air-conditioned camper van!

That’s why staying in a modestly comfortable hotel or AirBnB with strong WiFi is essential for us. We’ve worked from campgrounds, RV parks, and hostels. So it is possible, but it’s far from effective and productive.

What about Couch Surfing, Bunk-a-Biker, and other shared accommodations? These can be wonderful ways to meet locals and share meaningful interactions, but they are not good options for getting work done.

Even if you’re not an introvert like we are, you need to be 110% focused and free from distractions to squeeze a five-day work week (seven-day work week if you own a business) into just three days.

On the other hand, even if we could lock ourselves away in a bedroom and ignore our host for a 12-hour work day, what kind of person does that? The generous individual is hosting us to enjoy our company and share in the adventure, not to be the ‘supporting cast and crew’ in our story!

Remote work technology…

We use pretty much all the same technology that we did before transitioning to remote work, only now it’s smaller.

We use project management app to help manage our team remotely, assign tacks, share content and feedback, and ensure accountability.

A cloud storage and collaboration tool is essential. Dropbox, Google Drive, and iCloud are good examples and we use each of these and more because every vender, collaborator, and partner has a different preference in how they share content. The important point is that nothing should exist solely on a physical drive or laptop that can be lost, damaged, or stolen.

And yet, when you produce hours of 4K footage each week, you face two huge obstacles:

1. What cloud storage provide offers terabytes of storage for a reasonable price?
2. How fast does the WiFi need to be to upload that much data in just a few days?

We haven’t found a cost-effective solution to this problem and so we carry numerous physical drives for content storage and backup. Importantly, we only use solid state drives since they are much more durable – although also much more expensive too.

WhatsApp is the go-to messaging tool in Guatemala so that’s what we use for daily communication with our RUFFLY team, artisans, tailors, vendors, and suppliers.

There are other options but we go with what’s easiest for everyone and it works fine. Just make sure you have a proper collaboration app like Write or Slack for assigning tasks and follow up. Otherwise, it’s easy to miss an important message or to-do when you come ride back into cell coverage and get bombarded by 150 messages all at once!

What once might have seemed like a luxury or frivolity, a tablet is an important part of our remote work kit. The iPad is an excellent tool for performing small work tasks at the campsite or during rest stops. When we stop for our three-day work periods, the iPad serves as a second monitor for video, photo, and website editing.

If you maintain a website, many website builders allow you to format your site for users on tablets. That means you need a tablet to be sure it looks the way it’s supposed to.

Oh yeah, and if you enjoy watching an episode of 1883, Walking Dead, or Severance in the tent before bed, an iPad is a great way to save your laptop battery!

Remote work practices…

Our four days traveling and three days working is the big ‘practice’ and key ingredient to our special sauce. But we’re not a one-trick poney either!

Working at a café

Working in a café is never a substitute for a quiet comfortable AirBnB or a hotel room where you don’t have to ask someone to watch your laptop when you go to the bathroom.

If you’re traveling with a dog, working from a café is even less productive. Although Whimsy is generally exhausted and catching up on sleep during non-travel days, she is naturally hyper alert and gets cranky when tired and overstimulated.

So, by all means enjoy a café for a couple hours while you respond to emails or social comments, but don’t plan to edit video footage or manage your distributed team while glasses clink, people gab, and the espresso machine blares in the background.

Meetings and brainstorming

We avoid holding video meetings at cafés. Nobody wants to listen to it and nobody appreciates the spectacle. More importantly, it’s hard to show your non-traveling team the focus, attention, and respect they deserve when the server is delivering your triple cream chai latte and vegan spinach wrap at a beachside café while tanned surfers walk past.

Just like team meetings, brainstorming and strategizing are important parts of ‘remote work’. But they don’t always have to be done in the quiet and comfort of the AirBnB home office. We save the heavy stuff like discussions about finance and HR issues for ‘at home’ but for everything else we brainstorm as we travel.

On easy off-road and tarmac, we strategize about marketing, sales, etc. over our helmet communicators. Often an effective brainstorming session occurs as we sip whiskey at the campsite and watch the sun go down. Then during workdays, we discuss pressing topics while stretching our legs and giving Whimsy her morning, noon, and evening walks.

Evenings, transitions, and extended stays

Whenever possible, we give ourselves time in the evenings to decompress and binge a TV show in the comfort of our hotel room. Days off and afternoon naps are rarely a luxury we can indulge but a few hours in the evening are golden moments for checking out.

The hardest moments can be transitioning between work and travel. For example, if we arrive late to the AirBnB where we will be working for the next three days, we are likely to feel sluggish the next morning and lose valuable time doing chores.

But if we arrive in the afternoon, we have an extra few productive hours to air out gear, wash clothes (and ourselves), set up our workstations, and decompress from the hard traveling. The improvement in our productivity the next day is enormous.

Lastly, we don’t leave our packing to the morning of our departure because we are already leaving the AirBnB already stressed and exhausted with loads of unfinished work to do. We don’t do it late the night before either because we’ll wake up tired, run down, and cranky. Instead, we organize, repair, and repack our gear as a break during the workdays.

Remote Work While Traveling: It’s Not for Everyone

Definitely not.

It’s difficult, often uncomfortable, and most jobs can’t be done remotely anyway. If you’re fortunate like us to have a business, skill set, or employer that allows for remote work while traveling, don’t leap into it too quickly.

Try it for short stretches and don’t go all-in until you’re sure it’s right for you. We hope you’ve found these tips and insights from our experience helpful and maybe even inspiring.

If you’re considering if and how to try remote work while traveling, feel free to reach out to us with any questions!

Check out the other gear that helps us GoRUFFLY Around the World