Lessons from the road: the dos and don’ts of freelancing on the go

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One of the biggest benefits of freelancing is the freedom to set your own schedule and travel without the constraints of vacation days. While that freedom is something that draws people to freelancing, it also comes with challenges.

I recently put the “work from anywhere” theory to the test on a 4-week RV trip. If you’re considering freelancing from the road, read through these do’s and don’ts to learn from my experience.

The plan

First, let me paint a picture of our trip so you have an idea of what I signed myself (and my husband and toddler) up for. We covered 5,100 miles in 4 weeks and traveled in our pickup truck, towing a 21-foot travel trailer.

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We traveled through 7 states, slept in 6 RV parks, 3 campgrounds, 2 Walmart parking lots, 1 truck stop, and 1 friend’s driveway. All while keeping up with my full workload and client needs.

Freelancing while traveling always has challenges, but traveling by RV has its own unique set of obstacles. Without further ado, here are the do’s and don’ts of freelancing from the road.

Do’s

Do get as much work done ahead of time as possible: As a freelance marketing consultant, that meant scheduling email campaigns and a lot of social media content before our trip (my favorite scheduling tool is Buffer).

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Do give your clients a heads up: Share your travel plans with clients, but take it one step further by also sharing your strategy for keeping up with their projects and meeting upcoming deadlines.

They will appreciate your proactive approach, and will understand if you are a bit less responsive at times during your trip. My clients were excited for our trip, and even followed along with our adventures on Instagram.  

Do make sure you have an unlimited data plan: Even if you stay at an RV park with wifi, it may not be very reliable. I often found myself using my hotspot rather than the RV park wifi, which uses a lot of data.

Do maximize every hour of the day: Make the most out of every chance you have to get work in. For me, this meant waking up earlier than my husband and son some days so I could get a couple hours of work in before we started our day.

Do take the weekends off: As a freelancer, I could work 24/7 if I wanted to. While traveling I made sure to truly take the weekends off, unplug and enjoy the time with my family and exploring new places.

Over the years, I have let go of some of the pressures to always be available. My clients don’t expect me to work on the weekends, so I shouldn’t expect that of myself, either.

Do research cool local coffee shops: Spending a few hours working in a local coffee shop kills two birds with one stone—you’ll get to experience the city like locals do, plus you’ll get some solid work done.

If you are traveling to bigger cities, you can also research coworking spaces like wework.

Don’ts

Don’t depend on the RV park wifi: This is one of the biggest challenges when working from the road as opposed to staying in hotels or vacation rentals.

Always try to book a place that has wifi, but don’t rely on it. Wifi is a relatively new amenity RV parks are offering guests, and should be looked at as a perk, but not a necessity. See the point above about having an unlimited data plan.

Don’t expect to be able to work the same hours you normally do: No matter how well you research and plan, things will come up and you will need to be flexible with when, and where you work.

Plus, the point of traveling is to experience new places and you can’t do that from behind your computer.

Don’t stress too much: If you follow the Do’s outlined above, you’ll be in pretty good shape.

Take the time to enjoy your travels, where you are, and remember that the experience and time away will be better for your business in the long run. You’ll come back refreshed, motivated and more creative than ever.

Don’t forget about working in the car: On travel days, I would work in the car while my husband drove. If I had good service, I would connect my computer to my hotspot and work without feeling like I was missing out on exploring our destinations.

I love the freedom of freelancing. I love being able to dictate the way my hours are spent, and have the freedom to travel. I also love what I do, and keeping my clients happy.

It is possible to freelance from the road—it just takes research, planning, and flexibility. If you find yourself freelancing from the road, I hope these do’s and don’ts help you.

Take the time to enjoy your surroundings, experience new places and people. Ultimately, you will be inspired and your work will reflect that.  

Do you work while traveling? Please share your experiences in the comments.

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About Amanda Holliday

Amanda Holliday is the founder of 2L’s Marketing, a full-service marketing consulting firm. She received her Bachelors degree in Business Administration and Marketing from The University of Colorado at Boulder. Amanda worked with a wide variety of clients at digital and traditional agencies before starting 2L’s in 2011. Amanda now lives, works, and plays in Whitefish, Montana with her husband and young son, where she continues to serve clients nationwide.

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