What you Need to Know about Working from the Road

woman wearing a hat in the field travel

A year and a half ago, I seized the opportunity to travel and write for a living. It wasn’t a glamorous life, but I was doing two things I loved and that was more than I could ask for.

As time closed in on the start of my adventure, I pictured myself sitting on a beach, sipping on drinks with fruity straws, and enjoying the sunshine with a laptop perched on my lap.

While a great deal of my freelance career over the past ten years did take place on beaches, in airports, and on park benches, it wasn’t always as glamourous as it sounds. I had my fair share of struggles – still do.

No one bothered to prepare me for that reality. So as many of you ring in the New Year with freelance goals, be warned. Here are some of the struggles you’ll face while working from the road.

WiFi Connection

Many people who work from home or on the road will tell you that as long as they have an internet connection, they have nothing to worry about. They can work from anywhere at any time. This sounds easy enough until you try it.

Especially when crossing international lines, or making stops in rural areas, the WiFi force will not always be with you. August 2015, one trip to Pennsylvania robbed me of internet for a week.

Back then, it wasn’t as big a deal. I had taken the week off – my last real vacation in 18 months – but that didn’t make the loss any less felt.

Be prepared for periods where you might be without internet, even from your phone. If there are clients who keep you on-call, let them know when you venture into areas where conection may be a problem.


Some people work best with distractions. The more people conversing around them, the busier the streets, the noisier the cars, the better they tune into their own thoughts and their work.

I don’t know about you, but I’m not one of those people. I can work with some distractions, but generally speaking, I need peace and quiet to be productive.

Distractions may also come in the form of temptation to do something other than work. This is especially tempting when traveling because you’ll likely not see those places or people, or have these opportunities for some time to come.

Good luck saying no.

Balancing Act

If like my trip to Myrtle Beach, you are actually on vacation, working on the road can cut into your fun-time. While on the trip, I still had budgets to look at, logos to design, blog posts to finish up, and admin work to do.

If you decide to stay in and work, the reality is that you miss out on those aforementioned temptations that are actually a great way to spend your time.

I usually try to do my work when everyone’s sleeping. That way, when they’re awake and throwing temptation my way, I’m already on top of my work. This does mean sacrificing some sleep, but the trip won’t last forever anyway. You can catch up later.


Are you one of those people who decide how much longer you’ll be out, based on the percentage left of your battery? I’ve been doing that for years, way before the smart phone craze.

I figured if anything should happen, I need my phone to make emergency calls. If it’s dead, I’m dead, so might as well go home.

If we have this much trouble keeping our phones charged for personal use, imagine when your phone also doubles as a tool for work. And imagine keeping tablets and laptops charged for the road as well. Most car chargers are terrible, and could actually damage your device or its battery over time.

I work around this by bringing all my gadgets and keeping them fully charged, but off until I use them. When I get to a location where I can plug in, I charge up even if I barely used the battery.

In Motion

Remember when I said I often envisioned myself tippy-tapping away at the keyboard in airports? I should have also added planes and cars.

I’ve had to do this on several occasions when clients call me at the last minute to send off a file or send an update, and I don’t have the material on my phone.

But is it comfortable? Hell no.

If you’re planning on writing a novel or a few blog posts during a 20-hour drive, think again. Staring at a screen may also make you nauseous half an hour in. Good luck with the remaining 19 and a half hours after that…

In spite of all this, I still work from the road on occasion. In my line of work, there’s simply no avoiding that. And I’ve been doing this for so long that dealing with the shortcomings of working on the road is almost second nature.

However, these days I do most of my work from the comfort of a desk and with as few distractions as possible. This not only helps me knock out projects in record time, but with fewer errors, and therefore happier clients.

What are some of the struggles you face when working on the road? Tell me all about it in the comments below.

38 thoughts on “What you Need to Know about Working from the Road

  1. public libraries are my internet friends in the US, coffee shops elsewhere. Though I blog for pleasure, I know how difficult keeping everything charged can be on the road. Back to that in July.

  2. Great post thanks. We are not always aware of the challenges, traveling and writing for a living does look so glamorous.

  3. I empathise wholy with what you describe. During our long summer holidays (8 weeks at a time), I often get tempted to post my blogs, but wifi is so unreliable, I prefer to wait until I get home in September. Hopefully, new technology will conquer all these troubles.

    1. What you can do is write and schedule posts ahead of time. I do that every month to ensure I have a cushion of posts to fall back on. This post, for instance, was written maybe 2/3 weeks ago.

      However actual client work that comes up on the road is a lot more tricky.

      1. That is a good idea, but it depends on what you are writing about. I keep a book diary, which I write by hand about once a week, about the places we’ve been to and any notable events. Sometimes I type them while still travelling, but uploading pictures on the actual blog takes far too long.

      2. As long as you’re not writing about time sensitive things like seasonal posts or reporting the news, it really doesn’t matter when you publish. Even my Christmas post was written 3 weeks prior. But whatever works for you! 🙂

  4. I believe you love the travel. I did not feel any pain in your words. LOL. Being able to travel and work on the road some of the time beats sitting in a cubicle all of the time. I do understand your point. Be prepared for the pitfalls. It is not a matter of if they come. It’s a matter of when they come.

    1. Hi Tony! You’re right. I do love the travel! Shhhhh don’t let my clients hear us hahaha. I work away from the office a few days every week. I manage 🙂 But it was really tough in the beginning for sure..

  5. So much for the glamorous life of the itinerant writer! Glad to hear about the reality, in case I ever decide to leave my comfy home office.

Chat to me nuh!

This site uses Akismet to reduce spam. Learn how your comment data is processed.