“Excuse me, ma’am. I overheard your conversation just now. (Talking about the new season of Tiger King.) Are you a producer?”

“No, sir. I edited an article about some upcoming TV programs. I don’t work in film. I’m a freelance editor/copy writer. I work wherever the computer is.”

Even as I said it, I was thinking about the accuracy of that statement. Over the last two years, I’ve pulled out my computer and worked on editing and writing projects in six different states, in hotel rooms and coffee shops and an occasional gas station parking lot. I’ve worked at three different beaches and sat next to Plymouth Rock while ghostwriting an article about the electric grid. Today, when I was overheard talking about a project, I was working poolside in 65-degree weather.

This arrangement has a lot of positives. I can go anywhere as long as I can take my laptop. I can see new things, hang out in new climates, get plenty of vitamin D, explore new work environments, and even be overheard by complete strangers who might need a copyeditor. I am not bound by a 9-to-5 schedule or an office in a particular location. 

I have always known that I thrived in an unstructured environment but it took a long time, and several careers, to finally have the confidence to do this freelance thing for actual money, to invest in it and believe in it enough to make it a sustainable form of income. I love working from anywhere. It wasn’t easy to get here, it wasn’t always available to me, but I like taking advantage of my current circumstances to its fullest. 

There are, of course, a few drawbacks to the situation. Sometimes, it would be nice to travel and actually go on vacation. But at this stage of my business, I’m not comfortable taking a long time away from the computer. Instead, I’ve sat at the beach working while my family plays in the surf. I’ve taken meetings inside where it’s quiet and air conditioned while just out of the corner of my eye, the pool beckons. I get up on time, I keep a schedule, I make my deadlines. I don’t always get to take that leisurely walk every morning. And since I’m not a local, I don’t always know which coffee shop or park bench is for working and which are for other purposes until it’s too late. Sometimes the fear of being overheard keeps me self-sequestered in a dark hotel room. 

So right now, working on the road is a work in progress. But I’m starting to figure it out. I keep my morning and exercise routines just as if I were home. I attend virtual meetings, I open my agenda, and I block schedule time. I have also started setting boundaries for myself, trusting I have the time to meet my deadlines and still have time to explore wherever I’m staying. When it’s financially feasible, I like to extend a trip to include the weekend to fit in an adventure. I also try to take a break in the afternoon to walk around or check out the local scene and then get back to work in the evening when I’m stuck back at the hotel, because there is nothing glamorous about hotel living. At least not on my budget. 

I’ve learned a lot from meeting other people who work while they travel. My spouse travels for work (and lets me tag along). But I know more and more people who are working, like me, from the road, some living permanently in RVs and traveling where the wind and the weather calls. If you have any tips or strategies for working from the road that are working for you, I would love to hear them.

Oh! And the strangers at the pool this morning, as it turns out, 17 years ago, we lived just a few miles apart and today we spent a good half an hour rehashing all the hurricanes of 2004. 

Cheers.