From Hotels to RV Camping to Yurts, A New Spin on the “Working Vacation”

It’s a magnificent Sunday afternoon on the banks of Florida’s Myakka River. I’m perched at a picnic table, cigar burning, Keller Williams streaming his stuff on the Bluetooth speaker. The sky is powder blue, a breeze is blowing. No place could be finer…

… to open my laptop and draft some words for some paying clients.

I’d wager some people’s opinions just went from “very cool” to “Dude, close that damn laptop and be present!”

It’s been said “work is a thing, not a place.” That’s never been more true than during the Covid-19 pandemic. Today’s workplace includes US and international destinations that offer a single common attribute – reliable Internet – used by people who share a common believe – I can work and travel and not miss a beat.

The thing is, working while on vacation is nothing new. We wrote about it months – even years – ago. We’ve done it from campgrounds along the East Coast to hotels along Route 66 to cruise ships deep in the Caribbean. With a laptop and Internet, work just gets done. Now, digital nomads and their progressive employers and clients believe home officing and vacationing while working, or “telecommuting work tourism” will be the standard for the future.

This situation has been the reality for countless remote and mobile workers amid the pandemic. It’s nothing new. National Geographic reported that the audience of freelancers, entrepreneurs, and the self-employed that have made up the majority of the “digital nomad” crowd are being joined by traditional office workers untethered from the corporate hive – and clock. A survey of company execs revealed that 82% expect to offer remote work at least part of the time after the pandemic.

That includes working while on vacation. Bali, Barbados, Chang Mai, Mexico City and Estonia have always been popular holiday destinations. Now they’re hot for “working vacations,” even a spin on staycations. Some are offering coworking spaces with desks, high-speed wifi, the amenities you’ll find back in the corporate office – even working tourism visas.

“It’s not a lifestyle for everyone — you have to know that upfront,” Scott Eddy, a full-time traveler and the host of Lifetime’s Video Globetrotter series, told Travel & Leisure. “But there’s tremendous upside, if you can get it right.”

There’s a lotta truth packed in that, and getting it right doesn’t happen by accident. Along with their laptops and any other requisite devices, traveling workers need to pack the understanding of their employers, teams – and themselves – for remote work excursions.

Airbnb has some compelling stats on this Covid-created work-and-travel reality, including figures that show trips of two weeks or more were increasingly common when travel returned following the pandemic shutdown.

So if you’re heading out, forget the excuses should issues arise. Avoid complications by planning ahead. A few tips…

Pack well. If you plan to vacation during what for others are work days, there’s no excuse for absentmindedness. Forgetting your charger or a file or another must-have item without which you’ll be a stranded nomad is inexcusible. Need a list to make sure this doesn’t happen? Then make a list. If you’re a veteran traveler, you’re probably habitual about packing your laptop and chargers in specific pockets, or uploading files to the cloud. These habits will save you once the  home) office door closes and you head out for an extended getaway. Packing well also means…

Dress the part.  Have a Zoom scheduled with well-dressed folk? Your t-shirt or other travel garb might not fly. I had a call set up and realized once at the campsite that I forgot a respectable shirt. Coulda been a golf shirt or a long-sleeve polo, but my muscle and concert tees weren’t going to cut it. So I made a quick trip to the local Walmart (luckily about 5.2 miles down the road), hit the clearance rack in the men’s department, and found a totally acceptable collared shirt – for six bucks. Prolly spent more on gas than for the shirt. Not only was it a perfect fit for the call, it will now have a permanent place in the camper. Not taking that chance again.

Block your schedule. I’m writing on the first Sunday of 10 days on the river’s banks. Tomorrow, I have two calls scheduled, and a Zoom call later this week. I’ll be working, and scheduling time for myself and our vacation.

Will your connections be reliable? It’s hard to justify a missed Zoom call because “my beachfront Airbnb yurt has lousy Internet.” On our current trip, I needed Internet just for emails and document downloads. Two friends who were joining us needed Internet – one for emails, the other for Zoom calls. Without bandwidth, the Zoome would be sunk. Ask your destination – a campground, hotel, or other location – whether they have reliable wifi. Better yet, search for reviews. If others have been there, they’ve likely posted their comments.

Time shift. If your destination is one or 12 time zones from the main office, are you ready to pivot? For example, are you up for a call at noon NYC time when it’s midnight at your getaway in Thailand? Can you collaborate seamlessly with your team when you’re who knows where? You won’t find RVers in a yurt or Bali. But as a camper, RVing has proven to be the great escape. Wake early, work late, grab a perch with a view. As long as your Internet is reliable, weave work where it fits into your agenda.

Clue in your people. Thirty years into my career, we travel more than ever. My clients have come to expect this. They know I travel, but they also know I won’t shirk responsibilities and go AWOL – leaving them in the lurch. I have to be on it. As a career freelancer, if I don’t work, I don’t get paid. So work doesn’t just get woven in. It’s part of the whole cloth of my existence. If I want to pay my mortgage, I deliver my product. My travel companions also know I’ll need to trade some work time if we want to hike or paddle that park later. If there’s conflict, the keys to the F150 are hanging by the RV’s front door. No problem. Have at it. Just be sure to…

Temper their expectations. Make yourself too available and clients may call – repeatedly – with “just one or thing.” One more thing can cascade into two, four, eight… You get the drift. Balance is a personal decision; how much are you willing – or unwilling – to make their schedule your schedule? If you left a project open and it needs your hand, lending that hand might be inescapable. But if it’s stuff that could wait, I remember a line from my dry cleaner: “What makes your crisis my emergency?” Balance how much you’re willing to bend and toe that line.

Most importantly, lose the guilt. If you’re responsible, you can seamlessly blend fun and work, making time for both downtime and deadlines. This way, you can be present – even thousands of miles from that place formerly called work.