What’s it really like to work from anywhere? 


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A year ago, no one dreamed how dramatically our work lives would change.

Actually, some of us dreamed about it, but that’s the extent of it. Never in a million years did we imagine that we’d be freed from being in the office every day. That we could work from anywhere we wanted.

Professionals with wanderlust are still rubbing their eyes when they see offers like Expedia’s latest promotion. The travel company offered a limited number of two-week “Work from Here” trips for just $20.20. Those who snagged one of the promotional deals got a two-week stay for two at an Expedia VIP Access Property in Charleston, South Carolina, Key West, Florida, or Arizona. 

The promotion, targeted at professionals who had the flexibility to pack up their laptops and work anywhere, focused on those who wanted to work somewhere different. Those who wanted to escape. 

An aerial view of Key West, Florida.

“Built on the wanderer mindset of today’s work-from-anywhere professionals,” said Nisreene Atassi, Senior Director, Communications, at Expedia, “’Work From Here’ celebrates a new global culture that allows employees the freedom to balance work with travel. When we can travel freely again, we want to inspire workers to think differently about their workspace to create happier, more productive experiences, which would benefit not only employees but also employers.”

Expedia is not the only company pushing this new work paradigm. Many companies are now encouraging their employees to work from anywhere. 

Reddit, for instance, recently joined the rank of companies like Facebook, Twitter, and REI (which recently sold its Seattle HQ building to Facebook), all of which allow their employees to work remotely. Other companies doing the same include Zillow, Square, Shopify, Slack, Upwork, and Coinbase.

It’s hard to imagine that employees freed from sitting in a cubicle from 8:00 to 5:00 would work from home every day—especially young professionals. It’s much easier to imagine some following in the footsteps of digital nomads, such as freelancers. 

But what’s it really like to work from anywhere?

New York Times running columnist Jen A. Miller knows. In 2017, at age 36, the freelance writer, who also wrote for the Michael J. Fox Foundation and various healthcare systems, stuffed her laptop into a lavender REI backpack and hit the road in her Jeep Wrangler. 

She was somewhat following in her grandparents’ footsteps.

My grandfather, who fought in the Pacific campaign in World War II, said he’d never leave the country again until he saw all 50 states,” she says. “They were in their late 60s then. His exception was that they could drive through Canada to get to Alaska. They didn’t get to all 50 states, though they saw a lot. So that’s what I decided to do.

Her own epic four-month adventure took her to 18 states, including Idaho where she surprised herself by adopting a small cattle dog mix she named Annie Oakley Tater Tot. 

And she kept up with her freelance writing jobs along the way

While it was a great adventure, she said there were definitely challenges.

“It’s not as easy as just picking up your laptop and moving somewhere else,” she says. “Even if you’re in a nice hotel, there are other people in the hotel, and there’s housekeeping. There were cases when the hotel WiFi was down, and the person at the front desk didn’t know how to fix it so I’d have to go somewhere else.”

She didn’t have a mobile hotspot, which would have made some of that easier. 

On her road trip, she frequently drove long distances, which made working harder than expected. “I’d say give yourself more time than you need to set everything up and have a backup plan in case it doesn’t work. This romantic idea of, I’m just going to hopscotch around the country and work in the same capacity, is just not possible, especially when you get into the more rural areas. Could you do a whole workday at McDonald’s? I don’t think so.”

She sometimes struggled with scheduling interviews, knowing she might be in a different time zone by the time they spoke. She interviewed a doctor from her car in the pouring rain. 

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But she also found great joy.

“I finished writing one story on a picnic table at the Indiana Dunes State Park and edited a New York Times Metro section article in the Las Vegas airport.” She flew to Hawaii and saw volcanoes. She dog sat for a friend in Maui and visited other old friends she hadn’t seen in years.

She says it’s probably much easier for a full-time employee to travel and work. “They get to the next spot, and once they’re there, they can just do their work. They don’t have to worry about the freelance business aspect of it. They’re not pitching work or having to schedule interviews. They get paid no matter how their day goes.”

She points out that data security can be an issue. “If you work in a regulated industry, especially banking and finance, you need to talk to your IT team and make sure all your stuff is secure.”

She’s glad she made the trip, despite the challenges of freelancing on-the-go. Would she do it again? She already has. 

And once Miller has been vaccinated for COVID-19, she plans to embark on yet another big road trip.

“I’ll take a couple of months and drive from New Jersey to California,” she says. “I’d like to drive the Pacific Coast Highway, and I want to go to San Diego and go to surfing school.”

Originally published Jan 26, 2021, updated Jan 27, 2021

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