I turned a layover into a working vacation during COVID. Here's what to know if you've been thinking of taking your remote work on the road.

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A promenade along the ocean in Cape Town
Credit: Armand Burger/Getty Images

When I tell my therapist about my latest issue, I'll call it an identity crisis. He's 9,000 miles away, but I can picture him perfectly. He'll shift forward in his chair, scribble something in his black Moleskin, and ask me to elaborate. I'll tell him to sit back. This is going to take a while.

When I landed in Cape Town I was a pilgrim, just passing through after a business trip in Botswana. Since there are no direct flights from Botswana to the U.S., I had a short layover in South Africa. However, after a quick check of the weather back home, it wasn't long before I transitioned from pilgrim to tourist. It was dumping snow (enough to build a snowman and his entire family tree) in Montana. I wouldn't have to pay a change fee to delay the last leg of my trip. Why not see some of warm and sunny Cape Town while I was already here?

Katie Jackson WFH view in Cape Town
Credit: Courtesy of Katie Jackson

The first thing I did  was hike up Lion's Head. The setting sun provided theatrical lighting for my first panoramic views of The Mother City. To my left, paragliders launched themselves from Signal Hill. Instead of advertising businesses, their sails read, "This is Living" in giant block letters. To my right, Table Mountain — Cape Town's most iconic feature — dwarfed the skyscrapers below. A local hiking with me pointed at what appeared to be the tallest buildings on the horizon. "We call them the tampon towers," he said. I failed to stifle a laugh. They did look like tampons. Still, the city's most controversial building is the stadium constructed for the 2010 FIFA World Cup. It's either a masterpiece or a monstrosity, depending on who you ask.

I checked a lot of Cape Town boxes in just a few days. I saw the penguins at Boulder Beach, surfed Muizenberg, people watched from Café Caprice, toured The Robben Island Museum, got a massage at The Twelve Apostles Hotel and Spa, and even cycled Chapman's Peak. Despite the pandemic, everything in Cape Town seemed open. Plus, the weather was great. Not even the idea of cage diving with great whites unsettled me as much as the idea of returning home to Montana's never-ending winter. Why couldn't I stay in Cape Town for another week? Like millions of other Americans, I was working from home anyway.

No group has grown more in the past year than the work-from-home crowd. According to a Pew Research poll, the number of Americans working from home has tripled from 20 percent to more than 70 percent. For employees whose offices have closed, working from home is the only option. Or is it? I started noticing hotels target guests who can work remotely a few months ago. But it wasn't until my layover in Cape Town that I took the bait.  

I don't remember the exact moment I traded my Cape Town tourist hat for my remote worker hat. However, I know it was at The President Hotel. I didn't choose the property for its history (more than 250 years worth, if you count the days it was The Queen's Hotel) or the fact it was reopened by the late Nelson Mandela. Initially, I chose it for its location. It's just a few blocks from the beach in trendy Bantry Bay. I extended my stay once I learned about its "Work from Hotel" package (starting at $900/month). 

This new package — offered in partnership with Cape Town Tourism — is more than a play on words. It's a lifestyle. After two weeks of leading it I already feel like Eloise. The only difference between me and the lucky little girl who called The Plaza Hotel home is the fact that I have to work. Fortunately, the hotel makes it easy. I have an espresso machine in my room and unlimited coffee. I have a landline, a real desk, Chromecast with Google TV, and keyless Bluetooth door entry. Then there's the uncapped free Wi-Fi. It's so fast I never have anxiety about scheduling Zoom meetings. I also have access to a conference room and business center. At home I have to drive to Staples if I need to copy, print, or scan.  

Katie Jackson WFH at a bar in Cape Town
Credit: Courtesy of Katie Jackson

At home I also spend my work breaks catching up on cleaning. Here there's a diligent housekeeper who makes my bed, launders my linens, and empties the trash. As a result, I spend my breaks at the hotel's pool, spa, and fitness center. After 5 p.m. I can usually be found in The Senate Bar. It has a stiff gin and tonic on tap. I can't tell if I'm proud of my happy hour perfect attendance record or if I'm embarrassed I can't pass up a cocktail BOGO.

I do have self-control, however, when it comes to the hotel's buffet breakfast and 24/7 room service. I don't take advantage of either because Cape Town is famous for its independent food scene. The only restaurant chain I recognize here is KFC. I avoid it at all costs, even crossing the street if I have to. It's silly (OK, irrational), but I'm afraid of running into an American I know who has expectations of me. In the U.S. I'm a homeowner, church-goer, dog mom, neighbor, aunt, and countless other titles not attached to my name in Cape Town. Here I'm just a remote worker taking advantage of a hotel package designed for digital nomads.

Or am I? The longer I stay here the more I revert back to being a tourist. I can't help it. The Work from Hotel package comes with an iVenture card granting me free entry into major attractions, and the city is bursting at the seams with cool things to do. Doing them all justice would require living here. However, I can't live in Cape Town. My life is in Montana. So basically I'm a pilgrim. Or am I? I'm not here for religious reasons; I'm working remotely. 

I'm not 100 percent sure what my therapist will say next week when I tell him I'm not sure if I'm a pilgrim, a tourist, or a remote worker. But I think he'll find my identity crisis amusing — a first world problem I'm #blessed to have. He'll probably say I'm not the only one with this "problem," especially as the world starts to re-open to Americans. Most importantly, I think he'll tell me it's OK to be all three.