Industry Trends

Permanent Workation Isn’t All It’s Cracked Up to Be

Caleb Newquist Editor-at-Large, Gusto 
remote work

Programming note

On the Margins will be off next week but will return on December 3. Until then, stay healthy, my friends.

The workations you deserve

The pandemic has had more than its share of annoying trends: Tiger King, nouveau sourdough bread bakers, celebrity quarantine Instagram posts, quarantine productivity, quarantine productivity backlash, Zoom, Zoom happy hours, Zoom dating, Zoom weddings, Zoom divorces, Zoom family reunions, Zoom election watch parties, Zoom holidays, “the new normal,” “we’re all in this together,” “these trying times,” toilet paper shortages, noses poking over the top of masks, to name a few.

But for my money, there hasn’t been anything quite as insufferable as the small but mighty segment of digital nomads that struck out to work anywhere and everywhere during the pandemic. Unencumbered by anything meaningful in their lives, these privileged laptop hobos were going to hop from exotic place to exotic place and still work 10 to 12 hours a day until the plague ran out.

Fortunately, according to this fantastic article from Erin Griffith, we learn that many are trying and failing to live that dream:

Americans have never been especially good at vacation. Before Covid-19, they were leaving unused hundreds of millions of paid days off. They even created a work-vacation hybrid — the workation. The idea: Travel to a nice place, work during the day and then, in theory, enjoy the scenery in the off hours. In pandemic times, the digital nomads have simply made workation a permanent state.

The bad news is it’s the worst of both worlds. They should be enjoying themselves in their new, beautiful surroundings. But they can’t enjoy themselves, because work beckons. The anxious self-optimization pingpongs between “Why aren’t I living my best life?” and “Why aren’t I killing it at work?”

Ahh, yes. Living the best life and killing it at work. The dual holy grails of the modern American hustle junky. Honestly, I can’t think of many things that are as counterintuitive and pointless as working when you’re supposed to be on vacation. And yet more than a few people thought they could transform this paradox into a lifestyle. It’s truly the firstiest of first world problems. It’s the foolishest of fool’s errands. I suppose it’s naive to think that even a paradigm-shifting event like a pandemic could realign our warped relationship with work.

But never mind that. Every word of Griffith’s story is a treasure. It’s full of gems like this one about a woman and her husband who were on a camping road trip (while still running their business) only to find that fellow campers didn’t appreciate their approach:

“They make you feel bad because you’re not unplugging and getting into nature,” Ms. Smith-Adair said. “This is my job. I want to unplug, but I also have to get on that Zoom call real quick.” At an R.V. park near Boise, Idaho, she noticed a Wi-Fi hot spot whose name was the equivalent of a middle finger directed at all Californians.


Okay
, I live in Colorado, where California animosity has run high for quite some time, so I understand the sentiment. Still, I work with lots of Californians and have spent a fair amount of time there. There’s a lot of people! So you can’t blame them if they need to get away from it all. You can blame them, however, for being on a Zoom call while getting away from it all. That’s perfectly fine.

Anyway, I’ve probably gone on enough, but I know my audience, so here’s the obligatory tax angle in this story:

Lots of American travelers try to use a tax rule that carves out exemptions for Americans living abroad. But it requires being out of the country 330 full days of the year, not counting travel. Messing it up brings severe penalties.

“It’s the intermittent fasting of taxes,” said Alexander Stylianoudis, the general counsel at WiFi Tribe, a group that helps facilitate travel for 900 digital nomads. “Everyone talks about it, and everyone does it wrong.”


There are many
, many mistakes a person can make that will not have any tax consequences whatsoever. However, if you make a mistake that then triggers severe tax consequences, I don’t know. Maybe you need to start re-thinking things a bit.

WFH: Economic slackers

Deutsche Bank has an idea: tax folks who can work from home to support those that can’t. It’s part of a whole report of ideas that they acknowledge “may seem radical,” but that may just reflect how desperate people are for solutions.

As far as taxing the WFH crowd goes, I don’t have any empirical evidence to back this up, but I have a hunch they won’t go for it. Still, we do bear some responsibility:

“The sudden shift to WFH means that, for the first time in history, a big chunk of people have disconnected themselves from the face-to-face world yet are still leading a full economic life,” said researcher Luke Templeman in the report. “That means remote workers are contributing less to the infrastructure of the economy whilst still receiving its benefits.”

It’s hard to argue with the logic. Take me, for example. Pre-pandemic, I took the train to work and would occasionally spend money—mostly on bagels—on my walk between where I got off the train and the office. I would go to the gym. I would occasionally meet a friend for coffee in the afternoon. Now I don’t do any of those things! Now multiply that times the millions of other people like me who also aren’t doing any of those things! There’s a massive gap in economic activity that isn’t going to be filled any time soon, and the businesses and people who depended on that activity have significantly reduced their own economic activity. It’s a vicious collapse, and it’s happening everywhere.

But it isn’t as simple as getting me and the millions of work-from-homers back to crowding into trains and offices so that we’ll start buying bagels and coffee again. Even if we wanted to, we can’t; the public health risks are too significant. And so we’re at this logjam, and unfortunately there’s no sign of it breaking loose.

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Updated: January 21, 2021

Caleb Newquist
Caleb Newquist Caleb is Editor-at-Large at Gusto. In 2009, he became the founding editor of Going Concern, the one-of-a-kind voice on the accounting profession, serving in the role for 9 years. Prior to Going Concern, Caleb worked as a CPA for nearly 6 years in New York and Denver. He lives in Denver with his wife, two daughters, and two cats.

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