Remote Careers: State of the Onion — Ep. 40

Why It’s the Best (and Worst) Time to Work Remotely

Today we’re going to have a state of the union on remote work. Have you ever looked at the word “union” and thought it should be pronounced “onion”? Because I sure have… And now that I’ve lost all credibility in your eyes (as if I ever had any to begin with), let’s talk about why it’s the best of times and the worst of times to be working remotely.

I’m going to cover a whole mess of facts and quotes in this short piece. So what do you want to hear first? The good news or the bad news? Well, I can’t hear you, alone in my cavernous digital void, so I’ll assume you want to hear the bad news first, followed by the good news, followed by a few little odds, ends, and tidbits of note.

Why am I doing this? Because on your quest for unusual success stories and inspirational tales, I’m sure you’ve noticed that many coveted jobs are all remote. From Tim Ferriss’s iconic-if-possibly-misleading 4-hour Workweek to the DJs I’ve interviewed to record label managers to songwriters to thought leaders à la Simon Sinek, Marie Forleo, and more — many of the world’s most coveted jobs/businesses are remote or at least, location-independent. I myself spent a decade trying to become location independent as the result of traveling so much and moving to a foreign country twice. For many years, remote work was the dream. Now that we’ve had a pandemic and many more people have gotten a taste of remote life, is it all it’s cracked up to be? 

Let’s find out!

Part One: why is it the worst time to earn money digitally and find a digital job?

An article from the Wall Street Journal says:

“The picture for younger workers is complicated. They are facing stiff competition from people who have been terminated. Workers on the sideline will come back and compete for these jobs.”1

So we need to delineate here between the “good” remote jobs (entrepreneurial bosses, high-paid tech workers, etc.) and the “bad” remote jobs, namely crowdwork or freelance work via low-paying, high competition sites like Upwork, Fiverr, etc.

According to the International Labor Organization:

“Despite performing valuable work for many highly successful companies, compensation from crowdwork is often lower than minimum wages, workers must manage unpredictable income streams, and they work without the standard labour protections of an employment relationship.”2—dgreports/—dcomm/—publ/documents/publication/wcms_645337.pdf

If you’ve ever tried to earn money on crowdwork platforms, that will ring true. And there’s a larger geopolitical issue at play: namely that in US dollars, a living wage is so vastly different between say, San Francisco and rural Pakistan. When people from around the world are competing for the same job in the same currency, people from inexpensive countries have a huge advantage in that they need far less to sustain themselves and can therefore win competitive contracts. So it’s a GREAT time to be a digital employer, perhaps less so to be a digital freelancer. It’s also a GREAT time to get ahead if you’re in a country with a very low cost of living and you have access to great internet and a computer.

If you’re *not* from one of these countries, you will be facing an uphill battle indeed. And with so many people who lost traditional jobs during the pandemic looking for remote work, the competition for coveted roles has never been so fierce.

According to news station WTNH:

“Making money from your backyard became very popular during the pandemic. So did hiring relatively cheap freelancers.” 3

Many people, myself included, are turning to Upwork to outsource menial tasks to boost productivity – something again outlined extensively in books like the 4-hour Workweek. The research for this piece? Outsourced. But hey, at least I’m being honest about it!

Now I’m an outlier in that I’ve been a digital nomad, working remotely, for pretty much my entire career. For at least 10 years before the pandemic, I’ve built businesses remotely using tools like Google Drive, Slack, Skype, Zoom, and even going back to the IRC days and private chat rooms.

So I’m well aware that in the world of code, it’s the OUTPUT that matters, not sitting in a chair for x hours per day. That’s why so many digital experts are so hesitant to have those kinds of pointless restrictions put on them – it feels akin to the TPS reports in Office Space: A pointless waste of time for all involved and a significant reduction in morale for no reason. A-players, as Steve Jobs called them, often want FREEDOM. If we as reasonably intelligent people know that time, not money is our most precious asset, then freedom is what makes us feel like we’ve “made it” more than salary – unless our job is to be Stephen Colbert, in which case showing up to the “office” isn’t so bad, anyway.

But for old-school bosses and people who were introduced to the world of digital work during a pandemic, understanding how output relates to salary can be tricky, when the prior metric was “how long can they sit in a dark cubicle without tearing their hair out?”

From a Forbes article:

As Adam Jackson, CEO of talent network Braintrust, says: “Companies looking to cut pay for employees who change geographic locations when their job can be done just as well remotely as in person (an important criteria) are essentially telling those employees they were overpaid before Covid and this is a ‘fair market adjustment’ of their pay. If you’re an employee that is being subjected to this, you should challenge your employer to admit that they value you less now than before.  If they can’t admit that, they cannot justify the pay reduction.”4

Because while many bosses intuitively feel that work isn’t being done, experienced digital teams are able to tell who is working and who isn’t based on output.

Traditional bosses may feel that people being absent from an office is a sign of work not being done, but digital teams feel that employees who are, let’s say, in an office but never signed into Slack are a far bigger liability. It’s a question of “where is it most important to show up and how?”

Is it more important to be gossipping in person by a literal water cooler? Or to be handing off tasks in real-time on Slack?

For me, I value teams that are ever-present digitally. I couldn’t care less where they’re located or if they’re looking at a beach while they work, as long as everything gets done.

But this part is supposed to be about why it’s a bad time for remote work, so here’s a barrage of facts:

Elise Gould, a senior economist at the Economic Policy Institute says:

“Because there is a large pool of unemployed workers, companies can pick exactly who they want and skip over people with less experience.”5

And if you trust a single word someone at Facebook says, then let’s see what Brynn Harrington, Facebook’s VP of People’s Growth has to say:

“Obviously this is working from home during a pandemic, we are not in a period of healthy remote work. We have people juggling care giving responsibilities, we have people living in small apartments with roommates, those people desperately want to get back into offices, and we’re working really hard to do that, as soon as it’s safe to open our offices.”6

From Voanews:

“Younger workers are struggling more when it comes to feeling engaged or excited about work while working from home, according to the study.”7

And from an article on the BBC:

“Microsoft chief executive Satya Nadella said the lack of division between private life and work life meant “it sometimes feels like you are sleeping at work.”8

So knowing when to “switch off” is a major problem.

In an article on Buffer, CEO of Doist Amir Salihefendic says:

“Remote work isn’t just a different way to work – it’s a different way to live. And, unlike what you might see on Instagram, working remotely doesn’t mean you jet set to exotic locations to drink piña coladas on the beach. We need to acknowledge that isolation, anxiety, and depression are significant problems when working remotely, and we must figure out ways and systems to resolve these complex issues.”9

Couple that with reduced money and struggling to find crowdwork gigs, and you got yourself a powerfully depressing cocktail.

Unplugging after work and loneliness are the biggest struggles of remote life according to a study in the same article, and I agree. Even in the best case — someone like Mark Manson who has made millions as a blogger — has often talked about the downsides of being a digital nomad.

So if your idea for Beating the Often Path is making money remotely, you have 3 options: 1) Fight it out on Upwork or crowdwork sites, 2) Get a remote job from companies that are all remote right now, or 3) Build your own team of freelancers and either start an agency or go the influencer route, and sell digital products in the open waters of the marketplace. None of these are particularly easy.

So now that we’ve gotten the doom-and-gloom out of the way, let’s move on to a more positive note, shall we?

Part Two: why it’s the BEST time to be engaged in remote work.

Facebook’s Brynn Harrington (again, let’s not look at any of the news regarding Facebook lately, lest we see them in a less-than-favorable light… *cough*.)

“…parents who are closer to their children and are happy to cut their commute time and optimise their work day, they’re thrilled to work from home.”

Source: am parent, can confirm.

An article from Forbes states:

“The need for sprawling physical office spaces is going to become a thing of the past. Completely remote companies with no HQ or organizational office will become a reality.”10

Again, contrary to what evil bosses would have you believe, remote workers are considerably cheaper than their in-office counterparts – no desk space, no internet, no coffee, no non-dairy creamer, no plastic coffee stir sticks, no toilet upkeep, lord… the office toilets… 

An article from Global Trade Magazine says:

“The demand for digital services and professionals providing those services has led to more people turning to the industry to find jobs. Digital marketing has emerged as an industry that has the potential to absorb a large section of the newly available talent. As long as they have a computer and a fast and reliable internet connection, any person can train and start working in this sector.”11

Hey! That sounds a lot like me! I’m any person with an internet connection!

Hubstaff sez:

“In our recent State of Remote Work survey, we found that 84.5% of companies intend to continue offering some remote work options after the pandemic. Some, like Twitter, have even instituted a permanent remote working policy.”12

Sounds like a GREAT time to be remote!

And with this newfound understanding that many of today’s jobs can be done just as well (if not better) remotely, comes a certain power back in the hands of the workforce.

As CNBC says:

“Even among those who aren’t considering changing jobs, half of people currently working remotely say if their current company doesn’t continue to offer remote-work options long-term, they’ll look for a job at a company that does.”13

Because the curtain has been pulled back, and especially people with kids are realizing that output and the bottom line matter more to everybody than any other romanticized notions of what could or couldn’t be.

The article continues:

“People who can work remotely tend to be white, college-educated and higher-income workers. If a post-pandemic workplace accelerates this trend, it could worsen existing income inequality.” 

Hey, I’m a white, college-educated, higher-income worker! That’s great! Oh wait a minute… Maybe that’s not so great… Maybe that’s a pretty big downside to this emerging shadow economy or cottage industry or whatever you want to call this.

An article from Upwork’s own blog says:

“We know already that the most in-demand professionals place high value on flexibility. For example, the youngest generations are most likely to freelance. And professionals craving flexibility will increasingly have managers who not only understand this priority but will themselves expect it.”14

So all’s well for intelligent, digital folk who may or may not be white and come from a place of privilege to begin with…

But, another article from Forbes says:

“Skills gaps have widened due to the pandemic, and the increase in job automation has catalyzed the demand for retraining and skill-upping.”15

With entire job categorizes vanishing in the face of AI and automation, more people need to take remote-ness seriously, that’s my takeaway anyways. And regardless of your background, there has never in human history been more information readily available for free, so learning these in-demand skills has never been more possible.

So let’s bring it on home with a conclusion here, and my takeaway from the whole thing.


First: The pandemic sped up a process that was already in place—a global shift towards digital remote work. This event has made it more normal for workers to be remote, and for the companies who survived and/or thrived during the pandemic, it was a black-and-white reminder that being physically in an office isn’t important for the bottom line of every company. While some suffered greatly or closed down, others had their best year ever. If you’re a business owner, there has NEVER been a better time to build a remote team.

Second: Remote work requires digital skills. These skills are attainable, but they require serious study and commitment. Zoom is step one. There are hundreds of other programs and digital languages we need to be versed in to be at the upper end of the skill gap. So if this is a path you desire, it’s important to be constantly levelling up your own skills and to take all things digitally very seriously.

Lastly: Remote work comes with its own share of very real challenges. The digital nomad dream is both better and worse for parents. The pandemic has also shown us how taxing remote work can be. Here too the curtain has been pulled back, leaving many with significant mental health issues. In short, digital work isn’t for the faint of heart.

And on a final note: In some sense, we may not have a choice. The bus is leaving, so to speak, and we are either on it or off it. At a policy level, this means that fast internet NEEDS to be a right, not a privilege. Literally EVERY person should have both the internet and a computer, otherwise they stand no chance. We need to be mindful of communities left behind by this shift. And on a personal note: you can either decide to jump on the digital train or not, but if you ignore this greater shift, you do so at your peril!

I hope you enjoyed this extra special episode of Beat the Often Path — the show where we help you see your life and career in exciting new ways.

Rant, ova!

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