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The Gig Economy is a Rigged Economy

Cameron ConawayLast Updated: May 31, 2016


I’ve worked remotely for 7 years. Truth be told, since graduate school and except for a 6-month stint, I have only worked remotely.

I wasn’t trying to be part of some movement, and I wasn’t forecasting where things were headed. I just needed a decent job, and couldn’t for the life of me find one near where I lived.

So, in a desperate 2-week scramble that left my nerves and nails frayed, I finally landed a gig teaching an online Shakespeare class for a university in Kansas—a state I’d never been to and a school I’d never heard about.

The work was better than nothing. I made about $2500 per class, but the university typically could only give me one class per semester (including summer session). I could work anywhere, but insurance wasn’t offered. It felt great to help students and to have a job in my field, but at the end of each semester I was scared because I rarely knew if they’d give me a class for the following semester.

So the scramble continued, and since I still couldn’t find something decent in the area, I picked up two additional gigs—one teaching two sections of online English composition for a university in Florida, and another teaching an online creative nonfiction class for talented high school students all throughout the country.

With three gigs that now amounted to full-time work (I had about 100 students at every point throughout the year, including summers), you’d think I’d be rolling, or at least stable. But I was still left in the scramble. I was making about $20k each year, and none of the programs offered health insurance or any stability from semester to semester.

I found myself searching for other gigs while I should have been focusing on my students. And what this cool concept of “work from anywhere” really meant was that I mostly lived at coffee shops or libraries while contemplating moving back in with my parents.

But I marched on, and picked up two other gigs—as a freelance writer for several publications, and as a public speaker. Juggling 6 or 7 gigs at any one time, I’d boosted my yearly revenue to about $30k, but felt plagued by the multi-tasker’s mind; I never felt like I could give any gig my full focus and therefore my best work.

Plus, after rent, health insurance, the car payment, a consolidated student loan payment, a phone bill, and groceries, I was barely keeping my head above water. When a car problem arose, for example, I’d pay with my credit card, and only be able to make $30 payments each month on it. It was always almost maxed out, and I always felt on the brink.

By working for everybody I was working for nobody. I was just spinning the wheels, and wasn’t able to develop a core specialty other than my growing ability to not have a specialty. The companies I worked for didn’t seem to care about me as an individual, and why would they? I wasn’t a long-term asset, and others in the gig economy queue were ready to take my spot if I didn’t want to keep on spinning. The more I spun in this frenetic, desperate way the more I realized millions of other people were doing the same.

The Digital Nomad Coin


On one side of the coin, the side of the coin most often shown, we have the prevailing bright and promising narrative. It’s the one that posits now as the greatest time to work remotely and travel the world, that everybody, especially millennials, increasingly have the ability to choose and be empowered by their work, and the notion put forth by some economists that this rapidly growing gig economy (PDF here) can shore up income inequality because it grants those with lower incomes a greater ability to find work.

As the first of my friends to enter this ‘future of work’ gig economy, I found myself, as the modern digital nomad movement does now—playing up the coolness and potential of this side of the coin (not having to dress up for work, make a commute, etc.).

And, for me, the true coolness finally did open up a bit. In the past few years, and while regularly filing anywhere from six to ten W-2 forms come tax season, I’ve worked in and traveled throughout 15 countries — without actually working for any organizations within those countries. I’d spend time diving into some part of a country’s culture I was fascinated by — sumo wrestling in Japan or Buddhism in Laos, for example — and then find some wifi, get a big ol’ mug of tea, and grade papers or edit articles or work on my next book.

On the other side of the coin, we have compelling research, some of which is presented here at The Wall Street Journal, pointing to how the gig economy likely benefits higher-earning Americans just as much if not more than everybody else. We have brutally honest reporting, such as The gig economy is coming. You probably won’t like it. over at The Boston Globe, which projects a likely scenario: the end of salaries, the end of health insurance, the end of pensions.

In other words, the end of many of the benefits that generations of labor activists have fought for and are still dying for, and that many millennials haven’t been around long enough to understand or really give a shit about.

And it’s all moving so fast that methods to capture snapshots of a nation’s economic health are quickly becoming antiquated. Take this piece, published a few weeks ago by Patrick Gillespie and Sara Ashley O’Brien, which shows how the gig economy is inflating traditional economic indicators:

The U.S. economy in recent months isn’t adding a healthy number of jobs. However, the unemployment rate is at a robust 5.1%, almost half of the 10% it was at during the aftermath of the financial crisis.”

In other words, the gig economy is still part and parcel of the larger rigged economy—where huge swaths of the U.S. middle class have remained economically stagnant for 20 years, union membership has been declining for decades, income inequality has reached a 30-year high, and the percentage of Americans making $25 million or more has grown 73% since 2008.


So while the gig economy may give rise to incredible stories like How to Travel to 20+ Countries While Building a Massive Business in the Process, and make certain economic figures glisten in a way that hides their deeper truths, it’s important that we all at once embrace this gig economy and figure out how to make the best of it. And for starters this means we refuse to become complacent, refuse to believe that access to hundreds of short-term gigs is good enough for people.

I often highlighted the cool factor as a newb in this gig economy, but the secret story was that I was often miserable in the moment and always terrified of what the future held. For years I was working so hard to grade papers that each night before bed I’d dip my fingers for 30 minutes in plastic food storage containers filled with ice water to reduce inflammation so I could do it all again the next day.

To be clear, that is a ridiculously minor complaint compared to the crushing conditions labor movements of years past (and even still today) fought to address, but I do think the thousands of similar stories and the quiet financial desperation faced by many freelance workers highlight a need to be cautious of the loud and cool becoming a smokescreen for the dismantling of knowledge worker labor conditions.

The Future of the Future of Work


Intuit’s 2020 Report paints a clear picture of what the next decade is going to look like. Contingent workers will likely hit that 60 million mark and only grow from there, full-time jobs with benefits will be harder to find, startups and companies of all sizes will gain access to the best talent available while minimizing fixed labor costs, and employees will increasingly have the world as their oyster and their mind on the next gig.

The gig economy will keep rolling, and with it I believe these three strategies will help ensure that both employers and employees can roll with it rather than get rolled over by it:

1. Employers should strive to hire freelancers on a multiple-project basis, and strive to hire under a retainer fee (and assist with insurance) when possible. This will allow the employer to think about the future just as much as the immediate work that needs to be completed, which will save them the time and hassle of having to vet, hire and onboard another freelancer for the next project. In addition, it gives the employee some peace of mind and even brand engagement because they’ll know that they’re locked in for a reasonable period of time.

2. Traditional labor unions need to get with the program. Their work has been the only voice for the middle and lower class physical labor workers for decades, and perhaps nobody both should and is more equipped to carry the lessons they’ve learned into the future of work. Stay true to your machinists and aerospace workers, IAMAW, but know it’s a crucial part of your job to keep tabs on the future and to not be afraid to create massive partnerships with increasingly powerful nonprofit groups like the 300,000-strong Freelancers Union.

3. Employees should—and I know from experience how hard this is to do—strive to take on better (not just more) gigs. If the gig economy is the future of work, focus in this age of mass distraction is the future of how we’ll work. Take it from me: You’re far better off to stay patient and take one or two solid gigs where you can focus, feel a sense of loyalty, and maybe even get some benefits, than you are taking seven gigs that will leave you in an endless scramble. Lastly, join up with local union chapters, join up with the Freelancers Union, and remember that you’re not alone in this.

If in thinking about the future of work we forget to carry with us the lessons of the past, we’re setting the stage for a brutal knowledge worker revolution.

It’s one where tech savvy knowledge will be viewed as little more than the hammer and shovel of yesteryear, where traditional forms of organized labor strikes and protests will have to merge with their digital equivalents, where most have part-time gigs but a relative handful have insurance (let alone a pension) or any security for even the near-term future, and where perks like “work from anywhere!” become the bullfighter’s muleta—the stick and cloth we run towards again and again and again all throughout our lives, completely oblivious to what it all obscures: the sword.


See Also:

What Does the Gig Economy Mean for Workers? (PDF)

OnLabor’s Gig Economy section

Working Remotely Isn’t Always a Dream

Radically Remote: Building Workplace Culture When “Place” Is An Idea

-Art: Bully

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