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Figuring Out the Freelance Economy

Could new technology make the lives of freelancers less lonely and more secure?

Photo collage by Adam Mignanelli

This story appeared in the September issue of VICE magazine. Click HERE to subscribe.

The life of the freelancer is visibly lonely but invisibly crowded. It may seem like just you, your laptop, and your coffee shop, while all along you're competing for a livelihood with a crowd of strangers. Some of them might even work in the same coffee shop, emailing with the same bosses, each of you being played off the other. That disguise of loneliness is part of what makes freelancers so easy to rip off.

The grass may be somewhat greener in Wellington, New Zealand's seaside capital, on the southern end of North Island. It's the home of Enspiral, the subject of whispers and legends among knowing freelancers the world over—a parallel universe where self-employment is no longer lonely and powerless.

From 2003 to 2010, Enspiral was just the domain name used by Joshua Vial, an Australian software developer who lives in Wellington, for his personal-consulting business. By 2010, he was trying to spend less time on paid work and more on volunteer projects, and he turned Enspiral into a tool to help others do the same—sharing gig opportunities and freeing hours for good works. The company became a cooperative, co-owned by its members, of whom there are now about 40. Enspiral also includes about 250 "contributors" who are participants in the network, and 15 small companies called "ventures." Many members are techies of some sort, but people of any profession can, in principle, join. Vial stepped down from its board earlier this year. He's now, more or less, just another member.

Today, Enspiral serves as a financially lean, but anecdotally essential, connective fiber among these independent workers and small companies. Enspiral members still pass jobs around to help stabilize the ups and downs of freelancing, but now they also fund one another's business experiments and assist one another if things go sour. They hold retreats twice a year. They're relying less on the Robin Hood strategy of taking corporate contracts to pay for volunteer time by creating their own jobs and companies with do-gooding built in. Enspiral-affiliated ventures, for instance, include ActionStation, an online organizing tool; Scoop, an alternative-news source; and Chalkle, an education platform.

Maybe, when equality is its premise, work need not be segregated from life, from the ambitions and needs of our actual selves.

I spent a morning with Vial in a conference room at Enspiral Dev Academy, a web-developer boot camp he opened in 2014. He gave me a tour of the network on his laptop. Enspiralites work at several co-working spaces across town—and, increasingly, outside Wellington—but the space that most unites them is a cluster of online tools. Some are commercial platforms like GitHub and Slack; the most important ones, though, had to be built from scratch. My.enspiral.com is home to a bookkeeping tool, and at Cobudget.co, contributors and members allocate funds for their projects and worthy causes. Inspired by the Occupy movement, Loomio.org serves as the network's decision-making platform, and now activists, schools, governments, and companies from all over the world use it.

As Vial showed me the various tools and tasks, I asked questions about how they prevent bad actors. What if someone wanted to rig a decision on Cobudget to get money for his or her project? What if the project was a sham? He replied with a small shrug.

"It's a high-trust network," he said. "We don't try to optimize for low-trust situations."

A short walk from the Dev Academy, at the closest thing to Enspiral's main office, I met Alanna Krause, a migrant from California who found Enspiral early in its transition to collectivity. She is now, among other things, the "bossless leadership geek" at Loomio and an Enspiral board member. She and some of her co-workers relayed the litany of ways the network differs from any other co-working space.

"Somebody's laptop gets stolen, we buy them a new one," Krause told me "Somebody's house burns down, we pay their rent. Somebody's organization has to downsize, the other ones will hire those people." They also cover one another's therapy sessions, when needed. And the result of this safety net, she thinks, is "actual innovation." When you know someone has your back, it's easier to take risks.

"Co-ownership is another factor that builds trust," added Hannah Salmon, an artist who was part of the Dev Academy's inaugural class and writes code for Loomio. Just as Enspiral's members are co-owners, Loomio is a worker-owned cooperative. She was leaning her body against Ben Knight—her partner, a founder of Loomio, and the drummer in their punk band, Unsanitary Napkin.

Among the Enspiralites, I noticed an unusually affectionate office culture, with evidence of both monogamous couples and more polyamorous tendencies. Gone, it seems, is at least a major portion of the freelancer's conventional loneliness, together with some of the ramparts that guard the work-life divide. I was assured that consent reigns over all and that, contradicting the conventional wisdom of HR the world over, the cuddling doesn't cause problems at work.

Maybe problems just haven't happened yet—or maybe this miracle has something to do with the trust and the co-ownership, which supplant the dynamics of hierarchy that make romance in conventional offices so toxic. Maybe, when equality is its premise, work need not be segregated from life, from the ambitions and needs of our actual selves.

This story appeared in the September issue of VICE magazine. Click HERE to subscribe.