"The future of work is not working."

Kill the career.

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A few months ago my partner, Anne Helen Petersen, and I set out to write a book about remote work and the future of the office. We interviewed over 100 people and surveyed about 800 more. We talked to tech workers, academics, middle managers at retail companies, lawyers, doctors, management coaches, gig workers, farmers — you name it. We pressed them about HR problems, diversity and inclusion, disability rights and universal design, commercial office space, commutes, meetings, surveillance software and more. Occasionally, the interviews turned into therapy sessions.

Almost always, the conversation veered toward a universal theme: our relationship to work is broken. Generally speaking, our attitude toward our jobs is toxic, our demands on individuals are too great, and work’s rewards are not commensurate with the time spent. Most of us lack the support we need to balance our careers with any life outside the workplace. According to a 2019 Gallup Report on the State of the Global Workforce, 71 percent of adults say they’re not engaged at work, and 19 percent say they’re actively disengaged. Bleak.

Here, the pandemic has been clarifying. American work/office culture feels unsustainable. It’s not sustainable for the individuals who are burning out. As our pandemic workdays grow longer, it’s clear that this is not sustainable for our families. Profits might be steady, even soaring, but the workforce, like the communities and our lived environments, are collapsing. 

In the book, we argue that that new, genuine style of flexible work (not merely dressing up gig-economy/contract worker precarity as flexibility) is one way out of this hole. Flexibility means hybrid or remote style work but it also means true support from companies in the form of paid leave, support for unions, DE&I initiatives that aren’t windowdressing, and shifting focus away from exponential growth at all costs. A lot of this might be wishful thinking, but the truth is that our jobs are going to continue to crush us unless we undertake the extraordinarily difficult project of rethinking the placement of work in our lives.

There’s a lot of conversation about future of work right now — but we have very few future models of work to consider. There are fully distributed companies like Gitlab, which have employees dispersed around the world and working asynchronously. There are organizations like Dropbox, which are going remote-first and fundamentally re-thinking what office space should look like. Both of those are interesting examples and potentially radical. But I’ve recently been fascinated Gumroad, a company that helps creators sells things online, that’s practicing what feels like a different mode of knowledge work entirely. In short: it is a meeting-less, full-time employee-less company.

Gumroad’s CEO, Sahil Lavingia describes the company’s strategy as eschewing growth at all costs for “freedom at all costs.” Employees are paid hourly and work as much or as little as they need. There are no meetings or deadlines — just broad product goals to work toward. Projects happen iteratively and take as long as they take. The company’s Head of Product is a former Amazon employee who works 10 hours a week and makes roughly $120,000 a year. Here’s how a different Gumroad-er described working at the company: “I could contract 20-35 hours a week, and for a couple days a week, incubate ideas and work on my next thing.”

Over the last five years Lavingia purposefully destroyed Gumroad’s corporate culture. This isn’t to say Gumroad has a bad or peculiar culture — it has no culture at all. “I’m not friends with any of my [part-time] employees,” Lavingia told me recently. “We get along fine but there’s no real a water cooler talk or chit chat. Every time we talk, it’s about Gumroad.”

This policy probably sounds cold and joyless. But I’d argue there’s also something admirable about it. All work — even in the best companies — is transactional, but we disguise this fact by dressing our jobs up in the language of corporate culture. We use language like ‘we’re all a family, here,which sounds really nice in theory but is often a clever way to break down the boundaries between work and life. Even if you genuinely care about your company and your coworkers, the family posture is still a lie. It frames a primarily transactional relationship as a primarily emotional one.

“When you’re operating this way, you’re only getting people who really want to be there,” Lavingia told me. “It’s definitely way more transactional but there’s no guilt keeping people in jobs they shouldn’t be in. It’s so common to see people toiling at places they don’t want to be because their identity and the company’s identity are all tangled up in each other.”

Lavingia’s ideas, once put into practice, are extreme. But what he describes above — workers who are miserable because their identities are wrapped up in their jobs and the status conferred by their companies — is a phenomenon I’ve seen throughout our reporting for the book. I’ve also felt it personally. For years, I’ve let the status of a job title or the brand of an organization stand in for my feelings about the actual work I was doing. And then there’s the insidious family issue. When relationships with bosses feel familial, the dynamic introduces guilt and passive aggression into the workplace. Workers begin to sublimate their own desires and needs for those of the company. Our reporting suggests that suppressing these feelings leads to resentment and eventually depression or total burnout.

This could be one reason why Lavingia’s employees have continually refused his offers for full-time employment. “I keep asking, ‘do you want a job?’ and every single person — 100 percent of people — say, ‘I’d rather work 20-30 hours a week and bill hourly,’” he said.

It’s important to note that Gumroad’s model is operating in a rarified employment space. Web development work is inherently flexible and readily lends itself to easily quantifiable, asynchronous work. The company is also part of a competitive industry and tech workers have a lot of labor power to set terms and find multiple gigs that pay generously. Gumroad is banking on this kind of stability among a niche subset of workers — and it allows them to offer absolutely zero benefits. The company doesn’t provide healthcare or offer stipend for their computers or internet connections. And Lavingia is unapologetic about the fact that this model will not work for many people. (It’s worth noting, of course, that it would work for more if we had universal healthcare that wasn’t connected to employment).

But just because Gumroad’s model isn’t immediately or perfectly scalable doesn’t mean it isn’t a worthwhile thought experiment in what work could look like. Even if Lavingia’s approach seems too Rationalist Tech Bro-y for you, it’s worth noting that Gumroad settled on its strategy after chasing exponential growth only to collapse — in 2015, after failing to raise funding, Lavingia had to lay off his entire company. Now, the company focuses on growing sustainably, which is inherently unexciting, but makes for much more pleasant work.

In a blog post about his working philosophy, Lavingia argues, “the future of work is not working.” That’s catchy but I don’t think it’s quite right. What Lavingia is describing is closer to “the future of work is not a career.” Working at Gumroad is, in and of itself, not a career. It is not some flashy status symbol. It is not an identity. You don’t spend your whole life working up toward it. The job is transactional and utilitarian. Lavinigia wants it to be a way station for talented people as they build multi-dimensional lives.

“I will help people start a company, if that’s what they want,” he told me. “That’s what I want to build into the model of working here. You come to this job, work a few years, then after a while you leave and you start a company or get what you need to go someplace else. There’s no real room for growth here so it leaves the bullshit politicking at the door. You’re not sitting and waiting for a promotion that never comes, you’re building toward the next thing.”

I imagine there are plenty of people who’ll call bullshit on this strategy or suggest that it’s a clever way to weasel out of providing the very infrastructure that most people need to live balanced, flexible lives. I saw one tweet about Lavingia’s blog post that read “The entire post is just a bunch of red flags.” I’m sympathetic to that.

But Gumroad’s new way of working doesn’t interest me because it’s a foolproof template. It interests me because it asks us all a fairly blunt question: what do we actually need from our working lives? Is it money? Career advancement? A sense of community? Healthcare? All of the above? What parts of what we currently ask of our job are extraneous — and far more about status or ego or insecurity? Is the logo on your business card more important than the work you do or the satisfaction you get from what you produce?

These are the types of hard questions we need to be asking ourselves — starting with executives and managers — if we’re serious about re-imagining how we work. If that sounds radical, it’s because it is. Our relationship to our jobs is broken. Repairing that relationship will require some radical thinking.

A new word for you

Writers are often tasked with taking universal feelings that are vague and hard to pin down and put a name to them. I’ve been writing for a decade about the ennui that we all feel from having our lives totally intermediated by powerful connected devices and I’ve never been able to capture it this succinctly. “Screensick” is brilliant — in my head it recalls motion sickness. It’s a temporary condition that’s caused by your environment messing up your equilibrium. That’s often how I feel when I open up the internet on my phone. I’ll be having a great day and suddenly a push alert, tweet, or an email pops in and throws everything out of balance. My mood goes with it and I’m off-kilter. Screensick!

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