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The Flexibility Swindle

14 min

Golden Hook & Introduction

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Olivia: A recent study found 94% of employers said productivity stayed the same or even increased with remote work. Yet, so many leaders are desperately trying to force everyone back into the office. The reason has almost nothing to do with productivity, and everything to do with power and control. Jackson: That's wild. So if the work is getting done, and in many cases getting done better, what is the real fight about? It feels like we're all arguing about commute times and office snacks, but there's a much bigger, hidden battle going on. Olivia: There absolutely is. And it's a battle over the very definition of work. That's the central theme of the book we're diving into today: Out of Office: The Big Problem and Bigger Promise of Working from Home by Anne Helen Petersen and Charlie Warzel. Jackson: I've heard this book stirred up quite a bit of debate. Some people love it, others find it a bit frustrating. Olivia: It's definitely provocative, which is what makes it so interesting. And the authors have a unique perspective. They're a couple, both journalists—she's a culture critic famous for her work on millennial burnout, and he's a tech journalist. They actually moved to rural Montana to work remotely years before the pandemic forced everyone else to. So they had a head start on diagnosing all the weird, wonderful, and genuinely terrible parts of this new reality. Jackson: Wow, so they were living the experiment before it became a global mandate. They must have seen the fault lines forming way ahead of the rest of us. Olivia: They did. And their book argues that the whole conversation we're having is framed by a vocabulary that's been subtly corrupted. It all starts with a word we think we love: 'flexibility.'

The Great Flexibility Swindle

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Jackson: Okay, but isn't flexibility the whole point? That's the dream, right? To be able to fit your work around your life, not the other way around. Olivia: That is the dream. But the book makes a powerful case that 'flexibility' has been weaponized by corporations. It's been twisted to mean flexibility for the company, not the worker. And the most chilling example they give is a company called Arise. Jackson: Arise? Never heard of it. Olivia: You've definitely interacted with their workers. Arise is a platform that provides customer service agents for massive companies—we're talking Disney, Airbnb, Home Depot, even Instacart. But here's the catch: the people doing the work aren't employees. They're 'Service Partners.' Jackson: Hold on. 'Service Partners'? That sounds like some kind of Orwellian corporate-speak. What does that actually mean? Olivia: It means they are independent contractors with none of the protections of a normal job. The book lays it out in horrifying detail. To become a 'Service Partner,' you have to pay for your own background check. You have to buy your own equipment—headset, computer, the works. And then, you have to pay for your own unpaid training to learn how to be a customer service agent for, say, Virgin Atlantic. Jackson: Wait, you have to PAY to be trained for a job you're not even getting paid for yet? That sounds like a straight-up scam, not a job. How is that legal? Olivia: It's legal because of that magic word: flexibility. The company's defense, which the book quotes, is that the platform "is not necessarily a guarantee of success... but it offers significant flexibility." You get to choose your own hours, working in short blocks of time. But in exchange for that 'flexibility,' you give up minimum wage, overtime, health insurance, and paid time off. The benefits flow entirely to the corporations, who get a workforce they can scale up or down instantly without any long-term responsibility. Jackson: That is genuinely shocking. It's the gig economy model on steroids, applied to what used to be stable office jobs. You think you're getting freedom, but you're actually buying into a system of total precarity. Olivia: Exactly. The book calls it the "dark promise of flexibility." And it argues this isn't a new phenomenon that just popped up with the internet. They trace it back to the 1980s with companies like AT&T. After an antitrust case, AT&T had to downsize massively. They started talking about becoming a more 'flexible' organization. For the company, that meant being ableto shed workers and office space easily. For the workers, it meant anxiety and instability. One manager's diary entry from that time reads, "the manager who really cares may well kill himself with anxiety and worry." Jackson: So this has been the corporate playbook for decades: rebrand 'instability' as 'flexibility' and sell it back to the workforce as a benefit. It makes you wonder what we were so desperate to be 'flexible' from. What was so bad about the traditional office in the first place that made this seem like a good trade?

Killing the Monoculture

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Olivia: That's the perfect question, because it leads right to the book's second major argument. The authors say the office itself can be a 'bully.' It's not just about the physical space; it's about the culture it creates. They argue that most offices foster what they call a 'monoculture.' Jackson: 'Monoculture.' Can you break that down for me? What does that actually look like in a real office? I'm picturing everyone wearing the same beige uniform. Olivia: It's not quite that literal, but it's close in spirit. A monoculture is an environment where only one type of person, with one type of personality and one way of working, can truly thrive. It's a culture defined by unwritten rules about how you're supposed to act, communicate, and socialize to get ahead. The book tells this incredibly relatable story about a woman named Helen, an introvert working at a Bay Area tech startup. Jackson: Oh, I feel this in my bones already. Olivia: Right? Before the pandemic, Helen was miserable. She was great at her job, but she struggled with the performative aspects of the office. The constant pressure to be 'on' in meetings, the expectation to go to happy hours to get face time with managers. She felt like her actual work was invisible because she wasn't playing the social game. Jackson: I think every introvert who's ever worked in an open-plan office knows exactly what she's talking about. It's this feeling that you're being judged on your personality, not your output. Olivia: Precisely. But then, the pandemic hit and everyone went remote. Suddenly, the playing field was leveled. Communication shifted to written forms like Slack and email, where Helen excelled. She could formulate her thoughts carefully. She joined a Slack channel for working moms and built deeper connections than she ever had at the office bar. The book says the culture finally started to 'bend toward her.' She wasn't just surviving anymore; she was thriving. Jackson: That's such a powerful story. It shows that the 'culture' everyone praises is often just a system that benefits extroverts or people who have the time and energy for all that after-hours socializing. It's not inclusive at all. Olivia: And the book argues this monoculture is a direct descendant of historical work models. They talk about Frederick Winslow Taylor and 'scientific management' in the early 20th century, which treated workers like machines to be optimized. Then came the 'Organization Man' of the 1950s, who was expected to sublimate his entire identity to the corporation in exchange for lifelong security. A quote from that era says he was "imprisoned in brotherhood." Jackson: It's like a corporate cult. You get safety, but you have to give up your soul. And today's 'hustle culture' in startups feels like the 21st-century version of that—just with more hoodies and kombucha. Olivia: Exactly. The book even critiques the whole 'we're a family here' rhetoric that's so common. A comedian is quoted saying, "If an employer ever says ‘We’re like family here’ what they mean is they’re going to ruin you psychologically." Because it blurs boundaries and creates an expectation of unconditional loyalty that only flows one way. Jackson: So if the old culture is broken, what's the alternative? Does the book offer a solution, or just a diagnosis? This is where some readers felt the book was long on problems and short on solutions. Olivia: It does, but the solution isn't a simple five-step plan. It's about intentional management. It's about leaders trusting their employees and establishing clear 'guardrails'—not just personal 'boundaries.' A boundary is something you have to defend yourself. A guardrail is a structural protection the company puts in place for everyone, like 'no meetings on Fridays' or 'no emails after 6 PM.' It's about building a culture of psychological safety, not just providing superficial perks. Jackson: Guardrails, not boundaries. I like that. It shifts the responsibility from the individual worker to the organization. But even with the best culture and the best intentions, the tools we use can still mess everything up.

The Tyranny of Technology

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Olivia: You've hit on the third major pillar of the book. The authors dedicate a whole section to the 'technologies of the office,' and they argue that from the physical layout to the software on our screens, these technologies often make work worse, not better. Jackson: I believe it. I have a love-hate relationship with Slack that leans heavily towards hate most days. Olivia: The book would say that's by design. But it starts with a fantastic historical example. In the 1990s, the ad agency Chiat/Day decided to create the 'office of the future.' The founder, Jay Chiat, declared it a 'virtual office.' No assigned desks, no personal space. You'd come in, check out a laptop and a phone, and find a spot to work. Jackson: That sounds exactly like the modern 'hot-desking' nightmare that so many companies are pushing now. How did it go? Olivia: It was a complete and utter disaster. The design was wild—the receptionist's desk was framed by giant red lips. But employees hated it. They felt rootless, anxious, and constantly surveilled. They started hoarding conference rooms just to have a consistent place to work. The great creative revolution never happened. The company was sold just a few years later. Jackson: It's amazing how we keep making the same mistakes. We're so obsessed with the aesthetics of the future of work that we ignore the human reality. And the surveillance part is what really gets me. Olivia: And that's where the story gets truly dark and connects directly to today. The modern equivalent of that feeling of being watched is employee surveillance software, or 'bossware.' The book highlights a program called Hubstaff. Jackson: Oh boy. What does Hubstaff do? Olivia: It's an 'all-in-one work time tracker.' It takes hundreds of screenshots of an employee's computer throughout the day. It tracks what websites you visit, what emails you write. It even measures your mouse movements and keystrokes, then spits out a daily 'productivity score' down to the percentage. Jackson: That is my actual nightmare. That's not managing, that's just digital stalking. What does that do to a person? Olivia: The book cites a New York Times reporter who installed it on his own computer as an experiment. He found that instead of making him more productive, it just made him more anxious. He started performing for the software, randomly wiggling his mouse or typing nonsense just to keep his score up. The book uses this perfect phrase: he was "LARPing his job." Live Action Role-Playing. He was pretending to work for a machine. Jackson: Wow. So the technology designed to ensure productivity actually just encourages the performance of productivity. It's the digital version of looking busy when the boss walks by your cubicle. Olivia: Exactly. It completely erodes trust. The book argues that companies that resort to this are fundamentally broken. They don't have a productivity problem; they have a management and trust problem. And no amount of technology can fix that. It just makes the cage more high-tech.

Synthesis & Takeaways

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Jackson: So when you put it all together, it feels like a vicious cycle. We try to escape the physical office and its toxic monoculture, but the language of 'flexibility' is used to trap us in precarious work, and the technology we use just recreates the surveillance and performative pressures of the office right in our own homes. Olivia: That's the core of it. The authors argue that this whole debate isn't really about where we work—the office, home, a coffee shop. It's about how we work. Remote work isn't a magic bullet that solves everything. But it is a massive, once-in-a-generation opportunity. It forces companies and workers to have honest, difficult conversations about workload, about trust, about communication, and about what 'work' is even for. It forces a change in the how. Jackson: It's a catalyst. It breaks the old system and gives us a chance to build something better, but only if we're intentional about it. We can't just drift into the future and hope for the best. Olivia: Precisely. And that leads to what I think is the most powerful and resonant quote in the entire book. They write: "Instead of changing our lives to make ourselves better workers, we have to change our work to make our lives better." Jackson: That really flips the script. It's not about life-hacks and productivity tricks to cram more work in. It's about fundamentally redesigning work to serve a healthy, fulfilling life. Olivia: It is. So, a question for everyone listening: What's one 'office' habit, one piece of that old culture—maybe it's performative busyness, or checking email at 10 PM—that you've brought home with you that you could consciously let go of this week? Jackson: That's a great question. We'd love to hear your thoughts. Find us on our socials and share your experience. What's the biggest promise, or the biggest problem, you've found in working from home? Olivia: This is Aibrary, signing off.

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