How To Overthrow Your Boss And Burn Your Company To The Ground

The old rules no longer apply, so these three people are inventing new ways to work.

How To Overthrow Your Boss And Burn Your Company To The Ground
[Photo: Flickr user Montecruz Foto]

Work as we have always known it is done.


But that doesn’t mean you can stop working. In fact, it’s more than likely that you’re reading this as you take a short break from your job. Maybe it’s 11 p.m.; maybe it’s Saturday. Your work is never done, even though work is.

While work as a time-bound, location-based means to earn money until you can retire with a pension is no more, most of us still need to earn a living. What you do and where you do it is likely so different from your parents’ or grandparents’ definition of work that they can barely be described using the same words.

Offices? Increasingly irrelevant according to a 2013 survey of 26,000 business managers in 90 countries conducted by Regus, a workspace provider, that found nearly half of workers do their jobs remotely. (This may explain the rise in co-working spaces.)


Forty-hour workweeks? Forget it: a report drawn from 9,700 workers surveyed across eight countries this year by Ernst & Young revealed more and more of us are working longer hours at the office, at home, and on the go–as if you didn’t already know that.

Weekends? Might as well be another workday, according to a National Bureau of Economic Research survey that found Americans work far more weekends than Europeans. Retirement? Hardly an option for most people, and not even a thought for the 22% of middle-class Americans surveyed by Wells Fargo who said they’d rather die early than not have enough savings to live on.

That’s the bad news.

Now the good news: There’s never been a better time for us to take our careers back. It’s time for each of us to make our careers work for us, to wrest this always-on, safety net-less nightmare into a new and different kind of dream.

If we acknowledge that the traditional contact between workers and companies has broken down, we can begin to free ourselves from the simultaneous demand for more (from us) and the promise of less (from them). Why are employees (if they’re even considered such in an increasingly freelance economy) still holding up their end?


Time to take work back.

I’ve had the opportunity to think a lot about this topic this year as I’ve been helping to develop a new publication called MONDAY, dedicated to the people rethinking their relationship to work and making their work work for them. This includes founders of companies like The Thing Quarterly, a San Francisco-based art subscription service whose cofounder Jonn Herschend told me: “I like to work, but I don’t want to be in a situation where people feel like they just have to work to show that they’re working . . . We’re running a business now. We get to make the rules.”

It also includes people working within large, traditional companies like the ad agency Team One that redesigned its 70,000-square-foot Los Angeles office space to encourage interactions and spark ideas. “Before, we were across four floors and there wasn’t a lot of bumping into people,” explained Allison Citino, the company’s communications director told me. “Now things are much more spontaneous and collaborations happen easier.”

Everyone we’ve spoken to has shown us that the future of work looks different for each of us. For some, it’s no office; for others, it’s a more humane one. For everyone who strikes out on their own, there are others figuring out how to cultivate autonomy within even the most top-down companies. In an era when people are encouraged to customize every experience, it’s time we stop seeing work as an off-the-rack experience one must either accept, even if it doesn’t fit or feels wrong, or opt out entirely.

For some, this customized approach involves entrepreneurship. These brave souls are starting their own businesses and running them their own ways. According to the Small Business Administration, there were 28 million small businesses in the U.S. in 2011. In the U.K., the Centre for Entrepreneurs released a study at the start of 2015 showing that 581,173 new businesses were created in 2014, beating the previous all-time high of 526,446 in 2013.


The Employee Turned Entrepreneur

One such entrepreneur is Jessica Almeleh, a New York-based fashion designer who recently left a job at a large company to start her own line called Pincus NY. Having spent years creating lines for well-known brands such as Danskin, Champion, and Walmart, and learning about production, pricing, and scale, Almeleh decided to apply the knowledge she developed on the job to something she was more personally invested in. “It’s the kind of thing a lot of people daydream about from their cubicle,” she told me. “I’ve chosen to work in the same industry, but it’s different.”

Jessica Almeleh

Whereas before, Almeleh’s employers made decisions based on large-scale projections and market trends, as the head of her own company, she’s having to pay much closer attention to her customers and be responsive. “I’m aware that my customer will decide things for me,” she said. “You can’t just make it because you want to make it. At the end of the day, it’s not a craft project. It has to make money; it has to sell.”

“Definitely it’s an adjustment,” she said. It’s also been an education. “I have to learn new things. I’m a designer. I’ve never been in sales or PR. Being a new company, you don’t have past information to guide you.”

As Almeleh explained, independence brings with it new risks, ones that workers in large companies tend to be insulated from. “I have to be careful in what I decide to do because everything is coming out of my pocket,” she said. “It’s liberating in ways, because I don’t have to answer to anyone else, but there’s no one to blame but me if it doesn’t work out.”

Technology also contributes to people reimagining how–and where–they do their jobs. The long digital leash of smartphones can been seen as a way for you to be “on” all the time, but it can also be a way to work from anywhere in the world. As Sara Sutton Fell, CEO of FlexJobs, told Fast Company last year: “In most white-collar jobs, I’d say 99% of people are already working remotely, in that they take work home. It creeps into our work style already. I think it’s just not formalized by either the employer or employee.”


A recent piece by Erin Reid in Harvard Business Review illustrated some of the ways that technology has freed some knowledge workers. “I skied five days last week. I took calls in the morning and in the evening, but I was able to be there for my son when he needed me to be,” one pseudonymous senior manager boasted to Reid. Sure, this involved a bit of subterfuge (and a whole lot of privilege) on that guy’s part, but others are making the “work-anywhere” approach work for them in more places than their home office.

The World Traveling Boy Genius

Take Keith Kurson, the founder and CEO of Subeta, a social game platform. Kurson isn’t your usual startup founder: He developed his site as a teenager growing up, as he puts it, “super, super poor in North Carolina.” He dropped out of high school and emancipated himself so that he could fully run his own company.

Keith Kurson

“I spent all of elementary school being told how gifted I was, and found middle school and high school incredibly boring, so I skipped classes a lot,” Kurson said in an email. “I think my ambition and hope for a better life than North Carolina was providing pushed me to keep working every day to make what I could see in the future happen.”

Kurson is currently in Paris, where he FaceTimed with me from a coworking space. He was in France after leaving the Bay Area for a six-month trip that crossed Iceland, Spain, Italy, Germany, Sweden, Austria, and Hungary. All along the way, he kept working remotely.

“I think I’m well suited for this . . . I get a lot of changes of scenery, I get to go to a lot of places, but I’m still working.”


Of course, it helps that Kurson has trusted employees–including his sister–who keep his operation going as he travels, but he still manages to find ways to plug in as he’s unplugging.

The energy of the coworking space excites him, Kurson said. “People would frequently sit at the same table and ask what my skills were, and then start asking about Javascript, etc.” he said. “If I had design questions, I could easily turn to the person next to me and ask if they’d look over what I was doing, and if they had any suggestions.

“It made it feel a lot like working with people, without us all working on the same things,” he said.

Interestingly, Kurson said that, as he plans to move to San Francisco this summer, he’s considering doing something he’s never done in his entire working life: handing over the reins of his company and getting an office job. “I’m going to be turning 26, I’ve been my boss the whole time, and never had the structure of a real job,” he said. “I love the freedom and I imagine I’ll miss that, but I want the structure.”

“I’m interested to see how it impacts me to have a boss,” he said. “I’m fortunate that I’ve built this awesome company, and it means that I get to be really picky about what I do next.”


Choosing to work for someone else can also be seen as an expression of work customization: Someone like Kurson can decide to take his resources–his talent, his experience, and above all, his time–and lease them to a company. Whatever he decides, it’s his decision.

The Master Of The Sharing Economy

Another person who fully customized his career is Lucas Bronte, who lives in San Francisco and works as a full-time Airbnb host, housecleaner, and key concierge for other hosts, a trainer, and works part-time at a YMCA. He used to used to pick up gigs on TaskRabbit, but found that the network had changed in ways that didn’t suit him.

Lucas Bronte

“It is Tetris sometimes,” he admits. “It takes a certain kind of person to be okay with not having a regular paycheck,” Bronte said. “I feel like I’m in control, whatever that means.”


Bronte used to work as a theatrical stagehand, so he’s used to piecemeal and seasonal work. His various gigs allow him time to go to the gym, see friends, attend matinees, and take time off, although he does call it “a day off-ish.”

“Hell yeah, I can take a week off,” he said. “That’s another thing about this work: When I get home, that’s pretty much it.”

Having a high energy level, flexibility, and good boundaries are important to this mode of work, but time management is the most essential thing for Bronte. He shares a Google calendar with his clients and keeps a whiteboard calendar beside his computer, blocking out time and tasks. “It was out of necessity,” he said. “I thought, alright, I gotta get a better system. I need to be better at this.”

“It’s the lifestyle I’ve chosen, and I need to do it right. I need to be successful.”

It’s this kind of customization and self-direction that Sara Horowitz, founder and executive director of the Freelancers Union, says will define work in the next decade. “I think it’s going to be like a portfolio, a range of different kinds of gigs. That will become more organic, and there’ll be business infrastructure and, hopefully, social infrastructure that addresses that change.”


“I think that people with skills have had the best opportunities to take advantage of it,” she said. “It’s not like this is just happening to high-tech workers. This is how nannies have worked, and security guards, and a lot of people across the economic spectrum.”

While the promises of work have changed and the traditional paths to success have been altered beyond recognition, hardworking people are still figuring out ways that they can, well, make it work. It’s true that fewer of us will experience a single career that spans from our twenties to our twilight years, capped with retirement. But it doesn’t matter, because it’s hardly an aspiration for many of us anymore. The opportunity to reimagine ourselves, repave our paths through the world, and rewrite the rules of work is something previous generations couldn’t dream of. The way things are now may not be perfect, but, if you’re lucky, it works.

Related: This is what it looks like to break the rules at work