The inciting incident is always an act of injustice. For me, I suppose, it was the period of time in my twenties when I had the mentality of an office worker drilled into me. “You’re supposed to be chained to that thing,” a boss said to me of my desk when, I think, I had wandered off for a bathroom break. What we were supposed to be doing at our desk was often a big mystery – the boss might disappear for hours at a time, a clear task might materialise only once a week or so, everybody had their perfected tricks for how to spend the long dead time staring at their screens – but what was clear was that everybody was supposed to be there, chained to their desks. That was the work.
But it eventually became clear that, for a large number of people, that just wasn’t the case. Gradually and then suddenly I noticed that what the bosses were really doing was balancing a large number of projects at once. A new term of art showed up in my world – in documentary film production in the US – the “days of the week” contract. So-and-so senior would be working one day a week on a given project and then the other days on other things. But it was a complete fiction. In fact, that boss was working on all those different projects “full-time” simultaneously, and delegating all the work to us. They were making a killing of these multiple jobs, even while their underlings were expected to still be chained to their desks.
Actually, though, the underlings were not all so obedient. The further down the food chain you went, the more people were proudly skipping out on work. One of the PAs had a full-time second job as a bartender in the evenings. It seemed like any time you turned on the television some politician was talking about how his mother had worked three jobs to support the family, with no discussion of how working one job impacted her efficacy at the next. Companies like Uber were busy selling the idea of taxi-driving as viable part-time work.
The only people, it seemed, who weren’t double-timing their work were the ones caught in the middle, the run-of-the-mill white collar workers, the ones who had done well in school and then took the jobs they could and were trying to do everything right, with maybe even a dose of authentic company loyalty in the mix. They were the ones really putting in the hours while everybody above and below them had a pleasurably mercenary attitude towards their work.
So it seemed, anyway, until the word “side hustle” started to slip increasingly into office conversations. Laptop work generated this ever-present temptation to do something else with the dead hours of the day. And instead of just scrolling through the newspaper, you could try to monetise your passion, or at least to flog some of your possessions for cash. In retrospect, what enterprises like Airbnb hosting or eBay resale might really have been doing was reprogramming nice white-collar people with the kind of mentality needed to cheat on their jobs. Shows like Weeds and Breaking Bad were, from one way of looking at it, an ode to the side hustle – with Breaking Bad’s Skyler White selling items on eBay even while giving her husband a handjob and with Walter, needless to say, deftly combining a methamphetamine empire with high school teaching – and presumed a very different relationship to one’s work than did shows like The Office or Parks and Recreation where everybody (whether happily or not) identified themselves almost entirely with their nine to five.
All through the 2010s the internet teased at workplace polyamory, but the turning point was 2020. The pandemic exacerbated the tendencies that were already there. Suddenly, two-timing your job was everywhere.
In 2021, the anonymously administered website “Overemployed” launched with the tagline: “Work Two Remote Jobs. Reach Financial Freedom”. In a note explaining his origin story, “Isaac”, the site’s founder, wrote that, facing layoffs, he landed a new offer and was getting ready to negotiate his severance when he had his eureka moment. “It dawned on me, why quit my job at all?” he wrote. “I decided to stay on at my old job while starting my new job, overlapping two jobs as a hedge against uncertainty during the pandemic”. He continued: “I told myself I’d only do it until the end of the month, but as time went on I began to wonder – why not stick around for a few more months and get my deferred compensation?” Isaac claims that his strategy of working two jobs simultaneously has netted him $300,000 additional income with no evident downside – he hasn’t been caught and he keeps to a 40-hour workweek.
That same year the New York Times‘ “Ethicist” column ran a letter from the other side – by a contributor who had recommended a friend for a position only to discover that the friend had had no intention of quitting her old job. Kwame Anthony Appiah, the columnist, was stern in his rebuke. “What your friend is doing is wrong in all sorts of ways,” he wrote. “She’s being dishonest in deceiving both employers. She’s taking advantage of the trust these companies place in their employees and of colleagues who don’t abuse this trust”. He advised threatening to report the friend but also claimed that the letter-writer “would be justified in reporting her without giving her further notice”. The old guard wasn’t having the notion of workplace polyamory.
A clear battle line was drawn through the concept of employment. For Appiah, a job was essentially about loyalty – about serving in good faith the terms of a contract that you had agreed to. For “Isaac,” and the community connected to the Overemployed website, the existential value of a job had broken down a long time ago. In the start-up economy, very few employers offered any real security, and if they could fire employees virtually at a whim, employees had an obligation to look after themselves first – with additional sources of income as the best protection against being made redundant.
There was a very obvious practical component to the advice Isaac was peddling, but as he made clear in his statement of purpose, there was a political, if not spiritual, side as well. “More than anything else, I wanted to organize a community to give the man, aka Corporate America, the middle finger for always trying to screw the little people over,” he wrote.
It’s maybe a little difficult to get solid numbers on how many people are two-timing their jobs, in the way that it’s not so easy to get survey information on how many people are cheating on their partners. The St Louis Fed, a US federal reserve bank that runs a respected economic research division, found a significant jump in employed people working more than one job. The number rose to over 5 per cent in 2024, and the growth came overwhelmingly among college graduates. It was the first time that cohort has surpassed non-graduates in multiple job-holding.
It’s not only a stateside phenomenon. In the UK, the 2025 Employment Hero’s Annual Jobs Report found that one in five UK workers held multiple positions, and that 42 per cent of Gen Z workers were considering juggling multiple jobs. Owl Labs’ 2025 “State of Hybrid Work” report showed that the majority of workers go to the office three or four days a week, that 29 per cent of them had side hustles and that over half have scheduled personal appointments during traditional working hours.
In their analysis, the St Louis Fed speculated that the multiple job-holding may well be “attributed to a desire to keep pace with inflation”. But that seems to me to undersell how starkly divergent the conception of work is between those with one job and those with two. Behind the steady rise of multiple job-holding within the laptop class is a new quiet common-sense mercenary mindset about work. A job is about optimising one’s outcomes, and like any investor with a stock portfolio it doesn’t really make much sense to give away all one’s labour on a single bet. That common sense holds that the workers’ autonomy comes first.
Remote work makes workplace polyamory far, far easier than it was even a few years ago. And work itself comes to be understood differently, as a series of discrete tasks rather than a lump exchange of time for money. Many Overemployed users sort of fell into multiple employment in the way that somebody might “fall” into an affair. It just seemed completely “natural” within the context of the digital economy. One worker told the Wall Street Journal that he was so mind-numbingly bored at his primary job – “it is just attending meetings and pretending to look busy,” he said – that the second job was, if nothing else, a way to fill up his time.
The employment attorney Alex Kostas argues that the current structure of work is deeply outdated. “Laws and contracts still approach the employer-employee relationship as if everyone still works on a factory floor, with clock-in and clock-out times, so you are essentially still being paid for your time as opposed to your output,” he told me by email. Clocking in only when you really needed to actually represented a far more rational approach to the workforce. “So a driven person with other interests often can carve out time in their day to work on passion projects or other interests, and still get their work done,” Kostas added.
Seen in this other way, all sorts of famous phenomena of contemporary life – “quiet quitting”, “the Great Resignation”, “the gig economy”, “permalance” – come to seem like different sides of the same coin. The company or union job to which you are loyal to for your entire career – and which rewards you in turn – is for many workers a legend from the dim past. “The old deal was loyalty in exchange for security, progression, and decent pensions,” says Alex McCann, the founder of two companies dedicated to rethinking traditional career advice. “That doesn’t exist anymore. So why should people keep pretending it does?”
In the new, and pervasive, paradigm the worker is self-determined. It’s understood that the employer is using the worker and the worker finds their way to use the employer in turn. Tim Butcher, the author of Creative Work Beyond Precocity, contends that this kind of polyamory is essential to a worker’s long-term well-being. “My argument is that as so much of what we call work is unmeaningful (see David Graeber’s Bullshit Jobs) that in order to find meaning in life and work we now need to navigate our careers very intentionally, in order to find meaning in them,” he told me by message.
And somewhat surprisingly, employers in many cases seem willing to tolerate this kind of infidelity so long as their workers are fundamentally productive and aren’t, for instance, working for a direct competitor. “When I talk to CHROs [Chief Human Resources Officers] about their side hustles, most seem fairly positive as long it doesn’t impact what you should be doing with your work contract,” says Andrew Spence, the founder of the HR innovator Glass Bead Consulting.
But if, for people who are on the side of workplace polyamory, it seems like just the thing that everybody is doing, it probably shouldn’t be underestimated the extent to which it rubs the old guard the wrong way. Earlier this year startup founder Suhail Doshi took to X – in a post that’s been seen 23 million times – to complain about a former employee of his who, he claimed, “works at 3-4 startups at the same time,” and encouraged his current employers to fire him. Like Appiah’s column in 2021, Doshi’s tweet produced a wildly divided reaction – the way people conceptualise work tends to speak very deeply to their class backgrounds and their moral sensibilities.
Workplace polyamory, even if it followed certain economic and technological trends, was also, for many, a moral red line. The job-jugglers who spoke to the Wall Street Journal in a 2021 article described a kind of adrenaline-rush in keeping their dual lives secret from one another. “I’ll wake up in the morning and I’ll be like ‘oh this is the day I’m gonna get found out,'” one said. But behind that fear was a belief that transgression was actually the path to freedom.
Buried in the scolds directed against workplace polyamory was a degree of hypocrisy. It’s completely standard for venture capitalists and entrepreneurs like Doshi to work on multiple projects at the same time. It seemed not to bother Appiah that, notwithstanding his advice encouraging one worker to rat the other out for double-dipping, he, according to his current résumé, has positions at five different institutions in addition to writing a column for the New York Times. For that matter, X, the platform on which Doshi’s post appeared, is owned by Elon Musk, who currently runs six companies each one in excess worth of $1 billion.
So what exactly was the standard that made it alright for any number of entrepreneurs or tech titans to work on an immense number of projects at the same time but for the white-collar workers who worked for them to get summarily fired if it turned out that they were trying to boost their own, much more modest, salaries? And much deeper than discussions of economic trends, or the ways that technology reshapes office life, there is the question of who gets to use who.
What probably is really going on is a mismatch between what we might call the “stakeholder” and the “shareholder” view of labour. The stakeholder view of labour is rooted in a social democratic view of the state and the public good – that everybody is doing their part to contribute to the whole. The tendency is to limit the number of hours in the work week, to assign workers to different unions, and with each union representing its own distinct social function, as part of a beautiful society-wise mosaic of the workforce.
The shareholder view has, essentially, no interest in any of that – its aim is just to make as much money as possible. The shareholder view belongs, of course, to unbridled capitalism, and – in the way that it tends to be exercised for the past half-century or so – it creates a bifurcation through the labour force, one that is felt every day at work. The capitalists serve the bottom line. They make as much money as they can, and their hours are immaterial – time is just a resource deployed to get the job done.
That philosophy is in contrast to the more bovine work regimen of the salaried workers, who still clock in and out, who don’t, after all, have capital invested and who, even if they’re working in a capitalist enterprise, tend to have a more stakeholder view of their own labour – they are working to feed their families and maybe for something or other about the nobility of labour – but, since they are not in the end working for the state or socially-invested enterprise, their job security is dependent ultimately on the caprices of capital, with the result that they can go down but not up.
At some point, sooner or later, this imbalance would be noticed and felt, and workers would do more to get their own back. They would, in a word, start to act like capitalists. If capitalists can journey predatorily over their different domains, closing up this division, selling that one, outsourcing the labour to China here and to Cambodia there, then workers can, in a far more limited way, do the same – they can shop employers and decide which of them is more worthy of their time and attention. If they’re good, they can keep juggling until they hit a pay day with one, say a significant promotion; or else they can just keep the multiple irons in the fire indefinitely, working for different companies at the same time, maybe forever, keeping themselves busy and stimulated, raking it in, hedging themselves against inevitable economic downturns, as opposed to just staying reflexively loyal to one exploitative company and waiting for a pension that doesn’t actually exist. It might be nice if employers and employees had career-long relationships and provided each other with security, but everybody knows that it doesn’t exist anymore. Capitalism – particularly shareholder capitalism – ruthlessly exploits employees. Nobody should be surprised if it becomes a two-way street.
[Further reading: Herzog’s nihilistic penguin is the right-wing Paddington Bear]
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