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Screen captures of Kunal Gupta, CEO of Polar, in front of various Zoom backgrounds on Oct. 26, 2020.Fred Lum/The Globe and Mail

If there’s one giveaway that Kunal Gupta is not actually in New York, or Bali, or a rich person’s library – some of the various background scenes he chooses carefully before each meeting on Zoom – it is the strange thing that happens to his ears.

For some reason, computer pixels occasionally wrap around the appendages, making them look sharply pointed against the artificial skyscrapers or palm trees. It’s as if two small glimpses into the real world are hovering on either side of his head.

These tears in Mr. Gupta’s digital camouflage can feel tantalizing, since his real world is mysterious even to people who know him well. The founder and CEO of the Canadian ad-tech company Polar has been working from home since the beginning of the COVID-19 pandemic, but even close business associates have little sense of where he actually lives. Chris Lehman, a senior executive at a company called MiQ, one of Polar’s clients, recently vowed to get a screenshot if he ever saw into the physical room where Mr. Gupta was sitting.

The mystique is deliberate. Mr. Gupta considers the backgrounds a “hack” – coder talk for a clever way around a problem (the problem, in this case, being colleagues seeing into each other’s homes).

He is full of these hacks. Mr. Gupta has spent an uncommon amount of time thinking about every aspect of the work-from-home revolution currently ripping through the business world – because he is trying to make it permanent. His company of about 30 has severed all of its leases. His employees will never return to the office. Zoom is their office now.

I interviewed Polar employees, investors and clients about how they were managing exile from the familiar world of water coolers and cubicles – a change that is upending not only their lives, but everything from management philosophy to the shape of cities. What I heard back were ideas about community, loneliness and innovation.

A growing number of companies, from Facebook to Canada’s Shopify, are taking the pandemic as a cue to permanently diminish the role of physical offices. That will mean reinventing white-collar work, rather than just muddling through with kitchen tables and sweatpants, like we’ve all been doing since March.

At a time of uncertainty, Mr. Gupta spoke like a Jacobin about hauling vestiges of the past to the guillotine. He talked about using Polar as a “guinea pig” to change the way we work. He wanted to rename days of the week to encourage different kinds of creativity (goodbye Tuesday, hello “Flow Day"). There would be new ways of communicating and some old ones pulled off the trash-heap of history.

“Year Zero was my thinking,” he told me one day. “If you had a blank slate, what choices would you make? And I didn’t know what choices I would make. So that’s the experiment.”

Polar’s officeless experiment illustrates one of the defining questions of the pandemic era: Can businesses thrive when the fabric binding them together is digital? Can people? How does this work-from-home revolution actually play out on the ground? Where does the rhetoric ring true and where does it bump into hard reality?

Or, framed yet another way: Where is Kunal Gupta calling from?

The financial district is deserted. The weather is grey and muggy. There’s a dystopian, end-of-the-world feel in the air. It’s fitting, because I’m on my way to a graveyard for the office era.

Polar’s Toronto operation is – or was – housed in the gleaming, glass-and-granite Dynamic Funds Tower at Adelaide and Yonge streets in the heart of downtown Toronto. The company’s fifth-floor workspace was typical of late-period office design: low ceilings made of perforated white foam-board; fluorescent tube lighting; rows of desks with little plastic dividers; stale, buzzing air; a view of … other office towers.

It was here that Polar had spent every day doing what many tech companies, fundamentally, do: advertising. Mr. Gupta and Rahul Agarwal, now vice-president of product, co-founded the firm in 2007, making applications for the BlackBerry and iPhone (including The Globe’s first mobile app; the paper is still a client of Polar’s digital ad business, but a small one, according to Mr. Gupta).

Polar later shifted to building technology that promoted “native” ads – ads designed to look not like ads – before expanding into the profitable line of repurposing companies' glossy social-media posts for the homelier “open web.” Business is good: According to data provided by the company, revenue is up 107 per cent since January.

By late July, Polar was in its last week of occupancy in its natural corporate habitat and evidence of a chaotic departure was everywhere. A snake-pit of computer cables and dongles lay tangled on the floor, some marooned-looking keyboards were strewn on tables and a box of probably 200 AA Duracell batteries sat forlornly against a wall. Over each desk was a little pane of milky glass for employees to write technical notes on – “afraj,” “20% DoD,” “social” – which now had the melancholy look of Roman graffiti uncovered during an archaeological dig.

The New York office was abandoned in a similar Pompeiian rush. Belen Martinez, a business development manager at the company, is still waiting to retrieve a purse and sweater she left behind at the beginning of the lockdown.

At first, this exodus was imposed on Polar, the same way it was forced on every company by the onset of COVID-19. But making the move permanent was a choice driven by a cold financial calculus. “I don’t want to pay rent,” Mr. Gupta said, since rent constituted 6 per cent of Polar’s budget.

When he broke the news to his staff in May, some people were not “on the same page,” he said. Other employees described their reactions in blunter terms. Mr. Agarwal said he experienced the announcement as a “jolt.” “When we found out we were losing our office permanently, I thought, oh, shit.”

There was no longer any market for office furniture, so Polar encouraged employees to raid the place and pick it clean. The company would already be saving a pile of money by moving out – $400,000 a year.

Polar handed back possession to their landlord on July 31. Now the work of figuring out what came next could begin.

The last person to leave the office was a cleaner. He took a photo to prove his work there was done.

Rahul Agarwal looks nothing like his user photo. The digital thumbnail of Mr. Gupta’s genial long-time lieutenant screams “well-groomed young professional”: He’s wearing a blue button-up shirt, with gelled hair and a school-photo smile.

But here, in the shadowy light of Zoom, against the blank beige walls of his home office in Mississauga, Mr. Agarwal cuts a different figure – more like “college freshman behind on a term paper.” His hair is dishevelled, his T-shirt says GAP and below the threshold of the screen he’s wearing shorts.

It’s August, and Mr. Agarwal, like the company itself, is still muddling through. Working from home remains a bizarre aberration, with all the surprising discomforts and haphazard accommodations that entails.

Wardrobe issues are just the start. (“I haven’t put on a shirt in six months,” he said. “I’m actually worried that I’ve grown out of them.”) Mr. Agarwal can’t stop snacking. Even though he’s convinced himself that almonds and cashews are healthier than chips, he also declares, a little abashed, “I love bread.”

The codes of Zoom haven’t come any more naturally than dietary self-discipline. He still finds it distracting to see himself in the video box while he’s talking – “I’m looking at a mirror image of my face!” – especially when bad lighting makes it look like he’s in “witness-protection mode.”

Other difficulties are more serious. For example, the lack of people. Mr. Agarwal and his wife just had a baby daughter, their first kid, but he still misses the human connections he made around the office. Researchers call these “weak ties” – and they don’t mean that in a bad way. The casual relationships people form at work have been shown to hold the potential to make us happier and ward off loneliness.

There’s one developer at Polar in particular who’s a serious introvert, always hunkered down at his desk. But he’s also a film buff, forever recommending new movies at the lunch table. It was the one place where he came out of his shell. Mr. Agarwal hasn’t seen him in more than six months and he may never see him again.

“There are so many colleagues who are such interesting personalities,” he said. “But it’s so hard to make that deliberate move to message them and say, ‘Hey, want to chat?’ No, that would be weird.”

When people miss something unattainable, they will try to create a replica. For all their leader’s revolutionary rhetoric, workers at Polar spent the summer counterfeiting their ordinary professional lives using the debased coinage of the home office.

Belen Martinez has replaced her subway ride from Brooklyn to Manhattan with a fake commute. Most mornings, she takes long, circular walks before flipping open her laptop for the day, most recently through a historic, “brownstoney” part of Brooklyn. “That’s gonna be my new fake commute,” she said.

Ms. Martinez has also tried to recreate her mediocre midtown lunches at home. In late August she broke down and ordered delivery from her favourite weekday takeout place, which makes overpriced lunch bowls. More recently she made her own version of the dish twice in a single week.

Even her home office setup is getting closer to the real thing. Each Polar employee has an annual budget of $1,500 for supplies to help smooth the transition and Ms. Martinez just used it to buy a 17-inch computer monitor. It has been “life-changing,” she said, with a rueful laugh, because “that’s about all I got going on right now.”

This muddling-through phase was not exactly the future Mr. Gupta imagined for his company. He wasn’t merely trying to create a bad simulacrum of cubicle-land in his employees' apartments, which is roughly what he had in August. His ambitions were loftier than that. He wanted to change the basic structure of white-collar work. By October, Mr. Gupta had rolled out a half-dozen experiments to replace some aspect of the office, each aimed at a specific problem with working remotely.

“I think we need to create more space, cut more things,” he said one day in September.

To attack the loneliness problem, Mr. Gupta launched a daily “library” period, when employees could work “together” in a shared video call. The idea was to recreate the experience of going to the library with friends in university – not to talk, but for the comfort of working side by side with someone you knew. Mr. Gupta has so much confidence in the idea he bought the web domain “” (not to be confused with, no “the,” until recently occupied by an apparently pornographic Israeli website).

To solve the problem of making decisions from home – not being able to pop into the boss’s office to get a ruling on something – Mr. Gupta has started hosting twice-weekly “office hours” on Zoom, when any staff member can dial in and get face time with the CEO.

Soon, Mr. Gupta moved from acting like a college provost to acting like a power-mad bureaucrat in the French Revolution. He started renaming days of the week. Flow Day (formerly known as Tuesday) was when workers would be required to concentrate on a Polar project and the office-messaging app Slack would be strictly curtailed. Fridays would hereafter be known as “Somedays.” The idea is for Polarites to work on a personal project they’ve always said they’d get to “some day.” One of his employees planned to pursue a passion for prison reform, another for woodworking. It also meant everyone would have to work harder for the rest of the week.

Some of his colleagues are clearly skeptical of the boss’s tinkering. “Kunal has a lot of ideas and experiments that he tries out,” Mr. Agarwal said. “Some of them work; some don’t.”

The library concept has promise – nine people showed up on the first day – but some employees found it awkward because it’s scheduled around lunchtime and you can hear the background noise of people’s homes. By September, “Somedays” were still being treated as fail-safes for catching up on work at the end of the week rather than launch pads for personal growth.

Mr. Agarwal has been particularly critical of “Flow Days,” which are meant to encourage deep immersion in creative work, but also have the effect of shutting colleagues off from each other. Chit-chat, he believes, is a crucial part of building camaraderie, but since online messaging is limited, friendly banter is down.

Mr. Gupta sees that as an advantage. He’s skeptical of the purported social function of work in a way that only a boss could be. “I’m already responsible for paying you,” he said. “But your social life – I’m not sure I want to be responsible for that.”

Polar has fitfully attempted to recreate the social atmosphere of the office in its new digital domain. Mr. Agarwal started a weekly “lunch table” video-conference, where colleagues could eat and catch up. But it was disappointing. Participation was low and the group could only talk about one thing at a time on Zoom, unlike in person, where side conversations sprout up organically.

“I don’t think we have figured out how to replicate a physical work space, virtually,” Mr. Agarwal said. “There is no perfect tool yet.”

A few weeks ago, he cancelled the virtual lunch table.

Even a cheerful revolutionary such as Mr. Gupta has been forced to admit the ancien regime is dying hard. His experiments don’t solve every problem of remote work.

The company has waved goodbye to “water-cooler moments.” In the office era, two colleagues would run into each other at the coffee machine (like most modern offices, Polar didn’t actually have a water cooler) and talk about Donald Trump or the Raptors, but maybe also about that nagging bug in an important application. They might even solve it while the coffee was percolating. “That knowledge-sharing that happens?” Mr. Gupta said. “That’s disappeared. That’s disappeared.”

Maybe most important is the lost art of the conversation. Work problems that would ordinarily have been solved with a 30-second chat in person are now sweated out over a dozen wordy emails. “The quality of communication has plummeted,” he said.

Naturally, Mr. Gupta has a hack for the problems created by his hacks. He calls it the telephone. “I think we need to relearn how to use that,” he said. The other day, he phoned his head of Europe at 8 a.m. without warning. He sounded proud of the audacity.

Banishment from the office has also produced a few unalloyed goods at Polar, no hack needed. The company’s new policy of hiring from anywhere has bagged talented programmers and co-op students who live in Waterloo, Windsor and Montreal – all out of commuting distance from the old headquarters.

Current employees can also spread their wings in new ways, working from anywhere that has internet access. Ms. Martinez spent part of the pandemic summer living with her family in Miami, and this winter she plans to spend a month in Uruguay, where she was born. “I’ve been trying to train myself to work with as little as possible, so I can really just throw everything in a backpack,” she said

It bears noting that Polar has a few built-in advantages that allow it to escape the worst pitfalls of officelessness. First, the company is small. The logistics of managing a work force that has migrated online is easier when the work force is the size of two NBA rosters.

The second advantage is tenure. The average Polar employee has spent seven years at the company. A well-known 2013 study, published in the MIT Sloan Management Review, showed the importance of teaching new employees “how things are done around here” – a process of acculturation that will likely be more difficult without an office. But Polar employees already know how things are done around there (even if there’s no longer any “there” there).

The third ace in the company’s hand is cash, which gives it a margin for error in this massive work-from-home gamble. This summer’s Facebook ad boycott drove lots of business Polar’s way. “All of that has led us to be super-profitable and make lots of money,” Gupta said, with typical swagger.

As September wore on, the staff seemed to become more and more resigned to what was happening. As upsetting and strange as the past eight months have been, one of the lessons is surely how much we can get used to. Over the course of a century and a half, we got used to the office, with its stale coffee and burn-your-retinas lighting and buzzing air; now, much quicker, we’re getting used to the home office.

Living through a revolution has turned Mr. Agarwal’s mind to reflections on how humanity is wired. He used to find it jarring to roll out of bed and immediately start work, but now it’s the old routine of getting dressed up and rushing out the door that would feel alien. Said Mr. Agarwal, the newly minted philosopher: “Like everything, if the person does it for long enough, it just becomes second nature.”

Of course, resignation is not the same as acceptance, much less affection. In this revolution, Mr. Agarwal is more of a Girondin. The speed and violence of the change have left him out of sorts. “I miss the office a lot,” he said simply.

He misses the separation of work and home. Sometimes, these days, he gets carried away and hammers at his laptop until 7:30 at night. There’s no more natural breaker on the day; no ritual of laying down tools, packing up and leaving.

He misses the people above all: the ease of knocking on someone’s door for a chat, the crosstalk and movie recommendations and engineers coming out of their shells. He misses the not-quite-friends who used to fill out his social life, “the other colleagues who you meet at the lunch table and say, ‘Hey, how is your daughter?’”

Another lesson of the past eight months is that bosses and their employees can get used to different sorts of arrangements. For all of Mr. Gupta’s concern with “wellness” – he is a meditation teacher and sits on the foundation board of the Centre for Addiction and Mental Health – he evinced little concern for the psychological effects of untethering his workers from the workplace and each other. The death of happy hour, for example, leaves him cold.

“If you’re having drinks with colleagues after work, you’re probably complaining about your boss,” he said. “It’s toxic.”

Of course, as the Jacobins learned more than 200 years ago, revolutions are messy for leaders and followers alike. For evidence, look no further than Mr. Gupta’s own home office, incubator of so many utopian dreams.

During one of our interviews, I asked to see behind his Zoom background – that day, it was a luxury condo. Mr. Gupta clicked a button and the marble and glass were gone. I was confronted with a view of the same pale walls and hostage-video lighting everyone else has.

It turned out Mr. Gupta was calling from his parents' house in Mississauga, where he has lived since leaving New York at the beginning of the pandemic. The glamorous projections of Manhattan and Bali were pasting over an unglamorous reality of parental tech support and medical appointments.

“I’m a few minutes late,” he said during one call, “because my Mom asked me to do the dishes.”

Never had the gap between the ambitions of working from home and the reality looked starker. In months of furious experimentation, Polar showed where that gap can be bridged and where it yawns widest.

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