Remote Isn’t Working

Digital Suburbia and the Future of Cities

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Remote work promises freedom: from offices, from commutes, even from place itself. But that freedom may not be as free as it appears. Tyler Denk, the CEO of newsletter platform beehiiv, recently took to LinkedIn to extol its virtues. Six years after the pandemic rapidly accelerated the prevalence of remote work, it’s not hard to see why many love it: it cuts office expenses, it eliminates commuting time, it allows companies to hire the best people for the job wherever they live, and it increases productivity. For Denk personally, remote work has given him “lifestyle arbitrage,” allowing him to live a much richer life in Medellín, Colombia, with a private chef, a maid, and penthouse views. Denk said, “Fully remote over mandatory in-office is a hill I will die on.” Having worked remotely in various capacities over the years, I know the freedom and mobility it offers, too.

And yet, what looks like a triumph over place-bound work isn’t one: the remote work lifestyle depends entirely on people who cannot be remote at all.

Denk’s setup is extreme, but the underlying dynamic applies even to more modest remote work arrangements. While knowledge workers enjoy the comforts of home, their daily needs are met by an army of in-person workers: childcare providers watch the kids, HVAC technicians and landscapers maintain the house, logistics workers in warehouses facilitate the on-demand deliveries that show up on doorsteps. Even when remote workers step out to a local café, the people serving them are serving them there—in a fixed location that is optional for the knowledge worker but mandatory for the barista—on streets maintained and kept safe by a battalion of police, EMTs, sanitation workers, and utility technicians.

The freedom to be untethered from a specific place rests on a layer of people who remain very much tethered to it.

Indeed, only about 22% of the workforce can work remotely at least part of the time, with levels correlating directly with educational attainment. For the vast majority, remote work is aspirational—and mostly unattainable. That’s because mobility isn’t evenly distributed across work. The closer you are to abstraction and decision-making, the more mobile your work becomes; the closer you are to execution, the more place-bound it remains. Disparities like this aren’t new. The problem is failing to recognize who is supporting the hill remote-work die-hards are standing on: Denk’s “lifestyle arbitrage” depends on the tethered reality of local labor. His penthouse views come with blind spots.

These kinds of blind spots aren’t new.

In 2016, many people in dense, prosperous cities like New York, where I lived at the time, were genuinely shocked by the election results. The morning after, at the Montessori school I ran, there were more tears shed by parents than children. And yet, just weeks earlier, a visit to my in-laws in Northern Maryland had offered a very different view: in the working-class neighborhoods surrounding their gated community, Trump signs were everywhere. If you stayed within the confines of Manhattan, Brownstone Brooklyn, or other “gated” communities, you wouldn’t have seen much that challenged the prevailing view—you’d have had to go to Staten Island for that.

For coastal elitists like myself, entire categories of the American experience had been filtered out of view. Our picture of what America looked like was riddled with blind spots, and many of us missed the real divides emerging in our national life.

That divide mapped closely onto economic mobility. Some people could move toward opportunity, participating in a global economy that rewarded flexibility and abstraction, obtaining the best jobs and the best homes in the best cities. Many others were stuck in place, tied to a job, an underwater mortgage, or a town whose best days were long behind it.

The pandemic only accelerated this divide. For those in the knowledge economy, work grew even more detached from place as global mobility became a real option for many. Digital nomadism was no longer just a niche lifestyle choice but a way of life for an increasing number of people who saw the world’s cities as places to forage for opportunity. Meanwhile, for those whose work required physical presence, they were not only tethered to place, but exposed by it: to health risks, to rigid schedules, to the strains of a convulsing world. We briefly called them “essential workers,” a moment of clarity about interdependence that faded almost as quickly as it appeared.

What has emerged from all that was not only a shift in where people lived, but in how they experienced the world.

For knowledge workers, remote work has produced a kind of digital suburbia. The original suburbs offered an escape from the frictions of city life—crowding, noise, disorder—by separating daily life into zones connected by car. The digital version goes further. In digital suburbia, whether at the top of a penthouse or in a suburban subdivision, the home is the center of all aspects of daily life. Work, food, services, and entertainment are all mediated through and delivered to the home, minimizing the need to engage with the outside world at all. But this convenience still depends on a fully place-bound workforce to keep it running. The difference now is that, instead of you having to go to it, everything comes to you.

For those whose lives are fully immersed in digital suburbia, it’s easy to have blind spots about what and who makes it all possible.

Cities have been slow to adapt to this new reality. For some, the city now feels optional, flexible, even frictionless. For others, it remains rigid, expensive, and unforgiving. Cities are now caught in a simple bind: the people with the most freedom to leave no longer need to stay, while the people who make urban life possible can no longer afford to.

City leaders tend to treat these as separate problems. They’re not. In order for a city to be attractive to the highly mobile 20%, it must be affordable for the 80% who make that lifestyle possible. The highly mobile can take the lifestyle with them—to the mountains of Montana or Medellín, or to more mundane actual suburbs.

Many city leaders still struggle to accept the premise. Why would anyone give up the weather of Los Angeles or the amenities of New York for places like Austin or Charlotte? And yet, the Census data is clear: people continue to leave high-cost cities for cheaper ones. At the same time, many cities are still only tinkering around the edges of zoning reform even as rents reach record highs. School districts are hemorrhaging students as families escape to family-friendly housing in the suburbs. Municipal budgets are strained by rising costs, competing priorities, aging infrastructure, and unfunded pensions. Service cuts, higher taxes, and harder times appear to be the only paths forward—not exactly a compelling value proposition. Pleading for the wealthy to return to pay the bills, as New York Governor Kathy Hochul recently did, is not a solution.

By failing to provide upward mobility for the 80%, cities are forcing physical mobility: pricing out place-bound workers while giving the already-mobile fewer reasons to stay. What they are confronting is not that people can leave, but a widening gap between those who can choose where to live and those who are forced to move. Cities only work when the people who depend on them—and the people they depend on—can live within them. The problem isn’t just affordability or mobility; it’s that cities are responding to both without fully seeing either.

If cities can’t keep the people who make the physical world work, they won’t be able to keep those who inhabit the digital one.

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