Work is a Verb #30 - Urban Planners vs. CEOs: Who Has Better Data on Remote Work?


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Last week, the Bay Area published its 25-year infrastructure plan. Transit routes. Housing density. Commercial zoning. The kind of decisions you measure in concrete and steel, not the way the wind is blowing today.

Buried in Plan Bay Area 2050+ is a planning assumption that should make every RTO-mandating executive uncomfortable: remote work is permanent. Nearly 27% of the workforce will work from home (up from 11% in 2011) and demand for new office space is declining.

Meanwhile, 30% of companies have eliminated remote work entirely in 2026. Nearly half are mandating four or more days in the office. Instagram wants five. Home Depot wants five. Stellantis wants five.

Someone has it backwards...

Here's why I'd bet on the planners being right.


Urban planners can't afford to be wrong

You can't pivot a light rail line. You can't un-zone a neighborhood. When you're allocating billions in public infrastructure over 25 years, your models have to be built on observed behavior. Census data, commute patterns, real estate absorption rates, population migration. Not vibes. Not what the CEO prefers.

CEOs are making RTO decisions based on real estate sunk costs they don't want to write down, management philosophies built in a different era, and the fact that the people making these calls climbed the ladder under the old system. A University of Pittsburgh study found no significant improvement in financial performance after RTO mandates. But 80% of companies that mandated a return reported losing talent because of it.

The planners are modeling where people actually are. The CEOs are mandating where they wish people would be.

The Concrete Is Already Being Poured
And it's not just the Bay Area. Cities across the country are making the same bet with bulldozers, not memos.

New York City is converting 25 Water Street, a 1960s Wall Street office tower, into roughly 1,300 apartments in the largest office-to-residential conversion in U.S. history. Chicago approved $260 million for five downtown office-to-housing projects. Boston is offering 75% property tax abatements for 29 years to developers who convert offices to apartments. Washington, D.C. wants to add 15,000 new residents to its downtown by 2028, in buildings that used to hold commuters.

For the first time in 25 years, more office space is being removed from the U.S. market than added. Moody's projects national office vacancy will peak at 24% in 2026. Google is subleasing over a million square feet. Kickstarter put its headquarters on the market.

Meanwhile, Tulsa has paid 3,400 remote workers $10,000 each to relocate. Rochester offers $19,000. Italian villages in Calabria offer up to EUR 28,000. Cities and countries are competing for remote talent the way they used to compete for corporate headquarters. Because the asset isn't the building anymore. It's the people.

When transit agencies, city planners, developers, and entire national governments are restructuring around the permanence of remote work, leaders mandating RTO are either being illogical or dishonest about their motives.

CEOs may be in charge of how we work next quarter, but the long term direction is clear.

🎯 WORTH YOUR TIME

The Business Case for Belonging and Connection at Work

Loneliness at work costs $13,300 per employee per year. Dr. Tracy Brower rounds up the research on why belonging drives performance, retention, and even physical health. Her solutions are leader and policy focused and well worth a read for those with an interest in workplace culture. The article also includes links to the academic studies.

I would add that work is not the only (or even best) place where belonging can happen. The commute you eliminated gave you 4+ hours a week to build connection in your actual community. Use it!

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Company Spotlight

Tremendous logo Tremendous

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FinTech • 130 employees • New York, NY (Remote)


Tremendous makes it fast, free, and flexible to send payouts to people in over 230 countries. Whether it's research compensation, marketing incentives, or employee recognition, their platform handles billions in payments while keeping the experience simple for senders and recipients alike. Founded in 2010 as part of Y Combinator's Winter 2011 batch, Tremendous has grown without outside investors. The team spans multiple continents and operates async-first: almost all communication happens through Slack, GitHub, and Notion, with detailed documentation that makes onboarding faster and scaling easier. Synchronous collaboration happens during a daily overlap window, but meetings are the exception, not the rule.


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Working remotely—but never alone,

Jim


600 1st Ave, Ste 330 PMB 92768, Seattle, WA 98104-2246

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