March 26, 2022

A Few Places I’m Bullish On

The pandemic “shook loose” a lot of people. Once their job or school was no longer tied to a physical location (or got tossed aside in the great resignation), a whole lot of people looked around and suddenly realized that they didn’t need to be exactly where they were, living exactly how they were.

Anybody who’s done it knows that commuting, especially by car, sucks our soul dry. And with our planet both literally and figuratively on fire, the environmental cost of shuttling millions of people back and forth each day starts to feel untenable as an organizing principle of our society.

Given the new reality of tomorrow, I’d bet against our 20th century suburban model. Here are the places I would bet on though, at least in my neck of the woods in the New York metro area:


It’s hard to say that the 6th most populous city in the United States is a hidden gem. But despite its size and history, Philly doesn’t always enter the conversation when we talk about where young talent and economic opportunity are migrating. While Austin, Nashville, or Miami might have better weather, Philadelphia is a proper, walkable city with functional mass transit and (relatively) affordable housing. Its position on the Acela corridor between NYC and DC makes it easily accessible to two of the nation’s most important centers of power, and the city is home to some of the best universities and museums in the world.


Though an order of magnitude smaller in population than Philly, a lot of the reasons to bet on both cities are the same: a great location between two massive anchors on the northeast corridor, lots of great educational institutions, and more affordable conditions than other trendy destinations. Providence is smaller and more car-dependent than either Boston or New York, but the city can be attractive for young families from either neighbor looking for a little more space while maintaining some of the benefits of urban living and easy access to the “big show.”

The Hudson Valley

Moving to a small Hudson Valley city is the new moving to the suburbs. For a generation of New Yorkers that are marrying later and having kids later — which combine to mean more time marinating in the joys of city life — it’s much more attractive to simulate a Brooklyn neighborhood in a place like Beacon, Newburgh, Kingston, or Hudson, than to get that white picket fence in a Boomer-generation suburb. The commutes from the former might be longer than the latter, but in an age of remote work, many more can tolerate that longer, but less frequent, train ride in exchange for the culture, nature, and affordability of these mini-cities.

The Catskills

For New Yorkers not looking to move full-time out of the city, there is a time-honored tradition/daydream of life-longers whose budget allows it: a little place outside the city. For the last few decades, the east end of Long Island, with the Hamptons out to Montauk, has become the destination for those with serious cash. But largely due to the generational wealth gap, most younger people are frozen out of this vacation region for the foreseeable future. Instead, they are looking north, where many of their grandparents (mine included) may have escaped the summer heat in the days before air conditioning: The Catskills. The rural, mountainous counties of Sullivan, Ulster, Greene, and Delaware offer incredible natural beauty and outdoor recreation, of course, but their relative affordability offer millennials the ability to actually get a foothold in ownership— and to touch grass instead of staring at a screen all day.

Always Bullish: New York City

All these places are wonderful, but New York is still the center of the action. This city is where the world comes to make and share great things, and despite our struggles in this century, from 9/11 to the financial crisis to the early epicenter of COVID, all happening against the background of the ever-present affordability crisis, it’s always been foolish to bet against New York. While I’m perennially bullish on this greatest of cities, I’m excited to see how our region, as a whole, evolves over the next generation.

About the Author

Ben Guttmann ran a marketing agency for a long time, now he teaches digital marketing at Baruch College, has a book coming out in 2023, and works with some cool folks on other projects in-between all of that. He writes about writes about how we experience a world shaped by technology and humanity – and how we can build a better one.

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