The Housing Trilemma

4 min readFeb 23, 2023

“It’s too fucking expensive here,” screams the Midwest transplant who just moved to New York.

They’re crashing at a friend’s place in East Village, in a makeshift bedroom that otherwise would’ve been a living room common area.

They scroll StreetEasy and the Listings Project, trying to find an apartment under $2000/mo. that meets the minimum bar of basic living conditions — and failing.

They have 10 days before the next subletter of the makeshift-bedroom-pullout-couch-room moves in, and they’re feeling the pressure.

A tradeoff has to be made.

Compromises are a fact of life, and we all know trilemmas well.

Right now, Midwest Transplant is facing the age-old problem: the housing trilemma.

Homes can only have two of three properties:

  • Cost: affordability of your monthly rent/mortgage
  • Location: proximity to things that you care about (e.g., the water, the office, friends, bars, restaurants, parks)
  • Quality of Home: desirable characteristics and features of your shelter (e.g., natural light, patio, space, amenities, modern appliances)

A perfect equilibrium that assures you’re hating some part of your life.

Hate being at home

This is the bucket that most New Yorkers find themselves in. Given a fixed housing budget, people are left with the choice of solving for location or for home quality.

“I didn’t move here to be inside all fucking day,” is something that Midwest Transplant may say. They moved here for the energy! The endless activities! The chance to feel young and alive!

Of course, they’re going to solve for location. Close to the subway, close to friends, close to all their favorite local haunts.

Who cares if the apartment doesn’t get any natural light? Midwest Transplant is out-and-about, living their best life.

But in the moments when MT finds themselves at home, they hate it. Turns out a 300-square-feet, 5th-floor-walk-up, pre-war, street-facing studio above the Rumpus Room isn’t the sanctuary away from the madness of New York that MT originally imagined.

And when MT is inevitably sick from riding the subway 3 times a day — going from pilates to work to happy hour to dinner to a show at Comedy Cellar — and ends up stuck inside for days on end, they realize that they cannot stand living there anymore.

Back to StreetEasy they go.

Hate where you are

Whether its the commute or your safety, if you solve for cost and home quality, you’ll going to be skimping on location.

That $1,500 1,200 square foot 2-bedroom 2-bath with a backyard in Canarsie looked awesome in theory, but MT is starting to regret the 40-minute ride on the L train to go climbing with their friends at Vital.

God forbid, MT has to go into their office for an in-person meeting. That’s 2-hours round trip with 3 transfers, and MT is not a podcast person.

Add in the fact that any Uber from Manhattan after midnight is $40+ without surge, and the price tag starts to slowly climb up.

Hate your bank account statements

OK, fuck it. You only live once. Time to get a place that you not only love but is also close to the things that you love as well.

Newly anointed as the most expensive city in the world, New York makes everyone absolutely and utterly broke.

If you’re already broke, what’s being a little more broke to you?

Until you splurge on a new construction penthouse in Brooklyn Heights and realize that your net worth was higher post-undergrad than it is now.

Forget maxing out your IRA, we ball.

In conclusion

While the examples I listed were neighborhods specific to New York, you can not only extrapolate this to any other city, but also zoom out into a more macro scale.

Post-covid life and remote work has shifted the housing trilemma to include cities, regions, and even countries in the scope of decision making.

Should you live in Cleveland, Ohio? How about Mexico City (please don’t)? Or should you move back in with your parents for maximum savings?

No matter what you pick, you’ll always end up being unhappy with some facet of it. That’s the trilemma, baby.




Product manager, DAO contributor, crypto enthusiast