I know a thing or two about moving around city to city, coast to coast to an exhaustive degree. Inside me is a constant war pulling me between planting roots and finding my forever city and never signing my name on a lease again. Two opposites and neither one ever wins.
Here’s a select city guide that may help you reflect on where you want to call “home” next.
Chicago
Chicago is large enough to never feel bored in but accessible enough to not feel intimidating. It’s populated, but it’s not 24/7 busy like New York. More approachable. Your money goes further here than on the coasts, and the city has a humble midwestern grit in the air that can stand on its own.
It has one of the largest art museums in the world: The Art Institute of Chicago, owned by the art university, School of the Art Institute of Chicago. Fun fact– the museum was originally created to display the works of the professors. Then it kept growing. It now sits directly below The Met as the second largest art museum in the U.S. (Ok, so it does have a few second places compared to New York…).
Chicago’s front yard is Lake Michigan. Waters as turquoise as the Caribbean. A lake so large with no end in sight it could very well be an ocean. The “L” is short for “Elevated” – their above-ground metro train system, and the nickname is part of the city’s identity. Chicagoans are friendly and open for small talk, like any good Midwesterner, but with a city this size, you can’t say hello to everyone you see.
Early to rise and early to bed. Shops, restaurants, bars close earlier than you think, so double check the hours. The art and music scene is alive – I remember my first weekend living in Chicago during college, I went to a house show in the basement of some garage band.
The winters are brutal. Lake effect is real, and the wind is insane. Polar vortexes don’t happen every winter, but they happen enough to remember. The summers make up for it. The festivals, the parades, the pop-ups. Everyone knows a Chicago summer is unlike any other.
If you like architecture, art, keeping within a budget, being near bodies of water, friendly faces with the big-city feel, parks at your fingertips, and can handle a hard dose of winter – this could be your city.
New York
New York, New York. She gets two. Manhattan and Brooklyn. (Sorry, can’t do all five boroughs – haven’t spent enough time in the others.)
If you want all four seasons. If you want to be in the middle of what’s next in every industry. If you don’t mind lugging heavy groceries up six flights or mystery liquids on the subway. If you want a city where it’s easy to make friends, find your niche, go back to school, advance your career, become an expert in something. If you hate driving and love public transportation and walkable streets. If you would wait in line around the block for a pop-up. If you want to be around humans being humans constantly. If you speak your mind, or want to learn how. If you have strong boundaries, or want to make them. This is your place.
I can’t tell you exactly what lifestyle New York will provide you because if you want it, New York has it. If you don’t know yet, New York will show you.
Manhattan
If you’re moving to New York for the first time, give Manhattan a go first. You may find it’s absolutely not for you. That’s the point. You need to figure that out.
Manhattan is intense, chaotic, insane, beautiful, curious, magical, sickening, healing. Every opposite in total harmony – with the irony being Manhattan is not really harmonious. If you can afford it, you can have a lifestyle where you rarely touch a doorknob. Or you could be managing with three jobs, running on fumes from gig to gig.
If you’ve grown up around trees, prepare to grieve them. No matter what anyone says, no matter how beautiful Central Park is – it is not a true nature fix. It’s just not. (Fully realizing that will rub some the wrong way. Thankfully this is my Substack.)
Just when you think you have an original thought: you do not. Which is sort of the magic of New York.
Prepare for shoulder to shoulder at Grand Central and a rush to find a spot on the train to Cold Spring on a hot sticky day when everyone and their mother has the same idea.
If you love art, there are thousands of communities to join. Galleries to see. If you love music, thousands of bands to listen to. If you love theater, thousands of plays to watch. If you love working out, thousands of classes to try – even if they cost you your right arm when you sign in. If you want multiple careers, this is the place. If you just faced heartbreak, this is the place to reinvent yourself. If you’re just out of college, an empty nester, recently retired, mid-career – New York is there. If you have the energy to put into New York, it will give back. You just have to free fall into the city’s pulse.
One thing New York lacks, in my opinion: a proper wellness scene. Health, sure. Workouts, sure. But genuine wellness – that’s LA territory.
New York can be so old New York and so cutting edge at the same time. It lives in polar opposites in total harmony.
Brooklyn
Oh, Brooklyn. Proximity to everything without the 12-month commitment to Manhattan’s worst bits.
Brooklyn is dive bars, wine bars, chicken coops in neighborhood gardens. Brooklyn has space, backyards at a more approachable cost for normal people, a kitchen to cook in, and Prospect Park. Tree-lined boulevards that make you forget you’re in New York entirely. Block parties, kids running around, Brooklynite parents with a laissez-faire approach to parenting. Bulk stores and fewer crowds. The possibility of having a sidewalk to yourself – that was my first win when moving from Manhattan to Brooklyn.
If you’re staying in New York for the foreseeable future, Brooklyn is a great place to settle into. Your neighborhood matters even more here – there are no cross trains. If you’re in Park Slope hoping to get to Greenpoint or Williamsburg, prepare for the 3 train, a bus, two transfers, and an hour and a half. But c’est la vie. That’s the life we pay for in Brooklyn.
Manhattan is great for firsts. Brooklyn is great for your restart.
Los Angeles
Wellness and vegan capital of the U.S. Entertainment capital. Everyone-climbing-for-something capital.
If you love the heat, palm trees, mountains and the beach, indoor/outdoor living, spending time in your car, making a plan to see friends on the other side of LA a month or two in advance – this could be your place. Los Angeles gets a bad rep from New Yorkers, and Angelenos don’t really hold the same grudge. They love New York. It’s a coastal war that’s quite one-sided. Californians are too chill for that.
LA is a drive from the Palm Springs desert, from slow and easy San Diego, from breathtaking Santa Barbara and quaint Ojai. There’s access to all types of nature and moving your body outdoors. Yoga, hiking, running, Pilates, cycling, surfing, swimming, climbing.
Because everything is so sprawling, I’ve heard it’s hard to move there without knowing anyone – simply because it’s hard to make new friends or commit to plans with new faces. It may be similar to New York where everyone is searching for the next best thing and treating people as disposable. That’s a cultural thing, and I don’t blame one city for it.
Generally, everyone is really nice. The sunshine puts everyone in a cheery mood. At the same time, you might find it hard to meet people vulnerably enough where they drop the facade.
LA’s vibe is rooted in visibility. Hollywood. Everything you do and see has a taste of it. If you’re intrigued by that, you could feel at home. If you’re put off by it, then the epicenter is not the place to be.
Minneapolis
Perfectly situated in the northern Midwest – brutally long winters but heavenly summers. Everyone and their mother has a cabin “Up North.”
I’m only speaking to the Minneapolis–St. Paul metro area in the State of Hockey. There is no such thing as bad weather here, just bad clothing. The culture mirrors Norway and Sweden – most natives still have relatives or cousins in Scandinavia.
Minneapolis prioritizes getting outdoors. Biking, running, yoga in the park. Most good Midwesterners will get up early on a weekend and be on the trails or bike paths by 8am. Lakes are literally in the city. You don’t have to drive out of town for a beach day. It may only be a few blocks from your house.
It has some of the greatest education and healthcare in the country. The world-renowned Mayo Clinic is only an hour and a half south in Rochester. You’re in great hands and amongst great minds.
Minneapolis is still pretty meat-and-potatoes. As crunchy and granola as it is, a burger and a brew is core to the identity. It’s not any sort of capital for vegans or plant-based people. Minneapolis is very climate conscious and certainly have vegan options, they haven’t latched onto the plant-based scene. They make up for their climate footprint by biking everywhere instead.
Music and arts are important, but often treated as side hobbies rather than full-time pursuits. There’s plenty of art markets during the summer, but you’ll find most of the sellers do this as a side hustle. The culture leans practical – medicine, law, education, real estate, sales, nonprofit work, or the trades. I graduated high school here as the only kid going to art school – that was quite the side eye. An even worse one when they heard I was taking a gap year before that. Ha.
Minnesota Nice is real. People care and rally around their communities. If you value outspoken liberal values and politics, this is a great place to be.
It’s home to many Fortune 500 companies. Target, Best Buy, 3M, General Mills, Land O’Lakes, Ecolab, Hormel Foods, UnitedHealth Group, Xcel Energy, US Bank. The list goes on. It’s a great place to land for recent grads, career pivoters, or anyone looking to accelerate. It’s not easy to recruit people to Minneapolis, so if you’re already here, you have a real advantage.
It’s also harder to build new community if you’re fresh off the plane. Not many Minnesotans leave. They stick around and keep their friends from school or college. They mirror the Scandinavian countries in this way too – warm but hard to break into.
If you love idyllic summers, a generous dose of nature and exercise, driving (because you will be), saying hi and smiling to strangers on the street, spending summers at someone’s cabin on the lake, picnics on the boat or on the hiking trail, and can handle five months of winter by embracing hockey, skiing, snowboarding, and copious amounts of hot chocolate – this could be your home.
San Francisco
San Francisco feels like a European city that ended up in California. It’s compact, walkable, hilly. The fog rolls in and the whole city changes mood in an hour. You can hike to a view of the Golden Gate Bridge before work and be in wine country by lunch on a Saturday.
It’s a tech city, yes, but underneath that, it’s bohemian. The Mission has some of the best food in the country. Dolores Park on a sunny day is the city’s version of a town square. The neighborhoods are wildly different from each other – foggy and quiet on the west side, sunny and buzzing in the east – and people are fiercely loyal to theirs.
San Francisco is unbelievably stunning. You won’t believe it, walking around. It’s cool and effortless. It’s chic. It’s charming. You could be biking across the Golden Gate at 7am and in the office by 9am.
But it’s also extremely expensive for what you get and that shapes your entire life there. The median home is over a million dollars. A one-bedroom costs what a mortgage would in most cities. And the city is transient – people cycle in and out constantly, which makes it exciting and a little lonely at the same time. Building deep community takes effort because half the people you meet could leave within a few years.
If you love walking everywhere, using public transportation, eating well, being near nature without leaving the city, being in awe of the vistas and sights of Northern California, living in the epicenter of tech and innovation, and don’t mind the cost of admission – San Francisco might be ringing your line. Just don’t bring a car.
London
London is New York’s older, more composed sibling. Same energy, better infrastructure. The Tube is clean, it runs on time, it makes sense.
London is one of the easiest cities in the world to be alone in. Nobody bothers you, nobody pities you, nobody asks why you’re eating by yourself. The city lets you be in it. You’ll wander into a market and lose hours without trying. You’ll sit in a pub alone and someone will talk to you without it feeling forced.
If you’re vegan, London might be the best city in the world for you. And I don’t mean a veggie burger on the menu. I mean full restaurants, artisan-level cooking, menus designed around plants with real imagination.
The neighborhoods feel like different cities. Notting Hill is cobalt blue market stalls and linen and Nepalese-made bags on Portobello Road. Shoreditch is street art and Brick Lane vintage.
London is expensive – not San Francisco expensive, but close. The trade-off is you don’t need a car, you can walk almost everywhere, and the city is built for daily life in a way most American cities aren’t. Groceries, transit, parks, pubs – it all works.
If you love being alone in a big city, eating extremely well, being steps from world-class universities, having the rest of Europe at your fingertips, and want a place that gives you space without making you feel small– London.
Paris
Paris is for the true romantic. Centuries of history and art surround you the moment you step outside.
The metro is easier to understand than the New York subway even if you don’t speak the language. It’s so interconnected you can get anywhere without thinking too hard about it. The buildings are capped; the blue sky is always there. Tree-lined boulevards, bicyclists, a boulangerie on every block.
If you can face the Parisians– their stares, the correction of your French, the unshakable confidence of someone who has been buying bread from the same bakery for thirty years– bon voyage. If you don’t make it to the boulangerie before work hours, be prepared for leftovers. When it’s gone, it’s gone. Return tomorrow on time.
The French aren’t in a rush. You sit at the café, you take your time, nobody is coming for your table. During the week, the French are sharp at business and not afraid of an argument in public. They see it as a sign of a strong relationship. If you can argue in front of friends or strangers and still sit down for dinner, the relationship is real.
In the summer, Paris will smell just as pungent as Brooklyn and the Lower East Side. No one warns you about that.
If you want to sit on the Seine or Canal Saint-Martin and drink wine with friends, read a book, go for runs with the most scenic views of your life. If you cherish art like it’s scripture. If you value style and fashion. If you can be a minimalist in a tiny apartment with eight windy staircases and no AC, Paris will give you everything.
Try one on. If it doesn't fit, try another.
Raye 💌
Comments
Nothing yet. Say the first thing.
Sign in to join the conversation.