Why I Moved to a Small City After Living in Los Angeles, San Francisco, New York City & Chicago

I moved to a small city in southeast Wisconsin because I wanted a place to live that was close to family, close to nature, and affordable. I value natural beauty, financial independence, and proximity to family. I currently don’t care as much about shopping, dining out, in-person job opportunities, and nightlife. It’s the “30 years old, recently married, lucky enough to be able to work remote, depressed by the real estate prices in [choose your big city]” change that lots of people go through. Here’s how it all went down. 

My winding journey to a small city 

I spent most of the first 31 years of my life living in big cities. I lived in LA, SF, NYC, Chicago, and Tel Aviv. They each have their charms. But none of them checked all my boxes. 

While living in LA, my (now) wife and I got serious about finding a place to live that we loved. We didn’t just want a place with the most to do or the best jobs — we fantasized about bucolic lives full of nature walks, star gazing, affordable home ownership, and growing vegetables in our own garden. 

So we moved to Madison, WI and promptly broke up. We weren’t ready as individuals or a couple to handle the move. 

Sad. Awful. I listened to a lot of dark Sufjan Stevens songs. 

We moved to opposite coasts for a while. Then we got back together. 

Joy! Love! A million doves erupting in flight, etc. 

We moved to San Francisco together and restarted our life journey. We began big city hopping. After 6 months in  SF to NYC. While there we got married and once again started fantasizing about bucolic lives full of nature walks, star gazing, affordable home ownership, and growing vegetables in our own garden. 

So we of course moved to a luxury high rise apartment in the most touristy part of Chicago. I’m actually impressed with how off track we got from our original goal. 

Instead of being close to nature, we were near an overly manicured city park that spanned a multilane highway and sat in the shadows of massive skyscrapers. Instead of a backyard garden we had a 600 sq foot box of an apartment in a high rise building that overlooked an alley. Instead of a slower pace of life we dodged pedestrians and Ubers while speed-walking to work and shouting at each other over the din of the L train. 

We thought Chicago would be a middle ground that was cheaper and chiller than a lot of other big cities. And it was in some ways. It wasn’t all bad. I made a great friend, and I played in some of the best pickup basketball games of my life. Still, a few months in, I was depressed. 

My wife wasn’t depressed, but she wasn’t loving the city either. So we decided to find a subletter and get out. It was time to give the small city life a chance. 

We lived in my in-laws basement in a small town near Fond Du Lac, Wisconsin, for a couple of months. Then my wife and I bought our first house together in Sheboygan, WI. 

This round of Wisconsin living is going much better, mostly because my relationship didn’t immediately end, but also because I like where I live. 

This house in Sheboygan is the first place I’d lived as an adult that has just about everything I’ve always wanted:

  • low cost of living
  • no roommates
  • no shared walls
  • easy access to gorgeous nature
  • good paying jobs nearby if needed
  • quiet and spacious living quarters
  • entertainment and restaurants within reasonable walking/biking distance (though I’ll admit we usually drive)

My neighborhood from above.

There are tradeoffs, of course. We had to buy a car when we moved. We can’t see world class broadway shows or eat any cuisine we want at any time of day. The quality of my basketball games is not quite as good. It gets very cold for a few months every year. 

But we still love it, warts and all. 

What I love about living in a small city 

As a quick meta point, I like the fact that small cities even exist. I always had a binary view of life in the US — there were big cities and small towns. Big cities had jobs and cool people and fun things to do, and small towns had farms and closed-minded people and nothing to do. 

The idea of a small city (population 5k to 50k) with a relatively diverse population, good jobs, cheap housing, a relaxed vibe, and plenty to do never really occurred to me. 

There are a few key things that make small city life special to me. 

Small cities are more affordable than big cities

There are always exceptions, but in my experience small city life has been way cheaper than big city life. Here’s what I’ve paid for housing over the last 10 years. 

  • Rent in Los Angeles for a tiny room in a roach filled building with thin walls and 2 stressful roommates sharing the same space — $700/month 
  • Rent in SF for small 1 bedroom with paper thin walls and active drug deals going on in lobby — $2500/month
  • Rent in NYC for 400 sq foot studio — $2250/month. 
  • Rent in Chicago for 600 sq foot 1 bedrom in a busy tourist section with old appliances, a “view” of the sides of a bunch of nondescript buildings, and the constant din of lakeshore drive + apartment air conditioners every time we opened our window — $1860/month. 
  • Mortgage on 2000 sq foot house in a nice part of Sheboygan, walking distance to lake and woods, 10 min bike ride to sandy beach, 15-30 minute drive to several gorgeous state parks, kind neighbors who let you borrow their ladder if you need one, and a backyard big enough that your dogs can do all out sprints for 30 yards while playing fetch— $750/month on a 30 year mortgage. 

One of those is not like the other. We do owe 160k to the bank before the house is officially ours, but coming up with $750/month should be doable for the foreseeable future. 

This is not just my isolated case. On the whole, small cities are cheaper, especially if you care about buying a home. 

Owning a nice home in a great area isn’t everyone’s dream, but it’s almost everyone’s dream. One recent study showed 89% of millennials want to own a home. Sadly, just 4.9% of them said they’d do so in the next year. Could it be because most of them want to live in big cities?

Small cities let you build your own nature adventure 

If you can find areas that the tech algorithms/cool kids/media all say are not desirable, and uncover aspects of them that make them highly desirable to you, you’ve discovered an inefficiency in your own personal housing market. 

You want to find the sweet spot between a place that is cheap because others have decided it’s not a great place but that still has a lot about it that genuinely excites you. The genuine part is important. You can’t just move to the middle of nowhere Nebraska and expect to love it cause it’s cheap. 

I value easy access to long walks in nature, especially forests. I also love walking along bodies of water, be it an ocean or lake. So by identifying a cheap place that had all that, I was gaming the system. 

But it should be noted that you can’t necessarily find your dream place with cursory internet searches (which I’ve totally tried to do.)

According to google maps, my immediate neighborhood doesn’t have much greenery. The circled area just down the street from me looks like a bunch of nothing. Might as well be a big parking lot. 

But here’s what that area actually looks like:

Sure, it’s a little different in the winter, but me and my pups still think it’s great. Winter bonuses: even more solitude and no bugs.

It’s a nature preserve with trails. Google Maps is awesome, but it needs to step its game up in this regard.

To be fair to the inner-city dwellers, I am about a half mile from the closest grocery store, and there are no sidewalks for most of that route. I miss the ease of getting actual things done by foot, not just walking for pleasure.

That said, I’m not mad that I can no longer walk to the post office (and wait in a 30 min line full of angry people), or to get an (overpriced) drink, or to check out a local jazz club (literally never happened).

Small cities still have plenty to do 

I’ve waxed poetic about all the nature in my particular small city, but there is plenty beyond that. 

We can bike downtown and eat amazing Italian food from a restaurant run by a chef who was a semifinalist for the James Beard Award. This particular spot was also one of the first certified Neopolitian pizza places in the country. I don’t know what that means but it seems impressive! The town has plenty of other great restaurant options. 

We can also check out a gorgeous, free art museum, and there is another opening soon. 

An exhibit by Mark Baum at the John Michael Kohler Arts Center.
A new museum in Sheboygan opening soon.

We get to see live music all summer from bands across the country (when there is not a pandemic).

There is a very cool children’s museum that I once showed up to alone and had to awkwardly explain to a skeptical, teenage front desk employee that I was there to meet friends with kids. 

There’s a great library, several artsy design stores, funky and delicious coffee shops, and even a freaking surf shop. We’re the lake surfing capital of the country, people!

My city is not going to keep an energetic and extraverted 20-something engaged at all times. But in a few years, when those folks look at their dwindling savings account and wonder if all the $37 big city brunches have been worth it, they might decide to sacrificing optionality and see if they can learn to love what a more affordable place has to offer.

You can get a good job in a small city 

If you want to have your pick of in-person jobs across any possible industry, you need to be in a big city. If you are willing to narrow your options, there are plenty of places hiring in small cities across the country. 

My area has several thriving employers, including international brands like Kohler Company. My wife and I are lucky to have good remote jobs with companies based on the east coast, but we expect we’d be able to find local jobs if we needed them. 

With the post-pandemic shift toward normalizing remote work, small cities look all the better. Why spend a full week per year sitting in LA traffic while living in a gross little apartment with a roommate who constantly complains about his job, if you can avoid it? 

You don’t have to live in a small city in the middle of nowhere 

I live an hour from Milwaukee and an hour from Green Bay. I’m 2 hours from Chicago. If I need a big city fix, I can get it. 

Small city living does not imply isolation, boredom, and disconnectedness. There are interesting, thriving small cities near universities and major hospitals and pro sports teams and anything else you could ever want. 

It’s often faster to drive to the Milwaukee airport (60 mile drive) to pick up an incoming friend or family member than it was to get someone from LAX when I lived in Studio City (25 mile drive). 

I’m a 4 hour flight from my family in LA. I’m about a 1.5 hour flight from my sister in Kansas City and my friends in NYC. I’m a 4 hour drive from my brother in Michigan.

You can find a small city with really cool people

Some people think that leaving a big city means you will end up surrounded by boring, unmotivated, one-dimensional, non-diverse people. That doesn’t have to be the case. Small cities have been growing more diverse, and if you look for one on the periphery of big metro area or University you’ll find tons of interesting people. We’ve met cool people through yoga, sports, work, and random neighborly interactions.

I should also note that I’m lucky that my wife’s extended family lives in our area, and that we could also re-connect with my wife’s friends in the area. It’s a huge reason we decided to live where we do. Having friends and family nearby makes a move about a million times easier (see, again, our Madison disaster.)

It’s not all perfect in a small city 

I’m not totally drunk on the small city kool aid. There are certainly things I’m giving up and things that I miss about big city life.

Big cities have more options

Big cities generally have the best schools, the best hospitals, the best entertainment, the best food, the best recreational athletics, and the best chances for making new friends as a young adult.

If I could have bought my exact house in a nice section of Los Angeles, CA, I probably would have. LA has fun stuff to do and open minded people and pretty amazing weather year round and access to incredible nature. I mean, I grew up in an LA suburb, so I know how great it can be. 

My California coast fantasy breaks down when you consider cost of living. I don’t want to wear a suit everyday, or go to grad school, or become a software engineer, or work long hours every day at a job I hate just so I can eke out some time doing fun stuff for a couple hours every weekend. 

I don’t have kids yet, so school quality wasn’t really a non-factor in our decision making. Maybe that will come back to bite us. The ratings aren’t that great in our area. But we’re willing to cross that bridge when we come to it. My wife and I are both products of public school systems and we think we turned out okay. 

There are big cities with good public transportation

It’s rare to have a small city with first rate public transportation, so you’ll want a car if you become a small city dweller. That comes with headaches and costs. 

Though the car life has pluses, too. There have been plenty of times when my wife and I were taking the train back from LaGuardia late at night, tired & hungry, only to get stuck on a cold platform, waiting on a train that was 30 minutes late, praying the rats wouldn’t band together to push us into the third rail so they could feast on our electrified carcasses. 

A small city might have all you need 

If you move to a small city, you have to be okay with some people not getting it at first. You have to learn to love the restaurants and stores you have instead of pining for the hippest options. You have to be willing to go on walks without sidewalks, drive long distances to go to Costco, and work a bit harder to find friends that share your interests. 

On the flip side, moving to a small city means you can own a nice home near a immaculate nature without selling your soul. You can see the stars. You can forget what traffic even means.

I even found a fun basketball league. I wouldn’t go as far as the man at the front desk of my gym, who told me, with a straight face, that Sheboygan was “the basketball capital of the world,” but the league has good players. 

Small city life is not for everyone, but I think it’s at least worth trying out if you’re on the fence about where you want to live.


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