The Chicago to Winston move: how it’s going eight months in

TL;DR—The Chicago to Winston move has been exactly what we wanted and more. Even the bumps have been welcome bumps. Cause what’s life without a bit of turbulence?! 

Disclaimers

One: I’ve been to all fifty states and Puerto Rico, and twenty-one countries. Chicago is a top-tier city and hands down, the best major US city and I will rap-battle anyone who says differently. Any negative remark of mine about the city of big shoulders, here or elsewhere, is not an anti-Chicago remark. It’s a reflection of who we are and where we are in life. We don’t want to live in any major city. Sure, she has her issues and her Chicago-specific issues but she will always be my identity, my pride, my number one. My Instagram Story is a Chicago-porn channel with some home reno, cleaning, women rule men drool, and Winston adventures tossed in. I am an unpaid employee of the Chicago tourism office. I don’t want to live there but I want you to live there. Or at least visit. She’ll hook you, what with her lake breeze, grid system, Brown Line, delicious calories, friendly inhabitants, breathtaking architecture, and pervasive inclusiveness.

Two: I understand how annoying it is when people move somewhere and then all they do is talk about what they miss and complain how much better ______ was where they came from. “There’s the door…” “Why’d you move here?” “Stop trying to make here like ______” “We’re full!” are common responses, especially in the cesspool that social media can be. I also understand how human and normal it is to compare a new chapter to an old chapter, especially if the latter was your entire life and if the differences are many and stark. There is a definite friction in Winston amongst long-timers and transplants on this topic. I’ve made a cognizant effort to not be “that person,” choosing to keep most of my comparisons of the positive nature. That said, Chicago summers, public transit, and food options are better than Winston, and those opinions may creep into conversation. That doesn’t mean I don’t love Winston nor that I want to go back to Chicago. I’ve happily traded oodles of X’s for oodles of Y’s. You’ll see many ways Winston is better than Chicago below. I’m uber sensitive about anyone side-eyeing Chicago. I get it. But now on the other side, I also get the side-eye. I’m more empathetic and understanding to both sides, and isn’t that what we should all strive for as humans?

Three: Much of what I epouse as loves in our new life, I could’ve had, done, experienced in Chicago. In some cases, easier and/or better. But I wasn’t. And I had no excitement to have, do, or experience in Chicago. We needed a restart. Whereas my Midwestern default became the couch, my Southeast default is Let’s go!

With that said…

Status: Squeeeeeeeee!

In my May “We’re moving!” post, I wrote: “We’ll be using this next year? to see if we like the state and to see if we like the various cities. If yes and yes, we’ll buy? Lots of question marks. Which is exhilarating.” LOLOLOLOL. We came here sight unseen and eight months in, we’ve seen all we need to see.

“Various cities”: we’ve been to one other city (Boone) and it was for leaf-peeping not home-peeping.

“Next year”: we started looking at homes immediately upon our July arrival, scouring Redfin, visiting open houses, and planting “Keep your eyes open” seeds in neighbors. September, we met with a realtor. December, we put in an offer. January, we closed.

We’ve fallen in squeeeee with Winston. I thought we’d road trip to Asheville, Raleigh Durham, Wilmington, Lake Norman to drive the streets, envision our lives, compare and contrast. But we’ve been so calendar-full and haven’t felt the need to explore elsewhere, for fun or for recon (though I can’t wait for road trip and maybe train trip dalliances). Someone I met perfectly monikered Winston a big little city. The perks of big—activities, culture, diversity, resources, shopping, dining, healthcare—and the perks of little—no traffic, no horns, everything within a fifteen minute drive, easy and inexpensive parking, property taxes that aren’t the highest in the country (looking at you Illinois), and housing prices that allow us to buy a home we love in an area we love.

We’ve fallen in squeeeee with West Salem. After living here for a bit, our “willing to live in” radius went from Washington Park, Ardmore, West End, and West Salem to West Salem. Validation for the research we did pre-move on both city and neighborhood. I don’t think there’s a Camel City area that checks more of our boxes —

• Walkable (sidewalks, businesses, non-death hills)
• Diversity (of homes, of people)
• Progressive, inclusive, liberal
• Craftsman, bungalow, colonial homes
• Subarus (owners tend to align with us politically, ethically, morally)
• Parks
• Tree- and grass-lined streets
• Mix of historic and new
• Character (no cookie cutter subdivisions or strip malls)
• Cute
• An active neighborhood association and overall community engagement
• Easy parking
• Good proximity to highway, downtown, grocery store, gym, and the majority of our adulting people (mechanic; doctor; dentist, etc.)
• Feels like a neighborhood
• Room for and evidence of growth

The Winston-Salem Journal article Find connections, convenience and creativity in downtown’s walkable West Salem neighborhood does a wonderful job identifying why we feel at home here—”I’ve come to believe that walkability is one of the most powerful tools we have to build social capital.” In fact too wonderful. The article came out in September, at the height of our housing search—Shhhhhhhh. Let us find our gem and then you can spread the West Salem gospel. From what we’ve gleaned, West Salem has not always been a “desirable” real estate area but that it’s climbing its way into conversations that include the more toney neighborhoods of Buena Vista, Ardmore, and West End.

In 2005, the West Salem Historic District was listed on the National Register of Historic Places.

Within a seven minute walk of us —

Cobblestone Farmer’s Market is every Saturday, year-round. Salem Bottleworks is a converted Coca-Cola bottling factory that now houses a pizzeria, ramen shop, and bakery, with tons of additional space whose future is excitingly TBD. Old Salem is an 18th-century Moravian town brought to life through costumed interpreters, preserved buildings, gardens, and working trades. Truist Stadium, home to the minor league baseball team, connects to West Salem via a new pedestrian bridge. Camino, ByGood, and Lot 63 are cozy coffeehouses. For adult beverages, there’s low-key West Salem Public House and Easytalk. There’s a yoga studio and a BBQ restaurant. The Strollway offers a scenic 1.2-mile route linking downtown to the area, and connects to the Salem Creek Greenway, which extends five miles and ties into a larger 27-mile loop including the hiker and biker’s dream, Salem Lake. A forest preserve is on my regular walk route. Granville Park and Washington Park offer tennis, pickleball, basketball, softball, doggy areas, and picnic spots. Two corner grocery stores have transformed into a charming Airbnb and hotel. Visit Winston-Salem, the city’s tourism office, and MUSE, the soon to be opened Winston Salem history museum, reside here, as do Carolina University and Salem College, the oldest women’s college in the US.

Shrinking our boundaries to this 2,000 resident pocket made the search more challenging but Life of Yes℠, on brand, we were optimism-heavy, and unlike last time we bought, when we had the most stressful two months to find a place, this time, we were in the driver’s seat, with time, funds from our condo sale, a rental property we adored, and a “Let’s not settle” attitude. And vroom, vroom!, it paid off.

We knew we missed the affordable housing boat in Asheville and Charlotte. We were unpleasantly surprised at housing prices in Raleigh Durham. Winston feels like the last big “affordable” North Carolina city. So we felt Phew! Let’s find something before we miss the Winston boat. Of course, it’s all relative. Locals say how much housing has increased. Chicago compared to San Diego, NYC, Boston, DC, LA is affordable. But we’re at a stage in life when an affordable big little city is more attractive than an affordable big city.

Just like when we temp-moved to Chattanooga to test out living elsewhere, we got the same loved ones reaction when we Winston-Salem’ed—Where?! Why?! Chatt and Winston were not on the radars of most of our people. Not in a throwing shade sense; in a small city, unfamiliar area, miles from home sense. But now, not only do they know about these two best of both worlds spots, it appears many others do as well. Good Housekeeping inlcuded Winston in 23 Unexpected City Vacations to Add to Your Travel Bucket List. According to the Chamber in a 2024 article, “population growth in Winston-Salem exceeds the national average. Over the past five years, Winston-Salem’s population has increased by 3.8%, compared to 1.9% growth nationally.” With zero data and just a feeling, I bet that’s gone up in the past two years. Seemingly every third person I meet is recently from elsewhere—the Long Island to Winston pipeline is real. On the regular, there’s a story on Winston’s encouraging economic climate, ideal retirement ingredients, revitalized downtown, and chef’s kiss quality of life.

In recent rankings, Winston has ranked high in lists such as —

• City for Small Business Growth
• Most Affordable Downtown in the U.S.
• Best State for Business
• Best City for First-Time Homebuyers
• Public HBCUs

We have that “just in time” sentiment in regards to city and neighborhood, as outsiders discover the delights. While we’re still learning the ropes—how exactly does Bulk Pickup work and what is the best Cookout shake?—we’re so glad to be insider-outsiders. With a North Carolina license plate, driver’s license, voting record, and property deed to prove it.

Why Winston?! 

“It’s slower, easier, quieter, cheaper, and warmer” is our standard quick response when asked “Why Winston?!” People are especially intrigued when they hear we didn’t move here for a job or for school, and that we could’ve moved anywhere.

Below are a few slower, easier, quieter, cheaper, and warmer examples. I could wax on oodles more.

Slower —

When at a red light, there’s what I’ve come to term the Winston Delay.

The light turns green, five to seven seconds pass, and then the first car starts moving. In Chicago, if you’re not halfway through the intersection by the time the light turns, consider yourself honked and a curse put upon your family. While a variety of Winston driving irks me and I wholeheartedly deem myself in the right, this one? This one, I remind myself to relax. To embrace how locals do it. To let go of past chapter proclivities. To say, “What’s the hurry?”

I have honked once since swapping 60622 for 27101, and they were fully on their phone and not ever moving save for my nudge. Justified honk.

But overall, honk hand has disappeared.

Easier —

There are so many events I wouldn’t have gone to in Chicago that I attended here because here, all my excuses and hurdles were removed. You know how it is. It’s the end of the day. It’s raining. You’re on the couch. Netflix keeps auto-playing episode after episode. You’ve removed your pants. Now you want me to put pants back on and people again?! In Winston, I do. Cause the event is nine minutes away by car. Zero traffic. Free, easy parking right in front. Or the event is nine minutes away by sauntering feet. Past fig trees and Black Lives Matter bungalows. To a small business you’re happy to support.

The downtown library has two free parking lots. Tons of free street parking. The street parking that isn’t free is cheap. I’ve never parked anywhere but right outside the front doors or in its garage. If I want to drive to Chicago’s Harold Washington Library, I should leave in April to get there in June. If there is any street parking, it’s $250 for three minutes*. But there won’t be. So go ahead and find a garage spot. The closest one is three blocks away; most are four, six, eight blocks away. Prices range from $8 to $60. Of course, any true Chicagoan wouldn’t be driving to the library. You’d be taking the train or bus, biking, or walking. Which are wonderful options to have and options I miss having. But sometimes you want the path of least resistance and to get somewhere without being sweaty or having to give up half a day for travel.

*Slightttt exaggeration. But it feels $250.

Our first weekend in Winston, we treated ourselves to Friday night dinner. We prepared ourselves for the worst. The traffic. The parking. The wait. The cost. No traffic; door to door in seven minutes. Free parking spot right in front of the restaurant. No wait. A $27 tab.

Quieter —

Chicago has about 2.7 million residents, while Winston-Salem about 0.26 million. I wouldn’t call the latter sleepy. But there have been times I’ve wondered if the City imposed a lockdown I wasn’t aware of. Like, where is everyone?!

Birds chirp in Chicago. I hear them more here.

Trees rustle in Chicago. I hear them more here.

The breeze whispers in Chicago. I hear it more here.

The noise I want is louder; the noise I don’t is softer.

Cheaper —

I’ve talked about housing. That’s the main cheaper we care about.

Gas and eating out are cheaper. Most other things are similar in price to Chicago. But where it matters (to us), check.

Warmer —

The number of people who’ve laughed at and been horrified by our outfits is uncountable at this point. Jackets? Never. Sandals and shorts? Always. “I’m from Chicago. This is tropical” has been explained repeatedly. Genuine concern left the body of one woman at the end of a February event as I mentioned I was going to Birkenstock walk home (twenty-five minutes). Mortified, “But your toes…” she clutched her pearls. Growing up in Chicagoland, college in Boston, adulthood in Chicago, my toes have never touched February air. If it’s thirty or above—They. Are. Breathing.

I’m also not used to such an array of blooming so early in the year. Going to our gym is like a trip to the botanical gardens. I spandex-snapped photos of at least eight different types of flowers on the Y’s grounds. All over town, trees are tree’ing and I’m like Japan and DC cherry blossoms, what?! No need. I’ll see twenty on my drive to Publix.

Speaking of…

Random Delights & Surprises

Jewel and Mariano’s are fine. I didn’t dislike them. But nothing made me engage in a photoshoot in their bakeries nor text aisle-wandering Best Friend “Come here!” so I could show him the source of my joy. On your birthday at Publix, you get to treat yourself to ice cream or to a bar cake, of any flavor. From carrot cake to cookies & cream, red velvet to hazelnut crunch, I was in heaven. Free and options?! The cashier greeted me with, “It’s your birthday, isn’t it?” What, did the cradled pastry, ear to ear grin, and springy step give it away? Publix’ made to order sandwiches, which we term Pub Subs, are delicious, and the fact that they have a vegan option; Best Friend heaven. While Chicago grocery BOGO sales were infrequent and never items I really wanted, Publix BOGOs are weekly and exactly what I want (Pretzel bites! Soup! Bagged salad!). The employees all graduated valedictorian from Friendly University.

Harris Teeter as a grocery store name makes me giggle. Every time.

Trader Joe’s not only exists here, it’s seven minutes away. And the parking lot isn’t a death-maze! It’s the only normal TJ’s parking lot I’ve ever experienced (though I hear you’re getting one, Chicago! Of course, right by our condo…A dream finally realized, eight months too late).

Lidl! Our first experience with Lidl was right before boarding a car-ferry in Scotland. We had never heard of it, so we thought it an exotic Scottish store. Then we went to Germany and lo and behold! Lidl! (We learned, its birthplace.) So we thought it an exotic European store. Then we moved to Winston. TWO LIDLS! What is our exotic good fortune?! (We learned, they’re all over Georgia to New York.)

Access to quality healthcare was not something we gave much thought to in the move, but lordy, with our creaks and groans, the days of frequent medical excursions can’t be far off. We feel so fortunate to live in an area teeming with top-notch medical facilities and professionals that we can schedule easily and that we can line up before we need them. Too many “That sounds horrible!” stories about having to wait for months to see someone and having to drive for hours to get needed care.

Most Chamber of Commerces are stuck in 1994. Their websites, their programming, their members, their aura. Greater Winston Salem, Inc. (GWSI) is fresh, in all the ways. No surprise—2024 Chamber of the Year. They have been an integral part of my transition as a small business owner and as a human. I mean, BIG SCISSORS! They threw lil’ ol’ me a ribbon cutting. They’ll always have a spot in my heart because I hosted my first in-person event in their space. “Will anyone come?! Will it go well?! Will the Chicago magic transfer to Winston?!” Yes, yes, and yes.

When I think North Carolina, I don’t think wine country. As describe by GWSI, “Winston-Salem is the gateway to the Yadkin Valley Wine Country region which is home to more than 70 wineries within a short drive of the city.” What a fun wee getaway from the hustle & bustle of the city (ha). I have yet to see any hustle or bustle.

Maybe related? Grapes! I’ve eaten more grapes in our time here than in my previous forty-six years. I’m addicted. They are the most firm, robust, delicious spheres of satisfaction. I didn’t expect a move to North Carolina would alter my fruit diet. Nor did I expect grapes to be a continued most-expensive line item in the food budget. Worth it!

Chicago is a melting pot. It has the largest Polish population outside of Poland, one of the largest Mexican populations in the US, and one of the largest Black populations of any US City (I just finished reading The Warmth of Other Suns, a fascinating, personal narrative look into the Great Migration; highly recommend!). I don’t know what I expected in Winston but with my continual surprise and delight when encountering people from a variety of ethnicities and races, apparently WHITE! was very much part of the expectation. Never happier to be wrong. I stumbled upon Fiesta Festival on one of my walks where hundreds of mostly Hispanics filled downtown streets amongst infectious salsa music, a language I don’t speak, and swirling scents of empanadas and carnitas. Beyond the diversity, I’ve been loving how much more integrated Winston feels. It definitely has pockets of these folks here and those folks there, but coming from Chicago, one of the most segregated cities, racial and ethnic meshing is more evident in Winston. At activities; at restaurants; at stores… When I look at friends made and Mac & Cheese attendees, it fills my cup to see rainbows upon rainbows.

We knew Wake Forest is here. That’s a big reason we chose Winston. We did not realize how many other schools call the Twin City home: Winston-Salem State University (an HBCU), Forsyth Technical Community College, University of North Carolina School of the Arts (UNCSA; fun fact: mascot is the Fighting Pickle), Carolina University, and Salem College. Consider our college campus loving hearts squeezed (we’ve visited 121 campuses all over the world).

I thought it’d be hard to leave behind Chicago’s deep and layered arts and entrepreneurial scene but Winston is called the City of Arts & Innovation for good reason. The first local arts council in the United States was born here and UNCSA is is down the street from us. Ben Folds as in Ben Folds Five grew up here and lives here. Maya Angelou lived here for 30+ years, until her 2014 death. Murals and sculptures are abundant across the city. We’ve been to concerts, improv, stand up, plays, musicals, galleries, festivals, open mics. Best Friend is on an improv team. I went to Moveable Feast, speed-dating with authors. I’m a part of a book club. I’ve befriended the head of a makerspace, a jewelry designer, and a woodworker (Chantae runs the Cash Mobs I post about, where a group of us mob two to three small businesses, agreeing to spend $5-$20 per business; wonderful way to explore the area, meet others, and support my peers). I’ve become a regular in the craft scene (loving it so much I started my own craft scene!). Winston has reinvented itself around biotech and research, especially through the Wake Forest School of Medicine / Atrium Health system and the Innovation Quarter, one of the fastest‑growing urban innovation districts in the U.S., often highlighted as a national model for turning old industrial sites into a modern “innovation ecosystem.” It combines labs, offices, residences, restaurants, parks, and public art, so people live, work, and socialize within the same walkable neighborhood. A myriad of coworking spaces host entrepreneurs and entrepreneurial events on the regular.

The ease to get both mountains and beaches is pinch-me intoxicating. This is one of the things we adored about Chattanooga; a quick elevated hike over lunch or after work? A view of peaks from your office window? Yes and yes. The closest mountain is 20ish minutes away. Within ninety minutes, we can be in the Blue Ridge Mountains, some of America’s most breathtaking peaks, especially come Fall. We have yet to experience North Carolina beaches but they are high on our list. Within three to four hours, we’re at the coastline.

The history of the area is inescapable. Before July, I had never heard the word “Moravian.” Now it’s part of our daily life, surrounded by Moravian churches, Moravian stars (on my list to buy for our new home!), and Moravian villages. The Moravians are German‑speaking Christians who came to North Carolina in the 1750s. Civil war fences randomly pop up here and there, as do historic marker signs; I pass no less than seven of each on my neighborhood walk route. It’s been interesting to witness how such an integral part of an area and its past, the tobacco industry, deals with being an industry many would love to do away with (me; I am many). The R.J. Reynolds Tobacco Company (RJR) dominated the local economy for most of the 20th century and while its reach and smoking has much declined, Reynolds is still very much alive in Winston’s day to day. The famous Reynolds High School (Ben Folds’ alma mater), Reynolds Building, Reynolda Gardens, and Reynolda House Museum of American Art are ubiquitous with the city, as the adorable Artomats, retro cigarette‑style vending machines that sell small, original works of art instead of cigarettes. 40ish exist across local galleries, museums, breweries, restaurants, and libraries, more than any other place in the world. Reynolds appears to have done and continues to do lots of good in and for the community. While smoking is definitely more prevalent here than in Chicago, it’s not the horror I thought it’d be and I’m able to live most of my life sans cancer-air.

Chicago has 81 libraries. I hardly used them. Here? (10 libraries) I’ve become a Library Girlie. From checking out my book club books to checking out my first audiobook via the fabulous Libby app. To attending an event in its massive meeting space (Forsyth County Democratic Women) to attending an event in its intimate meeting space (writing group). I haven’t yet used its makerspace, sound production studio, or small business center, or checked out the Birding Backpack (everything you need to go birding, in a backpack! I mean…). I’m too vintage to hang out in the cool “Why didn’t I have this growing up?!” teen center. I wandered the 3rd floor artist exhibit, cooing at painting after painting, followed by a “What the what?!” wandering into the open-air seating area. When we first visited, Central Library’s mere esthetics gave us, “Ohhhhhh! This is niiiiiice!,” let alone all of its offerings.

My walks are often hijacked by “Ohhhhhh! What is that?!?” photography sessions. Kudzu! Dogwood! Crêpe Myrtle! Magnolia! Sweetgum! Holly! Bamboo! Fig trees! People—we are people!—just have figs growing in their yards. “What’s that? You’d like a fig to snack? Lemme run outside.” Who says that?!? 

When visiting Boone, the adorable college town, home to Appalachia State, ninety-minutes from Winston, I met someone who, when I asked where he’s from, said “Down the mountain.” I feel like I’m in a Hallmark movie.

They call it “the mall.” I feel like I’m in a brat-pack movie. Molly Ringwald, will you meet up with me after school in your tight-rolled jeans? Don’t forget to bring your walkman and Tiger Beat.

Husband being from Louisiana and us returning there each year for the holidays, To Go Drinks are not new to me. But it is new living in a To Go Drink zone. A server asking you if you want a beverage to take with you as you leave a restaurant?! Evanston, Boston, Chicago—my former homes—would never. Yes, yes I do, please and thank you. And obviously, pebble ice. More southern delights.

I love me some public, accessible, open spaces and Winston doesn’t disappoint. In fact, they surprised. So. Many. Parks. And the tennis focus! Had no clue tennis’ history or popularity here. The city annually hosts the Winston-Salem Open, which brings top international players and big crowds. The tournament is the last ATP World Tour 250 event before the U.S. Open.

Speaking of sports, the German Men’s National Team selected Winston as their home-base for the 2026 FIFA World Cup, choosing Wake Forest University and The Graylyn Estate as its official training site and team headquarters. Who will invite me to Graylyn for a Jane Austen experience?!

I never once heard age-related compliments in Chicago. We’ve stopped counting how many times Winstonians exclaim how young I look when they learn my age (47). I was told “You should join the Under 40 chamber group.” At a 40 Under 40 event where I was a guest, I was told that I’d be up on the stage next year. And on and on. Unlike Best Friend, who keeps getting, without being asked, the senior discount at Publix. And he’s younger than me! I’m not laughing…LOLLOLOLOLOLOLOL.

I could care less about fancy when it comes to most things. Clothes; makeup; skin care; cars; bags; shoes; restaurants… eh, eh, eh. Give me all the Costco pants, Nordstrom Rack size twelves, and Cava bowls. But travel and gym—give me all the Four Seasons, first class seats, airport lounges, and frou-frou workout spots. So when I learned our Winston gym options and the Y was one that looked the best fit due to location, offerings, and price, I wasn’t cartwheeling. I had a bit of a snob hat on, entering the relationship with a nose tilted higher than it should’ve been, a chip on the ol’ shoulder, and a readiness to say “See! It’s horrible!” Egg on my face. Yes, it’s outdated esthetically and it lacks amenities I covet like towels, laundry, built in locker locks, Cowshed toiletries, and a steam room, and there are more children than I’d like (my preference is zero children). But other than that? Love! It’s cleaner than any gym I’ve patronized. Easy free street and lot parking (can’t say that about any of the Chicago gyms I was a member of). Best Friend loves the sauna. The pool is huge and well-used, all day every day. The staff friendly. The members diverse in every way imaginable; “This is America” diverse. There’s an array of cardio machines and weights. The classes range from gospel cycle to yoga, body pump to core, taught by thumbs-up instructors. My money is going to an organization that does good and has been doing good for years; Mom couldn’t afford to send me to summer camp or to take classes but with the help of Y scholarships, I was able to attend day camp, sleepaway camp, badminton, swimming, and gymnastics. And the biggest surprise? As someone who’s never cared about being in an all gender gym, I adore the women’s only room and spend all of my non-class time there. Bonus: I awwwwww! almost every visit, when I see the lobby filled with senior citizens doing puzzles and playing bingo; groups of teens of all races huddled over a TikTok; mismatched demographics lounging on the couches watching random sports or talk shows. To top it off, the grounds are a mini botanic-garden, with stone pavers, climbing ivy, and too many flower species to count. Soho House and Chicago Athletic Club, who? I’m a Y Girlie now.

As mentioned, I could continue listing random delights and surprises. But you get the gist…

Our new chapter has been a cascade of tiny joys.

Things That Feel Weird

Among the joys are raised eyebrows and head scratches. Disclaimer that “weird” does not (necessarily) = wrong or bad. Just different. Not what I’m used to.

You don’t need a city sticker on your car. You only have a back license plate, not front and back plates. Love-squeeze to Best Friend who surprised me with a custom front plate when we realized we had extra real estate to play with.

You need a permit for a home security system.

There are no speed or red light cameras here. That “Oh shit…” flash in your rearview mirror that every Chicagoan knows all too well isn’t a thing in Winston.

School zones are only for certain hours, and they’re odd times, like 2:30 to 3:50pm. In Chicago, if school is in session, school zones are all day.

The highway entrance/exit ramps are laughable, scarily short. Like, “you have seven seconds and seven feet to accelerate from five to fifty-five and merge” short.

You can get lettuce, milk, and peanut butter at Lowe’s. Which if I said in Chicago, would translate to “You can get lettuce, milk, and peanut butter at Home Depot.” Lowe’s here can mean the Home Depot-type store but it can also mean the grocery store, started here in Winston and now with eighty-one locations across multiple states. You can understand my confusion when someone suggested the Lowe’s live music happy hour as a fun wind-down the day activity—pinot and jazz amongst grout and paint samples?! 

Shared driveways are everywhere. Including many of the homes we visited in our search. Where one driveway sits between two homes and both homes use it. Or in at least once case we witnessed, five homes use it! I’ve never seen this. 

The number of heart attacks I’ve had, thinking I was driving the wrong way on a one-way street. Nope. You’re fine. It’s just people parking on whatever side of the street they want, regardless of direction they’re driving.

I was excited to leave our condo for numerous reasons, one being no more HOA. Surprise! Your new entire city is an HOA! They put these yellow citation signs in your yard if you’re an offender. Zoning, sidewalk blockage, or debris issues, I get. But overgrown grass or weeds?! City code requires lawns to be cut below a certain height; if it’s mowed but not kept up, you can get a notice. Which I double-take witnessed.

There are no street cleaning schedules here. Now that I type this, I don’t even know if there are any street cleaning vehicles here. I haven’t seen a street sweeper since moving. Versus in Chicago, you come out of the womb knowing what Tuesday of the month you need to move your car from one side of the street to the other for street cleaning, and what time of year you can’t park on certain streets due to snow.

College sports are king here. Winston doesn’t have any professional sports teams. Compared to Chicago’s Cubs, Sox, Bears, & Hawks. The South in general feels more college-sports intense. The local rivalries of note appear to be UNC vs. Duke for basketball and UNC vs. NC State for football. Winston does have a minor league baseball team, the Dash (soon to be the Carolina Reapers), and hockey team, the Thunderbirds. We’ve been to games for both; good times! But it does feel odd to not have that united city feeling around pro-sports. I was a part of some magical seasons in Chicago, with the 1985 Superbowl champs, the 1990s Michael Jordan Bulls, the 2005 White Sox World Series winners, the three-time Blackhawks Cup winners, and the 2016 Cubs World Series winners. The downtown parades and rallies for MJ and company occurred when I was in middle school and high school and are core childhood memories. And that breaking of the Cubs curse after seventy-one years, oof… Forever ingrained. Fly that W!

We haven’t had a plastic bag stash since pre-2020. With the pandemic, Chicago stores either did away with disposable bags all together or began to tax them. And with that, Chicagoans became a reusable bag-people. Our trunk became their permanent home. While some Winstonians bring their own bags, it’s definitely not the norm that it is in Chicago. We’re still default reusable folks but on occasion have forgotten them and all of a sudden, we have a plastic bag stash, like it’s 1999. This is an area we’re not trying to fit in and we’re hoping more locals join Team Reusable.

There’s a high number of private property and no trespassing signs on homes. I was curious about this phenomenon so did some digging. This is what one site says: “Chicago’s dense, walkable neighborhoods and more collectivist street culture make lots of ‘no trespassing’ signs feel unnecessary or overly aggressive, while Winston‑Salem’s suburban, property‑rights‑heavy norms make them much more common and socially acceptable. North Carolina law gives homeowners a very clear incentive to post ‘No Trespassing’ signs.”

I come from an area that has some of the tightest gun legislation in the country and where most in my world were anti-gun. Compared to me accidentally stumbling into a sold-out gun show a few months ago and to my numerous “aligned in most other ways” new friends who are pro-pew pew. I’ll never forget the wide-eyes “What is going on?! Where are we?!” I had our first night in Chattanooga when we made a Walmart trip for tupperware and groceries and the man in front of us at the cashier had a gun on his hip. Don’t think I’ll ever get used to or embrace this one.

Y’all heard my rant on sellers having to pay for a buyer’s realtor last year. There’s no law; it’s just “how it’s done.” I despise that as a reason. Especially for something that costs me $16,877.50—we paid $16,877.50 for someone else’s realtor. So I was looking forward to reaping the benefit of being a buyer this go round. LOL. Welcome to North Carolina, one of the least buyer-friendly states. Welcome to due diligence, two horrible words I didn’t know until the move. North Carolina, South Carolina, and Texas are due diligence states. “Due diligence is the period after your offer is accepted but before closing when you investigate the property. That includes ordering inspections (home, pest, structural, etc.), reviewing the title, checking zoning, verifying disclosures, and otherwise “doing your homework” before you’re legally locked into the deal. In North Carolina specifically, the buyer and seller write a due diligence period into the purchase contract. During that time you can walk away from the purchase “for any reason” (or no reason), as long as you do it by the deadline. The catch is that you must pay the seller a non‑refundable due diligence fee to get that window, often $500–$2,000 that goes straight to the seller. If you then find undisclosed problems and walk away, you lose that money even though the seller walks away too. This is unusual compared with many other states where inspection‑period protections are baked into the law without a separate, non‑refundable payment.” Trying to lemonade lemons, thankful we weren’t buying during COVID when the combination of North Carolina’s due diligence + it being an incredibly hot market led to shortened inspection windows and to $10,000 – $100,000 due diligence money to make offers stand out. We had a relatively smooth transaction, considering all that can go sideways in these deals. A few regrets but nothing substantial and nothing to take away from the excitement of our new home. But if and when I’m President, Mayor, any position of power that can do away with dumbness—byeeee sellers paying for buyers’ realtors and byeeeee due diligence.

I have to be careful on this topic. The emotions that emote when ex-Northeners talk about anything to do with snow… on both sides. The Yankees are flabbergasted at how everything shuts down for what we’d consider a dusting—school and thus much of life was closed for two weeks this Winter when we got eleven inches—and the locals find it weird we don’t embrace the shutdown and forced slowdown. Needless to say, I was the only person who shoveled on our block, and one of few in our neighborhood. I hate it. Locals response is “We let the sun melt it.” Two weeks later, I was still waiting for that sun, and very glad I had shoveled. For us, our neighbors, the mail person, Amazon drivers, doggies and their humans…  Things I heard repeatedly and I get: what happened this year was unusual in that the snow didn’t melt the next day and that Winston doesn’t have the infrastructure to handle snow like Chicago does. Because of the latter, the ice is horrible. I spun out for the first time in my forty-seven years. Salt trucks, I’ve never appreciated you more than this year. It was scary. We don’t want school buses or folks commuting to work on those roads. That said, there has to be a better solution to “This is just how it is…” I get not wanting to invest in infrastructure to deal with scenarios that happen once every few years. What I would’ve loved to see is just like how linemen came from other states in case we had widespread power outages like they were afraid would happen, I would’ve loved to see parking lots filled with salt trucks and snow plows from Ohio, Pennsylvania, Illinois, on standby, for if and when. Cause boy, did if and when happen. Yet beyond fridges filled with milk and bread and Netflix marathons loaded, no preparation was prepared. The brine they put down three days pre-snow appeared useless and it took plows weeks to get to our neighborhood streets.

As evidenced by the fact that I’m most known as Mac & Cheese or Trash Girl here—it’s ridiculous off the charts how many times I’ve been called these, usually shared in a real-time realization tone of “Wait, you’re Mac & Cheese?! You’re Trash Girl?!”—trash has been a big part of our transition. It started pre-move when I realized that I’d have to take the trash out for the time in my life. In Evanston, Boston, Chicago, you take your inside trash outside to the trash bins and that’s where your trash journey ends. The city comes by and empties the bin into their truck. Yes, it’s on a certain day of the week but we don’t really pay attention to that. No need. There’s no moving of the bins on your part. As opposed to in Winston, when I shared my genuine excitement about taking out the trash here in a Winston-Salem Facebook group, I was met with gazillions of tips, no no’s, and stories. Links to the Winston-Salem Collects app, now a shortcut on my phone screen. A neighbor printing out a copy of the trash schedule. Because here, “taking out the trash” means taking your inside trash outside to the trash bins and then, depending on the day of the week, and depending on the week, you roll your bin, bins x2, bins x3 to the curb. Maybe it’s just trash day. Maybe it’s trash + recycling day. Maybe it’s trash + recycling + yard waste day. But don’t try to get one past the city and put out your Yard Waste cart if it doesn’t have current sticker on it (it’s like Chicago’s city sticker on your car; you have to renew it every year); we didn’t realize we didn’t have an uptodate sticker or that that was a thing, and put out our green bin. End of day, we wheeled the still full bin back up the driveway, scratching our heads and wondering why the city didn’t like us. I’ve thought and talked about trash more in the last eight months than in the previous forty-six years of my life. I get a reminder notification every Tuesday 8pm to roll out the bin(s). What is my life?!

Add into the mix leaf collection and bulk pick-up day, what is my life?!?!?!??! You’re encouraged to pile all your leaves into heaps on your sidewalk and supposedly there’s a schedule where the city comes by and collects them. I did not see this work effectively, as heaps of heaps were blocking street and sidewalks for months. And then the one time I saw a leaf collection truck, all the crushed leaves were flying out of the truck as it drove down Broad. I have yet to experience Bulk Pickup Day as we just missed it last year so it’s coming up, but it sounds like quite the experience. There’s a window of a few months where you’re allowed to put household items that are too big for the regular trash can out on your curb and the city will come collect them for free. You can start putting out items the weekend before your scheduled week.

Allowed bulk pickup items — 

• Furniture: sofas, chairs, tables, dressers, bed frames, etc.

• Appliances that are not refrigerators/freezers (stoves, microwaves, washers, dryers, water heaters, etc.).

• Mattresses and box springs

• TVs and electronics

• Yard and landscaping items: small trees and branches, small sheds, grills, lawn mowers, etc.

Chicago, can you imagine mowers and stoves lining Ashland and Addison?! I cannot.

Evidently, it’s a wonderful opportunity to go “shopping” and I’m looking forward to perusing myself. That said, I’m also wide-eyed hesitant about how much street and sidewalk blocking there may be. Not a fan how many people block bike lanes and walking paths with their cars, leaves, branches, trash bins in normal times. I can’t fathom what it’s going to be like when couches and stoves are in the mix. I both love the idea and am scared-curious about the idea. In Chicago, I can’t say it was fun to have to pay the city for trash overages or have to pay a junk removal service when we tossed our sleeper sofa or the like, and how nice it would’ve been if we could’ve just put it outside and had someone take it, no charge. But with the density… my brain is not computing large city Bulk Pickup. The closest scenario I can imagine and have witnessed is in high-student population cities like Boston, the end of the school year when the curbs are filled with items left by college kids. A glorious, ugly shit-show of an “Everything’s free!” garage sale.

Gravity! It exists here! You take Chicago-flatness for granted. You mow your grass and push your shopping cart to your car without thinking about your mower or cart deciding to not stay where you put them. After you mow your grass (for the 1st time in your life! Exhilarating!) and are emptying the bag, when you turn your back to go to the bin, make sure the mower isn’t on a slope. Cause you’ll find yourself chunkily chasing it down your driveway, not in time, and it’ll cross the street to your neighbors house, only stopping cause of her curb. When shopping at Lowe’s and are emptying the cart into your trunk, make sure the cart isn’t on a slope. Cause you’ll find yourself chunkily chasing it across the parking lot, not in time, and it’ll bump not one but two medians, only stopping cause of the curb 50 feet away. Hypothetically…

With all this newness and “getting out there,” the amount of small talk and “nice to meet you…” chatter has been plenteous.

In Chicago, one of the first things you do in such scenarios is at the very least share if not discuss where you live. It goes something like this —

“Where do you live?”

“Wicker Park” or “Division and Damen” or “Evanston.” Where Wicker Park is a Chicago neighborhood, Division and Damen is the intersection of two main Chicago streets, and Evanston is a Chicago suburb.

Here, people seem confused when I follow-up ask what neighborhood they live in. Like, parlez-vous français confused.

Winstonians respond first with a quizzical pause and then with county or road — “By Hanes Mall Road.” “Near Robinhood Road.” “Close to Davidson County.” This is confusing to me; isn’t Robinhood Road miles long? How does this tell me where something is? And counties… oh boy. We have counties in Illinois but having grown up and spent most of my adult life in the Chicagoland area, I’ve never heard anyone use a county as a way to show location. Not to mention I’m having trouble just pronouncing my county, Forsyth—half of Winstonians say Foursyth, a smooth single word (how I say it), and half of Winstonians say Fer-Syth, as a local told me, “Heavy on the Fer.” And then when I share the two examples in an ask for help, they tell me they don’t hear a difference. 😂

So upon meeting more new faces and hearing one of them give the directions ”On Reynolda,” because it felt like a safe space, I decided to finally openly display my confusion and ask.

After chuckling at my perplexity, they said, “We may be Southern and friendly but we don’t want you knowing exactly where we live.”

“So if I live in West Salem, I don’t say I live in West Salem? What do I say?”

“You say a place you live by.”

“I live by the new Bobby Boy?”

“Yep.”

Tangent: I’ve had multiple locals tell me no one specifies area UNLESS they live in Ardmore, both because everyone knows where Ardmore is and because Ardmorians like sharing they live in Ardmore. 😄 🤷🏽‍♀️

All this to say, if we’ve met and I’ve asked “What neighborhood do you live in?”, I swear, I’m not a creep! That’s just how we small talk in Chicago. We are a city of neighborhoods, each one very different than the other and each resident very neighborhood proud. I ain’t trying to figure out your address or which house is yours. I’m just trying to get a general sense of where you lay your head at night so I can say things like “Ohhhh, right by Remedy; I love that place!” or “We just went to an open house over there; so cute!”

Cognizant that I’m in a new place with different customs, wanting to be respectful and just one of the gang, I’ve added all this to my “how to fit in” diary and will now change both what I ask and how I answer. But in case I slip up and forget—not trying to get all up in your business, cross my wee heart.

I’ve Learned

What mosquito dunks are and how to make them. Fill a bucket with water and yard waste to make it funky, drop in a dunk—”a small, donut‑shaped biological mosquito control product”—and leave the bucket in a sunny spot. You provide mosquitoes an inviting place to lay eggs, then the dunk kills the larvae there, reducing how many adults are flying around your yard.

Winstonian Sandra Waldon was the first paid female firefighter in the US (1973).

Krispy Kreme, Hanes (underwear and tshirts), and Texas Pete (hot sauce) were born here.

North Carolina produces more sweet potatoes than any other state.

Wake Forest the school isn’t in Wake Forest the town. The college was in Wake Forest, about 100 miles away, outside of Raleigh, until the 50s, when it needed more money and room to expand. The Reynolds Foundation offered it funding and land to relocate to Winston-Salem. The school opened in its new location in 1956. The old campus in the town of Wake Forest is now home to Southeastern Baptist Theological Seminary.

Today’s public bus system has roots in the Safe Bus Company which operated  from 1926 to 1972. It was formed by Blacks to provide transportation to Black workers as the system at the time didn’t serve areas where most of them lived. According to the Forsyth County Historic Resources Commission, the Safe Bus Company eventually employed more than 80 drivers and carried 8,000 passengers a day, earning the distinction of being the largest African-American-owned and operated transportation business in the world. The company ran until 1972, when the Winston-Salem Transit Authority purchased its assets.

“All the way” means you want chili on your burger, hot dog, nachos.

We didn’t realize Maya Angelou’s connection to the city. My namesake taught a wide range of courses at Wake Forest (literature, theology, ethics, writing, theater, philosophy) and was known locally simply as “Professor.” There’s a freshman dorm named Angelou Residence Hall. The universe telling us we chose well! Mom would be tickled.

The State of My Worries

When you make a life leap, you have worries. Beyond the smaller worries like having to find a new doctor and mechanic you like and adjusting to a new time zone, are the biggies —

• Are we idiots for selling our very desirable condo in a very desirable location with a very desirable 2% mortgage rate?
• Will we find our people outside of our deep blue bubble?
• Can we manage being a one-car family in a car-centric place?
• Will my 100% word of mouth business work in a place where I know zero mouths?
• Will we regret ________?

Guess what? Zero regret. I mean, sure tiny regret like I wish we had reno’ed our condo earlier and been able to live in the aftermath longer, I wish I hadn’t donated all my folding chairs, and I wish I had gone to this restaurant and that show before moving. But no regret-regret.

I wouldn’t want to let something like a fabulous mortgage rate dictate my life plans. While we lost that low-low rate, we gained a single-family home in exchange for a condo, at a price that’s allowing us freedom we’ve never had before.

Winston-Salem and North Carolina are way more purple than I thought. Our neighborhood is overrun with rainbow flags and Black Lives Matter yard signs. Even a few Harris remnants remain. The No Kings rallies were overflowing and hope-giving. Democratic Party events are frequent and well-attended. I spent the day yesterday wandering in and out of stores downtown with “ICE isn’t welcome here” signs. While it’s much more likely to run into Trump’ers here than in Chicago, I rarely do. It’s been an adjustment having to be cautious about when and where I’m blue or BLUE but even that has dissipated over the eight months and I find myself leaning more into this is who I am even if who I am rubs others the wrong way and/or makes me stick out. Love is love is love.

We’ve done a good job of compromising and adjusting when it comes to one car. Best Friend will rent a car for road trips, where in the past he would’ve taken our car because I would walk, bike, or CTA. I drive him to the car rental place, even when I’d rather not or when he could Uber, cause I recognize he’s shifting his life to make my life easier. If I’m going to something downtown, which I do often, instead of me taking the car all day, he’ll drop me off and then I’ll walk home. And instead of the walks being annoyances, I turn them into joys—a slow, unrushed meandering, listening to a podcast or audiobook, along four different routes of my choice, including one through the delightful Old Salem and Salem College grounds, enjoying fresh air and sun and an alternative-gym outing. The easy seven-minute car ride for him to drop me off so he can have the car; the refreshing twenty-five minute walk for me to get home… both validation we chose city and neighborhood well.

Mac & Cheese is plugging along. I’m still running my cleaning business in Chicago. Still consulting and coaching virtually with clients, local and elsewhere. Still running courses and selling products. Still speaking and facilitating, local and elsewhere. Still hosting virtual and in-person goodness. In Winston, I’ve had two Blueprint Board workshops, a Workplace Improv workshop, two Idea Potlucks, and a speed-friending, and the upcoming calendar includes another speed-friending, two Comfy Clubs, and monthly Idea Potlucks through the end of the year. Not to mention wheels turning on TBD goodness. It’s been twenty-two years of self-employed, work from home, say yes and figure it out as I go bliss, and thankfully, a new zip code does not equal a new MO—appears I can continue to do things I enjoy and that I’m good at, and that people will pay me for said things because said things are good for them and will spread the Mac & Cheese word because they deem said things things their people would want to know about. Win-win-win. Life of Yes℠. Check out the oh so sweet reviews folks have left.

So the state of my worries is: What worries?

What I Miss-Miss

Being the Chicago-homer that I am, I thought it’d be painful how much I miss-miss. The kind of miss that’s top of mind. That hurt-squeezes your heart. That makes you sigh wistfully. That takes you out of your default day to day exuberance.

But, while there is plenty Chicago’ness that I adore and that I don’t have in Winston, considering there’s nothing more I love than to make a list and to spew Chicago-ese, my list of what I miss-miss is surprisingly short —

• A walkable gym
• Good public transit, especially the El and the Metra. I. Love. Trains.
• A bike-share; they have a scooter-share here but it’s no 10,000 bikes across the city and suburbs, including 3500 e-bikes. It appears Winston used to have a bike share, Flowbikes, but it shut down a few years ago
• Alleys; mostly for trash-related reasons but also access reasons
• Pervasive, connected bike and pedestrian infrastructure
• The skyline; top five skyline in the world
• Water; I’ve never lived anywhere land locked. I miss the Chicago River and Lake Michigan. I miss the 19 mile lakefront path. I miss visitors thinking “the lake” = a pond and being blown away that a beach exists across the street from skyscrapers and that you can’t see the other side. A lakefront sunrise is a moment.
• Clumps of bicyclists at stop lights, waiting to take off
• Easy to get to, international, direct-flights galore airports; it used to be a seven minute walk to the Blue Line, $2.50 45 minute El ride to O’Hare or Midway, direct flight anywhere at any time. Now? I can’t outline the ordeal and expense and time spent. It’s too painful.
• Salt trucks and snow plows
• Being in the heart of Chicago when city pride is high and we’re all for one and one for all, a la the 2025-2026 Good, Better, Best Bears
• Amtrak; it used to stop here until 1970 and there’s talk that Union Station will once again be a train hub but at the moment, I cannot live out my train travel dreams unless I go to another city
• Connected neighborhoods; you can spend the entire day pleasantly walking from Chicago neighborhood to Chicago neighborhood. In Winston, it’ll be seven minutes before the sidewalks end or you’re on a busy street or there’s no pedestrian access.
• A dishwasher that works; nothing to do with Winston specifically, it just so happens that the dishwasher in our rental sucks and I had the Pinch me! experience of a brand new Bosch 800 in our condo. But, squeeeee! The new house will have a new Bosch. 
• The Debbie Tree; friends have been the loveliest, sening me photo updates of the Oak I planted across the street from the lake, the bike path, and Northwestern in Mom’s memory. I plan on doing another Mom Memorial planting once we’re settled in the house.

In Conclusion

There’s so much more to say. So many more feelings. Experiences. People. I’ve written a novel and feel I’ve barely scratched the swirls that make up our eight months in Winston. A testament to a full life. Which is why we moved. We have full lives. We’re re-energized. Rejuvenated. Reinvigorated. Reborn. Which are truly delightful sensations to feel at age forty-seven.

If you’re considering a leap of your own—Career? Location? Relationship?—here’s your sign to jump. Especially if you feel stuck and stagnant. Bored and listless. If you’re not squeeeeee to check out the grocery store or farmer’s market or local fast food chain. 

The Type A, spreadsheet, arrive fifteen minutes early people we are, I can’t believe we went as quickly as we did from “Maybe we should use this ‘opportunity’ (of forced home renovation due to water damage) to explore selling the condo” to “Let’s sell!” [four days], that we sold our home without knowing where we were going, that various states and various cities were in contention, and that we were this close to moving to Durham, NC and would’ve had our rental application not been beaten out by another interested party.

Life has a way of shaking out, even when things don’t go to plan. Sometimes, often times, the detour is better than the planned route. The key is that you have press the gas. You may reverse, you may go slow, but at least you’re moving.

Regret in this scenario is us continuing to say, “Is it time to leave Chicago?” but never leaving. 

Even if we hated Winston. Even if wasn’t at all what we expected or wanted, in all the negative ways. Even if we moved back to Chicago.

Luckily, that’s not our situation. Winstonians have welcomed us with sugar-cookies and peasant bread and a mosquito swatter and ice melt left on our porch, with invitations to dinner at their family tables, and with laughter and vulnerable shares and cheering for strangers at events. We’ve been told over and over: “We’re so glad you moved here.” “We’re so lucky to have you.” “Sorry Chicago, your loss.” “We hope you stay forever.”

We feel at home, that we belong, that we’ve found where we’re supposed to be.

As Good Housekeeping wrote: “Winston-Salem has all the attractions and amenities of a big city on a more snackable scale.” And if there’s one truth universally acknowledged, it’s that this girl loves snacks.

Supplemental’ness

• Is It Time to Leave Chicago? (Penned in 2014; that’s how long we’ve been talking about moving)
• Life Lesson: Never Check Email When In Mexico (Aka the last time we bought a home; spoiler: not fun)
• Live Elsewhere Experiment: Chattanooga
• Next Chapter: we’re moving! I found it fascinating to compare then (May) and now (March)
• In Saya Musings: Confidence | Community | Networking | Self-Love | Challenges, I have a “Ways I’ve ‘got out there’ in my new city” list
• Lists — 
  • Where we’ve traveled
  • College campuses visited
  • Life of Yes℠ Resources which includes “getting out there” recommendations; bookmark this page as I’m always updating it!
• Mac & Cheese calendar; speaking & facilitation; consulting; store — Come to an event! Bring us into your work! Take my course! Read my e-book! Buy swag!