City Observer: From Outsider To Insider

The dazzling, the Haipai culture, and the hidden gems of Shanghai

credit: Xiao Hongshu

Last week, I came across a book at Sisyphe Bookstore — Outsider by Christopher St. Cavish, a chef-turned-food writer who has lived in Shanghai since 2005. He is now widely known as an expert on the city’s most famous delicacy, xiaolongbao, after becoming the first to measure and grade them with a caliper — a quirky act that turned into a cultural sensation.

What fascinates me about his book is the city itself — Shanghai, a place that both of us first came to by accident, but ended up staying for nearly twenty years. His book sparked a chain of thoughts, circling around a question that has haunted me for quite a while: how long does it take to turn yourself from an outsider into an insider, from a tourist into someone who has truly put down roots in a place you can finally call “home”?

This week, I am exploring the theme of the city and the process of assimilation, delving into my personal experiences, inspired by Christopher’s Outsider. This time, I don’t need a caliper — I navigate with my own observations and first-hand encounters. It has been a long journey, from being a stranger to becoming a permanent resident, a process that involves putting down roots, a form of assimilation. This process touches everything in life, but most of all, it revolves around the place I live, the jobs I do, the people I meet, and the food I eat. I hope this weekly post offers you a glimpse of Shanghai city life, as well as a small hint at how to decipher its culture.

Three stages, three layers: from outside to inside

As time changes, so does the taste of wine. The same can be said of a city. Like peeling an onion, you only reach the core after layer upon layer. To put it simply, I see three layers, or three stages, though the length of each depends on how much you commit yourself to the journey.

The first layer of Shanghai: fireworks, thrilling, and dazzling for tourists

The night I first landed in Shanghai in 2002, I was taken to the Bund, strolling past its historic buildings, so thrilled that I even wrapped my arms around the big stone columns. Two weeks later, I started work at a U.S. architecture firm as a translator and assistant to its China GM. My colleagues were very friendly, warmly recommending hot spots and signature destinations — but places that only tourists swarmed to. I didn’t blame them, but I wasn’t interested in the crowded East Nanjing Road or the Oriental Pearl Tower, especially during the holiday peak.

On the contrary, my first job opened my eyes to a very different Shanghai. As the GM’s assistant, I followed him into fine dining restaurants, five-star hotels, stylish bars, and fancy offices, meeting senior officials, legendary entrepreneurs, and state-owned enterprises, introducing our American architects and their world-class designs. It was mind-blowing — like being swept into a tide, overwhelming and unprepared, almost engulfing me. I witnessed the unstoppable vitality and bold ambition of the city, as if from the driver’s seat. My days felt like a movie, shifting from my humble flat to glamorous presentations and business occasions. Yet, dazzling as they were, those moments were short-lived — like fireworks at night. I enjoyed the ride, but soon realized it was only about work, and nothing truly belonged to me. After work, I felt empty, even lost. With my small salary, I told myself I could leave any time. With such a “tourist” mindset — chasing only “fun” — I neither fell in love with the city nor felt a desire to dive deeper.

But then came a turning point: my company helped transfer my hukou from Chongqing to Shanghai, officially making me a “new Shanghainese.” Looking back, this was a game-changer. I gradually let go of the idea of leaving and put the word “stay” back in my dictionary.

A year later, I left the architecture firm and joined a glamorous international ad agency, with my salary doubled. In the decade that followed, I built my career in marketing consultancy and began putting down real roots.

The second layer of Shanghai: Haipai culture for a sojourner

In this stage, I shifted from “tourist” to “sojourner,” while still dreaming of a final destination — New York City, driven by unbridled ambition. I lived what I call a “jīngzhì qióng lifestyle” (aesthetically sophisticated but financially struggling), spending most of my hard-earned money on fine dining, fashion, gym memberships, and binge-watching Sex and the City, pretending to live a life that wasn’t mine. Shanghai is a fabulous city where something is always happening. It can be irresistible, offering so many good things at once, but I often forgot that everything came with a hidden price tag, tucked inside the bill.

If you’ve watched B for Busy (2021) and Her Story (2024), both from up-and-coming director Shao Yihui and both set against the backdrop of contemporary Shanghai, you may have sensed the layered meaning behind the city’s much-evoked “charm.” It is a flair woven from contradictions: old and new, modern and historic, East and West — a fusion, a mystery, a melancholic love song, a poem, a melody, an elegance found in everyday life.

Shao’s films, through both characters and stories, unfold mostly within Shanghai’s Former French Concession (FFC), long regarded as the city’s cultural epicenter and the embodiment of Haipai culture at its best. The FFC is a true melting pot of expatriates and locals, the poor and the wealthy, alive with indie shops, cafés, restaurants, modest housing, grand villas, and historic architecture. It offers endless material and inspiration for literature, film, and artistic creation.

“Sojourners” themselves can be divided into light and heavy cultural consumers. The light ones are those who enjoy a croissant with coffee along an alley, or dress in a qipao and walk past historic architectures, like Maggie Cheung in In the Mood for Love. The heavy ones are the hopeless cultural explorers, those obsessed with forgotten details of the past, untold stories, mysteries, drama, even crime. Either way, being a sojourner in a cosmopolitan city, whether Shanghai or New York, can be very expensive.

The inner layer of Shanghai: hidden treasures for residents

After spending over a decade in this stage, I eventually moved into a flat we bought in Shanghai’s middle ring, with almost a one-hour commute to downtown. Once again, my role changed — this time, from sojourner to permanent resident. I began to look at the city differently, with new eyes, and discovered a new taste.

I am no longer obsessed over the FFC or the symbolic Haipai culture it represents. I still go there from time to time for work, to meet friends, or to enjoy a seasonal brunch or gelato — but I notice many more things now than I once did.

It was life-changing for me, because I discovered that the most mundane joys in Shanghai often cost little or nothing at all, thanks to the city’s sheer generosity. I don’t rely on Dianping (China’s “Yelp”) or GPS to guide me through the streets; instead, I’ve learned to uncover hidden treasures with instinct, intuition, or tips from insider friends. I used to say, “so many things happen in this amazing city,” but now I would correct myself: so many free and fascinating things happen here every day.

If, like me, you love art and culture, you’ll find that many of Shanghai’s top museums and galleries open their doors for free on certain days each month. Historic buildings regularly host lectures on history and culture, either free or at such a token price you hardly notice. I once sat beneath the silent gaze of ancient Buddhas on the top floor of a museum, watching the Bund’s glittering nightscape, after attending a weekend lecture by a renowned Fudan historian. The lecture itself was memorable, but the museum tour offered afterward felt like an unexpected gift.

Even in the expensive heart of the Former French Concession, I could feed myself with a hearty meal of beef and vegetables, just like in any ordinary Shanghai household, for around 20 RMB ($2.80). The meal came with sunlight pouring through the windows, clean air-conditioning, and unlimited hot tea. What touched me most was not just the food, but the people I shared the space with: retirees and octogenarians from the neighborhood, stylish young professionals in their 30s, delivery men with helmets resting at their side, laborers from nearby construction sites, and sanitation workers on a break. In these community canteens, everyone is equal, quietly enjoying a proper meal and their hard-earned respite, with dignity.

credit: Xiao Hongshu

Surely, Shanghai is far from perfect. My bumpy journey from outsider to insider is a personal one, with my observations of places, people, and food seen through my own unique lens.

But from this process of assimilation, I've learned one profound truth: you never fully understand a city, just as you never fully understand yourself. It is a lifelong search. The longer you put down roots, the more you realize how little you know, and the more there is still waiting to be explored. What seems attention-grabbing at first glance may be nothing more than a siren’s call, while the hidden gems reveal themselves only through time, patience, a discerning heart, and a little luck.