From the Stairwell to Hell to La La Land and Netflix

Ann Sim is telling me about her children. She says she has 50 of them, give or take, and her main job is protecting them and providing them everything they need to succeed. 

It’s not uncommon to hear restaurant managers refer to their staff this way, but, unlike most of them, Sim has a necklace that I noticed when we sat down: a thin chain with “Callie” written in gold, like some people wear with the names of their actual kids. You get the sense Sim really means it. 

Sim is the general manager of Callie. She opened the East Village Mediterranean-style gem with chef Travis Swikard in the middle of 2021, and now they’re joining forces again for their second location, a to-be-named French restaurant in La Jolla Commons. Much has been made of Swikard’s experience, and rightfully so—more than a decade alongside Daniel Boulud in New York tends to draw eyes—but in terms of pure tonnage of resume fireworks, Sim might have him beat.

She’s worked at some of the most well-respected places in New York and Los Angeles, including a marquee stint as a captain at Eleven Madison Park, what was—at the time, by every metric available—the best restaurant in the world.

You wouldn’t know it to talk to her. The SoCal native is approachable with an easy laugh. But to watch her at the restaurant is to witness a pro at work. You see it in the way she adjusts a napkin or pushes in a chair, the way she glides between tables or opens a bottle of wine. But you also sense it in the warmth with which she greets guests, touches tables, and coaches her staff. 

The front of house at Callie is, like the cuisine, a union of world-class refinement and California vibes. The synthesis of these apparent contradictions is a big part of why Callie is such a local treasure—and why it has earned it national and international recognition (as well as this magazine’s award for Best Restaurant two years in a row). It’s an impressive CV for a woman whose main professional goal throughout college was to get out of restaurants for good.

The daughter of Korean immigrants-turned-restaurateurs, Sim was born and raised in Orange County. As a kid, Sim was “free child labor,” she quips—she worked the counter, grilled chicken, waited tables, whatever her parents’ business needed that day. She stayed in restaurants through college, serving and bartending, and graduated from UC Irvine sans debt. The tradeoff: They were bad places with toxic cultures. She had different ideas of success.

After college in 2011, she took her meager savings and moved to New York, something she had wanted to do since she was a kid. Though she had planned to change industries, she needed a job, so a friend got her an interview at Daniel Boulud’s celebrated Mediterranean restaurant, Boulud Sud, as a host.

For all her experience, she was completely unprepared. “I didn’t know who Daniel Boulud was,” she says. “I didn’t know what fine dining even meant. I never heard the phrase.” What she did know, however, was how to work hard and learn. She absorbed everything she could, bouncing from the host stand to the events team to management. 

It was there that she first met a young Swikard and other high-caliber restaurant pros, and it opened her eyes to what this life could be. “They were so good at what they did that I was like, ‘Oh, this is actually a career. This is a profession. This is actually something very respectable,’” she recalls.

Her next job was at Eleven Madison Park. The restaurant already had three Michelin stars, and, during her tenure, it earned an exuberant review from the New York Times, a James Beard Award for outstanding service, and the title of Best Restaurant in the World from the World’s 50 Best. 

When Eleven Madison Park closed for renovations, Sim took the opportunity to come back to California. She arrived in LA at the end of 2017 to open the area’s NoMad Hotel, and did a stint as the GM of Maude in Beverly Hills. After the start of the pandemic, she got a random text from Swikard, her old Boulud Sud colleague, who was trying to open a restaurant in San Diego and had just lost his GM. Did she know anyone who might want the job?

Callie is theirs. It is her and Swikard’s united vision of hospitality and what a restaurant should be. She’s not courting the 50 Best awards—she’s too “old and jaded,” she says, and those things come at too high a human cost (she still can’t watch The Bear, for example). To her, success comes from working hard, taking care of her people, and connecting with the community. Nearly two and a half years after she and Swikard opened the restaurant’s doors, the reservation list at Callie is still full pretty much every night.

“I genuinely care about the business as well as every single one of my employees,” she says. “So I don’t care if anyone’s like, ‘Oh, you wear a necklace with the name of your job?’ I don’t think it’s weird, because for me, it’s like, ‘I also pushed this baby out.’”

And with her and Swikard’s second culinary progeny incoming, she may have to add another charm.

Walking into a room full of strangers isn’t high on the fun index for most. It’s inherently awkward: Everyone’s standing in closed-loop clusters, deep in conversation, and, depending on your social aptitude, the feeling is somewhere between light apprehension and burning alive from the inside out. The pull to retreat or reflexively look busy on your phone is stronger than the drink you now deeply crave. Having friends is nice, but making friends can be brutal.

There’s plenty of commentary on the loneliness epidemic. Last year, the American Psychiatric Association reported that one in three adults feel lonely at least once a week; those aged 18 to 34 are more likely to feel isolated and even more likely to turn to social media as a result. Dr. Vivek Murthy’s “My Parting Prescription for America” cautioned that “being socially disconnected increases our risk of heart disease, dementia, depression, anxiety, and premature death.” So it’s not just an emotional need; it’s nearly nutritional—chit-chat and the occasional wine-fueled, emotional deep-dive are just as important as Pilates and a reasonable amount of kale.

Finding social connections in any city is hard, but San Diego has very specific challenges. This is largely a transient population that acts as a temporary hotspot for many and a permanent home for few. Pick your reason: high rent, surreal gas prices, housing shortage, meh job opportunities (ranked 71st in the country in 2025), or the fact that active military is a sizable chunk of us (110,000-ish)—stationed here for a stretch, then gone. This constant flow of departees sucks out the potential for deeply established families and friend groups, leaving a good share of nomads, searchers, and plenty of people feeling socially awkward.

“There’s an underlying loneliness in all of us,” says Ramel Wallace, the host of monthly meetup CreativeMornings. “There are not a lot of San Diegans who are born and raised here, so [even those] San Diegans end up being just as lonely as the person who just got here.”

Every month, in local libraries, breweries, and small businesses, there are ambitious social architects who have made a career out of undoing social sads. Extroverted champions of the awkward and searching, they’ve struck gold on in-person connection.

The first moments in a social situation are crucial. Sets the tone and cools the nerves.

At Pitch-A-Friend, singles recruit their close friends to present a slideshow of their dating green flags. The entry points for connection at Pitch-A-Friend are simple, old tech: stickers. Each colored sticker indicates if the wearer is single or taken, queer or straight, or practicing ethical non-monogamy (in a partnership but open to others under a mutual understanding).

At the helm of each showcase is Arielle Fuller, aka Chief Wingwoman, who is making dating hopeful again. As Fuller explains, this takes some of the fear of rejection out of a first interaction. “Putting a sticker on immediately means, ‘I wanted to leave my house and talk to someone, and I am a safe space to come and speak to me,’” she says.

Of course, not all of San Diego’s events designed to make connections are romantic. On the last Friday of every month, hundreds gather at San Diego Central Library for the local chapter of CreativeMornings—an org formed to unite creatives in various cities across the world (designers, artists, writers, producers, performers, architects, etc.).

These aren’t your standard business card swaps, though. Coming from a hip-hop background, host Wallace uses call-and-response to break the fourth wall. “This is not my stage at all, this is our stage,” he says.

In your standard lecture-based meetup, the crowd silently faces the host and acknowledges nobody except those they came with. At CreativeMornings, everyone is encouraged to look around, pay attention to the strangers in the audience—not just the host. Wallace will pull volunteers to read the CM manifesto aloud, and he passes the mic to creatives, who make 30-second pitches to the community about projects they’re working on—and there’s always an invitation to connect and collaborate with the presenters whose ideas struck a chord.

The U.S. Chamber of Connection (yes it exists) says people experience life transitions nearly every year, and in these stretches are more open to forming new habits, relationships, and communities. In a revolving-door city like ours, the transition often comes when someone moves away. In 2023, the Census Bureau reported San Diego had the ninth-highest rates of domestic out-migration in the US.

This poses an issue for friendships that IRL SD addresses in monthly friend-making events called 619 Night.

“San Diego isn’t a place a lot of people stay forever,” says Alex Hunter, the creator of IRL SD. “They leave, and people [who stay] lose that community, so they’re hungry for community again.”

Their website describes the vibe as “backyard party meets college fair meets networking event meets happy hour.” Each follows a theme—wellness, sports, refresh and reset, etc.—with related community groups joining as well.

“The people I encounter are trying to get a fresh start in some capacity, so they’re more open, receptive, and ready to meet new friends,” Hunter says. “They need the circle.”

Another way adults can break out of this disconnection is to revert in unison, says artist Elisa Summiel-Bey. The 2015-ish adult coloring book moment in the US was based on some real science, with multiple studies finding coloring has a noticeable meditative and stress-release effect by taking the brain away from anxieties and mental inventories, and focusing it on a simple, easy art. Summiel-Bey’s company Illustrated Melanin throws “Color & Chill” events, turning that trend into a group exercise, along with live DJ sets, wellness experts doing sound baths, and food and drink from BIPOC-owned local businesses. “I tend to think of coloring as your way to tap back into your childlike play,” she says. “As adults, I think we’re almost scared to let loose and have that unabashed joy.”

All of these social meetups attract crowds of likeminded connection-seekers, but high attendance is not the only thing that matters. Metrics nuts can track RSVPs, but spreadsheets can’t capture intangible wins: friendships made, innovative ideas sparked, collaborations kicked off. At CreativeMornings, Wallace redefines ROI as Return On Imagination. Resounding success means thoughtful inquiries over coffee, curiosity about the monthly meeting themes, and requests to take the microphone.

A simple, observable ROI is an increased number of window shoppers to the experience—on the periphery, watching from afar, looking for the right way in. Hunter from IRL SD sees the anxiety in her DMs. “The scariest part for you right now is not meeting new friends: It’s the unknown,” she says. “It’s the gap between ‘I’m here’ and ‘That’s where I need to be.’ If I can help you understand, or get a little bit of a shape around that unknown, it’s much more approachable.”

Being able to bridge that gap, however, depends on your ability to step out of your own mind. “It’s not a connection crisis; it’s a courage and confidence crisis,” says Fuller. The first hello could be as easy as, “Hey, cool shirt.” These are the types of things she includes in her confidence lab reels on Instagram and weekly newsletters.

Ever left a social event and shot straight into a spiral? Was I being weird? Why did I tell that story? I hope that person moves to another state very soon.

The experts say that post-event self-interrogation is a standard-issue part of being alive.

“I love awkward people, and I love being awkward myself,” says Wallace. “It’s humbling to experience: ‘I’m not alone. Finally someone is not put together.’ So give yourself that grace.”

Ray’s Tennis doesn’t look like much from the outside. Never has. It’s just a green box with cloudy windows in Hillcrest, just steps away from a McDonald’s on University Avenue. But for nearly 60 years, this place has been the genesis for three generations of San Diego tennis dreams. Head inside, and you enter one of the tennis world’s great cornucopias.

For years, there was a tennis court behind the store, where owner Bob Ray gave countless lessons. It was like a racket-sport speakeasy; most customers didn’t realize the court existed unless Bob or his wife, Hiroko, guided them through the back door of the shop. Eventually they converted it into a half-court indoors—where a patron might take a racket for a few trial thwacks, trying to avoid rounders of tennis clothes that shared the space.

The shop is an abridged living history. Relics hang from the ceiling: a model of an old metal racket used by fiery lefthander Jimmy Connors in his heyday, and a version of the wooden Donnay that Björn Borg wielded on his way to five consecutive Wimbledon championships from 1976 to 1980.

And just inside the front door is Hiroko eternally stringing new rackets, carefully threading and adjusting the tension of the polyester strings, back and forth, until she has the entire racket head strung.

“I worked seven days a week—five days off in the year,” she says. “My hearing is still good. Physically, I’m as good as I was. Working seven days a week, standing all day. I’m mentally healthier than most people.”

The racket stringing is an operation she does up to 20 times a day—and one that, in some ways, resembles the thread work done by her father decades ago, when he ran a tailor’s shop in Japan.

Hiroko, now 81, was born in the city of Yokosuka at the tail end of the WWII. Her family evacuated to the countryside to escape the bombing raids, and she remembers growing up surrounded by rice fields and mountains. It was in Japan that Hiroko met Bob, a third-generation San Diegan, in the late 1960s, when he was stationed there with the Navy.

Among his possessions at the time was a tennis racket. Inherited from his father, who died when Bob was 11, this racket changed the trajectory of his life: He played constantly, filling up his school days, afternoons, and evenings on the tennis court. He was one of the highest-ranked teen players in the state, and he dreamed of joining the international tournament circuit after his stint in the Navy. But—speaking plainly—he acknowledges that he wasn’t quite good enough to compete with the best of the best. So, instead, he modified his dreams. He and Hiroko returned to San Diego in 1968, and he took a job as the club pro at Morley Field. By their mid-20s, in lieu of touring the world on the tennis circuit, the couple was running the club’s tennis store.

They spent 11 years at Morley Field, which at the time was one of the city’s tennis epicenters, hosting major tournaments for juniors. When the city handed over the store lease to a wealthier applicant, the Rays took over the property on University Avenue and moved in their tennis gear. They have been there ever since—through the McEnroe and Navratilova and Evert eras; the rise of Agassi and Sampras and Graf; the reign of the Williams sisters; the Federer-Nadal-Djokovic rivalry; and into the Alcaraz era. In the near-half century they have sold tennis gear in Hillcrest, the Rays became beloved anchors of the neighborhood’s business community, symbols of stability in an ever-changing environment.

At 84, Bob is still lean and, in his Lacoste tracksuit and Adidas cap, remains every bit the club pro. Like Hiroko, he comes to the store every day—though sometimes, if he is playing tennis in the morning, he might arrive a little later.

But time has started to take its toll. His hearing isn’t what it used to be, and the aging process is revealing itself to be true. And much to the disappointment of their loyal clientele, San Diego’s “First Couple of Tennis” is retiring, a milestone that marks the end of an extraordinarily long chapter in the city’s tennis history.

But Ray and Hiroko didn’t sell the building to a developer for condos or to a big-box retailer looking to open a boutique outpost. Determined that Ray’s should remain a tennis temple, they have negotiated a sale to a former employee who wants to continue the Rays’ legacy.

As of this writing, Hiroko and Bob remain in charge, Hiroko stringing rackets, Bob sharing his expertise about new gear. As much as they love what they’ve built, their hope is to move on soon.

For Hiroko, the prospect of retirement is bittersweet. “What am I going to do?” she asks. “Am I going to be ok? I never had a boring life. Always busy. Business first. I’m so involved in the business—because I didn’t want to fail.”

She looks around her store as she continues stringing. For her, the gladiatorial nature of tennis has always been a metaphor for how to succeed in life. “People have to have a drive,” she says. “You can’t just quit because you lose to so-and-so. Tennis players have that mindset.”

She pauses to talk about all the people who have come through the store’s door over the decades, and the relationships she has built with them. “It’s wonderful to have a great customer. That’s probably the reason I lasted this long.”

At the 1996 Atlanta Summer Olympics, Dane Chapin had a problem. He found himself in possession of tens of thousands of excess Monopoly games, with no plan on how to sell them. What he didn’t know at the time is that this Herculean task would shape the future of his business.

In 1994, Chapin and his sisters started their Carlsbad company, USAopoly, with a two-year license from Hasbro to make city editions of the popular Monopoly board game. “The game is a great canvas,” Chapin remarks. While some aspects of the game are “sacrosanct,” according to Chapin—the four corners, for example—many of the details can be customized to fit a theme.

USAopoly appealed to local customers by including San Diego and La Jolla editions in the original six games it created (alongside New York, San Francisco, Boston, and Atlanta versions). The tokens of the San Diego board included a surfer, a beach cruiser, and a copy of the Union-Tribune. Instead of Park Place or Reading Railroad, players land on the Gaslamp Quarter or the San Diego trolley. But after two years of city-specific boards, the siblings were ready to branch out.

In 1996, Hasbro gave them license to create an Olympic edition of Monopoly to commemorate the Atlanta games. The Olympic Committee had agreed to purchase 20,000 copies, a huge number for USAopoly in those days. They decided to manufacture 35,000, figuring they could sell the extra 15,000 on their own. The games went into production, but the Olympic Committee hadn’t actually sent over a purchase order.

“I finally get the buyer on the phone,” Chapin recounts. “And she says, ‘We’re going to order 90 games.’ Nine-zero. Not 900, not 9,000, not 90,000. Ninety.”

When he reminded her of the initial request for 20,000, she said that the team had changed their mind. “There was no point for me to get angry or get mad at her,” he adds, laughing. “I just had to figure out what I was going to do.”

Chapin landed in Atlanta for press coverage the week before the opening ceremony. “The Olympics are a white-hot deal, and then it’s done,” Chapin explains. “And once it’s done, there’s really no market for all those goods.” So, he shipped 20,000 games to the city. If nothing else, he’d have them on hand to replenish the stock for local stores. But, while Chapin was walking to an interview with an Olympic Monopoly board under his arm, a man stopped him on the street and asked where he bought it. Chapin sold it to him for 20 bucks. A lightbulb went off.

“We’re sitting with a warehouse of 20,000-plus games that need to find a home,” he recalls. Why not get them directly into consumers’ hands? He rented a van, bought a dolly, and got to work. “I spent the next two weeks on the streets of Atlanta, schlepping games,” he says. At the end of those two weeks, all the boards had been sold at $20 apiece.

Hasbro never knew the full story. But the company did notice how successful the Olympic board had been—and it was all the proof it needed to increase USAopoly’s licenses. “That was the inflection point for USAopoly,” Chapin says. “After that, [Hasbro] expanded our purview, our grants, well beyond city editions.”

Chapin and his sisters started to create pop-culture versions of Hasbro games, producing tributes to everything from Harley-Davidson to Metallica to The Simpsons. Now, three decades later, USAopoly (also known as The Op) is on track to sell over seven million games this year. It’s grown into an international family entertainment company that designs original best-sellers like Telestrations and Flip 7 in addition to twists on the Hasbro classics.

Peek in the archives at the Carlsbad offices, and you find shelves jam-packed with a copy of each game the company has produced since its inception, from the Atlanta Olympics Monopoly that changed USAopoly’s fate to Dragon Ball Z chessboards and RuPaul’s Drag Race Clue.

Chapin shows off the original San Diego Monopoly, still sealed in its packaging. “Think about some of your fondest memories in life,” he instructs. “My fondest memories include going to my grandparents’ house with my brother when I was 10 years old—we’d have a sleepover and play canasta for hours. Talk about joy, laughter, and lifetime memories.” He smiles. “So, that’s my job—to create games that will do that, that will bring people together and get them to put their phones away. It’s pure, and people can be present. That’s more important than ever.”

Fifty of San Diego’s top women founders, CEOs, and CFOs gathered on the lawn at the Fairmont Grand Del Mar on Thursday, March 27 for an evening of wine, local food, and unfiltered conversation about leadership, mentorship, and the messier parts of ambition. 

Hosted with J.P. Morgan for International Women’s Month, the event featured locally sourced bites by chef Flor Franco and pours from three woman-owned Baja vineyards, curated by Michelle Martain, owner of La Mision Wines and Cavas Valmar. The cocktails were cheeky, the sunset did its thing, and the energy was unmistakably electric.

“Stop asking yourself if you should be there—you’re already there,” advised Desi Swanson, CFO of Vuori and one of the evening’s speakers, when discussing young women facing imposter syndrome. When asked about the moment she knew she “made it,” she referenced a pre-Vuori memory from her 20s of paying off credit card debt and proudly walking into a boutique to buy herself a bee-shaped necklace she had wanted for months. That moment—vulnerable, personal, triumphant—set the tone. Success doesn’t happen in one moment; it’s the culmination of hundreds of victories throughout your life. 

Curie founder and mom to a new 10-week-old Sarah Moret discussed building her brand while challenging the myth that entrepreneurship is a man’s game. She also relived a time when businesswoman and investor Barbara Corcoran sniffed her armpits on national TV. (Yes, really.)

The conversation that followed felt real and unscripted. The panel shared their thoughts about what success looks like now, how mentorship shapes growth, and how to lead without losing yourself in the process.

My husband and I acquired San Diego Magazine three years ago because we wanted to invest in our local community, and create a platform for people and businesses to tell their stories. Events like this continue to prove that for all the stories that have been told, San Diego is full of thousands who haven’t… yet. 

During the networking hour, Nancy Schmall, CFO of Southern Pride Trucking, talked about the rise of women and married couples in the industry and how it’s reshaping truck stop culture across the country. Later, I spoke with Abby Blunt, co-founder and CEO of MeBe, an organization that offers personalized, evidence-based therapy for neurodivergent kids and families.

I even swapped parenting stories with Kerri Kapich, COO of the San Diego Tourism Authority, and told her about my dream of producing a fashion show in this city. Our photographer shared a hack she discovered with the CFO of the Aloha Collection to transform one of their staple bags into the perfect diaper bag. 

These women collectively manage thousands of people, steer massive budgets, and help define what work, leadership, and balance look like in San Diego right now. They’re building businesses, raising families, mentoring the next wave—and they’re doing it on their own terms. The story of a city should be told by the people living and breathing it every day. Each woman on that lawn owns a piece of San Diego’s story. And thousands more are out there, quietly building what’s next. 

Stay tuned for more events like these.