What began as a few adventurous years in Manhattan became a life. Eleven years later, Amy Louise Bailey reflects on chasing the American dream
The night I met my husband, we talked about moving to New York.
Neither of us had lived there, but we’d each spent time in
the city the year before – he’d travelled over after joining the Auckland office of Goldman Sachs; I’d been backstage with Karen Walker at New York Fashion Week.
We’d experienced very different sides of the city, yet each came home with the same conviction: that somehow, one day, we’d end up there.
A few years later, we married and, in 2015, boarded a one-way flight to JFK with five suitcases for what we imagined would be a few adventurous years abroad. Somewhere over the Pacific, I began to wonder if it was romantic or reckless.
Eleven years, four apartments and three children later, we’re still here. There was no grand design – only the belief, shared by millions before us, that New York might be the place to discover what you were capable of.
Amy Louise Bailey in her Manhattan apartment. Photo / Nela Kekic
I have always felt incredibly fortunate to have grown up in New Zealand. The more of the world I see, the more I appreciate how unique that childhood was: beaches a short drive away, grandparents nearby, friends whose families all knew one another, a sense of safety so instinctive I barely noticed it.
In New Zealand, there is always some faint web of connection, however indirect: someone knows your parents, remembers your school, once worked with your cousin. You don’t realise how rare that is until you live somewhere it simply doesn’t exist.
Perhaps that’s why leaving never felt like turning my back on home. Like many New Zealanders in their 20s, I was simply curious about what life looked like somewhere else.
For many of our friends, that somewhere was London. Others chose Sydney or Singapore. We always had our sights set on Manhattan.
At first, the anonymity was liberating. Nobody cared where I’d gone to school, who I knew, or what I’d done before I arrived.
In New Zealand, you’re always tethered to a kind of collective memory. In New York, you can reinvent yourself, try things on, and fail quietly without feeling observed.
Amy Louise Bailey’s Tribeca apartment.
There were practical shocks too. Apartments cost astonishing sums and somehow lacked things I’d assumed were fundamental – light fittings, for one. (Flight of the Conchords, it turns out, was less satire than documentary.)
Tipping turned almost every interaction into a small social test, and it wasn’t unusual for a single block to contain a film crew, a saxophonist, and someone arguing with a fire hydrant in their underwear. Before long, certain absurdities become part of the city’s rhythm.
Manhattan has a unique ability to expand your sense of what feels possible – professionally, but also personally.
Looking back, my 25-year-old self would probably say I checked every box. Within months I’d landed a director role at one of New York’s largest PR firms. Later came bylines in Vogue, Harper’s Bazaar, and major international titles.
I managed budgets that would have seemed comical by New Zealand standards, where a brand collaboration or an orchestrated paparazzi moment could easily run into seven figures. In New York, you quickly become fluent in the language of excess.
Mathew Harris and Amy Louise Bailey. Photo / Nela Kekic
My husband, now managing director, has his own version of that scale – one that can mean flying to Los Angeles for lunch, or another continent for less time than the flight.
Immigration was the harder lesson. I arrived on a spouse visa and spent long stretches unable to work while paperwork moved slowly through the system – especially difficult when our green card application was cancelled, just as I was preparing to launch an e-commerce business I’d spent two years and considerable savings building.
It was eventually approved, but that particular limbo is difficult to describe to anyone who hasn’t lived it: building a life somewhere you’re never certain you’ll be permitted to stay.
My European passport would have made London the easier route. By then, though, New York had stopped being an experiment. It had become our life.
Almost everyone here has arrived from somewhere else, and perhaps that’s why people are so quick to invite you in. Our building in Tribeca was full of young professionals from all over the world – bankers, lawyers, models, musicians – all trying to figure it out.
It felt like a modern version of Friends: there was always a dinner to join, drinks on the rooftop, someone persuading the rest of us downstairs for a workout, or a knock at the door that somehow became the evening’s plans.
Years later, in a different chapter, that instinct held. When I went into labour in the middle of the night, one text was enough for friends down the hall to come and stay with [our older daughter] Ella. In New York, friendship often begins with proximity. Ours certainly did.
Amy Louise Bailey and Mathew Harris with baby Siena.
Life here can be as routine or as cinematic as you want it to be. Most mornings revolve around coffee, work and the choreography of getting three children out the door.
One of my favourite rituals is taking open class at Steps, tucked above a creaking stairwell on the Upper West Side, filled with dancers who’ll perform at Lincoln Centre that night. It feels like a scene from Centre Stage and, as someone who almost traded my BA/BCom for a career in performing arts, it’s one of the reasons I love living here.
And if you want New York at its most dazzling, it’s always available. An afternoon wandering the Met. A rowboat on the lake in Central Park. Martinis around the piano at Bemelmans on any night of the week.
Amy Louise Bailey in her Manhattan apartment. Photo / Nela Kekic
The hardest part, over time, has become the transience. You find your village, build a life around it and then, gradually, people disappear. Careers take them elsewhere; families head home.
I look back at photographs from my 30th birthday and it’s sobering to realise how many of those faces are no longer woven into our lives.
The city is constantly renewing itself; friendships take much more work. For parents, it changes the calculation. You start thinking not just about what the city gives you, but what kind of community you want your children to inherit.
America has changed, too. We moved during an era when politics sat mostly in the background. Today the country is more divided, and there are aspects of raising children here that remain difficult to reconcile as a New Zealander.
Amy Louise Bailey visiting Queenstown in 2023.
Amy Louise Bailey’s children Siena and Marlow in Auckland on a visit in 2023.
Then there are moments that make the question of whether we will return impossible to ignore – realities I never had to consider growing up.
And yet there is nowhere quite like New York for teaching you to live with contradiction.
What I miss most about New Zealand is simple: my family and friends, the beach, the warmth of Kiwi culture. My mother remains my closest confidante and, although we speak daily, it’s never quite the same as being able to see her.
I watch Ella, Marlow and Siena in New Zealand and think about what it would mean to give them more of that life. I watch them in New York and think about what they’d be giving up.
Neither answer resolves comfortably and I’m not sure you ever stop grieving the version of your life you didn’t choose.
Eleven years on, I’m no more certain than I was somewhere over the Pacific.
Amy Louise Bailey is a writer and brand consultant based in Tribeca, New York. She contributes to Condé Nast Traveler, Bloomberg, Vogue, Harper’s Bazaar and is the founder of Antipodean, a new Substack for Kiwis navigating life abroad. She shares more from life New York on Instagram @amylouise_bailey.
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