By Caitlin Kelly

I had long dreamed of coming to New York City, starting in my teens.

My mother was born there, but never spent much of her life there, so it wasn’t her stories, more all the movies and images I saw growing up in Toronto, from the Woody Allen film Manhattan and Breakfast at Tiffany’s to every shot of the Empire State Building or Grand Central (Terminal, not Station!) I came to the city once with my mother and later came in my early 20s, once on my own and once (!) to perform eight shows as an extra with the National Ballet of Canada in Sleeping Beauty at Lincoln Center with Nureyev.

One visit in my 20s was peak, hard to beat. Typical of the era, I then had my journalism work, typed out on paper, stored in a large black portfolio case I brought with me for a meeting at Glamour magazine. I was so nervous and excited — their offices were then at 350 Madison, next door to Brooks Brothers. I left my work for them to read and (!) they wanted to buy one of my stories before it had even appeared in a Canadian magazine.

As if this wasn’t triumph enough, I met a very cute guy in the shoe department at Brooks Brothers who — yes, really — took me dancing that night at Studio 54. Oh hell, yes!

I bought my first Walkman in NYC and still remember exactly where, on Madison Avenue, I sat in awe and listened to a tape.

When I moved here with my first husband, then finishing his medical residency, I hit the worst recession in journalism. It took me six miserable months to find my first job as a magazine editor, and knew I would hate it, but I needed a job! I lasted two years and finally had a NYC resume addition that would make a difference. It was at 200 Madison, so every time I go to the Morgan Library I recall those days across the street.

I never lived in the city, always in a suburban town we could afford and enjoy a decent quality of life, even after that husband bailed.

So what turns an outsider into a New Yorker?

Chutzpah

For sure. Not being scared to say what you want, think or feel. Sometimes not welcome. But this is a place that often values directness, very different from Canadian polite passive aggression.

Seeing opportunity and jumping!

I know many people have a really hard time finding a foothold here. I did, too. But with so many people and so many potential opportunities, you have to be ready to see one and jump.

Confidence

Different from chutzpah — which is more about sassiness and boldness. I did not grow up here or attend schools here, unlike so many of my competitors in journalism. But I speak 3 languages, had savings and good health and a very good university education. I wasn’t scared to join the fray. Those who are just won’t make it.

Resilience

Oh yeah! Unless you’re super lucky and/or super connected, you will likely face plenty of social and professional rejection and disinterest as someone arriving from elsewhere, not educated at any level in the U.S. I was devastated, after early and significant success in Canada by my mid-20s, to be treated so carelessly when I arrived. I cried every day during the six months it took to find my first job. A tart NYT editor said “Don’t sound defeated. It won’t help.”

Great skills

New York will very very quickly humble you! The city is full of astonishing talent, so trying to compete with it, unprepared, will not be a great experience.

Charm

I think this is a much underrated attribute. Not being obsequious or oleagainous (and there’s plenty of it!) but being a fun, interesting and engaging person to be around. Jose has it in spades. I can do it when needed. It’s a refreshing change for many, and will be noticed.

Figuring it out on the fly

Whether driving or navigating the subway there’s always a breakdown or diversion. You have to be resourceful here and anticipate that there’s always going to be a screw-up — and you will have to deal with it.

Brusque doesn’t mean rude

We’re in a hurry! Don’t take forever to order at a deli or coffee shop or food cart. NEVER block the subway stairs or sidewalks. As Dustin Hoffman famously ad libbed in Midnight Cowboy, banging on a taxi hood: I’m walking here!

A quick wit

People joke with strangers all the time. Read the NYT’s Metropolitan Diary for some great examples.

Say what you mean

They value directness. So do I.

Savoring its best

The city is always too hot or too cold, too crowded, too expensive.

But then — you still have the harbor at sunset and the view from the Staten Island ferry and spring blossoms everywhere and amazing museums and galleries and theater and parks and two rivers and benches to sit and people watch and some great and historic bars and restaurants and shopping and history and architecture.

In the past month, I’ve gone slightly mad: seen La Boheme and Madam Butterfly at the Met and Project Hail Mary in IMAX on 42d street and Florence and the Machine at Madison Square Garden and lunches at Orsay and Nice Matin and dinner at PJ Clarke (all classics.) A huge gulp of it all. Have loved every second of it.

And there is always something unexpected — like the diner who casually parked her white tutu at P.J. Clarke before dinner.