The eternal question: “Where’s home?”

By Caitlin Kelly

Once you’ve changed cities, towns, states/provinces, let alone countries a few times…you can feel quite deracinated, literally un-rooted.

My therapist (oh, that NY cliche!) is from South Africa. Like me, she came to the United States as an adult, and returns to her native country when she can.

Every time we do, we confront our “parallel life”, the one we might have had if we had never left. How (more? less?) successful would we have been? In Canada, with smaller, tighter professional networks, likely…one former university friend now runs the CBC. Another was the speechwriter for the Governor General.

In New York, I have a pal who was the speechwriter for a New York governor, his brother a best-selling novelist. A woman I idolized there professionally at 26 and a writer whose work I read when I arrived are now…Facebook friends. My much shorter reach in the U.S., socially and professionally, came as a real shock to me. I don’t desperately care about it, but it’s very different when your home country has 10 percent of the U.S. population!

I’ll be in Toronto for eight days starting this weekend, and seeing old friends who have never lived elsewhere, apart from one outlier whose wife told him the marriage was over — while they lived in Indonesia.

The elegant lobby bar of Toronto’s Royal York Hotel

I never loved Toronto, my home city, one very much of home ownership, whose expensive, often run-down rental properties are a real thumb in the eye of those of us forever outbid on any house we even tried to buy. Today even the ugliest tiny teardowns sell for — no kidding — $1 million or more. They’re of a size and quality you might consider paying $300,000 for if you were generous. By the time I left at 30, I was restless. If I couldn’t buy a home and settle, time to go!

The city has gorgeous parks and some terrific culture, but after 25 years there I was hungry for change.

Being (cough) opinionated and direct since my teens — neither applauded as politely Canadian — would likely have foreshortened my career since there are so few major cities. I’d already lived in Toronto and Montreal and Ottawa, Calgary and Vancouver didn’t appeal. So I was lucky to get a green card and legally emigrate to the U.S.

But, oooof, it’s not easy! I’m glad I came and have achieved many of my personal and professional dreams in New York: published 100 times by The New York Times, two books, a lovely second marriage, an attractive apartment. I felt I would likely not have achieved most of these had I stayed in Canada.

I recently did a podcast and one of the questions asked about my romantic life. It was messy and complicated in my 20s since I knew I wanted to move to New York eventually , which meant always dating Mr. Right Now and never Mr. Right, a potential life partner who wouldn’t be able to go with me or probably wouldn’t want to.

So that romantic frustration was another spur to keep moving. He had to be out there somewhere! (I met my first husband in Montreal, introduced to me by a friend there. He was from New Jersey and soon to move back to the U.S.)

Like most people who stay and thrive, most of my Toronto friends are doing very well professionally, have raised families, bought property. Some still head north to their family cottage, some arriving by boat. It’s deeply Canadian!

I don’t even know how to drive a motorboat…

When you leave your native country behind, you also leave behind the former you…the younger, more hopeful, likely more naive version. That’s part of leaving — if you were so delighted by home, you’d stay.

But you do get to spend more time with the people who “knew you when” and can revive some lovely memories. A very dear friend from high school told me last year he had been struck by how “progressive” I was, even at 17.

I recently had dinner in Manhattan at the legendary deli Katz’s (the one from “When Harry Met Sally“) with a younger writer who lives in a small Florida city. She finds NYC a source of creative energy, which I agree with. I told her that living/working in New York City (even though I live nearby) forces you to be fearless, whether dating, driving, looking for work or seeking friendships. Holding back and shuffling your feet there gets you nowhere!

I admit it, I like that element. Sometimes you have to leap, however terrified, to grow and change and hit the heights you seek. I always find very quick shared connection with people — at any age — who have uprooted and lived (sometimes very far) far away from their early homes. That forced adaptation, I think, opens you up to all sorts of new possibilities and identities — staying in a place where “everyone knows you” can feel a bit stifling after a while. I know I never would have studied interior design in Toronto, which I adored, as I did in New York City.

It happened to me at 25 when I spent a fellowship year in Paris.

That’s me in the stripes, around age 8, for a magazine story on kids cooking

I’m definitely a smarter, wiser, tougher version of myself for having moved to New York; as my lovely (second!) American husband has said to me whenever I get wobbly: “Now is not the time to be Canadian!”

When I visit Canada, I do have to dial it back, or apologize for being the “bossy New Yorker.” The things I’m proudest of in NY don’t really register with my Canadian friends, who don’t know these people or haven’t had to compete at those levels. That sometimes feels painful.

The “what if?” question is one I suspect haunts every immigrant, but especially if you’ve had the luxury of leaving a civil, thriving place, not fleeing war or persecution.

Have you changed homes a lot?

Do you have a “parallel life” elsewhere?

Does community matter?

The Nova Scotia house I had hoped to buy, in a small coastal community. That both attracted me and made me nervous as an outsider.

By Caitlin Kelly

Interesting op-ed in the NYT, on why we all (he thinks) need community:

We are stronger and more robust when enmeshed with others in community. But in our age of autonomy, efficiency, boundaries and self-care, we too often deprioritize, if not overlook altogether, the wellspring of strength and meaning that comes from obligation.

For people to really know us, we need to show up consistently. Over time, what starts out as obligation becomes less about something we have to do and more about something we want to do, something that we can’t imagine living without. The spiritual teacher Ram Dass once wrote that “we’re all just walking each other home.” But that’s only true if we don’t constantly cancel our walking plans.

Not canceling plans means, essentially, showing up for one another. If we commit to certain people and activities, if we feel an obligation to show up for them, then it’s likely that we will, indeed, show up. And showing up repeatedly is what creates community.

We know Americans are really lonely.

We know many have given up on troubled institutions like church, synagogue, Boy Scouts, etc.

I live in a suburban New York town of about 10,000 people, and have for decades. Technically, it’s my community, insofar as it’s where I live.

But I still know only a handful of people, and mostly those we buy from — the hardware store and local restaurants.

Having spent decades in the same apartment building, where we own our homes, this is really my primary community. I know who’s recently widowed, who’s off to a cruise in Alaska, who got (!) tickets to Taylor Swift, whose baby has her first birthday this month.

We have few ways to connect beyond a pool party — which was fun and drew about 25 residents. Looks like I will join our book club.

The definition the author uses, though, is obligation…not just being around other people when we choose but something we commit to.

One of my favorite recent films, Marcel the Shell, includes a powerful moment when Marcel — grieving the sudden flight of all his relatives to an unknown place — suddenly becomes massively popular on the Internet, with strangers posing for selfies on the lawn of the house where he lives.

He really wanted help finding his lost relatives, but all he gets is unwanted attention.

“I need a community — not an audience,” he laments.

I admit, I’ve never been a joiner.

Partly it’s my nature and partly the culture of journalism — we are meant, always, to be impartial observers, not eager members of any party (certainly not political.) It’s forbidden in some newsrooms.

My journalism pals are also my community, now mostly online, but an important source of advice and friendship — I served six years on the board of a journalism group and made deeper friendships as a result of that volunteer work.

I have had less success at the church I first entered on Christmas Eve, 1996, in crisis. At times, it has offered tremendous support, but more from a few close friends and caring pastors than the larger congregation — a white, wealthy, corporate crowd. Very much not who I and my husband are. That inhibits me from returning and making deeper commitments there.

Are you a member of a community?

What and why?

Planning a vacation

Baie-St-Paul, Quebec. November 2022

By Caitlin Kelly

It’s de facto a privileged thing to discuss!

Vacations cost money, even if you’re camping (you might want a tent or a portable stove and lantern and chair and…)

As regulars here know, travel is really my greatest pleasure in life beyond cultural joys like ballet, concerts, theater, museums, which ready access to Manhattan affords us.

But planning a vacation, especially on some sort of a budget and without a travel agent, means doing a lot of research and that takes a lot of time to find and read multiple reviews of hotels or other venues. I am not an Air B & B user nor of VRBO but have considered joining Trusted Housesitters, which charges a fee to join, and gives members access to hundreds of appealing spots to house-sit, most in western Europe, usually including taking care of owners’ pets, which can include multiple dogs, even horses.

Last year’s big trip — which I blogged about here — and loved every minute, was a month’s solo drive from San Francisco (with a stop north in Santa Rosa to visit a friend there) to Los Angeles. Hotels were a challenge financially, and I ended up paying an absurd $300/night in Santa Barbara for a motel room. But, across the street, I also scored a great haircut for $55 and down the road a fantastic pedicure for $45 and there was an astounding indie bookstore there as well.

My favorite spot, by far, was in Big Sur, staying at Deetjen’s. The central coast, for me, was pretty boring after that.

I know some people, especially women, hate or even fear traveling alone. I love it! Have done it many times, never fearful although aware that danger can pop up anywhere. It’s rare to find a friend with the same taste/budget/schedule to travel with — although I have discovered a Texas pal eager to see the Northern Lights and a BC friend up for a warm winter break…

My teeny tiny room (shared bathroom down the hall) at Deetjen’s, Big Sur, June 2022.

I’ve been bouncing around all sorts of ideas for another June away — my birthday is June 6 — and it’s Jose’s busiest work month so being home is boring and lonely.

First thought: England/Shetland/Norway/home

Second: Helsinki/Tallinn/Riga/Lithuania/home

Latest: Paris/Helsinki/Tallinn/Helsinki/home

But I still haven’t booked anything!

Clearly ambivalent….but also recently beset and constantly distracted with too many friend/family deaths and other mounting family chaos.

Not surprisingly, many of my friends also love to travel.

They’re individually headed off soon to Paris, Patagonia and Corfu. I’d love to visit all of these, having been to Paris many times, never to Patagonia or Corfu.

I’m not someone for:

cruises or anything Disney or zip-lining or crowded/noisy places; I fled Venice in July with brutal heat and wayyyyyy too many people. I also recently saw a photo of a street in Mykonos — literally more crowded with tourists than the NYC subway at rush hour. No thanks!!

I speak fluent French and good Spanish, which makes me feel more relaxed when venturing to places where people speak these.

My happiest vacations typically include:

some very good meals

a night or two or three in a luxury hotel or resort

gorgeous landscapes

not driving!

some big city fun

a bit of shopping

some culture (museums, galleries, etc)

if solo, and often with Jose, catching up with local friends (I saw 11 of them in my California month)

I’ve been very lucky — between my family, first husband, Jose and work — to have traveled widely, to 41 countries so far:

Antigua

Bahamas

Montserrat

Jamaica

Colombia

Venezuela

Peru

Costa Rica

Nicaragua

I learned how to canoe at camp -- useful when we went to Nicaragua
On assignment in Nicaragua for WaterAid — Jen in the bow of a dugout canoe March 2014

Mexico

Fiji

Thailand

New Zealand

Australia

So fun to ride the upper deck of a double decker bus in London!

England

Wales

Scotland

Mais oui, c’est Paris!

France

The Netherlands

Belgium

Ireland

N. Ireland

Germany

Portugal

Italy

Spain

Croatia

Rovinj, Croatia, aka Little Venice, July 2017

Hungary

Bulgaria

Romania

the former Yugoslavia

Tunisia

Malta

Kenya

Tanzania

This NYC hotel is a hoot! You can lounge in a rooftop pool and watch jets taking off. We loved it.

the United States

Canada

Turkey

Austria

Denmark

Sweden

Still on my wish list:

Japan

Morocco

Jordan

Greece

Torres del Paine

the Amazon

So where am I going?

Hah! Back to my hometown, Toronto, for eight days — to see old friends, enjoy familiar sights and present an award I created at my old high school.

Jose and I have two weeks in Paris booked for late October — and if I save hard, I might still be able to see Finland and Estonia next June; I’ve been re-watching Deadwind, a three- season crime show set in Helsinki and rural Finland, which has also piqued my interest.

Do you have a vacation planned?

Dreams realized, dreams yet to be…

From the fantastic new sailing museum in Newport, RI. Have long dreamed of owning a sailboat. Big responsibility.

By Caitlin Kelly

With yet another birthday looming next week, it’s a good time to look back and forward.

In my 20s, I wrote in my journal I wanted to live in New York by the age of 30.

I had no idea how to make that happen!

And, yet, there I was…albeit 31 and in a lovely town 25 miles north of Manhattan.

I’m not, as you all know, much of a woo-woo crystals girl, but naming this desire must have tweaked the universe somehow. I was suggested as a great hire to the Montreal Gazette by a Globe and Mail colleague who knew I was getting restless and sick of Toronto after 25 years living there. I craved change and wanted to use my French skills and learn something of at least one other province.

So they hired me as a feature writer, which was not my dream job, but it is a dream job to have a weekly platform for long-form writing.

It was a big leap of faith and, in some ways, very stressful. I was now a five-hour drive east of all my closest friends who I thought, naively, might come to visit, and did not. I did have a spectacular sixth-floor/top floor apartment with two bedrooms and a working fireplace and built-in bookshelves, by far the nicest apartment I’d ever lived in.

I quickly met an American medical student, friend of a friend, and we fell in love. I followed him to New Hampshire and then to New York and….I was there by the age of 31.

Thanks to a family inheritance, I was able to realize the dream of buying my own home, and — many years later — I still live in the same apartment. Thanks to Jose, we were able to renovate the kitchen and only bathroom, both of which I designed, having studied at the New York School of Interior Design, which sharpened my eye and gave me skills and confidence for that work.

Luckily, after my brief two-year marriage and six years of being divorced (no kids) and often lonely, I met Jose and we have been together for 23 happy years. I had hoped for a happy second marriage but it’s nothing you can count on!

Other major dreams later materialized, writing and publishing two books of non-fiction with major NYC houses; I always get emotional with the very final scene of The Devil Wears Prada, as Anne Hathaway strides east to west on 6th Avenue right in front of the Simon & Schuster building where I sold my first book. I will never forget the exhilaration of exiting that building holding my galley (the unpublished version.)

I’ve sold more than 100 stories to The New York Times, been interviewed by one of the city’s top journalists on WNYC’s Brian Lehrer Show and by Diane Rehm on what was then NPR’s show with the largest audience.

I’ve taught here at Pratt, Pace and Marymount.

What’s left?

  1. We’re planning a photo/storytelling workshop in August 2024 in Charlottetown, PEI, Canada, with my husband Jose and photo legend Dave Brosha. It’s $2650 for the three days, about $2,000 U.S.
  2. An editor from Rolling Stone has asked me to pitch and I’m looking for great story ideas.

3. I still have so many countries I want to visit.

4. I’ve become a mentor with Report for America, helping individual young reporters as they navigate their early journalism careers

5. Will I ever own a house????? It really has been a lifelong dream, but I don’t know if it’s possible. We’ll see.

6. I’m going through my 1000s of images and hoping to sell some of them to interior designers, who always need interesting artwork for their clients. Had a very promising conversation recently with one potential buyer. I began my career as a photographer while in high school, selling three images as covers to a Toronto magazine and have since sold to the NYT, Washington Post and others. Fingers crossed!

It feels good to still have a few unrealized dreams, even later in life.

I think without them I would wither and be bored and depressed.

And you?