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She’s a Toronto Legend, Model, and Style Icon. And She Was Nearly Homeless

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Wealthsimple is an investing service that uses technology to put your money to work like the world’s smartest investors. In “Money Diaries,” we feature interesting people telling their financial life stories in their own words.

When I left my last career — working in retirement home administration — I was nearly 70 years old. And at that time of life, you just want to put your feet up, you know? I’d gotten rid of most of my earthly belongings and I thought I was going to go out west to live with my daughter. One day, walking down the sidewalk in Toronto, a young man on a bicycle stopped and asked, “Can I take your picture?” He had a street style Instagram account, and it seemed like age was trending. I said yes. We found a wall, and the wind blew my coat open just as he was taking the shot. Unbeknownst to me, he sent it to National Geographic, and they picked it as their shot of the day. That was five years ago. I’m 74 now and I have about 20,000 Instagram followers. I was nominated for model of the year in Canada this year. It was the first time anybody my age had been nominated. I think being acknowledged a little in the industry has made the struggle (and, yes, there has been a struggle) feel more honourable.

I’m not shy about retiring, either, though. When I turned 60, I bought a pair of Cesare Paciotti boots. They have a red sole with a dagger on them. They are six inches tall, and I can still walk in them. I remember going to a Blue Jays game when the New York Yankees were in town. I grew up loving the Yankees because my father loved them. I had somewhere to go afterwards, and I thought, what’s the point in changing? So I just showed up in a red Valentino evening gown at a stadium where a bunch of people were wearing tracksuits. I was cheering for the Yankees, so I stood out even more. A woman in front of me turned around and asked, “Why are you wearing that evening gown?” I said, “Because it makes me happy! Why are you wearing pyjamas?”

I am hopeless with money. I have a love-hate relationship with it. I know I need it to live, but everything in my life — it’s all based on love.

But I never set out to be a model. I dislike having my picture taken, and I didn’t want to be on social media. A few days after the National Geographic picture, my goddaughter said, “Do you think it’s a sign that you’re supposed to be a photographer? Because God knows you can’t start modelling at 70.” She told me I should get an Instagram account. I said, “Oh God no!” But the next time I looked at my phone, I saw that she had started an account for me. So I began to post on it. Three weeks later, a magazine editor at ELLE Canada called. She wanted me to play a grandmother in a wacky family photoshoot. I said, “Are you paying me?” And she said yes. I put on an Issey Miyake coat and some red lipstick. That day, the photographer told me, “The camera loves you so much it could take the picture without me.”

For the next two years, I just sort of answered the phone. I did a ton of modelling work without even having an agent.

But at the same time, those years were very difficult. I had pneumonia twice. I got maybe $1,000 a month as a pension from the government, and was almost entirely paid in products and gratuity for modelling work. I had chewed through my savings not long after I retired. I am hopeless with money. I have a love-hate relationship with it. I know I need it to live, but everything in my life — it’s all based on love. I don’t plan, I don’t worry about the future. I was raised by wonderful parents who were frugal. We didn’t have much when I was a little girl. One Christmas, I asked my Papa if I’d get presents that year. He said, “If Santa cuts a lot of hair!” He was a barber. All through the Great Depression, he traded haircuts for food. While I was modelling, I was renting rooms in the city. Once, my clothing was stolen from one of those rooms. My daughter kept saying, “I’m coming, we’re packing up the van and you’re coming to my place.” But I’m terribly stubborn.

I was thrifty. I walked across the city to auditions. When I had nowhere to stay, I stayed with friends, looking after their cat. We call it couch-surfing. But the truth is, had I not had my daughter, who helped me a little bit, I would have been on the street. I didn’t have a permanent address for three years. Do you know how crazy that makes the government? The tax agency calls me now. I say, “Young man, if you watch me on Instagram, you’ll know exactly what I’m doing.” I’m sure they watch me on Instagram. I told them they should!

A woman in front of me turned around and asked, “Why are you wearing that evening gown?” I said, “Because it makes me happy! Why are you wearing pyjamas?”

Last year, an agent phoned me and said, “Adidas has reached out to us to scout you for a shoot. And when you’re finished with that we’re going to scout you for our agency.” I said, “I’m not a model.” And he said, “Well, we think you are.” I decided to sign with him.

That’s when I began to actually be paid for modelling. But the money is unpredictable: sometimes you don’t get paid for three weeks or six weeks or nine weeks. I went to an audition last Friday, for I knew I’d get a callback. It’s just got to do with the energy. I come in like someone who just blew in from another place. I got to play a palm reader!

And that’s fitting because my life is magic. I walk step-by-step with no concern for the future. Six months ago, a friend of mine who’s a designer phoned. He said, “Jude, I need your help, will you come to the textile store?” I said OK, and I went looking for material with him. He told me about a space he’d been offered that was available for rent. He wasn’t interested, but he thought I might be. He put me in an Uber and I went to see it. The woman who was renting it said, “If you can get it together, you can move in tomorrow.” I phoned my agent, and said I might have found an apartment. I told him I needed first month’s rent, $1,800, and then I had an apartment. I’ve been here six months now. It’s my first permanent address in three years. There’s a beautiful fridge, stove, and sink. It’s so cute! It’s lovely. I have a back door, that opens out onto a parking lot where ambulances park overnight. My daughter laughs about that. “Well, you’ve got no end of rides if you need one!” she says. People send me things all the time, scarves, and handbags from Dubai, and five pairs of stilettos, and Japanese kimonos, and jewelry, jewelry, jewelry. A pair of earrings came in the mail recently, in a beautiful box from Paris.

I go to visit my friends in their retirement homes now, and they say, “Why are you like this?” My mother used to say, “Make sure your path is full of rainbows,” and it really feels that way. The blessings of life are always with me. I’m not here for a long time but I’m here to learn. And if authenticity is the currency, I consider myself extremely wealthy.

As told to Katherine Laidlaw exclusively for Wealthsimple; transcript edited and condensed for clarity. Illustration by Jenny Mörtsell.

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