We’re used to hearing about retirement as a finish line – a moment to step back, slow down, and fade quietly into leisure. But for a growing number of people, the prescribed retirement age isn’t a deadline, it’s a doorway. In this continuing series, we meet the people who are rewriting the script on aging – and ultimately proving that, sometimes, the most meaningful work begins when everyone else thinks it’s time to stop.

Sheffman at her daughter’s wedding wearing an Isabel Marant floral dress. |  Lori Waltenbury/Courtesy of Sheffman

Meet Susie Sheffman, who juggles a trio of careers, a full-calendar of hobbies and hands-on family time. No day is typical: she can be found working with clients on their wardrobe while fielding calls regarding a house sale before heading out to a pickleball match. “I have this fabulous retired lifestyle, but I work full time.” Here’s how she does it all.

Images clockwise from left: Wearing her long time favourite Marni skirt with Prada cardigan at her daughter’s wedding breakfast; fashion illustration of Sheffman in her go-to stripes by Monica Smiley; Photographed for the Toronto Life best dressed list in a Joe Fresh shirt, The Row jacket and Brioni horn necklace. Rocking a hard hat at a condo site visit. | Toronto Life photo Felix Wong/Courtesy of Sheffman

HOME BASE: Toronto

HER MANTRA: “I work my retirement into my every day.”

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HER PASSIONS: “I have wildly high energy. My activities are a crucial part of my day. Monday tennis, Wednesday dance, weight training three times a week, bike rides, pickleball, canasta, mahjong, singing, my grandkids, my 95 year-old mother. I developed these hobbies later in adulthood. Work and play can co-exist.”

THE PIVOT: She still takes on fashion clients, but real estate has become her main gig now six years into her career transition. For 40 years, I had the job a million girls would kill for: fashion editor, stylist, creative consultant, going to the shows and shooting in fab locations. But I saw the writing on the wall as budgets diminished and the landscape was changing. The glam was gone, and with everything appearing instantly, the kind of timeless image creation I loved was disappearing. But not working was not in the cards for me. So I went from the fashion business where everyone sucked up to me to real estate, which is a totally different world: “No” becomes a starting point.” 

MILESTONE MOMENT: “Going back to school at 60. It was brutal, and it was a really forced discipline. The math was out of control! I was so terrified – trauma from being told as a kid I was no good at it – but in the end, I was so empowered because I forced myself to understand it. People in my class were calling me to explain it!”

IDENTITY SHIFT: “At first, I wanted to stay close to my old life, my old identity. But now I see the connections and I don’t think about that at all.” Today Sheffman is an agent and part of the S Team, with her childhood best friend, Terri Sapera, part of the Johnston & Daniel real estate brokerage. “It is not only about making homes look pretty. It is trying to matchmake people and homes, being resourceful and tenacious. I love the thrill of the hunt, particularly for off-market homes.”

 

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SEWING THE THREADS TOGETHER: At the end of the day, Sheffman realized that all of her career shifts have involved sourcing. She still does closet reorganization with private clients, under the name Closet Confidential (@ssheffman). “Within two seconds, they are in their underwear in front of you, it is extremely vulnerable.” So too it is with real estate: “You go into someone’s home, their inner sanctums, their bedrooms and bathrooms, it is a very intimate experience.” Working on photo sets for so long, she realized her role was to create an environment where people feel comfortable. And more: “my skill set has been to inspire desire, whether that is storytelling through fashion and photography or matchmaking people to beautiful homes.”

At her 67th birthday bash on Georgian Bay’s Tiny townships beach with her grandchildren. | Courtesy of Sheffman

BIGGEST PRIDE AND JOY: “My three grandchildren. I work hard to stay in shape so I can really be hands on, get down on the floor and play. I spend every minute with them whenever I can. That part of my schedule is non-negotiable.”

HOW SHE DOES IT: Starting early in the morning helps. “Thankfully, a lot of my clients and colleagues get up early too. 6:30 to 7:30 a.m is the superhighway of my day. That way I can pick up my grandkids from daycare. Also, when I am working, I am super focused. I truly don’t believe my work suffers. And I will not go to bed if my work is not done.”

Wearing her favourite tomboy staples of distressed jeans with a white t-shirt topped off by a tweed Comme des Garcons blazer, Victoria Beckham pinstripe vest and her beloved Miu Miu belt. | Jason Raposo/Courtesy of Sheffman