Cheryl Jessamine: Sunset adventures, with a mortgage calculator

Cheryl grew up in Forest Lawn, back when the corner store clerk knew your favourite candy, the city buses rattled by like clockwork, and twelve blocks of walking was just the warm-up for a good story.

Her dad was a firefighter, her mom sold Avon, and Cheryl? She and her brother found plenty of ways to stir up mischief, though, as Cheryl laughs, “My brother wasn’t as good at covering his tracks.”

In recent years, Cheryl’s life has been a careful balancing act: equal parts momentum and meaning. Between raising a family, cheering her kids on as they built careers of their own, and stepping fully into a new chapter herself, she’s found a rhythm that feels entirely hers.

After years in pharmacy and working in post secondary education in Alumni and Development, she made the leap, turning a long-held interest in numbers and people into a full-time career in mortgage brokering. And it clicked. The pace picked up quickly, the referrals rolled in, and Cheryl found herself exactly where she was meant to be: helping others find their home.

For Cheryl, that place is now Cochrane. She settled into Sunset Ridge in 2020, a neighbourhood that, much like Forest Lawn once was, sits on the edge of town but right in the heart of her day-to-day life.

She shares it with her partner, Cynthia, who recently retired after a long career in payroll, working across a variety of industries. The two share a love of the open road. Whether it’s a mapped-out motorhome trip or a spontaneous flight south, travel is something they both value.

Family has always been at the centre of Cheryl’s world, even as the kids have grown, moved out, and built lives of their own. Her daughter Rebecca works in human resources for a drilling company and turns 30 this fall. She’s engaged to Phil, a helicopter traffic reporter for Global News, with a wedding planned for September 2026. Her son Dylan, now 31, is an apprentice automotive service technician at Fifth Avenue Volkswagen. Her stepson, Eli, works as an electrician in Fort Mac, and of course, the granddog.

When she’s not working or packing for the next trip, Cheryl leans into the kind of quiet that feels earned. She reads: mostly fiction with a good storyline, but she’s also drawn to the kind of self-improvement books that make you pause and think. Her screen time? It’s curated.

She’s a loyal viewer of Survivor and The Amazing Race, partly for the gameplay, but mostly for the landscapes. Below Deck makes the list too, though she’ll tell you it’s the destinations she’s after, not the drama. House Hunters International scratches that same itch: seeing how people live, dream, and make homes all over the world. And when it’s time to slow down, it’s something like North of North on CBC that draws her in.

These days, Cheryl is exactly where she wants to be: on the move, surrounded by family, and always up for the next great adventure. Whether she’s planning a getaway or laughing with her kids over dinner, life is full.

She’s incredibly proud of the people her children have become, and even with the heartache of losing both her parents in recent years, Cheryl carries their legacy of warmth, strength, and humour into everything she does.