Despite countless reports to the contrary, the “entitled” Millennial generation doesn’t expect to be handed the keys to the executive suite.

Millennial Job Prospects
CASE STUDY A
Name: Tammy Uppenborn
Age: 35
Profession: Occupational therapist
In 2007, Uppenborn got her Master’s in occupational therapy. She assumed there would be no shortage of work in a field tied to healthcare and the rapidly aging population. But government cutbacks and a shift away from in-patient hospital care proved a game-changer for the profession—and for her.
She found work, just not the sort she had envisaged. For five years, Uppenborn has completed a series of short-term contracts at various Toronto healthcare and rehabilitation facilities, serving as a perpetual stand-in for employees on maternity leave or vacation.
Despite hoping each contract would lead to a permanent job, her longest stint at an agency fell just shy of a year.
Uppenborn has never received health benefits, nor had an employer contribute to her pension. Employers require that she pay into an Employment Insurance fund, but regulations around temporary work prevent her from accessing EI during the scary months between jobs. Having recently started an eight-month contract at a new agency in Guelph, she will again be left scrambling for a new position this winter.
“I’m always on the steep end of the learning curve, always putting in extra, unpaid time, because I want to look good if another position opens,” she says.
Contract work has caused her anxiety, and thrown off her plans to start a family: “I can’t go on maternity leave because I don’t have a permanent job. But I’m going to be 36 this month. Like, tick tock!”
CASE STUDY B
Name: Cameron Jones
Age: 29
Profession: Legal researcher
Like many who slog through law school, Jones (not his real name) recalls holding lofty expectations prior to his 2008 graduation: “I thought, My future’s made. I’ll finish law school, get an articling position, and move into a permanent job.”
Then, like many of his peers flung from the cozy academic bubble mid-recession, Jones faced a harsh reality. He spent five months looking for work, followed by six months doing piecemeal legal-writing gigs and short-term contracts. He remembers the irony of one company referring to him as an “independent contractor.”
“I was an employee,” he clarifies. “I came into the office every day, I perfected the work I was told to do. There just weren’t benefits.”
Eventually, Jones secured stable legal work, a feat that may become increasingly difficult to achieve for Ontario law graduates, in light of the province’s shortage of articling placements. This year, nearly 15 per cent of them couldn’t find articles—a prerequisite for becoming licensed.
CASE STUDY C
Name: Aafreen Malik
Age: 30
Profession: Teacher
Malik (not her real name) has worked as an occasional teacher for six years, alternating between day-to-day supply work and, when she’s lucky, maternity contracts. She has vied for a permanent position with the Toronto District School Board, but to no avail—openings are usually snapped up by transferring teachers.
“You’re often not respected by colleagues and the administration as much as if you were a permanent teacher,” she says. “I’m not going to be there in a couple months, so it doesn’t really matter [to them] to keep me happy.”