From Office Escapee to Freelance Feathered Flyer: How Rachel Dunlop Thrived Outside the 9-to-5 Grind

Rachel Dunlop, the millennial maverick who boldly bid farewell to the corporate world rather than succumb to the return of in-person work, found herself soaring high as a freelancer. After transitioning to freelance during the pandemic, Dunlop, a 39-year-old Toronto resident and copywriter, discovered a newfound love for the flexible lifestyle.

“There are just way too many benefits to this way of life,” she cheerfully exclaimed to Insider.

Dunlop’s journey into freelancing began when hints of the impending return-to-office atmosphere reached her previous full-time job. Working in a communication department at a social and athletics club, she endured a tiresome daily commute of one to one-and-a-half hours via public transportation.

“I never want to get on a rush hour subway car ever again,” Dunlop declared. “I never want to put on a business casual suit ever again. I never want to line up to use the microwave at lunch in a shared lunchroom ever again.”

Fortunately, the pandemic compelled a shift to remote work, which proved to be a dream come true for Dunlop. “In a way, it was kind of like all my dreams came true overnight because, for a while, getting to the office had been really difficult,” she revealed.

The absence of a daily commute was just the tip of the iceberg when it came to the advantages of working from home. Dunlop enthusiastically explained how her work life improved on multiple fronts during this time. She found herself happier, bidding farewell to the dreaded “Sunday scaries” and embracing the luxury of waking up later.

However, looming uncertainties clouded Dunlop’s newfound bliss. Concerned that the remote work arrangement would come to an end, she decided to approach her boss about the future. Unfortunately, her fears were confirmed when she learned that a full-time return to the office was inevitable. Determined not to succumb to the grind, she took a leap of faith and resigned in 2021, even without another job lined up.

“At that time, I was fully expecting to get another traditional 40-hour-a-week job,” she recalled. “In my mind, freelancing was just like a fallback.”

Little did she know that her decision would lead to a life of blissful unstructured freedom and financial growth. Inspired by an Instagram reel highlighting freelance success stories, Dunlop ventured into the world of freelancing on Fiverr. To her amazement, she discovered how much this career path could support her life.

Comparing her previous salary to her earnings in her first full calendar year as a freelancer, Dunlop estimated a substantial increase in income. Her writing jobs on Fiverr, such as crafting product descriptions and article content, start at $100 or $125 per project.

Now working from the comfort of her condo, Dunlop revels in the perks of freelancing. She relishes the flexibility to work when she’s most productive, experiencing bursts of inspiration even at 9:30 in the evening.

Creating drafts, conducting research on clients’ brands and fields, and ensuring a good fit with clients are among Dunlop’s responsibilities. Although some skepticism arises, particularly from clients new to hiring freelancers on Fiverr, the satisfaction of surpassing expectations and dispelling doubts brings her immense joy.

Working with diverse clients, including fitness coaches and jewelry designers, is a source of delight for Dunlop. After enduring repetitive work within a structured corporate environment, she now revels in the excitement of each unique day.

“My life is blissfully unstructured now,” she chuckled.

While freelance work wasn’t initially a fit for Dunlop back in 2013-2014, her preferences evolved over time. As circumstances aligned in 2021, she made the switch to freelancing full-time, and everything fell perfectly into place.

Have you also bid adieu to your job or embarked on a new career due to return-to-workplace requirements? Share your story with this reporter of the ROOST at


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