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Upwork and I or 'How I got started freelancing online'

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I am Rachel Donovan and this is my story as a freelancer. During a lovely dinner with my partner, then fiancé she shared the good news with me, she had just gotten a job offer—a dream one. She’d been really hoping for it, but it was all the way in Toronto. We met, lived and worked in North Carolina at the time but were open to moving. The plan was to move to wherever either of us found a good opportunity. It was 2017, and at the time, I worked as an editor for a local newspaper. I had been there for 4 years and quite frankly a change was due, so I was more open to a move even without having an alternative source of income. Although, I hadn’t given it much thought so it came as a mild, but pleasant shock when she revealed the good news. I knew I had to get another job soon but I was in no rush, I just got out of one and needed some time off, so the search was slow. Sometimes I think a part of me knew I sought flexibility but I couldn’t quite tell at the time.

In my excitement for the move, I began exploring the new city online. And as the universe would have it, I saw an Upwork ad while reading an article about Canada on Quora. I had heard about freelancing before and wondered why it didn’t come instantly. It was the best solution. Nothing else offered that much flexibility. It gave me the much-needed time to explore the city and still earn. It felt great to have my cake and eat it. Although, I wasn’t so certain about how long I wanted to be a freelancer for, I was never happy with working 9-5, the conventional work spaces, and having to deal with badly behaved colleagues. So, in hopes that it’ll go well, I planned to stick with it without time restrictions. I have a degree in English and pride myself of being a pretty good writer so working with texts like before was the only option I had as a freelancer, and as I would expect, Upwork sure had a lot of jobs for me. My specialty on Upwork was proofreading and editing. I consider myself an English swiss army knife—I can do it all perfectly, from teaching to writing but beginning on Upwork I preferred proofreading and editing because it comes the easiest to me. I was in a resting place mentally and didn’t want to deal with the stresses of writing just yet. After reading every job application tip for Upwork, I realized it wasn’t going to be easy to get one—the market was tough. To stand out, I knew I needed an attractive profile and an impressive proposal. I noticed there were a good number of long-term opportunities, this pleased me because I looked forward to some stability regardless of the flexibility I sought. Although, this didn’t stop me from applying to one-time jobs—they mostly paid really well.

Freelancing pushed my creativity and helped discover sides of me I wasn’t quite aware of. While searching for suitable jobs one afternoon, I came across a writing gig. The client needed a fresh children’s story for an animated series. I pitched one in my proposal which would later become “Saturday James”. I received an offer within minutes, without an interview; he was really impressed and had a similar instant idea for the animation. The stipulated duration for the story was 3 weeks, but I completed it within 5 days. This was one of the few times I had ever surprised myself; it was such an impressive children’s story. Sadly, our working partnership was short-lived due to budget issues. But nonetheless, it was an amazing experience. I continued to apply for writing jobs, mostly related to children, and work truly became pleasure.

I enjoyed Upwork for the most part but my issues with the platform arose as a result of a series of austere or regressive upgrades to the platform. They failed to improve the quality of experience for freelancers and only focused on the clients’. Simple issues such as when a freelancer is given a poor Job Success Score (JSS) due to an accumulation of open contracts, which in truth are just successfully completed jobs that haven’t been closed by clients were not addressed. Freelancers began paying for connects to apply for jobs and were not refunded if the job expired or the client closed it. No incentives to stay on the platform or encourage freelancers in any way. Just a few of the problems that have pushed me to try offer my skills elsewhere but found nothing else so far.

Fortunately, I’m being covered by my partner’s employer health insurance policy. This is a huge plus for me because being a freelancer is a little risky, only a few get to enjoy financial stability with the help of long-term contracts. I’ve always been a supporter of Universal basic income and it would go a long way in helping everyone, not just freelancers.

With the influx of millennials into the labor market there’s bound to be positive adjustment to freelancing. The younger generation is populated with multi-skilled people and more flexibility is the only option for them to sell their skills easily. I hope it gets better, freelancing helps maintain a decent balance between work and personal time.
Author: Rachel Donovan