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How Freelancers Can Kill it on Upwork


Jan 18, 2018 | Stephen Jackson

The modern era of freelancing has been defined by the advent of the online marketplace. Never before has a global pool of potential work (and workers) been made more readily available, and this has been a boon for many people working as programmers, marketers, creative professionals, and just about everything else.

It’s widely understood that among the online freelance marketplaces, Upwork is one of the most legit and likely places for freelancers to find work. Of course, it takes some doing to really get a self-sustaining business up and running, but thousands of people use this site to make a living each day.

One of them is Loraine Yow, who started Lolo-ology, a custom art and illustration business, in 2013. Yow is a self-taught artist who specializes in portraits and avatars (cool cartoon profile pics), illustrations for articles, business cartoons, wedding invitations, and anything else that piques her interest.

Loraine Yow
Loraine Yow of Lolo-ology

“I saw some photorealistic pencil drawings on Instagram, and I thought to myself, I ‘wonder if I can reverse-engineer how that’s done,’” Yow says. “I tried it and found that I could, but also that my skills were wanting. Which made me want to keep practicing. And thus began my self-taught regimen and 10,000-hour journey. It’s not even the art that I’m interested in. It’s the quest for mastery itself.”

She started using Upwork just a year ago after she got her first Microsoft Surface Pro and began to produce digital artwork (she worked primarily in pencil beforehand).

“I chose to use Upwork because it seemed well-established, and they have a great escrow system that protects both parties,” Yow says. “The client pays upfront, but Upwork holds the payment in escrow and it’s only released when the work is complete. That way, both the client and the freelancer are protected from non-delivery and non-payment.”

She quickly earned a “Top Rated” status, and has recently been invited into Upwork’s Premium Service Program, where she’ll benefit from a talent agent and other priority services. You can find her profile here.

So, what’s Yow doing right? What can other Upworkers learn from her success? Let’s find out.

Go Above and Beyond

Yow says that when she first got started, she needed to make some concessions financially in order to score her first set of rave reviews, something she said was well worth lower pay at the outset.

“The reviews that clients leave will determine whether you get the next job, and when you are starting out you really need to secure some glowing reviews to get the ball rolling,” she says. “My first handful of jobs, I averaged about $8/hour. Even now that I’m more established, I still prioritize the quality of my deliverables over the monetary value of my time.”

In her experience, this early investment of time has paid off in the long run, since positive testimonials allowed her to up her price fairly quickly thereafter. Afterall, with so much competition in the world of illustration and graphic design, clients are extremely concerned with a freelancer’s professionalism, reliability, and ease of work. In this sense, glowing reviews are priceless items on an online profile.

Choose Clients Wisely

Yow warns newbies that contracts are difficult to back out of, and that doing so can harm your “job completion score” pretty severely. To this end, she notes a few red flags that everyone should learn to recognize from potential clients. These include:

  • Indecisiveness: A client not knowing what he or she wants at the outset of the job. If this is the case, the discovery process can eat up a lot of unbilled time. It also makes producing a clearly agreed upon deliverable difficult.

  • Rudeness: These jobs rarely work out well, since being a jerk over an email is usually a good indicator of the extent to which someone values creative work.

  • Passion Projects: Yow says that she only takes people’s deeply personal opuses on at an hourly rate, since it’s easy to get trapped in a forever-situation with someone who might never be completely happy with your work.

Keep Detailed Records

I keep a spreadsheet where I log specific details of every job — the time it took me, the rate of pay, my personal feedback on the client. This way, I can more accurately assess how long certain projects will take me — since it’s always longer than you think or plan for — and how much I should bid for similar jobs in the future,” Yow says.

She also likes to use this information to perform a “post mortem” after each job to understand what went well, what didn’t, and how she can improve in the future.

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