Experiences with Upwork: An Historical Overview
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Experiences with Upwork: An Historical Overview

John works at the airport on our way to somewhere…

My husband John and I started using the Upwork platform back in the days when Upwork was still two companies: oDesk and eLance. Before that, we’d been the owners of several businesses, some successful, some not successful. Between 1998 and 2002, John and I started an online business that worked primarily with getting newspapers onto the web. Then, between 2002 and 2010, we owned a web development business that sold web sites to local businesses in western Nebraska. Selling directly to our clients was a hard gig and we never made more than $3000 (gross) in any given month. Most months we made less than $3000. Our bills were higher than $3000/month, so you do the math. It was a bleak and difficult decade for us.

We lived sale-to-sale and often we couldn’t pay our bills. Sometime around 2008, when we were the owners of the web development business selling to local businesses, John started sourcing and hiring freelancers to work underneath him through oDesk. John was a well-rounded business-person and web developer by this time. He sold web sites and did customer service with difficult western Nebraskans who knew little about the web (think farmers and ranchers). He designed the web sites and he coded them too. The idea to hire coders to take on some of the work load came because we realized that it was easier to find this type of worker, coders, than find salespeople or customer service reps we could trust.

So John worked with a number of contractors through oDesk between 2008 and 2010. Some of them were great. Others sucked. We both learned a lot about managing people. We learned about things that freelancers do to wiggle out of work while still trying to get paid. We learned how to identify good freelancers and bad ones. But then, in 2010, John had a conversation with one of his freelance contractors that changed the way we did things forever. The contractor’s name was Matt and he’d been working for John for $20/hour. He was a reliable programmer, but one day, Matt told John that he’d been offered a job at $40/hour by Lucas Films. He couldn’t work for us anymore. At this point, John took a step back from what he was doing and asked himself why he was spreading himself so thin. John was a talented coder. Couldn’t he be working for $40 for Lucas Films? He sat down that afternoon and added up how many hours he was working and how much he was getting paid. When he put pen to paper, he realized it was only making about $6.00/hour. It was then that he signed up at oDesk and eLance as a freelancer. He massaged his profile page to make it “pop” and set out to put up 20 cover letters as fast as he could. The idea of not having to go out on sales calls was like heaven to John. He steadfastly committed to working through oDesk as a coder with the big dream of making $20/hour on a regular basis (the mere idea of it was like heaven).

I wasn’t as quick to get on the bandwagon with John. I’d been doing lead generation for our business, making calls and talking at length with people to learn about their business and feel out their potential desire for a web presence. I also wrote the content for the web sites we sold. I wasn’t a big believer in the possibility of “freelancing” and though I’d been writing for local businesses and a few newsletters over many years, I didn’t feel confident putting myself “out there” as a writer. I felt like a faker and a charlatan. Writers, after all, published books and did signings at local book stores. So instead, I signed up to go back to school to get a nursing degree and, at the same time, I worked toward doing a practicum to get licensed as a marriage and family therapist (I have a master’s degree in psychology). I hedged my bets on the things I’d been schooled in and figured that one of these two paths would begin to open up.

Indeed, I got into nursing school almost immediately for the fall session that would start a few months later. I made some phone calls and set up meetings to talk to some therapists about sponsoring my practicum.  But I had some time on my hands before either one of those prospects would take shape. So I decided to spend 30 days meditating. Each day, I required myself to do nothing but sit in a room, facing east, for one hour (which is harder than it seems). My meditation goal was to think about Nothing.

Mostly, at first, I sat for my hour each day chastising myself for sitting and “not doing anything”. I tried to focus on an imaginary yellow ball (a technique recommended in a book I’d read) and as I did, imaginary conversations with people (some friends, some strangers) took place, the words weird and non-sensical. These dialogues bloomed like exotic flowers out of a big black pool of nothingness in my brain. Then I would notice pain and discomfort in my body caused by the stillness and inertia of sitting. Sometimes I was with my body, at other times, my consciousness wandered off and I was Elsewhere. I observed the din and litter of thoughts and feelings that had been unattended to for years. But then, slowly, my mind started to clear.

And one day, I opened my eyes and I was ready. I was ready to put myself out there and do the whole “oDesk Thing”. I’d call myself a writer. Yes, I could do that. I told John that I’d try it and if the work didn’t take shape and and start rolling in before the semester started or I found a practicum sponsor, I’d go to nursing school or become a therapist.

It took only about two weeks before that first client contacted me after I got my profile completely built and the 20 initial cover letters sent out. Luckily, John had been working with the oDesk platform already so he recognized right away that there was a problem with my first client contact. The client asked for me to work outside of oDesk, which was against their terms of service. It was a woman (supposedly) and she contacted me via Skype to tell me about their company’s products and what they wanted me to do for them. The job was to write sex toy descriptions.

I declined the offer.

Next, I started going after clients that were offering to pay very little for big jobs that needed to be completed ASAP. This worked for me to get that initial client. I found a client that needed TEN 500 word articles written within 24 hours using a list of keywords, all of them pertaining to chicken coops. I knew very little about chicken coops, so I had to do research in addition to writing the articles, which took a grand total of about 7 hours (I worked into the wee hours of the night). I got paid $10 for the entire project. But I got a 5 star rating on it, so I was happy.

Next, I got hired by a company to write about construction and interior design. This was a topic I knew a lot about from renovating our old school building. I wrote about how to install a wood stove. Then I wrote about how to frame out a wall. They loved me, in part because I knew my stuff, and I completed my projects on time, but also because I was working for about $5/hour. Again, I got five-star ratings from this client, so I was pleased.

I raised my rate to $10/hour.

Over the next 3 months, John and I struggled to keep up with all the work we were getting. Late at night, after we’d closed our computers, we’d talk about how to “moderate” the workload. We had too much work. Lydian was only 10 years old at that time and homeschooled. She still needed my attention. I couldn’t accept every client that offered me work. I’d already raised my rate to $18/hour.

It was then that John and I realized that supply and demand governed our work as freelancers. When there was a lot of work, we needed to raise our rate to get fewer job offers because it was stressful to get offers and have to turn them down. When work was flowing in, we needed to raise our rate high enough to where we’d consider doing the work even if it meant working “overtime”. But what’s over-time when you’re a freelancer? Twenty hours? Forty hours? Sixty hours? It depends. We philosophized about this problem because it wasn’t as easy to solve in practice as it is to think about, especially after having been poor for so many years. It was hard to turn down thousands of dollars worth of work after having lived week-to-week and month-to-month.

In turn, when work was scarce, we had to lower our rate to get more of it. Of course, the market still informed how low or how high we were able to go based on our skill-sets, experience, and ratings. There are periods of famine in our freelancing lives where we have hardly any work and it always feels like perhaps the work has disappeared forever. Often, we take on crappy clients during these times of famine out of desperations and usually, when the famine ends we regret it. It would be better to enjoy the famine than to flail around desperately trying to end it. The flailing, I think, is a symptom of living in a country like the United States where things are too expensive and it’s hard to live cheaply. It’s easier to forego the desperation in places where the cost of food is reasonable and where we can imagine surviving for long periods of time on very little. This is one of the keys to making freelancing successful, in my opinion.

The psychology of having to deal with ups and downs in terms of work was hard to navigate. The cycle of abundance and scarcity is never predictable, though sometimes John and I try to apply logic to it. Generally, for example, there’s less work available when parents are sending their kids back to school and at Christmas when people get busy and overwrought with holiday “festivities”. Since most of our work comes from the U.S. or Europe, we’re subject to these somewhat predictable fluctuations. But we don’t always get less work in August/September and December. Some years, things slow down less than others during these seasons. As freelancers, it’s essential that we have a savings account to get us through the leaner times. And it’s important that we exercise self-restraint even when things are going well for us financially. Freelancing offers no guarantees in terms of money or security. What it does offer though, is the opportunity to keep learning new things that make it easier to stay adaptive to the changing environment. As freelancers, we’re mobile so we can move to greener pastures as needed. And John and I have other experiences, education, and training besides just freelancing-related skills. As Lydian gears up to make her freelancing debut as a graphic designer, she’s also getting her TEFL. And she has an associate’s degree. She’s not planning to head out into the world without a back-up plan. Online work is cool. I like our lifestyle as people who work online, but I acknowledge that it could go away at any moment. Should that happen, there are other types of work John, Lydian, and I could do anywhere in the world.

When Lydian was 12, I raised my Upwork rate to $50/hour to stop the flow of prospects. Lydi needed my attention and John was making enough at that time to support our family. Still, I’d get job offers though and from time-to-time, I’d take them depending on Lydian and her needs. I worked on building a different business centered around theater at that time rather than spending a lot of time behind my computer which allowed me to keep working while continuing to educate Lydian. I incorporated Lydian into the business and she learned about business, management, human relations, marketing, theater, art, and a variety of other things. The business only opened for 5 to 8 days each year, so the rest of the year it was a petri dish of educational opportunities.

Back in those days before Upwork consolidated oDesk and eLance, freelancing was a lot more laid-back in terms of acquisition. After paying our dues by getting high ratings and communicating clearly with clients, we’d get invitations to interview on a regular basis. Once we’d sent out our quota of cover letters, we’d wait. Usually, none of the potential clients we’d sent cover letters to would respond (or maybe only one or two of those clients would contact us, which always seemed strange, but it’s still that way). But the oDesk algorithm would put us closer to the top of a list of freelancers and so once the cover letters were sent, more and more potential clients would contact us to invite us to interview for different jobs. On the average, about every 10th client that we worked with would turn into a long-term relationship of some kind. John and I realized that a big part of our client base was made up of disgruntled business owners who’d already tried other, cheaper freelancers with poor results. But both of us were very reliable. We did what we said we were going to do, based on our client’s specifications, when we said we were going to do it. And we were fast. We didn’t diddle around when we were on the clock. There was no need because most of the time, there was plenty of work waiting for us from other clients. For us, it was all about doing the work the way the client asked us to do it, according to the budget, and by the deadline specified.

When oDesk and eLance changed to Upwork, we had a sense that the freelancing environment was changing dramatically but we weren’t sure what would happen exactly. Around this time, John had some run-ins with shitty clients. I mean, both of us had had our fair share of clients-gone-bad, but I’ll say more about this in another article. One of the shitty clients was actually a pre-Upwork client, a lawyer who’d tried to start a business that had failed. Working within the statute of limitations, he decided to sue John to get his money back (like a refund, ya know?) since the business had failed, even though it was definitely not John’s fault. The other client wasn’t a lawyer, but he knew how to work a diseased and ailing social system (Upwork Mediation Services) in his favor. He contacted the Upwork customer support and mediation services team and though John had hours and hours logged ON THE UPWORK PLATFORM with screenshots of the work he’d done for this client still, Upwork decided in favor of the client and John had to refund all the money from the whole project (which amounted to thousands of dollars).

We both seriously considered not working with Upwork again after this transaction. John took the “ruling” pretty hard and it made him feel pretty vulnerable as a freelancer. He started putting feelers out for work through other mediums like Linked in and Outsource (now RemoteWork.com). By this time, he was established as a top-rated programmer and business-man. John isn’t just a script-kitty, after all. He’s owned a number of businesses, he’s a top-rated salesman (he’s received awards for his sales abilities), and he has excellent management skills too. He’s worked as the CTO for several big companies. Often, he functions as both a web developer and a business consultant for clients, which is why he can ask for a higher rate. But Upwork, through their mediation “process” made John out to be some kind of shady, tiny-hill-of-beans-kind-of person, ruling in favor of the client, a man who’d tried to start a business using other people’s money (angel investors) and failing miserably at it.

Several years later, Upwork asked if John would be willing to be interviewed by Forbes magazine as a representative of Upwork freelancers when Upwork changed their pricing structure. He agreed to be interviewed of course, but even despite the interview; even after years of working on this platform and making thousands of thousands of dollars for this company, they still treat him as a minor and unnecessary cog-in-the-wheel. And in the online world, the reality of it is, that’s all he is. That’s all I am. We’re cogs-in-the-wheel who are feeding The Machine.

Since that time, we’ve learned that as a general rule Upwork rules in favor of the client. The general thrust of things appears to be that it is through the client that the money comes so the client is more important than the freelancer. But without freelancers, there will be no clients. Of course, without clients, there will be no freelancers too. It’s a difficult balance for a company like Upwork and I acknowledge this fact. The human side of a business this big is impossible to manage without scripts and algorithms. And finding good mediators is nearly impossible in a society that values money more than human relationships. I don’t know how I would solve this problem. It’s a challenging one for sure and though Upwork has done things wrong, things that have hurt our family financially, John and I still get work through this platform. I don’t want for Upwork to disappear because we use it and it does work for us most of the time. But newbie freelancers need to be aware of the Upwork environment and understand the dynamic of using this platform before they put themselves out there as prey.

And maybe “prey” isn’t always the right word. Admittedly, it’s not exactly the right word because not all clients are predators. Indeed, some freelancers are like predators too. But freelancers have to realize that between 10-25% of the time, clients are going to be shitty. It depends on the type of work freelancers are doing, the time of the year, cosmic shifts in the universe, and other unpredictable factors perhaps related to one’s Karmic Path of Enlightenment. When the shitty client crosses your path and Upwork rules in favor of them, it’s important not to be crestfallen and give up of yourself or Upwork. If you work as a freelancer doing work that deals with Online Things (like web writing, web development, graphic design, etc.), then you’re feeding The Machine. Don’t try to identify with the work in a human way. It’s all numbers at the bottom of it all. You’re a number. Your rating: a number. Being a web developer shouldn’t define your whole existence. It’s work and that’s all. Do it so that you can live your life freely as a Real Human and meanwhile work to build other, more meaningful aspects of your existence. If you find clients who are Real Humans too, treat them with respect and dignity for as long as the relationship lasts.

Further, there are a number of “algorithms” in play on Upwork to diminish the workload of actual human workers that take their seats behind the platform. These algorithms chew freelancers up and spit them out all the time. John and I have both been chewed up and spit out. I think we’ve even been swallowed a few times by the algorithm. Freelancers who work in a non-coding field may not be able to discern the difference between what’s algorithm and what’s real. If you’re having an experience on Upwork that feels machine-like and cold, like an evil step-mother trying to crush your dreams, it’s probably the algorithm at work, though sometimes the algorithms work in your favor too. If you’re going to Feed the Machine, as most freelancers do these days, you have to be aware of the algorithms and deal with them but not become subject to them (because you’re still a human). You can learn to Feed the Machine with one hand and go feed starving children in Nepal with the other, but don’t think of Upwork the way that people thought about their jobs in the 1950’s because things aren’t like that anymore. They’re not better or worse. They’re just different. And one of the advantages of being a freelancer is that you can step back from it, change, adapt, take a break as needed, and look back at it from the outside. But I’ll say more about that later…

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