The internet has been a huge boon for the modernization of the freelance economy. No longer do we have to saddle up our horses, pack our talents and knickers into a haversack, and ride off into the sunset to…

You get the idea. 

But as romantic as galloping out to chase our dreams can sound, few of us have a financial nest egg to fall back on, and fewer still have the know-how to be successful. 

Personally, I am a writer by passion. I have always wanted to share my gift with the world and be rewarded in turn with the means to make a living; but until recently, I’ve had neither the guts nor the gumption to attempt it, largely due to the difficulties in getting hired in my chosen profession with no degree and no professional experience. So, like many other freelancers, I turned to Upwork to bridge the gap between desire and experience. 

Upwork is an online marketplace where clients advertise projects they need completed in a variety of technology-based fields, and freelancers who specialize in those fields bid on advertised jobs to win contracts. This allows freelancers to build a portfolio from scratch on a reputable website, and many end up shoring up lasting business relationships with employers they connect with as well. Upwork is a great place for new freelancers to forge a name for themselves, persons who hate the process of marketing blindly for new clients, and those who want to make a little extra cash outside their 9-5.

Some advantages of starting your career on Upwork include:

  • Access to a customer base with an annual expenditure of $900 million
  • Low-risk contracts; due to Upwork’s fee structure, they can afford to safeguard against bots, scams, and shysters 
  • Immediacy of hire: clients on Upwork are looking to hire now and start today
  • Location independence, with a few posted exceptions

There are a few notable downsides of contracting with Upwork; while I personally don’t find these to be deterrents, they should be taken into consideration when building a profile and structuring your pricing system. These include:

  • Upwork’s fees, which range from 5% to 20% per client (more on that later)
  • Competition: everyone within a given field is fighting for jobs of varying quality and pay with the greats, the mediocre, and the…not even not-so-greats, just a lot of spambots
  • The Ladder: even for those previously established in their field, no reviews on Upwork means clawing into their way back into the limelight for those choice contracts

All that being said…

Upwork can be an excellent way to jumpstart your career, or can even be your career, if you know what you’re doing (or are willing to learn) and have a legitimate talent to sell. But for those among us who have never done this before, taking this first leap of faith – and doing it well – can be an overwhelming task. So, rather than all of you doe-eyed dreamers leaping out blindly as I did, I have put together a framework, based on my own experience and the research I should have done before joining, to properly utilize Upwork and get that money rolling in. 

First off: pimp that profile. 

How you build your profile is important, as it acts as your resume and liaison for prospective clients. Honesty in your skillset and experience are important, as is your ability to sell yourself to your target market. The more effort you put into the initial stages of your application, the less you’ll have to correct later (no comment…).

As with any website, the basics come first. These include things like:

  • Uploading a headshot. Make sure it’s high-enough resolution you don’t become an amalgam of pixels 
  • Selecting your job tags – I write, so I selected tags such as Editing/Proofreading; Academic Writing; Creative Writing; etc
  • Preferred hours, locations, and rate
  • Your level of expertise from entry level to expert*
  • Education and certifications (remember, this is a resume. People want to know if you’ve gone to college)
  • Job history (even if it’s not related to your desired field. Again, resume, people want to know you’ve…y’know, done something)
  • A detailed description of yourself and your basic services and qualifications

*Please note that while it may be tempting to bump yourself up a notch and embellish upon your skills, you can have your account suspended or shut down for failure to deliver upon contracts. If you are willing to take the risk, your work had better be up to par.

Assuming everything here checks out, Upwork will approve your profile within 48 hours and possibly send you through a second round of identity verification. This just involves uploading a picture of a government-issued ID and hopping on a quick chat with an Upwork rep. Upon completion, Upwork will add a little checkmark to your profile – this makes you more desirable to clients, as it lets them know they’re really hiring you. 

That may seem like a lot to do, and it is – but we aren’t done yet. Dedicated freelancers can expect to invest 1-3 hours into fully fleshing out their profile. This can be done in several stages, so don’t fret about blitzing it out in one sitting, but do recognize that the faster (and more of) these upcoming sections are completed, the faster you improve your marketability. 

  • Upwork Readiness Test. This is a simple test of policies, procedures, and tips on how to successfully freelance. Completion allows freelancers to be featured and promoted by the site.  
  • Specialized Profiles. These allow clients to seek a more targeted skillset geared toward specific projects or genres. For example, I have two profiles: one dedicated to creative writing; and the other to article/content writing. Both of these feed into my general profile but interested clients can view them separately to get an in-depth look at what I offer. 
  • Upwork Portfolio. This is where you upload or link to individual projects. The more quality pieces you have on display, the more likely you are to get contracts; the more contracts you get, the more reviews you have to get more contracts. 
  • Popular Projects. This lets you create a specific project outline with price points for length and detail so that prospective clients can get an idea of what’s on offer. This is useful for deliverables such as short stories, websites, or Wikipedia pages.

Secondly: put yourself out there.

Putting in proposals on Upwork is pretty straightforward, but there should be thought put into each one. You’re not applying for a corporate position (usually); you’re applying for independent contracts and individual clients. Treat them as such. 

You find jobs by searching job tags or scrolling through a feed comprised of jobs algorithmically related to your profile. When you find an intriguing job, you can heart it to save it (if you like to batch apply, like I do), or you can apply now, if you’re ready. 

Every proposal costs Connects, the tokens by which the platform functions. A basic (free) account can purchase Connects for $0.15 apiece; a Tier 2 (paid) account gets 70 per month, with the option to purchase more. Proposals cost between 1-6 Connects per. 

Each proposal has several components to consider:

  • Cover letters function as a cover-letter-cum-get-to-know-you. They can be more personal or informal than a traditional cover letter, depending on the job. This is where you sell yourself and your services to this particular client, so be sure to target information and tasks listed in the job description, put in any required keywords (used by clients to weed out bots and mass proposals), and most importantly, be honest. In some cases, I have submitted proposals for contracts above my level; when I do that, I am careful to explain why I believe I am capable of completing the job and if/why I have proposed a lower contract price. For those who can spare the rejected Connects, this can be a way to land those higher-paying contracts without slogging through the crappy offers. 
  • Desired fee is broken into two sections: project and milestone payments. Projects are paid when all work has been delivered, as the name suggests. Milestone jobs are paid an agreed upon amount for a specified section of work on certain dates. I personally recommend submitting for milestones when the project requires a large amount of work for a lot of money, or if the client suggests a solid timeframe in their post. I would not recommend milestones for proposals like “4 blog articles monthly”; just bid per article and state that in the cover letter. You’ll save yourself a lot of time. 
  • Questions are optional for clients to include, and not every client will. Some are built to discourage bots; others to weed out mass-produced templates. Regardless, answer all questions openly and honestly; this is another place for you to distinguish yourself from the crowd of applications after all. 

After you’ve submitted a proposal that resonates with a client, they will message you with questions or further information. Some may request an interview or samples of your work; others may start you immediately. Either way, the key here is quick, positive communication. Freelancers who respond quickly are more likely to get higher reviews and repeat clients. Keep communication (and payment) inside Upwork for at least a year. This is both part of the terms and conditions, and a way to discourage scams. Remember: anything done on Upwork is protected by Upwork; anything taken off Upwork is not. 

Finally: kick that butt into gear. 

Almost everyone new to the site has to start small. Expect to bid low and get paid lower for your first few projects. The market rate for my chosen profession is $.01 per word. You read that right. A penny per word. Literally what Charles Dickens was paid for writing Great Expectations. I was ecstatic when early on I had a “high-paying” contract offer $.04 per word. I was less excited when I was offered $.004 per word – and took it, too. Successful freelancers know that reviews are the real currency here. 

When a freelancer is hired, a contract is opened. Clients deposit money for a project into an escrow account held by Upwork, and when the work is submitted to satisfaction, the client approves the payment. Upwork holds the cash for a few days in case of dispute, and then the money – minus their cut – is deposited to the freelancer.

Upwork’s cut is where many freelancers initially balk away from the site, but it is also where Upwork is able to provide guaranteed payment and a staffed office to address freelance and client concerns. The fee structure works like this:

  • 20% on $500 or less billed to a single client
  • 10% on $500.01 to $10,000 billed to a single client
  • 5% on anything over $10,000 billed to a single client

This may seem like a steep price, and if you’re not pulling in lot of contracts or never bill above $500 to a single client, it is. However, for those freelancers who can bill higher rates, put in the needed hours, or just have a high work output, the benefits offered by Upwork can easily be worth it. The alternative reality is often endless haggling with shifty, so-called clients on Craigslist for a $500 payment on a $3000 contract four months after they have profited from your work because you can’t agree on a font.  

At the end of every contract, after all work is submitted and payments released, both parties rate each other on a 5-star scale and leave feedback on the other’s profile (the opposing review isn’t visible until you’ve submitted your own, so get those in quick!). These reviews are visible to the general public, so it is important to be honest, but kind, and remember that good work begets good reviews, and good reviews beget good contracts. 

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