The Ultimate Guide To Succeeding On Upwork
Photo credit: Upwork.com

When I started as a full-time freelancer, I signed up for three of the most prominent players: Upwork, Freelancer, and Fiverr. I created profiles, scouted out the competition, got used to the interface, and sought out as much work as possible. At this point, Upwork is pretty much the only platform that I use; I believe that the quality of clients and projects is the highest and most consistent. There are definitely some things I’d change if I could, but nothing is perfect.

More people are currently working as freelancers, and a significant number of different websites can help individuals connect with clients and find job opportunities. But which freelancing website is the best for you? It may depend on the type of industry you are in, whether you are looking for a long or short term gig, how much experience you have, etc.

Upwork is a popular option amongst many freelancers across a wide range of industries. There are over 17 million freelancers on the platform. The company touts itself as the go-to location for business owners to hire for every position of their company: from design to legal, to human resources, to sales.
So what’s it like actually to work on this platform?

Getting Started on Upwork

Signing up is straightforward. It does require some time and energy to complete your profile, but doing so is certainly worth the effort and will be vital if you want to stand out and start winning quality accounts.
You’ll want to make sure that you:

  • Craft a strong profile and resume: Your bio is a chance for you to quickly introduce yourself and say what sets you apart from your competitors. One way to give a sense of your personality or expertise is through a short video. There are also dedicated areas to talk about your professional and educational background; the more detail you can provide, the better.
  • Add examples to your portfolio: When you start, you won’t have any client reviews or recommendations to vouch for your experience. Make sure you give clients a sense of your style and skills by uploading a few short and sweet work samples or by including any relevant certifications (out of a pre-populated list) that you may have.
  • Set your rate and availability: Your profile will display the hourly rate you typically charge (however, many gigs are done with a set “project fee” that you and the client will decide upon). Take a look at what other freelancers are charging who have similar backgrounds. You can always increase your rate as you gain experience and even bid for a different rate than what you have listed. Also, let clients know what sort of time commitment you are looking for by setting your availability (choices include: more or less than 30 hours per week, or “open to offers”).
  • Take tests to demonstrate competency: At the time of writing, there are over three hundred “skill tests” on Upwork that you can take and display the results of on your profile (don’t worry, you can always “hide” any scores you don’t want to be shown). The tests are broken into a few dozen categories, such as mobile technologies, translation skills, etc. Choose ones that are most relevant to your skillset; this gives clients confidence in your work and shows your dedication.

Finding and Applying to Jobs

Using “Connects”

You apply for jobs using “connects.” Free accounts have 60 connects per month, and sending a proposal to a job typically “costs” at least two of them. So basically, unless you are “invited” to apply for a job (in which case no connections are required), you can send out about 30 proposals a month.

If you opt for a paid membership, you get 70 connects per month, which rolls over and cap out at 140. In my experience, 30 proposals are enough to get you plenty of work, so long as you are smart about the jobs you apply for and put in the time to complete well-crafted applications.

Searching for Jobs

Your homepage will auto-populate open jobs as listed, i.e., the postings get older as you scroll. These jobs will be based on the categories you indicated an expertise/interest in during the sign-up process.

There are several filters available to help you narrow down your search. These are the three big things that I typically look at to make sure that I am applying to a high-quality job that will give me the best chances for success:

  • Payment Verified: There are many incidences where individuals post a job that they will never fill. I believe that if a client is serious about getting the work done, they will verify their payment. In my mind, applying for jobs that don’t do this leads to a waste of time and connects.
  • Client History: Like the comment above, I always look to see if a client has past hires—it seems like some people really enjoy just posting jobs on Upwork! If they have past hires, read through any reviews to get a sense of what earlier freelancers have thought of the work experience.
  • Number of Proposals: Even if the job sounds perfect, I’m less likely to apply if there are already many applications. Remember, you want to stand out! Applying early for jobs that do not yet have many proposals can help you find golden opportunities. For instance, ten proposals or less than is okay.

Sending Proposals

Here’s where all of your earlier efforts come together and hopefully result in you getting awarded the work! When it comes to applying for jobs, attention to detail, and personalization is essential.
Here are a few things that I always do to help my application stand out amongst the crowd:

  • Personalize your message: Where possible, use the name of the client or their company in the message; this is a great way to catch a client’s attention.
  • Have an interesting “hook” or intro: After a dozen proposals or so, they all start to sound the same; make yourself stand out and be remembered with an exciting or funny anecdote.
  • Show that you’ve read the job description: The quickest way for your application to be discarded is not to answer questions or provide examples that are requested in the job post.
  • Point to relevant examples: If you are applying as a videographer for a tech company, point to any industry-specific standards, they may not be your favorite samples, but they’ll likely mean more to the client.
  • Ask smart questions: You don’t want to come across as annoying or arrogant, but saying or asking something that demonstrates proficiency in your field can mean much more than a line on a resume.
  • Keep the conversation going: Look to see if the client has indicated a date when he or she will make a decision; if not, I would wait three or four days to check-in and see if they have any additional questions or if there are samples/references that you can provide.

Working with Clients

Fixed Price vs. Hourly Projects

Before work can actually begin, the client and freelancer will need to agree on a payment rate and structure. There are two options, both of which can be set up to ensure that the freelancer is regularly paid for the work being done while giving clients the ability to approve work before payment is released.

Fixed Price Projects are best for work that is clearly and definitively defined; the freelancer knows what is expected of them, and when it needs to be delivered. “Milestones” can be set up, which either break up the different sections of the project initially or be added later as additional work arises that is relevant to the project. Freelancers request payment for milestones when completed.

On the other hand, Hourly Projects may be preferred for less clearly defined projects, including those in which the work scope may evolve over time or in situations where the amount of time necessary is less specific. Freelancers can track their time using Upwork’s desk app, which keeps track of different workstreams and takes screenshots every often. Work is billed weekly.

Ongoing Relationships

Upwork not only makes it easy to continue ongoing relationships on the platform, but these relationships are rewarded with lowered service fees after a freelancer earns a certain amount of money from a particular client. The platform also does this to deter clients/freelancers from taking their professional relationship “offline.” Upwork’s “percentage” is one thing that many freelancers complain about, so the good news is that it continually goes down over time.

Conflict Resolution

As with anything, there will be times when clients and freelancers disagree on the terms of work or product delivered. This is one of the big reasons it’s helpful to keep your communication on Upwork. If there is a dispute, a mediator can step in. Formal steps are in place—for both clients and freelancers—to file a claim against what an individual may perceive to be unfair.

I’ve been lucky that I have not had to approach Upwork to help me solve a conflict with a client, although I have heard horror stories in the past. If working on an hourly project, for example, you’ll want to make sure that you are always tracking your hours with the desktop app; if a client contests the work, you only have protection for the hours that have been inserted by the tracker. Freelancers can also file disputes on a fixed-price contract; this will enter both parties into mediation and a voluntarily paid arbitration if no mutual solution can be found.

Closing Jobs and Getting Paid

Submitting Work for Payment

As a freelancer, you will formally submit it and request payment when you have completed a particular project. At this point, the client has 14 days to either approve the work and release payment or ask for revisions. If they do nothing in this timeframe, payment will be automatically released to the freelancer.

Double-Blind Feedback

Once the work has been finished, both parties will have 14 days to leave feedback. Please note that if any money exchanges hands, the client will give you feedback, even if the project was not fully completed. Both the freelancer and the client will be asked to rate one another on several different factors, such as communication, availability, cooperation, etc.

The feedback is double-blinded, which means that you don’t see their feedback until you submit yours. I think that this is a great system that promotes honest feedback between parties. I mentioned this earlier, but I always look at the reviews a client has received (and given) before applying to an open job; for this same reason, I am always sure to provide detailed feedback that I think could help inform another freelancer later on.

Your Job Success Score (JSS)

This is something that I wish I had known more about at the beginning of my experience on Upwork. A JSS is assigned to each freelancer and updated about every two weeks. Unfortunately, Upwork is not incredibly transparent about how this score is calculated. For example, your score can be lowered if a job is left open for too long without work being done or if you apply for jobs outside of your indicated categories.

However, maintaining a high score and being a “top-rated” freelancer has several perks, such as having a badge displayed on your profile page or being able to respond to client feedback, so it’s really worth it to do all you can to keep this score high.
Recently, Upwork twerked the demands to have a high JSS score. Client’s who doesn’t give feedback will not affect your JSS score.

Set Up a Payment Schedule

Upwork is extremely flexible when it comes to payment schedules. You get to decide whether you’d like an automatic payment sent to your account quarterly, monthly, twice monthly, or weekly. This is great if you want to tuck your money away and not touch it for a while. You can also elect to “get paid now” at any time, use a wire transfer or a third-party payment provider. Entirely up to you!

Getting to Work on Upwork

Upwork is a fantastic resource for both clients and freelancers. I have personally been very impressed by the quality of the jobs and the platform’s talent. At this point, it is my primary source of income as a full-time freelancer. And while I’ve only been on the platform for about six months, I’ve already established several long-term professional relationships.

Mind you; it’s not all great opportunities; there are definitely some clients out there who are just looking to get as much work for as little cost as possible. These are not the jobs that you want. That said, you get out what you put in. If you’re going to work on great projects with companies that care about their talent, you will need to invest significant time and effort to ensure that your profile and applications are as solid as possible. By doing this, you can certainly have a fruitful career using this platform.

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