Published by Matt Keener:

Matt Keener2019 marks my 10-year anniversary as an Upwork freelancer (although I started out as an oDesk freelancer, which we’ll discuss later in this article). Over the past decade, I’ve billed thousands of hours through the Upwork platform and worked for more than 50 clients worldwide.

If you’re trying to figure out how to make Upwork work for your career, you’ve come to the right place!

~Matt Keener, Author of Executive in Sweatpants


By reading this freelancer guide, you’ll learn answers to common Upwork FAQs:

Let’s get started!

What is Upwork?

Upwork Job Search Filters
Figure 1. Upwork job search filters. Copyright owned by Upwork Global Inc. Retrieved June 14, 2019. Screenshot by Keener Marketing Solutions, LLC.

Upwork Global Inc. is the parent company of the world’s largest global freelancing website, According to Upwork, companies recruit millions of freelancers annually across more than 5,000 skills and 70 categories of work. Upwork provides an all-in-one platform for clients and freelancers to connect, interact, engage, and get work done.

Upwork is publicly traded (NASDAQ: UPWK).

Check out my  article, “What is Upwork?” for additional answers to this question.

Note: I’ll use the term “Upwork” interchangeably to refer to both the company and its freelancing platform, but, generally speaking, my primary focus for this article is on the platform and not the company itself.

How Does Upwork Work?

Upwork makes virtual business relationships possible.

What do I mean by “virtual” relationships? For purposes of illustration, let’s consider a “traditional” business relationship involving a freelancer and a client in a local town. Unless a prior relationship exists, the client must seek referrals from his or her personal network to identify a freelancer with the necessary skills. The client must then invest countless hours conducting in-person interviews, re-explaining his needs, reviewing resumes and proposals, working with attorneys to negotiate agreements, making offers, navigating the tedious onboarding process, and then finally hope that the freelancer works out. Invoicing and payments are usually handled on an as-needed basis, creating additional paperwork for the company. If the freelancer doesn’t work out, the client must start back at square one.

Compare this to a virtual business relationship that is facilitated by The client quickly posts a job, browses through thousands of qualified freelancers, sorts and filters by expertise and feedback rating, invites candidates with a few clicks, and begins receiving proposals within minutes. All interactions leading up to the hire (and throughout the duration of the relationship) can be completed within the confines of the Upwork messaging platform, eliminating the need for email or conferencing tools. Hiring a candidate is done with a few clicks, and the freelancer can begin working immediately after being hired. All time is tracked automatically using the Upwork desktop app and is logged into the freelancer’s work diary. Payment for hourly work is processed automatically, eliminating the need for paper invoices and checks. After the engagement has ended, both parties may leave public and private feedback for the other, creating a virtuous cycle for everyone.

Is Upwork the Same Thing as oDesk?

When I first began my freelance career a decade ago, I did so through (Grab Chapter 1 of my book for free to hear the entire story!) A few years later in 2013, oDesk announced a merger with Elance, another popular freelancing platform at the time. Shortly after that in 2015, the Elance-oDesk entity rebranded itself, becoming known as Upwork. When this corporate rebranding occurred, the oDesk freelancing platform was completely rebranded as Upwork, too.

So, for many freelancers like me, Upwork is viewed as the modern-day evolution of oDesk. If you were an oDesk freelancer prior to 2015, then your oDesk account was automatically converted to Upwork. (You probably still find yourself saying “oDesk” instead of “Upwork,” too. I know that I occasionally do!)

Would I Make a Good Upwork Freelancer?

Do you have a marketable skill of some type? Do you like to work hard and make other people happy?

If so, you might have a future as an Upwork freelancer. Having hired, managed, and worked with dozens of other online freelancers since 2009, I believe that a good Upwork freelancer usually possesses the following characteristics:

  • Highly talented
  • Focused on delivering client success & value
  • Extremely responsive
  • Stable & reliable (not constantly going from one crisis to another)
  • Good at “the business” side of freelancing (i.e., making a living)
  • Motivated to make freelancing a career
  • Willing to listen, learn, and adapt (not a know-it-all)
  • Fun to work with!

Does this sound like you? If you answered yes to most of these, perhaps it’s time to give freelancing a try!

How Do I Sign Up?

Signing up for Upwork is fairly straightforward. Click here to begin the sign-up process.

Does It Cost Anything to Be an Upwork Freelancer?

Creating your Upwork account is still free. However, starting in 2019, Upwork announced a change to its Connects program, which presents a new cost for freelancers. Allow me to explain:

A few years ago, Upwork starting allocating Connects, which are essentially virtual credits that freelancers need to apply for certain jobs. Most jobs require between one and six Connects to submit a job proposal. Upwork implemented this program to elevate its ecosystem and encourage freelancers to be selective about the jobs they apply for. I actually think it’s a pretty good idea, especially from the client’s standpoint.

As you can see below, my freelancer profile shows that I have 60 Connects.

Upwork Connects
Figure 2. Upwork membership and connects. Copyright owned by Upwork Global Inc. Retrieved June 14, 2019. Screenshot by Keener Marketing Solutions, LLC.

Originally, Connects were allocated to your account based on activity. Now, Upwork charges a small fee for Connects. Connects cost $.15 each and are sold in bundles. The minimum amount of Connects that you can purchase equals $1.50 in cost, which obviously isn’t a major expense.

Important Note: If you’re invited to a job by a prospective client, you do not need Connects to apply for the opportunity. So, in other words, there is no cost to you when someone invites you to interview.

However, since you’re just getting started on Upwork, there’s a small likelihood you would be invited by a client (remember, you don’t have a public work history on Upwork). Therefore, you’ll probably need to buy some Connects to apply for jobs. Buying Connects is relatively easy. In your Upwork profile, go to:

Settings > Memberships & Connects > Add More Connects

Does Upwork Take a Percentage of My Earnings?

Yes, Upwork takes a percentage of your earnings. Back in the good old days of oDesk, the percentage was a flat 10% of everything you earned. After the transition to Upwork, the service fee schedule changed as follows:

  • 20% of your first $500 earned with a new client
  • 10% of each dollar earned between $500.01 and $10,000
  • 5% of each dollar earned beyond $10,000

Clearly, Upwork uses this fee structure to encourage longer term, high-value contracts (which I appreciate). I’ve heard a lot of freelancers complain about the 20% fee on the first $500 earned, but, in my opinion it’s worth the cost.

Note: Contracts with “Enterprise” clients are exempt from the sliding Upwork fee schedule. Such contracts have a flat 10% service fee associated with them.

How Do I Get Clients on Upwork?

These days, most of my new Upwork opportunities originate from client-initiated invitations. Clients search for freelancers, my profile shows up, and they send me an invitation.

But keep in mind, I’ve been freelancing on Upwork (and oDesk) for the better part of a decade. I’ve billed over 5,000 hours through Upwork and maintain a job success score of 100%. All of this data is used by Upwork’s filters and algorithms when clients search for someone with my skills and background.

As a new Upwork freelancer, you need to proactively seek clients who are searching for your skills. So, what should you do to get clients on Upwork?

Here are a few steps for beginners that I recommend, as pointed out in my book:

  1. Build your Upwork profile. (Check out these tips for making your profile stand out!)
  2. Take some skill assessment tests.
  3. Filter for jobs that fit your abilities.
  4. Apply for five to ten jobs at a time.
  5. Send very personalized cover letters when applying for jobs.
  6. Impress your prospective clients (do your homework, arrive on time, speak loudly and clearly during interviews!)
  7. Follow up after the interview, but don’t be annoying!

For a more in-depth game plan for launching your Upwork career, grab a copy of my book on (It’s been downloaded by thousands of aspiring freelancers, is rated 4.3 stars out of 5.0, and is consistently on the Amazon freelancing and outsourcing best seller lists!)

What Does a Good Upwork Profile Look Like?

As a point of reference, here’s what my Upwork profile looks like:

Upwork Freelancer Profile
Figure 3. Upwork freelancer profile. Copyright owned by Upwork Global Inc. Retrieved June 14, 2019. Screenshot by Keener Marketing Solutions, LLC.

My Upwork profile is by no means perfect, but generally speaking I believe the following elements are necessary for a good Upwork profile:

  • Professional photo (try not to look weird, scared, or intimidating!)
  • Clear & concise headline
  • Well-written description – no ALL CAPS, no grammatical errors, etc
  • Carefully constructed work portfolio
  • Solid job success score (aka feedback rating)

Here are some additional tips for creating a good Upwork profile.

What About Submitting Proposals on Upwork?

Submitting proposals on Upwork is also easy. If you’ve been invited to a job by a prospective client, Upwork will send you an email with a link to the invitation (unless you’ve turned off such notifications, which I do not recommend). Click the link to review the job invitation and submit your proposal (you can also decline an invitation, which I have been known to do). New freelancers are less likely to receive such invitations, which means you will need to filter through Upwork job postings to identify those that match your skills.

With all of that being said, it’s important to be strategic in how you submit your proposal. Keep in mind that for any job posting, the client may receive dozens and dozens of other proposals from candidates. If you’re new to Upwork, you’re going to be at a distinct disadvantage when submitting proposals on Upwork, as you have less of a track record. To stand out in the crowd, try to follow these best practices:

»Submit proposals as quickly as possible

Many clients will post a job on Upwork, invite a handful of candidates, and then log out for a period of time. Some may even make a hiring decision prior to logging out. Your goal should be to submit a proposal while the client is still online and looking at the job posting. Time is often of the essence in the freelancing world. Responding within seconds or minutes of a post going live (or being invited) dramatically increases your chances of getting the client’s attention.

»Craft personalized cover letters (avoid templates)

It annoys me when I see freelance cover letters that are clearly copy-and-paste templates. The sad reality is that many freelancers fall into this trap, as it allows them to apply for more jobs and communicate a desired message (usually a bunch of links to past work or prior customer feedback). You should take a different approach. Review the client’s needs and briefly explain how you can help. Use personalized language to show you are already invested in the client’s success. Be conversational in your tone and try to engage the client in a discussion. Questions are good.

»Don’t be greedy

Yes, your time is worth more than $10 or $20 per hour. But remember, you’re just getting started on Upwork. You don’t have a work history or feedback score yet. You need to swallow your pride and underbid the market. Bidding $100 per hour isn’t going to make you successful (not yet, anyway). You need to go low, get some clients, and then gradually raise your rate as you add new clients.

How Will I Get Paid on Upwork?

There are two primary ways that you can get paid on Upwork: hourly or fixed-price. Most of what I do is hourly, but I have done fixed-price engagements before. Here’s a quick recap of each:


Upwork automatically tracks your time logged through the Upwork time tracker. Each Monday morning, your client will receive an email that summarizes how much time you (and any other freelancers on his or her team) billed in the prior week. Unless the client contests the time (which should probably never happen), Upwork will consider your time as approved by the client. Funds are released the following Wednesday. You can hook up your bank account to automatically transfer your earnings from your Upwork account.

→Fixed Price

Upwork has an escrow program that I’ve never fully understood or taken the time to understand. But, basically, you can set up milestones and get paid as those milestones are fulfilled. Or, what usually happens, you just tell the client that you’re done, and they pay you in one lump sum on Upwork. (Again, I prefer hourly because it avoids all of this back-and-forth or milestone stuff.)

How Does Upwork Feedback Work?

At the end of each contract, the client and the freelancer have the option to leave Upwork feedback. The window for leaving feedback is fourteen days from the end of the contract. Upwork feedback is based on a 5-star rating scale, similar to how feedback works on many eCommerce marketplaces. It’s important to note that Upwork feedback actually comes in two different types: public and private.

Public Upwork Feedback: Public Upwork feedback has been around the longest and is what gets displayed on your public Upwork profile. Clients can read through feedback from other clients to understand your performance and skills. Public feedback impacts your job success score. Here’s a screenshot of a few feedbacks that I’m particularly proud of:

Upwork Freelancer Feedback
Figure 4. Upwork freelancer feedback. Copyright owned by Upwork Global Inc. Retrieved June 14, 2019. Screenshot by Keener Marketing Solutions, LLC.

Likewise, the feedback that you provide is aggregated into a score for the client. Freelancers use this information to make informed decisions about who to work for. Here’s what my client feedback score looks like:

Upwork Client Feedback Score
Figure 5. Upwork client feedback rating. Copyright owned by Upwork Global Inc. Retrieved June 14, 2019. Screenshot by Keener Marketing Solutions, LLC.

Private Upwork Feedback: I can’t remember when private Upwork feedback became a thing, but I believe it was back in the oDesk days. Private feedback is not visible on your freelancer profile, but Upwork may use this information to influence your job success score.

What if Upwork Isn’t a Good Fit for Me?

After trying your best to win clients and contracts, you may decide that Upwork isn’t the right fit for you.

Before you go and close your Upwork account, I would encourage you to spend time studying the situation a little further. At any given moment, there are tens of thousands of jobs on I firmly believe that there’s a little bit of something out there for almost anyone. Perhaps you need to focus on refining your skills. Or, perhaps you should gain a few more certifications. Maybe reading my book would help you! 🙂

What Other Questions Do You Have?

I hope that this Upwork freelancer guide has been helpful as you start your freelancing career. Comment below with any other questions that you have! Best wishes for the future!

Read More About Freelancing


Matt Keener is the original "Executive in Sweatpants," having built a successful online consulting business (from home). His best-selling book offers tips for capitalizing on outsourcing and freelancing. Matt holds an MBA and has been featured by many recognizable brands, including Upwork (formerly oDesk), Elance, Insightly, the Dave Ramsey Show, and

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