How to Grab Your First Upwork Gig

Andrew LoaderBlog, Freelance Writing

Grabbing Your first Upwork gig

I still remember how difficult it was to get that first Upwork gig. And I was one of the lucky ones. I scored my first Upwork gig within a fortnight of listing myself on the site.

I told the tale of my first Upwork gig a couple of posts ago in, What is the Online Freelance Marketplace? A Canadian web developer approached me saying he wanted somebody to write copy for an Australian client’s site. I wrote back, and he accepted my offer. I crafted the necessary copy, and he seemed happy with it. As far as I could see it, this was going to turn into a long and meaningful relationship.

Alas, lucky was not to be on my, or for that matter his, side. The Canadian web developer suffered a heart attack. It was not enough to kill him, but it gave him a good scare and taught him to reevaluate how he spent his life. As a result, he cut back on his work, and that meant that there was no more copywriting for me.

Despite that setback, it led to a long and happy relationship between Upwork and I. Although my work generated through there is minimal nowadays, it has been beneficial over the last few years.

A Few Last Steps Before You Are Ready to Start Applying for Jobs

This post is the third part of an Upwork trilogy. In the first part, I showed you How to Set up Your Upwork Account. In the second post in this series, I moved onto Setting up and Perfecting Your Upwork Profile.

By the end of this process, you are a bona fide Upwork customer, with a profile set up, and a professional cover photo. Hopefully, you have also taken on board my advice about expanding your profile and filling in any noticeable gaps.

Remember that depending on your niche, you could be competing with many other people for gigs. So you also need to build up a portfolio of your work. This collection can include work you have prepared outside of Upwork, which is particularly useful at the beginning of your job hunt.

One other way you can help yourself is by taking some of Upwork’s online tests. Upwork currently has 297 tests covering a full variety of categories. You are sure to find some that are particularly relevant to the types of gig for which you wish to apply.

At the very least, you should take the oDesk Readiness Test for Independent Contractors and Staffing Managers. They have probably renamed this the Upwork Readiness Test now, as the site has rebranded since I took the test.


Another test I would strongly advise you take is the English Spelling Test. Potential employers need to know that you are capable of using English. They will want to be confident in your communications abilities. If you are a writer like me, it is worthwhile taking both US and UK versions of this and several other tests. I would advise sitting at least one of these language tests even if you are hoping to work in an area like Design.

The tests are not that difficult to pass if you know your subject area. They do have some regional biases, but it is not too difficult to cope with that.

If you struggle first time around you are offered opportunities to resit tests.

You receive a score out of 5 for each test you sit. You can select which ones you want to display on your profile.

How Can You Get Your First Upwork Gig?

There are three ways to go about finding work on Upwork.

  1. You search for jobs
  2. Potential employers approach you for, suggesting you apply for their gigs.
  3. Occasionally a client will set up a gig specifically for you and send the link to you alone.

Until you build up a reputation, you are unlikely to have many employers contacting you, except for subpar minimal-pay type tasks. It will not be long after you establish a reputation before potential clients start reaching out to you, though.

Searching For Work

If you are using Upwork on your computer browser, you will see a Find Work menu option at the top of your screen. Some options stem from that menu item including another for Find Work. Click on that, and you will arrive at the Find Work screen.

You will see a list of potential jobs that people who are wanting freelancers have posted recently. Yout initial job feed may be smaller, as Upwork customises it to match your past searches and the categories of work you selected.

You will notice that I have a whole list of categories down the left-hand side. These were set up in the past when I carried out a particular search, and Upwork saved my search criteria.

Upwork lists your categories further down that first column.

If you are using Upwork on a mobile device or in their app, you will find all the same information; though it will probably be laid out differently.

Checking Out a Potential Upwork Gig

If you are interested in one of the gigs listed, click on its title. That will take you to a screen providing you with more information about the potential contract.

If you look closely at this example you will see the main components:

  1. The title of the gig
  2. The categories that the person advertised the position in
  3. A description of the type of work they expect.
  4. Time expectations – is this project a full-time or part-time gig? How long do they expect that it will take?
  5. The pay rate/experience level. People creating these gigs offer all jobs at Beginner / Intermediate or Expert Level. You would expect the pay you agree on to fit those descriptions. Be realistic in what you select here. If you are a beginner, there is no point in applying for positions advertised as Expert Level.
  6. Particular skills and expertise that the advertiser believes are important.
  7. Any preferred qualifications. These usually relate to your performance on Upwork, rather than traditional academic qualifications
  8. Activity on the Job – how much competition is there already for this job? Note that you only see limited results here on an Upwork Free account. If you pay for an Upwork Premium account, you can see more details about opposition bids.
  9. Information relating to the client. Have they offered jobs through Upwork before? Did freelancers give them positive reviews? Where are they based? What sort of payments have they made in the past? Be aware, though, that this may be a different type of job compared to their previous ones, so past payment details may not be relevant

If you like what you see then can then click on the Submit a Proposal button.

Submitting a Proposal for Your First Upwork Gig

Firstly, be aware that Upwork “charges” 2 Connects to submit a proposal. If you are on the Free Upwork scheme, they give you 60 free Connects a month. This means that you can apply for 30 positions for free. You gain more Connects if you pay to join the Upwork Premium scheme.

The Submit a Proposal page repeats some of the information about the job. It then asks you to propose essential terms for the position. In particular, Upwork requires you to bid a price for the job.

There are two types of job payment on Upwork:

  1. Hourly rate
  2. Fixed Amount

You selected your usual hourly rate when you set up your Upwork account. Therefore Upwork automatically assumes that you are offering to work on this contract for that price. You can change your rate to any level you like, though. Just remember that Upwork will take a 20% service fee out of whatever amount you set.

If the job you are applying for states “Fixed Rate”, you will be asked to suggest a total amount that you will charge them – again with a 20% Upwork fee. One guide that can help you set a price on Fixed Rate contracts is that clients state how much their budget is.

You are then asked to fill in a cover letter. The client may also request extra information with targeted specific questions.

Type a good cover letter, as you would for any job to which you applied. Don’t make it a form letter. Customise it for each position you chase.

Similarly, if there are any unique questions, provide a comprehensive answer. The client will use these to screen applicants and to gauge each applicant’s suitability.

If you have relevant sample of work that is not online, you can attach the file here.

Once you are happy press the Submit a Proposal button

Conclusion – Applying For Your First Upwork Gig

You have done it. You have applied for your first Upwork gig. Now it is a matter of waiting, to see if you have piqued the person’s interest enough for them to contact you.

But, don’t just sit back at this point. As I have said, the first Upwork gig is the hardest one. You need to keep applying for positions on a daily basis. So, use up all your 60 Connections if necessary. Furthermore, you could consider paying for more to top them up if you run out.

Eventually, you will hear from a potential client. And once you have that first client, things become much more comfortable.

I will discuss in more detail about how to write an excellent proposal in a future post.

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