Freelancing Success on Upwork

Freelancing Success On UpworkFreelancing is a great way to earn money while being in charge of your time and working from home to boot! I have dabbled in it a bit, and my hubby, Ken, has worked for years as a freelancer. Over the years we have found work on various freelance sites such as Guru, ODesk, Freelancer, and others. The current favorite and leading site is Upwork ( In our opinion Upwork leaves the others in the dust.

Upwork is a huge freelancing site. Think of it as a marketplace where potential clients meet potential workers. It’s a little more complex than that, but in a nutshell, it’s a place where talent meets those in need of talent.

There are thousands of freelancers on Upwork, so you might think the competition is fierce. Not necessarily so! Those who succeed on Upwork have a few approaches to help stand out from the crowd. Granted, getting started will be slow at first, but it will snowball once you give it some time and some attention. You need to build up a history of completing jobs so you can land further jobs. How can you get started then? You can bid on jobs and sooner or later a client will engage your services. However if you quickly wish to get some work history behind you, ask a friend or relative to hire you. You can devise a project and have them post it and then hire you for it. Complete the job, and have them leave you a glowing review. Is this cheating? Well, view it as you will. It is a way to get a little work history. If this feels unethical then don’t do this.

Your friend/relative will need to open an account on Upwork as an employer. Note – I use the terms employer and client interchangeably. You will need to open an account as a freelancer.

Once your account is open, it’s wise to note some things that help you land jobs. The process is you will browse or search for open jobs that are in your field of expertise. Then you are competing with others, and also attempting to convince the potential client to hire you for the job. Given that, here are 5 things you should know about to succeed on Upwork:

1. Have a complete profile

The more there is for potential clients to see, the more likely they will feel comfortable to engage with you. Upwork tells you how much of your profile is complete. The elements of a profile include:

  • A photograph of yourself
  • A functional and perhaps catchy tag line about yourself
  • An overview (a freeform area to say how great you are). Put reviews here from other clients and anything that helps to “sell” yourself
  • A selection of skills aligned with your expertise (select up to 10)
  • A portfolio (a selection of projects or samples you upload)
  • A filled out education section
  • An hourly rate

A note about the hourly rate – some jobs are by the hour (therefore the hourly rate), and some jobs are fixed price. Each has its own merits.

There are other items you can provide as well, such as employment history, certifications, and “other experience”. You can even put up a video. I have not seen many people do this, but certainly something to consider. It could be a video of you talking, or a video showing a project you worked on.

Here is Ken’s profile. His profile is a good one, as he regularly lands jobs on Upwork.

Ken's Upwork Profile


2. A great photograph

Although this is part of the profile as explained above, it is a critical piece as it is the first noticeable thing a potential client sees. Provide a photo that is some mix of professionalism but also that you are an easy person to work with. Yes I know that’s asking a lot! How can you get that message across in a photo? Hmm… smiling helps. Looking confident helps. You get the picture (yes, pun intended).

3. Personalize your proposals

When you respond to job listings, write a unique proposal for each. That is, speak to what the client is asking! Read carefully what the client is asking for. Read the entire job listing as some clients use a technique to weed out applicants. What they will do is, towards the bottom of their job listing, they ask you to start your proposal with some phrase. This proves to them that you read their entire listing. Be diligent about this.

Sometimes there is very little information to go on. It has been our experience that applying for jobs that are not clear is not a good move. We avoid those. If the client is not clear, this likely will lead to a bad experience.

Often we see other freelancers leave canned proposals. These are easy to spot because they are generic sounding and don’t address any particular point the client stresses in their job post. A good proposal will address the exact items the client mentions. A great proposal goes one step further and explains (or even links to) jobs you have done that are similar. Someone starting out does not have this luxury, but will, given time.

4. Be a specialist, not a generalist

This is one mistake many make. They try to be a jack of all trades, responding to job postings that require all sorts of skills or abilities. It’s understandable when starting out to try and land as many jobs as you can, but in the end, if you are all over the map of what you have done, future clients have a hard time pinpointing your real skills.

Back to my hubby, Ken’s list of skills are all based on non-fiction writing and editing. There is not a whim of fiction mentioned, nor is there any skill listed that is not about writing and editing. That is it for him. He specializes in non-fiction, period. He does get invites to jobs focused on different skills, and he declines many of them. The point is to build up a foundation of being great in one area. This leads to great reviews as well – which help land more jobs! That’s a win-win.

Upwork Selected Skills

5. Close stagnant jobs

We have often experienced starting work with a client, and they drift away. A recent example, Ken took on a job to write 4 articles. Even though the client funded the entire project (put the full amount in escrow), he become unresponsive after Ken delivered two articles. You might initially think the client is not happy with the work and didn’t want to pursue working together any further. However in this case, and this is common, the client had already paid for the work ahead of time. Which make us try to second guess what the client is thinking. If they truly were not satisfied they would ask for the remainder of the escrow back, but they don’t do that either. The project just stalls out.

We checked with Upwork what to do when this happens and they suggested that we end the contract, and return the remaining escrow. We were told that jobs that show significant lack of activity will ding your job success score. You want to keep that score as high as possible, so – end those lingering, going nowhere jobs.

Bonus advice

One more for ya! Before applying for a job, research the employer. You won’t likely know who the client is (Upwork will not show you that info), however you can see what other jobs they have run through Upwork, as well as seeing the types of reviews they have left for other freelancers, and the rating that other freelancers have left for the client.

This is valuable information. The advice is to steer away from any clients who leave bad reviews or feedback. We have worked both sides of the Upwork fence (we have been clients hiring freelancers) – and it is our position that unless a freelancer outright did something horrible (like plagiarizing work), then we always give a 5 star rating. Just our style, not saying if it is right or wrong. However we see this same approach with other clients. Many leave a 5 star. If you see where a client has left a number of less than 5 star reviews (sure some freelancers do not deserve the 5 stars), then the odds are good that you will not get a 5 star review either. Some clients are just not “nice” about it. So don’t apply for jobs from clients like that. Even though it might feel like you may have lost out on earning some income, you will likely lose more work if your reviews are not stellar.

Upwork Sample Reviews


Upwork is an active site where thousands of people make a good income working from home. It does take some work to understand how to best succeed on there. Be patient but be consistent. Over time, if you give it your 110% effort, you will have a good income stream from freelancing on Upwork. Good luck!

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