Experience with Upwork: My Story (Freelancing 2020)

Using Upwork - Personal Experience
Using Upwork - Personal Experience

Yes, this is one more personal experience from an Upwork user. I work as an independent consultant under the flag of my legal entity, or as people would say, a Freelancer (I like the term hired gun more).

I work as a remote project/project manager but I believe that the recommendations in this article apply to different services that can be offered on Upwork and remotely. Freelancing is popular among the Programmers, and if you are interested in how to become one, then I’m sure you can find the article “Programming: Where to start?” very useful.

So, I’ve been using Upwork for some time. In the past period, I had a chance to e-meet many different people and to work for about 30+ clients.
My experience as a Freelancer using Upwork is positive.

I frequently investigate and I play with the offered tools so that I can increase the visibility of my profile. Also, I like to hear and read about the experience of other Freelancers. There are many articles, videos, and comments which are related to Upwork, its quality, and its development. I will share my experience related to using Upwork. Also, I will share my personal opinion on some of the popular subjects commented by other Upwork users. I hope that my experience will be useful to some of the Upwork users.

General experience

  • Upwork is a service that helps professionals to find customers easily and vice versa;

Bidding to job offers

  • Don’t be afraid to bid and accept a fixed price job even if you are not fully satisfied with the financial compensation, especially if you are a newbie on the platform. Take that job, deliver great service with a smile to your customer, and even go the extra mile with the delivery. After that, make a story of that job (update your portfolio, ask for a reference from the customer, update your website, make a reference to the successfully completed job, in your next bid), so that you can have a much better starting position for the next bid. (everything counts in large amounts)
  • Try to be fast and apply to newly published job offers. I use one simple tool called Upwork jobs feed tracker that helps me to be notified upon new job offers. (be quick or be dead)
  • Give a priority to the job offers that best fit your competencies, skills, knowledge, and experience. Use various filtering and searching tools provided by Upwork to cross-check if some good fit is out there. I’m sure that you can agree, It’s common sense. Choose to compete in your native environment. In this way, you can offer the best from you to your customers. That would help you to reach your financial projections.
  • Always look at the ratio of the total number of submitted offers vs when the job offer is announced. For instance, if the job offer has 20+ proposals, and if the job offer is announced before 3-4 days, think twice (identify if you are a really outstanding fit for the call) before you spend time to apply for it.
  • Give your best shot when you are writing a proposal. That’s your ticket to land a contract. Even though you know you’re good on the field, the person on the other side doesn’t know you at all. I usually read the job offer description carefully and I’m trying to identify the root cause of the call. In this way, I can easier hit the target in the center with my proposal which not necessary should be the size of the Anna Karenina novel. Life is getting faster and faster. Usually, the reviewer of the proposals doesn’t have too much time to read novels instead of concise proposals, if you know what I mean. Also, besides identifying the business objectives in the description of the call, I’m trying to read in between lines and to identify the style in which I have to write my proposal. Do they like brief info or do they like a bit more details? Should I be 100% formal, or should I express my creativity and art aspect of myself? The bottom line is, I take the creation of a proposal seriously in which I invest. Of course, if you are running out of money/savings, and you don’t have active contracts, then you start acting irrationally and make stupid things that reflect the proposals as well. That’s why you have to take care of your savings. Actually saving is the first lesson in entrepreneurship and running a business. But that’s another topic.


  • I believe achieving equilibrium is more art than science. Rates depend on many factors especially if you play in the international playground. In that context, I’m sure that you are aware that the quality of service is the basis. But there are other aspects as well. In this case, I like to mention the psychological aspect. For instance, If you are in rush into a new contract because you are out of resources (read money), then you are trying to make everything to get a contract by offering low rates, which is legit of course, but I’m sure that you don’t like that scenario. That’s why I try to remind myself of this scenario when I’m in a good position and to make bids when I have an active contract and deposit, especially when I have good contracts. In those cases, you usually are with less pressure and your self-confidence which can result in comfort to you to search only to the best job offers for you, to which you can prepare a financial proposal you really like and expect to get those contracts.
  • Work on improving your own quality so you can offer better quality and not to bid with the lowest prices. In this way, you will find the path to much better customers.


  • Upwork can secure the payment in a case you deliver to a customer. It can help in some scenarios. In one case Upwork paid me on time (weekly), even though my Customer had a problem with the account. I had colleagues in the same project that had a contract directly with the Customer (not using Upwork at all), they were left with empty pockets. In this context, my experience with Upwork is also positive.

Common Questions, Comments, and Statements

The following list includes my replies to some common questions, comments, and statements about Upwork.

Upwork is Expensive

Some people: Upwork is the most expensive among the other similar services and it charges even for bidding to job offers.

Me: That’s why Upwork is one of the best. Are they ideal? No, but they are trying to increase the quality of the service. Calculate the Upwork’s fees as a cost for your service and include it in your financial proposal.
I believe that introducing and increasing the number of so-called connects required for bidding, helps in filtering all those not qualified and not serious applicants.
Also, I would add that Upwork introduces new services by which they try to recognize serious Freelancers and to support them. I had a good experience with their premium services. An Upwork agent was working with me to help me achieve my personal goals.

Upwork is Very Hard for New Freelancers

Some people: Upwork is extremely competitive and it’s very hard for the new Freelancers.

Me: Life is hard. Every begging is hard and I think that’s not something exclusive for the new Freelancers on Upwork. My experience with Upwork is a bit different. Upwork is trying to engage newly registered/recruited Freelancers on the platform by putting their profiles up in the search results. I have been playing with the Upwork search feature a lot., and I was pretty much surprised how much new and not the best matching profiles to my search were on the first result page.

I guess nobody knows how the Upwork search works, except the guys who work on it, but it’s more than obvious that they are supporting new Freelancers by promoting their profiles higher in the search results. I’m not trying to tell that a bit more experienced Freelancers on Upwork are handicapped because of that. Upwork has some other services for them that work only upon invites, that the experienced Upwork Freelancers can receive.

About Vasil Buraliev 19 Articles
Consultant for project management and software development with a background in bespoke software development and 22+ years of professional experience in designing software systems and managing IT projects mainly for the public sector. Seeking to use analytic and management skills as a consultant in large-scale IT projects.

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