My Experience Freelancing Using Upwork

As those of you following my blog know, I jumped into freelance writing this past year. Early in 2019, I made a commitment to myself to spend more time on my writing. I wanted to take active steps to transition into getting paid for my writing.

I work a full-time (non-writing related) job, and I was looking for a way to get some paid writing experience under my belt. My dream is to one day freelance write full-time. I Googled some ways to pick up small freelancing projects on the side and stumbled across Upwork, a freelancing platform that connects freelancers with clients. I’d heard hit or miss things about it, but I figured I had nothing to lose with giving it a try.

A friend of mine I met in Peace Corps had mentioned using Upwork to pick up writing projects while living abroad in multiple countries, and she told me that she’d made enough money to live off and to fund her traveling adventures.

I’ve now been using Upwork myself for several months now and have actually had a fairly good experience, overall. In today’s post, I want to share some of the tips I’ve learned and guide other writers on their own journey into the world of getting paid to write.

General Structure of Upwork

The idea behind Upwork is that freelancers and people looking to hire freelancers (clients) can seek each other out, removing the need to cold e-mail potential clients. As a freelancer, you will create a profile and provide a description of the specific work that you do (i.e., content writer, general editor, fiction editor, blog writer, etc.). Once Upwork approves your profile and deems your skill set a benefit to the site, you can begin to browse the job postings.

There are a multitude of jobs listed on the site, and in terms of writing and editing work, you will find yourself in a sea of diversity. Each job post describes the project in detail (theoretically) and lists the client’s budget. Some examples of types of work I’ve seen are:

  • Blog post writers for topics ranging from cars and politics to makeup tutorials and yoga
  • Speech writers
  • Website editors
  • Novel/short story proofreader/editors
  • Memoir proofreaders/editors


When you see a job that interests you, you can choose to submit a proposal using “connects.” Upwork connects are basically virtual tokens that you have to pay for to apply for a project. New users get a certain amount of connects free, but then you have to pay a small amount for them once they run out. Currently, you can buy 20 for $3.00.

While I was initially wary of having to pay for connects, I think the connect system is actually helpful. Apparently, the purpose of requiring connects is to keep too many people from blindly applying to all the jobs and creating an overflow of competition. You’ll find that you have to apply to jobs immediately after they are posted to even have a chance at receiving an offer. There are lots of freelancers out there with the same idea of gaining experience and making money.

When you submit a proposal, you clarify how much you want to be paid for the project and when you’d like to get paid, whether it be per milestone (for example, per chapter or article) or at the end of the project. You will also be required to include a cover letter and optional sample work via attachments. You may have to answer a few client-specific questions, but most clients don’t seem to use this feature, thankfully, as I feel it is redundant.

Interviews and Offers

If clients are interested in considering your proposal, they will offer you an invitation to “interview.” Upwork’s version of interviewing means the client messages you through the Upwork messenger, giving you the opportunity to ask questions and giving them the opportunity to explain more about their needs for the project. Keep in mind that clients can interview multiple freelancers at once. Usually people make their decision on a freelancer that day.

All but once or twice, when I’ve made it to the interview stage, I’ve been offered the project in the end. Of course, an offer isn’t guaranteed after you’ve interviewed. You’ll be notified of an official offer both via e-mail and through the messenger. Be sure to review the offer in its entirety – confirm the payment amount, project details, and due date. By accepting the offer, you are agreeing to all the conditions listed.


Once you accept the offer, your contract will officially begin. You can contact the client with any questions through the messenger as you work on the project. Keep an eye on the agreed upon deadline, and make sure you submit your work according to the client’s time frame. When you’ve submitted the finished work, the client will either approve the work or ask for additional edits. I haven’t yet had someone ask me for revisions, but I’ve heard other people say it isn’t uncommon.

When the contract is ended, both parties have the option to leave feedback which is a great way to boost your reputation as a freelancer and to help other freelancers who are considering working with that same client.


When the client accepts your work, they will be asked to submit a payment, whether that is for a milestone or the whole project. This payment goes into your Upwork account, and you can specify that Upwork transfers these funds automatically to your personal bank account as often as once a week. If you don’t want to wait a week before having access to the payment, you can always withdraw the amount at anytime, but there is a small processing charge to do so.

Tips I Wish I Knew Before Freelancing on Upwork

  • Don’t bother applying to a job if 5 or more people have already applied. I rarely hear back from clients at that stage, so save your connects. You can see how many people have applied for the job already by looking at the bottom of the post for the “Activity on this job” details.
  • Keep in mind that Upwork charges a fee for its services. If the client pays you $50 for the article, Upwork will take a certain percentage of the amount in fees. Currently, the amount is 20% of the first $500 you make with a client, which is pretty steep. After the initial $500, it is reduced to 10%.
  • Know your worth, and don’t sell yourself short. The bad reviews of Upwork often (correctly) comment on the surplus of jobs offering ridiculously low pay for writing or editing (i.e., content mills). No one deserves to be paid such an absurd wage, even without experience. Determine your rates and stick to them. You may have to turn down jobs or pass on even applying, but it is worth it. Otherwise, you risk getting stuck in a cycle of low pay for equally minimal quality jobs.
  • Ask clients questions. A lot of my (unpaid) work time is trying to discern exactly what the client wants. Do they want their website edited with no major content changes? Do they want you to completely rewrite all the content to fit a new layout? Do they want you to use a formal or informal tone?
  • Try to finish your project a day or two ahead of the deadline. This promptness will reflect well on your work ethic and will also give you some buffer time if you run into any challenges. For example, I’ve had trouble opening client files at the last minute or had questions in the middle of editing or writing something hours before I need to submit it.
  • Be realistic of your expectations. I personally would not use Upwork as a sole source of income due to the competition for jobs, but I do think you can use it as a reliable source of supplemental income, and the more time you can dedicate to finding, applying for, and completing jobs, the more money you will make.

Upwork, like all job sites, has its pros and cons. In my experience, freelancers can make some quick cash through this platform, with project quality and pay depending on the individual client. Don’t be discouraged if you don’t hear back immediately from clients when you are first starting out. I heard nothing back from the first five or six clients I sent proposals to, but just when I was going to give up, I received an offer, and additional jobs started coming in quickly after that initial one.


If you have any more tips to share about finding writing and editing opportunities on Upwork, leave them in the comments section!

2 thoughts on “My Experience Freelancing Using Upwork”

  1. Upwork is a waist of time. I have been there since 2017 and didn’t get a single project and I have over 100 proposals sent. Employers don’t have a clue what are they looking for and expect from Freelancers to work for free. It’s a waist of time better get a real job then applying for work on upwork you won’t earn any money.


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