Upwork—Is it Worth it? A Beginning Freelancer's Perspective

If you enjoy my blog, you're probably a creative person of some kind, whether you're a writer, a visual artist, a graphic designer, or something else. Since I've recently ventured into the land of freelance work, I thought I would share my experience with a particular website, Upwork, to help you decide whether it's worth it.

My perspective is purely short-term because I've only gotten serious about using Upwork for the last few weeks, but I might write an update later on. Still, I think the first few weeks are worth talking about, because they can be the scariest.

What Is Upwork? 

Essentially, Upwork is a website that acts as an intermediary between freelancers and clients. It helps them find each other by allowing clients to post job offerings and freelancers to submit proposals. When submitting a proposal, you write a cover letter and may be required to answer additional questions. You can also include samples of previous work. If it's a job that pays by the hour, you bid your hourly rate; if it pays by the project or milestone, you bid your project rate. Then you submit and hope for an answer from the client.

Clients can also invite you to submit a proposal, but that has only happened to me once so far and the invite seems to have been sent out to anyone who listed "creative writing" among their skills. Invites probably come more into play as you gain more experience on Upwork, showcased via reviews from your clients, your job success rate, and your number of hours worked.

How I Came to Upwork. 

My Upwork profile.

My Upwork profile.

I created my Upwork account last year, soon after graduating college. I was looking for income, but wasn't sure what I wanted to do. I had several marketable skills: writing, editing, graphic design (particularly for print), and fluency in both English and Spanish. I had read that Upwork was a good place to get started as a freelancer.

I created an account and put my skills and experiences on my Upwork profile, but I didn't have the courage to submit proposals for any particular jobs. None of them seemed like the "perfect" fit and I hate marketing myself.

I was also applying to a wide range of jobs in my area, and around that time I landed a graphic design gig at a startup company. The pay wasn't spectacular, but it covered the bills and left me time to work on my novel on the side. I was also busy starting my blog, my YouTube channel, growing my Twitter and Instagram, and doing tons of research to help plan my writing career. I pretty much abandoned the idea of freelancing.

Fast-forward to about a month ago, when I started to feel antsy about money and about my career. I still had my graphic design job (and still do) , but we were in the slow season and I wasn't getting many hours, so I started thinking about freelance work again. I liked the idea of branching out, since my day job was pretty repetitive. I also loved the idea of working at home and being my own boss, at least for some hours of the week.

The Job Search Process. 

You can filter your results by number of proposals to make sure you have a shot at getting a job before you apply.

You can filter your results by number of proposals to make sure you have a shot at getting a job before you apply.

I freshened up my profile and started searching Upwork for jobs that fit my interests and skills. Upwork suggests jobs based on the skills you have listed, but I didn't find their suggestions terribly useful. Instead, I entered keywords that I thought would match me with jobs I would enjoy and be good at.

There are thousands of jobs on Upwork and you can easily feel overwhelmed. After all, you could lose hours and hours reading descriptions of jobs that might not even be right for you or crafting cover letters that will never be read. 

I narrowed down my search with Upwork's filters to make sure I only saw jobs I wanted and had a chance of getting. Apart from entering specific keywords (such as "typesetting" or “ghostwriting novels”), I filtered results by number of proposals. This meant I wouldn't even bother looking at jobs that had a ton of proposals already; since I'm a newcomer to the freelance world, I wanted to have a relatively good shot at getting a job if I was going to invest time applying to it. 

Qualifications I don’t meet, plus the number of proposals that have been submitted for this job.

Qualifications I don’t meet, plus the number of proposals that have been submitted for this job.

I also ignored jobs paying under $20 (or what seemed like way too little for the job, such as $40 to edit an entire novel) or with horribly misspelled or confusing descriptions and titles. There's a range of quality on Upwork, though I will say that in my searches, the ratio of bad versus decent jobs was never worse than 50-50.

I didn't bother looking at jobs for which Upwork flagged me as not meeting qualifications. Some of these qualifications include having worked a certain number of hours for Upwork, having a certain job success score, or being located in a certain time zone. The first two were impossible for me to meet, since I had yet to land any jobs.

Finally, and most importantly, I only considered jobs that I thought I would enjoy (or at least that I wouldn't hate). After all, I wanted freelancing to make me feel free. 

The Application Process. 

The space where you write your cover letter doesn’t seem to encourage long-winded pieces of writing.

The space where you write your cover letter doesn’t seem to encourage long-winded pieces of writing.

Having narrowed down my choices, I applied. It was scary to write my first cover letter; unlike with a cover letter for a regular job, I wasn't sure what was expected of this kind of cover letter. It was especially confusing when there were additional questions I had to answer that covered a lot of the same ground a regular cover letter would encompass.

As I applied to jobs, I started to realize a few of Upwork's quirks. Several job postings requested that proposals include a certain key phrase, presumably to weed out a good portion of applicants who don't read postings thoroughly enough. I suspect that a fair number of freelancers on Upwork send out blind proposals to a bunch of jobs with certain keywords. It may be possible to get some jobs this way, but I doubt they would be the best jobs.

You can bid a different amount than what the client has listed, but I’ve generally left the bid at the client’s rate. I don’t want to ask for more because I’m a beginner, and I don’t want to ask for less because Upwork jobs are already pretty low-paid.

You can bid a different amount than what the client has listed, but I’ve generally left the bid at the client’s rate. I don’t want to ask for more because I’m a beginner, and I don’t want to ask for less because Upwork jobs are already pretty low-paid.

I recommend reading the job posting thoroughly and using the cover letter to outline your relevant skills. Keep it brief. If there are other questions to answer, you can keep the cover letter to a few lines, since the same information will be covered in the questions. You can absolutely copy and paste parts of your cover letter from other proposals, since you’ll probably be applying to several jobs that have similar requirements, but make sure to tailor what you say to the particular job posting.

Your proposal will include some form of deadline you set for yourself. Give yourself more than enough time to finish the job. Nothing looks worse than late work. If you complete the work faster than what you said, you give the client a nice surprise.

After you’ve submitted a proposal, you wait for the client to contact you. This doesn’t mean you’ve got the job, even if the client shows interest in their message. I had a client say what amounted to “Awesome! I’m excited to work with you!” and then drop off the face of the Earth. You don’t have the job for sure until the client sends you an offer and you’ve clicked the “accept” button.

My First Job.

The job that came through for me ended up being the one I was most excited about. I don’t know if that’s a coincidence, if my enthusiasm showed in my cover letter, or if my experience simply lined up best with this job.

I’m still in the midst of this first job, so I’m sure I’ll have more to say once I’m finished, but so far it’s been a great experience. It’s a fiction ghostwriting job and my client has given me complete creative freedom. It’s the first time I’ve ever been directly paid to write, and it’s exciting and fun. It’s also going to help me make ends meet this month, which is a huge point in Upwork’s favor.

So… Is it Worth it?

It all depends on your situation. If you have established clients and/or a ton of freelancing experience, I wouldn’t recommend Upwork. If you need well-paying work right away, I wouldn’t recommend it. You need to be prepared to send a good amount of proposals to relatively low-paying jobs before you start building relationships and clout and can ask for higher rates.

On the other hand, if you’re interested in dipping your toes in the waters of freelancing, Upwork is a pretty good option. They take a significant cut of the money you make (20% for your first $500 with a particular client, 10% after you’ve made $500) but they do it in exchange for providing some measure of legal and financial protection. You can read more about it here if you’re interested. As far as I’m aware, Upwork is pretty secure.

Upwork is good for freelancers with beginning or intermediate skills in a particular area. There are jobs that require minimum expertise as well as more skillful jobs. You can even get paid to call a doctor in Italy and make an appointment for someone (that’s an actual job posting on the website). It’s a good place to start building a relationship with a client that might be starting out as well, because I can’t imagine that more established clients would need to post on Upwork to get freelancers.

It’s definitely been worth it for me, but I did put in a lot of time crafting proposals before I got my first job. Ultimately, it’s up to you whether you want to try it.

Leave a comment!

  • Have you worked as a freelancer? What has your experience been like?

  • Have you tried Upwork? Any positives or negatives I didn’t mention?

  • Would you ever try freelancing if you haven’t already?

  • Are you interested in more of these sorts of posts from me, either about Upwork or about some other aspect of freelancing and/or the writing life?