My Experience As An Upwork Freelancer: The Story So Far

By Hollie

As the largest online freelancing platform in the world, Upwork is a brilliant place to start if you’re a skilled professional who has decided to make their way as an independent freelancer.

Upwork is an online job portal, so it can also give you the opportunity to become location-independent, gaining the freedom to move abroad or work while you travel.

Personally, Upwork has given me incredible opportunities as a newbie freelancer that I would have struggled to find elsewhere, and I can gladly report that my experience has been generally positive.

Having been using the platform for nearly three years now, I decided it was time to write down and share my experiences as an Upwork freelancer for those of you who are interested in giving it a try. If you have any questions for me, please don’t be shy – pop them in the comments box below!

What Is Upwork And How Does It Work?

Upwork is the world’s work marketplace for freelancing. (Their words, not mine.)

The platform allows clients and freelancers from all over the world in a multitude of different professions to find each other and work together on projects.

Here’s how it works in simple terms. A client posts a project (an advertisement I guess), freelancers apply by writing a short cover letter and submitting a bid, the client interviews freelancers using the built-in messaging and/or video call function and then selects the freelancer they think is the best fit. A contract is offered, the freelancer accepts or negotiates the terms, the project begins and work is completed, submitted and paid for.

From beginning to end, the whole transaction takes place within the platform. Upwork provides the contract, holds funds in escrow (for fixed-price projects), offers time-tracking functionality (for hourly contracts), issues invoices, collects feedback and settles any disputes that arise.

There are a few other ways to get hired on Upwork (I’ll go into the details in a separate article), but all in all, this can be a one-stop shop to making it as a freelancer. It’s completely and utterly brilliant if you can make it work for you.

How I Ended Up As An Upwork Freelancer

I never expected to be using a platform like Upwork, nor did I ever really expect to become a freelancer – much less be my own boss – but life took an unexpected turn in 2020 when the global COVID-19 pandemic put a hold on my travels and sent me packing back to the UK without a job.

During the six months I spent travelling through Southeast Asia, Nick and I would often fantasise about a life where we didn’t live and work in the UK. Upwork was on my radar by that point, but I still planned to return home after my travels and find work in the conventional way. As it turned out, the pandemic provided the perfect opportunity to pursue an alternative approach to work, and as we still had a small safety net of unspent travelling money, I decided to take the plunge and throw myself into the topsy-turvy world of online freelancing.

My work experience prior to Upwork had been very traditional, in the sense that I was one employee amongst many in a medium-sized organisation, reporting to a line manager and commuting to the office every day where I worked at a desk 9–5.

Fast-forward three years and I’m sitting at my laptop in an Airbnb in Kuala Lumpur, Malaysia. The sun is shining, it’s roasting hot outside and I’ve spent the day working for a friendly and reliable client who I’ve now been working with for a year. I’ve enjoyed my day and the freedom it has offered me – and the best part? There’s no office politics, no set working hours and no draining commute home. I’m in control.

After nearly three years of being a freelancer, I’m making a comfortable living and I have clients who value my contributions and expertise. I’m certainly not making millions, nor am I working three-day weeks. I think relatives and friends (and indeed followers of We Might Just Go) assume Nick and I are enjoying a permanent holiday, but this couldn’t, unfortunately, be further from the truth. Holiday? What’s a holiday?! I can’t remember the last time I took any serious time off! Negatives aside, I’m still pretty shocked that I’m actually earning more than I did in my last full-time employment. And some days I still feel like this isn’t a real job.

Upwork has given me the freedom to do something that makes me feel truly accomplished and proud, all while enjoying a lifestyle I’d always dreamed of and spending lots of quality time with my partner. My experience hasn’t been plain sailing, and I have plenty of criticisms of the platform (more so recently) – but more often than not, Upwork makes me feel safe, supported and listened to. Plus, it allows me to find inspiring new clients and work on amazing projects that I don’t think I would find elsewhere.

Signing Up And Getting My First Job

Let’s rewind three years to when I first started as an Upwork freelancer.

I found the process of signing up quite simple and it wasn’t long before I had my application to join Upwork’s network of freelancers accepted.

It’s important to note here that not everyone is accepted. You need professional skills and you need to have some experience of applying these in a professional setting. You can be a newbie freelancer – that’s fine – but Upwork is known to reject applications from people they don’t believe will bring professional value to the network. Not enough in my opinion, but still.

The challenge for any new Upwork freelancer is trying to find those all-important first jobs. You might have just left your position as a highly-respected marketing manager with 10+ years of experience, but to many Upwork clients, you’re still a newbie and they’d prefer to hire freelancers with Upwork experience – or freelancers who say they can do the same job as you for a fraction of the amount you’re charging.

In the early days, I was applying to jobs I was way overqualified for that were paying pennies. I also succumbed to the temptation of starting out with a crazy-low hourly rate on my profile – $15 I think. My first job paid me the grand total of $5 to proof-edit a five-page document. After Upwork’s fees and the exchange rate, I made £3.08. Oh the shame. But considering that was the first money I’d earned in six months, I remember feeling pretty chuffed!

The thing is that, for me, this approach worked. It enabled me to make valuable contacts, gather gushing reviews, and most importantly, it allowed me to figure out the whole Upwork ball game as quickly as possible.

However, this was three years ago. Getting established on Upwork today isn’t so simple. Not only are there lots more freelancers on the platform, but the way the platform works has changed slightly. AI matches freelancers to jobs, and there’s now something called ‘boosting’, where you bid (potentially lots of Connects – a type of in-platform currency) to appear higher on the client’s list of applications. This is making things very, very challenging.

Many experienced Upworkers will tell you not to undersell yourself. They’ll advise you to set a realistic hourly rate, even as a newbie, and not to encourage greedy clients to hire talent for insulting fees. I get it. With so many freelancers working for low fees, it makes those who charge realistic prices undesirable. I feel a little ashamed now that I was one of those sell-out freelancers. I sold myself short and worked for pennies just to receive a few 5* reviews, but ultimately, that decision got me to where I am today.

It’s worth mentioning that a few years on, I wouldn’t dream of applying for a job that didn’t meet my expectations in terms of pay. I’m also incredibly fussy about which clients I work with!

I often wonder what would have happened if I’d decided to hang on and keep applying to decent-paying jobs with good clients. It would have taken a lot of courage and perseverance, but perhaps I would have made more progress in the long run. Someone would have given me a chance I guess – eventually.

To be completely honest though, that first $5 job and other early projects did wonders for my confidence and gave me the opportunity to figure out freelancing – how to talk to clients, how to use Upwork, how long tasks take me, what tools I like using.

Ultimately, I had all the professional skills I needed to sell copywriting and editing services, but I had none of the skills I needed to actually freelance.

New freelancers rarely have pricing strategies worked out anyway. That comes with months of experience and spreadsheets, so unless you are an established freelancer tackling Upwork for the first time, it makes sense that newbies would charge lower rates.

But $5 is ridiculous. Don’t do that.

My Worst Upwork Experience

My experience with Upwork so far has been really positive, but there have been two occasions that really shook me. Both were my fault…

The first was when I accepted a contract without discussing it with the client first. I think I was just so eager to get a job on the platform, as starting out is such a struggle. This could have had major repercussions for my JSS.

Just quickly, JSS stands for ‘job satisfaction score’ and it’s the bane of an Upwork freelancer’s life. Nobody really understands how this score – a percentage – is calculated, but it reflects your client feedback and general success on the platform. Basically, you want to keep your clients really happy and never risk your standing on the platform by a) submitting shoddy work or b) getting involved with an awful client.

I did the latter. I applied for a job and immediately received an offer. It was a good offer for ongoing, irregular work, but I accepted it without discussing the job with the client first. Rookie mistake if there ever was one. It was in the early days and I was just delighted to have won the bidding war, so I made a stupid move.

I found myself in a contract with a client who then ignored me for days – DAYS – without any work or even a message to say ‘hi’. I was confused and in total panic mode. Inactive contracts harm your JSS you see, so this scenario was far from ideal. It was also a huge professional risk. My understanding of the job (based on the few lines posted in the job ad) could have differed wildly from that of the client. Job ad descriptions are usually quite vague, as was this one, and usually, the job parameters and requirements are unravelled in the interview process through discussion and professional guidance from you as the freelancer.

Long story short, the client responded – eventually – with instructions for an enjoyable task very much as described in the ad. The client was a bit allusive but that’s not unheard of. After that first task, they went silent on me – completely silent – despite having promised more work. Again, this isn’t unusual. Eventually, I closed the contract myself due to the client’s unresponsiveness. There was no harm done as technically I had fulfilled my end of the bargain. I was lucky.

My second bad experience was when I took on a test job that resulted in negative feedback. I say negative – publicly, the client rated me 4.6/5, but privately (oh yeah that’s a thing) they rated me less than 5/10 which is classed as a non-recommendation. I don’t know what the issue was. They gave me good feedback in our messages. Clearly my style of proof-editing wasn’t what they were after, or perhaps they just preferred one of the other (possibly cheaper) freelancers they were testing, but boy did that feel like a betrayal. The lesson I learnt was not to take on ‘test jobs’ quite so freely – they are quite risky. Perhaps that subject is for another article too.

As you can see, these two ‘worst’ experiences were very tame. I know I’m too sensitive. Generally, I’ve been very lucky and have maintained a stellar profile throughout my time on the platform.

Things I Like About Upwork

I thought the best way to close off this ‘My Experience as an Upwork Freelancer’ article was to jot down a list of the things I like most about the platform. So here goes:

• I feel/am protected in case things go wrong. With Upwork, money earned is money paid. You don’t get this with other platforms like PeoplePerHour.
• The platform is easy to navigate and use.
• I feel supported and I know I can reach out and talk to someone if I have any questions.
• Upwork makes me feel optimistic and encouraged. They send cute little emails at earning milestones and anniversaries.
• The Upwork community forum is really insightful and helpful.
• Apart from a few quiet periods, I’ve never found it difficult to find work (however, it’s now 2023, and I think it’s becoming more challenging).
• I’m in control of my earnings, despite commission fees.
• The platform has introduced me to wonderful clients with inspiring projects!

Things I Don’t Like About Upwork

Now for the negatives:

• Upwork allows low-quality clients (those who abuse the system, scam freelancers or expect work for free) to join the platform without effective vetting. This isn’t a problem if you know how to spot said clients, but they shouldn’t be on the platform at all.
• The platform has a useless skill level function. You can either define yourself as ‘beginner’, ‘intermediate’ or ‘expert’, but this means nothing when clients are permitted to post job ads in which they seek an ‘expert’ who will work for $3 per hour. More guidance and restrictions are needed, I think.
• Recently, Upwork is being monetised more and more (through features such as boosting), and it feels a little like they’re trying to profit from freelancers’ desperation.
• There are too many freelancers and not enough clients, according to Upwork’s own reports. Upwork allows too many unqualified freelancers to join the platform.
• Upwork has recently made a decision to increase commission fees on certain contracts, meaning many established freelancers will see their earnings reduced from 2024. This is the single worst decision Upwork has ever made and will be devastating for many freelancers like me. More on this below.

A 2023 Update: Is It Time To Look Elsewhere?

Until May 2023, Upwork had a three-tiered commission structure. It worked like this:

20% for the first $500 billed to a client

10% between $500.01 and $10,000 for that same client

5% for billings that exceed $10,000 for that same client

However, this is changing. From May 2023, there will be a blanket commission fee of 10%. I don’t necessarily think this change was needed from a freelancer’s point of view, but it will certainly benefit freelancers who mainly take on small, low-value contracts. For example, if you only ever do small, one-off jobs that are worth $100, you’ll always be stuck on the 20% rate.

So why do I think this is the single worst decision Upwork has ever made?

When I saw the announcement for this change, it took a little while for the implications to sink in – for me. My largest client on Upwork is a 5% contract, and my second-largest client is heading that way. So the amount of commission I owe Upwork on my two largest contracts has effectively doubled. Yikes.

Upwork announced that they will be honouring the 5% rate until 2024. It will increase to 10% thereafter.

The Upwork community forums are in uproar. Why? Because suddenly, thousands of freelancers who earn their livings on Upwork are going to be out of pocket; some, by a lot of money. Many clients will be receiving price increase notices from their freelancers to cover the commission hike, which may prompt them to leave Upwork altogether. Meanwhile, freelancers will be taking established relationships off Upwork if they have been working with their client for over two years (when the non-circumvention period ends). I and many others think that, ultimately, Upwork will lose money from this decision. That’s quite a problem for a company that isn’t even profitable. (Yes, you read that right.)

Ultimately, this isn’t good for anyone – freelancers, clients or Upwork.

I think I’ll continue to use Upwork to find new clients when I need to; I’ll just factor the commission increase into my rates. However, I have no desire to keep my existing high-value contracts on the platform. When two years are up, I’ll ask them to consider leaving.

I’ve sort of lost respect for the platform with this announcement, as have most freelancers. I really hope they reverse their decision and honour the 5% commission rate on eligible contracts indefinitely.

My Experience As An Upwork Freelancer: Summing Up

I have loved using Upwork over the last three years. The positives, for me, have always outweighed any negatives. It has given me an opportunity that I perhaps would never have been given elsewhere, and I have met some truly outstanding professionals and worked on incredible projects.

However, recent announcements have really made me question my loyalty to Upwork. It’s also clear that it’s becoming much more difficult to succeed on the platform – something Nick will talk about in his own blog post as it’s something he’s contending with right now as a new freelancer to the platform. Even top-rated freelancers with hundreds of thousands of dollars earned are struggling to find clients, and it’s no surprise given that Upwork themselves admit that there are too many freelancers and not enough clients.

I think any freelancer’s experience of Upwork will depend on the way in which they handle their business. That sounds obvious, but if you make stupid business decisions, such as working for free, bidding a rate that’s too low (or too high), getting involved with a dodgy client, or taking on too much work at once, you’re never going to have a good experience, whether you’re on Upwork or not. Ultimately, my only bad experiences have resulted from my poor business decisions – Upwork was clearly not to blame, and even then they weren’t that bad.

To find success on Upwork in 2023, you’ll need a bucket-load of patience, a willingness to invest in Connects to get your proposals seen, and the dedication to create an epic profile and submit stellar applications. But more than anything, you’ll need to be the real deal and have legitimate skills.

If you have any questions about getting started as an Upwork freelancer, please feel free to get in touch. Nick and I both have different perspectives and tips to share, he as a newbie Upworker and myself as an established ‘top-rated’ Upworker.