Reader beware:

This is an honest, epic blog post about whether Upwork makes sense for you. Upwork is not for everyone, but it is an amazing platform.

I put this particular post together to talk to people about one of the most popular online job boards known as Upwork, because I have had a great deal of success on the site myself.

That being said, there are a lot of stereotypes from existing or even new freelancers about whether it’s really beneficial to invest the time into putting together a profile on this site. Read on to learn more about whether it’s really worth your time to establish a profile on Upwork.

Even in 2017 and 2018, people will complain about Upwork. Most of the people who do this have not had success on the site. And not a week goes by that I don’t get a few emails reading something like this: “I applied to five Upwork jobs and didn’t hear back from anyone! Can you believe it?”

Let me tell you upfront, before we dive into the meat and potatoes of Upwork, that Upwork takes time. I submitted more than 40 proposals before ANYONE was interested in my work. However, after that, the floodgates opened.

And for most people who are submitting to a lot of jobs with no response, there’s something wrong with the pitch or work samples. The good news is that tweaking those can increase your conversions significantly. Being critical of my own pitches and proposals boosted my Upwork conversions to the point where I got fully booked.

(Insert Hallelujah chorus here, because at the time I was in a dead-end job. Boosting my Upwork conversions was the first sign I got that I could make a full time go of this freelance life. By the way… that was in the summer of 2012 and I’m still going, folks.)


How Upwork Functions

Some people may be completely unfamiliar with what Upwork means. It’s actually the newest version of two previous sites; Elance and ODesk, and these are both extremely popular online job board sites where clients would post essentially requests for proposals and then freelancers would respond with estimations of their time and the budget that they could complete the task in. It was sort of like a competitive marketplace for freelancers and it’s actually the system that I used to launch my freelance writing business in 2012.

Upwork Offers Peace of mind with its Payment Protection Mechanism

There are some things that make Upwork stand out as a phenomenal site to get work on, and then there are some things about it that can be a little bit frustrating or confusing especially for new freelancers. Some of the aspects that make Upwork an excellent choice for a new freelancer is that you have hourly work protection when you use the Upwork time tracker.

If you don’t use an hourly job and are instead using a fixed price job, you get the benefit of escrow funding. So before you actually provide a deliverable to a client, the client is responsible for transitioning funds into an Escrow account. Upwork holds those funds until it has been approved by your client to release them. As a new freelancer, it gives you a lot of comfort in knowing that some of the money has already been transferred in.

It’s also a lot easier to work on bigger projects with a total stranger when you have that sense of peace about the Upwork escrow funding or hourly protection services. It builds some of that trust between you and your clients.

Upwork is a Great Source of Leads & Makes it Easy to Connect with Potential Clients

Even five years into a fully-booked freelance writing business, Upwork continues to be an excellent source of leads for me.

It’s also so easy to connect to great clients whether you are looking for short or long term opportunities and that’s because Upwork is a leader in the field. Even though the site can be a little bit glitchy or confusing for someone who is using it for the first time, it’s also really easy to connect with clients because it’s the first place they look. So, individuals who are looking for graphic designers, web designers, virtual assistants, writers and a whole range of other freelancers will come to Upwork first to look for that ideal partnership with somebody else.

Just being on the site gives you the chance to participate in those requests for proposals.


There are some aspects of the site, though, that can be a little bit frustrating and having worked with the predecessors of Upwork as well as the version of the site now, I feel like I have insider knowledge about that.

Freelancers Need to Plan around Upwork’s Delayed Payment Schedule

One of the biggest frustrations is that payments can be delayed by as many as 6 days. Even if your client releases funds to you from escrow or hourly work protection, it’s put into a 5 to 6 day hold pattern by Upwork.

I am not entirely sure why they do this, as especially with an hourly job, you are already waiting for those funds to be released until the week after you have completed the work, and it can even be frustrating with escrow jobs as well because your client might not be available at the time that you submit a request for payment for freelance work.

It could be 3 or 4 days before they see your request for payment and then you are waiting an additional 6 days beyond that. From a cashflow perspective, that can be a little bit frustrating.

Be Prepared for Tech Glitches & System Downtimes

The site crashes a lot. It does however bounce back every time (at least so far.)

Anyone who used Elance in the past is probably familiar with the fact that Elance went down every so often. Sometimes it was planned and many times it wasn’t. There were technical bugs and glitches that were part of the Elance system for a long time.

Unfortunately, I think it’s actually worse on Upwork. It constantly confuses your client account with your freelancer account and it can just be really difficult for new clients to use the site because it crashes a lot.

One of the things that I recommend for people who are using Upwork for the first time is don’t count on the Upwork messenger service as the be-all and end-all to deliver your communication.

Sometimes messages never show up in my email even though the Upwork mobile app shows them as being there and when I log into Upwork I can see them there.

I strongly recommend logging in daily if you are active on the site so that things don’t slip through the cracks.

The Upwork Interface is Not Intuitively Designed

The site design is also very frustrating because it’s really hard to find past files. In the Elance version of this system, you could always click on files and you could see every file that had ever been uploaded to the workroom.

Even though I have transmitted plenty of files through the workrooms in Upwork, it sometimes does not show properly in the actual messaging center itself. That can be pretty frustrating and confusing especially if you have submitted work and a request for payment and the client just hasn’t seen it because there is a glitch.

The site has gotten better, but some aspects of its design are not user-friendly. It’s not an easy platform for you or your client to use, but it’s hardly impossible – you’re going to have to take the time to help train your clients on how to use the site as a lot of them would be confused or find it frustrating.

I usually keep communication off the Upwork platform. Use it for the purposes of escrow funding and the hourly payments but honestly, it’s so much easier to communicate by email than to try to find lost messages on Upwork.

Learn to Spot & Avoid the Low Quality Jobs

It’s certainly not true 100% of the time, but a lot of the clients on the Upwork platform are looking for rock bottom prices.

There are some wonderful jobs on there and some really high quality clients too but there are also plenty of people who want to pay $1 for a full length blog post or $20 for a brand new design for their logo – which is just crazy.

Even though there are overseas individuals who are willing to offer it at that price, it really just drags down the rest of the market because signing in and seeing that makes you as a freelancer say, “Whoa! My expertise and talent is not really valued here.”

That said, if you can look past these job posts and focus only on the good ones, you can find something valuable.

By the way, I’ve heard some freelance coaches and other freelancers avoid jobs that have $5 listed as their budget. Be aware that that’s because, in some cases, the client doesn’t know what they want to pay. The minimum budget a client can list is $5, so you should not always assume that $5 is what the client really wants to pay.

This is even more important as lower-paying clients will not hit the $500 threshold to trigger the Upwork fee being pushed down to 10%. Instead, Upwork’s cut will be 20%. Be aware of how this can impact your earnings.


How to Use the Site Effectively

If you are new to the Upwork platform and you are a virtual assistant or any type of freelancer, there are a couple of things that you can do to make it a little easier for you.

First of all, ignore the bad jobs. You are going to get invited to them and you are going to see them in your search results. Don’t even waste your time.

Also, decline invitations to low paying or poorly suited jobs. The client might never get the message but I would rather tick off the box that says the reason I am declining this is the budget is too low. Over time, the client will learn that paying so poorly for work means people don’t even want to submit a proposal.

It’s entirely in your control which jobs you submit a bid on and I get it- when you first get started, it’s really tempting to apply for everything but remember, you actually don’t have to. If it’s not suited very well to you or if the client seems very difficult or wants to pay the lowest possible price, just move on.

A couple of more tips if you are planning to use Upwork as a site where you’ll be submitting bids for freelance jobs.

You need to make sure that your profile is directly aligned with your ideal clients. (Tip: You can access my latest resource ‘9 Six-Figure Changes Your Upwork Profile Needs’ via my Freelance Marketing Mastery Facebook group today! Just click the button below.)

The pitch and work samples that you submit should also be right in line with who you are targeting.

Make sure you speak professionally to all clients.

Submitting generic proposals rarely works. In fact, doing this can turn a client off very quickly.

And it also needs to be very easy for a prospective client to read your writing and to understand the value that you offer.

I have had the chance to look at a lot of proposals submitted on the Upwork and Elance platforms and all too often, the reason people are not landing jobs on those sites is because of how they are submitting proposals.

Take a really critical eye to the information that you are providing and have someone else look at it as well.

Scope out your competition too to see what they are doing so that you can refine your own work.

There are a lot of challenges in joining a site like Upwork when you are brand new and don’t have the experience. First of all, it’s difficult to know how you are should be priced to be in line with what everyone else is providing. It’s also really hard for that first person to give you a job when you have no reputation or background on the site. And then, of course, you are competing against other individuals who are really talented. It’s a competitive environment.

That being said, all of these things can be overcome.

I took my writing business from earning $150 in my first week to becoming a top 1% company on Elance and being ranked the number 5 writer on the site overall in just a couple of months.

It’s definitely possible to achieve but you need to understand how to make the system work.

If you’d like to learn more about succeeding on Upwork, you need to understand as well that it needs to be simple for your clients to hire you. You can’t think all about how you want to succeed on the site without thinking about how the client perceives the material and the pitch that you are sending to them.

Don’t overwhelm your clients. Sending too many materials is actually worse than sending too few.

Remember that clients can get dozens of responses to a request for proposals so it needs to be really crystal clear, the value that you offer and just a few work samples are all you need to show that.

You also should talk about how you can share your unique value proposition.

As I mentioned before, it’s a competitive environment but you can stand out by being really knowledgeable about what you have to offer. Your work samples or your references should always be top of mind when you are submitting a proposal on Upwork.


You’ll find all my best advice about building a fulfilling and sustainable business here. It’s where I’ll give you all the juicy details about building a strong digital team or using project management to stay on top of tasks.

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