In this post, I am tackling the number one question that I get (in emails, YouTube videos, you name it); “How many jobs do I have to bid on with Upwork in order to actually land one?!”

How Upwork Functions

Let me explain how Upwork functions and how you need to view it as a freelancer.

A Job Posting is not a guaranteed hiring opportunity 

Generally, people who post a job on Upwork are interested in hiring a freelancer; they’ve gone to the trouble to set up an Upwork account, to post a job etc. However, there’s no guarantee that any of those people are ready to hire or ready to move forward with you.

When a client goes on Upwork and posts a job, they may or may not be ready to actually hire somebody. Sometimes people post jobs as a way of researching the general price range. They’re trying to see if there is someone out there for an upcoming project. They might be trying to establish if it’s cost effective to hire a freelancer as compared to doing it themselves or keeping it in-house. Or it could just be an assistant posting on behalf of his or her boss, and rounding up the best interviews for the boss.

So if you have only bid on 10 jobs and you’ve heard nothing, welcome to Upwork. 

If you are new to the platform and have never bid on jobs before, you’re going to have to spend a lot more time writing proposals than an experienced freelancer. The way that I use Upwork is going to be really different from how someone new to the platform would. 

You’re going to be getting practice writing proposals, you’re going to be bidding on a lot of jobs. That doesn’t mean that you should be getting a lot of responses; some proposals and jobs on Upwork get upwards of 50 responses from potential freelancers, so there’s also always the chance that a client who’s viewing it sees all these proposals and just gets overwhelmed and says, ‘Okay forget it, I can’t deal with this right now.’

Bidding Early Can Work in Your Favor 

Now if you do bid early on jobs and somebody responds to you right away, that’s a pretty good indication because they’re still on the platform, they’ve read your proposal already and they are writing to you. So it is always in your best interest to bid early.

That’s not to say you can’t land jobs that have been posted for a while. I’ve landed jobs that were posted a month prior and I just saw them and applied to it. So it really depends. Sometimes I’ll say, I really need to do XYZ project… I’ll post a job on Upwork and leave it for a week or two, because I’m letting those proposals come in or perhaps I just don’t see somebody who’s a fit.

So there are many reasons why a client won’t respond or won’t hire you. First of all, someone else could be a better fit – they may have had a better presentation, better price, better deadline. Whatever it was, they could have edged you out. The client might have gotten overwhelmed by the platform. Another common reason is that people are just too busy or not ready to move forward with hiring yet; maybe they need to run the quotes by their boss, they need to talk about it with their marketing team, whatever.

Your Samples And Proposal Must Help You Stand Out From the Crowd

With Upwork, 1 to 2 out of every 10 jobs you bid on is somebody who’s ready to hire today and even then, they may hire somebody else. Most of the time, when I ran into freelancers who were bidding on Upwork actively and getting no response — it was usually that their samples weren’t great and/or their proposal was 100% generic.

So if you’re the person on Upwork who is bidding on a writing job and you respond to the job proposal by saying, ‘I’m a good writer, I really love writing, I can write this for you’ … congratulations, 50 other people have literally said the exact same thing and you’ve done nothing to make yourself stand out from the crowd. 

You Must Bid Consistently

There’s no one magic answer about how long you need to be active on Upwork, or even how long you need to be involved with bidding actively but when I get these emails that say, “I bid on five jobs on Upwork and I have gotten no response,” this is not surprising to me because it can take dozens of proposals to actually turn it into a paying position.

The first time that I ever bid on jobs on Elance, it took me 36 proposals before I even got one person who was interested. So what matters on Upwork is consistency. It matters that you’re going to spend the time to consistently bid on jobs. Every day, you’re going in there and saying I’m going to do 10 proposals or I’m going to spend an hour doing this.

And you are writing really thoughtful proposals that are directed to the client. Do not just say, “I’m a good VA, I like design, I’m a voice over artist.” – that’s all implied in you bidding on the job. Please say something that makes you stand out. It could be that you have openings in your schedule now and you can do something in the next 48 hours; it might be that you can beat somebody else on price because you’re new and you’re trying to get experience; it might be that you’re more qualified than another person. Think about what’s going to set you apart.

If You Don’t Get The Result You Want, Re-evaluate Your Proposal and Review Your Pitch

If it takes you 30 or more proposals to land your first gig, that’s probably not that uncommon because remember, only one or two out of every ten are actually going to be someone who is going to be ready to hire. Then you have to factor in the competition from other people on the site as well.

But if you get past that 30-pitch mark and you’re hearing nothing, take that as a sign that you need to be very critical of your proposal. Are the samples that you are sending out to clients the absolute best that you have? Is that proposal thoughtful or is it a copy paste generic? I cannot tell you how many proposals that I’ve seen on Upwork – to me when I’ve posted a job, and they say, ‘Dear Sir’ when it’s totally obvious that my name is Laura and I am a woman; there’s no reason you should be calling me ‘Dear Sir’ but instantly when I see that, it’s like I’m not working with you because you didn’t even take the time to spend 5 seconds to figure out that I’m not a ‘Sir’. And it goes beyond obvious mistakes like that too.

When I post a job on Upwork and see the response from potential freelancers, a lot of time it’s just so generic — I am not given a compelling reason to hire freelancer 1 versus 2, 3, 4, 5, 6 or 7. There’s no differentiating factor and I think that’s a major reason why I’m able to get my clients on the phone, I’m able to get my clients to a private conversation where we’re talking about me doing the job. It’s about getting that client from just reading your proposal to saying, “This is the person I need to work with. This right here is the clear winner amongst all the other proposals that I have looked at.”

So if you’ve done 30 proposals and you’ve heard nothing, re-evaluate your samples, re-evaluate the proposal you’re sending, review your pitch. We have nine changes that you need to make to your profile in a PDF, that will help you come across as a super professional.

It’s also harder for VAs to come up with samples than it is a graphic designer or a writer, but you can still do them. Make something up, show the client what you can do. Just make up a research project and say that it was something you were asked to do; I was asked to find the cheapest flight from San Diego to Hong Kong, and here’s what I found. Clients just want to assess if you have the required expertise. So many freelancers make that mistake of being super generic and then they’re just throwing spaghetti at the wall — they’re sending a bad proposal to dozens of people and then getting frustrated because they’re getting no response.

Well there’s two problems there. You have to be consistent with it and second of all, your proposal needs to actually be good in order for somebody to think about hiring you.

I once had a student who was on Upwork/Elance for over 2 years and had never landed a job. When I reviewed her material, I found both a proposal and pitch problem. We fixed it and she landed two jobs within 48 hours. So if you are bidding and not getting anywhere, don’t automatically blame the clients, or Upwork as a platform. Consider that perhaps there is something you’re doing that is not presenting a compelling picture. Go back to the drawing board and try something different.

I tried so many different things when I started out as a freelancer on Elance and on Upwork. I pitched myself as a company, I pitched myself as an individual, I focused on the PhD aspect and then I would say, well let’s see, if I say that I’ve worked in law firms for 8 years, and I would test to see what worked best. So if you’re not getting a response – and you’re bidding a lot – adjust your system. Figure out what it is that you can do differently and test it; say, for these next ten proposals and see if that gets a response.  Whatever the approach is, try doing some different things to get different responses, different reactions and different feedback from people. Once you find something that works, capitalize on it.

I really encourage you to let this advice settle in and be open to revising your stuff. I revise my pitches all the time, I revise my writing samples at least every 6 months. Why? Because we get better, we change our focus, things are different, we might be trying to attract a new group of clients. So be self-reflective and be critical and say this isn’t working; I’ve done dozens of pitches and I’m seeing nothing. Let me go learn from some people who are pitching masters at this.


Let me know what questions you have about Upwork after you’ve had the opportunity to digest this a little bit. If you are out there in the trenches and you’re bidding regularly, keep it up. You will not land jobs unless you are regularly pitching, especially if you currently have zero clients, you need to be pitching more than anybody else. Good luck!

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