7 Expert Upwork Tips for Beginners (+ 9 Mistakes to Avoid)

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Getting your first job on Upwork, or even your first few jobs, is hard. 

So much so, in fact, that many freelancers end up quitting after sending in a few applications without a response. 

I get it. I was there too. It’s frustrating. 

Upwork was one of my first big side hustle successes. I was able to go from beginner to earning over $100+ an hour designing landing pages.

But it didn’t happen overnight.

On the flip side, as someone who has spent over $80,000 hiring freelancers on the site, I’ve also seen my fair share of mistakes when it comes to proposals. 

Since many of these hires still work with me today, helping to produce the content here at The Ways To Wealth, we put our minds together to come up with seven expert Upwork tips to help ensure your success. 

Here’s what you can expect:

• Why exactly getting that first job is so difficult.
• The secret that freelancers use to land their first job when they don’t yet have feedback.
• Seven expert tips for getting high-quality, highly-paid jobs on Upwork as a beginner.
• The top 10 mistakes to avoid on Upwork.

Note: In addition to these tips, we published a companion guide that goes into detail about how to get your first job on Upwork.

Let’s get started…

Why Getting Your First Upwork Job Is Hard

For the time being, put yourself in the shoes of the individual who is creating an Upwork job post. 

First things first: you’re trying to find someone you can count on to deliver the results you want. 

The job post has 20+ applicants — sometimes 40, 50 or even more! 

How are you going to sort through and make a decision about which freelancer is best? 

On Upwork, most jobs are chosen based on feedback. 

If a potential freelancer has good feedback — which is a combination of Job Success Score and written feedback clients have shared on the freelancer’s profile — you’ll consider them for the job.

In other words, you’ll take a look at their profile, read their proposal, and maybe start a conversation. 

But if they don’t have much feedback — or worse yet, if they have some negative feedback — those things are unlikely to happen.

This is where most beginning freelancers stop and ask (often in frustration):

So how do I get a job without positive feedback on my profile, when I’m competing with dozens of others who have great profiles?

Here’s the answer…

How the Upwork Feedback System Works

First, know that feedback on Upwork is a combination of two things:

#1. Your Job Success Score.

This is a metric Upwork created to measure client satisfaction.

After you complete a job on Upwork, the client is taken through a series of questions. They’re asked to grade you on a scale of 1-10.

These scores, along with some other technical factors (like whether the job was delivered on time) determine how successful the project was.

These ratings do not appear on your profile, but are rolled into your Job Success Score (which shows up when you apply for a job).

#2. Written Feedback

In addition to leaving a rating, clients are also asked to leave a comment on how well the project went. These ratings appear on your profile. 

Here’s an example from a past job of mine:

You’re probably wondering why we’re focusing on feedback when you don’t have any. 

It’s important because you need to understand the buyer’s mindset. A buyer wants to hire a person they trust, and the shortcut to hiring someone they feel they can trust is reviewing the freelancer’s feedback. 

So here’s the big secret to getting hired for your first job: You need to establish this type of trust in other ways outside of Upwork.

7 Upwork Tips for Beginners 

It’s all about trust. The more a client trusts you, the more likely you are to secure the job. 

Here’s how to establish that trust outside of Upwork’s Job Success Score and feedback system. 

#1. Complete Your Profile (and Make it Awesome)

When you have no feedback, your Upwork profile is the primary thing prospective clients will use to evaluate your fitness for the job.

When creating your profile, assume your client is making a split-second decision with regard to wanting to learn more about you. If you don’t make your profile stand out, they’re on to the next one — and quickly. 

Again, looking at things from the client’s perspective, their first impression of you occurs in the “Review Proposals” tab. 

Here’s what this looks like from the client’s side:

The client sees your profile picture, your name, title, location, Job Success Score and a snippet of your cover letter. 

While we’ll discuss the cover letter (i.e., the proposal) later, there are two important things to note here:

#1. Your profile photo.

Act like you’re applying for a job with a Fortune 500 company. What would their immediate impression be based on your photo?

This doesn’t mean it has to be boring. As an example, if you’re looking for creative work (such as freelance graphic design jobs), your professional photo would be different than someone looking for accounting work. 

Does your current profile photo pass the Fortune 500 test?

#2. Your title.

This is one of the most underutilized customizations you can make to your profile. Ideally, your title should let your client know why you’re perfect for the job. 

A good title starts with picking a good niche. 

Most of my success on Upwork was when I offered conversion rate optimization services on the Unbounce design platform. 

While what I did was web design, when I wrote my title, my goal was to let the client know I was a perfect fit for their job:

What you want to avoid is branding yourself as a generalist. Because there is so much competition, generalists typically don’t get hired on Upwork.  

Pro Tip: Because there are so many applications, assume your client is skimming through freelancers. What can you say in the title to quickly let them know you’re perfect for the job?

#2. Look for a Small Project and Bid Low

With my first job on Upwork, I made $50 for what was close to 10 hours of work on a copywriting project. 

It’s not ideal to work for less than you’re worth. But it’s a necessary evil when starting out on Upwork — at least if you want to get up and running as quickly as possible. 

Pro Tip: My strategy was to bid well below the client’s budget and ask them to test me out vs. the experienced copywriter they had previously hired. They liked what I did better, and that was all I needed to build some momentum and get started as a copywriter. If you’re confident in your abilities, asking a client to hire you along with a more experienced Upwork freelancer can help you land that first job. This strategy doesn’t work in every industry, but can be used more often than not. 

For your first job, don’t put much stock into your hourly rate. Instead, think long-term. 

Have the mindset that it’s not your first job where you’re going to get paid what you’re worth, but the third, fourth, fifth and so on.

At the beginning, the goal is just to get established; to build that feedback profile we discussed earlier so that you have a better chance to win more jobs.

That also means that when starting out, your focus should be on shorter-term projects on Upwork. 

This benefits you because you’ll be able to earn feedback quicker. 

Also, the client is more likely to test out someone new on a short-term project vs. a long-term one. 

This is a better strategy than bidding low on a bigger project, for two reasons: 

1. You limit the amount of work you have to do for a low rate. 
2. Clients won’t want to hire a questionable candidate for an important project, even if the price is low.

Related reading: Fiverr vs. Upwork for Beginning Freelancers

#3. Look for Clients Who Leave Quality Feedback

It’s a fact that some clients on Upwork are, let’s say, “pickier” than others. 

In other words, not every client will be a pleasure to work for. 

Plus, not every client understands just how important feedback is for freelancers; they may see it as their responsibility to nitpick and point out the pros and cons of working with a given freelancer, when in fact the industry standard is to leave a five-star review unless there was a serious problem.

Fortunately, there’s an easy way to tell which clients are worth submitting a proposal to: just look at the feedback they’ve left for others.

Remember, your goal at the beginning is to earn positive feedback fast. So, look for a client that consistently rates the freelancers they work with five stars. 

These clients are not only more likely to give you five-star feedback, but they’re also more likely to be very clear on what they want from you. In turn, you can deliver the exact results they’re looking for. 

On the other hand, if you see that a client consistently leaves mixed reviews, you might want to avoid those projects. Chances are they’re difficult to satisfy, and getting negative feedback on your first few projects can significantly derail your Upwork career.

#4. Use Your Cover Letter to Start a Conversation With the Client

Your cover letter — and specifically, the first 3-4 lines of your cover letter — is another chance to make a great first impression on the client. 

Looking at our example from above, an excerpt from your cover letter is included in the proposal screen:

The first goal is to make it known that you’re not just submitting a templated proposal. 

Your proposal should be clear and concise, directly address the client’s needs, and offer a concrete next step. 

Here are a couple of tactics that can help you accomplish this:

• Address them by their name. Do some research on who is hiring. Click on the prospective client’s profile. If their name isn’t on their profile, and instead you see a business name, you can often find the client’s name when checking out the feedback other freelancers have given.
• Start strong. As the first few lines of your applications will appear on the application screen, make sure your application immediately explains why you’re right for the job. One simple way to do this is talk about your experience outside of Upwork. For example: Hi John! I’m new to Upwork but I have five years of experience in XYZ.

Most importantly, what you’re trying to accomplish with your proposal is to start a conversation. 

Asking a client to hire you based on your proposal alone is often a giant leap. So, don’t just submit it and pray they get back to you. Instead, make it easy by starting a conversation. 

The best way to do this is by asking a question. 

For best results, ask a question that displays your understanding of the work. 

For example, if it’s a freelance writing gig, you can say something like:

“I’ve long admired what this [example site] is doing in your niche. Is this the type of content you’re looking for, or would something like [example site’s content] be more in line with your goals for this project?”

Pro Tip: The strategy I used to land my first long-term, highly-paid gig ($2,000+ for writing an e-mail series) with less than five successful jobs on my profile was creating a quick video for a prospective client. (I listed it on YouTube, as a private video that only people with a link could view.) It was around a two-minute video, recorded via webcam. I introduced myself to the client, and let them know why I was right for the job. The client was looking for a specific type of e-mail funnel, and it just so happened that I had recently finished reading a book on that particular method. So, I was there in the video holding the physical copy of the book, explaining why I was the best person for the job.

#5. Offer a Detailed Plan of Action

A great way to build trust in your proposal isn’t just telling your client you can do the job. 

Instead, offer them a detailed explanation of how you will go about accomplishing your work. 

Using freelance writing as an example, discuss how you would go about researching the topic, how you come up with different subheaders, and how you get expert sources.

Similarly, when I was doing landing page design, I’d talk about how I’d go about doing the research for the text and conversion process. 

Use this as your chance to build more trust. Let the client see that you understand what it takes to deliver quality work.

#6. Show Them a Sample That’s Relevant

I’ve hired a fair amount of freelance writers on Upwork. 

The easiest hires are the ones that share a portfolio sample that’s highly relevant to the type of work I’m looking for. 

In other words, if I’m hiring writers for this blog, I want to see examples of financial writing, not some random college paper on a different topic. 

In fact, here’s a good rule of thumb when it comes to what to put in your proposal: Send the prospective client one relevant sample (or two samples at the most) of your work that’s closely related to what they’re looking for.

As a freelance designer on Upwork, I always included one landing page in my proposal that was as close as possible to what the client was looking for — often asking them, “Am I correct that this is the type of landing page you’re seeking?”

This was also a great form of social proof, as the prospective client saw I had previously worked with XYZ Company.

Now, let’s say you’re brand new to your niche and you don’t yet have a sample of client work. 

In this case, create a sample and even let your potential client know that this wasn’t paid work, but that you took the initiative to create it to display your skill in this space. 

For example, if you’re a freelance writer, write at least one sample piece that you can send to clients. This is where it helps to have a niche, so the same sample can be used in all your proposals. 

Here’s a detailed guide on how to create a freelance proposal from scratch.

#7. Satisfy Your Client at All Costs

It’s really hard to overcome a bad piece of feedback early in your Upwork career. If your first feedback is less than five stars, you may never land another client. 

In addition to working for less than you’re worth, you need to make sure you’re putting everything you have into delivering a top-notch product. 

So, don’t just deliver your work on-time — deliver amazing work that will “wow” your client.

If an Upwork client asks for revisions or re-work, just do it: the cost of getting a negative review will be much higher than the cost of the time spent in revision.

Even consider giving something a little extra that they didn’t expect. 

As an example, say you’re a graphic designer; you could offer two or three choices for your client, in multiple file formats, even if they only paid for one. 

If you’re a freelance writer, one idea would be to run your work through an on-page SEO checklist, making comments in the article showing where you optimized it. 

Do something unexpected that shows you went a little above and beyond. 

Top 9 Mistakes New Freelancers Make When Applying for UpWork Jobs

We’ve talked about what to do, so next let’s talk about what not to do. 

From my experience hiring freelancers on the platform, here’s what’s going to quickly get your Upwork proposal dismissed. 

1. Neglecting your Upwork profile. A professional photo, a unique title and a quality professional description are table stakes to land a job on Upwork. 
2. Bidding too high. It’s OK to underbid a project when you’re new. Look at Upwork as a long-term game — you need a few jobs under your belt before you’ll be competitive for better gigs.
3. Only skimming the job description. Read the entire job description. It sounds obvious but many don’t bother to do it. 
4. Writing a novel-length proposal. I’ve seen 500-word proposals, which (in most situations) is absurd. No potential client will read this much text. Keep it concise and focus on starting a conversation. 
5. Rushing through the “additional questions.” When you submit a proposal, these questions appear below the cover letter. But when a client reviews your proposal, they actually come before the cover letter. As such, your answers to these are the client’s first impression of you. But many people rush through them, thinking they’re ancillary to the cover letter.
6. Not sending relevant work samples in your job proposal. Sharing samples of your work is a great way to establish trust. So make it easy for your client to see your work by sharing an example in your application, and make sure you specifically discuss how it connects to the job they’re hiring for (i.e., don’t just attach it).
7. Sending too many work samples. Send the client one, or at the most two, very relevant work samples you hand-picked for them. A client doesn’t want to review dozens of samples. Just send in your best and most relevant. 
8. Not offering a delivery timeline. Say specifically when you can deliver the project — don’t leave it up for the client to suggest a timeline. This makes it much easier for the client to say “yes.”
9. Submitting proposals with grammar mistakes and typos. Read through your job proposal out loud before hitting send. Clients are looking for attention to details, and the easiest way to display the opposite is with grammar mistakes.

See also: How to write a great Upwork proposal.

Frequently Asked Questions About Getting Started on Upwork

Upwork Tips: Summary 

On The Ways To Wealth, we often talk about how making money is a skill that anyone who practices can learn over time — and therefore, increase their income. 

You’ll be glad to know that Upwork is one of the best environments for learning how to make money that exists today. 

As an Upwork freelancer you can:

• Test different approaches to landing a job, looking for what works and what doesn’t.
• Find out which of your skills has value in the marketplace today — and, just as important, which skills you need to acquire to make more money in the future. 
• Take on projects that stretch your current skills and abilities.

It’s this fast-paced, real-world experience that’s going to allow you to not only become better at making money, but also have the bank account to prove it. 

If you’re looking for more reading material, check out these new freelancer resources we’ve put together: 

• How to get your first job on Upwork
• How to apply for writing jobs on Upwork
• How to write great freelance proposals
• How to create a portfolio from scratch as a new freelancer

R.J. Weiss

R.J. Weiss, founder of The Ways To Wealth, has been a CERTIFIED FINANCIAL PLANNER™ since 2010. Holding a B.A. in finance and having completed the CFP® certification curriculum at The American College, R.J. combines formal education with a deep commitment to providing unbiased financial insights. Recognized as a trusted authority in the financial realm, his expertise is highlighted in major publications like Business Insider, New York Times, and Forbes.