Make Money

How I Became a Highly-Paid Freelance Writer on Upwork

Some of the links on our website are sponsored, and we may earn money when you make a purchase or sign-up after clicking. Learn more about how we make money.

Whether you’re looking to kick off a full-time freelance writing career or just make a few bucks writing articles on the side, Upwork can take you there. 

Upwork is one of the best ways to gain access to a steady stream of freelance writing jobs — even if you don’t have any writing experience or connections in the industry. 

We covered many of the basics in our guide to getting your first job on Upwork, so in this article we’ll focus exclusively on using the site to find good-paying freelance writing opportunities. 

We’ve also compiled a suite of resources that are helpful for beginning freelance writers, which you can find at the end of the post (or you can jump directly to that section).

Read through this material in its entirety and you’ll learn…

  • How to find freelance writing jobs on Upwork.
  • How to choose the right jobs to apply for.
  • How to carve out a niche for yourself.
  • How to identify what Upwork clients actually want.
  • How to craft winning proposals.

And you’ll know exactly how to get your first client. 

Much of what’s covered below is based on my own first-hand experience applying for Upwork writing jobs.

My Experience

Everyone’s freelance writing journey is different, but few are linear. So while your experience may be a bit different than mine, from what I’ve seen, my zero-to-writer story is pretty typical.

How I Became a Freelance Writer

Prior to registering with Upwork, I’d never had a paid writing job

The closest job I’d had to a writer was an 18-month stint as an in-house editor at a research firm where we published reports on healthcare technology.

I got that gig almost by accident. Instead of firing me for being a terrible secretary, the kind executive team gave me a second chance in the editing department. Unfortunately, more than half of that 18-month stint was part-time, so I eventually had to look for another opportunity.

Prior to that role, a good portion of my editing portfolio was comprised of pro bono pieces — things like sprucing up resumes, revising personal memoirs or editing medical school cover letters as favors for friends and family members. 

I tried to land other full-time editing and writing jobs, but because I had no formal education in those subjects and a limited resume, I was turned down for every single one of them. 

So in an act of desperation to get out of a dead-end job working the night shift at a local motel, I decided to give freelance writing on Upwork shot. 

Getting My First Contract 

Getting my first contract for a writing job was far and away the hardest part of my freelancing career. 

Convincing myself that I was a good enough writer and editor to make it as a freelancer, when I’d been turned down many times before, was tough. 

On days when impostor syndrome made me think I was crazy for trying to start a freelance writing career, I told myself, “I can’t be the worst writer out there. If others can do this, then why not me?” 

It took me a month and several proposals to get my first gig on Upwork. 

Even after I got that first five-star review, subsequent jobs were slow in coming. In the beginning, I was getting replies to one out of every 10 or 15 proposals I sent — and only about half of those clients actually hired me. 

But as I got more jobs and more good reviews, gigs became easier to land.

I got a better feel for which jobs I was qualified for and which ones were over my head or outside my wheelhouse. 

Plus, I learned not to waste my time on jobs that already had dozens of applicants, and to focus my efforts on assignments I could complete quickly and confidently.

Pro Tip: Search for terms like “new to Upwork,” “24 hours,” or “urgent” in the search bar. Some clients don’t mind working with newbies and will state that in the text of the job post (hoping to get the work at below market rates). Others are looking for a quick turnaround and are less-than-picky about who does the work. These posts are great finds for landing a first gig.

Building a Niched Portfolio 

I knew from the start that I wanted to niche down and write personal finance articles.

My husband and I had managed to get out of debt and cash-flowed a master’s degree — all with three kids, a single sub-average income and a few side hustles. 

This experience planted a passion in me for personal finance. It was because of the knowledge I acquired from books, blogs and podcasts that my family made it through that lean period. So I wanted to help spread the knowledge I’d gained to others through my writing.

A few Google searches (and a vague sense of Dave Ramsey’s net worth) confirmed that the personal finance niche had plenty of clients with deep enough pockets to pay for blog writers.

In the first few months, I had to take whatever work I could get. But I applied to as many personal-finance-related gigs as I could. 

I had started my own personal finance blog (even though nobody read it at the time), so I included articles I had written on personal finance in my proposals. 

Incidentally, no one seemed to care that I hadn’t been paid to write those articles.

I also focused on related “next door” niches to personal finance, like real estate, entrepreneurship and technology. Not only did these force me to hone my research skills and broaden my knowledge base, they also kept things interesting by changing up the subject matter of my writing from time to time.

After a year of curating a personal-finance-centered portfolio, I started receiving invites to apply for jobs writing personal finance articles — more than I could comfortably handle.

I now have the luxury of only taking on jobs that are inside my niche or interesting enough to stretch beyond it.

Related reading: How to find your ideal freelancing niche

Raising My Rates 

Raising your rates is scary, since you are the only one justifying your worth to the client (who understandably wants to pay as little for your services as possible). 

I’m a frugal person by nature, so raising my rates cut against the grain for me. I want to pay the least amount I can for things, so I assume others do too. I feared that clients would see my higher rates as greedy or presumptuous.

What’s more, early on I had a client that decided to stop working with me, stating that I was charging too much for my articles — even though I hadn’t changed my rates since we initially started working together. 

That terrified me, because at the time it was my steadiest and highest-paying client. That conversation kept me working for a lower rate for longer than I probably should have.

But no client lasts forever. 

As clients turned over and I pursued new ones, I eventually got gutsy and bid for higher rates, just to see what would happen. I was surprised how quickly I inched my per-hour and per-word rate up. 

In less than a year, I replaced the part-time income I was making at the motel and was able to work whenever and wherever I wanted. 

I’m no longer afraid to pass on a job if the rate is too low, as I have learned to value my own time and expertise — which turned out to be worth much more than my canceling client was willing to pay. 

But keep this important point in mind: to get there, I had to be willing to start low. If you have no experience and a limited portfolio, you’re more than likely going to have to take a handful of jobs that pay less than you’re worth.

Just don’t fall into the trap of feeling like you need to keep working at those rates forever.

Five Things You Need

Getting started as a freelance writer is truly the hardest part of your career. And while starting is difficult, it isn’t complicated. 

Here’s a list of the basics you need before you’re ready to hang up your shingle. 

#1. A published writing sample under your own name (in any topic)

Published articles with your byline give you a lot of credibility as a writer. 

Even if what you’ve written is completely unrelated to the job post, published writing carries far more weight than a random Word document attached to your proposal (which the client doesn’t even know for sure that you wrote).

Plus, they serve as a legitimizing factor: if you’ve been published elsewhere, the client is more likely to see you as an established writer — and they’ll feel safer entrusting their project to you.

You can still get freelance jobs without having any published work, so if you’re brand new to writing, don’t despair. But if you have anything published already, it will give you a leg up. 

This is why many freelancers have their own blogs; they serve as a professional credential. 

If you don’t think starting a blog is right for you, it’s absolutely worthwhile to find a couple of blogs or websites that will publish your article (with a byline), even if they don’t pay you for it. And it’s especially helpful if they’re in the niche you want to target as a freelancer.

#2. A writing sample (published or unpublished) related to the job you’re applying for

The first question on a client’s mind is: “Can this person produce the type and quality of work I need?” 

By showing them you’ve done something similar in the past, you answer that question for them.

This is important, because getting the job isn’t always just about your writing skill. Every niche has its own vocabulary and nuances, and clients prefer to hire people who can write with clarity and authority about their particular topic.

The sample doesn’t have to be identical to the job post, but it should have a similar style, tone, content and/or format of the work the client is looking for — and it should be in the same niche if at all possible.

Be sure to point out the similarities in your cover letter, as clients get a lot of applications and tend to only skim samples. 

#3. A complete Upwork profile

Paint a picture of who you are and establish your brand by fully completing your Upwork profile. 

Part of this means uploading a nice headshot. It doesn’t have to be a professional photo, but it shouldn’t be a social media selfie either. 

Digital first impressions are important, so read through this Upwork guide that runs down a few tips for choosing an effective profile photo.

Be sure to fill out your work history and upload some samples — the more, the better. 

Remember, your goal here is to instill confidence that you’re a professional who can get the job done. Most of the time, the client isn’t going to comb over your profile and samples — but if they click through and see that your portfolio looks empty, or if it seems like you haven’t paid much attention to it, that can be a red flag. 

Upwork also says that adding an introductory video to your profile can help you win more contracts

The video below goes into more detail about why your Upwork profile is so important, and outlines four tips for winning more contracts as a beginner on the platform.

#4. A complete LinkedIn profile

Once you apply for a job, the client can see your last name. As part of their due diligence, clients often search for you on LinkedIn. This tells them a lot about you, and it can be another chance to sell yourself and your skills. 

On the other hand, an incomplete or unprofessional profile can be an instant turn-off. So it’s important to take the time to fill out the profile as completely as possible, including a good headshot and a full work history. 

However, it’s even more important to make sure that your profile focuses on the fact that you’re a writer.

You’ve probably heard the saying, “dress for the job you want, not the job you have.” The same concept is true for online profiles and marketing yourself as a freelancer: you want potential clients to see you in the role they’re hiring for.

That doesn’t mean hiding from your past work history. Clients value all kinds of real-world experience — whether it’s working as an engineer or working the night shift at a hotel. 

Often, your professional experience gives you valuable insight into a specific field or niche that can help you win more clients and charge higher rates. 

For instance, a six-month stint in tech support and my year as a medical transcriptionist gave me just enough knowledge and exposure to the technology and healthcare industries to write about them, even though neither job had to do with writing.

So don’t hide your prior experience, even if you see them as less than ideal. But do tweak the language of your profile so that it frames you as a writer first and everything else second.

#5. Persistence

Breaking into this space takes time, patience and an unwillingness to quit.

So if it takes a while to get things going, remember that it’s normal for business to be slow in the beginning. Keep at it.

Even after your business gets rolling, you need to persist in learning and refining your craft if you want to stay competitive. 

So ask your clients for feedback and implement it. 

Five Steps for Writing a Good Upwork Proposal

Writing proposals takes a lot of time and effort — especially in the beginning, when your acceptance rate is low. 

But each proposal is an opportunity to introduce yourself, sell your skills and convince your client you can do the job. 

While it can be good to cast a wide net to get jobs, quality proposals will be more effective than sheer quantity. Treat each proposal as a one-sided job interview — that’s exactly what it is.

If you have no idea of what to put in your proposal, read on. The steps below will transform your proposals from forgettable to incredible.

Good Upwork Proposals Always Have…

  • A custom cover letter.
  • Links to relevant work samples.
  • Error-free writing.
  • A proposed rate or budget.
  • A proposed deadline.
  • An actionable next step.

Need more ideas to spruce up your proposals? Check out the additional suggestions in our comprehensive guide to landing your first job on Upwork.

Let’s dig into how to cover those bases.

Step #1: Research the Topic

If you don’t know a ton about the writing topic or industry of a job, at least take 10 minutes to Google some basic information. 

Often, this small amount of research will give you enough context to talk about the client’s project and get the ball rolling — and it’s more effort than 99% of applicants will expend.

Also, if the job post includes a link to a website, read that page to familiarize yourself with your potential client. 

Even without a link, you can sometimes figure out who they are by reading through their feedback or job posting history. A few minutes of sleuthing can sometimes give you enough information to deduce who you’re pitching to.

This is low-hanging fruit, but as I said earlier: many freelancers don’t even bother.

Step #2: Write a Custom Cover Letter

Of all the things in this article, this is the most important: customize every single cover letter every single time. No exceptions.

You can have a general template with paragraphs you cut and paste, but spend the time to tailor your references to the job post and the deliverables the client is asking for. (This is why it’s helpful if you can figure out exactly who the client is.)

Your cover letter is your one and only chance to showcase your skills and experience, and to explain why you’re the perfect freelancer for the job.

Subtly highlight the research you did in Step #1, and relate it to your past work or experience, if possible.

Here’s an example: 

“I’ve looked over your website,, and I noticed you always provide actionable steps the reader can take to identify the best possible use of travel points. I’ve done similar work when writing about cash-back shopping sites, where rates vary from site to site daily. Here are a couple of examples.” 

As I said earlier, the work doesn’t have to be identical to what the client needs, as long it demonstrates that you understand how to get this job done.

If you’re familiar with the job’s industry, drop enough lingo or references to convince the client of your expertise.

This strategy is especially helpful for specialized sectors like healthcare, automotive and technology. 

Pro Tip: Many job posts include a random word like banana, Bambi or paprika that you need to repeat in your cover letter to show that you read the whole post and can follow instructions (and yes, these are real examples). Pay close attention to these, as clients use them to weed out generic cover letters from their stack of submissions.  

Step #3: Highlight Your Writing Samples

Just like you, your writing samples need an introduction. 

Don’t just attach the files and call it done. Briefly explain the objective, tone and target audience of each piece, as well as the relevance to the client’s project.

Use this as an opportunity to talk about your processes. Did you conduct original research for the article? Was it heavily edited, or published as-is? Were you an editor, ghostwriter or the sole author? 

Give your client some context to paint a clear picture of your capabilities.

Step #4: Proofread Your Proposal

Cover letters or writing samples with typos and grammatical mistakes are automatic rejections for many clients. 

If you aren’t getting the interest you want, double-check your copy for errors. When your clients point out your errors, it’s horribly embarrassing (and yes, I say that from experience). 

Don’t be lazy. With the advent of spell-checking tools and Grammarly, professional writers have no excuse for delivering sloppy copy to clients. 

If you can’t be bothered to deliver a perfect proposal, your clients don’t have any reason to believe your writing will look any better.

And remember, this isn’t just a matter of them being curmudgeonly about grammar: the more editing your work needs, the more time they (or their editor or proofreader) will have to spend going over it prior to publication. And that costs money. 

Step #5: Suggest the Next Step

”Thanks for your consideration; I hope to hear from you soon” is not the next step. 

Instead of leaving the ball in the client’s court, make it easy for them to follow up with you. 

For example, if the natural progression of the conversation would be a video chat to discuss the project, suggest that. 

“I’m free Tuesday and Thursday of next week between 9 and 11 a.m. EST. Can we schedule a video chat to discuss the project in more detail?” 

The idea is to make it as easy as possible for the client to say “yes” so that you can keep moving the ball down the field until you’ve won the contract. 

Don’t be afraid to follow up. Clients get distracted. They get sick. They go on vacation. Their computers die. So if a client expresses interest but doesn’t reply for a while, that doesn’t mean it’s a ‘no.’ 

Keep in mind that hiring you is only one of a million things on their to-do list. If a client goes radio silent, politely follow up in a week and see if they still need the work.

What Upwork Clients Want

You can become a much more competitive candidate simply by putting yourself in your client’s shoes. When you know what your clients want, it takes the guesswork out of what to say to convince them that you’re perfect for the job.

#1. Someone who will actually complete the work

Whoever said that 80% of life is just showing up was obviously a freelancer. 

It always shocks me how many clients have been ghosted by other freelancers. One of my clients had a freelancer abandon the work when it was ¾ completed! 

Complete the work on time and in full, and always let the client know that you’re open to criticism and to make changes after you submit your work. 

(Unsure if you can complete the work you agreed to? See #2, below.)

When your client knows she can rely on you, she’ll keep you in mind for future projects.

#2. Clear and honest communication

Can’t make the deadline and need an extension? Need clarification on something? Want to know if your stuff hit the mark? Just ask!

In my experience, most clients are very helpful and ready to answer your questions. They realize that things come up and are willing to cooperate and find solutions to problems. 

Make good use of Upwork’s messaging feature — it’s the best way to communicate with your clients.

#3. Someone who can do the job well

Don’t forget that most of the time, your client is hiring you without ever having seen or talked to you.

That’s quite the leap of faith, even for a small project! 

Do everything you can to assure your client that you’re competent in the skills you claim.

If you have industry-specific experience, state that loud and proud in your proposal. Drop names or lingo when appropriate so your client knows you’re qualified. 

Freelance Writing Resources

Here are links to some of the online freelancing resources we’ve put together, with a few comments about how you can use them to further your freelance writing career. 

Upwork Writing Jobs FAQ

How much should I charge when first starting out?

There isn’t one right answer for this, but no matter how new to Upwork you are, it should never be $0. (Working for free or just a good review is against Upwork’s policy.) 

Writing a pro bono article for a friend’s blog, or writing an unpaid article for a website in your niche to fill out your portfolio or get a byline, is acceptable. But do this outside of Upwork. Even trial articles — ones where a client tests your skills to see if you’re a good fit — should result in some small compensation. 

That said, when you’re looking for your very first gig, the amount you make should be less important than actually landing the job. Even if you only make $5, if you get a five-star review, higher-paying clients are more likely to hire you in the future. 

If you have industry experience, there’s no need to sell yourself short, however. A good way to check if your bid is reasonable is to scan the budgets of jobs you’d like to get. 

You can also get on Upwork as a client and search the profiles of other freelancers. Scan for those with similar experience to yours and see what they charge. 

Premium Upwork subscribers can see the bid range on individual jobs, which should also give you a good idea of what to charge.

What types of writing jobs pay the best on Upwork?

High-paying industries include technology, sales, business-to-business work and medical, but there are good-paying gigs in a variety of industries. 

Regardless of what sector pays the most for articles, you’ll maximize your earnings by creating a niche in an area you know well and can write about over and over. 

If you can become the go-to guy or gal in a particular area, you don’t have to appeal to a broad client base as your expertise becomes your selling point. 

For example, food blogs as a sector might not pay super well, but you can rest assured that the articles written for Emeril’s or Rachel Ray’s sites do.

If you don’t have expertise in a good-paying area, look for niches that border on ones you know. Take on articles that you know at least a little about, and practice researching to broaden your knowledge base.

What is the Upwork Project Catalog?

Upwork’s Project Catalog was introduced in 2021. It’s a marketplace for fixed-priced gigs that functions identically to Fiverr; freelancers post a fixed-price jobs that clients can order on demand. For example, as a writer you might offer “A 10,000 word article on any topic for $1,000.”

Final Thoughts: Getting Started Can Take Time, But Don’t Give Up!

Like all businesses, a freelance career is built over time.

Luckily, sites like Upwork provide a plethora of paid writing opportunities every day for the freelancers with the hustle and skill to seize them. 

Expect hurdles, a disappointing number of rejections, and lowball offers in the beginning. These growing pains are normal. 

But if you’re taking the time and effort to create well-written samples for your portfolio, craft stellar proposals that showcase your skills, and communicate clearly with clients, your freelance career will grow and provide you with a steady income. 

Financial Tips and Deals Every Friday

Join over 10,000 subscribers and stay ahead with personal finance insights, the best deals, and the best money-making opportunities every Friday.

Jenni Sisson
Jenni Sisson is a freelance writer and editor focused on personal finance, technology and entrepreneurship. She is a serial side hustler and the host of the Mama's Money Map podcast. Reach out via her website.

    1 Comment

    1. Hi Jenni, really great article and a well-advised how to get started as a freelancer writer.

      Just wanted to say thank you for this. 🙂

    Leave a reply

    Your email address will not be published. Required fields are marked *

    Read our comment policy.