Can you make good money on Upwork? How I made $500,000 in 4 years

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If you happened to read one of my Business Insider Prime articles about how I quit my “normal” job 4 years ago (in 2017) and now make almost $200k a year as a freelancer, you might be wondering exactly HOW I pulled off such a feat in such a short period of time.

Half of my freelance work comes from contracts I’ve procured on my own, mostly by word of mouth, and the other half comes from a website called Upwork.

Editor’s Note/Update: I now also run two blogs. The largest blog was launched in 2020. But for the sake of this article, we will focus solely on freelance revenue.

Read Also: Is it worth it to start a blog? How we made $100k in less than 2 years

So here’s the question: Can you make good money on Upwork?

I’m here to tell you, the answer is: 100% yes!

In fact, after almost four years on the Upwork platform, I’ve made over $500,000 on the platform. That’s an average of $120,000 per year.

I should note, before I dive into my love for Upwork, that I am not a paid Upwork spokesperson. I do not work for the company – I am just a freelancer who uses their service and wants to help others experience the kind of success and freedom that the freelance lifestyle has brought me.

Also, for the sake of transparency, I wanted to add that I make a bit of income from blogging and coaching. However, freelance remains my primary source of income.

And so, in this article, I thought I’d share my story, as well as a few tips and tricks on how I found my own little piece of “Upwork Success”.

If you haven’t already done so, you might also want to subscribe to my newsletter. In return, I will send you my Upwork jumpstart kit complete with a 28-day Upwork challenge (free for email subscribers).

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Read Also: “Morgan’s Salary Story from Refinery29

1. Fill out your profile completely. No skimping

This one seems obvious, but I still see newbies on the platform every day with a nearly empty portfolio and no listed work experience. Your profile is your digital resume, and you only get one chance to make a first impression with a potential client.

And if you don’t already have a professional headshot – spring for one. Generally, you’re only going to be out of pocket for less than $100, and it’s a sure-fire way to stand out in the crowd.

Read Also: How to write an Upwork proposal: 11 proven tips with samples

2. Build a website

Having a website in 2021, especially if you’re presenting yourself as a tech or design professional, is an absolute MUST.

Clients often ask for more information or additional portfolio samples, and having that website locked and loaded for their viewing pleasure is a contract-winning strategy.

If you’re on a budget, use a site like WeeblyWix or Squarespace.

Read Also: Best tools for freelancers 2022: 14 essential resources for your business

3. Apply for multiple jobs, every day

Applying for jobs on Upwork isn’t that dissimilar to applying for jobs in the “real world” – it takes time and persistence.

In the beginning, I applied for at least 2-3 jobs per day, every day, consistently. I submitted proposals for both small fixed-rate jobs and large contracts alike.

It took nearly 2 weeks to win my first gig, and it was for a $10 fixed-rate vector tweak. It took me 20 minutes from start to finish. The $10 didn’t matter nearly as much as that first review. It only takes a spark to light a fire.

Read Also: How I got my first job on Upwork: Tips (and examples) from a $500k freelancer

Speaking of reviews, don’t be afraid to ask your clients for a review at the end of each successful engagement. The first review is the most important. Do everything you can to make sure it’s a good one.

4. Don’t be picky (in the beginning)

While I’ve seen it happen, it’s unlikely that you’ll secure a $50,000 job right off the bat. When I was first starting out on Upwork, I mostly applied for a lot of cheap fixed-rate projects that I knew I could complete quickly. Consider it the cost of doing business.

When I joined Upwork, I was actively earning $75/hour on outside contracts on my own. But I didn’t let my pride get in the way.

My first three jobs included a $10 fixed-rate, a $20 fixed-rate and a $20/hour 2-hour gig. And each resulted in a great review which bolstered my profile.

Remember, you can scale up quickly as steady work begins to trickle in and you have those first few reviews under your belt (more on that later).

5. Learn how to write a proposal that sells

Part of being a successful freelancer is learning how to become a good salesperson. Presenting yourself as a knowledgeable professional who understands the needs of your client is crucial when it comes to winning contracts.

Make your cover letters short and sweet, poignant and client-focused. Aim for 200 words or less. No one wants to read a novel.

Make sure each cover letter contains the following components:

  • Your professional qualifications and related experience
  • Acknowledgement of the job requirements
  • A unique selling point (what makes YOU right for this job)
  • Related portfolio samples
  • A link to your website for more information and/or a link to your Upwork bio. (Pro Tip: As silly as this might sound, on the client side of the interface, multiple clicks are required to see a freelancer’s full bio, so many clients never bother)
  • A call to action (e.g. reach out to me today and we can discuss details)

And finally, consider the following phrases officially banned from your vocabulary: “I think, I feel, I believe, I should be able to” and instead use phrases like “I will” and “I am.”

Emotive phrases suggest a lack of confidence.

6. Quit worrying about fees, start worrying about ROI

From this point forward I want you to start thinking of yourself as a small business. And guess what, small businesses have operating expenses. The expenses aren’t what’s important. It’s the return on investment (ROI).

Yes, I’ve incurred about $50,000 in fees after nearly four years on Upwork, and a $50,000 expense on $500,000 is what I would call an excellent ROI. (That’s a 90% profit margin. Other industries would KILL for a 90% profit margin!)

I will make this concession: I think the Upwork fee structure can be confusing to newbies.

The thing that newbie freelancers don’t always realize about the “20% fee” – and admittedly I didn’t either when I first started – is that it only applies to new clients, on the first $500 earned. After that, it immediately drops to 10%. And at the $10,000 mark, it drops to just 5%.

The key to being successful on Upwork is creating long-term, ongoing relationships with clients which lessens the fees you pay. My average monthly fee is now 8%.

And I can assure you, now that I’m operating as a small design agency – I have WAY bigger expenses to worry about than my little 8% Upwork fee – like my 30% tax bill, for instance.

The following chart depicts my income vs expenses over the course of my first two years on the Upwork platform.

My Upwork Fees vs Other Business Expenses

And sure, you can find clients on your own without the help of Upwork. It can be done, and if you’re able to do so, go for it! But for most of us, pounding that pavement and making cold calls can be a lot of work that doesn’t always pay off.

Upwork represents the largest freelance marketplace in the world. It’s like fishing in a pond where you know the fish are biting. They also handle the contracts, payments and serve as that all too important intermediary should a dispute arise.

In my experience, I tend to spend more time chasing down off-site clients for payment than I do my Upwork clients. It’s helpful to have that middle-man in place to keep everyone accountable.

7. Treat your clients like gold

One of the biggest secrets to my success is how I treat my clients. I see my clients as I see myself, as business owners in need of a professional to make their lives a little easier.

I make myself as available as possible during the week, and always assure my clients that I’m just a phone call or text away should an emergency arise.

I use just about every messaging platform known to man to accommodate as many people as possible (Slack, Skype, Upwork messenger, etc). I respond to most messages within a matter of minutes. I reply to most emails within 24 hours.

I pay attention to detail as well. If I spot typos in my client’s source material, I correct them. I recommend various printers and advise on best practices. I even maintain an Adobe Stock subscription and allow my clients to use my account for no extra charge so we never have to worry about licenses or poor quality (my clients really tend to enjoy that little perk).

I offer a concierge-level service. I am not just a graphic designer. I am a problem solver, business advisor and friend.

8. Play by the rules

People love to break the rules, then complain when their accounts are shut down and have “no idea why”. Two of the most popular rules to break seem to be:

  1. Doing “free” work
  2. Taking clients off the site

Both of these actions prevent Upwork from making money. If Upwork doesn’t make money, Upwork doesn’t exist. Don’t bite the hand that feeds.

Besides, staying active on Upwork is a much better long-term strategy than getting a couple of jobs and then rushing to take your clients off the platform to avoid fees (you know who you are).

Over time, my visibility on Upwork reached such a peak that I no longer even have time to apply for jobs and receive so many invites on a daily basis that I turn down more work than I accept.

9. Focus on growth, scale and long-term contracts

After you get those first couple of jobs under your belt, the key to Upwork success is scaling up quickly, and focusing on long-term, ongoing work.

In my first week on Upwork, I charged $20/hour out of sheer desperation to get hired but started raising that rate immediately following those first few engagements. I have been steadily increasing ever since.

I’ve always calculated my rate in correlation with the amount of work coming in and scaled accordingly.

Eventually, you’ll want to turn your focus away from “one-off” little jobs and on to long-term projects and ongoing work. Over 75% of my work today comes from ongoing contracts and relationships. Ongoing work is beneficial because you’ll spend less time hunting for jobs and more time working.

Also, the Upwork fee for jobs over $10,000 is only 5%, which means the more ongoing contracts you’re workin’ on – the lower your overall average fee will become. Cha-ching!

10. Adopt a “failure is not an option” mindset

The biggest factor that I can attribute to my success as a freelancer is the chip on my shoulder from years of office politics in the corporate arena. I worked myself tirelessly only to be told I was “too aggressive, too ambitious and too impatient” on a regular basis.

I would have done anything to avoid going back to that life.

Remember, you won’t become a six-figure freelancer overnight. Nothing worth having in life comes easy.

It would have been all too easy for me to throw in the towel when I didn’t win a single job during my first week. But I made it my mission to build a stellar Upwork reputation and make freelancing a full-time career – and it paid off.

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What are your favorite Upwork tips? Let me know in the comments. Also, don’t forget to connect with me on social media using the links below.

32 thoughts on “Can you make good money on Upwork? How I made $500,000 in 4 years”

  1. Wow, Morgan, this is exceptional writing. I will print this and use it as a reference. Found a lot of things I could improve on, especially in the “swallowing my pride in the beginning part”. One of the most important parts of all this is “treating your clients like gold”. Nothing does word-of-mouth magic like this does.

    Quick one though, what tools do you recommend for automating administrative jobs? Accounting, work timing, CRM?

  2. Amazing article Morgan! Thank you for all the great tips! I am also a freelancer on Upwork and working on building my business. It is always a pleasure to see and read about another freelancer who has had success working with Upwork.
    I wish you continued success and again, thank you!

  3. Wonderful! Some of my favorite tools: (Slack for communication, And.Co for Logging/Invoicing/CRM, and I currently pay an accounting firm in town to help with my taxes.

  4. Wow! Thanks Morgan ! Having Fiverr background, moving to Upwork felt nightmare in terms getting jobs and proactive nature of upwork. Struggled a bit here. Your article made me feel the areas I was not ticking. This provided me with whole new spirit of motivation and excitement !

  5. There really is no “normal” when it comes to Freelancing – everyone’s experience is unique. Are you freelancing full time? Are you applying for jobs every day?

  6. Wow!
    This is such an insightful and encouraging piece. I particularly loved the way you included your real life story and narrated how you rose to success. One lesson I’ve learnt is that it’s never gonna be easy but it’ll pay off in the end
    I’m also a freelancer on upwork and I wish you well
    Thank you!

  7. Dear Morgan,
    have landed your profile and this site as result of google researc h on how to set up and provide freelance services. Happy to find this article and find it very helpful to develop understanding. Appreciate you take time to share wisdom in a succinct manner and good structure.

  8. Really love your article. Hope so it will be helpfull for my future portfolio. Right now i strated chnaging in my portfolio.

  9. Great! Great! Great!
    You are really great!
    I was working on Upwork for 2 years and yesterday my account was blocked.
    I am not sure why.
    I am going to create a new account again.
    I will follow your article.
    Thanks for your wonderful article.

  10. Hi I know this is pretty late but I always wanted to be a software engineer and I now have all the tools I need to learn and succeed but I’m 13 is that going to change anything when I want to become a freelancer

  11. Astonishing write-up Morgan and it’s insightful. I’d signed up on Upwork for the past three months and got nothing.

    Now, reading this reveals the changes I have to make, like applying for 5 to 10 jobs daily with consistency. Review my fee to enable me to accommodate clients, have a website, and portfolio.

    I appreciate learning from successful freelancers.

    Thank you.

  12. Thank you so much! I love how transparent you are. I’ve been a designer for 10 years but that doesn’t mean anything to someone who doesn’t know me or what I’m capable of. I’m going to give Upwork another shot and this time 1) swallow my pride and lower my rate in the beginning. And 2) be persistent!

  13. Just an update: I got the first gig I applied for using the tips in the article! About to go work on it now, just wanted to drop by first and say THANKS!

  14. Hey Morgan,

    That’s such a fantastic streak of success on Upwork (although I don’t agree with the “don’t be choosy” part (because I am like that) 🙂

    This blog is needed on so many levels, for so many people, right? It’s easy to keep picking on things like “no clients”, or “Upwork is expensive” or whatever. It takes a tremendous level of motivation, focus, and effort to get here.

    I like this so much that I think my new blog post on freelancing might just need this. I am going to mention you (will publish tomorrow) and send you a Tweet 🙂


  15. Wow very motivational story for me till now I just earned 900$ on UpWork and struggling to find new clients np long term client right now even my all reviews are 5 🌟 but you’re story motivates me now I’ll try work more hard to become a successful freelancer like you Thanks🙂

  16. Great article, Morgan! You are a huge inspiration! I am desperately searching for my purpose in life – my “niche.” That’s why I recently joined Upwork this past August. I am hopeful! I hope to be in your shoes one day! Best of luck to you!

  17. Woow! This is soo inciteful. I almost gave up on Upwork but reading this has given me so much motivation. I’m glad to have stumbled on this wonderful, motivating piece.

    I look forward to using the knowledge on growing my career on the platform. I’m a fulltime freelancer and it surely does require a lot of motivation and less giving up!

    Thank you Morgan!

  18. Very helpful article. Recently i got “Top Rated” Badge. Now i am trying to select a niche to get more focused work. Could you please give me your advice on how to get top paying clients.

    Thanks Morgan.

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