How I make $200k/year freelancing, my 10 tips for Upwork success

How I make $200k/year freelancing, my 10 tips for Upwork success

By Morgan Overholt

If you happened to read one of my Business Insider Prime articles about how I quit my “normal” job two and a half years ago and now make $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. 

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

In fact, this week, after a little over two years on the Upwork platform, I hit the coveted $200k mark – with $140k earned in just the last 12 months from that single revenue stream. (See revenue charts below).

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.

Upwork lifetime earnings = $200k Upwork 12 month earnings = $140k

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”. 

MORE: Read “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 everyday 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.

MORE: Read “How to write the perfect Upwork proposal, 11 tips on how to land your first job (with examples!)”

2. Build a website.

Having a website in 2019, 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. 

Splurge on an easy-to-remember domain name. I’m a big fan of just using your name – something like instead of Cheesy firm names are a dime a dozen. Just keep it simple and professional. 

If you’re on a budget, use a site like Weebly, Wix or Squarespace

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 5-10 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. 

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.

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).

My First 3 Upwork Jobs

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 but poignant. 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.) And most importantly…
  • A call to action (ie. 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.” Women are the biggest offenders of using phrases that suggest a lack of confidence. 

MORE: Read “How to write the perfect Upwork proposal, 11 tips on how to land your first job (with examples!)”

6. Quit worrying about fees, start worrying about ROI. Freelancing is a business.

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 $20k in fees over the course of a little over 2 years on Upwork, and a $20,000 expense on $200,000 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 $10k 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%.  

Upwork earnings vs fee

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

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. 

7. Treat your clients like GOLD

One of the biggest secrets to my success is how I treat my clients. I see my clients like I see myself – I see them 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 prevents 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 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 quick, and focusing on long-term, ongoing work.

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 and have been steadily increasing ever since. 

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

Increasing your upwork rate

Eventually you’ll want to turn your focus away from “1-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. 

Long term upwork contracts

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. Persistence is key.

The biggest factor that I can contribute to my success as a freelancer is the chip on my shoulder from years of office politics in the corporate arena. I worked myself to death 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.