Matt’s Step-by-Step Guide to How I Made Over $100,000 Freelance Writing on Upwork (and How You Can, Too…Maybe!)

The advent of the Internet changed the way people work, but many of us never realized just how drastic those changes could be. The COVID pandemic woke a lot of workers and employees up to the possibilities, and now the “gig economy” is hotter than ever. People are increasingly staying home and trying to convert their freelancing side hustles into viable standalone careers. 

I’m one of those people and I’m here to tell you it is possible, if you have skills that can be used remotely…and if you work hard to build up your online reputation. 

I know it is possible because I’ve earned over $100,000 on Upwork, by myself, with no training or help. And I only use Upwork part-time, a few hours a day, Mon-Fri. 

Matt on Upwork

Here’s a direct link to my Upwork profile if you want to check it out live…

Okay, here’s how I’ve made money on Upwork and how you can, too. Please read carefully…

Adjust Your Philosophy: 

In America, there are restaurants called ‘buffet style’ restaurants. At these, all the food is already prepared and is sitting out on countertops. 

There are no menus. There are no waiters. Nobody helps you; you have to get up and go get what you want…before someone else gets it. 

Upwork is a buffet style work platform. 

The food (i.e., the work = the money) is there. But you have to get up and get it…before someone else does. 

Nobody will do it for you. It’s not easy; it takes time and patience and persistence. But the jobs are there, waiting. The more jobs you get, the easier it gets. 

The Upwork Customer:

You have to invest time to learn how Upwork works, and how to get more jobs. Let’s start with the customer. 

Upwork is the world’s largest freelance platform. Customers come, with money in their hands, to post jobs. 

Then they wait for you to apply, and then they make a decision about who to hire. 

You have to think like the customer. 

What are they looking for? 

How do they find you?

How do they decide who to hire? 

I want you to spend time thinking about these questions. Think like the customer thinks, so you can adjust your profile and your proposals. 

Now let’s talk about your profile and your proposal strategies…

How Upwork Customers Find and Hire You:

Customers find you one of three ways:

  1. The customer posts a job, then they look for qualified candidates to invite (no connects required)
  2. Upwork staff sees their job post and invites you to bid (no connects required)
  3. The customer posts a job, then you see it and you bid on that job (connects required)

Note, I got 99% of my Upwork jobs through #3. I find the jobs I want, and bid on them. 

Your Upwork Profile:

Your profile needs to be optimized by:

  • Using a heading that appeals to the customer
  • Includes relevant tags, so:
    • you will show up when they search for workers
    • you will be listed as the BEST MATCH worker when you apply*

*Upwork has an algorithm that it uses to ‘recommend’ Best Match applicants. So even if you are the most qualified, the potential client will never know if they don’t open your profile. Many only open the profiles of the recommended freelancer. 

You have to try to make your profile become a Best Match by using the right tags (note, Michael is a freelancer I’ve worked with before, and I recommend checking his profile out!). 

Your Upwork Profile Photo:

This is the first thing Upwork customers look at! It should not be important, but it is!

You should look the way you want them to view you, as a person they have to hire immediately! Confident, with a smile and a direct stare at the camera. Head up, a nice shirt or something, and some color to make the image stand out. 

Think about this — a customer might get 20 – 50 applicants to a job. The first thing they do is look at the photos of the Best Matches. So your photo has to get their attention. 

I’ve tried lots of different photos on my Upwork profile. So far, this one has been the most successful. 

Matt on Upwork

Your Upwork Rate:

To be honest, if an Upwork customer is looking for an English-speaking writer, for example, they will choose a native English speaker first. The only reason why they might not is to save money. That means, if you are a non-native English speaking writer, you will need to charge less than a native speaker. 

So what is a fair profile rate to ask?

That may depend on where you live. 

There is a term called geoarbitrage — to live in one economy but earn money from another economy, and then profit from the different currency values. 

If you’re in Turkey, the exchange rate is $1 = 8.77 TL. 

So if a worker lives in Turkey but writes for dollars, and they charge $10 an hour, they make 87.70 lira an hour. That is a good wage for a writer in Turkey. 

But is it too high? Would $8 an hour be better? Would that get more customers? 

If you’re in Pakistan, $1 = 157.88 rupees. According to PayScale, the average writer in Pakistan makes 500 Rs an hour, i.e. $3.16 an hour. 

So, if you are asking, say, $14 an hour that’s 2,210 Rs an hour. 4X the average that a writer in Pakistan makes! 

Yes, that would be a fast way to make money, but is that a fair rate? 

If you ask $8 an hour, that’s 1,263 Rs an hour…less than 3X the average, so that is closer to being acceptable. 

Will Upwork clients hire you at that rate…or are you eliminating yourself from consideration before you even get started? 

Find a rate that is fair to you and that the customer will pay. 

Again, if they are shopping for overseas talent, it is because they are trying to save money. It does not save them money if you are asking the same rate that a native speaker would. Your experience and education are factors to consider, so you may well deserve more than the average. But you have to prove it to the customer. 

If you are in the Philippines, the hourly rate for a writer is 247 pesos. The currency exchange is $1 = 48.54 pesos. 

So, if you charge $10 an hour, that’s 480 pesos an hour, about 2X the average. That is within an acceptable range, in my opinion. Again, experience and education are also factors to consider, so you may well deserve more than the average. 

You don’t want to go too low, but you have to be realistic. 

The minimum wage in America is $7.25 for some states. In California, the highest minimum wage is $14. Customers can find native speakers to write for $7.25 – $14 an hour, so your rate probably should not be more than $14 an hour unless you are very fluent, a very qualified writer, and have a lot of great client reviews on your profile. 

Remember, Upwork is “UP” work. 

The more you do, the more reviews you get, the more you can charge. 

You work your way up. So, you have to start with a lower rate and go up slowly over time. That’s how I did it. I started writing at about $0.02 per word, and now I charge at least $0.10 – $0.12 per word. As an hourly I charge at least $35, up to $45 or more. In some cases, my rate (for fixed price jobs) broke down to over $65 an hour.

Your Upwork Proposal Cover Letters and Bids: 

When an Upwork customer is reviewing applicant bids, they see your basic info first: 

  • your name, 
  • photo, 
  • where you are located, 
  • heading on your profile,
  • hourly rate you bid,
  • how much you’ve earned,
  • your Job Success Score (if you have one)

They’ll also see a line or two from your proposal cover letter, so that first line has to get their attention (see mine below)…

When I bid on an Upwork job, I do use a cover letter template that I have saved on Google Docs. But, I customize it a little bit for each job I apply to. 

I’m going to share my proposal template with you. It is long, and not every customer likes to see a long template. But, I do get a lot of positive feedback about it. 

My Upwork cover letter template (not my profile, because you cannot put links in your profile…but you can put links in your profile portfolio):

Hi, I’m Matt Cates, a Top Rated Plus content and copywriter with 250+ completed Upwork projects. I’m also a retired Air Force administrator with a Master of Fine Arts in Creative Writing. 

I’ve written for dozens of well-known companies around the world on projects related to website copywriting, inbound marketing content, lead magnets, branding solutions, and other specialized writing. If interested, my net typing speed is 71 wpm, based on a benchmark test. 

Clients and employers include:

  • Universities (dot) com, Gladeo, Chegg, Monster Education, Pearl Tutoring (popular education & career sites)
  • China Light & Power (a member of the Global Dow)
  • Rally Rd., a collectibles investment app now worth millions 
  • Forbes (see link in my work samples)
  • G.I. Jobs (a vertical of VIQTORY Media, with ~22 million military and Veteran readers)
  • Indeed (the highest-traffic job website in America)
  • Oregon State University (including the Office of the President)
  • U.S. Air Force (including as a Superintendent at HQ USAF, Pentagon)

I love working with small businesses and startups! I write fast, do thorough research, follow directions, and turn in high-quality work tailored to your needs and budget. 

My Job Success Score reflects my commitment to keeping customers satisfied. I invite you to review my testimonials and ask me any questions you’d like!

Warm Regards,

Matt Cates

http://www.MattCates.com

Work background:

  • 5 years as a digital content creator and copywriter (www.MattCates.com)
  • Ad hoc creative director for a pre-launch veteran apparel company 
  • Oregon State University’s College of Engineering (School of Electrical Engineering and Computer Science) and Office of the President (as an admin assistant, 2018-2019)
  • 21 years as a highly decorated Air Force Knowledge Operations Manager, 1994-2015 (retired 2015), including assignments at:
  • Headquarters USAF/A2 (Intelligence, Surveillance, and Reconnaissance). Pentagon (as an admin and superintendent, 2013-2015)
  • Oregon State University’s Dept of Aerospace Studies (as courtesy faculty providing career mentorship to students, 2009-2013)
  • Washington State, Hawaii, Turkey, England, Guam, South Dakota, and deployments to Afghanistan and Iraq

Education:

  • Master of Fine Arts, Creative Writing (3.84 GPA)
  • Bachelor of Science, History
  • CELTA – Certificate in English Language Teaching to Adults, via University of Cambridge and International Training Institute (Istanbul, Turkey)
  • Non-Commissioned Officer Academy & Senior NCOA DL Course 14 

Notable clients:

Blue Air, BuildMAX, Cambly, Chegg, China Light & Power, Coats Agri-Aloe, Crystal Cloud 9, Degree Prospects, D’Vine Grace Vineyards, HYPO by Eirtree, Everbeam, G.I.Jobs, Gladeo, Gulf Breeze Recovery, Herbaly, Indeed, Ivy League Prep Academy, Jerrick Media, Method Test Prep, Monster Education, Navitent, Professional Development Courses (University of La Verne), Rally Rd., Romeo Echo Real Estate, Senseon, Spirit Unto Spirit, Stand Ready, Syndicate Media, Timely Testing, TSP Pilot, Universities (dot) com, Work Social, and more! Other past work includes ghostwriting a popular English learning storybook and developmental editing for a bestselling children’s book.

Work samples:

[Here I just include names and links to articles I’ve done.]

NOTES:

> Upwork only reflects “hours worked” from my hourly contracts. Many of my contracts were fixed price.

Recent feedback:

“Matt is extremely talented and is very passionate about his work. We feel lucky to have connected with him and look forward to all of our future projects together! He asked the right questions, took the initiative to research our industry and was considerate about our budget. In addition, he responded very quickly and his turnaround time is lightning speed! Most importantly, the quality of his writing is outstanding. He took the time to get to know our brand and what we stand for – we truly appreciate the extra effort. Beyond 10/10 stellar service!!” 

(I’ll post a breakdown of all my cover letter elements soon…)

Upwork Customer Feedback and Reviews:

To succeed on Upwork, you have to do everything possible to earn a 5-star feedback from every customer, every time. 

Their feedback is as important as the money itself, because bad feedbacks mean you won’t get hired by anyone else. So no matter what, get a good feedback. 

What I do is I ask them before we close the contract — is there anything else I need to do to ensure a 5-star feedback? 

Ask them directly before closing. That way, you give yourself a chance to fix anything, and you put the pressure on them now. 

Now if there’s a problem, you gave them a chance to correct it, and if they don’t take that opportunity, they have no excuse to give less than a 5-star review. 

Every feedback should be great, but it is largely up to you to make that happen. Do not take a passive role in this. Be proactive, go above and beyond, no matter how big or small the job is. If you take care of your reputation first, then the money will take care of itself. 

If you put the customers’ needs before your own, they will come back for more. That does not mean to let them take advantage of you. Be a professional and demand their respect. But earn that respect. Treat them well but as an equal. After all, they are the ones asking for YOUR help! 

As one of my Upwork customers likes to say, he needs me more than I need him. And he is right. 

They need you but make them really depend on you and count on you. Make them love your work and they will return. 

Repeat customers are your best friend on Upwork. You want the same Upwork customers to keep coming back and this will save you time and energy (but you only want them to come back if they pay well!!). 

How to Select the Best Upwork Clients:

I get at least 2 invitations a day from potential clients, but I turn down 95% of them without doing an interview. 

I am very selective about who I work with, and you should be too!

Why? Because you want to have a fun experience and you also want the customer to be happy, so you’ll get a good feedback (and repeat business). 

So, don’t take an Upwork job unless you actually are interested in it AND are qualified to do it (or at least think you can be, with some research). 

I like to read the reviews that other freelancers leave on customer profiles. That’s right, it isn’t only the freelancers that get feedbacks; the clients do, too. And if they don’t have a 4.85 score or better, I read their reviews very closely to look for the problem. The freelancers will usually tell you about a bad experience. 

I also look at how much the clients have spent, BUT — many big spenders don’t pay very much per hour. So look at how much they pay on average, and scroll through some of the past jobs they’ve hired freelancers for. Check out what they’ve paid in the past. 

Also, I pay attention to their tone of voice in the job post. If it sounds like they are going to be super picky, I avoid them. If they are bossy sounding, I avoid them. I’m here to make money but also to have a good time. I select my clients carefully and enjoy working with them. I’m looking for repeat business and long-term relationships. 

To date, I’ve only had a handful of what I would consider less than optimal clients. The vast majority have been awesome, and that is not by coincidence. It’s from carefully vetting them just as much as they’re vetting me. In fact, if the client lists the name of their business in their post, or in their profile, go ahead and look that business up online. Do some homework on them. This can help you ensure you are a good match, and if you bid and they open an interview, you’ll already know a bit about what they do.

Clients love to see initiative like that, in my experience. Of course, that doesn’t mean to go cyber-stalking them. And never ping a potential client on LinkedIn…that is not only against Upwork’s terms of service, but clients simply do not appreciate it. I’ve never done it, but have worked with enough folks to hear their Upwork complaints, and that one has come up a few times…

Okay, folks, that’s all for now! If you liked this article, please give it a thumbs up and share with your friends!

Published by Matt Cates

Retired USAF Veteran. Freelance writer. Author of 'Haveck: The First Transhuman.'

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