This is How I Got My First Job on Upwork – From a $600k Freelancer

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A Top-Rated Upwork freelancer shares the exact strategy she used to get her first job on the platform

Editor’s Note: I recently attempted this exact strategy again on a small gig to see if it still worked in 2024. I was immediately hired for the gig. That’s a 100% success rate in my book.

Whether you are a new freelancer or just new to the Upwork platform, landing that first client on Upwork can feel like an insurmountable task. Trust me, we’ve all been there. But as someone who also struggled in the beginning, yet later went on to earn over $600,000, I can assure you that success is possible for both experienced freelancers and newbies alike.

Upwork is a great place to earn serious cash and create a meaningful professional network. You just have to know how to apply often, work the program and pitch yourself correctly to win that first job on the platform.

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Morgan Overholt Upwork
Morgan Overholt’s Upwork Profile

4 steps to winning your first job on Upwork

Step 1: Avoid this common profile mistake

The very first thing you should do – before you begin applying for jobs and pitching to potential clients – is perfect your Upwork profile. That includes uploading a professional profile photo, writing an informative bio, using keywords in your title, and providing plenty of work samples in your portfolio. If you haven’t already, it’s also a good idea to read my article on exactly how to set your profile up for success.

I cannot tell you how often I see freelancers hurry through this step thinking it doesn’t matter. I’m here to tell you it matters a lot. Upwork includes a snapshot of your profile with every proposal you send. Upwork also uses keywords from your profile, and portfolio, to determine “best matches” to recommend to the client – and the “best match” tag is a powerful endorsement.

Step 2: Look for jobs you can complete quickly

When I joined the Upwork platform back in 2017, I was already an experienced freelancer in the “real world”.  At the time, I was earning $75 per hour off-site. And I knew nothing about online freelance marketplaces other than the horror stories I had read about in other blog posts. Luckily, I don’t scare easily.

Instead, I began to apply real-world strategies to my newfound medium. And if there’s one constant when it comes to freelance, it’s this: Reputation is everything. So when I saw that digital tumbleweed rolling across my profile where the positive reviews were supposed to be, I knew I’d have to remedy that problem as quickly as I could.

And so, I made it my singular mission to secure my first 5-star Upwork review. I applied for big jobs, small jobs, flat-rate jobs, hourly jobs, and even low-budget jobs. And I tried not to worry too much about making money on that first project. I just needed a job that was at least a good fit for my skill set and could be completed quickly so I could get that first good review on the board.

My real-world experience taught me that once I had established a reputation, winning larger contracts would be easier going forward. I knew I could ask for any hourly rate I wanted once I could afford to be picky. Until then, as my momma would say: “Beggars can’t be choosers”.

Step 3: Apply for multiple jobs everyday

Far too many people treat Upwork like they do a flimsy New Year’s resolution to start going to the gym and eating better. They do it for a few days, decide it’s too hard, and give up. The only difference is, that when people fall off the gym wagon, they don’t blame the gym.

Building a reputation on Upwork takes time. I applied for 2-3 jobs nearly every day for nearly two weeks straight. Below is a list of actual job titles I applied for – with my proposed terms and rates – during those first few days on the platform.

  1. Graphic Designer for company branding and ongoing work ($39/hour)
  2. Senior Logo Designer ($120 flat-rate)
  3. Facebook ad image designs needed ($39/hour)
  4. Looking for someone to design a mobile email template ($39/hour)
  5. Clean and modern dermatology invitation templates ($39/hour)
  6. Graphic designer for jewelry brand, long time job ($39/hour)
  7. Looking for someone to help enhance some graphics ($39/hour)
  8. Need a website designed, will have the main page with 4 subpages ($350 flat-rate)
  9. Convert HTML site to WordPress ($300 flat-rate)
  10. We need artists to design graphics for wine/spirit bottles ($39/hour)
  11. Redesign and format an assembly instructions sheet ($50 flat-rate)
  12. Looking for an all-star designer to help with branded worksheets ($39/hour)
  13. Logo Design – Need someone to redraw logo, make minor changes ($10 flat-rate)

It was lucky number 13 that finally produced the first nibble – a $10 logo vector tweak. It wasn’t exactly my dream job, and it wasn’t going to be a ton of money. But I knew I could knock the project out of the park. And I knew I could do it quickly.

first job on upwork
This was the job posting for my first Upwork contract

Step 4: Write an irresistible proposal, like this one

Finally, you’ll need to learn how to write an irresistible proposal. If you haven’t already done so, I highly recommend reading my article on proposal writing tips. This is the actual proposal I used to land my first job:

Hi! I am new to Upwork – but I am a 15 year veteran in the graphic design industry.

Because I am so new to this site – I am in need of a great review to add to my profile. And because of this need I have gone the extra miles for your project …

In fact, I have already completed the job – converted your image into a vector and made the requested changes to the running man. I will remove the watermark if you choose me for the job and send you the vector file immediately in exchange for a glowing review.

Please check out my profile for additional examples of my work

It was the first time I had taken the risk of completing the job before the client even had a chance to hire me. But the tweak only took about 10 minutes to complete and I was so desperate at the time, it was a risk I was willing to take. Luckily, it paid off. The very next day, Jacob, my first Upwork client paid me $10 and left a glowing review. 

Editor’s Note: You should never offer to do free work on the platform as it is against Upwork’s Terms of Service. Had I not received an offer or been paid for the work, I would have not released the deliverable to the client. Also, you don’t have to dangle a low rate in front of potential clients to get that first job like I did. It’s just the strategy that happened to work for me. It was extremely difficult to swallow my pride and work for such a low rate when I was already earning $75 per hour off-site. I just treated the discount as a marketing expense.

My key takeaways

My key takeaways from that initial experience were as follows:

  1. Upwork clients want to know that you’ve read the job description.
  2. Prospective clients want assurance you are capable of doing the job.
  3. Clients appreciate honesty.
  4. 5-star reviews are crucially important.

With newfound confidence and a shiny new review on my profile, I began applying those key takeaways to the next handful of proposals. As suspected, landing the next few new jobs didn’t require a lot of time – at least not as much as the first job did. I was able to secure my second job just two days later. And I didn’t have to put in any preliminary work to win the second one. The 5-star review from my first job spoke for itself.  

Winning your second Upwork job

Below is the cover letter I used to secure my second job.

Hi There!

I am new to Upwork – but not new to graphic design. In fact, I have over 15 years of professional experience. And making infographics is my forte!

I’d love it if you would consider me for this project! I do not have the 100 hour requirement that you’ve listed but I only just joined this website last week. In the real world, I’ve logged thousands of hours and charge rates of up to $75/hr so I can assure you this proposal is quite the bargain.

And just as I had suspected, with each new 5-star review, jobs became easier to land. Within a few weeks, I saw my Job Success Score begin to improve and soon thereafter I secured a Rising Talent Badge for my profile.

Bonus Tip: Consider weekend work

While I don’t have any data or case studies to back up this theory, in my personal experience I also find that Upwork jobs are easier to land on the weekends due to less competition and a high volume of job posts. Oftentimes, small businesses use weekends to launch startups or work on side projects that they don’t have time for during the week.

And established freelancers who can afford to be picky (like myself) frequently opt out of weekend work. I don’t even check my Upwork inbox on the weekends. This means less competition for the newbies. More clients and less competition might just be the leg up you need to score your first job on Upwork.

Frequently asked questions

How long does it take to win your first job on Upwork?

Landing that first job on Upwork, even for an otherwise successful freelancer, can prove to be a difficult task. And for complete beginners with zero experience, it’s nothing short of overwhelming. Even as a competent freelancer with plenty of experience before joining Upwork, it still took me almost two weeks to land my first contract on the platform.

So how long does it take the average person to win their first Upwork job? The truth is, it could take a single day or it could take several weeks. Most seem to report an average of 2-3 weeks. The key is to not let yourself get frustrated if you aren’t an overnight success. It’s going to take time. At the end of the day, winning your first Upwork job is just a delicate balance of strategy, persistence, skill, and a little bit of good luck.

How long does it take to start making money on Upwork?

While everyone’s definition of “real money” or a “full-time income” varies, when I originally joined Upwork I had a very specific personal goal in mind: to make $6,000 per month as a full-time freelancer. I am happy to report that after three months of consistently applying for jobs and asking for reviews, I was earning $75 per hour and was making roughly $6,000 per month on the platform.

Morgan Overholt Upwork
Morgan Overholt’s Upwork Profile

How much do you make today?

I wanted to include this brief blurb about how far I’ve come on Upwork, and as an entrepreneur, in the last five years in hopes that it might inspire me. While I still use Upwork today, I don’t lean on it quite as much as I used to. At the height of my Upworking, I was making around $10,000 per month on the platform, which represented roughly 40-50% of my total income. 

Today, Upwork makes up about 20-30% of my monthly revenue at an average of $5,000. The rest of my income comes from freelancing off-site and blogging. To date, I’ve earned over $600,000 on the platform. My current hourly rate is $190.

I also recently reached out to Jacob, my first-ever Upwork client, and thanked him for giving that newbie Upwork freelancer a shot back in 2017. Never forget the people that helped make your dreams possible.

Did my “Upwork origin story” offer any insight? What do you think is the best way to score that first job on Upwork? Let me know in the comments. Also, don’t forget to connect with me on social media using the links below.

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Morgan Overholt

Morgan has almost 20 years of professional experience in graphic design and a bachelor’s degree in Computer Science. Her successful freelance business has been featured in articles that have appeared on, Refinery29 and Business Insider Prime.

14 thoughts on “This is How I Got My First Job on Upwork – From a $600k Freelancer”

  1. Hi Morgan, thanks for sharing your journey!

    I also got my first design job within two weeks of joining the platform. However, I think I’ve seen and heard of a lot more people who have a very different experience. Some have had to keep sending proposals for up to 1, 2 or even 3 months before getting their first job.

  2. Hi Morgan,
    I am commenting all the way from Nigeria.
    I am also new to Upwork but is yet to land my first gig as a content writer and it is frustrating. I just received your jump-start kit and I am following up ardently.
    I would love it if you could help me, possibly take a look at my Upwork profile and mentor me in the long run.
    Looking forward to hearing from you.

  3. Hello Morgan,
    I found this helpful. I’m a newbie to Upwork but I have close to a year experience in content and blog writing.

    I had always felt my proposals aren’t good enough, although I get a once-in-a-while interviews but still yet to land a gig. I have submitted a lot of proposals.

    But I hope by the time I’m done with all the information you’ve provided, I can start earning and building a good Upwork reputation. Thanks, Morgan

  4. Hi Morgan
    I want to say I love you and thanks for giving us a chance to shine.
    I have been on upwork for more than 6 months and nothing has happened I started following your post and yesterday after 9days of sending proposals I got a message although I don’t know if am doing well talking to the guy but am very happy I am able to get an invite it has boasted my confidence

  5. Yes it is really insightful reading your experience . Will give newbie like me more confidence in applying for jobs on upwork

  6. Hii Morgan,,,this is inspiring,,,i’m now looking for a second gig,,,never giving up has been the deal,,,and with this inspiration,,,now i’ll go on an on,,,youre officialy my new role model,,,I almost gave up and went back to waiting for the next College semester but now I’m good to go,,if there was a way to always keep you close like a hall moniter it’d be great ,This is Jack all the way from the Nairobi, Kenya. Thank you,,,

  7. Hello Morgan,
    Thank you so much for sharing your first and second proposal letters. I am looking to the freelancing world for Bookkeeping – using QuickBooks Online.

    Please help me with how to write the propsal.

  8. I love your content , and i will like to have the best time for you to teach me one or two things
    I’m new to Upwork

  9. Just stumbled upon this article. New to Upwork. Don’t have as many “Graphic design” or “website creation” experience, but am looking for work in the e-commerce niche or others.

    One question.. how many “connects” do you use for jobs? Do you always try to be in the top 3? Overload all monthly connects into one job offer? Or spread them out across many opportunities? Thanks!

  10. Hey Zach! I strongly recommend subscribing to my newsletter to get my free Upwork Jumpstart Guide where I answer these questions in great detail!

  11. Hi Morgan
    I’m Precious Bello from Nigeria.
    I’m new to upwork, but I love writing.
    Still trying to get my first job….
    I need help

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