Freelancing on Upwork: My First Client

Bennett Garner
5 min readJun 5, 2017


This is post #2 in my Freelancing on Upwork series. Post #1 is here.

This week I tweaked my profile a little further, changing some of the language in my profile page and taking a few tests to demonstrate competency. I also uploaded a bunch of previous work to my portfolio. (If you don’t have previous work, I’ll explain what to do in a minute.)

Then I wrote a total of 8 proposals this week. I wanted to write more, but since I’m working from Uganda the internet is slow, and my attention was divided.

Here’s the method I used to find these jobs…

How I searched for copywriting jobs

Upwork has great search functionality for new jobs. I simply typed “copywriter” into the search bar and applied some filters to find the jobs I wanted.

Here’s what my search screen looks like (I saved this search and came back to it multiple times throughout the week.)

You can see the filters I have applied:

  1. Fixed price — I don’t want an hourly, ongoing contract. That wouldn’t be conducive to working from Uganda. Also, I use a Chromebook as my laptop, and Upwork’s time tracker for hourly projects doesn’t work on Chromebooks.
  2. Entry level or intermediate — Since my profile is brand new, I don’t want to apply for expert level jobs yet. I need someone to take a chance on me first and get good reviews.
  3. Price $50-$200 — This weeds out all the tiny tasks that are bottom feeders. The $200 limit means I’ll find projects that I can finish while working part-time in Uganda.
  4. Payment verified — I prefer to work for sure money. A job posting with payment verified is more legit in my opinion.
  5. U.S. only — Freelancers in the U.S. can add their bank information to confirm they’re U.S.-based. Then, they can apply for jobs where international competition isn’t allowed. In copywriting, many job postings have this requirement so they know they’ll get a native English-speaking copywriter.

Then, I’d look through the results and apply to jobs that interested me. I wouldn’t recommend applying to jobs that are a few days old. Those are probably already taken.

Also, consider how many other people have applied for the job. If it’s 20+, it seems obvious your chances of winning the job are significantly lower.

My proposal and cover letter

Doing my research I found most cover letters focus on the freelancer. They talk about years of experience and personal interest.

I wanted to do something different with my proposal. Danny Marguiles’s Freelance to Win was the most helpful resource I found on this front.

Danny suggests giving advice to the job poster in your cover letter. I told my potential clients about the biggest mistakes I see when people hire copywriters or write sales copy.

He also suggests creating a 200–400 word writing sample specifically tailored to the job poster’s niche. Giving away free work is against Upwork’s terms. According to Danny, the key is to take 20 minutes to create similar, but unusable content that proves you can do the job without actually doing the job.

That’s what I did for all 8 of the proposals I submitted this week.

Here’s one of the cover letters I submitted:

Results of my first week on Upwork

Of the eight proposals I sent in my first week using the above formula, I only heard back from one person. Three of my proposals were rejected, and four are still pending (it has been a few days, so I don’t think I got the job).

Still, one out of eight is a great ratio. I’ve heard stories of people taking a month to get their first Upwork job. It took me less than a week. I think my results are part luck and partly a result of my cover letter and relevant samples.

The guy who was interested received the above cover letter. He’s a real estate agent and wanted an email drip campaign implemented.

He sent me a message asking me if I’m still interested in the job. Since I’m new to Upwork, I’m not in the habit of checking my messages. It took me a few hours to respond, and by that time he had offered the job to someone else.

Luckily, he had some other writing needs and liked my writing style. He asked if I’d be willing to tackle some articles for his new Minneapolis real estate blog. So that’s my first Upwork job!

Structuring my first job & budget

The client needs a total of 16 articles written. I asked if we could split the job into 4 articles first, then 12 later. My reasoning was I wanted to get used to working with the client and see how much work was involved in the first 4 articles before agreeing to all 16.

I’m writing these articles for cheaper than my normal copywriting rate because I want the Upwork experience. Honestly, I’m also having trouble prospecting new leads on my own, and I hope Upwork will help me find more work.

That said I’m doing 500-word articles at $15 each, so $0.03/word. Not an outstanding rate, but the articles are easy to write so far. I knocked out most of the research/writing on the first 4 in just three hours yesterday.

4 articles = $60 / 3 hours = $20/hour.

In the future, I’ll command much higher rates, but this isn’t a bad first Upwork gig.

In total, the 16 articles will pay $240.

What’s next

I’m editing my first four articles this morning, then I’ll submit them for review and payment. At that point, I’ll have my first Upwork job completed!

In the next installment, I hope to share how the payment system worked. Hopefully, I’ll have a shiny five-star review to brag about!


If you’re interested in Upwork or freelancing, please follow along on this Medium series. You can get updates when I publish a new post by following me.

This is part 2 of a series on my Upwork experiment. Part 1. Part 3.

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