How to Land Your First Writing Job on Upwork

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Freelance writing isn’t for the faint of heart.

And, doing so on Upwork is going to require even more of you.

But, the difference between you and others is that you’re reading this and willing to make a change—while others will be repeatedly bashing their heads against the walls that are standing between them and the clients on the other side.

They won’t change their ways and will eventually give up. (Some might try to figure out how to get back into writing, but most won’t.)

You, hopefully, will take this advice (or at least that of someone else) to make an adjustment and adapt to the environment being a freelance writer on Upwork requires.

But you should know—I’m not here with a secret potion that will make that aforementioned wall disappear.

No matter how you approach it, you’re going to have to scale it in the end.

I’m here to give you a boost, though.

You should also be reminded that striving to land your first job on Upwork isn’t uncharted territory.

Think about it—even the absolute most successful person ever on the history of Upwork, or Fiverr, or elsewhere started at level zero; not one job under their belt as they searched and sent proposals and crafted their portfolio…a lot like you are now.

So, take a deep breath.

It can happen. You just have to be willing to stick to four basic principles along the way: be different, be a good person, be emotional, be disciplined.

With each of the steps below, keep those “4 Bes” in mind, as they really are the guiding light.

So, let’s take a look.

How to Land Your First Job on Upwork

1. Fill Out Your Profile (I Mean, Come On)

If you’re reading this, I’m going to assume you’ve already submitted your Upwork application and have been accepted as a freelancer. If not, then that’s a whole other story altogether.

I’m also going to assume you’ve already filled out your freelancer profile.

I mean, if you haven’t, and are growing frustrated that you aren’t landing jobs on Upwork, you really have a long road ahead of you.

For sake of clarity, my point is, you MUST do all the small things. You really don’t get to pick and choose here. Filling out your profile? That’s a small thing, and is an absolute must.

So much so, that I’m not going to go into major detail here.

Really, your profile won’t typically land you a job, but it can sure decrease your chances of doing so.

Absolute Must-Haves:

  • Profile Picture: Upload one that clearly shows your smiling face.
  • Rate: Figure out how much you want to charge as a freelancer, and don’t be afraid to own it.
  • Description: Your first writing prompt; grab attention and go.


  • Video: To the client, you’re a stranger; a video could help. But, you need to do it well. If you have a video, it might get watched, and a bad video hurts you more than not having one at all.
  • Proficiency Tests: As time allows, complete some of the given proficiency tests, but I personally don’t think these are looked at as much for writers.

2. Search Early and Often

Many beginning freelancers make the mistake of treating their clocks like dartboards.

Meaning, they might search for jobs at 10AM one day, or 2:30PM the next, or 10PM the day after that. If your personal schedule requires such randomness, then there really isn’t anything you can do about it.

If not, and say, you have a few regular windows of time each and every day to dedicate, you must take a disciplined approach to searching for jobs.

For instance, you might only have time to write after you get off of your full-time job. Your options, then, would be to search for posted jobs at 5:30PM when you walk in the door, or 6:30PM after you eat dinner, or 8PM when the kids go to bed, etc.

My advice? Develop a routine and be disciplined in carrying it out. That means checking postings the same time every night to get yourself in the habit of doing so. You never know what’s going to come across and when.

My other advice? If you only have the nights to work, check new postings in the morning when you wake up, or when you’re sitting eating breakfast, etc. Then, use what other free time you have during the day to check for any jobs that have been posted since you last checked, say like once an hour.

Yes, that means perhaps using your lunch hour or mid-day coffee break to search for jobs. Unfortunately, you’re going to have to give up some things of leisure if freelance success is what you’re aiming for, so you might as well start making adjustments now.

I really feel the early bird gets the work here, with countless clients replying to my proposal rather quickly after it was sent, meaning they won’t see or even consider the many proposals that hit their inbox later.

The logic is simple—clients have needs/issues/problems. Nobody likes to have problems, and thus will be willing to move quickly to take care of them.

Remember, one of your best abilities is availability. Quick responses hint at availability.

3. Bid on the Right Jobs (Posted by the Right People)

One complaint people have about Upwork, especially when comparing Upwork and Fiverr, is that you only have so many “Connects” or credits to use when bidding on jobs.

For me, such a limit was a blessing, as you really have to think carefully about the jobs you’re targeting.

I’ve gone into great detail on blogging jobs for beginners, and the formula and thought process holds true here, for all types of writers, and all types of writing.

There are specific jobs and clients you should be going after as a beginner in order to increase your chances of landing one.

Jobs from the client new to Upwork

Being new to Upwork, you’ve felt overwhelmed at times, right? The same goes for the client who is just starting out and looking to make their first hire.

They post something like a simple blog post job and get bombarded with proposals from freelancers claiming to be the absolute best with thousands of years of experience, and in possession of all the accolades imaginable.

Use that to your advantage.

When I was just getting started, I would routinely explain the fact that I too was new to the exchange. If the goal is to establish a connection and build rapport, that’s one similarity/asset you have at your disposal.

Of course, you still need to prove your worth, showcase your portfolio, etc., but this can give you that much needed initial connection.

Jobs asking for something only you can offer

OK, maybe not only you, but jobs with requirements so specific that they cut the applicant pool in half or more, with you being in the half that can actually provide what’s being sought.

For example, maybe the client needs a blog post in two hours. As you’re sitting around the apartment without any other jobs on your plate, that could be you!

Posts like this pop up all the time:

“Today,” “ASAP,” “24 Hours”—you’ll see such urgency often. If you have the time to deliver, definitely take the shot.

Alternatively, maybe the client needs some type of professional experience or skill. Something like:

Such a posting immediately eliminates a very large percentage of freelancers out there, paving your way to success if, in this case, you are in fact an app developer or have related skills.

Again, it’s an example—if you aren’t an app developer, don’t fret. Clients seek writers with skills and experiences in a variety of other areas and disciplines, too.

There are many other types of jobs you should be targeting, so I encourage you to check out the post. If not, at least keep an eye out for the following:

  • Jobs from the client who receives great feedback from freelancers
  • Jobs from the easy-going client (you can get a sense of this from their job description)
  • Jobs from the focused client (the one who knows what they want will respond to those who address their needs)
  • Jobs from the client who already did most of the work (editing, proofing, etc.)

4. Bid Like You Mean It

This part never makes sense to me.

You’ve spent precious resources searching for jobs and even more time making sure you’re bidding on those that will give you the best chance at succeeding.

But now, when it comes time to send your proposal, you’re going to mail it in? Or cut corners? You’re going to copy and paste a proposal you sent previously?


I’m all for efficiency, and I’d certainly be lying if I said I didn’t use a proposal template in my own dealings.

But, such a template shouldn’t resemble Swiss cheese, with block of text on block of text, and then a small space or hole where you make your customizations.

See what I mean? Plugging in a variable 3-4 words isn’t customization. It’s robotic. And it’s what most of the rest of your freelance competition is doing.

You need to be different. You need concrete, real-life details to sell yourself and your skills.

Instead, your “template” should look more like this:

See the difference? There is almost as much variable space as there is “templated” content.

Does it take longer? Of course. That’s why others aren’t doing it, and it’s one way you can set yourself apart from the pack.

Here is an example of what a proposal can look like by following the above:

To explain, with each and every proposal, you should really do the following:

  • Use the client’s first name. So easy.
  • Use an intro line that conveys the complete opposite feeling of, “Hi Dave, I’m Ryan, a writer who can help you.”
  • Include a personal, rapport building connection that doesn’t necessarily have to do with writing skills, specifically. The goal here is to show you in fact read the entirety of the client’s proposal, and, that you’re human.
  • Give the client a freebie. Just as it sounds—give them some type of “free sample” or valuable tidbit that will set you apart from others. Above, it was a few points to include in the required blog post.
  • Include a question or two about the project. The goal here? Get them to respond in some way, shape, or form. Even If they disagree, that’s OK. You’re on their radar, and I can guarantee they haven’t made such contact with others.

Really, you need to use every piece of given information as an asset. If they give their name, use it. If they add their website, visit it. If they state a pain point, address it. Be different, be human.

5. Rinse and Repeat

Let’s face it, you’re not going to land a job on your first shot; maybe not even your first 10.

But you need to remember that every past failure has no bearing whatsoever on your ability to land the very next job you bid on.

So, you really need to be disciplined in your ways, ensuring you’re giving yourself as many chances as possible to be different, and thus, to be selected.

Not to mention that practice truly does make perfect.

During this time of “rejection,” you’re also creating more and more portfolio pieces, and as mentioned in the example above, maybe you’re posting content to self-publishing platforms like LinkedIn, Medium, etc. Sure, you might not have “professional experience,” but who cares.

You can create your own experiences, showcase them for your potential Upwork clients, and be well on your way to landing your first job on Upwork.

What have been your specific challenges? Email me or post in the comments!

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About Ryan 41 Articles
Ryan is the owner of Rent My Words, a business and site started to help everyday people, (beginners without any experience, basically) find success with marketing, their writing projects, and freelance work on platforms like Fiverr, Upwork and others.