How To Land Your First Online Writing Job on Upwork (And How I Landed Mine)

You’ve decided you want to make money writing online.

Great. There’s just one teeny weeny little problem.
You don’t know how to start.
I mean, it’s pretty straightforward when you want to get a job offline, in real life.

You crank out your C.V. and application letter, find companies that require your services, apply for the jobs, kill it at the interview and voila, the job is yours.

The path to landing a writing job online is not that straightforward.

You have heard about job sites (or if you haven’t, I’m telling you now- there are job sites online) but you still can’t quite figure out how to land that first writing job.

Coursera business 728x90
Especially when there are bizarre stories of people who seemed to be doing one thing and all of a sudden, they start landing high paying job, after job… after job.
It reminds me of a quote (and a good rule to live by, if you are ever interested in investing in a business):

” If it sounds too good to be true, it probably is.”

In other words, those stories are more often than not, highly exaggerated versions of what actually happened.
There’s no such thing as an overnight success.

Okay, Tomi, stop and go back to the topic.

So how do you go from no writing job to more writing jobs than you can handle?

Well, first thing you need to know is that it’s not going to be easy.

Many of the biggest names in blogging/ writing online have been on this hustle for close to 6 or even 10 years. Back when many of us were still running around trying to look fly and get into the university. (or was that just me?).

There are many ways to land writing jobs but for this article, we’ll focus on how to land your first writing job and get this ball rolling.

When you’re first starting out, you’ll face two main problems.

One, you don’t know where to start looking for jobs.

Two, you don’t know how to apply for writing jobs online. Do you just say:

“Hey, what’s up. I can write for you?”

Or is there some special procedure?

We will get into the answers to both of them a bit later, but first, let me tell you a short story about how I landed my first writing job.

It all started with a seminar.

Many moons ago, when I was unemployed, I had a lot of relatively free time on my hands… so I added “going to business seminars”.

One of the speakers was talking about how unemployed youth could earn money. Then he mentioned Upwork and how people were making money writing on Upwork and a light bulb lit up in my head.

I thought to myself : “I have to do this as soon as I get home.”

So I did it. Applied to almost 30 jobs before landing my first one.

The End.

Actually not really. I got kicked out of Upwork for some shit but that’s another story.

Real short and sweet.

Check this out!  The 3 Ps To Get More Customers Online

Now, let’s talk about how problem one- Not knowing where to start.

Well, for starters, just like I did, you could get on Upwork.


How to Land Your First Online Writing Job on Upwork

The first thing you want to do is to create a great profile. And that all starts with a friendly face.

In other words, your Upwork profile picture has to be one of you looking good, and preferably smiling.

Now, I don’t mean upload a picture of you at a party.

land your first online writing job

Not a Great upwork profile picture.

Your profile pic should find that sweet spot between “serious” and “cool” and be that. Do this and you’re golden.

Hire Freelance Writers Now from

Next, you have to sell yourself on your profile.

To do that, you need to know:
– What makes you different from other writers online?
– What can you do that they can’t?
– What have you done that can give you an edge over the competition?
– What services do you offer in addition to writing? Usually, if you have some skill in SEO, that’s definitely a plus and something that must go on your profile.

Craft an amazing personal description of who you are, and what you offer using your answers to those questions.

Okay, I know I said amazing. But if you’re a total newbie, you might not have much ‘amazing’ stuff to mention.

Don’t let that stop you.

Communicate with passion in your profile and that will still draw your potential client in.

Remember to also fill out your rates in your profile.

And also your Skills. This is an important one, because there’s really no need applying for a job that you didn’t list as one of your skills.

It basically confuses the person who placed the job offer, and well, I haven’t been successful getting a single job I wasn’t qualified for, in some way.

I’m not saying it’s impossible, though. I’m just saying it’s better to list that job as one of your skills and apply for it.

Now, there are some more boxes to fill in but I think you can handle them on your own.

So let’s move on:

When your profile’s been set up, you’re ready to start applying to jobs.

Click the menu section titled “Find Work”

Upwork will bring up a list of projects and beside it at the left side bar, various options that help you specify what kind of jobs you want- from price range to hourly/fixed pay rate to duration of work, there’s a ton of filters you can use.

So do that, and be very specific. Although you’re just starting out, any job that does not require much “headache” will do just fine.

Now, when you find a job you want, open the link, craft a cover letter.

Don’t know how to do that?

Well, there’s a lot of info on that topic, but I especially like these…

How To Write A Cover Letter – Harvard Business Review

Upwork Cover Letter Samples– Webson Job

How To Write A Cover Letter– Upwork

Check this out!  Why You Need To Get High ... On Your Hustle

7 Upwork proposal mistakes– Freelance To Win

However you go about it, the important things to remember when writing your cover letter are:

– First things first, your intro and greeting.

I usually went with :

” Dear Project Manager (or if you have the name, insert Name here)

I read your job listing and I’m interested in this project. “

I know, I know, it seems a bit redundant. But most times, most people do not bother to read the job offer completely before they apply.

You need to read the whole job listing before applying, and I feel you should at least mention that you read it.

– Next, you need to make it clear to the client that you understand the job.

” After carefully reading through, I understand that you need a ( then go ahead to rephrase the client’s listed requirements in your own words) .”

– Then you need to explain to the client why you are the right man or woman for the job.

Here, you sell yourself. Explain briefly why you are the right person for the job.

If you have done any similar job in the past, now would be the time to mention it. Also, if you have acquired any skills or diplomas (or whatever) now would be the time to bring it up.

P.S. If you haven’t done either, don’t fret. I hadn’t done either and I still got a job. You just have to sell yourself differently. Talk about your work process, how long it will take you deliver the work, etc.

– Samples!

Here’s where it gets interesting.

Most writers just attach any sample of work they have recently done. And some don’t attach any at all!

Yes, some writers don’t.

Then they wonder why they don’t get the job.

Don’t be like that. But you also want to be strategic with what sample you use.

Look at the job  offer again. Then craft a sample close to exactly what your client needs.

That alone increases your chances of getting a job.

I learnt this from Danny Marguiles, one of the highest paid freelance copywriters, check this link for more info.

Okay, so you create the sample, then you attach it to your cover letter and say something like :

” I have attached a sample of my recent writing work to give you a better sense of my writing style.”

– Your closing.

Keep it simple stupid.

“I look forward to hearing from you. 

Best Regards,

Your Name.”

Rinse, repeat and apply for many jobs. Do this and you will land that first writing job.

Just like I did.

And then you can go from there, on to the more “writing jobs than you can handle” level.

Okay, a few Upwork tips:

* Your Upwork hustle is a business.

Take it seriously, and you will get paid. Or treat it like a hobby (as I did) and well, you’ll still get paid but maybe not as much as those who take it seriously.

* You don’t have to go for the cheap job offers.

Check this out!  The Sharp Guy Guide to Painless Keyword Research

Sure, you’re a newcomer and sure, you have zero reputation on Upwork. But that doesn’t mean you should automatically only apply for $10 jobs.

Build your reputation slowly. Get better at applying for jobs and proving to clients that you can handle their projects through a well crafted cover letter and sample.

Eventually you will land a job you really want at a price you want.

* Ensure you’re active on Upwork.

By that I mean, don’t just apply for jobs once in 6 months. You need to be checking in day in day out, applying for jobs (if you don’t have any jobs pending), completing jobs and getting paid.

That way, Upwork doesn’t ever send you this message I got a few months back:

land your first online writing job

* Your spider sense should tingle when a client wants to take the conversation off Upwork to skype or email.

Most of these clients are usually fraudsters who make you do a lot of work, and then disappear when it’s time to pay.

So be wary of them.

I’m not saying all of them are, though. I actually earned about $100 from one of these “Skype” clients, so they’re not all frauds.

A good way to weed out the frauds is to demand that you be paid after every job is complete.

Most of them would prefer you write about 15, maybe 90 articles for them in like 15 days before you get paid (I actually had this happen to me).

Then by the 15th day, they become unresponsive.

So don’t dull. If they’re serious, they will put their money where their mouth is.

* Don’t get depressed if you don’t get a job.

In the words of that Disney Character from Zootopia:

” It’s a hustle, sweetheart.”

You don’t get one job, apply for another and another, and just keep knocking till the door either opens or till it breaks in two.

Keep pushing. Keep grinding at it.

Whatever happens, keep moving forward.

As long as you never give up, you will succeed. End of Story.

Okay, now I’m done, been writing this post for close to a week, trying to get it perfect, but I just reread a post from Steve Harris today that put things into perspective for me:

” Imperfect execution beats perfect procrastination.”

Nuff said. And I’m done.

**Drops pen laptop and dusts shoulders off***

500Naira Writer has left the building.


Author: Tomi Joshua

Tomi is a case.

A bit brash, at first blush. But ultimately, he means well. There are very few things he won’t say or do in the presence of tolerant company (especially when it could make for a good story later).

Tomi is a Doctor, writer, certified inbound marketer (Shout Out to HubSpot), Digital Hustler, and online business addict.

He is most likely to be found dancing to the beat of his own drum, even in accapella.

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