Freelancing on Upwork in 2021: 5 lessons I’ve learned this Year

Toluwalope Ajetunmobi
4 min readNov 1, 2021

Freelancing: Good? Bad? Great? Ugly?

If you’re just starting as a freelancer on Upwork, buckle up because you’re in for a long ride. There will be moments you’d feel on top of the world. And at times, you’d be at the lowest: you don’t want to get out of bed to face anyone.

I should know! I’ve been Top-rated on the Upwork for close to six months, and I passed $10K last month. That is $10K in a year or so (P.S. I took months off this year).

There is a smile on my face as I write this because there were some hilarious and depressing moments. I’ve met some great clients, no, not great, amazing people!

I started the year with a well-vetted plan of expanding my freelance business on Upwork — or so I thought. I had grand plans!

But…

I got back into school for my postgraduate studies and had to focus less on freelancing. In fact, I took some months off. Overall, I’ve made over $8K this year alone.

What have I learned?

Tons of freelancing lessons!

Some I learned the hard way. But you don’t have to go through that.

In this piece (my first on medium), I’ll walk you through important lessons I’ve learned about freelancing and Upwork this year.

Here are five lessons I learned from my first year of freelancing on Upwork.

  • Create a niche for yourself

As a newbie, you may feel like being everywhere will help you get more jobs. But that is not entirely true. Instead, you want to position yourself as an expert to get the best deals on Upwork!

Of course, you might take some general jobs to get your first reviews. But after that, find your niche (s). Your niche (s) should be areas you’re comfortable working in. For example, as a writer, focus on areas you like to write about.

  • Create a pricing structure

You need a pricing structure! How much are you comfortable working for?

Keep in mind that you might start with a lower price to get your first review. But after that? Get comfortable increasing your rates. Don’t fall for that mistake of lower prices will attract more clients!

I have found out the hard way that low-paying clients are usually the most stressful and difficult to work with.

Guess what: Almost all the instances I made the mistake of going below my pricing structure, I ended up regretting it. I get underpaid, work more, and get bad reviews.

So, don’t do that; stick to your rates. Ideally, your rates should be a range of the prices you’re comfortable working with.

  • Be selective

Don’t apply to every job posting; you will end up wasting your connects. Instead, always be selective of the jobs you apply to. Have criteria and a process of choosing.

I apply to projects in areas I like to write about (marketing, business, finance, and general lifestyles). I also vet the clients thoroughly; any funny business and red flag!!!

Besides that, I make sure I can handle that project well. For example, can I deliver a fantastic piece?

I don’t want to disappoint the client; that is bad for my reputation and my business.

Also, make sure you’ve at least one or two portfolio pieces in that niche. Why? It helps your credibility and, in turn, increases your chance of getting the job.

  • Write targeted proposals

Don’t copy and paste proposals! While it may seem like generic proposals can help you apply to many jobs faster, it does more harm than good. Clients can easily filter generic submissions, and that will hurt your chances of getting a response.

Instead, take your time to read the job description. What are the client’s needs? What do you think will appeal to them?

I recently got a project because I appealed to the client’s need for diversity. I simply stated that I was a female writer from Nigeria (a third-world country). Why? Because I could sense from her job posting, she’d like that information. And, of course, I had fantastic writing samples.

It turns out she had stayed with her family in Nigeria when she was much younger. She sent a reply almost immediately, and we started talking.

See what I did there? That is me finding a connection to appeal to the client. But this approach won’t work for other clients.

Before you send in your proposal, check the description for ways you can impress the client and make them want to work with you.

  • You need a support system

Lastly, you can’t figure everything out yourself! You need support; don’t stop learning and unlearning. Find successful freelancers (Upwork and off- Upwork) and follow them. Subscribe to their YouTube channels and their email newsletter. If you can, buy freelancing courses and keep learning.

Let’s face it; freelancing can get tedious and frustrating. At some points, you’ll question every move you make. You need a great support system to get through those depressing moments. For me, it’s talking to people and going back to learn more from my list of freelancers.

In conclusion, freelancing is not for everybody! It will work for some, and for others, it won’t! Don’t be deceived; it is not all sunshine and roses. Sometimes you get it right; sometimes you don’t. But with the right attitude, you can get the result you want.

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Toluwalope Ajetunmobi

Web3 Content Manager and Writer | Exploring Content Marketing in the Web3 Space