How I Booked My First Recurring Freelance Writing Job

This fantastic article is from Kelsey and was originally posted on her site, TealMama. Following are some great steps on how to get started as a freelancer– one of the quickest ways to become a digital nomad. If you’re serious about becoming a digital nomad, seek out recurring clients and you’ll find yourself with more than enough work in no time at all. And now, over to Kelsey.

Here are the steps I took to book my first freelance writing client on an on-going, indefinite basis.

I continued to educate myself

I researched as much as I could about freelance writing.  1) I signed up for‘s e-mails and course.  2) I searched for freelance writing related blog posts and articles.  3) I signed up for e-mails from Copyblogger.  I tried to learn as much as I could!

I built an Upwork profile

There are other platforms, but I have heard the best reviews about Upwork.  Yes, they do charge you a percentage of what the client pays, but Upwork gives you a lot of access to clients.  They recently changed their rate structure based on the sales volume per client.

Another complaint you’ll hear is that there is too much competition on Upwork.  But I think you’ll be surprised in your abilities to stand out when taking the time to submit good proposals and be yourself when you interact with your client(s).

Tips I will give beginners like me – be yourself, keep it simple and don’t promise too much.

Here is my current profile.  Notice it’s very simple.  I don’t make any promises or claim to be an expert.  And my rates reflect that.  Eventually, I’ll be able to raise my rates as I gain experience and a solid portfolio of work.

Upwork profile

Take the relevant tests available on Upwork.  I scored in the top 10% in U.S. English Basic Skills, and I am no English major. ?

But I think this gives clients a little more confidence that you’ll be able to get the job done well.

Upwork test score

I also added work experience to my portfolio and tailored it to writing.  For example, I listed my prior finance analyst job and mentioned that I had experience writing business cases and executive presentations.

I started a writing portfolio

I wrote an article on how to keep an automotive shop clean — using knowledge I had from when my dad owned a tire store + I pulled in lean/5S knowledge I learned when working for an aerospace manufacturer.  The more you use your own experiences to draw from the better.

Now I’m adding articles to my portfolio that I have been paid to write.  However, in the beginning you’ll have to write a few samples of your own.

I started a blog

I started to apply for a few writing jobs.  However, I shifted focus and started working on my blog.  Which turned out to be a blessing in terms of freelance writing.  I could now point the potential clients to my blog to give them a really good idea of my style of writing.  Plus I think having my own site really helped with credibility.

I gained confidence

I started to get more and more requests for interviews on Upwork.  Some interested me, some didn’t.  Be aware that some people on Upwork are looking for super cheap (not even worth your time) writers, but there are others willing to pay for quality work.

Once I let go and responded to the interview requests with confidence, and in my true voice, is when I was able to book my first on-going client.

PS – this past week my client was really happy with my work and will be sending additional work my way for articles/blog posts they are behind on.

In conclusion, my advice is:  research and find someone to learn from + build a profile on a highly visible platform such as Upwork + keep building your writing portfolio + be yourself!

About the Author: Kelsey is the author/owner of tealmama. Montana wife and mom of two. Former finance analyst – now work-at-home mother. She enjoys making/sharing delicious recipes, finance and business planning.

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Rob is enthusiastic about everything related to money and investing. A financial analyst and instructor, he enjoys using what he’s learned from 10 years of studying business and money to help others achieve financial stability. He founded Money Nomad in 2014!

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  1. Hi Rob! I’m extremely honored to be a part of your 90 day series on becoming a digital nomad. And looking forward to participating in the remainder of the journey! I really believe this free course will give people the tools they need to change their lives in a very empowering way. This big of a change seems impossible until you start. And with so many resources out there, it can be overwhelming. So having this much great information in once place (for free!) is so awesome. Thanks again!

    1. And I’m excited to have your contribution Kelsey! One of the best motivators is seeing other people achieving what we hope to accomplish — and your post has some great insights! I appreciate you sharing.

  2. Thanks for info, I’ll definitely save this post for reference later. I’m still in corporate America but as I transition into retirement one day hopefully soon I’ll look into this for a side project and some extra money. I hadn’t heard of upwork before so will have to look into it more. Thanks again!

    1. Yep! Upwork is definitely worth using. Although there fees are high, the value they provide makes it one of the easiest tools to break into freelancing. And, if it saves you 20% of the time it would take to find clients on your own (which it often does) the fee is worth it.

      Thanks for commenting!

  3. Great tips. I have several recurring contracts through Upwork and even was awarded one where I proposed a bid higher than the client’s budget! I also look at Copyblogger & have realized some clients advertise on both platforms. But definetely have had the most success with Upwork so far.

    1. That’s been my experience as well — Upwork seems to be the easiest way to find clients until they start contacting you directly or being referred by other happy clients.

  4. Just curious about something. What if you have limited work experience? Due to my poor health and stamina I have only been able to do some substitute teaching here and there, some tutoring, and home companion work. I also have done some volunteering. I guess I could count some of that?

    1. Great question Rachel. Freelancing is all about what you can produce/deliver, not what your background is. So, if you can write an amazing article or help someone design something or sell products, they’ll pay you for it!

      The bad side of that is if you don’t feel very productive one day you won’t make much money – as clients aren’t going to pay for 8 hours of work if you didn’t deliver anything. So it’s a double edged sword.

  5. I have to say, I learned the hard way that honing freelance skills are the best step one to online income and digital nomad. Thanks for outlining your process!

  6. Pingback: June 2016 Progress Report - tealmama

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