The Roadmap to Upwork Success – Takeaways

Last updated on July 11, 2020

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Why has my profile been rejected? Why haven’t I landed a contract on Upwork yet? I am a good writer but what else can I do on Upwork to increase my income?

Those are just a few of the questions I, and a few of my colleagues receive on email and via Facebook.  To share tips on how to succeed on Upwork, I, David Mbugua of and Kevinson of, teamed up and organized the above seminar.

We had a little over 50 attendees – all very psyched up!

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It was educative and also entertaining. What an audience! They were so engaged. 

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David Kiongo talked about the importance of diversification. And why should you diversify?

  • To increase your income
  • To spread your risks. If you are a transcriber and jobs are scarce on a particular week, you can always take up writing or captioning jobs if you are skilled in those areas. 


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He also showed the attendees how to create an amazing Upwork profile – step by step. And there was so much more that he shared.

Kevinson talked about article writing – how to be an amazing writer as well as the do’s and don’t of writing an Upwork proposal while bidding.

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Stuff such as

  • Do mention the client by name. Avoid terms such as ‘Dear Hiring Manager
  • Attach relevant samples every time. 
  • Avoid I,I,I. It’s not about you.  The client has a problem. Show them you have the solution

And there was so much more that he shared! 

And then there’s yours truly!


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I talked about the importance of outsourcing, why transcribers need to set up their profiles on Upwork like yesterday, hourly and fixed rate jobs. How do they work? What are the pros and cons? I also talked about the different types of clients you’ll meet on Upwork: 

  • The clueless client
  • The frustrated client
  • The over-involved client
  • The scammer
  • And I shared who among the three is my favorite. The clueless client!

And I shared so much more too!


At the end of it, we had testimonials from three Upwork freelancers. My oh my.  Their stories were inspiring. Very encouraging. 

The video is going to be out soon. In the meantime, here’s a sneak peak!

About the author

Virginia Nakitari is a work from home mom passionate about making money online. She's here to show you legitimate companies offering full-time, part-time and remote jobs from home! Stay tuned!

  • Kindly let me know when the video is out!

    Oh, and how to possibly get in touch with you for the same advice. Thank you.

  • I was in Nairobi that day to buy a laptop and attend the seminar but i only managed to get the laptop. Eagerly awaiting the video

  • Hi,
    Do you hire writer to work under you? If so, what is the procedure to get hired. I have been writing articles online for a few months now but the work stream is not flowing reliably. I need another avenue.

    • Hello Lydia. No, I don’t hire writers. My area of expertise is transcription. Have you tried getting work on iWriter, Fiverr, Upwork and

  • Hi ,
    Thanks for your blog, I would like to know more about transcription, how can i get to that industry? When do you guys organize such seminar as shown in a trailer above?

    • Hey John. You can find out more about transcription from my eBook. I have shared all my tips and tricks therein. As for a seminar, I’m not conducting another one soon. 🙂

  • This is great Sheeroh. Continue helping us in this online journey and may you be blessed. Maybe to ask, I am currently at AjiraDigital training at The UoN and saw a familiar face, could you be the one who introduced herself to us on Monday 6Th August,2018 at the UoN towers?

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