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My Freelance Writing Journey: How I Went From Being Jobless to Earning Over $1,000 Monthly

Last Updated on July 30, 2019 By Chepkoech Ann 97 Comments

Freelance writing journey

Before early 2017, I knew nothing about freelance writing. I didn’t even know there were people making money out of it or from other online businesses. So how did I discover this invaluable gem? I’m going to let you know about it in a short while. But first, let me give you a little story of my life. 

The Little Story of My Life

Chepkoech Ann shares her freelance writing story

I’m a proud mom of two beautiful daughters. The first born will soon be starting her 3rd year as a BSc Electrical Engineering student in one of the local universities. The younger one is joining university in September 2019 to pursue a degree in BSc IT. 

Getting here hasn’t been easy for us, but I thank God for making it possible. I can proudly say that it has taken His grace for us to have come this far. We’ve been through ups and downs that have made us stronger together. I’ve learnt lots and lots of life lessons that have made me who I am today.

Now, let’s talk about how I ended up jobless in October 2016.

How I Became Jobless

It’s not easy getting formal employment without ‘serious’ qualifications. I don’t have a college diploma or degree even though I had joined university sometimes back in 1998. I had been a BSc Maths and Chemistry student in Chiromo for close to four years before I dropped out in my final year.

My dropping out had nothing to do with college fees but other circumstances. I went through issues that almost made me give up in life. In fact, were it not for my parents and other family members, perhaps things would be different for me. 

I thank God for these wonderful people who stood with me until I was back on my feet. It took me longer to accept that I was in a mess and I had to take the responsibility of turning my life around. 

After dropping out of university, I stayed without a job or any income-generating project for a while. My children and I were staying with my parents then. I eventually got a job with a leading supermarket in Kericho where I worked for two years before calling it quits. I had some little savings that helped me start a small eatery that went down after a year or so.

I was out on the streets job searching again. A few months down the line, I got another job with a construction company. The same company was later to transfer me to Nairobi to work in one of its major projects then. I worked there until early 2014 when I left to try my hand in business while still in Nairobi. My business picked up, albeit slowly, but also went down about two years later. 

At this point, I started feeling like business wasn’t my thing and perhaps I should try seeking employment again. I was out in the cold for about two months before getting another job with one of the leading milk-processing firms. 

I worked there for close to six months before those of us who had worked there for less than two years were let go. That was in October 2016. I was in a fix all over again. This is when I decided to go back to my parents’ place in the village and see what to do next.  

It wasn’t an easy decision to make, though. I couldn’t imagine going back home and starting from zero all over again. Remember at this point, my children were in high school. I had my immediate family members standing with me before I was back on my feet again. 

How I learnt About Freelance Writing

I’m an active Facebook user and this helped me discover ATK, a leading Facebook group for freelance writers, transcribers and others who were making it big online. I sent a request to join and was accepted shortly after. 

I came across posts from writers including Walter Akolo that focused on freelance writing. I also came to learn that Walter was an article writing trainer. That’s when I got curious and decided to send him a message on Facebook. I asked him about what I needed to become a freelance writer. 

Besides basic English grammar, the other things that he mentioned were a computer and a good internet connection. And of course, the training fee. 

I was lucky because my brother had a laptop and he wasn’t using it regularly. I borrowed it from him. That was one step forward.

My challenge was getting the training fee since I wasn’t working or earning any income then. I was broke to the core! The amount may seem too little but it’s a lot when you have nothing.

I asked my brother for some money and he gave it to me almost immediately. That was another step forward!

The Next Step…

The next thing I did was to enrol for Walter’s course. I found it quite helpful. However, I almost gave up along the way when I thought I couldn’t do it well. This feeling came when I was given a writing assignment to do. I wrote an article that I thought was great but the feedback I got almost discouraged me just because I had been awarded a 50% mark. 

Of course, the editor provided guidance on how to improve iit. I was to rewrite then resubmit, something that I didn’t do. Talk of having a thin skin then! This made me think freelance writing wasn’t for me despite follow ups from Walter. 

After that I tried my hand in transcription but I couldn’t hack that one either. I had to go back to Walter’s course. I couldn’t imagine staying idle and without an income any longer. Something had to give in. 

My First Job

I kind of started his course all over again. At least I could still access it. I kept asking him questions and guidance which he was still willing to offer.

I then opened an Upwork account shortly after and sent a number of bids. It took me about two weeks to land my first job. Though it wasn’t paying much, I was happy that I had finally landed one.

My first client gave me a five star review and I guess that’s what helped me land more jobs. I received five star reviews from my other clients after that. Here are some of them:

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The projects that I have successfully completed for my clients focus on niches like technology, business, travel, and beauty products.

I currently have four long term clients on Upwork with two of them sending me work regularly. Two of these clients were referred to me by another client who was impressed with my work. And yes, after 16 weeks on Upwork, I became a top-rated freelancer!

Freelance writing journey: Top rated in Upwork

Besides Upwork, I’ve also managed to bag other clients. They include direct clients that I cold-pitched and those that reached out to me through Facebook and Linkedin.

Earnings from my writing projects have been rising steadily. I even started hitting over $1,000 monthly from late last year, about 6 months after I seriously began my freelance writing journey. 

Conclusion

My writing journey has been both exciting and sometimes not-so exciting. 

I say exciting because it has given me hope again. I’m able to make an income that pays our bills including house rent. 

The not-so-exciting aspect of my writing journey has been the kind of challenges I’ve had to deal with.

They include rejection from clients and having to sit for long hours sometimes while trying to meet deadlines. I’ve even suffered burn out a few times and been forced to take a short break from writing. But the challenges have helped me learn a lot and grow even stronger.  

I’ve learnt that hard work, persistence and believing in my abilities can take me places. The other thing is to make sure that I deliver articles that meet and even exceed my clients’ expectations.

I’m not yet where I want to be, but I believe all that where I am at the moment is worth celebrating and being grateful for. My freelance writing journey hasn’t been all rosy, but it’s been worth all the effort. I’m glad I chose to do it.

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Comments

  1. Lucy says

    November 9, 2020 at 9:59 am

    Wow!soo insipiring

    Reply
  2. Judith Okech says

    September 24, 2020 at 11:59 am

    Where there is a will, there is a way. Congratulations!

    Reply
  3. Ruth says

    June 21, 2020 at 8:56 pm

    Wow, thank you for sharing your story. This has encouraged me to pick up from where I left and move on. Thank you.

    Reply
  4. Moses says

    June 19, 2020 at 10:29 am

    A very encouraging story! I am a beginner and would like to ask how best way to Start off this journey

    Reply
  5. Esther says

    June 9, 2020 at 6:19 pm

    Thank you for the inspiration. I believe i can still make it.

    Reply
    • Walter Akolo says

      July 16, 2020 at 4:28 pm

      Esther,

      Yes. You. Can!

      Thanks 🙂

      Reply
  6. Shem Omondi says

    April 29, 2020 at 10:46 pm

    Thank you Anne for the wonderful inspiration, I now believe that, I can also make it with the training by Walter Akolo, that I am yet to join.

    All in all God’s time is the best and with prayers and good training we can all be good writers.

    Reply
  7. Caroline Njue says

    April 24, 2020 at 1:38 pm

    Am really encouraged by Anne, I will soon join you.

    Reply
  8. kigen says

    April 18, 2020 at 3:26 pm

    very inspiring testimony about online work, I just joint upwork and learning the ropes about freelancing.

    Reply
  9. Masika fred says

    April 6, 2020 at 1:22 am

    Am very grateful to here from anne am one who has also tried to find work to do but all in vein and my prayer is always God to grant me work which I can do without interference, so I see my prayer is coming to pass. Am aspiring to be one and I have started the training so my prayer is to serve the clients as they will want.

    Reply
  10. Moses says

    February 19, 2020 at 3:12 pm

    Good Story. It motivates me a lot. I am also willing to go into freelancing. I need a mentor.

    Reply
    • Walter Akolo says

      February 21, 2020 at 4:41 pm

      Hi Moses,

      I’ll be happy to train you.

      See details here https://freelancerkenya.com/article-writing-and-blogging-training/

      Reply
      • Qarowle says

        May 7, 2020 at 3:31 pm

        Would love to hear from you on what this involves regards

        Reply
        • Walter Akolo says

          July 16, 2020 at 2:49 pm

          Start with the tips here https://freelancerkenya.com/money-online/how-to-make-money-online-in-kenya-as-a-freelance-writer/

          Reply
  11. james says

    January 18, 2020 at 9:29 pm

    Helloo how do I chip in

    Reply
  12. Steve says

    December 20, 2019 at 1:44 pm

    Hard work brings great rewards. Keep up!

    Reply
  13. john says

    December 20, 2019 at 11:29 am

    Great work Ann.

    Reply
  14. Faith says

    December 19, 2019 at 7:26 pm

    Wow.!Thanks for sharing you story i wish one day I can reach where you are now.

    Reply
  15. Patrick Mumo Nzilu says

    December 15, 2019 at 7:14 am

    Thank you for sharing your story Ann. It’s really inspiring.

    Reply
  16. Ruth says

    December 3, 2019 at 2:16 pm

    Ann, thank you for sharing your story which has encouraged me immensely to press on as a freelancer. I can relate to some of the things you have mentioned.

    God bless you together with your lovely daughters and together may you all achieve more.

    best regards,
    Ruth

    Reply
  17. Aimie says

    November 22, 2019 at 6:49 pm

    Thanks for sharing your story, Anne. It’s just the nudge I needed to enroll to Walter’s course.

    Reply
  18. Sebastian says

    November 21, 2019 at 7:53 pm

    so inspiring ann…this story reaasures me that it’s possible to earn a living online. Many thanks Walter as well. I hope one day to be featured here…

    Reply
  19. Paul Kimani says

    November 15, 2019 at 6:30 pm

    Forbearance is evident for you to have become a top-rated freelancer. I have started the journey too and God is good there are such selfless people as Walter and Ann ready to give a hand to the willing upcoming writers. Your story has renewed my drive in writing.

    Congratulations, Ann.

    Reply
  20. IRENE says

    November 4, 2019 at 9:38 pm

    I am inspired, I have always desired to make online writing my side hustle. I am willing to try this.

    Reply
  21. Onsmus says

    October 31, 2019 at 2:36 pm

    Dear Ann,
    Thank you for your inspiring story. I have tried this job since may this year but have not gained a lot. I managed to register with a local online market place, they pay as low as 120 per 500 words article and the jobs are not available every day. I am working hard to follow your steps.
    I will appreciate any assistance from you.
    Regards,
    Onesmus

    Reply
  22. Ann says

    October 30, 2019 at 7:30 pm

    Very encouraging experience.
    May the Almighty God keep blessing you for the wonderful work of training others

    Reply
    • Ann says

      October 31, 2019 at 9:17 am

      Thanks Walter for the training.
      Thanks Ann for the encouraging piece. Sharing your lessons with many can help others.
      God bless you abundantly.

      Reply
      • Walter Akolo says

        November 4, 2019 at 12:19 pm

        Hi Ann,

        Always a pleasure.

        God bless you too immeasurably!

        Reply
        • Derick Odemba says

          November 19, 2019 at 10:42 am

          Congratulations Anne. It is inspiring. It is true that Ksh 4000 is a lot of money if you do not have it.

          I scored 64% in my assignment with another freelancing firm and therefore I couldn’t join the program directly without going through training. I needed to have scored 75% to start taking up paid assignments. And I could have done that if I had paid a little more attention to SEO instructions they gave. Moreover, I handed in the assignment in under 3 hrs though there was an option of submitting it within 24 hours. What put me off was not my failure to score 75% in the assignment. Instead, I was discouraged by was their administrator’s inability to answer questions that in my view were administrative. These were questions you would expect her to have answers to at her fingertips. It reflected badly on the firm and this made me lose interest in them.

          I believe I can write compelling articles at present without any training. This is why I am asking Walter to give me a payable job as a test of my ability to write. If I meet his and the client’s requirement, he pays me and vice versa.

          Reply
  23. Kerubo Matara says

    October 26, 2019 at 3:37 pm

    That`s great Ann. I believe in achieving anything provided you have the passion. God bless.

    Reply
  24. Constance says

    October 3, 2019 at 7:18 am

    This is encouraging I also have an account with upwork but gave up when I did my first interview and could not get that first job!

    Reply
  25. Nicholas says

    September 28, 2019 at 9:09 am

    So inspiring, am a beginner. Please lead me on the way to become a successful writer. I will appreciate for any leads. Thank you

    Reply
  26. Stephen says

    September 21, 2019 at 10:13 pm

    Quite inspiring, thanks. This time i gonna make it. I am waiting for Mr. Walter to pick me up.

    Reply
  27. Peter says

    September 6, 2019 at 6:42 pm

    Thanks for Shairing such an encouraging story,all the best

    Reply
  28. Emma says

    September 5, 2019 at 9:38 am

    Such a beautiful story. Thanks for sharing.

    Reply
  29. shinina says

    September 4, 2019 at 3:34 pm

    wow… thank you Sharon this is so inspiring i feel like picking up from where i gaveup from, Walter Akolo here i am coming back coz i had lost hope when the editor kept on telling me to we-write my article.

    Reply
  30. elija says

    September 1, 2019 at 2:58 pm

    u got an inspiring story…..thanks for sharing,am 22 and i think of venturing into writing,please guide me,i did my KCSE last year n am out idling

    Reply
  31. joe says

    August 20, 2019 at 10:19 am

    hi Ann other than upwork account what else one requires to open

    Reply
  32. Eva says

    August 17, 2019 at 9:02 pm

    This is so inspiring… thanks for sharing your story.

    Reply
  33. Dorcus Juliet says

    August 14, 2019 at 7:05 pm

    It’s never in vain. With clear consciousness, hardworking and patience you get a reward. Thank you dear for encouraging.. May God help me join soon.

    Reply
  34. Gakuria Mugure says

    August 7, 2019 at 10:48 pm

    Very motivating. Glad to know. I celebrate you and Walter.

    Reply
  35. Ann says

    August 2, 2019 at 7:06 pm

    Sharon, thank you!

    Don’t give up. You’ll make it! Keep moving forward…

    Reply
  36. Erick Kathenya says

    August 2, 2019 at 2:28 pm

    Any trainer in the house ?

    Reply
    • Walter Akolo says

      August 9, 2019 at 3:10 pm

      Yup! Check out my training details here https://freelancerkenya.com/article-writing-and-blogging-training/

      Reply
  37. Lilian says

    August 1, 2019 at 11:15 pm

    Hi Chep, you have really inspired me. Am thinking of giving it a try and see how it would go with me. Be blessed

    Reply
    • Ann says

      August 2, 2019 at 6:50 pm

      Hey Lilian,
      Good to know that my story has inspired you and now you’re considering going for it. Please go ahead with it already!

      Reply
  38. BEATRICE WANJIKU says

    August 1, 2019 at 10:51 pm

    Thanks Ann for sharing your story,Am encouraged to keep moving,My interest in article writing is growing by day,these are the kind of stories i want to read…

    Reply
    • Ann says

      August 2, 2019 at 6:52 pm

      Thank you Beatrice. I’m humbled by your words. Glad you’re encouraged.

      Reply
  39. Wanjiru Kamau says

    July 31, 2019 at 8:18 pm

    That’s encouraging. I was almost giving up.

    Reply
    • Ann says

      August 2, 2019 at 6:53 pm

      Wanjiru, don’t you dare give up! You can do it…

      Reply
  40. PETRONILA says

    July 31, 2019 at 7:05 pm

    Very inspiring and a challenge to me. Alot of nuggets in between the lines.
    Thanks for sharing your experience.

    Reply
    • Ann says

      August 2, 2019 at 6:53 pm

      Petronila, you’re most welcome!

      Reply
  41. mwangi says

    July 31, 2019 at 8:25 am

    WOW! What an inspiring story

    Reply
    • Ann says

      August 2, 2019 at 6:54 pm

      Thank you Mwangi!

      Reply
  42. Geoffrey says

    July 31, 2019 at 8:08 am

    I believe with the right attitude and hard work, anybody can earn an income from online work. Thanks so much for your inspiring article..am hoping to take the big leap soon!

    Reply
    • Ann says

      August 2, 2019 at 6:55 pm

      You’re right Geoffrey! Thank you so much!

      Reply
  43. Raphael Mokaya says

    July 30, 2019 at 9:39 pm

    An amazing testimony there. A reward well deserved after some years of toil. Indeed with writing, one expects challenges and fruits afterwards. Your perseverance inspires here the more.

    Reply
    • Ann says

      August 2, 2019 at 6:56 pm

      WOW! Thank you Raphael. Am humbled

      Reply
  44. Ruth says

    July 30, 2019 at 9:07 pm

    Hi Chepkoech, i will have to admit that you are a very strong woman. congratulations for your success. i have been really inspired by your story. I am a newbie and hope that will get to your one day.
    Thank you.

    Reply
    • Ann says

      August 2, 2019 at 6:57 pm

      Thanks Ruth for your amazing words. Yes you will get here and even exceed it. Keep going!

      Reply
  45. CONCEPTA MWACHI says

    July 30, 2019 at 7:54 pm

    Very inspiring. As a newbie and green horn, I know I will learn from Walter and people like you as I start this journey. Congratulations for where you have reached.

    Reply
    • Ann says

      July 30, 2019 at 10:15 pm

      Thanks Concepta. Happy to know that my story has inspired you. All the best as you learn and implement.

      Reply
  46. Sharon says

    July 30, 2019 at 4:08 pm

    Very inspired by this. The unemployment, getting laid off, meeting Walter and his informative classes. I am glad I signed up. There is finally order in the process I use to look for online jobs. Walter’s course has taught me so much and im not even half way through.

    I am encouraged to see and I am expecting burn out, discouragement and negative feedback from clients at least I know I am not alone.

    Reply
    • Ann says

      July 30, 2019 at 10:18 pm

      Thank you Sharon. It’s been a journey and a half for me. Glad you’re learning something from this. All the best!

      Reply
  47. Emma Seshoka says

    July 30, 2019 at 12:22 pm

    I’ve had similar experiences, the first article rejected can be a heartache , but persistence is key. thanks for inspiring us to keep going.

    Reply
    • Ann says

      July 30, 2019 at 10:21 pm

      Thanks Emma for your kind words. It’s true that persistence is important if one has to be successful in what they do.

      Reply
  48. Ann says

    July 30, 2019 at 12:03 pm

    Thank you Cosmos. Great to know that you can identify with some of the things I’ve mentioned.

    True, I’m not where I was a little over a year ago. Thanks to this awesome opportunity and the support I got from mentors like Walter. It’s been a real journey.

    Reply
  49. Laban says

    July 30, 2019 at 12:00 pm

    Incredible! what a mind awaking piece!! I’m motivated. It has given me hope. Thanks chepkoech.

    Reply
    • Ann says

      July 30, 2019 at 10:23 pm

      Hey Laban. I’m happy to know that you’ve been inspired. Thanks!

      Reply
  50. Emma says

    July 30, 2019 at 11:20 am

    Very inspiring. It reminds me that we can achieve anything we put our minds to.

    Reply
    • Ann says

      July 30, 2019 at 12:05 pm

      Emma, thanks! I’m glad my story has inspired you.

      Reply
  51. Catherine Nyorani says

    July 30, 2019 at 11:09 am

    Thanks for sharing your story Ann.
    I’m always inspired by such life experiences. All the best as you continue pursuing higher levels.

    Reply
    • Ann says

      July 30, 2019 at 10:25 pm

      Hey Catherine. I appreciate your kind words. Glad that you’ve learnt a thing or two from my story.

      Reply
  52. Damaris says

    July 30, 2019 at 10:51 am

    Many thanks Chepkoech for sharing your story. It is inspiring!

    Now I know I just need to push harder.

    Reply
    • Ann says

      July 30, 2019 at 10:28 pm

      You’re welcome Damaris. Glad that you’ve found my story inspiring. Keep pushing hard!

      Reply
  53. CHARLES SIFUMA says

    July 30, 2019 at 10:47 am

    Awesome piece. Congratulations Chepkoech and great work Walter for your training course; you’ve impacted positively to the lives of many people both locally and internationally. We also thank the most almighty. God bless you

    Reply
    • Ann says

      July 30, 2019 at 11:55 am

      Thank you Charles for your kind words.

      Reply
  54. Edwin Kirui says

    July 30, 2019 at 10:35 am

    Incredible! What an inspiring piece! Surely as said, hardwork, persistence, and self-believe will take you places mom.

    I can relate to a few of the experiences. Though am still in the struggling part trying to work my way up.

    Thanks for the great encouragement mom.

    Reply
    • Ann says

      July 30, 2019 at 11:56 am

      Thank you Edwin. I’m glad that my story has encouraged you

      Reply
  55. Philemon says

    July 30, 2019 at 10:19 am

    Ann, that is a very inspiring story. I have known you for a long time and true to your story, you have surely gone through many challenges. Your writing on Facebook is always to the point of a counselor. I read your articles.
    Ann, many youths are not aware of such online opportunities and are busy looking for formal employment. How I wish they can reach you for advice on the very many online opportunities available out there.
    I do wish you well and God blessings. Go on.

    Reply
    • Ann says

      July 30, 2019 at 10:33 pm

      Thanks a lot Philemon! It’s true there numerous opportunities online that people can take advantage of.

      And yes, at least you know a bit of my story… The thick and thin…hehe. God has been good.

      Reply
  56. Trevor says

    July 30, 2019 at 10:12 am

    A really inspiring story

    Thumbs up

    Reply
    • Ann says

      July 30, 2019 at 10:34 pm

      Thank you Trevor for your compliments!

      Reply
  57. Boniface Kisina says

    July 30, 2019 at 8:54 am

    What an inspiring story by Chepkoech. I like the way you’ve taken us from your past history to starting a new career in freelance writing. This gives the post a personal feeling.

    However, you should know that freelance writing is a business like the ones you had opened before. Hoping that you learned from the mistakes you made with the other businesses that failed and that you won’t come to repeat the same mistakes again.

    Reply
    • Ann says

      July 30, 2019 at 11:58 am

      Thank you Boniface. It’s true that freelance writing is a business. And yes, the lessons I learnt from the failed businesses form part of my experience today.

      Reply
  58. peter says

    July 30, 2019 at 8:30 am

    Such an inspiration, truly the sky is the limit.

    Reply
    • Ann says

      August 2, 2019 at 6:59 pm

      True Peter. Thanks a lot!

      Reply
  59. Keneth says

    July 30, 2019 at 8:00 am

    Such an encouraging Story. Despite all odds and the hardships you encountered you made it this far. Keep shining and make it even bigger and better

    Reply
    • Ann says

      August 2, 2019 at 7:00 pm

      Thanks a lot Kenneth for your encouraging words!

      Reply
  60. Cosmos says

    July 30, 2019 at 7:31 am

    Wow! This one rings a bell. How you met Walter part of it; the training part of it; the discouragement during training; the burnouts and lowballing from some clients. All are storms freelance writers weather in their freelance journey. It’s an encouragement that you’re in a better position than where you were when you started.

    Reply
    • Ann says

      July 30, 2019 at 2:48 pm

      Thank you Cosmos. Great to know that you can identify with some of the things I’ve mentioned.

      True, I’m not where I was a little over a year ago. Thanks to this awesome opportunity and the support I got from mentors like Walter. It’s been a real journey.

      Reply
  61. Bonnke Arunga says

    July 30, 2019 at 6:42 am

    Congratulations for the good work! Your story is encouraging.

    Reply
    • Ann says

      August 2, 2019 at 7:01 pm

      Thank you Bonnke!

      Reply
  62. Jane says

    July 30, 2019 at 6:32 am

    Wow. I’m encouraged. I’m still learning the ropes and soon my story will be here. Congratulations chepkoech.

    Reply
    • Ann says

      August 2, 2019 at 7:02 pm

      Jane, I’m happy the hear that. All the best!

      Reply
  63. Sharon chepkorir says

    July 30, 2019 at 6:12 am

    Wauh, wonderful; Walter trained me, was almost giving up but when I read this I get encouraged, I believe I can still make it too. Thank you Walter, God will reward you abundantly for changing the lives of many.

    Reply
    • Ann says

      August 2, 2019 at 7:08 pm

      Thank you Sharon!

      Don’t give up! Keep moving forward…

      Reply

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