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Freelance Writing: From Zero to a Decent Side-Hustle

Disclosure: Some of the links in this post are affiliate links. This means that, at zero cost to you, I will earn an affiliate commission if you click through the link and finalize a purchase.

Content writing is a goldmine!

How best can I prove it other than sharing my personal experience?

If you are a beginner, roll up your sleeves and put in the work. You can succeed in freelance writing.

Gurus reading this should honestly share feedback on the comments section.


I’m still hungry to learn more. That’s how writers grow into valuable professionals.

Long Story Short

Insider Note: I work a full-time job. And freelance writing has morphed into my very profitable side hustle.

Reality Notes:

I’ve done cold pitching and gotten paid for my effort

Ever been paid with crypto for your content? Read on. It’s a reality.

Cold fact: I’ve severally fallen into the hands of very smart scammers. Stay tuned to get my insights to sniff a scammy job or client.

Now, on to the Long Story

I first heard about online jobs in 2013. Eager to satisfy my curiosity, I opened an account with PeoplePerHour. Green and bubbling with expectations, I threw in a few crappy bids.

I got no responses and quit altogether.

By then, I was chasing fourth-year units for my Bachelor of Commerce undergraduate degree.

It seems lady luck had smiled upon me from earlier on.

All my days through university coincided with a smart internship opportunity. Shsssh! It helped me pay the hefty varsity fees. Thanks to my earlier course, I’m a CPA-K.

I graduated in December 2014. And still, luck lurking along, the board decided to pull me into management – finance.

I love the tasks I do daily. But I happen to love writing more passionately.

Bouncing Into the Freelance Writing Scene

Human beings never get satisfied easily. So, in 2016, I found myself with an Upwork account. No contracts. No reviews. No earnings. Upwork is a rebrand of what was previously oDesk and Elance.

Upwork is competitive. It would give you 60 free connects or credits monthly to apply for jobs.

I wasted the entire 2016. I was lazy and lacked motivation. Right now, it only gives you 20 free connects when you join. After that, you have to buy connects.

It reminds me of one famous quote by Dr. Geoffrey William Griffin, the founding director of the renowned Starehe Boys Center: 

Happy are those who dream dreams, but are willing to pay the price to make them come true! 

– Dr. Geoffrey William Griffin

My 2017 was also slow until the government of Kenya, through a partnership with the Ministry of ICT and Rockefeller Foundation, announced the Ajira Digital Programme.

I blocked five days off work to attend the training with renewed interest.

I was a step ahead of most trainees – with an empty Upwork account. The downside, I had nil reviews, contracts, and earnings.

The government did its part and left trainees wobbling around with pure hype that they called mentorship.

Most ditched the online work idea. In my cohort, out of 143 trainees, I guess only a paltry 15 were serious.

There were coders, web developers, transcriptionists, and writers.

I guess I was none of those serious 15! But it was a turning point.

Editor’s note: Ajira used to be crappy when starting, but it’s gotten much better. If you’re new to online work, you can join their free courses.

Getting My Feet Wet and Facing the Reality

As a hopeful greenhorn, I got a client in August 2017!

Allow me not to share how I crafted the winning bid, but there was an Upwork contract reading $330 in escrow.

So, without proper knowledge on how to handle such a contract, I lost it! I was sad. So sad.

Here’s How I Lost It

Two weeks into my first Upwork contract, my draft was ready. That was one brilliant eBook about everything you need to keep macaws. It had around 90 pages.

What was my fatal error? Plagiarism!

Two weeks on with the client, everything was fine. I rate the client’s team as one incredible duo, though I failed them. They sent screenshots showing evidence of plagiarism.

I protested with my greenhorn prowess, dragging myself into plagiarizing even MORE!

Did I know what Copyscape was or how it was used?

A big NO!

The most painful part? I lost the entire book project! But truth be told, it was all my fault.

Accepting the Truth – In Fact, it’s What Sets You Free

I hated Upwork for around 3 months. After the hazy three solid months of hate, true and cold hard facts reemerged.

Hmmm, it was all my fault. I accepted this. It felt better with time.

Back Into Shape to Pitch and More Failures

An inner voice would still tickle me, faintly though:

You can write

You can write well

You can write wonderfully

The more I heard the voice, the more I would research on freelance writing. Here’s what I did.

I subscribed to Walter’s free emails for freelance writers. Those free emails are jam-packed to ignite, inspire, and build you for the better. They help both newcomers and veterans.

I learned that cold pitching works wonders

I eventually enrolled in Walters’s premium training. I did this hastily. Remember I have a day job. This premium bit is handy at helping guys to earn and avoid scammers.

Walter is one guy who’s helped transform the writing industry in Kenya. Just check out his Facebook page, where he shares an endless string of insights.

Uniquely, Walter inspires, educates, and virtually transforms.  Online followers (me included) feel the inspiration, which seems limitless.

Most of his trainees would bear witness that Walter is a game-changer and one selfless guy. If you listen and do what he says, you’ll be forever grateful. I’ve not had a single regret following Walter since 2017.

Getting the Necessary Tools

I was armed. A course at hand, an Upwork account, and a book that changed how I bid – How to get Clients Say Yes by Walter Akolo.

Fast forward, I got a new Upwork client! I delivered 700+ words and got my pay plus an excellent rating.

That really helped me secure my account. Upwork bans people who apply for too many jobs without getting hired. Here, I had both a client and a great review.

There’s so much opportunity for writers online. Well, some of it is crappy, to be honest. Would you blindly work for any client? No. And no again.

Go out there and know what niche you can deliver best on, and narrow down to it. You’ll be amazed by the masterpieces you’ll be producing.

I’ve, over time, gained significant expertise. I’ve gotten great clients in the crypto/blockchain niche. Honestly, I had to stick to my values to reject one client who wanted me to write content promoting porn and nudity!

Writing proposals and pitching is funny. Get it from my experience. You can get hired in a record five minutes, or it can take weeks.

But the bottom line is that you should create value and have evidence to show it. That’s what gurus refer to as social proof.

With time learn how to balance your workload with your job application frequency. Ensure every client’s need is well met.

Ever Cold Pitched and Won a Job?

Yes. I count myself a lucky guy. In 2018, I landed my first job from a cold pitch. Here’s exactly how I did it.

After looking at strings of online tutorials, I managed to launch my blog.

Sidenote: If you are like me, loving to break and make things, you can master WordPress, HTML, and CSS. With the right effort, this can be your cup of coffee.

My pitch got accepted. The client settled at $62 for 600 words. It’s relatively low but, honestly, significant for that first time.

Pitching is a numbers game. Master your niche and walk the lonely yet rewarding trail.

Starting on online work platforms is an excellent way for starters to get their feet wet on the trade.

It would help if you were not faint at knocking into inboxes of prospects. In case you feel none of the prospects is responding, follow the learning, unlearn, and relearn hacks. Rinse and repeat.

For cold pitching, I recommend you follow handy tips from the WriteWorldwide team. But more closely, follow another guru from Nigeria – Bamidele Onibalusi. One Jawad Khan, based in Pakistan, credits his success to the Bamidele challenge.

Ever Fallen Into the Hands of Ruthless Scammers?

Getting scammed is painful. If it’s never happened to you, then you may never know how it feels.

I’ve worked with scammers. They conned me but left me with handy life lessons.

Your content remains your property until clients pay for it as prior agreed.

Writers should never fear scammers.

Indeed, it breaks your motivation, but rise again and win with other valuable clients.

Spike Wyatt has a fantastic free eBook with tips on how scammers cloth their adverts around different online platforms.

Download and read it. Thank me later.

Ever Been Paid in Bitcoin?

Yes, I have. Fearfully though.

I wrote a piece for a client, and they had promised to pay in Bitcoin.

I was skeptical, but I walked with caution. Not all clients are scammers.

Again, I went into the task, expecting low pay, but already up to some form of surprise.

I’d read about Walter’s trainee who was once paid in Bitcoin.

When my client requested my Bitcoin wallet address, I did some quick googling and settled for an Electrum wallet. I ran the installer and forked out the address to him via Telegram. Walter recommends Paxful as a great wallet provider and Bitcoin marketplace.

In my case, I knew crypto works, but I doubted it till it actually worked for me. We all have those first-time doubts




Don’t we?

Funny Bit

My client did pay in Bitcoin.

But it took me two months to verify this.

Here was my problem; the Electrum wallet could not connect via Firefox or Chrome. I had to run another browser known as The Onion Router (Tor browser). This connected in seconds.

I verified the Bitcoin in my Electrum wallet. Huge credits to my googling skills and the Reddit guys who posted the helpful string.

Note that it doesn’t have to take you this long to cash out your bitcoins. You can get paid today and sell the bitcoins in a few minutes via marketplaces like Paxful.

Get Your Education Passionately and Pursue Your Interests Ruthlessly

Guys, you can earn online. Never stop learning and implementing.

If you are chasing tertiary education, go for it with all you might. And if you have the knuckles to merge your job or studies with freelance writing, constantly sharpen your writing skills.

So far, I’ve been doing freelance writing as a side hustle for years. I love the experience.

You can do it too. Start now.

Never shy away from taking a free course. Most free nuggets are just what you need and are all over the internet for you to take up.

Premium courses from established and proven professionals help boost your success. If you have some coins, pay up for something you find useful.

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James Maina is a freelance writer and blogger for hire. He's a crypto-assets and blockchain content marketing specialist. You can check out his portfolio here.

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Hi. Thank you for this piece. my story is almost similar, as I started and stopped with Upwork. I have made the decision to try again and I am currently undertaking Walter’s Premium training Course. It is very insightful.

Grace Gatoto
Grace Gatoto

Thank you James for an insightful piece. This was indeed helpful and as a writer, I will be sure to implement your tips. On another note, I agree that Walter is a game-changer in the industry.

My trainer, who is excellent by the way, was Walter’s trainee and so I consider myself his student by default.


Great insights! Need to do more content like this.


Hey James. I really am interested in doing the job but the limitations I have is that at the moment I can’t raise the fee. How can I be helped become one of your family??

Reply to  John

Well John, Don’t worry.

Simply start with what you have at hand. On this site, subscribe to the free emails and you’ll get handy free tips before you can raise the fee.

Never limit your options, start with the freebies here.

All the best


Hello..This is really an awesome encouraging piece.Though am a newbie, I hope and believe that I will rise to maximums soon.thank you

Reply to  John

Hi John,
The sky is the limit. Put in the hard work and you will make it.
All the best.


I must say am inspired. I have tried academic writings but I didn’t sail through. I was devastated and broken having bought an account which was suspended before it paid off. However, my hope is rekindled and am planning to start training with Walter come next week.

Reply to  Ann

Hi Ann,
Thank you for reading through and feeling energized.
Starting out with Walter is a great move. One tip – take keen note of the points in that course and lean towards taking action. Steer away from procrastination.

Evans Kibet
Evans Kibet

Congratulations Maina, It would be good if you good mentor other young people. From ‘looking for jobs’ to ‘creating jobs’

Reply to  Evans Kibet

Hi Evans,
Our doors remain open

Peris Otieno
Peris Otieno

Hello James,
Thanks for all the advice. Full of insight really. You guys are truly selfless.
A quick question, the link to Frank Otwori’s strategy leads to the transcribers group as well? Should it not lead to his strategies, I was really interested to learn the tips. Or is there another way to access that blog? Please double check and let me know.

Walter Akolo
Reply to  Peris Otieno

Hi Peris,

I agree James did an amazing job.

Frank posted that strategy on the transcribers’ group. You can join and check it out.

You’re also free to inbox Frank Otwori on Facebook and discuss further on it.



Thank you for the advice.

Lucy Njoki
Lucy Njoki

soo inspiring and amazing, love your work,keepit up. Looking forward beeing like you one day. Am now motivated to start traing without fear.

Reply to  Lucy Njoki

Hi Lucy,
Thanks for finding the post inspiring. One take-home point for you: One great Kenyan once said; “-Happy are those who dream dreams, but are willing to pay the price to make their dreams come true.”
Hopefully, you’ll find both sense and inspiration from that, and you’ll sure excel. Good luck in your aspirations.

Anthony Njeru
Anthony Njeru

Thanks a lot James for the awesome and inspiring piece. I must it is simply priceless. I’ve been reading Walter’s posts and they are equally inspiring.

It’s very encouraging especially to note that as newbies we go thru the same experiences but the difference comes in never giving up. Thanks for lifting me to a another level. Be blessed

Reply to  Anthony Njeru

Welcome, Anthony, and great you found some inspiration from the post. Actually, it’s great if you already receive the emails that Walter sends to subscribers. No doubt, I too have gotten inspiration from the emails/posts.

I agree strongly – the difference comes in by persistence, never giving up. Of course, no success comes easy, and hopefully, you’ll find the inspiration to help you all along. Also, sharing experiences is one wonderful way to inspire others. We are all human and none of of us was born knowing it all.

It’s the little bits of inspiration, efforts and willingness to transforn that changes everythinng.


Thank you for the inspiration. I really wanted to take walter’s course but currently I don’t have the cash though am planning to enroll later when I get the money. My question is, should I just move forward and try freelancing with the little knowledge I have and the advices I might get from the internet or I must wait till I get money and take the course. What is your advice.
Thank you

Reply to  Usama

Hi Usama,
Great that found time to read through and you found inspiration here.

First, I’d recommend that you take Walter’s course.
And now that you do not have the money, there’s a solution.:
Take my recommendations and thank me later.
Walter offers a mini-course, and the beauty is, it’s free for you. Usama, enroll for that.
Do not delay your freelancing career any longer.

The biggest difference between a winner and a loser is that losers brag about how much they know, while winners roll their sleeves and get to work implementing the little they know.

The truth is, the free course is good for you. If you implement the notes right, you can bag a client and that’ll surely enable you to pay for the course.


Very encouraging to read this in the morning.


Hi Emmah,

Thanks for creating the time to read through the post.

In most occasions, I find reading a motivational post in the morning a great deal.
Not only does it uplift your objective outlooks and inspiration, but also allows you to grasp the key points much better.

Imagine reading a great post or two a day, it will change everything in life in the long run.


Wow.. really inspiring. One question, how do you juggle your day job, writing and family?

Reply to  Fred

Hi Fred,
Good question here and thanks for finding the post inspiring.
I find writing easy to juggle around with my day tasks and the family. First, I handle all my writing via GoogleDrive. All my clients have a distinct Googlefolder. And in each folder is a Work-in-progress file, while cmpleted and delivered files are moved into a folder named completed. It helps me work on the go. If I have a free spell at the workplace, we can chat with colleagues as I type on a GoogleDoc. There’s no worry to save and other distractive stuff.

If I have an Idea regarding a post, I just do the outlines and continue populating the paragraphs with time.
However, If I have substantial backlog with editing, I may slot that on a Saturday when I’m free from weekday tasks. Ideally, it’s putting your free times to good use. For me,it’s writing.

If you’ve your day schedules cut out, you can afford to handle day tasks rather comfortably but speedy enough to give you lapses to brainstorm on client search and writing tasks.

Also, I recognize that I do too much, and sometimes, I just do not push myself to hard. I have my schedules and if I do some good drafting during the day, I can afford to sleep all night to freshen my mind.



“Thengeu mundu wa nyumba” As a begginner you have really inspired a lot, hope that me too one day will have testimonies as you do.

Reply to  Josphat

Hi Josphat,
Thanks for reading. Glad you found it inspiring.
The sky is your limit.


This is really inspiring I just love it, good job James and thanks for the inspiration

Reply to  Roselyne

Welcome Roselyne and glad you found time to read through and find inspiration.

Paul Wall
Paul Wall

This is marvellous, fantastic, and inspirational, James.
Currently, I’m earning peanuts from freelance content writing, but I’m trudging forward steadily.
Thank you for sharing this.

Reply to  Paul Wall

Thanks Paul Wall,
You are a step ahead if you are already earning something. Keep your focus towards leveraging your client base. Ideally, offer more of quality in place of quantity as well as narrowing down to a niche or two.

Gerald Wamuhu
Gerald Wamuhu

This is more than encouragement it’s like real life being offered on a silver plate
James thank you so very much.

Reply to  Gerald Wamuhu

Hi Gerald,
Thanks you found the post encouraging. Actually, most smart stuff is free online. But you have to do the smart weigh-lifting by selecting what’s useful for you and most importantly, putting it to good use.


Thanks James for this encouraging write up.

Reply to  Tina

Hi Tina,
Thanks you found it encouraging


So moving, I’m a beginner hopefully I will be a guru like Walter soon

Reply to  Naftal

Yes Naftal, the whole idea is to figure out the bigger picture. And appreciate the little steps with efforts towards the bigger goals. The sky is your limit


Just like am learning how to balance the two.

Reply to  Peris

Hi Peris,
Firstly, it’s a matter of focus.
Secondly, set your targets and harness efforts towards achieving them. Sometimes, it may be daunting, and that is where focus and targeting helps you remain on the course.
Lastly, always learn a trick or tow each day and you’ll improve with the lapses of time


Wow…l feel inspired and encouraged.

Reply to  Liz

Hi Liz,
Thanks you found this both inspiring and encouraging.
Hopefully, you’ll be able to build up on the inspiration t help you closer to your ideal online business.

Ekesa A
Ekesa A

What a motivation, thank you for the encouragement.

Reply to  Ekesa A

Welcome Ekesa, and may the information in the post inspire you towards your dreams..


So inspiring. I am encouraged to continue pressing on until I bag clients. Thanks too for the links.

Reply to  Becky

Welcome Becky,
If you’ve not had clients yet, keep up inspiring yourself and implementing most tips online. Most writers have a great desire bag clients but fail to overcome the challenge with creation of great/mouth-watering samples.

Take a slower step, write up posts in free online portals like Linkedin Pulse, Thriveglobal and

With samples online, you stand better chances bagging clients – you already have something to show and impress prospective clients who can pay for your writing.


Good motivation to start the week and month. Cheers

Reply to  sarah

Yes Sarah, I often find it inspirational reading a motivational post or two as I kick of my day.
Great that you’ve found something to inspire you through the week and month in that order.
So you can close the year big. Cheers too!

Tobias Kumwenda
Tobias Kumwenda

Awesome nuggets in here. Thanks James.


Sure, Thanks Tobias Kemwenda


Wow. I get motivated everytime I read stories like this. I can actually make it!

Reply to  Margaret

Welcome Margaret, and let the motivation take you to higher levels

Reply to  James

I will let it.


wah so motivating

Reply to  Benedict

Thanks for this

Reply to  Sera

Welcome Sera. Thanks you found time to read the post.

Anngladys Gichuhi

Great stuff!! Keep it up!!


Thank you Ann for creating the time to read, and Karibu!


Thanks alot James that’s so insightful. I will now put in more effort and be serious to look for my nitch. I only knew writing to be about story telling and theoretical yet am a person of science and facts maybe science fiction I can dig. I hope I find something along those lines at upwork

Reply to  Tess

Tess, with science, you have a solid background under your belt. Take your search to another level and I believe your efforts will pay off with time.

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