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.

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.

Similar Posts