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Should you Quit Your Day Job to Start Freelance Writing?

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Do you have a passion for writing but feel trapped in your current job? 

If yes, you are probably worrying about your future if freelance writing doesn’t work out. 

You might be wondering:

  • Would your employer hire you again?
  • What would people think of you if you left a well-paying job to pursue freelance writing?
  • Will people accord you the same respect?

Relax, I know how it feels. I have been there.

I quit my day job to start freelance writing but failed terribly. I went back to my day job and quit again after two years. This time, I was prepared and did not regret it. 

Let me tell you how it happened. 

The Pandemic Came Knocking

I was working in a food processing factory that sourced some of its raw materials from countries where the coronavirus pandemic had hit first. The virus spread so fast that governments had to restrict movement in and out.

Our factory could not operate without all the necessary raw materials, so it stopped operations and let go of 75% of its employees.

Luckily, I wasn’t one of them.

I felt I should have been laid off as the retained employees celebrated.

Strange, right?

Let me explain why. 

I loved to Write From a Young Age

I was always on top of my class in writing compositions (a test used to assess creative writing in primary school). 

The teacher would always read out my compositions to the entire class. 

I even kept a physical journal (I still do, but a digital one).

I dreamed of writing a book someday.

Fast forward to 2017, I joined a popular savings-related Facebook group. 

In the spirit of helping one another to save more, members talk of marketable skills that can supplement your income. It is here a member mentioned online writing as one of the skills. 

I was excited because I always loved to write. I immediately fell in love with online writing, even though I didn’t know what it entailed. 

In subsequent posts, the name Walter Akolo became synonymous with online writing.  

I followed him on his Facebook pages, joined his groups, and subscribed to his emails, as recommended by members of the savings group. In a short time, I had an idea of what online writing was all about. 

My job was very demanding, and I struggled to start writing while still at it. I would work 12-14 hours a day. I only found time to write my journal since I could do it on the phone.

Back in 2020, during the pandemic… 

I Enrolled in Walter’s Course

My zeal to become a full-time freelance writer was at its peak. That’s all I wanted.

I quit my job before the first case of the Covid-19 was announced in Kenya (12th March 2020).

I knew everything to do with freelance writing, or so I believed.

In Walter’s emails and posts, he kept saying, “No matter how much you learn, and from who, if you don’t implement it, it’s useless.”

I thought I would prove him wrong. I had followed him and other experts for three years and had all the knowledge needed to succeed in freelance writing.

I decided to write my first article. 

Even without hearing from someone else, I could tell it was terrible.

Walter was right. If you don’t practice what you learn, it’s a complete waste of time.

Enrolling in his Complete Article Writing Training was the only way to skip trial and error. 

After the training that took one month, I realized I could have probably wasted the entire year doing almost everything wrong. It saved me from plenty of hurdles.

I scored 55% in my first test article and 85% in the second review. The editor’s feedback was constructive.

I got my first job with a Kenyan client the week I finished training. Unfortunately, the client was untrustworthy and scammed me.

I Went Back to My Day Job

A friend I had made in one of Walter’s Facebook groups referred me to his employer, who was hiring then.

We worked together for two months before he disappeared with my money. 

Why did I fall victim, yet the training taught me how to avoid scammers?

As I said earlier, Walter insisted, “Faith without action is dead.” He trained me to avoid scams, and I had to implement the lessons.

I started noticing the client’s red flags in the first week of working together, but I was hoping he couldn’t scam me since he kept posting Christian quotes on his WhatsApp status.

Something else, he kept postponing the payment date. He’d say he’ll pay on a specific date but would push it a week further with vague excuses. 

After two months, I was completely broke and could barely afford one meal daily.

One consistent message Walter kept posting (and still does) was that it was a bad idea to work with one client only because you’d have to start from zero if they bailed on you.

I failed to implement this lesson and paid for it dearly.

The biggest mistake of them all was quitting my day job without a plan. I’ll come to this later in the post.

Before I decided on the next step, a reputable person posted on one of the popular freelance writing groups that there was an AI writer called Jarvis (now Jasper) that had come to take up all our jobs. He even said he had stopped hiring writers. 

As a newbie, I couldn’t tell real from fake information, so I believed the person.

That’s how my freelance writing journey ended. I didn’t see how it was possible to compete with machines.

Luckily, governments had lifted most of the pandemic restrictions, and my former employer resumed operations. I went back together with the laid-off staff. 

I Worked For Two Years and Quit Again

I only went back to work because circumstances forced me to. Otherwise, my calling was in freelance writing.

So, I worked for a short period as I restrategized and figured out how I’d overcome the challenges I had previously experienced if I restarted my writing journey.

During the two years, I updated myself with industry trends and everything that happened in the writing world.

In August 2022, I quit my job for the second time. But this time, with a plan of navigating the industry if things didn’t go as planned. However, I had done the necessary research to ensure I’d succeed.

Everyone who takes Walter’s training gets lifetime access—meaning they retain access for as long as it’s available online, even if it’s years after the payment.

I went through it and was sure I was ready for the market.

My job was so demanding that I couldn’t even spare thirty minutes to write a few words. The only way to start was to quit altogether. But don’t forget, I was more prepared, and my odds for success were higher.

I Got My First Job

In one of Walter’s groups, Remarkable Freelance Writers in Africa, a challenge was introduced where new writers could post their articles for review.

I posted mine, and more than seven potential employers contacted me. I engaged them all and settled on three. I was not ready to make the mistake I had made before of working with a single client.

I fired one in a week and continued working with the two. We worked together for three months. I felt I needed to work with clients who’d pay me better. 

Over the years, I learned how to acquire high-paying clients. The only problem was that I never implemented any of the methods. 

I started looking for high-paying clients while working with my Kenyan employers.

Upwork and Fiverr were not my cups of tea. I never spent much time on them, even though many of my newbie friends seemed to have found success in them.

My primary way of getting clients was through LinkedIn. 

In the two years I returned to my day job, I had many potential employers asking for my services. Ironically, my Linkedin account was dormant, meaning they only found me through a search.

What if I became more active on LinkedIn by posting valuable stuff and engaging with other people’s content? Could I get more clients seeking my services?

Two weeks after posting content related to freelance writing, I got a client. She offered me a full-time role working less than 20 hours per week with an $1100 monthly salary. 

I work with other clients I have found on LinkedIn. In fact, 90% of my clients have come from LinkedIn. Surprisingly, if you do things right, clients reach out to you more times than you reach out to them.

I’ve also worked with clients I got from Reddit and Medium (Yes, Medium. I was as surprised as you are, too!).

I promised to tell you something about quitting my job without a plan. 

Don’t Quit Your Job Without a Plan

When I quit, I assumed everything would fall into place because I knew everything about freelance writing. 

I was wrong.

I should have ensured my life would go on without hitches for the next few months, even if I didn’t succeed as fast as I expected.

Here’s what you should do before you quit your job: 

Ensure you Know What Online Writing is All About

Walter or any other trainer will only teach you how to write well, NOT how to write.

Before training, search what online writing is about and what to expect. Trainers will teach you how to:

  • Get clients
  • Structure your writing
  • Avoid getting scammed
  • Dos and don’ts of online writing

But they will not teach you:

  • How to write (that’s the job of your nursery school teacher)
  • When to write (It’s upon you to organize your time)
  • What you need to start writing

For example, before you pay for training, you should know that you need the following:

  • A laptop
  • Good internet connection
  • Basic English writing skills

Check everything to ensure you don’t quit your job prematurely because you may make a regrettable mistake, just like me. 

Have an Emergency Fund

If your job is demanding like mine was, and you can’t multitask, then it’s advisable to set aside some money to last you a few months if your writing career doesn’t start on a high.

I’d recommend having money to pay your bills for at least six months. 

Depending on where you get your training, you may spend a month or two while still learning. 

You may spend another month or two before you find an employer with consistent work. But it’s unlikely you’ll spend more than two months if you implement what you learned.

However, it depends on your ability to comprehend what you were taught and your implementation speed. That’s why some people succeed faster than others. I have a friend who got a high-paying client while still training. 

Have Some Motivation

I’m in many freelance groups where some members advise aspiring writers to quit their jobs because it’s easy to make money doing online writing, which is not true.

Freelance writing requires effort and hard work like any other job. It’s not a get-rich-quick scheme, as others put it.

Unlike in most day jobs, where you get paid on Sundays, public holidays, and other days you don’t report to work, no one pays you for online writing when you don’t complete a task. In other words, you only get paid for what you do.

So, if you want to become a full-time freelance writer, you should be motivated to become one. It can be:

  • You want to diversify your skills
  • Looking for financial stability
  • More freedom 
  • You want to leave a toxic workplace

Make sure you have a driving force pushing you to change careers. 

Ensure you Have a Client Base

Not everyone’s job requires them to work for long hours a day. Some people have flexible working hours that allow them to write part-time.

If you are one of them, you are better placed.

You can start learning by following industry leaders and implementing everything you learn. If you don’t want to take the longer route, you can invest in training to avoid common hurdles.

In many of Walter’s posts, he recommends quitting after matching your writing income to your job’s salary. This way, you won’t need to downgrade your lifestyle to fit your needs.

Once you have enough clients, it’s time to write that resignation letter. 

In Conclusion

It’s okay to quit your day job to start freelance writing, but you need a strategy to keep going if it starts slowly.

I failed to create a plan and don’t want you to do the same. 

I can’t call myself successful yet, but I’ve made tremendous strides to ensure I stay on the right track. I also earn way more than I did in my day job.

Implementing what you are taught is another critical aspect to prioritize in freelance writing. If you learn without implementing, you will not achieve any success. You’ll have only yourself to blame if you don’t implement what you know.

It’s not mandatory to take up training. Many writers have made it by teaching themselves. The only problem is that they took so long to get there. 

Why should you go the trial-and-error way for a year or more when you can do the same for a month? Investing in training will save you time and help you avoid costly mistakes. You will also start earning much sooner.

You’ve probably heard about ChatGPT, an AI writing content from scratch. I bet you’ve heard it’s here to replace writers, and you may feel unmotivated to start.

Before you listen to such negative news, remember one of the reasons I had to go back to my day job was because an AI, Jasper, was said to replace writers.

That didn’t happen. 

On the contrary, many writers raised their rates because human-written content is unmatched.

Aspire to continuously improve your craft to stand out from “AI-level” writers.

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Isaac Kimaru is a talented freelance writer who crafts compelling stories that resonate with his readers. With experience writing across various industries, Isaac has honed his craft and developed a unique writing style that captivates his audience. Connect with Isaac on LinkedIn to learn more about his writing journey.

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Beatrice Kapei
Beatrice Kapei

Woow thanks Isaac ! Such an inspiring article,I still toying with the idea of freelance writing but I must say your story has motivated me & I God willing I will sign up for the course,your advice is invaluable !

Reply to  Beatrice Kapei

I’m honoured to hear my story inspired you, Beatrice! Enroll for the course and take action!

jameson kamau
jameson kamau

Thanks Isaac for this great inspiring story. I have always wanted to do freelance work on a full time basis, and this has once again triggered my ambitions. I wanna take the course from walter. Thanks for the great advice

Isaac Kimaru
Isaac Kimaru
Reply to  jameson kamau

You are most welcome, Jameson! The only thing you need to do is start. Build habits, and you’ll be steps ahead in a short time. Walter’s course is very detailed and beginner-friendly; go ahead and take it. You have my blessings!

cynthia muimi
cynthia muimi

Informative and inspiring.

Isaac Kimaru
Isaac Kimaru
Reply to  cynthia muimi

Thank you, Cynthia!


Thanks so much Isaac, this is so inspiring. I feel like this article is directed to me.
I am happy I read this real story. be blessed

jameson kamau
jameson kamau
Reply to  caroline

This article is directed to me too

Isaac Kimaru
Isaac Kimaru
Reply to  caroline

Welcome, Caroline!


Oh! such inspiring content…Some spirit uplift! thank you.

Isaac Kimaru
Isaac Kimaru

Glad to hear you found it inspiring. Thank you!


Thank you Isaac for that inspiring article. It is very encouraging to read real stories.

Isaac Kimaru
Isaac Kimaru
Reply to  Faith

Thanks, Faith, for the kind words and for taking the time to read. We all start somewhere.


Truly inspiring.

Isaac Kimaru
Isaac Kimaru
Reply to  Sammy

Thanks for the kind words Sammy!

Mustafa Abdulhussein
Mustafa Abdulhussein

Thank you Mr. Isaac Kimaru for your valuable post. I too have a dream of writing full-time. But first I need to get some part-time work which despite my best efforts I have failed to get. Currently, due to unforeseen events, my writing has taken a backspace but I hope to get back on track soon.

Isaac Kimaru
Isaac Kimaru

Writing full-time also started as a dream for me. Setbacks will be there, but please don’t quit. Learn and implement, and everything else will fall into place. Thanks, Mr. Mustafa!


“No matter how much you learn, and from who, if you don’t implement it, it’s useless.” The most important sentence. Very educative.

Isaac Kimaru
Isaac Kimaru
Reply to  Celestine

It hits differently when you have to experience it. By the time you realize it, you’ve wasted a lot of time. It shouldn’t be the same for everyone. Learn and take action, and I promise you’ll have zero regrets. Thanks for reading through, Celestine!

Reagan Oluoch
Reagan Oluoch

Very Inspiring Isaac

Isaac Kimaru
Isaac Kimaru
Reply to  Reagan Oluoch

Thanks for the kind words, Reagan!


Very inspiring. That’s the spirit.

Isaac Kimaru
Isaac Kimaru
Reply to  James

Sure, we must make it or make it. Thank you, James!

John Onyango
John Onyango

Thanks, Isaac, well, the same thing happened to me but I bounced back- keeping strong 4 years on. The secret? Unwavering determination!

Isaac Kimaru
Isaac Kimaru
Reply to  John Onyango

The newbies and aspiring writers should see this. Determination is the secret. Thanks, John!


Wow! Your story is such an inspiration to writers. If I may ask what’s your niche?

Isaac Kimaru
Isaac Kimaru
Reply to  Lucy

Thanks for the kind words, Lucy! My strength is in the digital marketing niche.

Ade Kiseu
Ade Kiseu

Isaac, you’re definitely an inspiration! On that learning and not implementing part, I’m a chronic culprit. But I’m improving straight to my writing goals. Thanks for the read! It’s worth bookmarking👍

Isaac Kimaru
Isaac Kimaru
Reply to  Ade Kiseu

I have also been a culprit for a long time, but everything changed for the better when I decided that enough was enough. Thanks, Ade!


A great plan plus determination is what drives one to success.
Very informative indeed. Thanks a lot.

Isaac Kimaru
Isaac Kimaru
Reply to  Irene

Wise words there, Irene. There’s no shortcut. Thank you!


Great article, I started the course beginning of this month, so far so good.

Isaac Kimaru
Isaac Kimaru
Reply to  Juliet

The course is detailed, and it’s tailored for beginners. You’ll get immense value. Welcome, Juliet!


I am so happy to learn I really love this information. what a Gold Mine!

Isaac Kimaru
Isaac Kimaru
Reply to  Diana

I’m also happy to see you happy, Diana☺. Great to hear that you learned a lot. Thank you!

Caroline Ayugi
Caroline Ayugi

The fear of failure most times holds me back from taking another step. But it is motivating to know that even successful writers failed more than once before reaching where they are. Thank you for the encouraging write-up.

Isaac Kimaru
Isaac Kimaru
Reply to  Caroline Ayugi

You are not alone, Caroline. We’ve all been there. But nothing can stop you once you put everything into place: the right skills and a budget to sustain you for a few months. Thanks for your comment, Caroline!


Wow! So inspiring! Thank you for keeping us we’ll informed about this industry and encouraging some of us who feel stuck in our demanding day jobs and wondering if it’s worth to leave it and pursue freelance writing full-time.

A good take-away from this post?

Always have an exit strategy, a solid plan if you truly want to pursue freelance writing full-time.

Have a why to keep you going when things are not working or when you’re feeling unmotivated

Thank you Isaac! 🙂

Isaac Kimaru
Isaac Kimaru
Reply to  Rita

Thanks for finding the article inspiring, Rita!

We all fear what is on the other side and tend to anticipate negative outcomes. That way, we still hold on to our day jobs even when we don’t really like them. Formulate an exit strategy and a solid plan, then take a leap of faith. We can’t win if we don’t play. Thanks again, Rita!

Judith Awino
Judith Awino

Honestly, LinkedIn is an absolute gold mine for any freelancer.

Isaac Kimaru
Isaac Kimaru
Reply to  Judith Awino

Sure. I think it’s the only platform where clients reach out to you. Writers should learn how to leverage it. Thanks, Judith!

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