This post is part one of a two-part series. In part one, I share 4 of the most important lessons I learned in my first year writing for a living.

In part two Richard shares his. You can apply these lessons to your writing career – whether you’re an aspiring, new, or seasoned writer.

Many of you already know my freelance writing journey. But for those who don’t, I’m going to share it, once again. Why?

Because my story provides context to lessons I learned in my writing career. It is these lessons that have moulded and helped me build a thriving writing business that earned $3600 last month.

And, I hope these lessons help you build your own writing business, realise your worth as a writer and help you earn more.

My Story

I started dabbling in freelance writing in June 2016 after I landed a job writing for Lifehack. 35 posts later and I ended that relationship.

Why? Pay was low. In fact, it was a mediocre $15 an article. But, it was a solid starting point. Besides, we all have to start somewhere right?

During that time I did consider writing as a career. But I wasn’t sure about how to get going and move beyond the low rate. All the information online compounded that problem.

Where would I start? What resources would I use? Who would I follow? How would I make money writing for a living?

My fortunes changed when a timely email arrived in my inbox. Bamidele Onibalusi announced the Earn Your First $1000 as a Freelance Writer Challenge. He provided a roadmap for building a writing career from scratch, and I latched onto it.

I followed his strategy, and within a month I had my first few clients. With that as the foundation, I built a profitable writing business in 12 months that comfortably makes $2500/month. In fact, only last month I made $3600.

Were there challenges? Yes! I remember writing for an overly demanding agency. I remember one client criticising my work. I even remember chasing down payment with that agency.

It was tough, but I overcame these challenges and learned a lot in the process. It is these learnings I want to share with you so you can achieve your own success. Here are 4 of the most valuable lessons I learned.

1. You Need a Strategy If You Want to Make a Living Writing

Let me share a secret with you. Even before I started writing for Lifehack, I had considered freelance writing. I even launched a challenge for myself to become a freelance writer. What happened? Nothing. Absolutely, nothing.

And while writing for Lifehack was a step up from “nothing”, I still wasn’t earning very much. The real problem here was that I had no direction, no roadmap, and no clear path towards success.

But that changed thanks to Bamidele’s strategy. I created a website, positioned myself, obtained social proof, and used cold pitching to find clients.

With the strategy, I was able to land two clients, both of whom are still clients today. In fact, one client remains one of my most lucrative clients, ever. If you want to see how I landed that client read How I Landed a $6250 Freelance Writing Gig (As a Beginner).

My point is that my initial success wouldn’t have been possible without a strategy. And so, for anyone who wants to launch their writing career, create your roadmap.

You don’t have to use Bamidele’s strategy. But the many people who’ve achieved success using it are proof that it works. So, it’s a good starting point.

2. Outsourcing Will Free up Time and Help You Scale Your Business

Shortly after launching my writing business, I realised that I would have to do more than writing. I would have to track expenses, send invoices, do tax returns, and market myself, all while putting pen to paper.

I was a business owner, and there was a lot manage. I couldn’t do it all myself unless I wanted to work ridiculous hours and feel drained each day.

What did I do?

I harnessed the power of outsourcing.

I found someone to do my tax. And, I even outsourced some of the work I did for clients. The outsourcing, in this case, was transcribing. If you’ve transcribed before you know how time-consuming it can be.

Outsourcing saved from the mundane tasks. It gave me time to focus on tasks I enjoy: writing and marketing. And, it also helped me scale my business.

In the future, I plan on using ghost drafters so that I can produce quality content faster. A ghost drafter is someone who does the legwork for you. They compile the article from your outline and find the case studies. You just add your personality and final touch-ups.

I came across the technique after listening to Jacob Mcmillen interview Aaron Orendorff. Aaron earned $19,000 in a single month as a freelance writer, so his advice is worth listening to.

Pro Tip: Get an editor. Every writer should have an editor. Beyond time savings a good editor will take an average article and make it great. If you’re struggling to find one, I strongly recommend Spike Wyatt.

3. Your Clients Will Manage You If You Don’t Manage Them

Remember that gig writing for an agency? Well, pay wasn’t great, but there was an upside: a constant stream of work.

Things started off well. For my first gig, I wrote an eBook for R3500 That’s $260 at the current exchange rate.

They paid me within a week, and I was happy.

But, over time, pay was less frequent. In fact, I spent a lot of time chasing payment.

Not only that, but they were demanding. Deadlines were always tight; they wanted the articles yesterday. In one instance they sent me a brief on a Friday and expected me to have it ready by Monday. No regard for my weekend whatsoever.

But the fact was I was to blame because I wasn’t taking charge of the situation. But things soon changed.

I realised that for the sake of my own happiness I would need to manage them. Otherwise, this would repeat itself, over, and over, and over, again.

To address the issue of constant tight deadlines and running on urgency I sent them an email. I titled it “Improving workflow”. Here’s that email:

Hi [insert email],

A few months ago I filled out one of your contract surveys about what you could improve. 

There are a few additional things I would like to add to what I said to ensure that I provide the best possible service and timely delivery of articles for you at [company name].

Would it be possible to brief me on all articles one month, or at least a couple of weeks in advance, to plan the work as set out?

Generally speaking, running on constant urgency is unnecessary and bad for overall standards. Failing to plan is planning to fail. 

Case in point is the [company name] blog brief you sent me on Friday afternoon that was due on Monday. It would be great to fine tune our system to a point where it runs smoothly and efficiently.

As it stands, for next week I’m writing four articles for [company name] and two for [company name], of which I’ve yet to receive the briefs. [name] also made mention of [company name] blogs, but not sure when those will be coming in? 

With the healthy volume of work coming in at a good pace, I must ensure that I maintain the highest quality for you guys, and being able to plan better is the key to being able to do this.

I seriously enjoy working with your company and look forward to meeting you all soon.

Warm Regards

Nick Darlington

The trick with this email was that I made it about them, despite it actually being about me – and making my life easier. I wrote it in a way that showed that implementing those changes would benefit them.

In constructing this email, I consulted a friend. It took a lot of time. But it was the starting point for developing a hard skin and not taking any shit from clients.

Because if you continue to give in to client demands that don’t respect you and your time, only you are to blame. No one else!

And the client’s response to this? It was positive. He thanked me for it and said that they were, in fact, implementing a new workflow soon.

Now, as for the late payment story. Well, I cannot find the exact email I sent. But again, it boiled down to me taking charge of the situation. I politely said that I wouldn’t be writing any further articles until they paid me.

And just like that, I stopped writing for them. Was I better off for it? Definitely. Admittedly, It was hard to let go of that job. It’s funny how you develop an attachment to something. How you depend on it. How you don’t want to lose it. Despite it being bad for you

But, you know what? It was the best decision I ever made. And, as I’ll show you in the final section, I have since landed my highest paying blog gig yet -$250 for a blog post.

It was all due to a simple action I took. Indeed it was one of the biggest lessons I learned in my first year, and it’s a lesson I hope you learn from and carry with you on yours.

4. What You Charge (And Earn) is Up To You

After I quit writing for Lifehack, I started increasing my rates.

I increased my rates to $100 for a blog post but did accept gigs that paid me $50, as long as the frequency of work was good.

As I wrote more and clients were happy, I grew in confidence. And so, I started charging, even more, to the point where I landed that $250 blogging gig

It wasn’t magic. It wasn’t anything out of the ordinary.

I just decided I was worth more, upped my rates, and found a client that was willing to pay those rates

The above chain of events is the perfect example that what you earn is your choice.

It’s your choice to earn $3/article

It’s your choice to earn $50/article.

It’s your choice to earn $200/article

And so it goes.

But how do you know when to increase your rates? How do you know how much to increase them by? What is acceptable and what isn’t?

There’s no golden rule, and I would say that if you want to increase them, do it. No one is stopping you.

Also, as you build your writing career, don’t stop pitching and increasing rates with new prospects. By doing this, you’ll be able to get rid of those low paying gigs.

Hell, even consider increasing your rates with existing clients (it’s not as hard or as daunting as you think). If you want to see how I did it, read my article How to Easily Increase Rates with Existing Freelance Writing Clients.

And if you’re scared of upping your rates out of fear that potential clients will run, don’t be. Sure, some clients won’t accept your higher rates, but I guarantee you that there are clients that will.

And those are the clients you want to be working with anyway. They’re the ones that value you. And when you feel appreciated the quality of work will improve.

You’ll want to write for them. You’ll want to deliver. You’ll go the extra mile, and they’ll love you. And before you know it, you’ll be making a healthy living writing.


A lot has happened in the 12 months that I’ve been writing for a living. I started my writing journey when I landed a gig writing $15 articles for Lifehack.

I stumbled across a strategy that helped kickstart my writing career. From that point, I never looked back, and I’ve managed to increase my income month on month.

There were many challenges, but those challenges made me stronger. I learned from them and used them to supercharge my writing career.

I’ve realised the power of a strategy toward building success. I’ve learned that to remain sane and scale my business; I must harness the power of outsourcing. I’ve learned that if you don’t manage your clients, they will manage you.

Perhaps, more importantly, I’ve learned that what I charge is my choice, and mine alone. If I’m not happy with my earnings, I can change that.

I hope these lessons will help you in your writing career – whether you’re an established or aspiring writer.

If you’re an established writer, please join the conversation below. Share some of the lessons from your career and, together, let’s helps other writers.

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