The 3 Things I learnt From Freelance Writing Failure

Why you suck at freelance writing lesson 1 image

To have a facility for traditional writing — but not freelance writing— is a royal pain in the a***.

Our words are technically more proficient, technically more cohesive, technically ‘more right’, and yet they don’t delight audiences, drive sales, and build engaged tribes.

* What gives!*

At first, I thought, rather condescendingly, that this was because freelancing, (specifically for blog posts), is barely writing. I assumed it was a bottom feeder system that helped bad writers sell their services to even less able ones—robbing clients of 100 bucks for a blog post.


Then I thought, rather idiotically, all it would take was a semi-competent writer to enter the scene, and these chatty, paragraph murdering posts would be thrown out the window.

*Still wrong*

Finally, as my thousandth attempt to enter what I thought was a piss-easy industry failed….I questioned the quality of the audiences, their intelligence, their reason to be reading such drivel.

*Damn I’m an ass*

But then I stopped….


began to swallow my pride as a writer…..

*almost choked on it first*

……and finally decided to make a change.

It was time to turn that critical eye on myself

Questioning everything from the books I read to my definition of writing, I audited from the ground up my technical approach. I tore out the outdated flooring, I ventilated for the growing damp, and I redefined what I knew to be writing; so that slowly….. ever so slowly, I could discover what was holding me back.

There were tons of adjustments, improvements, and even necessary unlearning to be done, but before I could overcome this frustrating transition, I had to get past critically observing the successful, and start critically observing the 3 reasons that writers like myself, the failures, struggle to make the change

These were my findingsand the adjustments needed to succeed.

(For ya’ll skimmers)


Reason 1: Underestimating marketing……………………………………………………..

ii) Discovering my buyers process…………………………………………………………..

iii) Application of buyers process……………………………………………………………

Reason 2: Neglecting the numbers………………………………………………………….

ii) Access to explanations of 6 stress testing numbers…………………………………...

Reason 3: Thinking competence is the only authority…………………………………..

3 things I learnt from freelance writing failure

Reason 1#. Underestimating marketing

As I took stock of my mistakes, tallying the tendencies of failed freelance writers against my own, I started to identify two repeating themes that lead most beginners astray. I found that they (1) overestimated the importance of actual writing in our profession, and (2) massively underestimated the importance of perhaps the most critical part, business and marketing.

I saw signs of it everywhere, with people clamouring for posts like,

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and going crazy for articles like…

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but never for posts like this…

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There was a clear pattern.

Everyone was learning how to write for copywriting, blogs and eBooks, that information was everywhere and seen by everyone, they just didn’t know what to write and when — they lacked their marketing 101's.

Now, to rectify that, it doesn’t require you to get yourself a masters in marketing, far from it in fact.

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It simply means you need to focus on creating marketed copy (copy shaped to the consumer)—and to do that— gain an understanding of precisely what your consumers journey is from casual interest, to purchasing and reviewing your clients product.

That journey and that key marketing tool, is called your buyers process.

What Your Buyers Process Does

As a beginner and (most likely) someone with experience writing , you probably don’t have much trouble writing punchy intros, engaging transitions, and ribbon tied conclusions…..

But when it comes to executing for a client, most of us, regardless of our writing experience, have struggled with things like headline making, the voice you should use, and a host of other prewriting decisions.

As I said before, these prewriting decisions and difficulties can typically be grouped under one category—marketing—and if you’re struggling to make strategic and intentional prewriting decisions, this is usually a strong indication that you’ve not been utilising a consumer/buyers process.

What your buyers process does, is provide the data for those prewriting decisions by mapping the journey of the consumer from recognition to reaction—allowing you to map your work alongside that process—providing you with potentially viable paths forward.

For example…..

If you want to know if you should produce a top 10 post to inspire more leads, then you need to know precisely when the consumer will be encountering your post on their journey (and if they’ve reached stage 3 in their process—the comparison stage).


If you’re tasked to produce a blog post to inspire conversions, you want to pick a problem issue to agitate that comes early in their consumer journey, i.e at stage 1 or 2, which is the problem recognition and information search stage.

With your buyers process, what were once frustrating and freelance ruining questions before, are all questions you’ll be able to easily answer once you identify and familiarise yourself with your client’s consumer journey.

* But….What exactly is this hidden gem? *

In 1978, Engel Blackwell and Kollat designed a 5 stage buyers process model that made it pretty easy to understand:

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Buyers process Defined

  1. Problem recognition: This is where the consumer identifies a problem for themselves — or have been agitated to realise a problem by you — and are now aware of a product or service to remedy that want or need.

  2. Information search: Consumers will seek more information on the product they need, using search engines, social media and content creation platforms to explore the options before them.

  3. Evaluation of options: This is where they begin to balance the pros and cons. They’ve gathered information on the possibilities, now they decide which one is the best fit for them. Should they go with Apple for high quality and reliability, or is windows a better bet due to lower entry prices with equal specs — their wants and needs provide the criteria for them to evaluate against.

  4. Purchase: The consumer has chosen their number one choice and is almost ready to purchase the product. One of two things can happen at this stage: they can (1) proceed to purchase the product with no hiccups, or (2) back out of purchasing the product due to bad customer feedback, taxes, availability, or externalities such as delivery costs.

  5. Post-purchase decisions: Think Amazon reviews, Yelp, word of mouth, complaints, testimonials. It’s the actions your consumer takes post-purchase that impacts a business in a positive or negative light.

Ok Clarke, I’ve got it, so how do these stages help my Freelance writing?

At every stage of the ‘buyers process’, the unique steps of every customer present an opportunity to create specifically crafted content.

Insert your prospective reader into the process, whether there’s a product at the end of the stages or not, and you should gain a systematic incite into when and how you should be producing your content, driving most if not all of your prewriting decisions.

Lets examine a few ways it can influence your decisions:

If a customer — lets say Grace — is looking for the best web hosting provider for her site; then at stage 2 of the buyer’s process, she would be looking for a way to compare her options.

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For freelance writers, that ‘need’ screams opportunity for an abundance of content ideas. We could produce a top 5 post, a pros and cons post, or a why option C is the best post, and all of which would fit nicely into the funnel at that specific point, helping capture a high-quality lead.

Also, at stage one, is a further opportunity to agitate Grace into realising she has a need. She likely knows she wants a website beforehand, but has no idea what hosting is; that is an opportunity to create content that informs her on the process of creating a site, and how web hosting is integral to that process and a ‘need’ she knew nothing about.

Starting to see the aim?

At every part of the process, their specific needs at each stage of the model will cause them to pursue and desire information specific to your clients product or funnel. Grace wanted to make a website but didn’t know what her budget should be— that’s an opportunity to inform her of the variety of costs. Grace has gone through stage four and purchased your product, but she doesn’t know about website security software — that’s an opporunity to inform her on the details and then try to upsell her.

Specificity and knowledge of the micro details on their journey, helps you craft content that talks directly to your reader, precisely when your reader will want it.

We’ll go into detail on how to use this in later posts, but for now, insert your ideal client into this consumer model, and you’ll find a plethora of opportunities to create content your clients and consumers will love.

Reason 2# Neglecting the numbers

Within the financial banking system, there’s a term called ‘stress test’ that you might have heard of.

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No? Ok, ok….. well, it’s where the banks use hypothetical situations to identify whether the financial system would survive a series of unfavourable economic conditions.

Sounds pretty complicated…..

Sounds difficult…

It’s not.

If you cut the corporate jargon and stop trying to be a wise a** like me, it basically means this.

Does this mess of a system even work!?

In freelancing writing, high conversion writers test their work in much the same way as bankers, we use the abundance of metrics at our disposal to find out what consumers want, what the numbers are telling us, and whether the marketed copy we created in the last step is generating results for our clients.

Essentially, it’s a stress test on the efficacy of our writing.

  • Views tell you virality

  • Read percentages tell you engagement.

  • Sign-ups tell you successful leads.

Every stat has its story, and every number tell its truth

The mistake that beginner writers tend to make, and one I made myself, is undervaluing the importance of numbers in freelancing; people aren’t seeing the linkage between the data and it’s meaning, how every stat has it’s story, and how every number tell it’s truth.

Top converting writers, specifically copywriters like Neil Patel, never make this mistake. They understand their stats and their stories on an intimate level, frequently using them to evaluate the effectiveness of their decisions, and as tool to decide whether they should be sticking or pivoting at a juncture.

He’s one of the many successful copywriters who is constantly advocating for the increased use of metrical analysis— specifically A-b testing (which wouldn’t be available to us )— and through one of his posts, has brought to my attention a great example that shows it’s effectiveness.

A company called Crazy egg, a website optimisation site, wanted to increase their own conversion rates on their already successful site by hiring a conversion rate expert.

It seemed like a difficult task at best….

They had already ‘made it’ by most standards, had good numbers to parade and a high revenue stream to treasure.

If it was even possible to increase their conversion, I sceptically expected a slight increase that was a negligible 2–3 percent increase at best.

Boy was I wrong.

It turns out, the conversion rate experts managed to increase Crazy egg’s conversion rate by a whopping 363 percent in total, 30 percent of which directly came from increasing, not decreasing, the quantity of the copy on a previous page 20 times smaller— something completely counter intuitive to the popular short and sweet copy narrative.

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*mind blown*

That 30 percent chunk alone was discovered through one form of testing, (a-b split testing), and goes to show you the importance of unearthing common misconceptions with the analysis of the cold hard data, as what is true for Tom, Dick and Harry, may not be true for your client.

NOTE: A-b testing and many other forms aren’t available to freelancers to assist in improving their copy. However, many other surface level data sources are. Not to mention, if you own your own site, it also provides an excellent opporunity to do more complex forms of testing on your own blog, allowing you to self evaluate what types of copy work for when you undertake a client.

Every time you release a piece of copy, your clients readers are constantly conversing back their opinion in the form of numbers. But just because it’s in number form, it doesn’t mean you shouldn’t be reading into it the same way you would a review.

Freelance writing isn’t a hit and miss process, there’s a science behind the strategy, complexity to its simplistic facade. It’s a methodical process that constantly has you adjusting and calibrating your work to meet your clients and readers ever-changing needs.

Your stress test is your main re-calibration tool to adjust to those needs, so whatever numbers you can get your hands on, views, heat maps, google analytics, a-b testing — whatever useful data you can find, you should be adding into your freelancing stress test kit.

Don’t have the data? Request it from your client.

Don’t know what the numbers mean, learn the relevant marketing terms.

Yes, words and words alone are your tools.

But numbers are your friend too.

Use them.

Did you know: Speaking of stress test kits, this week, the mailing list got access to 6 of the metrics I personally use, the latest lessons straight to their email, and a weekly update on all things freelance writing. But you didn’t miss out ofc….. because you’re already signed up…. right? (download is located in the ‘p.s’ in the welcome email).

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Reason 3# Thinking competence is Authority

As a freelance writer, conversion can’t be achieved without a level of actual or perceived authority. Do you have the credentials and portfolio to support your claims, or does your work speak for itself, the proof being overwhelmingly in the pudding?

Either way, you’re constantly on a pursuit to substantiate your writing, to have a reputation that encourages conversion, and an authority that builds an inspired tribe.

To achieve that, us beginner freelancers tend to come from one angle.

From a place of knowing.

We understand that trust can be built by knowing our craft and by highlighting our expertise; so we teach, speak and preach about all the things we do know and seldom acknowledge the things we don’t.

We write from a place of being above.

That has its benefits of course, instructional’s, guides, tutorials, webinars, all need to be delivered with a level of assurance.

But the mistake we make as we just start out, is that writing from below in other instances, can be, (and usually is), just as effective.

People who write from below understand that:

  • Humility connects

  • Cock-ups and failures are all stories of relatability

  • and the small act of humbling yourself, endears you to readers in a way preaching can never do.

A smart man makes a mistake, learns from it, and never makes that mistake again. But a wise man finds a smart man and learns from him how to avoid the mistake altogether.
— Roy H. Williams

No fluff lessons are great, they’re time savers, lifesavers, and efficient at doing what they aim to do.


But lessons without contextualisation, are only doing half of the job that a freelance writer should be doing.


Let’s give you a little example of what I mean by ‘contextualisation’.

Out of these two premises for a post, which do you think is likely to convert more, have a higher engagement rate, and increase relatability with its readers?

  1. An expository narration of the processes involved in A-b testing, no example used, written only for those with industry knowledge, no questions, no misconceptions, no personal mistakes, pure numbered factual steps.

  2. A story based article that recounts how they discovered a-b testing through 6 months of zero growth, and how its implementation had them on their way to a monthly 20–30% increase in subscribers. Plenty of questions to gauge reader opinions, mistakes they made along the way, simple easy to follow explanations of otherwise complex terms, concluding with the things that are lacking in that type of analysis, and how it’s caused them a few misreads in their understanding of their consumer.

Pretty easy to tell right?

Context matters, but put more specifically, context stemming from your truth. I’m not the best freelance writer on the internet, but I angle my posts as a process, coming from a place of learning and constant and honest progression. You can feel my authenticity because I’m not afraid to admit my fudge-ups. I embrace them, and let you use them as a pedestal to avoid those same mistakes.

Remember this….

Authenticity doesn’t necessarily mean writing about how you love knitting. And it doesn’t mean your selling out to the man if you write about topics you don’t love. Authenticity is about finding the angle that resonates with your core, and enveloping the copy, (no matter the topic or your passion for it), with a wrapping of raw, real and relatable storytelling.

Mistakes matter to people just as much as your success.

Never forget that

Be truthful to you.

The Takeaway

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Before you go.

There it is folks, the 3 biggest mistakes that were holding me back as a beginner freelance writer. See any that you’re encountering too? Better yet, are there any that I left out? Let me know in the comments below what the biggest challenges you are/were facing as you start on your own freelance writing journey.

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