Writing Challenge 2024
300-word essays about interesting ideas
1. When I first started writing content in October 2013, for $5 a piece, I placed a 300-word limit on myself for any (and every) piece of work I wrote. My thought process was that 300 words were plenty to get a key point across while also forcing me to understand the topic well enough to stay concise; 300 words leave little room for bullshit and, more importantly, pointless tangents (a bad habit of mine).
My goal for 2024 is simple: write a set of 300-word essays based on my experiences as a professional writer and amateur human. Whenever a topic gets me thinking for more than sixty seconds at a time, my job will be to turn it into a 300-word essay. The hope is that by the end of the year, I will have a collection of writings to call my own.
I’m doing this for two reasons: one, to focus myself on an achievable goal. Two, my ego is screaming out to me for me to spend more time thinking and writing for myself.
Meanwhile, my brand as a freelancer continues to lack focus. My hypothesis is that writing and publishing these short articles on a personal website (or something similar) will add a bit of sparkle, credibility, or whatever you want to call it, to my one-man show.
This is a challenge not taken lightly. As of today, I have exactly six topics to write about. Given I’d like to write two of these a month for the next 12 months, I’m still 18 short of a complete set.
The reality is that I probably won’t hit 24 by the end of the year. But in my defense, that’s not the point of this exercise.
And if you’re wondering, this essay is exactly 300 words long… now.
How to Not Die as a Freelancer
2. In August 2021, I officially went freelance with zero clients, zero income, and zero ideas.
By admitting that I had deliberately thrown myself in at the deep end, a swimming analogy helped massively in assessing my position. Here are my tips for not dying as a freelancer.
Step 1. Don’t drown.
When I hit the water as a rookie freelancer who barely knew how to swim, my priority wasn’t to thrive as a professional—it was to survive the shock. I breathed whenever I could, and only ever focused on the next breath.
Step 2. Tread Water.
Once the shock wore off, treading water allowed me to take stock of my situation. Am I safe yet? Do I have support mechanisms in place? Am I insane? Looking back on it, I perceived this stage as being shorter than it was. In reality, I spent a year doing this.
Step 3. Start Swimming.
The first time I consciously realized I was doing something right. After a handful of consecutive months of being able to pay my bills without sweating, I started swimming roughly 18 months after going solo. Note that this doesn’t mean I was (or am) a strong swimmer.
Step 4. Pick a direction.
Swimming without direction isn’t productive. By spring 2023, I finally understood that I’d go nowhere if I expended all my energy on swimming in circles. After a couple of small projects fell into place, I took a punt on sticking to the same kind of work for the time being, even if it meant slower progress.
Step 5. Improve your technique.
As I enter 2024, I have been incredibly lucky to have increased my revenue in each of the past three years. Finally, I can start working on my technique. But there’s no land in sight yet…
Some chaoses are bigger than others
3. I worked with two teams of freelancers in 2023—one group got laid off. Here's how the story goes.
They were unpredictable to the point of incredulity:
1) We didn't know when the work would come in;
2) Whether it would be a 10/10, or a 2/10;
3) We couldn't even predict the mistakes they were going to make.
Our hand was forced.
But the interesting part is how we compared the two teams’ output—because the team we retained was making similar mistakes, just on a more predictable level.
After some reflection, we realized that their problematic behaviors were less problematic than the other teams’ problematic behaviors—furthermore, they had a much grander scope for trainability and improvement if we were willing to put in some hard work and instigate a better quality control process.
We concluded that while predictability is trainable, unpredictability is not.
In other words—and to crudely rework an analogy from the author John Green—some chaoses are bigger than others.
My job was to instigate a quality control process for a content mill that had ignored the quality of its output for more than two years.
The new editor-in-chief realized how laissez-faire the operation had become, and the vast majority of the content fell way below the required standards. By not measuring the work being produced on an ongoing basis, a dam had burst and let all sorts of content through onto the web. This was unacceptable, and I was brought in to steady the ship as best I could.
After letting Team A go, we got to work on creating a training guide and template system for Team B. It was a much better use of our time and we saw immediate results. More results coming soon!
The point is, even problematic behaviors can be advantageous.
"He talks too much, daddy"
-- A very rude child I met once
Change one word. It makes a difference.
4. One of my gigs sees me editing other writers’ content before it goes out for publication. As much as my job is to focus on the body copy, I can’t help but indulge in tweaking their headlines whenever I spot an opportunity.
The following example shows how a writer used the word 'but' in their headline when an 'and' would have transformed a dull story into a refreshing one.
I’ve reworked the original to spare any blushes:
"This Company Broke The Cardinal Rule—But Pulled It Off"
"This Company Broke The Cardinal Rule—And Pulled It Off"
I hypothesized that these headlines painted two different stories about both The Cardinal Rule and The Company Who Pulled It Off.
1) "But" = negative connotations (against the odds, a risky maneuver)
2) "And" = positive connotations (innovative creators, questions the Rule)
I put the question to my (disappointingly small) LinkedIn following and asked whether my hypothesis held water.
All (five) respondents agreed that I was onto something.
Here’s my point: one word can make a massive difference in how your messaging is received...
...yet so few businesses seem to take this axiom seriously.
The loss of credibility, trustability, comprehension, and even conversion that most site owners aren’t aware of continues to baffle me.
Meanwhile, I can identify the businesses that take their copy seriously within a few seconds of landing on their homepage.
The question is: if I landed on your homepage today, what would I spot?
I spend the vast majority of my day reading news stories, press releases, home pages, and social media posts, and so many could be improved with a 15-minute copy review by your Average Joe wordsmith.
By chance, I happen to offer that as a packaged service. Funny, that.
One word makes a difference. So make it.
300 words….now.
Writing minus Editing equals Nothing
5. "I apologize for such a long letter - I didn't have time to write a short one."
Since the birth of ChatGPT, Mark Twain's corpse has begun to spin steadily in its grave, and its revolutions are accelerating exponentially. Here's why:
I've noticed an ugly pattern of (very clearly) AI-generated blog content that undermines the things that made blogs so great in the first place.
It appears to me that companies (and publications) are leaning into half-baked TOV and lazy subediting processes.
These repeat offenders are confusing casual conversation with accessibility.
Their word soup damages credibility, reduces readability, and wastes everyone's time.
In reality, the deletion of this kind of language is what makes their content more digestible.
In other words, less fat, more meat.
I recently read a 1450-word blog post that could have easily been 600 words of industry-leading gold if someone (anyone) had just edited the thing.
Check this out:
"Tired of the moving process that's about as fun as assembling a complex piece of IKEA furniture? Product X swoops in with professional move-in and move-out services managing and verifying the property's inventory list. It's like having a team of pit crew racing against the clock, ensuring your move is as smooth as a hot knife through butter."
58 words. Three metaphors. Fatty meat.
Why not say:
"Moving homes is a complex, time-consuming process that should be much easier. Product X does this by offering end-to-end professional move-in and move-out services (including inventories) that reduce stress, boost efficiency, and accelerate the move for everyone."
Shorter, clearer. Leaner meat, fat for flavor.
Use ChatGPT to build your content—I encourage it. But your editorial process supersedes the AI.
If you can't have both, do neither.
The good news: I know what good editing looks like. Ask to find out more.
Why aren't we talking about mental health and the workplace?
6. In 2009, a harassed France Telecom employee took his life. His suicide note said, “I am committing suicide because of my work. That is the only reason.”
The Orange S.A. suicides teach a harsh lesson about how workplace experiences and mental well-being are intrinsically connected.
The workplace is becoming an increasingly existential threat. There is a generation of workers traumatized by the workplace—whose entire identities have been eroded by the workplace.
This is no glib statement. The CDC (Centers for Disease Control and Prevention) has a guide about how to spot signs of suicidal depression in the workplace.
It got me thinking, how did the workplace fuck me up?
I’ll have a stab at it now.
Some context: a history of chronic health conditions has seriously affected my relationship with the workplace, one that became increasingly strained due to prolonged absences and my continued inability to maintain a 40-hour work week.
Work is how I spend the majority of my waking hours. The workplace saps the largest proportion of my energy. The workplace inevitably occupies my thoughts during downtime.
Yet during these bouts of ill health, the workplace repeatedly reminded me how I should prioritize its survival over my own.
In analogy: I increasingly believed I was the runt of the litter and ran the risk of the pack (the company) dying for my weakness.
This eventually infiltrated my wider experience until, one day I stopped prioritizing myself completely—in no small part due to workplace conditioning.
Side note: I have experienced two major global financial meltdowns and a global pandemic. Existential threat? You bet.
In a statement made after Tim Bergling’s (Avicii’s) death by suicide in 2018, his family said, “Tim was not made for the machinery he ended up in.”
I sometimes wonder whether any of us are.
Hit rock bottom? Grab the pickaxe!
7. The story goes that a sharp-witted but disappointed teacher, in writing his end-of-year comments about a promising student, claimed the boy had hit rock bottom and somehow contrived to grab a pickaxe.
The professor grudgingly admitted to admiring the young boy’s audacity to tackle his abject failure by stooping to new depths.
With a healthy dose of humour and admonishment, the teacher coined a metaphor I have always found fascinating: no matter how low you go, there are always new depths to be explored.
When you hit rock bottom, why rush to leave? There may be value in digging a few inches deeper.
Who knows what value hides beneath the surface, even if it’s just the pleasure of knowing how you hadn't hit rock bottom after all!
The archaeologists will say the best fossils lay deep in the dirt. The psychologists will tell you that self-reflection on a deeper level is the key to enlightenment. You get the picture.
There are different types of rock bottom. Some are exploratory, digging deep for the fun of it. Others are thrust upon us, sending us so deep that the sun is blotted out by walls. Others are gradual slides, invisible to the naked eye.
And while some may have the privilege of having their escape ladder ready to hand, the accepted reality is that most people who find themselves rock bottom will likely have to climb jagged walls by their fingernails to escape.
Perhaps the ladder of liberation is buried beneath rock bottom, only accessible with a conscious effort to plunge yourself even deeper into the mire. Wouldn’t that be ironic?
It’s no fun, it’s dirty, sweaty work, and it wrecks your clothes.
But next time you’re sitting in a hole, rock bottom, ask yourself if down is the new up.
300!
"Who is this guy?"
-- A very rude girl I met once
Moon/Paint. Sun/Canvas.
8. First, the context.
My first major copywriting project as a freelancer came in the form of a rebranding and rewriting exercise with the wonderful Viola Eva at her agency, Flow SEO (testimonial on my homepage).
Viola’s testimonial is spot on: I really did make her work hard for the copy (the project took close to four months to complete) but by the time we finalized the project we were both happy with the new positioning for her agency.
But first, the website had to go through a significant redesign to make the copy ‘pop’, and this took the best part of a year.
Then, ChatGPT came out and changed our lives.
And now, the story.
About six months after the redesign went live, Viola started to make changes to the copy. At first, I was sad to see our hard work disappear.
But a few moments of reflection proved priceless to me moving forward.
One, Viola had to quickly adjust her positioning to take into account the launch of Open AI’s game-changing technology. I couldn’t argue with that.
Two, the more I read on the (now) updated website, the more I realized that I was operating under the false impression that my copy was the star when in reality it was the moon, in orbit but not the headline act.
Or, to try a more visual analogy, copy is the paint, not the canvas.
My copy was never meant to be forever—words fade over time. The real win was that we chose the correct canvas to paint on!
At the time of writing, Viola’s website still has a strong scent of MrHarveyHancock, and I am delighted to see so much of our content remain three years later.
A deep-dive case study is on the way. Watch this space.
300, now.
A 300-Word Overview of Quality Control for Content
9. I was tasked with creating and overseeing the execution of a quality control system for real estate listings being uploaded onto Spotahome’s website.
The good news: we nailed it.
Here’s how.
First, we split the content creation process into every step a copywriter took before hitting ‘Publish’ on a listing, assigning a score to each step.
For example, typos were forgiven as minor setbacks (1pt); a listing with a badly labeled image (‘bathroom’ instead of ‘kitchen’) would score lower on Quality but still be publishable (5pts); while a listing without any text or images would fail the quality control test altogether (25pts).
In total, we found 135 points’ worth of quality control per listing.
Our (surprisingly pretty) Quality Control Spreadsheet used a series of Yes/No checkboxes that added or removed points as we progressed through Quality Control Checks, with a percentage score assigned at the end of the check. It was consistent, repeatable, and highly accurate.
We tested a set sample size for each of our (20+) writers. Writers with lower average scores needed their listings checked more often, while high-flyers required less observation.
Two listings per writer, per day was enough of a starting point to get an average score for each writer without saddling ourselves with the need to check every new listing.
We then collated total scores by writer against their previous month’s performance to measure improvement over time.
At the end of the month, we shared these figures with all writers, highlighting the most common issues on a team and individual basis as a benchmark for what needed to be improved by next month’s reporting.
Within 3 months we had eliminated 100% of listings below minimum publishing standards and raised the overall score of our listings to around 95% quality.
It was ridiculously successful. 300.
What might an AI Native Curriculum Look Like?
10. Not that anyone is talking about it, but the first generation of AI-Natives has already been born and, probably, is already in formal education.
How long until prompt engineering becomes an essential part of her education? And what could that curriculum look like?
Firstly, let's assume that AI technology is not limited to the working world and has infiltrated daily life as a search engine, a personal assistant, a creative assistant, and can effectively turn any thought or prompt into a reasonable response. Like Black Mirror, but slightly less bleak.
How does my AI-Native master prompt engineering and live harmoniously with her tech?
First up, communication skills. Extracting useful information requires useful questions. This isn't a naturally occurring skill (like speech) so I'd like English class to integrate classroom activities whereby students collaborate on building excellent questions for their AI assistant to fetch an answer to.
Second up, ethics and morality. There's not much to add here but to point out there are many things a person shouldn't ask their AI to do. This is an interesting combination of philosophy and IT class, and it would be a core subject like maths and basic sciences.
Thirdly, keep the core subjects, for goodness sake. I can't have my AI-Native student asking Siri what she gets when she adds 2+2. Maths stays. Same goes for core sciences and religious education.
Finally, data analysis and methodology. My perfect AI-Native never takes Alexa for her word. She needs to know how to take information, interrogate it (and other sources) and find an answer that makes sense to her.
With enough wits about her to not let ChatGPT fool her and—sometimes—ask it a question so perfect that even GPT applauds, perhaps my AI-Native can lead us, eventually, to the fabled Level 2.
300.
"I'm Not Miserable!" Yells Miserable Man
11. "So this is easier now/
I've found all the pieces that I lost in the flood/
And it wasn't that much..."
--
My advice?
Scream however you want.
Scream loud and proud.
But don't assume your scream is anything the crowd wants or needs to hear.
Don't even assume you're screaming the truth, the whole truth, and nothing but the truth.
When Frightened Rabbit frontman Scott Hutchison sang "I'm not miserable" as the rest of his bandmates chorused "I am, I am" in the background, it's hard to imagine the "I am" as being anything more than poor Scott's subconscious.
Poor Scott indeed. Eight years after I'm Not Miserable hit the shelves in record stores, the troubled singer-songwriter took his own life after a long history of depression. If that doesn't add a layer or two to his lyrics, what else could?
Listen.
You can't fear the strength of your own convictions.
What you say and what you need to say are two TOTALLY different things.
Scott felt he needed to say he wasn't miserable...but he knew he was (that's the point of the song).
I'll assume that most of your messaging comes from sit-down marketing meetings, not dam-bursting moments of divine clarity.
The thing is...
That's not what you want to say. Not really really.
Because we both know the real-hard-hitting message, that one that catches in your throat whenever the thought comes to you, is the one that needs to be put out there the most...
And therein lies the key to Absolute Truth.
For yourself. For your customer.
For your bandmates.
I submit that it is your responsibility to share your message.
Even if it scares you. ESPECIALLY when it scares you.
If you do not face this fear, you will never win hearts, minds, or wallets.
300.