The Art of Non-Obvious Content Creation (And Creating Authentic Work That Lasts)
Box Cutter Co. Free Issue No. 74
Does your work spark curiosity—or satisfy expectations?
Which would you prefer?
The Problem of The “Obvious” Trap
Our brains crave the obvious. It’s efficient. Comfortable. Predictable.
When things aren’t obvious, we must think, ponder, reflect, and sometimes wonder. (In a society of convenience, this is often not a preferred approach to things).
“Obvious” content pulls us in, asking nothing new, requiring nothing extra. It’s familiar, easy to consume, and generally quickly forgotten. Most ‘leadership’ content on social media falls into this category.
“Non-obvious” content doesn’t simply inform—it encourages deeper thinking and reflection. (But not everyone likes that or is looking for it)
Obvious vs. Non-Obvious Content
Obvious content is easy to consume and requires little mental effort. It confirms what readers already believe or want to hear.
If you spend any time on social media and think about content creation and digital writing, you’ll see the usual obvious commentary everywhere:
“Success is a mindset.”
“Consistency is key to growth.”
“Engage more to grow your audience.”
“Follow your passion, and success will follow.”
Any monkey or AI tool can churn these out until the end of time… Yet there they are, plastered all over social media daily.
They are familiar, comfortable, and formulaic. Obvious content is made to be liked, shared, and quickly forgotten. And for many, the search is to become like the flu and “go viral”…
Non-obvious content, on the other hand, is more challenging to digest. It requires reader—and creator—to pause, question, and think.
In patent law, “non-obviousness” means an invention no one else could easily think up and post.
In content, non-obviousness separates original insight from recycled ideas, echo chambers, and bullshit-on-repeat.
Non-obvious work doesn’t generally confirm or conform — it often disrupts, instigates, provokes, or simply ignites some thinking and reflection.
It requires more of its readers/audience. It can offer a deeper experience. It doesn’t aim for quick applause but for lasting impact.
The Appeal and Pitfalls of Obvious Content
Obvious content creators have mastered the art of quick resonance. They produce work that’s relatable, immediate, and ready-made for sharing. They often succeed by meeting readers’ expectations rather than challenging them.
This by no means Obvious content is ‘bad’ or not valuable.
Some Obvious content creators have done very well with their work. For example:
Mark Manson is a prime example. His The Subtle Art of Not Giving a Fck* repackages familiar self-help concepts with blunt, engaging language. The approach resonates because it feels fresh, but the core ideas echo popular advice on acceptance, resilience, and letting go.
James Clear with Atomic Habits focuses on small, actionable improvements. His work appeals to readers who want simple strategies to improve their lives, framed in straightforward terms. Clear’s content is popular because it’s accessible and actionable—obvious solutions presented in a new way.
Marie Kondo offers a philosophy of decluttering both practical and emotionally satisfying. The Life-Changing Magic of Tidying Up repackages familiar ideas about organization with an emphasis on “sparking joy.” Her method resonates by giving a clear, almost ritualistic framework for letting go of shit.
Each of these creators has built a massive following by giving people what they want: clear, digestible advice.
There’s value in this, but it often fades once the book is read or the next Obvious book or Creator comes along.
Why Create “Non-Obvious” Work?
Creating non-obvious work means choosing a more challenging path. Similar to patent law, non-obvious means original, more thinking, and more reflection.
It won’t attract instant likes or shares, and it doesn’t follow predictable formulas.
Non-obvious work challenges assumptions and asks readers to think differently, to move beyond what they already know. This kind of work can last because it resonates deeper.
But to create non-obvious work, a shift in mindset is essential.
Obvious content is fast and efficient, built for quick consumption. This makes it easy for people to press the ‘like’ button, the ‘re-post’, and so on. Because it “makes sense” to them.
Non-obvious content, however, takes time, depth, and a willingness to move against the current. Maybe even swim upstream.
Learning from Non-Obvious Creators & Thinkers
Some creators don’t just add to a conversation —they redefine it. They challenge what we believe and push beyond the obvious. Here are some of my favourites, and we have their books on our shelves.
Edward de Bono
Dr. de Bono wrote over 85 books on topics related to creativity, lateral thinking, and problem-solving. His work has been translated into multiple languages and is widely regarded for its insights into innovative and non-linear approaches to thinking.
de Bono sent newsletters (e.g. letters) to subscribers in the 1970s and 80s, long before email lists. Some of his best-known books include Lateral Thinking, Six Thinking Hats, and The Mechanism of Mind. (I have many of his books on our shelves).
His work demonstrates non-obvious creation isn’t new—it’s a honed and practiced mindset valuing exploration over the tried and true.
Barbara Ehrenreich
…looked at minimum-wage work and “positive thinking” culture and turned them inside out. Nickel and Dimed and Bright-Sided aren’t just books — they’re social critiques and mirrors held up to social myths.
Ehrenreich challenged readers to see things as they are—not as we wish they were.
Esther Perel
…has taken a well-worn topic—relationships—and redefined it.
Her work in Mating in Captivity and The State of Affairs isn’t about judgment —it’s about understanding and empathy. She asks readers to view relationships as complex and evolving, to hold space for contradiction and tension.
Daniel Kahneman
… a Nobel Laureate, revealed how flawed our thinking can be. Thinking, Fast and Slow (written with Amos Tversky) unmasks many biases that shape us, challenging the myth of rationality.
Kahneman’s work reframes how we see ourselves, exposing blind spots that were always there. The metaphor of System 1 and System 2 in our brains is powerful (see image above).
One is fast and reactionary, the other is slow and methodical. Both are valuable and needed.
Nassim Nicholas Taleb
…reframes risk and uncertainty. In The Black Swan and Antifragile, he dives into the unpredictable and demonstrates how should see it as necessary rather than as a threat.
Taleb’s work and thinking remind us that the non-obvious often lies where we least expect it—in chaos, in resilience.
Each of these thinkers embodies non-obvious creation. They didn’t satisfy expectations; they disrupted them. They created work with a slow-burn effect, work that demanded thought, and work that lasts. Many of de Bono’s books were written in the 1970s and 80s.
Strategies for Creating Non-Obvious Work
One of the top (and obvious) strategies for creating Non-obvious work is… read Non-obvious work… (yea, duh).
One digital creator and book author I’ve followed for close to two decades is Seth Godin. He’s published a daily post on his blog for two decades. He then takes the more popular posts and publishes them as books. (He’s published about 20)
Another creator and book author I’m a big fan of is Austin Kleon (also here on Substack).
And the only Substack I am currently a paying subscriber to is Category Pirates 🏴☠️. Much of my thinking on Obvious and Non-obvious content is inspired by their brilliant work.
(If you’re a writer and want to dive deeper, buy and read their ebook Snow Leopard: How Legendary Writers Create A Category Of One)
In addition to reading Non-obvious creators, writers, and thinkers — If Non-obvious creation and content is your goal, a certain mindset is essential.
Here’s ways to develop and support that:
1. Demand Originality
Treat each piece as if it’s the last word on the subject. If it doesn’t make you pause, it won’t make readers pause.
2. Connect What Others Won’t
Find unexpected links. For example, relationships and resilience. Risk and freedom. The new emerges from unlikely intersections.
3. Work Slowly
Don’t rush ideas. Let them mature — resist posting just to post (e.g. “be consistent”). Depth often grows in the quiet (and unexpected).
4. Challenge Every Assumption possible
Especially your own. If it feels too easy, look closer. Truth often lies in discomfort. Different lives in discomfort. It pushes against our brain’s hardwiring to stand out, speak up, and not conform.
In bygone days, this meant ostracism and social isolation — sure death.
5. Value Impact Over Attention
Don’t aim for views, likes, follows, or reposts. Aim to be remembered, original and thought-full. Write for readers who value substance over distraction and echoing all the other obvious shite.
Why Non-Obvious Matters
Non-obvious work doesn’t seek to fill space. It aims to leave an impression. It’s work that lingers, questions, and maybe, just maybe, transforms.
The path to creating Non-obvious is slower and requires a disciplined mind, one that sees the value of moving against the current.
I luv the idea of the column. I agree with it in principle. I utilize those principles. Well done.
obvious" vs "non-obvious” both are useful ways to view opinions and information but the non people are more fun