Your Writing Fails if Readers Feel Dumb (#4)
On Joe Rogan Experience (#2285), comedian Andrew Schulz made an observation about politics:
"Alright, well, I'm stupid. I'm dumb. I'm dumb then. So why doesn't somebody meet me where I'm stupid and start at least making me feel like I’m not an asshole...?"
This part of his larger statement can easily apply to technical writing.
Bad writing alienates readers because the author incorrectly assumes the readers' level of knowledge. This leaves readers wondering if they missed a step. If the author assumes too much, people disengage, stop reading, and walk away from the text. I know. I have done this myself.
Good writing does the opposite. You can make people feel capable, knowledgeable, and included.
Scale Difficulty
In Orson Scott Card’s Ender’s Game, Ender Wiggin arrives at Battle School completely unaware that he’s being trained for war. He’s brilliant, but he’s also a kid thrown into a complex new environment where the rules aren’t clear yet.
Colonel Graff, the officer in charge of his training, doesn’t throw Ender into combat and expect him to figure it out. Instead, he scales the difficulty — pushing Ender just hard enough to stretch his abilities but not so much that he crashes. Every lesson builds on the last.
Good writing scales with difficulty. It builds on previous knowledge, introduces new ideas step by step, and never overloads the reader.
In Cognitive Load Theory (1988), John Sweller found that working memory — the part of your brain responsible for actively processing information — is extremely limited. Most people can only retain and manipulate three to five pieces of new information at a time before cognitive overload sets in.
If explanations introduce too much information too quickly, comprehension stalls. Readers stop absorbing new ideas and start feeling overwhelmed.
In his experiments, Sweller demonstrated the following:
Step-by-step guidance improves learning. Students who studied algebra problems with full solutions provided performed better than those who had to solve the problems from scratch.
Poor structure reduces retention. Learners remembered less when information was presented in dense, unorganized blocks instead of clear, structured steps.
Cognitive overload weakens problem-solving. When too much information was introduced at once, participants struggled to apply what they had learned.
The takeaway for us is to provide readers with just enough information at the right time.
But that’s easier said than done.
The more you know, the harder it is to remember what it was like not knowing. That’s where most writers go wrong: they’ve forgotten what it’s like to be in their ignorant readers’ shoes.
Curse of Knowledge
In 1990, Stanford researcher Elizabeth Newton conducted a simple experiment to measure the gap between what experts know and what they assume others know.
Participants were split into two groups: "tappers" and "listeners." The tappers were asked to tap out the rhythm of a well-known song (like "Happy Birthday") on a table, while the listeners had to guess the song.
Before starting, tappers were asked to predict how often the listeners would guess correctly. They estimated 50%.
The actual success rate?
2.5%
The tappers were stunned. To them, the song was obvious — they could hear the melody in their heads as they tapped. But the listeners? They heard a series of disconnected knocks.
This is the Curse of Knowledge in action. Once you understand something deeply, you forget how you felt when you were ignorant. In turn, this can have negative impacts on your writing:
Using terms and concepts without introduction
Eliminating intuitive steps
Confusing readers who need your guidance
You have to mindfully bring your readers from ignorance to understanding. So, how can you become ignorant again to benefit your readers?
Test your writing. Share your documentation with someone who doesn't know the topic. Revise the areas of your writing that confuse this person.
Define terms. If a term, concept, or process is critical, introduce it before you rely on it. No exceptions.
Properly order the process. Build knowledge in a sequence that makes sense.
Write simple, clear sentences. Your readers will learn faster when you remove unnecessary words and complex sentence structures.
The Wrap
Colonel Graff didn’t hand Ender a gun and say, “Figure it out.” And yet, many explanations fail because they assume too much and guide too little.
Bad technical writing isn’t bad solely due to overusing jargon — it can be bad because it forgets the reader. It assumes knowledge that hasn’t been introduced. It skips intuitive steps. It overwhelms instead of informs.
If your audience isn’t getting it, it’s not because they’re incapable — it’s because you’ve lost sight of what it was like to be in their place.
So before you hit publish, ask yourself:
Am I writing for my past self, or for someone who already knows what I know?
Am I making my reader feel capable, or like they don’t belong?
The best writing — the writing that sticks, the writing that matters — meets people where they are and guides them forward.
If your audience doesn’t understand what you wrote, that’s not their failure.
It’s yours.