When Thoughtful Writing Starts to Feel Suspicious
Something strange is happening to how we read online
For the love of clarity, can we all take a breath on the finger-pointing about AI written content?
Let’s take a step back for a minute and think about how we’ve come to the place where we are. We’ve spent years compressing language into shorthand. I’m not talking about just abbreviations like “IMO” or “FYI,” but an entire style of communication built for speed, efficiency, and low friction. I’ve received professional emails that look like they were typed with one thumb while walking to the car. And to be honest, our emails sound more like calendar reminders than human thought, and comments have been reduced to emojis, fragmented sentences, or a quick, “this!”.
None of that is necessarily bad. In the world we live in, it’s practical and adaptive. Frankly, it’s what happens when communication becomes continuous instead of intentional. But somewhere along the way, the shortcut has become the expectation. It’s no wonder we’ve just become used to it. But now, when someone takes the time to write something fully formed with complete thought; a real paragraph, an idea with edges, the reaction isn’t always positive engagement. Sometimes it’s suspicion like “this feels like AI. No one writes like this anymore. This sounds too polished”.
We’ve reached a point where even typography choices can feel like signals. I’ve caught myself overthinking things I never used to, like whether the font on my website, Address Sans Pro, uses a dash that’s a little longer than Calibri’s, but not quite the universally suspicious em dash.
That reaction says less about the technology and more about what we’ve trained ourselves to recognize as “normal.” We’ve gotten used to language and communication that’s unfinished, ideas that trail off, and messages designed to keep moving, not to land. So when writing slows down and breathes, and when it’s reflects - it can feel unnatural, almost out of place in our feeds that are optimized for momentum. And the irony is that some of what gets labeled as “AI writing” isn’t actually artificial. Maybe it’s just complete, like full sentences and a clear transition, or a thought that doesn’t collapse into a punchline or a CTA. In this new culture of fragments, it seems like coherence stands out, so we question it.
I should probably say something else out loud here, because it matters to this conversation. I currently produce around a dozen long form pieces of content in a year. Not because I lack ideas, but because the way I think and listen doesn’t lend itself to constant output. When I wrote a recent long-form piece on “Buy Now, Pay Later”, the rough draft ran north of 11,000 words. Not because it needed to be that long, but because that’s how the thinking works before it tightens. It starts loose, and trust me it wanders. It follows threads that don’t all make the final cut. In this case, the final piece ended up around 1,900 words.
I also still write long form content by hand with a pencil. To be specific, a gray stainless KOH-I-NOOR Rapidomatic 0.7mm that’s followed me around for years. In office environments, that habit used to earn me a good amount of grief, but all in good fun. Writing slowly forces me to listen longer; to the idea, to the counterpoint, to the thing I think I believe versus what actually holds up once it’s on paper. There is just something about feeling the lead on the paper. And sometimes those drafts turn into something worth sharing. But sometimes they don’t when I really read back through them. Or they can even turn into a couple of shorter form blogs, or lead to a campaign idea.
I’ll even occasionally write shorter pieces with a fountain pen, because it keeps me from rushing past my own thoughts. I write more like a storyteller than a headline writer. That means sentences have a setup, and it takes a bit for ideas to arrive in context. Words some people would call superfluous because they aren’t optimized for speed, or “get to the point” quickly.
That approach doesn’t work everywhere. I wouldn’t even begin to use it in a status update or a quick blog meant to be skimmed between meetings. But when a piece runs 2,000 words or more, it isn’t about trying to win attention … it’s about trying to earn it. Those kinds of pieces aren’t meant to move fast. They’re meant to hold together. Which is why it’s strange to me when thoughtfulness itself gets flagged as artificial.
Short-form communication has trained us to conflate effort with inauthenticity. If it looks like someone tried, we assume it must be manufactured. If it sounds considered, we assume it can’t be spontaneous, and we’ve mistaken roughness for honesty and polish for performance. But real thinking isn’t always rough. Sometimes it’s careful, quiet, and takes a few paragraphs to say what actually needs to be said. I don’t think that makes it fake – just deliberate.
This is where I think some of the AI conversation gets lazy. Yes, there’s a flood of cut-and-paste content out there. You can usually spot it quickly, it can be shallow or have a hollow confidence, and usually it can be absence of a true point of view. But lumping all thoughtful writing into that bucket flattens something important: the difference between automation and intention.
Way before language models, people wrote letters, essays, memos, and arguments that held together. They revised and reread, and they cared how something landed. The fact that those qualities now feel novel says more about how our habits have changed than how machines have. I still write thank you notes by hand.
There’s also a social dimension to this. In fast feeds, effort can feel like a violation of the unspoken rules. You’re supposed to keep it light, quick and skimmable. When someone shows up with a longer thought, it can feel like they’re breaking the tempo, and asking for more attention than the room agreed to give. What worries me isn’t that AI is changing how people write. It’s that we’ve become so accustomed to shorthand that we’re starting to distrust depth. We’ve normalized communication that hints at ideas instead of completing them, and now feel odd when someone actually follows one through. Thoughtful writing doesn’t need defending. It just needs some room, and maybe a bit of grace from readers Some things still take a minute to unfold, and if feels odd, it might be worth asking why.
Don’t get me wrong, long rambling writing has it’s place, and maybe it’s not tailored for some audiences. Quick to the point writing also has it’s place, particularly in copywriting. But, maybe give folks a little grace when evaluating someone’s writing. Even if someone used AI to write a piece, they technically needed to prompt AI to construct it. Maybe the real issue isn’t how something was written, but how willing we are to sit with it.
I think one of the unintended side effects of speed and automation is that we’re producing more words while listening less, to customers, to context, and to culture. That idea sits at the center of One Ear Up, One Ear Down, where I explored why good strategy still requires human observation, and why attention itself has become a competitive advantage.