The Rise of the ‘Humanity Premium’ in Digital Communication
For decades, the gold standard of professional communication was flawlessness. Perfect grammar, precise punctuation, and a polished tone were the hallmarks of competence. Whereas, the explosion of generative AI has flipped this script. Today, a perfectly crafted email often triggers a “red flag” for the recipient, signaling that the sender didn’t actually write the message.
We are entering an era of the “humanity premium,” where intentional imperfection is becoming a valuable asset. When every inbox is flooded with what founder Ben Horwitz calls “AI slop,” the presence of a typo or a casual phrasing becomes a proxy for authenticity. It proves there is a living, breathing person on the other end of the screen.
Decoding the ‘Anti-Grammarly’ Movement
This shift has given rise to a new category of tools designed to “un-AI” our writing. A prime example is Sinceerly, a Google Chrome extension that acts as an “anti-Grammarly.” Rather than scrubbing away errors, it injects calculated mistakes to make AI-generated text appear genuinely human.

The tool operates through three distinct intensity levels to match the desired persona:
- Subtle: Light adjustments to remove obvious AI patterns.
- Human: A more casual approach that introduces typical human errors.
- CEO: The most aggressive mode, which ignores correct punctuation and adds the classic “Sent from my iPhone” signature to mimic the brevity of a busy executive.
By targeting the specific linguistic markers that AI tools typically leave behind—such as the em dash—these tools allow users to bypass the subconscious bias against “too-perfect” text.
Why ‘Perfect’ is the New ‘Fake’
The pushback against AI-generated content isn’t just about aesthetics; it’s becoming a matter of professional and artistic credibility. The risks of sounding “too AI” are becoming tangible. For instance, the major publisher Hachette recently dropped the novel Shy Girl following allegations that the work was AI-generated or poorly written.
This creates a strange paradox: we employ AI to increase efficiency, but we must then use more AI to hide the fact that we used AI. This “ouroboros” of tech reflects a growing cultural exhaustion with synthetic content. When perfection is automated, the only way to signal effort and sincerity is through the very flaws that AI is designed to eliminate.
The Future of Authenticity and AI Obfuscation
As AI detectors become more sophisticated, the battle between generation and detection will likely evolve into a battle of obfuscation. We can expect to observe a rise in tools that don’t just add typos, but analyze the specific writing style of an individual—their unique quirks, favorite slang, and common mistakes—to create a digital “human” twin.

the integration of these tools directly into workflows, such as the Sinceerly integration with Gmail, suggests that “humanizing” will become a standard final step in the writing process. The goal is no longer to write perfectly, but to write believably.
Frequently Asked Questions
What is Sinceerly?
Sinceerly is a Chrome extension designed to make AI-generated or human-written emails sound more human by removing AI “tells” and adding natural errors.
How much does it cost?
The tool offers a free tier providing three email rewrites. A Pro plan is available for $4.99 per month, which includes unlimited rewrites, instant mode switching, and cached results.
What is “CEO mode”?
CEO mode is a setting that renders text very casual, removes correct punctuation, and appends “Sent from my iPhone” to the message.
What do you think? Does adding intentional typos make an email experience more authentic, or is it just another layer of AI deception? Let us know your thoughts in the comments below or subscribe to our newsletter for more insights into the future of AI.
