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The Uncomfortable Pivot: Why Feeling ‘Weird’ With AI is Your New Competitive Advantage
I’ll be honest: lately, my morning routine feels broken. For fifteen years, my “flow” was a sacred, linear process. I’d grab a coffee, open a blank document, and wrestle with an idea until it took shape. But recently, I’ve started inviting a “Co-Intelligence” into that process, and it feels… wrong. It’s jittery. It’s non-linear. It feels like I’m cheating, or worse, like I’m losing the “soul” of my work.
But here is the contrarian take: If you feel weird working with AI, you are probably the only one doing it right.
Most people are trying to shoehorn AI into their existing, comfortable workflows. They use it as a faster Google or a glorified spellcheck. They are trying to make the future fit into the past. But as Ethan Mollick recently highlighted in a fascinating Wharton discussion, we are currently in an era of “recursive self-improvement” where the old playbooks aren’t just outdated—they’re obstacles.
Insight 1: The End of the “Human Middleware” Era
For decades, the standard workflow was built on apprenticeship and incremental tasks. You give a task to a junior, they “middleware” the data into a report, and you review it.
Today, that “middle” has evaporated. Mollick points out a chilling reality: interns aren’t becoming “AI native” by using these tools; they are often just “pasting questions into Claude” to bypass the learning process. This creates a massive organizational risk—a “skills gap” where the next generation of leaders isn’t actually learning how to think.
The “weirdness” you feel is the friction of realizing that judgment is now more valuable than execution. We are moving from being “doers” to being “curators of taste.” When a machine can churn out a software package or a business simulation in minutes that used to take a 14-person team two years, your value isn’t in the labor; it’s in the agency and taste to know which version is actually “right.”
Insight 2: The Fallacy of the “AI Native”
We often assume the “kids” will figure it out. We look at Gen Z and expect them to be the pioneers. But Mollick challenges this: there is no such thing as an AI native because the technology is moving too fast for anyone to “settle” into it.
In fact, seniority might be an advantage again. Why? Because to use AI effectively, you need Deep Knowledge. You need to know a field well enough to realize when the AI is “hallucinating” or providing a generic, “slop” answer. If you don’t feel a bit of “imposter syndrome” right now, you aren’t paying attention. The most successful leaders—like those at the Norwegian Sovereign Wealth Fund—aren’t just “using” AI; they are forcing themselves to “put hands on keyboards” and relearn the very basics of logic and code.
Insight 3: From ROI to R&D (The Stoic Reframe)
In traditional business, we hate waste. We want ROI. But we know that in a period of exponential change, the only way to avoid obsolescence is to embrace deliberate inefficiency.
Mollick suggests that organizations must invest in R&D that is designed to fail. This is a hard pill for the mind to swallow. We are used to “efficiency gains.” But if you only use AI for efficiency, you get “10 times more generic memos.” Real competitive advantage comes from using AI to do something “impossible”—entering a new market or building a “software dark factory” where humans never even touch the code.
Final Thought: Lean into the Friction
Stoicism teaches us that “the obstacle is the way.” The “weirdness” you feel is the sensation of your mental models being rewritten in real-time.
Don’t try to make AI fit your “natural” style. Your natural style was built for a world that no longer exists. Instead, treat AI as a “Co-Intelligence” that requires you to be more of a philosopher-king than a manager. Focus on your Taste, your Agency, and your Deep Knowledge.
The goal isn’t to work with AI in your usual way. The goal is to let AI break your usual way so that something more resilient can be built in its place.
Watch the full discussion here: Preparing for an AI-Driven Future in Business – Wharton in Focus
Cheers 🥂