The Time I Used ChatGPT to Dress Myself
On April 9th, 2024, I did something I’ll forever be (slightly) ashamed of.
On that fateful morning, I opened my laptop and typed the most unforgivable ChatGPT prompt to date:
“should i wear short sleeves today its supposed to be like mid sixties but i live in sf so”
Yeah. I asked artificial intelligence to decide if I needed a jacket.
Why That Question Still Haunts Me
I don’t regret it because of the grammar (though, sure, you can judge me for that too).
I regret it because, against the insurmountable odds of San Francisco’s famously fickle climate, I’ve somehow managed to dress myself thousands of times without an LLM to hold my hand.
But in that moment, I let the allure of AI short-circuit my own intuition. I outsourced a decision I absolutely (probably? maybe??) could’ve made myself.
The Trap of Outsourcing the Obvious
Ever asked an AI a question you could answer yourself? Maybe drafting a quick email, asking for an opinion, or clarifying something you could’ve worked out with a bit of thought?
It’s tempting because AI is fast, frictionless, and eager. But that’s exactly where the risk lies.
The World Economic Forum’s Future of Jobs Report predicts creativity will be one of the most important skills of the next decade. And questions like mine explain why: we already have evidence that over-reliance on AI can cause cognitive atrophy. By handing over even trivial struggles with uncertainty, we dull the very muscles that help us think originally and act decisively.
Why Wrestling With Uncertainty Matters
Uncertainty is uncomfortable, but it’s also essential. Wrestling with the “friction” of not knowing is:
Where originality is born. Without grappling, our ideas stay recycled rather than breakthrough.
How we keep our judgment sharp. Leaders and creators need discernment to know when AI’s output is inspired and when it’s merely convenient.
What keeps us human. Machines can process data. Only people can sit with ambiguity long enough to turn it into meaning.
A Reminder for Leaders and Creators
AI is an extraordinary thought partner. I use it daily in my own work as a poet and innovation keynote speaker. But its power isn’t in replacing our thinking — it’s in provoking it.
If we allow AI to carry all the weight, we lose the very creativity, originality, and discernment that make us valuable as leaders, colleagues, and people.
So the next time you’re tempted to let ChatGPT tell you whether to grab a jacket — pause. Wrestle with the uncertainty yourself. Because those tiny, trivial battles aren’t wasted effort. They’re training for the kind of breakthrough thinking the future will demand.
Final Thought
In the end, creativity isn’t just about solving problems. It’s about embracing uncertainty, bending it into something new, and shaping meaning where none existed before. That struggle is not a bug of being human — it’s the feature.