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One of my favorite songs is Upside Down by Jack Johnson, written and produced for the Curious George movie in 2006. It's soft, sunny, and deceptively simple - a reminder to stay curious, question limits, reject conformity and embrace wonder even as life gets more structured and serious. I didn't fully appreciate the message until recently, when I met someone in Indonesia who seems to move through the world upside down. Open, playful, and unwilling to accept life's usual constraints. Being around her makes the world feel larger and more alive.

Childhood was the last time we saw the world clearly. Not what should be, but what could be. Back then, nothing felt fixed. Every object was a mystery and every rule negotiable. Then adulthood arrives, and with it comes consensus reality - the "right side up" view. You stop questioning because you're supposed to already know things. You stop exploring because you're supposed to be efficient. You trade wonder for correctness without ever noticing what you've lost.

Curiosity is the only reliable way to break that trance. Consensus is comfortable but blinding. It tells you where the edges are and quietly convinces you not to look past them. Curiosity, by contrast, interrupts everything. It makes you poke, wander, and ask both "why" and "why not." Ambiguity is where the interesting things hide. Kids treat uncertainty as texture, the fun part, while adults treat it like a threat. But in relationships, creative work, and life more broadly, the people who thrive are the ones with a high tolerance for not knowing.

That's what "upside down" means to me. Not chaos, but intentional openness and wonder. A willingness to challenge assumptions. A refusal to let the world grind down your sense of curiosity. Hanging from a tree branch, figuratively or literally, just to see how things look from a new angle. It's a philosophy that feels almost radical now, especially in tech.

The modern internet is engineered to flatten wonder before it can even form. Algorithms predict what we want, feeds compress nuance, and online discourse rewards consensus over curiosity. The tech industry mirrors this with its endless playbooks and default narratives on "how things are done." Building companies, investing, raising money and shipping products. Everyone is sprinting from one certainty to the next, as if certainty itself were the product.

But the people who actually shift the direction of industry never operate that way. They're the ones who stay childlike, not childish. Open, questioning, noticing. They play with ideas other people dismiss. They explore instead of optimize. Search engines, marketplaces, social graphs, blockchains, LLMs - these were all upside down ideas before they became inevitable. But inevitability has a way of making people lazy. Now, more than ever, we need to invert things again.

That's the paradox - curiosity feels like a luxury in tech, when it's actually the only competitive advantage left. Competence is abundant, playfulness is scarce. Childhood curiosity is underrated probably because it looks inefficient. Wondering and questioning things are instincts that the tech industry trains out of people. Play becomes frivolous because it's not economical, but the entrepreneurs who keep their childlike intuition alive and protect their sense of wonder from the machinery of adulthood have an edge.

Which brings me back to Upside Down. The chorus - "Who's to say what's impossible?" - is more than a lyric but a philosophy of motion. A nudge to find the things "they say just can't be found." A reminder that life expands when you stop living strictly upright. Curious George is constantly exploring and rule-bending. Both the song and the movie frame life as an adventure where rethinking and challenging assumptions leads to discovering new joy, love, and connection with the natural world and one another. That's the best way forward, for all of us. Upside down.

027

One of my favorite songs is Upside Down by Jack Johnson, written and produced for the Curious George movie in 2006. It's soft, sunny, and deceptively simple - a reminder to stay curious, question limits, reject conformity and embrace wonder even as life gets more structured and serious. I didn't fully appreciate the message until recently, when I met someone in Indonesia who seems to move through the world upside down. Open, playful, and unwilling to accept life's usual constraints. Being around her makes the world feel larger and more alive.

Childhood was the last time we saw the world clearly. Not what should be, but what could be. Back then, nothing felt fixed. Every object was a mystery and every rule negotiable. Then adulthood arrives, and with it comes consensus reality - the "right side up" view. You stop questioning because you're supposed to already know things. You stop exploring because you're supposed to be efficient. You trade wonder for correctness without ever noticing what you've lost.

Curiosity is the only reliable way to break that trance. Consensus is comfortable but blinding. It tells you where the edges are and quietly convinces you not to look past them. Curiosity, by contrast, interrupts everything. It makes you poke, wander, and ask both "why" and "why not." Ambiguity is where the interesting things hide. Kids treat uncertainty as texture, the fun part, while adults treat it like a threat. But in relationships, creative work, and life more broadly, the people who thrive are the ones with a high tolerance for not knowing.

That's what "upside down" means to me. Not chaos, but intentional openness and wonder. A willingness to challenge assumptions. A refusal to let the world grind down your sense of curiosity. Hanging from a tree branch, figuratively or literally, just to see how things look from a new angle. It's a philosophy that feels almost radical now, especially in tech.

The modern internet is engineered to flatten wonder before it can even form. Algorithms predict what we want, feeds compress nuance, and online discourse rewards consensus over curiosity. The tech industry mirrors this with its endless playbooks and default narratives on "how things are done." Building companies, investing, raising money and shipping products. Everyone is sprinting from one certainty to the next, as if certainty itself were the product.

But the people who actually shift the direction of industry never operate that way. They're the ones who stay childlike, not childish. Open, questioning, noticing. They play with ideas other people dismiss. They explore instead of optimize. Search engines, marketplaces, social graphs, blockchains, LLMs - these were all upside down ideas before they became inevitable. But inevitability has a way of making people lazy. Now, more than ever, we need to invert things again.

That's the paradox - curiosity feels like a luxury in tech, when it's actually the only competitive advantage left. Competence is abundant, playfulness is scarce. Childhood curiosity is underrated probably because it looks inefficient. Wondering and questioning things are instincts that the tech industry trains out of people. Play becomes frivolous because it's not economical, but the entrepreneurs who keep their childlike intuition alive and protect their sense of wonder from the machinery of adulthood have an edge.

Which brings me back to Upside Down. The chorus - "Who's to say what's impossible?" - is more than a lyric but a philosophy of motion. A nudge to find the things "they say just can't be found." A reminder that life expands when you stop living strictly upright. Curious George is constantly exploring and rule-bending. Both the song and the movie frame life as an adventure where rethinking and challenging assumptions leads to discovering new joy, love, and connection with the natural world and one another. That's the best way forward, for all of us. Upside down.