From Ladders to Landscapes

The Ladder and the Dream

Hugh Hayden’s ladders — impossible to climb — made me think about our ambition to rise and the limits of upward motion. His Living Room: Orlean, VA at Cooper Hewitt — an entire room rocking gently on its base — felt like a mirror of my life as a nomad, caught between motion and balance, learning how to be at home in movement.

Like Hayden, who shifted from architecture to full-time art, I’ve also crossed from leading in tech to integrating creativity and coaching as new ways of building meaning. His work reminds me that the structures we build — in careers or in life — are often the very ones we must eventually outgrow.

The Shift: From Structure to Movement

In the summer of 2023, while working with a tech startup based in the Bay Area, I joined two artist residencies in Mexico City — right after my first experience living and working remotely as a digital nomad in Tulum. It was the beginning of something I couldn’t yet name. Later that fall, I spent several months in Leipzig, Germany, continuing to develop my art practice. Between those residencies, something inside me began to shift — the rhythm of my life, once defined by growth metrics and OKRs, began to feel more like a creative process.

I was learning to move differently: less like an executive, more like an artist, more like myself.

The American Dream had taught me how to climb. The Global Dream was teaching me how to move.

When Everyone Zigged

In the startup world, we learn to move fast, scale quickly, and optimize relentlessly. But art — and life beyond ladders — moves at another pace. It asks for patience, discomfort, and the courage to sit inside uncertainty.

When everyone zigged toward stability amid rising uncertainty and volatility, I zagged toward movement.

Not to escape ambition, but to redefine it.

Not to reject structure, but to design my own.

I began building a life that spanned continents: roughly 40% in the Americas (North and South), 40% in Europe, and 20% in Asia — with Seoul as my anchor and point of return. My work as an artist, coach, and entrepreneur became less about arrival and more about rhythm — an ecosystem instead of a hierarchy.

From Ladders to Landscapes

When I started writing this, I was in Seoul — my home base, where I feel nurtured and restored, even during short stays. Now I’m in New York again, back in the pulse of a city that never stops moving. Between Seoul, where I return to ground and restore myself, and New York, where I stretch into new ideas and conversations, I look back on Hayden’s ladders and realize how prophetic they are. They remind me that success, when too rigid, can trap the same ambition it was meant to elevate.

I no longer want to climb; I want to expand.

I think of my path now not as a ladder, but as a landscape — one that stretches across fields, oceans, and disciplines. There’s no single summit, no single dream. Just movement, curiosity, and the ongoing cycle of growth, decay, and regeneration.

The American Dream taught me how to climb; the Global Dream taught me how to move.

And when everyone zigged, I learned how to zag — not to resist the current, but to find my own rhythm within it.

Closing Reflection

Maybe that’s what Hugh Hayden’s work is really about — ladders reimagined, no longer for climbing but for reflection, transformed into art, metaphor, memory. I see my own life that way now — built, unbuilt, and rebuilt again.

Each pivot, each country, each creation — not a detour, but another form of becoming, another rung turned into root.

If you find yourself standing at your own threshold — sensing the pull of change, wondering what the next shape of your becoming might be — I’d love to explore it with you.

Coaching begins with a simple conversation, a chemistry call, to see what might unfold from here.

— Jay