Shadow as the Trailhead to Treasure

For much of my life, I believed aliveness was synonymous with joy. With excitement. With enthusiasm, creativity, and expansion. Aliveness, in my mind, was a glow of energy in the “positive” direction.

But what I’ve discovered is that aliveness has a much wider range.

Aliveness is not just the thrill of inspiration—it’s also the quickening of fear, the ache of grief, the heat of anger, the pulse of anxiety in the body. Aliveness shows up not only in what feels light and expansive, but also in the places that constrict, that unsettle, that draw us into shadow.

And if we’re willing to follow it there, into those shadowy places, there’s treasure waiting.

The Ending That Began It All

A year ago, I ended a working relationship that had once felt deeply alive. I was employee number one at a tech startup, working side by side with the founder to build an AI product from scratch. In the beginning, our collaboration was full of excitement and mutual trust. But over time, shadow crept in.

Creative tensions became unresolvable differences. Leadership philosophies clashed. Personal challenges spilled into our working dynamic. Eventually, I had to name my dealbreakers—the trust, confidence, and shared belief in the product I needed in order to lead well. When she couldn’t say yes, we ended the partnership.

That ending was painful. It brought sadness, constriction, and a heavy fog of fear about my future. But it also opened the door to something else: seven months of stepping away from work altogether.

Listening by Doing Nothing

At first, those months didn’t feel like a gift. Inside me, there was an Energizer Bunny of anxiety—restless, relentless, demanding I figure out what was next, how I’d survive, how I’d make sense of it all.

Normally, my Type A instincts would have jumped into action. Hustle, strategize, fix. But instead, I did something different. I did nothing.

I played video games. I went on long walks. I spent time in nature. I sat in silence. And I listened. Not listening for quick answers or resolutions, but simply listening to the pulse of anxiety, to the restless aliveness inside me.

The Map of Shadow

The video game I happened to be playing was The Legend of Zelda: Tears of the Kingdom. And somewhere along the way, it became a mirror.

In the game, new parts of the map are dark at first. Shadowy. Unknown. But when you travel to them, spend time there, and light the towers, the terrain reveals itself. You can see what’s there, and you can return to it.

That was exactly what was happening in me. The dark, anxious places were unlit parts of my inner map. By spending time there—not rushing past them, not forcing them into light—they began to reveal themselves. Slowly, parts of my own heart lit up again.

Remembering the Dormant Parts

As the map lit up, I reconnected with parts of myself I had left dormant in the startup and corporate worlds. My creativity stirred. I found myself dreaming with friends again, re-exploring spiritual pathways, imagining what I wanted for my life and for the world.

I began to glimpse a different kind of community, rooted in emergence. A vision of new paradigm leadership. Post-capitalist collectives. Creative ecosystems where time, money, and human connection flow in life-giving ways.

What started as shadow and constriction became a portal into vision and possibility.

The Wisdom Beneath Anxiety

One of the deepest truths I uncovered in those months was about my relationship with money and time. My anxiety wasn’t just about uncertainty—it was my body’s wisdom speaking. It was revealing the cost of living inside a pattern of obligation and constriction, a relationship with money and time that drained the life out of me.

By listening—really listening—to that anxiety, I could see it for what it was: a messenger. A call to imagine something new.