How an Ancient Spiritual Roadmap Helped Me Discover New Lands

For 20 years, I lived a lie—and I didn’t even know it.

From the outside, my life seemed picture-perfect: a respected career, a sense of purpose, and the admiration of those around me. But beneath the surface, there was a gnawing disconnect, a quiet whisper that something wasn’t quite right. I tried convincing myself otherwise, but deep down, I knew the truth: I was pretending to be someone I wasn’t meant to be.

For most of my adult life, I was a Rabbi. On paper, it seemed like the ultimate fulfillment—a role steeped in spiritual connection, meaning, and service. And to be fair, there were moments of true beauty and purpose. But something always felt off.

I would give sermons, counsel congregants, and guide others in their spiritual journeys, but it always felt as though I was operating behind a glass wall. I could see the world clearly, yet I couldn’t fully engage with it. Something was missing, and I didn’t know how to name it.

Finding the Map in the Dark

Eventually, after years of wrestling with anxiety, uncertainty, and a sense of disconnection, I stumbled upon an ancient roadmap—the Enneagram.

This nine-pointed system wasn’t just another personality tool or self-help fad. It was a lifeline. It helped me uncover the unconscious patterns, fears, and desires that shaped how I moved through the world. It showed me how my programming, conditioning, and even generational trauma had built invisible barriers around me.

The Enneagram didn’t just tell me what I was doing wrong; it showed me why. And more importantly, it illuminated a path forward—a way to break free from the invisible prison I had trapped myself in.

Losing Sight of the Shore

Discovering the Enneagram was like what Marcel Proust described: “The journey of discovery consists not in seeking new lands, but in having new eyes.” But gaining new eyes isn’t easy. To discover new lands, you have to lose sight of the shore for a while.

As I delved deeper into the Enneagram, I began to uncover my True Self—hidden beneath layers of fear, desire, and societal expectations. It wasn’t an overnight transformation. It was messy, uncomfortable, and at times terrifying.

But it was also liberating.

From the Cave to the Light

Plato’s Allegory of the Cave describes prisoners who spend their entire lives in darkness, mistaking shadows on the wall for reality. That was me.

I had been living in the cave for so long that it felt normal. But when I finally stepped out—when I let go of the life I thought I was supposed to live—I felt the warmth of the sun, heard the songs of the birds, and experienced a fullness of life I never thought possible.

That’s not to say life suddenly became perfect. Far from it. But even in the messiness and challenges, I found a sense of clarity, purpose, and aliveness.

The Process of Transformation

The journey wasn’t easy, but it was simple. It began with the Enneagram, which helped me see the shadow and light within myself. With this awareness, I could stop reacting based on old programming and start responding skillfully to life’s challenges.

Once I uncovered my True Self, I realized something even greater: I had a unique purpose—a Soul Contract—that I was meant to fulfill.

Reconnecting with spirit and seeking guidance from something greater than myself became essential. I let go of the barriers that kept me stuck and embraced a bigger, brighter world filled with possibilities.

What Changed? Everything.

Today, my life looks completely different.

I walked away from being a Rabbi, not because it was a bad path, but because it wasn’t my path. I stepped into a life of deeper meaning, more authentic relationships, and a sense of purpose that feels true to who I am.

You don’t have to leave your career, change your identity, or make radical external shifts to experience this transformation. The real work happens on the inside.

The Key to Unlocking Your Prison

If you’ve ever felt stuck, disconnected, or trapped by invisible walls, I want you to know this: you don’t have to stay there.

The Enneagram isn’t just a tool; it’s a key. It can help you unlock the prison of your old habits and open the door to a life of clarity, purpose, and meaning.

This work isn’t easy, but it’s worth it. It’s how you rise—not just as a man in midlife, but as a fully realized human being.

If you’re ready to step out of the cave and into the light, join us at Man UPrising. Together, we’ll rise into the second half of life with purpose, authenticity, and a new way of seeing the world—and ourselves.