The Deepening
Where Success Meets Soul
A container to explore the tension between who you’ve been and who you’re becoming, and emerge with expanded potential, possibility, and a renewed sense of purpose that changes not just how you lead—but how you live.
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The Journey of Descent
Throughout human history, the journey of descent has been central to transformation.
In ancient traditions, rites of passage often included a period of separation, descent into the unknown, and eventual emergence. It was understood that to create new life, one had to first let go of the familiar and descend into the depths.
The Greeks called it katabasis—a journey downward into the underworld to confront one’s shadow and uncover hidden truths.
Indigenous cultures sent initiates into the wilderness to face themselves, returning transformed with the gifts of their journey.
These traditions honored a paradox we’ve largely forgotten in today’s relentless climb: at some point, the way up is the way down.
The Shift You’re Feeling
You’ve worked hard to get here—chasing milestones, pushing through barriers, and conquering challenges.
But something’s changing.
The strategies that once fueled your success—the striving, doing more, and trying harder—no longer carry you like they used to.
It’s not that these things are no longer important, but they no longer feel like the whole story.
You’re not where you want to be, but you can’t go back to where you were.
There’s a sense that something is missing, an ache you can’t quite name.
You feel like you’ve hit a ceiling—stuck in the in-between.
This is where the deepening begins.
My Descent and Deepening
I know this paradox all too well.
For years, I threw myself into success with everything I had—West Point, the NFL—believing that just one more achievement would make me whole.
On the outside, I had it all. I was thriving. But on the inside? I was barely holding it together.
I was surviving successfully—but I was still surviving.
The life I worked so hard to build felt like a burden to carry, not a life to enjoy.
I was externally accomplished but internally restless—burned out, stuck, perpetually dissatisfied, and deeply unfulfilled.
The most frustrating part?
Deep down, I knew there was more. Something was missing, and I could feel it.
But, the harder I chased, the further it seemed to drift out of reach.
The Work: Holding The Tension
For me, it took life bringing me to my knees—a divine ambush.
In my relentless pursuit of more, I eventually found myself the type of tired more sleep doesn’t solve. I woke up not just with tired eyes, but a tired soul.
The hustle I once wore like a badge of honor—the same hustle that earned applause and admiration—had become a distraction.
At some point, it stopped being ambition, and it had become the avoidance of stillness.
Only when I stopped running did I see the answers weren’t "out there. They weren’t in the next milestone or the next “win.”
They were waiting for me at the bottom of an internal deepening.
This work isn’t about rushing to fix, solve, or figure it all out.
It’s about creating the inner capacity to hold the vulnerable tension of the in-between—the space between what was and what will be—without retreating to what feels safe and familiar.
In a world that worships speed and results, it takes courage to embrace a season of growth that doesn’t look ‘productive’ from the outside—choosing stillness over pushing through.
But when we do, we create the space for expanded potential, possibility, and purpose to emerge not from striving—but from surrendering.
The Crossroads We All Face
There comes a time when the familiar strategies—doing more, trying harder—no longer take us where we want to go.
The next phase of our growth isn’t found by pushing forward but by learning how to resist less.
This crossroads can feel unsettling, even disorienting, because it contradicts everything we’ve been taught about success.
This is the threshold we’re standing at, the pause between what was and what can be.
This in-between place—what some call a liminal space—though uncomfortable, holds transformative potential.
It’s the sacred threshold where we confront the limits of the life we’ve been living and open ourselves up to the limitless possibilities of what can be.
Here, we’re called to resist the pull of old patterns—the busyness, the striving, the need to figure it out—and instead build the capacity to hold the tension.
To sit with ambiguity, to treasure vulnerability, to trust the unknown and to learn how to work with your becoming—not against it.
It is here the space is born to emerge with expanded potential, possibility and a renewed sense of purpose.
This is how you uncover the truth waiting all along:
You are the answer you’ve searching for.
The Invitation:
Open The Treasure Chest
As Pete Holmes, my favorite comedian, so beautifully said, “We are like beggars sitting on a treasure chest full of gold coins, asking for spare change.”
The Day of Deepening is an invitation to open that treasure chest.
To stop striving for what you already have and unlock a life that no longer feels like a burden to carry, but a gift to be experienced.
What You Can Expect
This isn’t a container of structured agendas or rigid frameworks. It’s a sacred container—crafted intentionally but held lightly—where intuition, authenticity, and presence lead the way.
As we work together, you’re invited to set aside the need to control, to solve, or to achieve. You’re encouraged to let go of outcomes and enter the flow of what wants to emerge.
Together, we’ll move through conversations, reflections, and experiences designed to open doors within you—not force them.
We’ll explore the questions you haven’t yet asked—the ones that reveal the wisdom you haven’t yet accessed.
We’ll use a blend of tools—modern mysticism, poetry, parts work, ceremony, and somatic practices—to guide and support your day of deepening.
These practices are not here to “fix” you but to hold space for what needs to unfold.
Together, we’ll also craft simple, intentional practices to carry the insights from this experience into your daily life, creating a foundation for your new way forward.
The only requirement is a willingness to show up with an open heart as this experience will give you what you’re ready to receive.
If this speaks to you, we’ll start with your central question and see where the deepening leads us.
Who Is This For
It doesn’t matter if you’re a C-suite leader, stay-at-home parent, or professional athlete—this experience is for those who sense there’s something deeper available.
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Despite all you’ve accomplished, there’s a quiet ache within—a longing for something more meaningful, more aligned, more real.
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The familiar no longer fits, but the path ahead feels unclear, leaving you standing in the tension of transition.
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You sense this pause holds wisdom—a chance to deepen, to listen, and to allow what’s next to emerge naturally, without force.
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You know it’s time to invest in your inner world so you can show up with renewed clarity, energy, and purpose.
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You’re ready to explore a different way of leading—one that feels lighter, more authentic, and sustainable.
How Is This Different
Most growth-oriented programs focus on and reinforce the qualities that drive traditional upward success.
This approach isn’t wrong—it’s just incomplete.
The work of deepening doesn’t abandon ambition—it complements it by guiding you inward.
It’s about creating space to access untapped potential and possibilities that can’t be reached through sheer effort alone.
Instead of grinding harder, it’s about discovering a different way of being—one that transforms not only your capacity for success but also your experience of it.
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Traditional growth programs push you to strive for more through effort and control. The Day of Deepening invites you to embrace surrender—not as giving up, but as opening up to what’s already within you, allowing transformation to emerge naturally.
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Growth containers often focus on fixing perceived flaws or deficiencies. This work teaches you to honor and feel what arises without judgment, discovering that your so-called flaws are pathways to deeper connection and self-acceptance.
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Instead of forcing outcomes through rigid strategies and effort, this experience shows you how to tap into the gentle, intuitive flow of life, where your actions are guided by alignment rather than sheer willpower.
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While many programs focus on logic, strategy, and intellectual frameworks, The Day of Deepening helps you descend into the heart space, where deeper truths and authentic clarity reside.
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Success is no longer solely about performing for validation but about being fully present in your work and life. This shift creates a success that feels deeply satisfying rather than fleeting or hollow.
Choose Your Deepening Experience
1-on-1 Deep Dive Into The Deepening
A bespoke journey for those ready to go deeper. Together, we’ll navigate the tension between who you’ve been and who you’re becoming, creating space for transformation over 3-6 months.
The Day of Deepening
A soul-centered, day-long experience designed to guide you through the in-between—where you’ll learn the wisdom of the descent and emerge with expanded potential and purpose.
The Descent Collective (Coming Soon)
A group coaching container where we explore the forgotten path of descent, embracing the discomfort of the unknown to uncover collective wisdom, personal transformation, and the courage to rise into a life that feels whole and true.
The Ripple Effect
In ancient traditions, the journey of descent wasn’t just for the individual—it was for the whole community. Those who said yes to the call returned with gifts: deeper wisdom, renewed strength, and clarity that benefited everyone around them.
As much as this Deepening will breathe new life into your burned-out heart and tired soul, it doesn’t end there.
It’s a step toward becoming the kind of person whose transformation radiates outward—to your children, your partner, your friends, and your colleagues.
When you step into this space, you’re not just choosing transformation for yourself—you’re creating ripples that will touch everyone around you.