The Healing Time

Finding the Holy in the Mess

I’ve been part of Substack for a few years now, but I quickly fell away from it as it wasn’t offering me the quick fix other social media platforms did. Thankfully, I’ve done some growing (and healing) since then, and now I’m back, so I thought I would introduce myself.

I’m Caleb, and if you’re here, it means something about my journey, my words, or maybe just my gloriously imperfect humanness has resonated with yours.

I’m honored you’re here. Truly.

You might know bits of my story—West Point, the NFL, janitorial work in exchange for therapy (yep, that’s real), and now, somehow, a book deal. It’s called Naked Ambition. No, it’s not that kind of ambition, but it does get into how I spent years chasing a version of success I thought would save me, only to realize that the real journey wasn’t up—it was down.

Recently, I turned 40.

My son Rune, now four months old, doesn’t seem too impressed, and my toddler daughter is keeping me on my toes. Her negotiation skills rival the best attorneys, and I’m constantly straddling the line between being in awe of her tactics and remembering, I’m still the parent here...right?

Meanwhile, I often joke that I missed my wife when we had one kid. Now with two, it sometimes feels like we’re living in entirely different countries. But every now and then, amidst the chaos, we’ll exchange a knowing glance that says, We’re doing this. Somehow, we’re doing this. And that keeps me grounded.

Lately, I’ve been reflecting on a different kind of journey—one less about the upward climb and more about the downward descent. What Richard Rohr might call “the further journey.” It’s no longer about building, achieving, or adding, but about letting go, digging deeper, and embracing the wisdom of the fall.

There’s a poem that’s been echoing in my mind during this season. It feels like it’s speaking directly to the work I’m doing within myself:

Finally on my way to yes
I bump into
all the places
where I said no
to my life
all the untended wounds
the red and purple scars
those hieroglyphs of pain
carved into my skin, my bones,
those coded messages
that send me down
the wrong street
again and again
where I find them
the old wounds
the old misdirections
and I lift them
one by one
close to my heart
and I say holy
Holy.
– Pesha Joyce Gertler

For so long, I’ve tried to figure out life’s unanswered questions in my head—analyzing, planning, controlling—and it’s brought more pain and suffering than clarity. But these days, I’m learning to hold the tension of the question itself.

To dance with the mystery, treasure the vulnerability, and trust the unfolding.

This space—this newsletter—is where I’ll share what I’m learning along the way. Sometimes it’ll be light and funny (because parenting toddlers is basically a masterclass in humility). Other times, it’ll be contemplative, leaning into the poetic, soulful spaces that have carried me through.

Always, it will be real.

So, here’s to the courage it takes to let go. To exhaling. To saying yes to the descent.

Out beyond ideas of wrongdoing and rightdoing, there is a field.
I’ll meet you there.
– Rumi

As always, I’m rooting for you. We’re in this together.