Wrestling with Angels: When the Big Questions Find You

There’s a moment in the Hebrew Bible that has always struck me with its raw power and mysterious beauty. It’s the story of Jacob, alone at night, who ends up wrestling with an angel until daybreak. He refuses to let go until he receives a blessing. The angel finally relents—but not before dislocating Jacob’s hip. Jacob limps for the rest of his life, a permanent mark of a divine encounter. And yet, he walks away changed, renamed, and blessed. He becomes Israel: “one who wrestles with God.”

I return to this story often, especially in my work with clients and in my own life. It is not just an ancient tale—it’s a timeless reflection of what it means to be human. Because all of us, at one point or another, will find ourselves in our own version of this midnight wrestling match. And just like Jacob, we don’t emerge from these encounters unchanged.

The Nature of Wrestling

Jacob didn’t win by overpowering the angel. He won by not giving up. He clung to what he knew was possible, even if it defied logic. I mean, really—who wins a wrestling match with an angel? And yet, that’s the point. The odds didn’t matter. The outcome didn’t come from a place of dominance, but from relentless seeking. From spiritual grit.

There’s something about that kind of fierce, unrelenting presence that feels incredibly relevant right now. So many of us are in the middle of our own soul-struggles, standing barefoot on the holy ground of Big Questions.

What does it mean to be good—or bad?

What beliefs do I still hold about the Divine? And which ones no longer fit?

Why is there so much suffering? And what is my role in easing it?

What is the path to personal power that doesn’t rely on force, but on truth?

What kind of community do I belong to? And what kind of community do I long to build?

These aren’t polite coffee-table questions. These are questions that grab us by the collar in the middle of the night. They demand something of us—our time, our attention, our courage.

I call this experience “wrestling with an angel.”

It’s Not a Breakdown, It’s a Breakthrough

When people bring these questions to therapy or spiritual direction, they’re often scared. It can feel like something is falling apart. And in a way, it is. But not in the way they fear. What’s falling apart is the version of themselves that can no longer hold all the truth that is pressing to be known.

Wrestling with an angel is not a failure. It is a holy initiation.

And just like Jacob, you may walk away with a limp. A tenderness. A mark. But you will also walk away blessed. Transformed. Re-named.

You don’t walk away as the same person who entered the struggle. You emerge as someone who has encountered the Mystery and dared to stay in the ring.

The Cost—and the Blessing

Let’s not romanticize the experience. Jacob’s blessing came at a cost. He carried his injury for the rest of his life. The limp didn’t make him weak; it made him real. It reminded him, with every step, that he had met something greater than himself and survived. That he had chosen engagement over escape. That he had refused to let go before something holy had been exchanged.

There is always a cost to spiritual growth. An old belief, an old identity, an old comfort must be surrendered. But in exchange, we receive something far more valuable: a blessing. A deeper truth. A more authentic path. A faith that is no longer borrowed, but earned through encounter. Experience is where we come to know the Divine- not information, inherited beliefs, or religious teachings. It is the encounter with the Divine that shows us who She is to us and who we are to Him.

Wrestling Is a Sign of Life

If you’re in a spiritual or emotional wrestling match right now, take heart. This is not evidence that you’ve failed or lost your way. It’s a sign that something in you refuses to settle for shallow answers. It’s a sign of life. Of presence. Of longing. And longing, especially the kind that won’t let go until it touches something real, is sacred.

This kind of wrestling is not a solo sport, either. It helps to have a companion—someone who can hold space for your questions without rushing to fix or spiritualize them. Someone who can sit in the not-knowing with you, breathing alongside you as you wait for the dawn.

Action Steps for the Wrestlers

If you find yourself wrestling with an angel—metaphorically speaking—here are some grounded steps you can take to honor your process:

1. Name the Question

Give words to what you’re struggling with. Write it down. Say it out loud. Share it with someone you trust. Naming the question doesn’t solve it, but it does anchor it. And often, our wrestling begins to soften when we stop hiding from the real inquiry.

2. Create Time to Be With It

Wrestling doesn’t happen in the rush of your to-do list. Create sacred time to sit with your question. Light a candle. Go for a walk. Let yourself cry. Let yourself rage. Let yourself be silent. The clarity won’t always come immediately, but your presence creates a container for truth to rise

3. Drop the Demand for Immediate Resolution

This kind of spiritual struggle unfolds in spirals, not straight lines. The goal isn’t always to find an answer right away—it’s to let yourself be shaped by the asking. Trust that the blessing will come in its own way, on its own terms.

4. Watch for the Limp

There may be a cost to what you’re going through. It may change how you move in the world. You might lose relationships that were only held together by surface agreement. You might become more tender, more cautious, more reverent. These changes are not wounds—they are wisdom.

5. Stay Open to the Blessing

Sometimes the blessing isn’t what we expected. It may come as a new understanding, a deeper sense of peace, or even a renewed sense of calling. Stay open. The angel may leave you marked, but it will not leave you empty-handed.

6. Find Your Wrestling Tribe

Surround yourself with others who are also asking hard questions. Find or build a community that honors honesty, mystery, and depth. You don’t need a crowd—just a few kindred spirits who can say, “Me too,” and mean it.

We are in a collective season of wrestling. The old answers no longer satisfy. The shiny spiritual bypasses are wearing thin. And what’s left is the real work: showing up, night after night, refusing to let go of the questions that matter most.

If that’s where you are, I see you. I honor you. And I believe with all my heart that something sacred is being born in the struggle.

Just don’t let go before the blessing comes.