There are seasons in leadership when the problems we face feel ancient, tangled, and deep—too vast to grasp in a single meeting or manage with another spreadsheet. They rise not from a single moment, but from layered dynamics, patterns of dysfunction, spiritual fog, or cultural undercurrents that stretch beyond logic. These moments are what we’ve come to call “wrestling with Leviathan.”
Leviathan is a term pulled from Scripture and ancient imagery—a sea creature of chaos and mystery. In leadership, it’s not just poetic—it’s painfully accurate. Leviathan moments aren’t ordinary conflicts. They’re systems that protect the wrong people. Situations that keep slithering out of reach. It’s when you try to bring order, but everything stays just a little twisted.
And yet—leaders are called to wrestle. Not to destroy, not to dominate, but to discern, to name the truth, to stand steady, and to act when others freeze.
What Does That Look Like?
Let’s get concrete.
There’s an employee on the team—strategic, polished, and consistently a problem. They manipulate policies, play favorites, deflect blame, and somehow always land on their feet. HR has tried. Coaching has been attempted. Conversations have happened. And still—nothing changes.
In fact, the person is getting better at the game. They’ve learned the loopholes. They know how to charm upper leadership, create confusion, and discredit the complaints that rise up. Sometimes people already know what’s happening. Other times, the damage creeps in slowly, as morale erodes and trust quietly disappears.
Meanwhile, the team is watching. They see what’s happening. They quietly wonder why no one is doing anything about it. Why leadership won’t step in. Why the rules apply unevenly.
And burnout begins to set in—not just because the work is hard, but because the people who care feel powerless. That’s Leviathan. Not just a person—but a pattern. A spiritual and organizational entanglement.
To the Skeptic:
You may hear all this and dismiss it.
“Isn’t that a little dramatic? Sounds like folklore. Myth. Superstition.”
I understand the hesitation. But I challenge you to look again.
Some dynamics are darker than you think. They operate like spiritual undertow—pulling, twisting, choking systems from within. When confusion and accusation take root, when truth gets slippery and courage feels dangerous—don’t dismiss it as coincidence. That’s Leviathan squeezing. Adding pressure. Stirring chaos just beneath the surface.
And here’s the trap:
Leviathan rewrites the narrative.
It recasts the perpetrator as the victim. It seduces leadership with a false compassion that obscures responsibility. It makes decisive leaders second-guess themselves—and truth-tellers look like bullies.
It’s subtle. It’s dangerous. And it works—until someone names it.
Three Things to Do When You Face Leviathan:
1. Don’t Go Alone
Leviathan thrives in isolation. You need others—prayer partners, elders, wise counselors. Bring trusted people into the situation and walk in community.
“Two are better than one… If either of them falls down, one can help the other up.”
—Ecclesiastes 4:9–10
“Plans fail for lack of counsel, but with many advisers they succeed.”
—Proverbs 15:22
2. Don’t Befriend It
Leviathan doesn’t play fair. It may charm you. It may offer comfort or convenience. Don’t excuse toxic behavior for the sake of peace—it’s false peace. Stand in truth.
“Can you pull in Leviathan with a fishhook or tie down its tongue with a rope?… Any hope of subduing it is false; the mere sight of it is overpowering.”
—Job 41:1, 9
“Woe to those who call evil good and good evil…”
—Isaiah 5:20
3. Ask God for Help and Wisdom
This is spiritual territory. You won’t win with strategy alone. Ask the Holy Spirit to reveal what’s hidden, to embolden your steps, and to bring truth into the light.
“If any of you lacks wisdom, you should ask God… and it will be given to you.”
—James 1:5
“The LORD will fight for you; you need only to be still.”
—Exodus 14:14
“In that day, the LORD will punish with His sword… Leviathan the gliding serpent… He will slay the monster of the sea.”
—Isaiah 27:1
Biblical Mentions of Leviathan:
“You crushed the heads of Leviathan and gave it as food to the creatures of the desert.”
“There the ships go to and fro, and Leviathan, which you formed to frolic there.”
You’re Not Alone in the Wrestling.
Leadership in these moments isn’t about maintaining control—it’s about staying aligned with truth, even as the waves hit. These are the moments when faith, discernment, and courage matter most.
To every pastor, director, manager, team leader, elder, or board member feeling squeezed—you are not alone. Others are wrestling too. And you’re not crazy to feel the weight.
Leviathan is real. But so is the power of God to expose it.
God hovers over the chaos still. And He calls leaders to rise.
More to come.
