The Man in the Hole: A Leader’s Guide to Reading the Arc

My friend Sarah, VP at a Fortune 500 company, sat across from me last week and said, “Chris, I don’t recognize myself anymore. I’m winning at work and losing everywhere else.” She paused. “And I’m not even sure when this started.”

I knew exactly what had happened to her. Someone achieves everything they thought they wanted, and it feels like nothing. The empty feeling at 2 AM doesn’t go away.

She needed permission to understand what was actually happening. So I told her a story.

In 1947, a man named Andy was walking around the world just like you and me. Living a pretty good life. Then he got thrown in jail for something he didn’t do.

Prison was tough. He maintained his innocence. Thrown in solitary confinement. But eventually, he started doing the right things. Meeting the right people. After 19 years, he escaped through a 400-foot tunnel he’d dug behind a Rita Hayworth poster, ran through the rain and moved to Mexico to open a resort with his best friend from prison, Morgan Freeman.

If you’re just now realizing that’s the plot of The Shawshank Redemption, welcome. It’s the number one rated movie of all time on IMDb. And it’s the most important leadership story you’re not using.

In that same year, 1947, Kurt Vonnegut submitted his master’s thesis at the University of Chicago. His radical idea: all stories have shapes that can be drawn on graph paper. The boy meets girl. The rags to riches. The Cinderella arc. They all have geometry.

The university rejected it. Too simple.

The shape Vonnegut found to be the most enduring of all was the Man in the Hole. A person of decent fortune, living a comfortable life, falls into a hole. They learn some things. They meet some people. Their old skin cracks.

Where they stop performing and start becoming. It’s suffocating and necessary, and most people will do anything to get out before they understand they’re supposed to be in there. And the new normal they arrive at is better than where they began.

Andy Dufresne, in the movie, lived it. And here’s what I’ve learned after hosting more than 800 dinners on six continents, sitting across from executives, artists, veterans and strangers alike: Every single one of us is living it too.

The question is, where are you right now? Are you up top, in the comfort zone, not yet aware that growth requires descent? Are you in the fall, triggered by a job loss, a diagnosis, a betrayal, feeling the ground give way? Are you down in the hole, sitting in silence, in grief, in that suffocating uncertainty where you’re not sure if tomorrow exists? Are you in the climb, starting to realize that tomorrow can be better than yesterday, as long as you don’t try to get there alone? Or have you arrived at the new normal, having stared your demons in the face and discovered that feeling known, held and whole is not weakness, it’s the whole point?

Wherever you are, the arc doesn’t end. It restarts.

Crazy thing, the skill that separates good leaders from transformative ones has nothing to do with telling a great story. It has everything to do with reading one.

Leaders who change cultures, who retain talent, who build loyalty, they can look at another human being and diagnose where that person is in their arc. And then meet them there.

This is the work. And it comes down to three practices.

Locate Yourself First

You cannot read someone else’s arc if you haven’t taken an honest inventory of your own. This is the part most leaders skip. We’re trained to assess others, to manage performance, to coach and direct. But the Man in the Hole demands something more uncomfortable: it asks you to admit which part of the arc you’re living through right now. When you admit to your team that you’re scared, that you’re in the climb, that you don’t have all the answers, you give up the armor of certainty. You become human.

Diagnose Before You Prescribe

How you support someone who is falling into a hole is fundamentally different from how you support someone who is ready to climb out. The person in the fall needs to be seen. They need you to mirror what they’re experiencing, not fix it, not reframe it. They need you to say, “I see this is happening to you,” and mean it. You have to slow down. You have to listen more than you talk. You have to sit with discomfort instead of rushing to resolution. In a world obsessed with velocity, this feels like productivity loss. But it’s not. It’s the most productive thing you can do. Because you only get one chance to meet someone in their hole. Miss it, and they climb out alone. And when people climb out alone, they climb out away from you.

Honor the Hole

This is the hardest one. The hole is not a problem to be solved. The hole is where the transformation happens. It’s where resilience is forged, where old identities break down so new ones can emerge, where people discover what they’re actually made of. You have to believe that the darkness serves a purpose. You have to resist the temptation to save people before they’re ready to be saved.

Every person in your organization is somewhere on this arc right now. The ones who are in the hole are often your best people. They’re the ones brave enough to admit something broke. They’re the ones willing to sit in the dark long enough to actually change.

Don’t let them leave while they’re still down there. Don’t try to fast-track them out with false optimism. Don’t misread their darkness as weakness.

That’s when they need you most.

So I’ll ask you what I ask everyone: Where are you right now?

And who in your organization is in the hole, waiting for a leader brave enough to honor it?