The Mask, the Wound, and the Work

“There is a razor-thin line between trying to find something usefully redemptive in illness and lying to ourselves about the nature of suffering.”

Meghan O’Rourke – The Invisible Kingdom

There’s a moment from my recent conversation with Oliver Ravn that has stayed with me—one of those sentences that lands with the weight of a life’s truth behind it.

He said, quietly and without drama: “I created versions of me that were not me.”

He didn’t say this with self-judgment. He said it as a man who had finally come to understand the psychic cost of surviving his childhood. Because when you grow up with chronic illness—psoriasis on your face, scalp, arms, the places you can’t hide; Crohn’s disease in your gut; the endless cycle of doctor visits, misdiagnoses, and dismissal—you learn early how to adapt. You learn how to become what the world needs you to be.

Or what you think it needs you to be.

When Oliver was fifteen, kids called him a monster. Not metaphorically—literally. And as he told me, “If you’re called a monster enough times, you start to believe it.” The stigma sank deep. Loneliness took root. The shame hardened into the mask he wore for the next sixteen years.

Listening to him speak, I felt the echo of so many people I’ve worked with—the ones who excel because, somewhere deep inside, they’re still trying to protect the frightened child they once were.

The False Self That Keeps Us Safe

Psychoanalysts will sometimes call this adaptation the false self—the self we build to keep the world from touching the tender places.

For Oliver, the false self looked like:

• Long sleeves even in summer.
• Eating only foods that wouldn’t trigger his gut—often pretending he “wasn’t hungry.”
• Wearing only clothes that wouldn’t show the flakes from his scalp.
• Pretending he wasn’t in pain or afraid—pretending he was just like everyone else.

In other words, masking.

For years, he hid the very experiences that shaped him. So well, in fact, that when he traveled through Thailand with his closest friend—the person who knew everything about him—they each hid the same secret from the other. Only later did they discover they both had psoriasis.

Both ashamed. Both hiding. Both alone together.

That moment, he told me, became the seed of Chronicare, his life’s work.

Standing in the Water

When Oliver reached out after reading Reboot, my first book, and something his investors recommended he read, he apologized for the emotion in his message. He was worried it might be too much. It wasn’t. It never is.

He described standing in the water off Majorca, book in hand, crying as he asked what he called “all the questions.” And then he said something I haven’t been able to forget: “For the first time, I told myself I am good enough the way I am.”

That is the moment of unmasking.

In every real transformation, there comes a point when the false self cracks—when the old survival strategies simply can’t contain the truth we’ve been refusing to say out loud.

That truth, in Oliver’s case, was simple and seismic: “I don’t need the mask anymore,” he thought to himself. “I don’t need to pretend.” And then, finally: “I am enough.”

It reminded me of something Suleika Jaouad wrote in Between Two Kingdoms: “Grief isn’t meant to be silenced, to live in the body and be carried alone.” And I thought: this is what it means to be human with one another. This is the community Oliver has created. This is what it means to speak with a whole heart. This is what it means to be listened to, to be accepted wholly.

The Wound Becomes the Work

But here’s where the story shifts from the personal to the generative. Because the wound didn’t just open him—it pointed him toward his work.

That moment in Thailand with his friend, the years of secrecy and shame, the loneliness that comes from not being believed by the medical system—these became the foundation of Chronicare.

Chronicare is, quite literally, the community he needed at fifteen but never had:

• A place to talk without stigma.
• A place to meet others who understand.
• A place where the care continues after you leave the clinic.
• A place where your story is not an anomaly, but a belonging.

He has built a community of people with Crohn’s disease and ulcerative colitis. A thousand users so far. A thousand people saying, “Thank you. I finally feel heard.”

This right here is the work I call redemption. In this case, redemptive leadership is the process of using our labor, our leadership, and our service to redeem the very parts of ourselves that shame once forced into hiding—the parts we masked away to survive.

Of course, as every founder knows, once the wound becomes the work, the work threatens to become the self. So, at one point, Oliver admitted: “If Chronicare fails… I don’t know who I am.”

I felt the weight of that. I’ve carried that same thought. I’ve coached countless people through it. And I gently said to him what I’ll say to you: We have to distinguish between the form and the function of our work.

The form—the container—is your company, your role, your title, your strategy deck. And it will change. It must. Everything is impermanent. Everything evolves.

But the function—the content that resides in the container? The deeper calling? The lifelong impulse to be a responder to suffering? That’s yours forever.

After I told him this, he paused. Then he gave me a line that belongs to him—but echoes inside me still: “It drives me, but it’s not who I am.”

The Mask, the Wound, and the Work

What Oliver revealed to me is what I’ve come to believe after decades of coaching.

We lead best from the places we once feared most.

Not because suffering is ennobling in itself. But because when we stop hiding, stop masking, stop performing, our lives become rooted in something sturdier than accomplishment. Our leadership becomes an offering, not a performance. Our companies become containers for connection, not compensation for self-doubt. And our work becomes a gift to the next generation.

Toward the end of our conversation, I said to him, “You are speaking to the next 15-year-old kid who has just been diagnosed. He will hear you. And he will know he is not alone.”

Oliver nodded. And in that moment, I felt the fabric of lineage—teacher to student, elder to emerging adult, wounded healer to wounded healer—woven between us.

A Benediction

If you’ve read this far, perhaps something in Oliver’s story speaks to you. Perhaps you, too, have built masks to protect the places that hurt.

Here’s my wish for you…

May you remove one small mask.
May you honor one old wound.
May you allow your work and not your persona to speak for you.
And may the person beneath the mask know they are, and always have been, enough.