There is a peculiar kind of freedom that comes from being robbed.
Not of wealth, not of possessions, but of illusions.
Kahlil Gibran, in The Madman, tells the story of a man whose masks are stolen. These were not ordinary masks but the many faces he wore for the world—the identities, expectations, and personas he had crafted. At first, he mourns their loss. But then, standing bare before the world, he realizes something profound: he is finally free.
“Blessed are the thieves who stole my masks.”
And then comes an even deeper revelation:
“And I have found both freedom of loneliness and the safety from being understood, for those who understand us enslave something in us.”
To be misunderstood is often painful. In our careers, in our ventures, in our personal journeys, we long to be recognized, to be validated. But there is a hidden cost to being understood too soon, too completely. When people “get” us, they box us in. They define us in ways that might feel comforting at first but quickly become cages. Expectations are set. Labels solidify. The freedom to evolve disappears.
In the early days of a career, of a startup, of a dream—we wear masks. The mask of certainty, of invincibility, of playing the game just right. And then, life does what life does.
We get robbed.
A bad partnership, a deal gone wrong, a business failure, a job loss. Maybe we trusted the wrong people. Maybe we miscalculated. Maybe we simply weren’t ready. It feels unfair. It feels like defeat.
But with time, we realize: the thieves did us a favor. They didn’t steal our essence. They only took the masks.
And without those masks, we are free.
Free to be what we actually are, rather than what we thought we should be. Free to build again, but this time from a place of wisdom, rather than illusion. Free to play the game on our own terms, rather than bending to fit inside someone else’s narrative.
To lose our masks is to lose the safety of being understood. And yet, in that very act, we gain something more precious—the space to redefine ourselves.
Many fear loss. Few recognize its gift.
For those who have been ‘robbed’ early in their journey—of a false sense of security, of blind optimism, of naïve trust—consider this: Maybe it was necessary. Maybe it was the only way to get here, to this place of clarity.
And so, as Kahlil Gibran wrote:
“Blessed are the thieves who stole my masks.”
Because in losing them, we found something better. Ourselves.