📮 The Art of Falling Apart
Letters from a Seeker (Vol. 61)
📮 Letters from a Seeker
“Letters from a Seeker” is a weekly series of short contemplations that explore the mystery, meaning, and art of living. The word ‘Seeker’ in the title is inspired by the Delphic maxim: “Be a seeker of wisdom.” *** This series is exclusive to members.
Dear Fellow Traveler,
The self-help industry has a complicated relationship with difficulty.
It will happily sell you tools for managing difficulty, frameworks for reframing it, morning routines for preventing it, and, if things get really bad, a guided meditation for accepting it.
What it is notably less enthusiastic about is the idea that difficulty might not be something to solve. Instead, some challenges in life are not barriers to flourishing but rather the very means through which flourishing becomes possible. This is an old idea.
It is also, in the current climate, a quietly radical one.
St. John of the Cross (1542–1591), the Spanish mystic, poet, and sometimes prisoner of his own religious order, addressed the subject with remarkable clarity and honesty.
He called it the dark night of the soul.
A phrase that has since been borrowed so promiscuously by the culture—applied to bad weeks, difficult relationships, career pivots, and general existential Tuesdays—that it has nearly lost its original meaning.
That is a shame, because the original meaning is considerably more useful than the diluted version.
For St. John of the Cross, the dark night was not a metaphor for feeling bad. It was a precise description of a specific interior experience—the experience of having the things you relied on for meaning, comfort, and a sense of self go quiet. Not disappear dramatically. Just go quiet.
The practices that once sustained you begin to feel empty.
The frameworks that once organized your life begin to feel thin.
And you are left in an interior darkness that, St. John insisted, is not a sign that something has gone wrong. It is a sign that something is going right.
The consolations had to fall quiet because you were leaning on them too heavily—mistaking the costume for the person wearing it, the comfort for the thing that truly sustains. The dark night strips away false supports, not to leave you with nothing, but to reveal what was always there beneath.
Something sturdier. Quieter. And less dependent on everything going well.
Thomas Merton (1915–1968)—the American Trappist monk who became one of the 20th century’s most widely read spiritual writers, largely by being more honest about doubt than most spiritual writers are permitted to be—spent years living inside the tradition St. John of the Cross described. And he added something John couldn’t quite have anticipated: a diagnosis of why the modern version of this experience is so particularly disorienting.
The problem, Merton thought, is that we arrive at the dark night carrying an extra burden. We arrive carrying the false self.
