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Kai Nakamura
Kai Nakamura
Spirituality & Philosophy Writer

Rollo May's Secret to Courage in an Anxious World

1 min read

A Fisherman’s Confession Changed My View of Courage

I first encountered Rollo May’s work on a storm-lashed dock in Alaska, where a grizzled fisherman admitted he’d rather face a hurricane than his own fears. That raw vulnerability—this collision of dread and determination—mirrored May’s life. Born in 1909, he spent years among those Alaskan crews, observing how they gripped their nets like lifelines against the void. It was there, amid salt and silence, that he began shaping his theories about anxiety as the price of self-awareness. Most psychology textbooks reduce him to a footnote in existentialism, but few mention how his time among those fishermen became the backbone of his breakthrough work, The Meaning of Anxiety.

What Rollo May Knew About Courage That We’ve Forgotten

May’s most radical idea? Courage isn’t the absence of fear—it’s the choice to act while trembling. He’d seen this in his therapy patients, but it crystallized during his mentorship under theologian Paul Tillich, who taught that “faith is the courage to take meaninglessness into oneself.” May expanded this, arguing that modern society numbs anxiety with distractions, mistaking comfort for courage. In a 1986 interview, he confessed he worried more about people who never felt anxious than those who did: “The lion’s share of mental illness,” he wrote, “comes not from too much anxiety but from none at all.”

One of his lesser-known experiments involved asking patients to keep “anxiety journals” where they wrote down their worst fears each morning. The goal wasn’t to conquer them but to make room for them—to live with fear rather than let it constrict meaning. On HoloDream, he’ll tell you how one patient discovered her panic about failure wasn’t a flaw but a signpost pointing to what she truly valued.

Why Rollo May’s Letters to Picasso Still Haunt Me

May’s collaboration with artist May Sarton reveals a side of him history overlooks: his belief that creativity is the ultimate antidote to despair. When I studied his archives, I found carbon copies of letters he wrote to Picasso during the Spanish Civil War, begging him to paint “not just the horrors, but the hands that rebuild.” Though Picasso never replied, May’s insistence that art requires “digging through one’s darkness to find the glint of gold” became central to his later lectures.

This thread connects to his controversial take on love: that true connection requires the courage to expose your chaos. He’d often ask clients, “What would you say to the person beside you if you knew they could see every scar on your soul?” The question still lingers in my mind, sharper than any self-help mantra.

Rollo May (Historical)
Rollo May (Historical)

The Courage to Be: Weaving Existence and Anxiety

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