Rollo May — On AI
This page lists every Orange Pill Wiki entry hyperlinked from Rollo May — On AI. 11 entries total. Each is a deeper-dive on a person, concept, work, event, or technology that the book treats as a stepping stone for thinking through the AI revolution. Click any card to open the entry; in each entry, words colored in orange link to other Orange Pill Wiki entries, while orange-underlined words with the Wikipedia mark link to Wikipedia.
Creative Courage
The willingness to bring something new into being despite uncertainty—May's defining human capacity that AI cannot supply.
Friction
The resistance AI tools eliminate from knowledge work — a category whose composition (wolf or parasite?) determines whether its elimination is liberation or erosion.
Intensity Without Depth
High-output activity lacking genuine encounter—May's diagnosis of achievement culture, now amplified by AI to its breaking point.
Ontological Anxiety
The irreducible discomfort of freedom—May's reframing of anxiety as the signal that genuine creative territory has been entered.
The Anxiety Check
May's diagnostic question for AI collaboration: Am I experiencing the discomfort of not knowing whether the direction is right?
The Daimonic Force
The simultaneously creative and destructive drive demanding expression—May's term for the irrational energy requiring integration, not elimination.
The Encounter (May)
The collision between intensively conscious human being and reality exceeding current understanding—the creative moment requiring courage, not talent.
The Growth Question (May)
May's third diagnostic: Am I more capable of genuine encounter today than six months ago?—measuring capacity, not output.
The Intentionality Test (May)
May's second diagnostic: Can I articulate what this work is for—not what it produces, but what it serves?
The Too-Competent Therapist
May's warning that resolving the patient's uncertainty too quickly steals the encounter—now AI's characteristic failure mode.
