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Workday Rising Keynote (September 2025)
Brown's September 2025 keynote at Workday Rising — where she introduced the concept of straddling the paradox of humanity and technology as the defining leadership challenge of the AI era.
Brown's September 2025 keynote at the Workday Rising conference represents one of her most direct public engagements with the AI transition. The keynote introduced the formulation that the future belongs to those who can straddle the paradox of humanity and technology — a framing that maps directly onto You On AI's refusal to resolve the question of whether AI is dangerous or wonderful in favor of the harder question of whether the user is worth amplifying. The talk was delivered to an audience of several thousand business and technology leaders and provided the first systematic statement of how Brown's vulnerability research applied to AI-specific leadership challenges. Its arguments were subsequently elaborated in her October Fortune summit remarks, her Aspen Ideas engagement, and the BetterUp research partnership announced in April 2026.
In The You On AI Field Guide
The keynote's central claim — that paradoxical thinking is huge — framed the emotional challenge of the AI transition as fundamentally a test of ambiguity tolerance rather
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