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The Gray Area with Sean Illing

The Gray Area with Sean Illing

The millennial midlife crisis

Sep 11, 2026 · 50m

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About this episode

Is "adulthood" a moving target? For millennials, hitting the milestones of the past — homeownership, secure careers, and financial independence — feels tougher than ever. We aren't just having our individual midlife crises; we are simultaneously navigating economic, cultural, and existential crises too. Guest host Jonquilyn Hill sits down with Amil Niazi, columnist at The Cut, to explore why this stage of life feels so precarious. From the domino effect of the 2008 financial crisis and the collapse of the traditional career path, to the pressures of the "sandwich generation" — caretaking for both children and aging parents — we break down why the millennial experience is fundamentally…