Old School with Shilo Brooks George Orwell’s Lessons on the Class Divide
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Nov 20, 2025 
Rob Henderson, bestselling author of *Troubled* and a commentator on social mobility, joins to discuss George Orwell's *Down and Out in Paris and London*. Their discussion reveals how Orwell's experiences with poverty illustrate class divides and misunderstandings between the privileged and the poor. Henderson shares insights from his own life in foster care, contrasting it with elite culture and addressing the subjective nature of poverty. They touch on the challenges of self-sabotage, modern homelessness, and Orwell's sharp humor, making for a fascinating exploration of social class.
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A Teen Finds Orwell In Crisis
- Rob Henderson discovered Down and Out in Paris and London at 15 and read it over several days while in a difficult family situation.
- The book's firsthand portrayal of poverty resonated with his own early struggles and shaped his understanding of class mobility.
Poverty Produces Diverse Responses
- Orwell shows poverty produces varied subjective responses even among similarly situated people.
- Rob notes you cannot reduce poverty to a single behavioral stereotype or ideological narrative.
Boris: Optimism And Self-Sabotage
- Rob recounts Orwell's companion Boris, an optimistic man who repeatedly self-sabotages opportunities.
- He connects this pattern to people he knew who declined help or avoided change out of fear or pride.
