Reasonably Happy with Paul Ollinger I Read My Essays to You
Jun 3, 2026
He reads favorite Substack essays covering flying with screaming toddlers and when screens are reasonable. He examines public impact versus private choices and the quiet work of not screwing up. Four kinds of schadenfreude and how algorithms exploit them come up. He critiques performative masculinity and reflects on career setbacks and persevering through low-status periods.
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Screaming Toddler Airplane Rule
- Paul Ollinger recounts a Thanksgiving cross-country flight where a toddler screamed for three hours until the father finally used an iPad to calm him.
- The story highlights airline etiquette: on full flights, parents should prioritize peace and use digital sedatives like Elmo from takeoff to landing.
Second Half Success Is Avoiding Big Mistakes
- Success has two halves: early life is about achievement, later life is often about avoiding catastrophic mistakes.
- Paul uses Tom Harden's securities-fraud story to show how early ambition can create more opportunities to self-sabotage later.
Tom Harden's Fall And Rebound
- Paul describes interviewing Tom Harden, a former hedge fund trader convicted for trading on inside information who later rebuilt his life.
- The example emphasizes that high-achieving, 'normal' people can make catastrophic errors and still find a path forward.
