Thinking Sideways

Jennifer Shahade's Thinking Sideways draws on her experiences as a chess and poker player to teach practical decision-making techniques.

The book emphasizes avoiding binary choices by finding third options, thinking in short chunks, and testing ideas by trying to falsify them.

Shahade weaves personal stories, research, and examples (from chess, poker, and AI) to show how focus, resilience after mistakes, and ambition grounded in values lead to better outcomes.

It also discusses how AI changes learning and work, how to reinvent a career in chunks, and the ethics around cheating and ambition.

Overall, the book provides actionable frameworks for clearer thinking under uncertainty and distraction.