Start Over Without Regret — Modern Wisdom (Chris Williamson & Bill Gurley)

If you hate your job, the worst thing you can do is nothing—this episode shows how to start small and test a real pivot. (Original ~90 minutes → Condensed ~15 minutes.) Chris Williamson and investor Bill Gurley unpack why seven in ten people regret their career choices, Jeff Bezos’s regret-minimization framework, and practical moves—dream folders, side projects, peer groups, and mentor strategies—to convert longing into action. Learn how to evaluate options with battle cards, protect financial flexibility, avoid harmful VC traps, and use AI as a productivity jetpack rather than a threat. Topics include career change, startups, leadership, lifelong learning, AI, and decision-making. Listen now to get the key ideas and concrete steps in minutes.