This week, I talk with Patrick McKenzie, better known online as “patio11.” Patrick has built an impressive career by sharing his insights publicly, with more than three million words published to date. From his years at Stripe to his current sabbatical, Patrick’s journey proves that the “traditional path” is not always the best one. We explore how his love for systems thinking and complex problem-solving has shaped his career. He shares candidly about his 20 years in Japan, navigating work-life balance, his evolving thoughts on autonomy, and how writing has opened doors to unexpected opportunities. Known for his deep dives into topics you didn’t realize you cared about, Patrick brings fresh perspectives on tech, culture, and finding meaning in work. Let’s get to it! In this episode: (00:00) - Intro (03:10) - Why gaming is underrated for learning real-world skills (06:21) - Why do thieves steal soap? (08:54) - Following intellectual curiosity (13:18) - Call centers and organizational systems (22:39) - Lessons from 20 years in Japan (28:30) - The salaryman (37:08) - Patrick's transition to entrepreneurial ventures (39:09) - How to know what to keep and what to change (42:14) - Dealing with career uncertainty (52:08) - Professionals vs amateurs (57:14) - Lessons from Stockfighter (01:01:07) - Stripe and stepping into the void (01:21:50) - The impact of writing and sharing knowledge (01:26:30) - The relationship between community and impact Get full show notes and links at https://GoodWorkShow.com. Watch the episode on YouTube: https://www.youtube.com/@barrettabrooks.