Harley Finkelstein: Why You Must Requalify for Your Role—Every Year [The Knowledge Project Ep. #236]

Shane Parrish: Welcome to the Knowledge Project. I’m your host, Shane Parrish. In a world where knowledge is power, this podcast is your toolkit for mastering the best of what other people have already figured out. Today my guest is entrepreneur and Shopify president Harley Finkelstein. In this raw conversation, we dive into Harley’s unreasonably high standards, his courage to close doors and fully commit to a path, and the radical idea of requalifying for your job every single year. We explore how Shopify is leveraging AI, why stepping down as the COO to become president was the most gut-wrenching decision of his life, his near-militant calendar management system, and the delicate dance between fierce ambition and genuine gratitude. Three moments in particular hit me hard: when Harley vulnerably shares about his relationship with his father, it made me think of my own troubled past with my biological father; the family motto he’s created that’s so powerful I’ve already adopted it at home with my kids; and the revelation that beneath his reputation as a world-class storyteller lie countless unseen hours, practicing in the dark, perfecting a craft that most people assumed came naturally. It’s time to listen and learn.  

Shane Parrish: I want to start by asking, What areas of your life do you think you have what other people would consider unreasonably high standards?