S2 E2: The Courage to Be a Beginner

The more successful you become, the harder it is to be bad at something again. So what happens when reinvention asks you to start from zero? Joy Chik and Boaz Ashkenazy explore why accomplished people resist becoming beginners, why learning in public can feel so exposing, and why confidence rarely comes before action. Boaz is an Executive AI Advisor at Redapt and the founder and host of Shift AI. From a teenage bet that got him onto the basketball court, to launching a podcast with no experience, to raising his first round of startup funding, Boaz has repeatedly put himself in situations where he didn't yet know what he was doing. Together, Joy and Boaz unpack what those experiences taught him about starting before you're ready, learning through imperfect repetition, and finding the courage to keep going before confidence shows up. For newsletter updates, sign up here. For video episodes, visit our podcast on Apple, YouTube, or Spotify. Follow us on LinkedIn, Instagram, and Facebook. Send your feedback and suggestions for future episodes to [email protected] Logo and other art courtesy of Andy Reddout. This podcast was produced by Tom Larson and Sue Corcoran, and edited by Amy Enser.