Preparing the Next Generation to Thrive with Ashley Birtwell, Head of School at Sewickley Academy

Success doesn't always follow a straight path, and sometimes the most meaningful opportunities are the ones you never planned for. Greg Weimer sits down with Ashley Birtwell, Head of School at Sewickley Academy, for a conversation about leadership, fulfillment, resilience, and what it takes to prepare the next generation for a rapidly changing world. CHAPTERS 00:50 Welcome to Living Your Legacy 01:18 Meet Dr. Ashley Birtwell 02:39 Too Much Pressure on Kids 03:50 Saying Yes to India 04:30 Middlebury, MIT, and the Psychology of Negotiation 07:10 The Four C's: Commitment, Courage, Capability, Confidence 08:27 The Second Mountain: Achievement vs. Fulfillment 10:27 Teachers Who Love What They Do 12:37 What's Going On with the Next Generation 13:08 AI and the Future of Education 14:53 Doubling Down on Essential Skills 16:56 Phones, Social Media, and Relationships 21:19 Loving What You Do 21:56 Grit Jobs and the Perfect Portfolio 24:09 The Dean Model: Finding the Right-Fit School 27:32 Let Them Struggle 30:12 Am I Really Fulfilled? 34:03 Advice for Parents, Coaches, and Mentors 35:07 Relationships Are the Greatest Value 36:08 Leading with Empathy 37:19 Closing GUEST Ashley Birtwell — Head of School, Sewickley Academy HOST Greg Weimer — Founder and CEO, Confluence Financial Partners TOPICS Community & Impact