Ryan Holiday: Why You Need to Reparent Your 14-Year-Old Self & How to Overcome the Fear of Not Being Good Enough

What would you tell your 14-year-old self?

How do you quiet the “not good enough” voice?

Today, Jay welcomes Ryan Holiday, renowned philosopher, bestselling author, and host of The Daily Stoic. With over 10 million copies of his books sold globally, Ryan returns to the podcast to dive deep into the concepts of personal growth, parenting, and finding purpose in a success-driven world.

Ryan reflects on the journey of becoming a parent and discusses the difference between having kids and truly being a parent. He explains why intentional parenting is a radical shift from simply fulfilling biological or legal roles and explores the transformative impact of parenthood on personal and professional ambitions, emphasizing the importance of being prepared for the changes it brings.

Jay also opens up about his own thoughts on parenthood and the life shifts that accompany major decisions, offering a heartfelt glimpse into the conversations he’s had with his wife about the timing of having children. Throughout the conversation, both Jay and Ryan unpack the struggles of balancing a career with personal life, with Ryan drawing from Stoic philosophy to offer guidance on setting meaningful goals, aligning actions with values, and learning from life's obstacles.

In this interview, you'll learn:

How to Embrace Parenthood as a Central Life Purpose

How to Set Goals Based on What’s in Your Control

How to Approach Parenting with Intention and Purpose

How to Learn from Life’s Obstacles and Failures

How to Align Your Career with Personal Values

How to Build Emotional Resilience through Parenthood

Whether through parenting, personal growth, or our professional pursuits, the key is to stay rooted in what truly matters—our values, intentions, and the legacy we leave behind.

With Love and Gratitude,

Jay Shetty

What We Discuss:

00:00 Intro

01:33 Are You Ready to Become a Parent?

05:43 What Type of Goal Should We Set?

10:54 Love What You’re Doing

18:59 Stuck in Life

22:06 Trust the Process

26:04 Patience

30:18 Process of Accumulating Experiences

33:35 What Difference Are You Making?