Jay Shetty & Ryan Holiday ON Why You Need to Reparent Your 14-Year-Old Self

What if the key to becoming a better parent was hidden in the unresolved issues of your childhood?

 Imagine if every experience in your life—both good and bad—was material for personal growth, shaping not only who you are today but also the parent you're becoming.

In this On Purpose episode, Jay Shetty welcomes Ryan Holiday, renowned author, speaker, and modern-day philosopher. Holiday, known for his groundbreaking works like The Obstacle is the Way, Ego is the Enemy, and Stillness is the Key, returned to discuss his latest book, The Daily Dad: 365 Meditations on Parenting, Love, and Raising Great Kids.

Parenthood Comes with Responsibility

Ryan Holiday stressed to Jay Shetty the critical importance of accepting the responsibility that comes with parenthood. He believes that having children and being a committed parent are two very distinct things. In his view, anyone can have children, either through biological or legal means. However, deciding to become a parent is a much deeper and involved process; it requires intentional effort and sacrifice.

Holiday explains to Jay Shetty that parenting isn't just about doing the bare minimum to ensure the child's survival; it's about changing your life to accommodate and prioritize your child's emotional, psychological, and developmental needs. It is crucial to set your intention and be actively involved in their life. Being a parent means also becoming a source of guidance, safety, and emotional support for your child.

Similarly, Jay Shetty believes that becoming a parent involves a shift in perspective - your priorities need to align with the demands of raising a child. Jay and Ryan Holiday agree that parenthood needs to become the central role in your life, never secondary or passive. It involves a deep personal commitment that redefines your sense of purpose as a parent.

Parenting Is a Process

Parenthood is a lifelong journey, Holiday told Jay Shetty. It's a process of continuous learning. He explains that no matter how much you prepare for it, nothing can truly prepare you for it. Becoming a father has transformed Holiday in unexpected ways. He even attributes a large proportion of his self-development to parenthood. The author also shares that parenting evolves and challenges you to grow beyond your preconceived notions of what it takes to be a parent.

Ryan Holiday explained to Jay Shetty that many people have pre-conceptions about how they will raise their children. However, more often than not, these change as the journey unfolds; unexpected real-life situations arise, which may alter your initial ideas or plans, and you need to adapt to these changes.  

The author spoke to Jay Shetty about how fatherhood altered his career goals and aspirations. He initially believed that professional success would bring him the most fulfillment, yet as he spent more time with his children, he realized that these moments with his family were far more meaningful. Therefore, he encourages parents to embrace the uncertainty of parenting and to understand that it is through the process itself that real growth and wisdom come.

Love What You Do

When it comes to career, Holiday believes it best to choose something you love, yet he cautions against tying your self-worth to professional achievements. He notes that many people get caught up in the chase for validation (hitting sales targets, receiving accolades, or obtaining promotions), only to realize that these external measures of success rarely bring lasting happiness.

Instead, the author suggests focusing on the inherent value of your work, the love for the craft itself. He told Jay Shetty that true success is measured by how much joy and fulfillment the process brings, not by the external rewards it yields. This applies both in career and parenting.

Jay Shetty also notes how easy it is to lose sight of the internal rewards as responsibilities mount and the demands of life increase. People often focus on things like income and status and forget the deeper reasons they pursued their passions in the first place. Therefore, he and Ryan Holiday encourage the listeners to reconnect with their original motivations and to ensure that their work is something they genuinely love.

The Backstage Effort

Jay Shetty and Ryan Holiday reflect on the importance of the often invisible, behind-the-scenes work that precedes success. Jay shares his own journey, explaining that before achieving recognition for his online work, he spent over a decade honing his skills without any publicity. From public speaking training to mentoring and coaching small groups, he dedicated years to improving his craft. Long before fame or financial reward, Jay committed to his passion, working offline for no money or recognition. He highlights how this period, though seemingly unnoticed by the public, was crucial in shaping who he is today.

Holiday explains that "overnight success" is largely a myth. Social media often paints a misleading picture, where someone's first viral post or sudden success seems effortless. Yet Holiday emphasizes that success is typically the result of countless repetitions and slow, steady progress. His book, The Obstacle is the Way, initially sold only 3,000 copies in the first week. However, through gradual growth and persistence, it has now reached millions of copies sold. This is a journey that took years, and it didn't happen in the first weeks or months after the book was launched.

The author explained to Jay Shetty that the slow, methodical process of building something meaningful prepares you for future opportunities. Holiday acknowledges that he wouldn't have been ready to achieve success sooner than it happened. He states that you must keep turning it like a flywheel until it gains momentum. Only then are you truly prepared to meet the moment when success arrives.

Don't Seek Only Success

Jay Shetty soon realized that life isn't just about success; it's about collecting meaningful experiences, skills, and relationships. He also gained knowledge and experience in various domains (becoming a monk, attending public speaking classes, and working at Accenture) before finding his calling. It wasn't about chasing one goal but allowing various experiences to shape his journey.

Ryan Holiday considers that everything in life can provide material for personal growth. Whether it's facing setbacks or unexpected events, each experience teaches us something valuable. He embraces the Stoic conviction that "the obstacle is the way." Therefore, the author believes these moments contribute to a larger development process; he is happy to contribute to a future he may never live to see, such as planting trees whose shade he'll never sit under.

Raise a Reader

In a world dominated by digital screens and constant distractions, Holiday highlights the importance of instilling a love of reading in children. As someone who has spent his life immersed in books, Holiday shares with Jay Shetty how crucial reading is to both personal and intellectual development. Yet he asserts that reading should be a pleasurable experience rather than a forced one.

When it comes to motivating your children to read, Holiday suggests finding books that align with your child's interests. The goal is to build a love for reading by making it an exciting and enjoyable activity. The author allowed his son to explore books that spoke to his passions instead of pushing him to consume primarily classical literature. Once children develop a habit of reading, their curiosity will naturally lead them to explore a wide variety of topics, sparking a lifelong love of learning. He explained to Jay Shetty that the key to raising a reader is to nurture curiosity and to create an environment where books represent gateways to new worlds, ideas, and knowledge.

Be There for Your Children

Parents generally want what's best for their children. However, Holiday stresses that while it's natural to want to provide your children with material comforts, the most important thing children need is their parents' presence. Time, attention, and genuine connection matter far more than gifts or financial stability.  

In his parenting journey, the author noticed that the simple act of spending time with his children - whether it's playing, reading, or just being together - builds a deep and lasting bond that material offerings cannot replace. Similarly, Jay's most treasured childhood memories are those moments of undivided attention and care from his parents.  

Presence is more than just being physically available; it's about fully engaging in your child's world. When parents are attentive, they create an environment of security and love that shapes the child's emotional and psychological development. Moreover, parenting is not about perfection but about consistently showing up, even in the smallest moments, and being there for your child in ways that truly matter.

Reparent Your Inner Child

How we feel in childhood has a lasting impact on us as adults, too. Holiday explained to Jay Shetty that many adults carry unresolved wounds from their childhood, particularly from a lack of validation or approval from their parents. This unmet need often manifests in the drive for external success as people seek validation from achievements, promotions, or societal recognition.  

Yet the author warns that no amount of success will heal these old wounds. Instead, your adult self must learn to reparent your inner child by giving yourself the love and validation you lacked during your formative years. Only when you acknowledge the (intentional or unintentional) gaps left by your parents can you take steps to provide yourself with the understanding, care, and validation you need to thrive. It will also allow you to become a better parent, break the cycle of unmet emotional needs, and ensure that you are present and emotionally available for your children.

Get in Touch With Your Feelings

Because parents want to see their children succeed, they resort to different forms of encouragement. However, pushing a child to do something may sometimes harm their evolution. Jay Shetty remembers his parents alternating between encouraging him and pushing him forward.  

Ryan Holiday believes it is important to be attuned to the current situation and root your reaction in the present. Let go of the fear of future outcomes and focus on what is happening at this very moment. He explains that sometimes, we overreact by thinking that small issues - like a child refusing camp - will turn into long-term problems when in fact, it's often just an isolated situation.

Holiday stresses that disruptions in our plans don't signal failure. Staying grounded in the present allows for greater patience, understanding, and the ability to make better decisions at the moment, whether for ourselves or our children.

Parental Guilt

Many parents struggle with the feeling that they are not doing enough, whether balancing a demanding career with family life or managing the pressures of raising children in a modern world. Holiday explained to Jay Shetty that this guilt often stems from genuine care for your children and the desire to be a perfect parent. However, he also warns against letting guilt take over, as it can lead to burnout and stress. Instead, he suggests admitting that nobody is perfect and striving for balance rather than perfection.

Ryan Holiday and Jay Shetty agree that feeling guilty can signal that something in your life needs adjustment; however, it should not be the driving force behind your parenting decisions. Focus more on creating meaningful moments of connection with your children rather than trying to be perfect in every way. The key is to show up consistently and with love and understand that mistakes are a natural part of the parenting journey.

More From Jay Shetty

Listen to the entire On Purpose with Jay Shetty podcast episode on “Ryan Holiday ON Why You Need to Reparent Your 14-Year-Old Self & How to Overcome the Fear of Not Being Good Enough” now in the iTunes store or on Spotify. For more inspirational stories and messages like this, check out Jay’s website at jayshetty.me.