Youth Baseball & Parenting — How to Support Your Son's Journey Without Making It Your Own | Ep. 185
by Keith Glasser on Sep 18, 2026
The youth baseball years are where the foundation of a player's relationship with the sport is built — and the decisions families make during those years, from travel teams and organizations to the conversations that happen after every game, have a lasting impact on whether a young player falls more in love with the game or slowly starts to pull away from it. In this episode of Dugout Dish, Andy and Keith have one of their most important and most personal conversations yet about youth baseball, parent mindset, and what it genuinely takes to help a young player develop a healthy, sustainable, and joyful relationship with baseball during the years that matter most.
What we cover:
- When to get into travel baseball and what should actually be driving that decision for your family rather than what everyone else around you is doing
- How to evaluate travel teams and organizations during the development years and what qualities matter most when choosing the people you surround your son with at a young age
- The parent mindset — how to actively support and facilitate your son's baseball journey without consciously or unconsciously making it your own
- Why understanding that this journey belongs to your son and not to you is the single most important shift a baseball parent can make — and how to actually live that out in practice
- How to help your son build a healthy and genuine relationship with the sport so that he still loves showing up, loves competing, and loves the process as he gets older
- The car ride home — why the conversation that happens in the twenty minutes after a game is one of the most powerful and most underestimated moments in a young player's development
- What constant negative feedback and criticism after games does to a young player's relationship with baseball over time — and how it becomes one of the biggest reasons players walk away from the sport before they ever reach their potential
- Alternative approaches to the car ride home that actually strengthen your son's relationship with the game and help him process both success and failure in a healthy way
- How to guide and support your son toward his long term goals in baseball in a way that keeps the love of the game intact through the inevitable ups and downs of the development years
- What Andy and Keith wish more baseball parents understood about the youth years and what they have seen make the biggest difference in the players who go on to play college baseball
Whether your son is just starting out in travel baseball or is deep in his development years — this episode will make you think differently about your role in his journey and give you practical strategies to be the parent he needs you to be.
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