October marks the official arrival of fall. But in baseball, Fall Ball is August through October—a season of experimentation. It’s when hitters try new things, discover what doesn’t work and lean into what does.
November through January becomes the winter grind, when we build habits and strength around what we’ve learned.
This window is also pivotal for players charting their futures. Some are stepping into their final tournaments, aiming to secure scholarships and showcase their skills against the best of the best. Others are younger, trying to figure out which travel team will guide them toward their dreams of college baseball—or even the pros.
It’s an exciting but stressful time. And it’s easy to slip into two traps: wandering and wondering.
Wandering and Wondering
Wandering is aimlessly moving without direction—jumping from team to team, drill to drill or showcase to showcase with no plan. I’ve seen players wear themselves out chasing everything but arriving nowhere.
Wondering is wrestling with the questions: What should I do? Who should I do it with? How should I move forward? Wondering without clarity creates anxiety, but when rooted in purpose, wondering can lead to wisdom.
And that’s where it all comes back to the why.
Too many players today are playing for the likes—the social media highlights, the clout, the attention. But here’s the truth:
The likes without the love won’t last.
I know this personally. As a player, I chased the likes. I didn’t love the game and my career didn’t last. As a coach, I do it because I love it—and that love sustains me.
5 Questions to Keep You from Wandering and Wondering
To move from wandering aimlessly to walking with purpose, every player (and parent) needs to wrestle with these five questions:
- Why am I playing this game?
The answer should be deeper than likes or clout—it should be rooted in love, growth and purpose. - What is my ultimate goal?
Scholarship? Pro ball? Lifelong lessons from the game? Clarity here sets the direction. - Who am I surrounding myself with?
The right coaches, teammates and mentors sharpen you. The wrong ones distract you. - How am I developing consistently?
Development isn’t random—it’s built through habits, discipline and systems that align with your goals. - What am I willing to sacrifice?
Time, comfort, distractions—success requires trade-offs. The love of the game makes the sacrifices worth it.
Opening the Conversation
These aren’t just questions to be asked once and forgotten. They should become ongoing conversations between players, parents and coaches. Because when you anchor yourself in your why and move with intention, you stop wandering, you stop blindly wondering and you start walking boldly toward the future you were meant to build.
So, as October arrives and the leaves change, ask yourself, “Are you playing for the likes—or for the love?”
Because the likes without the love won’t last.
Remember: Intelligence tops being smart.
For more information, visit www.diamonddirectors.com today.
If you found this inspiring and thought-provoking, or if you have any questions, comments or concerns, add me on Discord and let’s go deeper.
C.J. Stewart has built a reputation as one of the leading professional hitting instructors in the country. He is a former professional baseball player in the Chicago Cubs organization and has also served as an associate scout for the Cincinnati Reds. As founder and CEO of Diamond Directors Player Development, C.J. has more than 22 years of player development experience and has built an impressive list of clients, including some of the top young prospects in baseball today. If your desire is to change your game for the better, C.J. Stewart has a proven system of development and a track record of success that can work for you.
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