Every year, November, December and January mark the Engagement Phase for my guys. It’s the stretch where we build habits, strength and discipline long before the season begins.
And let’s be real—this phase is tough.
Early mornings. Cold nights. Heavy reps. Mental battles.
Building habits is uncomfortable before it’s automatic and strength hurts before it helps.
That’s why these months require more than physical work.
They require context.
Because when you understand your history, you gain fuel for your future.
Educated. Inspired. Empowered.
I anchor this season in three pillars:
Education — Learning what needs to be learned to do what needs to be done.
That includes skills, baseball IQ, routines—and understanding the history of our game.
Like 1859, when the Henson Baseball Club of Queens played The Unknowns of Brooklyn in the first documented game between two African-American teams.
They weren’t just playing baseball.
They were claiming identity, space and dignity.
Inspiration — External fuel when internal motivation runs low.
Those men played during a time when simply organizing a game was an act of courage. When you know that, pushing through a tough workout becomes easier. Their story gives us wind when motivation dips.
Empowerment — Responsibility and authority.
History empowers because it shows what’s been sacrificed and what’s possible. When our players learn their baseball lineage, they take ownership of their habits, their development and their future.
Why This Matters Now
When the reps get heavy, you need meaning.
When habits feel hard, you need direction.
When motivation fades, you need roots.
That’s why the Engagement Phase isn’t just training—it’s identity work.
Educated. Inspired. Empowered.
History gives us each of these and each one helps our boys push through the toughest part of the year.
Because they’re not just preparing for a season.
They’re continuing a legacy.
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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