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You are here: Home / About Diamond Directors / Why August, September and October are Your Most Important Months

Why August, September and October are Your Most Important Months

posted on July 29, 2026

As we enter the final days of our Application Phase (May, June and July), I find myself reflecting on what this season is truly about.

Application is where players take everything they have learned during training and attempt to execute it in competition. It is where preparation meets performance. The game exposes strengths, weaknesses, habits and gaps.

But once July ends, everything changes.

From August through October, we enter what I believe is the most important season of player development: The Assessment Phase.

Assessment is not about proving what you already know.

It is about discovering what you still need to learn.

It is the season to try new things, make mistakes, ask better questions, experiment without fear and, ultimately, determine what works and what does not.

For me, there is no greater objective during this phase than developing one trait:

Athleticism

Many people mistakenly believe athleticism is something you’re born with.

I disagree. Athleticism can absolutely be developed.

I define athleticism simply: Athleticism is your ability to make things happen.

It is critical thinking expressed through physical action.
It is solving problems when there is no perfect answer.
It is making adjustments faster than your opponent.

Because the truth is simple: Everything that must be learned cannot be taught.

At some point, every player must think independently, trust their instincts, adapt under pressure and solve problems in real time.

That is athleticism.

Athleticism Must Be Taught

Young players need coaches who intentionally teach athleticism.

Not just mechanics.

Not just systems.

Not just drills.

Teach players how to observe.
Teach them how to adjust.
Teach them why mistakes matter.
Teach them how to think under pressure.
Teach them how to compete without fear.

Athleticism Must Be Caught

Teaching alone is not enough.

Players must also catch it.

Athleticism is contagious.

Players learn by watching teammates take risks.

They learn by observing coaches who encourage creativity instead of punishing mistakes.
They catch confidence.
They catch courage.
They catch resilience.

Culture teaches as much as instruction.

Athleticism Must Be Practiced

Finally, players need opportunities to actually be athletic.

Too many environments overcoach every movement.

Every swing.
Every throw.
Every decision.

Eventually, players stop thinking.

They simply wait for instructions.

That is not development.

Development requires freedom.

It requires responsibility.

It requires ownership.

As I define it:

Development is the deliberate effort to value and empower learners to obtain personal mastery and excellence through nurturing and training.

5 Ways to Develop Athleticism

1. Make More Mistakes

Mistakes are not failures.

They are feedback.

Players who never make mistakes are usually avoiding growth.

2. Learn From Every Rep

Reflection creates improvement.

Ask:

What happened?
Why did it happen?
What will I do differently next time?

3. Take Calculated Risks

Growth requires courage.

Playing safe may protect today’s performance, but it limits tomorrow’s potential.

4. Practice Under Stress

Pressure reveals what players truly know.

Create practices that force decision making, adaptation, communication and recovery.

Don’t remove the stress.

Teach players how to thrive within it.

5. Surround Yourself With Development Coaches

Development coaches see beyond today’s box score.

They coach for who the player can become, not simply who the player is today.
They understand that long term growth often requires short term discomfort.

Why Many Coaches Struggle With Development

Most coaches genuinely care about players. But many are judged by one number: wins.

Winning matters. It should. But winning is the outcome.

Development focuses on the behaviors that produce winning over time.

Those behaviors are the real key performance indicators.

Decision making.
Adjustment.
Confidence.
Communication.
Resilience.
Awareness.
Athleticism.

When those improve, winning becomes more sustainable.

The Cost of Poor Athleticism

Players who lack athleticism often:

  • Wait to be told what to do.
  • Panic when situations change.
  • Repeat the same mistakes.
  • Struggle to make adjustments.
  • Depend on mechanics instead of instincts.
  • Lose confidence under pressure.
  • Become predictable competitors.

They may know baseball.

But they struggle to play baseball.

There is a difference.

Why Fall Matters

That is why I believe August, September and October are the best months of the year for player development.

Not because games are more important, but because experimentation is.

This is the season to challenge assumptions.

Play different positions.

Learn new movements.

Try different approaches.

Fail.
Recover.
Reflect.
Grow.

The players who embrace the Assessment Phase often make their greatest improvements before the next competitive season ever begins.

By the time spring arrives, they are not simply more skilled.

They are more athletic.

And athletic players don’t just execute what they’ve been taught.

They make things happen.

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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