Confessions of a High School Baseball Coach Part 2

By: Trevor Winsor

Welp, tryouts are over! Practices have started. And now we are going into our first game as a squad. This will be my first game as a coach.

I remember what it was like opening day as a player. You tossed and turned all night in anticipation. You envision your first at bat or that first ball hit to you. You go through the play-by-play of the game finishing and you find yourself victorious. It’s quite the emotional experience.

Well, now as a coach I’m experiencing this all from a new lens. This new perspective has me thinking through the differences from being a coach and being a player.

Here are my confessions of the first game:



It was as if it was Christmas Eve and I knew I had presents under the tree! It was wild. I woke up around 4 am to hear my son crying. I tried to go back to sleep but found myself thinking about all of the situations and scenarios that I was going to experience at the game later that day. I was thinking through my approach to handling certain players or certain situations. I was mentally visualizing how I would coach.

This made me rock and turn and roll in bed. I couldn’t slow my brain down. I couldn’t stop thinking about how the next day would play out. Baseball is funny like that. It is so dynamic and so complex that you get caught up in thinking about the game for days on end.



It’s easy to want to make tons of corrections up front. Those first game jitters tend to wind the players up quite a bit and the natural pull is to try to knock them down. But as we struggled through the first 3 innings, I saw the need to allow them to fail.

My head coach gave me some feedback on my coaching thus far (because this is my first year doing it), and he told me “You have to let them come to you. Let them fail. Then let them come to you for coaching.” He’s right. If I just go in there and try to change everything all at once, my players will push back and be less receptive. But if they continue to fail and see the need for coaching and then they come to me, that’s the golden time for a coach.

I’m learning this as a new dad and definitely as a coach, people will fail and we don’t have to keep them from it. Failure is a part of life. We all do it.

And we all need to be allowed to fail. And all good players, probably all players period, always want to get better. And the desire to get better will drive a player to approach their coach. This gives me the greatest opportunity to affect change in their game. If they come to me first, they end up being more open and receptive to what I have to offer them.

You gotta let your players fail and anticipate them coming to you afterwards.



If you’ve ever coached at any level or any sport you know that coaching is just a blast!

Game #1 was spent making fun of situations and making fun of players as they struggle through their first at-bats, ground balls, and getting on base. I don’t think you can be a coach without a sense of humor. And baseball is a funny game.

Whether you’re making fun of a terrible throw during inny/outty or you’re making fun of an umpire, baseball will always bring lots of laughs. And it’s a game that you have to learn how to take everything with a laugh.

The truth is, as a coach I had more fun in our first game then I did when I was a player. Now, did I not have fun while I played? Of course not! I love every second of playing. But this was a new experience that brought more joy and fulfillment as I watched and helped young men get better at baseball. And I laughed the whole time!



The first game is exhilarating and so much fun! I honestly didn’t think I’d lose sleep over how excited I was to coach my first game, not to mention how great it was to win that first game 12-0.

People need to fail. Baseball is a game of failure. Your players need to learn how to fail and it helps that they will approach you once they do.

Laughter is a part of the game of baseball. You can’t really play this game without having fun. Ultimately this is a game for kids and we get to play it for many years (if you’re lucky).

Don’t take the game for granted, it’s a huge gift and we should always treat it that way!


Here is Part 1 of Confessions of a High School Baseball Coach: Tryouts

Continue Reading Confession of a High School Baseball Coach Part 3