Moving Beyond Regret Cleaning Up Messes — Lessons From The Diamond

I’ll be the first to admit that I am not a big fan of giving regrets a chance to shape my life. That said, God knows I’ve made enough mistakes to fill the average Major League Baseball stadium a few times over.

Recently, as I drove past a youth baseball field, memories flooded back to when I coached the sport. I coached at the rec level and travel level. I coached tournament teams and had the honor of coaching high school baseball for half a decade.

I have always taken a good deal of pride in how I coached and the ways I was able to help boys grow into solid young men. However, it has never occurred to me that I might have had a hole in my game.

A few days ago, I saw one of my former players on LinkedIn and barely recognized him. These little guys grow up. He was a friendly kid but not one who was considered one of the better players. But there he was — a solid young man doing his best to make it in the world. It was then that something profound hit me.

A lightbulb turned on, and when I allowed myself some time to process what that light illuminated — here is where I landed.

I was a dynamic coach for the kids who were the better players. The highly skilled players who knew they would be in the lineup every night loved playing for me. I was their kind of coach. But what about the kids who batted eighth or ninth or sat on the bench most of the year? What kind of coach was I to them?

Full confession — I believe I failed those kids. Those who needed the most got the least. Kids placed in my care found reinforcement of what they had already discovered on their own; they weren’t quite good enough. They would get my leftovers in terms of time and commitment.

And now, I deal with the regret of a blown opportunity to reach those kids more meaningfully. One of these kids had a seriously sick sibling. Every minute of every day that must have hurt. Another dealt with the pain and agony of parental divorce. Some just struggled with their confidence and self-image. So much so that one player even took his own life, and I missed every sign because my focus was more heavily on the elite players. Yeah — I wear that reality because it’s true. I should have known. But I chose not to invest in a skinny backup player who battled internal demons that eventually convinced him that this world wasn’t worth the fight.

I’m reminded of this truth every time I hear the song ‘Why’ by Rascal Flatts. Here are a few lyrics.

Now in my mind I keep you frozen as a seventeen year old. Roundin’ third to score the winning run

You always played with passion no matter what the game. When you took the stage you shined just like the sun

Oh why, that’s what I keep askin’. Was there anything I could have said or done

Oh I, had no clue you were masking a troubled soul, God only knows what went wrong, and why you’d leave the stage in the middle of a song.

Every kid had a story — even the elite ones. But I was more interested in the results. The wins and losses took precedence. Somehow, that felt okay in the moment. I failed these kids, and for whatever reason, it took a decade to figure that out.

There was good — lots of good. But there were also lots of missed opportunities to help the kids who struggled. I failed them, and I regret that.

Today, I lead folks in corporate America. And some are better performers than others. It’s easy to focus on those at the top of the leaderboard. But I’m starting to believe that authentic leadership is essential, especially when it comes to supporting struggling individuals. Can I help? Can I take the time to listen? Really listen — not just listen to check off a box. Can I encourage and cheer on those who need a lift? Or should I cut my losses and move on to someone else? Leaving that person with another failure and more challenging days.

Or do I double down on the “winners” and ensure they get my energy or attention? I don’t think this is an either/or construct. Maybe the answer lies in the idea that each one of these people is human. And their value isn’t determined by their place in the batting order or on a sales leaderboard. They are fellow humans. And that’s enough to give them sufficient value to care deeply for each one. No exceptions.

There’s an old saying that goes like this; “we are all just walking each other home”.

Even those in the back of the crowd.

Especially those in the back of the crowd.

Never give up on folks. And never leave anyone behind. No exceptions.