Baseball: A Great Metaphor for Leadership, Business & Life

by candy barone Oct 01, 2023

Well, to be honest, I am bit sad writing this post. The regular season for my beloved Chicago Cubs has come to an end. 

They were so close … so many times. The division, at one point, and then the wild card race, both were high possibilities.

Until they weren’t.

It came down to execution at the end. Finishing the momentum that they started. Pushing through to the bitter end. 

Yet, that didn’t happen. In fact, the wheels fell off. 

The bullpen lost their rhythm and gave up far too many hits and walks. The errors from golden glovers was too many. And, the hits came too late. 

It got me thinking how life and business are a lot like baseball. 

In fact, one of my all-time favorite leadership books is The Cubs Way: The Zen of Building the Best Team in Baseball and Breaking the Curse by sportswriter, Tom Verducci.

In it, he lays out the 5-year plan Theo Epstein deployed during his time as the Cubs’ manager that successfully took them to the World Series in 2016, where they won in that prolific Game 7 and the notorious 17-minute delay. 

That series about killed me. All 7 games. And, there was both a joy and excruciating reliving of the anxiety as I read through Verducci’s words as he highlights every aspect of those games. 

One of the most memorable games for me during that World Series run was Game 4 of the NLDS between the Cubs and the Giants. As they were several things I found extremely noteworthy in regards to how leadership rose to the occasion during the 9th inning. 

Watch as I break down the three ways I witness leadership rise within the team, and how I feel can use this strategies to level-up your business and stay in the game:




Strategy #1: The Rally Cry

Both the offense and defense stepped up. It wasn’t one person who carried the team, but the collective effort of the whole that made the difference. 

The team came together in a way that created a massive ripple effect. Not only were the bat hot, where they were able to drive in four runs, Chapman (their relief pitcher) came in and had probably one of his best moments on the mound. It was magical and effective. 

Which lends me to ponder how you have structured your team …

  • Do you have the key pieces in places?
  • Is your culture strong enough to rally when you need it most?

Now, I am not talking about constantly winding and grinding your people into a frenzy and pummeling them into constant levels of burnout. 

No, I am talking about when it matters most … when the game is truly on the line, are your people positioned (and supported) in a way that they can rally and come together as a team to win the game?

The real wins come from a collective team effort, not from one individual. This starts from a shared clear vision, a space where people can feel seen, heard, and valued, and in recognizing the numan-ness of your people. 

Not every day can be a ‘knock-it-out-of-the-park’ grand slam day. Everyone has slumps, and misses, and failures. Is your team assembled in a way to cover those ‘off’ days. 

Because a “rising tide lifts all boats”

Some questions to consider as you evaluate your own team:

  • Are you leveraging and positioning your people to play at their highest and best level?
  • Do you have space for and allow room to fail?
  • Are you giving them opportunity to rise when the occasion calls for it?
  • Are you providing both support and accountability to bring out the best and the leadership within your people? 
  • Is your team truly positioned for the rally to close the gap?

Strategy #2: Never Lose Hope

It’s astonishing how much of our valuable time we spend worrying about what others are doing, and assessing how we compare to what we perceive success looks like through that lens. 

We look at the ‘scoreboard’ and think: “the competition is winning … game over.” And, then you throw in the towel and concede to a loss before the game is actually done. 

As the famous saying, from sportswriter, Dan Cook, goes: 

“It’s not over until the fat lady sings.”

Meaning if the game is still in play … it’s not over. Anything can happen in the final stretch. Hell, if you are a Chicago Cubs fan, you are accustomed to that ‘hail mary’ attempts in the 9th inning with two outs, often with a 3–2 count in the box, to boot. 

Think about it. How many times have you chalked a game up to being lost when there still was more game to play?

We do this is both our life and businss. We often shortchange ourselves and give up right at the moment where the breakthrough is possible. 

In the Human Design work I do with clients, this is often the point of frustration that occurs. Instead of recognizing the frustration as a momentum builder, a refueling, so to speak, to get us ready for the next breakthrough, we decide we’ve failed and stop just as it’s about to get juicy.

Some questions to consider as you evaluate your own team:

  • Do you carry the belief that anything is possible?
  • Are you aligned to the mighty mission and your compelling why?
  • Are you keeping the end in mind?

You’ve got to be willing to take that last stretch. That when you think you’ve given 100%, give a little bit more. And, there almost always is a little more. 

I facilitate an exercise in my workshops that illustrates this point. I ask everyone for raise their right arm straight up over their head as high as they can go. I emphasize “stretch as far as you possibly can.” And, then I said, “now, stretch higher.”

And, everyone, every time, stretches their arm up even higher. 

Because it’s the human conditioning to protect ourselves, to hold back slightly until we can assess the lay of the land. We keep our potential in reserve, and only give as much as we think we need to. 

I mean why would you want to empty the tank if you didn’t need to, right?

So, we hold back. We play small. We wait to see if we really have to show up. We give up prematurely … before the game is over. 

Imagine if, instead, we gave it our all in the final moments. That we did “one more thing” as Ed Mylett talks about on his podcast, The Ed Mylett Show, and in his book: The Power of One More.

Or, as I like to say:

“Go big, or go bigger. There is no going home.” 

The game is on the line … and, it’s not over yet!

Strategy #3: Your Fans and Support System

Game 4 against the Giants was played in San Francisco. Meaning the Cubs were the visiting team and the majority of the fans in the stadium that very late night in September 2016 were Giants fans. 

However, what transpired in that 9th inning was mind-blowing. The moment the momentum shifting and the Cubs began to rally, you could hear people chanting: “Go Cubs, Go!”

This small conglomerate of fans rose to the occasion and got loud. You see, it doesn’t take an entire stadium to turn the tide … but, rather, only a small group of connected, engaged, amplified voices to do so. 

They came together in unison, and even from the TV, the energy was palpable. It was electric and you would have thought the game was happening at Wrigley Field. 

That’s the power of community, of your raving fans and champions. They can remind you of who you are. They can elevate your own belief in yourself. They can help you refocus on your mission and goals. 

Some questions to consider as you evaluate your own team:

  • Are you surrounding yourself with people, and a community, that loves you, supports you, lifts you up, and champions you?
  • Are you tapping into a support network when you feel like you’re in the 11th hour, and your back is up against the wall?
  • Do you have people in your life and in your network to remind you who the f*ck you truly are?

If you don’t have people who are willing to champion you and rally around you, then it’s high time to rethink who’s in your network and who you are choosing to do business with. 

Your community is everything!


Which leads me back to the close of this current season. 

We rallied, we didn’t lose hope, and we supported our team. And, yet … the reality was it just wasn’t enough. 

And, that happens. 

You are not going to win every time. That’s not the point. The journey is the gift, not necessarily the outcome. 

For even when you do all the things, or don’t, it’s how you choose to show up that matters. Leadership is about doing the thing anyway. About showing up anyway. About playing the game anyway. 

Baseball is about percentage, averages and probabilities.

It’s a great metaphor for life: as one calculated move, one small tweak, one ‘lucky’ break , one pitch, or one at-bat can literally change the trajectory of the entire game in a moment. 

Sometimes you win. Sometimes you don’t. Or, perhaps … you always win if you gave it your best shot. As the legendary Babe Ruth said:

“Never let the fear of striking out keep you from playing the game.”

For more, please follow me on Instagram: @candy_barone or Linkedin:

Be sure to tune into my podcast: Aligned As F*ck

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