Leaders Keep Swinging

November 1, 2022

by Stephen T. Messenger

The World Series began this week with the Philadelphia Phillies facing off against the Houston Astros. One thing I’ve noticed is that many of the great players on both teams take some big swings!

Now, many of these big swings result in big misses. The batters are putting a significant amount of energy into trying to hit home runs, and often come up short. But, if you want to achieve something big, you must swing for the fence. In leadership terms, you must take a bold risk to achieve a bold goal.

Learning from a Missed Swing

It’s okay for leaders to take big swings, and I argue it should be encouraged. I can look back on my life and remember several times where I could envision a home run, only to miss the ball as it sailed by. I prepared for these dreams, swung big, and missed.

  • My dream of West Point crashed after being unable to get past the initial nomination phase
  • After injuries, I was twice medically dropped out of Army Ranger School
  • Working for a Fortune 500 company, I applied for a big promotion and was passed over
  • For a resident PhD program, I was rejected in the application process
  • Every summer my dreams of doing a flip on a wakeboard end painfully

We can all look back on our lives and remember the times we struck out. And often in our minds, the failures overshadow the great things we accomplish. But every miss is a chance to learn.

If we’re never missing, it probably means we’re not swinging hard enough.

The Journey of Walking

It’s like a toddler learning to walk. No parent yells at them when they fall. There’s an “Uh oh, get back up!” moment, and the toddler tries again. They constantly fall, learn something, and give it another go.

Toddlers have unlimited opportunities in learning to walk. In baseball, there are three strikes, nine innings, and 162 games. In leadership, there are thousands of chances to try, fail fast, learn, and then try another way or attempt something new.

Because when we make contact off, our gains are much larger.

Swinging for the Fences in Philly

In honor of the Phillies World Series berth, some Philadelphia history of swinging big:

The founding fathers signed the Declaration of Independence knowing that if they missed, they would all be executed for treason. This decade, we’ll hit 250 years of thriving.

George Washington crossed the frozen Delaware River on Christmas Night placing the entire fate of the fledgling Nation on this operation. This home run saved the army from dissolving.

In more recent news, Rocky Balboa’s odds of beating Apollo Creed were scarce. Yet Rocky faced Apollo down and first tied, then defeated him in the ring.

Big swings lead to big gains! It’s about putting every ounce of energy into tackling Big Hairy Audacious Goals (BHAG) knowing that you may miss entirely, but always with the hope of connecting.

Risk vs. Gamble

It’s not just about taking big swings, but about preparing for those opportunities. A risk is a calculated move to seek a great advantage. It comes with planning, foresight, mitigation, and understanding the right time. It’s about taking that big swing when you believe a payoff is coming.

A gamble is pure chance, like closing your eyes and hoping to make contact. A gamble is a Las Vegas roulette wheel or investing in a flip property when you haven’t read the market nor calculated the repair costs.

Failures Lead to Success

The failures in my life noted above were risks. I was prepared for all of them and put time and effort into achieving them. I still swung and missed. But every time I learned something and kept swinging.

I can look back on my life and see the times I’ve stretched for some difficult goals and connected.

  • Applying to an Army ROTC college scholarship and getting it
  • Volunteering to attend Airborne School and earning jump wings
  • Trying to complete a doctoral program at night and now entering the dissertation phase
  • Competing for command positions and nominated to command an Army Installation

Each failure is one strike of many. Your people need to see a leader who’s not afraid to keep swinging. If you watch balls go by, your people will too. Everyone deserves a leader who will allow them to take chances and underwrite their failures.  

If you and your team are never swinging for the fences, you’ll never see those great gains.

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