Leadership: Mistakes Made and Lessons Learned

Leadership is a topic I am passionate about and the practice of Leadership has been an integral part of a majority of my life at this point. I was reflecting on my journey recently and realized that some of the most valuable lessons learned came from my struggles and mistakes versus my triumphs and successes. Often times the former precedes the latter.



My journey began when I was 15 years old as a Boy Scout. I imagine you have a familiarity with the Scouts given their long term existence in the States (most boys spend some time as Cub Scouts before transitioning to Boy Scouts to some degree. I was actually the opposite. I never did Cub Scouts but just rolled into Boy Scouts. Anyway…)

The elections for the Senior Patrol Leader (SPL, highest official Scout leadership position)  were approaching and my Dad suggested I should run. Initially, I wasn’t interested in running because I was working toward my Eagle Scout and if anything wanted to be less involved in Scouts upon completion of my final project. Being SPL would be an increase in time and responsibility week to week. I’d rather play golf every day after school and on the weekends (more on that later). Anyway, I ran for SPL and was selected to be the SPL for the next year.

Mistakes Made and Lessons Learned: Fortunately, this season in Leadership was marked by lessons learned more than mistakes made. Of course I made some mistakes. I was a bit timid at first. I was so soft spoken our first few meetings that one of the adult leaders stood in the back of the fellowship hall we met in and would raise his hands when I needed to raise the volume of my voice. Good times.

I learned a lot from this first foray into leadership, but the main lesson was this:

A Leader is always being watched. There is nothing more important than their example.

I participated in as many events as I could. I even went deep sea fishing (which for me is just deep sea sickness). Our fundraiser was selling firewood and I was out there every Saturday morning stacking, loading, selling, and unloading firewood. We sold more firewood than ever before. I wish I could say all of these decisions were my own, but the truth is my Dad was the one who reminded me of the importance of my participation and setting this example for all of the Scouts.


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Fast forward a couple of years. My Senior year of High School golf as the Co-Captain of a team that just won the District and Regional titles the previous season. We were a bit younger but still had plenty of talent mixed with some experience from the previous season. This was my 4th year on Varsity and my Junior year was my best individual season as well. Needless to say, expectations were high.


Mistakes Made and Lessons Learned: This season in leadership was marked by disappointment and failure. I struggled mightily throughout the season and was not one of the top 6 players by the end of the year meaning I missed the postseason.

My mistake was not simply playing poorly. That happens sometimes (especially in golf). No, my mistake was focusing on myself. I started out as the Co-Captain of the team but ended up shirking my responsibilities to the team. It was a missed opportunity to be a positive influence on the younger athletes on the team.

The lesson here is pretty clear to me now, Leadership is not about you.



A few years later I joined the US military as a soldier in the Florida Army National Guard. Shortly after joining, I met a ROTC recruiter on campus and found myself joining the Fightin’ Gator Battalion at the University of Florida. ROTC was military leadership on steroids and I came in 2 years behind many of my peers in the principles of military leadership.

Mistakes Made and Lessons Learned: I made many mistakes and learned numerous lessons during this season. I do want to take a moment to highlight how valuable it was to have an environment where I could make mistakes without significant consequences. Looking back on it now, that is a lesson I have carried with me as I seek to develop other leaders. You have to create an environment where leaders can make decisions and have space to fail.

As for my mistakes, I would say my biggest mistake was leading in a way that was inauthentic. Not everyone in the Army is the archetype you see in the movies. In fact (as I discovered later on), many officers in the military possess a very similar disposition to my own. I had to make the mistake to learn this lesson: Leadership must be authentic (be yourself!)


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I completed ROTC and commissioned as a Second Lieutenant in the Florida Army National Guard. My first official leadership opportunity as a commissioned officer came as a Platoon Leader. My responsibilities varied over the course of 8+ years as an officer and slowly increased over time to where I am today.

Mistakes Made and Lessons Learned: I’ve made my share of mistakes as an Army officer but my experience as an officer has been marked more by the lessons I have learned as a follower. I have served with and for very gifted leaders. In some cases, very different leaders. Different styles, backgrounds, and approaches but similar positive results. Although they were different, they shared one critical similarity: they truly cared for their soldiers.

Leadership requires you to care.

This lesson seems obvious, but in my experience it is sorely lacking in many organizations.


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For the last several years I have been an entry level operations manager in the hospitality industry and most recently transitioned to the food and beverage industry with a new organization. The organization I was in previously did a great job of defining their culture and giving young managers opportunities to be leaders. There IS certainly a difference between managing and leading. At times, I have been just a manager. Other times, I have truly been a leader.

Mistakes Made and Lessons Learned: In these organizations, and the military, there is a tendency to fall into a particular trap. If you are a leader, then you run the risk of falling into this trap. Heck, if you are a human you run the risk of falling into this trap.

The trap I am referring to is the comparison trap.

You’ve seen soldiers in their dress uniforms right? Well, all the stuff they are wearing was earned over time and through various acts of service and in some cases heroism. They earned the right to wear the items signifying their accomplishments. It has been easy to look to my left or to my right and compare myself to someone I perceive to be better because of their accomplishments.

Beware of the comparison trap!

This leads me to my final point and one of the leadership lessons I have learned over the years.

It is a mistake to define yourself by your successes OR your failures. 

Neither your successes or failures have any bearing on what you are capable of doing right now. Sure, people may define you by those things until you prove otherwise but it is foolish for you to do so.

John Wooden captured it best:

“Success is never final; failure is never fatal. It’s courage that counts.”

Thanks for reading!

– BA

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