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Failure: Learning to Overcome Adversity

By: Capt. Christopher “Matcha” Little

Listen to this article on Podcast: Here

You fear failure, you are uncomfortable by it, and it often prevents you from reaching your full leadership potential. When you ask someone if people like to fail, the answer is always a confiding no. I argue differently and even welcome failure as it comes knocking at my door. You should fail and take risks as a leader, though not deliberately. If you do not fail, you are staying inside your comfort zone, something a leader should never do. It would be best if you always strived to improve. Failure helps you to become a better leader by overcoming adversity, abiding by humbleness, and being able to mentor others in a more concise demeanor. Failure allows you to know defeat, overcome it resiliently, keep a positive attitude when times get tough, and allows you to understand the next time you face a similar encounter; you can channel the setback you had previously and overcame. Being able to accept risk with the possibility of failure is a pinnacle aspect of a good leader.


“Success is stumbling from failure to failure with no loss of enthusiasm.”

– Winston S. Churchill


Attitude is everything in both life and leadership. People are attracted to positively mannered people, and conversely, negative people invite people with a negative outlook into their sphere of influence. You’ve all seen this in the work environment real world. Think of a real-life example you've had in life or career that has been shaped by failure and how your attitude helped you overcome that failure. For me, it was failing at Officer Training School (OTS) my first time around. Similar to Officer Candidate School (OCS) in any other service but the United States Air Force, it is roughly three months along with a robust syllabus focusing on leadership and followership skills, sprinkled with a myriad of academic tests and quizzes. Of the academic tests we had to take, I found out quickly military tests were a lot different than my previous test taking experiences. I failed the first test, which followed me around like a nagging mosquito for the rest of my time there. I had also failed at the Leadership Reaction Course (LRC), which was something everyone had to pass to progress to the next phase of training. In our mid-term feedback about a month and a half in, the snowball effect had been working to full force. I was behind the curve of where I needed to be as an Officer Trainee (OT). During my mid-term feedback, it was apparent: I had failed.

I had to swallow my pride, say goodbye to my peers who would graduate ahead of me, and even accept the fact I would have to march in the same graduation parade in a few short weeks biding my fellow OTS peers adieu. I remember being in a dark place during that time. I failed hard. I would have to spend another month and a half at OTS redoing things I had previously failed at passing. I had two options as I saw it: to quit or to get out of the pity party I had created in my head, learn from the experience, and overcome the second time around. Once I integrated with my new flight of roughly twelve people, I realized I fit in perfectly. Through my past experiences, I was able to become a mentor and a teacher, the failure I had endured earlier made me a de facto leader in the flight. I had been there longer, seen more, knew the game, and ultimately had learned to overcome and embrace the suck. I wanted to share the experience with my fellow flight-mates. One instance, previously mentioned, that stood out was the LRC. Having done the LRC already and not passing my first time, I saw this as my chance to shine and overcome failure.

I ended up putting together a PowerPoint presentation of what the LRC was, how our flight could overcome it, brief a shared mental model, and ultimately have the goal to pass as a team. Unlike my last class, every single person executed the LRC obstacle course above average. Was this a coincidence? Was all of us passing a testament to me failing before and being able to teach others how to learn from my failures? I think it is. This course tested both leadership and followership skills in each. My Flight Commander (Flt/CC) believed in me by allowing me to even give the brief to the flight, which was a non-standard thing to do during a structured day of classes. He saw leadership skills in me that were not as apparent as before, but only because I had failed previously. I learned to be a better, more effective leader only by first knowing failure. Defeating the LRC exercise was the first test. In the end, I did pass OTS, but with a different purview than most. I respect it differently. One that I still appreciate to this day because I had to overcome adversity, change my attitude, not quite, and ultimately win when it wasn't sure I would. These are characteristics which have helped me along the way throughout my seven-year career thus far.


“Only those who dare fail greatly can ever achieve greatly.”

– Robert F. Kennedy


You don’t go into OTS or life events knowing or thinking you will fail. When you go into operation, task, mission, or problem, you shouldn't either. Know that it will happen though, whether you like it or not at some point. Without risk, there is no reward. Your attitude after failure is what sets you apart from other leaders and peers. Will, you quit from failure? Will you learn from the experience and move on to the next obstacle in your way? Alternatively, will you go a step beyond and teach others what your failure brought you and how not to let it happen again? As a leader in your organization, military or not, you need to have your subordinates know failures will occur, but should not be accepted. It would help if you let them know, and demonstrate through example what overcoming failure can be. Share stories that you have had in your life about failure and what you did to overcome it. Everyone has known defeat in life, but people handle it in different ways. Be the leader that sets the example that failure is going to happen and put forth a plan on how your team can learn from it. There is a difference between accepting failure and setting the example in your organization to overcome failure and pave a way forward. Be the latter. It works for me.

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