Great Leadership and Failure, why it’s essential

Seth Whitmer
13 min readJul 8, 2021


We try to hide it and don’t ever want to talk about it. In job interviews, we shun it and look down upon it. People associated with it are lessors and undesirables. Yet, it is an essential and inevitable experience every leader must have. Failure, it’s what makes us a great leader!

In motivational speeches or memes, we will often see things such as, “it took Edison 1,000 failed attempts to invent the lightbulb.” However, I would argue this is not a real failure. The invention of the lightbulb certainly depicts success through adversity but not failure. It gives the impression that if we just keep working hard enough, we will eventually be successful. In reality, failure never occurred, as the end result was a success.

So, it could be argued that learning from failure is not a failure at all but a success. But this may undermine its importance. Perhaps failure is the wrong word, perhaps there is a better way to describe it, unfortunately, I have not yet found it. In this essay, I will look at failure as a professional event. Failure is a broad word, but for the purposes of this essay, its definition will be kept more narrowly defined. Simply put, it is not accomplishing or achieving the aspired outcome that leads to the culmination of a negative event. This could be a service line failing to launch, a team failing to work together, or simply being fired from a job.

So why is it necessary for a great leader?

During my undergraduate degree, I was accepted to an internship as an Administrator in Training at a very successful healthcare organization. The CEO told me that I would not actually benefit from the program. I inquired as to why. I will never forget what he told me. He said that they had refined things so well and had become so successful I would not learn how to improve. I countered that seeing the best would help me to emulate the best. For many years, I have wondered which of us was right.

Throughout my career, I was placed in many difficult situations. I was able to turn around failing organizations, drastically improve operating margins, increase productivity, and much more. For a time, it seemed I couldn’t fail, and I actually thought I wouldn’t ever fail, after all, that was for people that were incompetent. People who failed made bad decisions or didn’t try hard enough. I did not make bad decisions, and I worked harder than everyone else.

Then one day, it hit me. It was difficult for me to see it coming because I had never experienced it before. Complete and utter failure came so suddenly and swiftly that I was completely caught off guard. It shook me to my core and had a major impact not only on my professional career but also on my family. Looking back, I have often reflected on what bad decisions I might have made that led to my sudden failure. As I have talked through it many times with friends and peers, I am honestly still not sure there was a bad decision that could have been prevented. I hoped and prayed that this would be my one and only failure, as I didn’t think I could ever endure it again. I thought to myself, “I have learned from this, and therefore it won’t happen again.” However, I have ended up with many failures in my life. Not the same failures, fortunately, but still complete and utter failures. It has taken some time for me to come to terms with this. After all, don’t our failures and our successes define us?

Interestingly, the actual failures were not the hardest part to deal with, it was living with the failure as part of my life. Especially at a time when an individual’s failures can be posted online in which it remains etched into a surface stronger than iron or steel. For a leader, a failure that is on the internet often means it will remain forever in the open for all to see. Your failure becomes immortal in a place that offers no forgiveness or redemption. You cannot hide from it, and so somehow, you must learn to live with it.

Through many discussions with successful leaders, I have learned that in the past, failure could be hidden. For example, a vast number of rural health CEOs have, at one time or another in their career, been fired as a CEO. If it was publicized in the newspaper, it would quickly be forgotten without the internet to keep the article forever in memory to anyone interested. It allowed them the illusion of constant success in their career, and that move was just a career move, not due to a failure. Perhaps this is what has contributed to the perception that any failure is undesirable.

In all my conversations with leaders, peers, and mentors, and as they have opened up to me to discuss theirs, I can see the pain from these experiences that they still feel. Rarely do they want to talk about them, but as I discuss mine, it helps them open up. A consistent theme that I have noted in these conversations is how they changed because of their failures. That change was often different depending on the individual. Often making them more humble and able to sympathize with those they lead, being more cautious and patient in making decisions, or giving them the realization of what is most important in life and completely changing their perspective.

At the same time, as I reflect on some of the worst leaders I have known in my career, they have been those who have refused to admit failure or exhibit a lack of experiencing it. This is perhaps the greatest tragedy of failure, failing to learn from it.

Gratitude for my failure:

As for me, I have found immense gratitude for my extreme failures. I have learned invaluable lessons, and my outlook and perspective have completely changed from what it once was. While others may look at failures as an undesirable blemish, I view them as an essential experience in maturity as a successful leader.

Think of an athletics team that never experiences defeat. Every single year they win the championships. Think of what their attributes must be like. Is that the type of person you want to lead your team? Perhaps your answer is yes, but I have had those leaders over me, and I have never been more miserable in all my life. Their lack of failure created in them arrogance, pride, prejudice, entitlement, and a demeaning view of those that were not like them. That’s not the team I want to be part of. A great leader must understand failure and have an appreciation for it, to allow them to be able to motivate and inspire.

Additionally, I have seen that those who experience failure, yet still refuse to acknowledge it or learn from it, are likely to repeat mistakes of the past. They lack the humility and assurance to successfully bring a team together. They are combative and forceful in an effort to portray a self-image of confidence and success.

While failure is no guarantee that someone will become a great leader, I believe it is essential in order for greatness to be achieved. In the movie, The Core, Bruce Greenwood, plays, Commander Richard Iverson. In his explanation to Major Rebecca Childs, as to why she isn’t ready to lead, he stated, “you’re not really a leader until you’ve lost.”

Why does leading require losing? One of the first reasons that come to my mind is the breaking point. Those that have experienced failure have learned what it’s like. They have learned what they can handle and how to recover. The failure itself is not the defining moment but rather our actions afterward. When failure hits, do we fall apart mentally and physically, and if this happens, can we recover? If you have been through it, you know the answer. Burnout, addiction, and many other physical ailments are all signs of stress and can quickly lead to mental and physical breakdown. But if you have learned how to work through failure, you know how to get through it, how to recover, and how to cope.

In a study, the National Review of Economic Research found that CEOs are likely to die sooner due to stress. The increased oversight from governance boards shaves years off of life. According to the Rural Health Research Center, Rural hospital CEOs have the largest turnover rates versus any other profession in the United States. Now not all of that turnover is due to failures, but I personally know many that didn’t leave on their own accord. Rural hospital boards are extremely difficult to navigate and perhaps one of the most stressful CEO roles that can be had. Governing boards in healthcare generally lack the administrative skill and often are more worried about perception than anything else. Often, they seem to run with abandon and carelessness of the repercussions to the CEO. Not knowing failure can set the CEO up for disaster in their relationship with the governing board. Let me explain why.

Failure teaches lessons that are otherwise very difficult to learn.

Lesson 1: Humility. Often humility is thought of as debasing ourselves and not gloating. However, it is much more than this. Humility allows us to have compassion and sympathy for others. To understand what others, feel is essential, as you cannot lead without understanding how your team may feel. When individuals fail, how can you lift them without knowing how to do so yourself? Humility is recognizing that you are not in control, rather, you can only influence. Sometimes there is nothing that can be done to succeed as failure is imminent. Understanding this can help set the stage for whatever is next, and rather than falling into despair, we can still have hope for what is next and work towards that end. Humility allows us to have hope and overcome the fear of the end. Humility is understanding that the world does not revolve around us, and failure is a natural part of life. It is simply another teacher to help us become more than what we are. Humility instills a calm confidence, while dispelling arrogance.

Lesson 2: There is life after death. Despair comes as we believe everything is collapsing, such as thinking to yourself, “I have failed, and my career is over.” We assign all of our value to success, giving the belief that if we fail, we have no worth. Those that have learned from failure know that this is not true. The joys of life are able to continue, the world continues to go around. However big our failure may seem to be, the ultimate failure is not learning from it and being able to find the joys in life because of it. As the Roman poet said, “Endure and save yourself for days of happiness ahead.” The one thing I have learned time and time again, is that it is never the end so long as I continue to press on.

Lesson 3: Finding beauty in imperfection. Those that have successfully overcome failure know that there is beauty in imperfection. They know that while we strive for the ideal, the journey is more wonderful and amazing because of the failures along the way. Failure does not define the beauty, but rather our response to it and overcoming it, is the beauty. Those who have learned from failure, have the patience to help others who fail and rejoice with them as they overcome their failures. After one of my professional failures, as I saw the imperfections in others, I was also able to recognize their quality. The mentality and expectation of win or die left me as I understood more of the emotions and experiences that others whom I was trying to lead were experiencing. I was able to look past their flaws and recognize their heart, their worth, and the value of work performed day after day. Rather than being quick to condemn, I understood their perspective. I realized I could not fix every flaw in the organization without destroying it because the organization was made of people who were each flawed and imperfect. Rather as the leader, my role was to bring them together and help them magnify their value.

Lesson 4: Gratitude: Learning from and embracing failure brings perspective, and being able to see the good and bad enables gratitude. If one has only ever known success, they will often take for granted their fortune. Gratitude brings people together with an emotional bond. It is infectious, and as it spreads, it lifts and encourages. I saw this firsthand in graduate school. We were tasked to give our team members feedback on how each of them could improve. As each person took their turn, a feeling of anger, defensiveness, and divisiveness prevailed among our group. When at last, my turn came, I stated that I was not going to follow suit. Instead, I chose to express what I was grateful for to each individual. A physical transformation occurred as I watched the anger and divisiveness melt from each person’s face. Afterward, each member of the group came to me individually, expressing appreciation for my words and how they changed the mood of the group. Gratitude softens the heart and allows a leader to reach and touch others in a way that would otherwise be impossible. Those that have successfully overcome failure know this truth and have the ability to live it.

Lesson 5: The past does not define us, and our failures do not define us, but how we move forward does. Choose to live in the present and do not look back with regret. It took me some time to learn this lesson. It was perhaps one of the hardest for me. We tend to judge others by their past experiences or choices, and it is natural for us to do this to ourselves as well. Often, we can be our worst critics. We made the decisions we did, and nothing can change that now. Perhaps it was not even our decisions but circumstances outside of our control. The past still cannot be changed. The only thing we can change is the present. Within our current limits, we can change and decide what to do now. The person that I am now is what is important. The challenge is that others will continue to judge us by our past successes and failures, and in a professional sense, this can be the most difficult part of overcoming failure. Sometimes, time is the best healer, and in this case, as we focus on changing the now, our past can be redefined as people experience the new refined person we have become. As I have learned to embrace my failures, I have found a deep gratitude for them. I am able to reflect and see the positive changes in myself that have come because of those experiences. In each case, I can see that I would not be in the fortunate position or be the current leader that I am without those failures.

Lesson 6: Connected to lesson 5 is forgiveness. The Latin root of the word forgiveness is perdonare, which means to give completely, without reservation. I will attempt to illustrate this deeply personal experience in my attempt to make this point of forgiveness. In a very personal experience, I was deeply hurt by those I was very close to. I went to church with them, I considered them my friends. They knew my children and my wife, and our kids went to school together. They were prominent members of the community. Yet, in a cruel action, they fabricated stories and rushed a judgment to condemn me. I was devastated. I felt betrayed. Not only had they hurt me personally, but my family as well. Yet, this was one of the greatest moments of my life. I had been prepared for this since I was a young boy. I needed to forgive; otherwise, these hurt feelings would destroy me. This was not easy to do, as I saw them often. They would not speak to me but instead shunned me and my family. I wish I could say that I simply chose to forgive them, and that was it, but it was much more complicated than that. It took time, and for me, it took the aid of Heaven to finally forgive, to give completely without reservation. One of the pivotal moments of this process took place at our church, where I was able to serve those that had hurt me. While they spurned me, I looked upon them with love. While the feelings of pain may remain, I am able to also see them with love. “To forgive is not to forget. The merit lies in loving in spite of the vivid knowledge that one that must be loved is not a friend. There is not merit in loving an enemy when you forget him for a friend” (Mahatma Gandhi). I still look upon the loss of their friendship with great sadness, but the anger is gone. Being a great leader requires the ability to forgive.

A lack of these lessons learned can put a new rural hospital CEO at a disadvantage with almost certain doom, or any leader for that matter. Whereas, a CEO that possesses this experience or these lessons will be able to weather the difficulties of navigating the complexities of leadership. It will help them keep things in perspective, understanding how and when to change things. Certainly, these lessons are not a surefire to success, but they will help in getting there.

So, who was right during that meeting so many years ago, the CEO overseeing my internship or me? Was I able to learn from a successful organization? Yes, absolutely! But perhaps my greatest teacher was later when I experienced my own failures. The way I responded and what I learned and became afterward is what has defined me, and certainly, my failure is a part of that. A gratitude that I now know that I could not see at the time. That gratitude has helped me to live with that failure, rather than looking back with shame and regret, I can look back with gratitude for what I have learned. It has enabled me to help lift others and to have compassion and the ability to inspire in a way that I could not before. Certainly, it is still a challenge in how others view me because of my failure, but I know how to live with it now. I have learned how to change and become something so much more than I otherwise would have been, and in that regard, it was all worth it. And hopefully, this essay will help others to learn the value of failure and look upon it with a different view of appreciation than previously held.



Seth Whitmer

Hiram Seth Whitmer is a visionary leader and influencer with a passion for executing the complete turnaround of healthcare organizations