Learning from Failure: Winston Churchill and the Evolution of a Leader

909 words | 4 page(s)

As a boy, Winston Churchill grew up enthralled by paintings and objects at Blenheim Palace depicting the exploits of his great 18th-century ancestor, John Churchill, first Duke of Marlborough. Marlborough had risen to greatness on the battlefields of Europe during the War of the Spanish Succession, leading England to victory over the armies of France, England”s deadliest enemy. Churchill always felt certain he, too, was destined for greatness defending his country from conquest by a powerful enemy. He would exhibit extraordinary leadership qualities first as a young, late-Victorian era officer fighting the wars of empire and, later, as the stalwart defender of a beleaguered England struggling to survive a powerful German bombing campaign and the threat of invasion by victorious armies of the Third Reich. It is a core belief of the British nobility that greatness is an inherited quality, but it is impossible to separate Winston Churchill and his accomplishments from his education and the remarkable adventures of his youth. Winston Churchill may have been born into greatness, but his education, training and superhuman initiative combined to make him great.

Churchill, like many scions of great families of the English nobility, lived a lonely childhood, left in the care of servants and sent to prominent boarding schools, as was the practice among the aristocracy. Churchill”s condition was not helped by a speech impediment that plagued him his entire life. Rigid Victorian educational standards were challenging for the young Churchill, and yet when he took the entrance examination at age 12 to get into Harrow, he was fortunate to have his below average Latin prose test graded by a remarkable instructor,

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named Welldon, who was capable of seeing the tremendous potential beneath the young man”s shy exterior. “It is very much to his credit,” Churchill wrote in his memoir. “It showed that he was a man capable of looking beneath the surface of things: a man not dependent upon paper manifestations” (Churchill, 2010, 16). However, he found his Harrow days largely depressing, discouraged by his subpar academic performance and the fact that he rarely saw his parents, even at school events designed for parents to attend. However, it was during his Harrow experience, unhappy though it was, that Churchill began to find within himself the resolve and inner resources that would see him through his greatest challenges.

In 1893, Churchill pursued his desire to enter Sandhurst, England”s famous officer training academy, though again his entrance exam scores were barely adequate. It was here that he learned a code of English manliness that proved invaluable during his service in the Sudan and, later, during the South African war, during which he was captured. Despite gaining entrance to Sandhurst, his father responded with little but criticism and an unmistakable disappointment over what he considered an underachieving son. From a physical standpoint, Churchill was of below average size, without the strong constitution required of the typical Sandhurst cadet, though the Sandhurst “regime of drill, physical training, equitation eventually helped Winston to overcome his infirmities” (Keegan, 2007, 30). Some have claimed that it was an overwhelming desire to earn his father”s approval that drove Churchill to succeed despite his shortcomings, but there can be little doubt that the harsh training he received at Sandhurst was important to his success on the battlefield and to his development as a leader under extraordinary circumstances.


It is difficult to overstate the influence that the Victorian hero ethos had on young men on the make. There was no higher aspiration than to gain glory in battle on behalf of the British Empire. This inculcated an almost kamikaze fanaticism in young British officers, and could lead to horrific slaughter on the battlefield, where death in the pursuit of victory was thought to bestow an eternal chivalric glory. This environment undoubtedly made a profound impression on Churchill, who never truly separated from this Victorian mindset. It was this dedication to an anachronistic value system that sometimes called Churchill”s leadership qualities into question. His ill-founded faith in the disastrous Gallipoli landing in 1916 proved a near-fatal setback in his political and military career. But Churchill had learned that confidence, or learning to exhibit self-confidence in the face of setbacks, is essential to being a good leader.

One of Churchill”s secretaries wrote that when he took over as Prime Minister after the Chamberlain years, the image of confidence and industry that Churchill brought to the job and to Whitehall in general were key to inspiring confidence in others (Best, 2005, 167). In other words, to inspire confidence, one must exhibit confidence. This set the tone for his leadership during the darkest days of World War II, when Hitler seemed unstoppable. “It was Churchill”s own opposition to all forms of defeatism that marked out the first six months of his war premiership and established the nature and pattern of his war leadership” (Gilbert, 2004, 27). Considering the setbacks he suffered early in his life and education, it is remarkable that Churchill became the most indomitable leader of the 20th century. His education showed him what it would take to succeed as a leader, but it was his personal fortitude and utter unwillingness to accept defeat that set him apart.

  • Best, G. (2005). Churchill and War. London and New York: Hambledon and London.
  • Churchill, W. (2010). My Early Life: 1874-1904. New York: Simon and Schuster.
  • Gilbert, M. (2004). Winston Churchill”s War Leadership. New York: Vintage Books.
  • Keegan, J. (2007). Winston Churchill. New York: Penguin.

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