What Sir Winston Churchill Taught Me About Mindset and Leadership

As an adolescent, this young man was rebellious, had the lowest grades in his class, suffered a speech impediment and was incessantly rebuked by his parents for his lack of conformity. However, Winston Churchill overcame countless obstacles and rose to the position of Prime Minister of the United Kingdom in 1940.  Churchill was one of the greatest wartime leaders of the 20th century, an exceptional writer, politician and much more. As leaders, there is much we can learn from Winston Churchill.

My wife and I recently took a vacation to Great Britain. During the trip, I grew increasingly more inquisitive about Winston Churchill. I wanted to know more about his life and leadership. While in London, we visited the Churchill War Rooms, which contained a thorough testament to the private life and public persona of Churchill. After our trip, I continued my study of this tremendous, yet controversial, leader.

Renowned for his rousing and passionate speeches, historical writings and steadfast countenance during the darkness of World War II, much of Churchill’s appeal is found in his mindset.

In examining the life of Winston Churchill, I noted 5 characteristics of his mindset that every leader can cultivate.

Embrace Challenges: Despite his parent’s criticisms, Winston set his mind to prove his worth. He became highly proficient in math and taught himself English history.  Winston’s father believed he wouldn’t amount to much in business or politics and encouraged him to pursue military service. Winston far surpassed his father’s expectations, as he was on the frontline of five wars and became a highly successful war journalist. He even escaped from captivity when he was a prisoner of war (POW).

When the odds stacked against Churchill, his resolve to never be defeated hardened. He responded with greater intensity to overcome whatever stood in his way.

Bounce Back: When Churchill made mistakes, which sometimes came in large doses due to his bold and sometimes unpopular opinions, he did not allow them to get him down. In lost elections, political defeats and failed bold predictions, he was often criticized. He was blamed in large part for the Dardanelles debacle during the First World War and was later demoted as a result. Regardless, Churchill moved forward from his failures.

Perhaps, most notably, after World War II, Winston lost his bid to be reelected as Prime Minister. His wife Clementine referred to it as a blessing in disguise. Winston went on to write his war memoirs during this time, spoke around the world and expanded his passion for painting.

How do you respond to letdowns and large scale failure?

Work Hard: During the war, eighteen hour workdays were the norm for Winston. He drove those who worked for him very hard, but drove himself harder. Upon waking, he began his workday in bed, making phone calls, writing and consulting. He put tremendous energy into everything he did. Known for his oration, Churchill worked hard on his speeches, crafting and reviewing each word. He would travel long distances to meet face-to-face with foreign leaders. His accounts of the World Wars are the result of endless hours of brilliant effort.

Even in his leisure activities such as painting, hunting and renovating their Chartwell home, Winston worked hard.

To be clear, I’m not advocating we work from dawn and late into the night. However, Churchill applied fervor, diligence and enthusiasm to all of his endeavors. To see results, we must do the same.

Manage Mind-Body Energy:  Churchill was known for and sometimes mocked for the way he managed his energy. Contrary to custom, once seated, he rarely would stand as others entered or left a room. When asked about his behavior, he talked of conserving his precious energy. To maintain his fervent work ethic, Winston prized his sleep. When permitted, his daily appointments showed a nap at 3 o’clock in the afternoon.

Today, managing our energy may look a bit different. Science proves we need exercise, movement and yes, quality sleep. Find the strategies that will work best for you. If we ignore this crucial need, we’ll drive ourselves toward burnout.

Be Joyous: Sir Winston led England through some of the most tumultuous years of the 20th century. He suffered many defeats and great victories. Through it all, he preserved a joyous attitude. He brought the House of Commons to roaring laughter on multiple occasions. Churchill loved collecting and telling jokes, often weaving humor into his speeches. He also loved people and relationships. He was grateful for the support and encouragement he received throughout his life.

After being named Prime Minister by King George VI on May 10th, 1940, he immediately wrote to his predecessor Neville Chamberlain to thank him for his support.

Fun is often overlooked when it comes to our work. However, those who enjoy their pursuits, find joy and happiness in them, often find greater success.

Great leaders are often characterized by their accomplishments. However, it is their mindset, attitude and resilience that often lead to their achievements. These 5 characteristics of Sir Winston Churchill’s mindset can be cultivated by you and me and can bolster our own leadership. To become a more successful leader, employ these qualities with fervor and consistency.

Question: What other mental attributes do you think are important for leaders? You can leave your comment in the section below this post.

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