Winston Churchill


The Courage to Decide


From a young age, Winston Churchill was an independent thinker. As an excellent communicator, a bold risk-taker, and an opportunist, Winston Churchill is thought to be one of the most important Prime Ministers of the United Kingdom, and a leading force in the Allied victory in World War II. Churchill’s ability to make bold decisions and learn from his failures is a large part of what sets him apart as a historic leader. As Prime Minister, he understood the need to make forthright decisions that would not sit well with everyone but that he could predict would do the best for his country, and ultimately, the world. For this reason, Winston Churchill was a brave model of decision making.

I never worry about action, but only about inaction.

– Winston Churchill

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“Criticism may not be agreeable, but it is necessary. It fulfils the same function as pain in the human body; it calls attention to the development of an unhealthy state of things. If it is heeded in time, danger may be averted; if it is suppressed, a fatal distemper may develop."

—Winston Churchill

As a politician, Churchill’s most outrageous idea was not allowing appeasement to stand in the way of his country.

As human beings, we are hardwired to care what other people think, since our survival used to—and sometimes still can—depend on other people’s opinions of us. The problem, today, is that too often, our worries about other people’s approval and their feelings towards us hinder our ability to make decisions that best suit ourselves—or in a politician’s case, our countries.

Politicians walk a tightrope. Their job is to care about other people’s opinions, since their role is to represent their constituents and vouch for what they want. It is inevitable, however, that pleasing some constituents comes at the price of disappointing others, since not everybody has the same goals or values. Politicians can’t make everybody happy; we’ve seen this time and time again in our lifetimes, especially throughout the coronavirus pandemic.

“Before you can inspire with emotion, you must be swamped with it yourself. Before you can move their tears, your own must flow. To convince them, you must yourself believe.”

—Winston Churchill

Churchill, however, was a revolutionary in that he didn’t get bogged down in appeasing people; rather, he fought for what he believed in and for what he knew was right.

When Hitler announced his plan to take over part of Czechoslovakia in 1938, leaders of France, Italy, and the United Kingdom legally supported the annexation by signing the Munich Agreement.

Although they may have not genuinely appreciated Hitler’s decision, these leaders—one of them being UK leader Neville Chamberlain—signed the Munich Agreement, giving Hitler the go-ahead. It is most likely that Chamberlain wanted to appease Hitler, in order to avoid future negative relations.

“Politics is almost as exciting as war, and quite as dangerous. In war you can only be killed once, but in politics many times.”

—Winston Churchill

Returning from Munich, Chamberlain boasted of his achievement, telling constituents, “My good friends, for the second time in our history, a British Prime Minister has returned from Germany bringing peace with honour. I believe it is peace for our time.”

Of course, Chamberlain was sorely mistaken. He, like the leaders of France and Italy, had endorsed and enabled Hitler’s violent and aggressive approach. Hitler now had the confidence to take over other European countries in the coming years.

In stepped Winston Churchill, who became Prime Minister two years later. Churchill made clear from the beginning that he was not interested in “appeasing” Hitler and the Nazis. Churchill inspired his country’s constituents with a powerful speech, “We Shall Fight on the Beaches,” that boasted integrity and the will to fight against Hitler, rather than the intention to sit idly by.

“To improve is to change, so to be perfect is to change often.”

—Winston Churchill

Churchill’s ability to take risks, make bold decisions, and act with integrity rather than cowardice proved extremely valuable as Nazism continued to spread through Europe. Although it took six years for the Allied forces to win the war, many believe that it couldn’t have happened without Churchill’s bravery, integrity and bold decision making.

In Steven Hayward’s book Churchill on Leadership, Hayward writes that Churchill had three rules for decision making: always keep the main crux of the problem in sight; know how to balance both sides of a decision; and have the ability to change the course of action if new information is presented.

Churchill was enthusiastic about, rather than afraid of, decision making and he was ready to accept consequences and learn from them, rather than shrink in the face of failure. Churchill provided opportunities for people to take risks and learn from their experiences, and measured other people’s strength by this same metric, rather than by how often they succeeded.

“Every day you may make progress. Every step may be fruitful. Yet there will stretch out before you an ever-lengthening, ever-ascending, ever-improving path. You know you will never get to the end of the journey. But this, so far from discouraging, only adds to the joy and glory of the climb.”

—Winston Churchill

Luckily, we are not all tasked with leading a world superpower in the face of a brutally threatening dictatorship. Perhaps, however, we can learn some important lessons from Churchill’s bravery: no matter what you do, you will not please everyone, and appeasement is not what you should be after anyways. You must act with integrity and use your values and beliefs to guide you. Only then will you become an effective leader and a sound decision maker.

“An appeaser is one who feeds a crocodile—hoping it will eat him last.”

—Winston Churchill

Historical biography

Churchill was born into a wealthy family in England in 1874. He attended a fancy boarding school as a child, where he was ostracized by the other students for his poor behavior and academic performance. After switching schools multiple times, Churchill settled at the Harrow School, where he prepared, in his last years there, to enter the military. After two unsuccessful attempts, he was admitted to the Royal Military Academy on his third try.

Churchill began his military career as a second lieutenant in the British Army. He was interested in war, and travelled to Cuba, America, and India to witness different battles. While travelling, Churchill became very well-read and knowledgeable about politics, and formed nuanced beliefs that aligned somewhere between Liberal and Conservative ideals. Upon returning home to England, he began giving speeches and was eventually selected as a parliamentary candidate for the Conservative Party in 1899, but was not elected.

Throughout the next decade, Churchill acted as a journalist, covering news stories around the world, and was even taken as a prisoner of war in South Africa. He returned to England intermittently as a home base, where he ran again as a Conservative candidate in the 1900 general election. This time, he won, making him a Member of Parliament (MP) at age 25.

“Politics is the ability to foretell what is going to happen tomorrow, next week, next month and next year. And to have the ability afterwards to explain why it didn't happen.”

—Winston Churchill

Little did Churchill know, his political career would last for the next 55 years, during which he would act as Home Secretary, First Lord of the Admiralty, British Secretary of State for War, Chancellor of the Exchequer, and serve two terms as Prime Minister.

Although these early years were formative, Churchill is best known for acting as Prime Minister of the United Kingdom during WWII.

Before WWII began, Churchill famously warned the British government about Hitler’s rise to power and the dangers of Nazi Germany. When Prime Minister Neville Chamberlain resigned in 1940, Churchill took the reigns, and inspired his citizens to fight against Nazi Germany, no matter what it took.

Churchill was a fighter, and is known as one of Britain’s toughest Prime Ministers to date. His attitude influenced his constituents to be bold in their fight against Nazi Germany, and to never give in to the enemy. As a result of his extremely influential rhetoric, Britain was successfully led through one of the harshest periods of history, and the Allied forces were eventually successful in defeating Nazi Germany.

“Those who can win a war well can rarely make a good peace, and those who could make a good peace would never have won the war.”

—Winston Churchill

Churchill in the media

Books by Churchill

For Free Trade (1906): In the 1906 General Election, Churchill switched parties and ran as a Liberal, focusing his campaign on the issue of free trade. This book was his defense of free trade, where he argued that free trade encourages international relations, interdependence, and peace.

The World Crisis (1923): This book is Churchill’s account of WWI, published in a vast six volumes.

My Early Life (1930): This book details Churchill’s early life until his marriage, describing a foundation set by his childhood for a successful and impactful political career.

Marlborough: His Life and Times (1933): John Churchill was the first Duke of Marlborough and an ancestor of Winston Churchill. Churchill’s 1933 book is his biography, which later inspired subsequent volumes in 1934, 1936, and 1938.

Great Contemporaries (1937): This book is Churchill’s anthology of 25 short biographical essays of famous people.

Atlantic Charter (1941): Written with Franklin D. Roosevelt, this book set in print the American and British goals for a post-WWII world.

The Second World War (1948-53): This is a four-volume series written by Churchill chronicling the Second World War.

A History of the English Speaking Peoples (1956): Churchill’s history of Britain is written in four volumes. It details Britain’s colonies and possessions throughout the world, leading up to Britain’s current role as a superpower on the world stage.

Books about Churchill

Churchill: Four Faces and the Man (1969): This book is a collection of essays written by five authors, who describe his five different identities: statesman, politician, historian, military strategist, and human being (man). This book founded the British school of ‘Churchillians.’

Winston Churchill: His Life as a Painter (1990): Written by Churchill’s daughter, Mary Soames, this book is a refreshing glimpse into Churchill’s private life, and the vices that kept him sane as an esteemed Prime Minister and politician—his painting.

In Search of Churchill (1994): Written by his official biographer Martin Gilbert, this six-volume and 7285-page textual series goes into depth about the life, identity, and strengths of Winston Churchill. There is no better researched biography out there.

Man of the Century: Winston Churchill and his Legend Since 1945 (2002): Written by author John Ramsden, this book biographically studies the construction and perpetuation of Winston Churchill’s post-war reputation. It particularly addresses how a common perception of  Churchill was arrived at, and how the maintenance of this perception influences world attitudes about the current United Kingdom.

Movies about Churchill

World War II: When Lions Roared (1994): This engrossing film follows fictional depictions of Churchill, Joseph Stalin, and Franklin D. Roosevelt as they lead the way for the Allies to become victors of WWII.

The Gathering Storm (2002): This historical fiction film chronicles the many hardships Churchill underwent during 1934, in the professional and personal realms of his life.

Into the Storm (2009): This movie is a dramatization of Prime Minister Churchill’s reign as Prime Minister during WWII.

Winston Churchill: Walking With Destiny (2010): In this documentary, the life and work of Winston Churchill is examined.

Darkest Hour (2017): This war drama film studies Churchill’s decision making process, as he chooses whether to sign a peace treaty with Hitler or to continue fighting against the Nazis.


Biographics. (2018, February 13). Winston Churchill Biography: In the Darkest Hour [Video]. YouTube.

Blech, B. (2017, December 2). Winston Churchill: Three definitive ideas that changed the course of history. aishcom.

Ghosh, P. (2015, January 23). Winston Churchill and his wartime passion for science. BBC News.

Greenspan, J. (2014, April 9). 10 things you may not know about Winston Churchill. HISTORY.

His speeches: How Churchill did it. (2009, April 6). The International Churchill Society.

Kindy, D. (2020, February 24). How Winston Churchill endured the blitz—and taught the people of England to do the same. Smithsonian Magazine.

Murray, S. (2019, April 9). 7 leadership lessons from Winston Churchill.

Nicholas, H. G. (2021, January 20). Winston Churchill. Encyclopedia Britannica.

Paul Addison's top 10 books on Churchill. (2018, February 22). the Guardian.

Strauss, V. (2012, May 18). Best commencement speeches never given. The Washington Post.

Top 5 Fun Facts for about Winston Churchill | World War II Leadership | Educational Cartoon. (2019, January 2). YouTube.

Who was Winston Churchill and why was he important? (2019, February 14). BBC.,most%20famous%20British%20prime%20minister

Winston Churchill. (2001, October 30). Wikipedia, the free encyclopedia. Retrieved February 17, 2021, from

Winston Churchill in politics, 1900–1939. (2008, January 12). Wikipedia, the free encyclopedia. Retrieved February 17, 2021, from,_1900%E2%80%931939

About the Authors

Dan Pilat's portrait

Dan Pilat

Dan is a Co-Founder and Managing Director at The Decision Lab. He is a bestselling author of Intention - a book he wrote with Wiley on the mindful application of behavioral science in organizations. Dan has a background in organizational decision making, with a BComm in Decision & Information Systems from McGill University. He has worked on enterprise-level behavioral architecture at TD Securities and BMO Capital Markets, where he advised management on the implementation of systems processing billions of dollars per week. Driven by an appetite for the latest in technology, Dan created a course on business intelligence and lectured at McGill University, and has applied behavioral science to topics such as augmented and virtual reality.

Sekoul Krastev's portrait

Dr. Sekoul Krastev

Sekoul is a Co-Founder and Managing Director at The Decision Lab. He is a bestselling author of Intention - a book he wrote with Wiley on the mindful application of behavioral science in organizations. A decision scientist with a PhD in Decision Neuroscience from McGill University, Sekoul's work has been featured in peer-reviewed journals and has been presented at conferences around the world. Sekoul previously advised management on innovation and engagement strategy at The Boston Consulting Group as well as on online media strategy at Google. He has a deep interest in the applications of behavioral science to new technology and has published on these topics in places such as the Huffington Post and Strategy & Business.

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