Churchill on Failure

Life is filled with failure, but if you learn from failure, then it is rich with success. This month in 1893, Winston Churchill failed entrance to Sandhurst Academy. He turned to tutoring but kept his eyes on the far horizon. His lessons are timeless and began near that moment.

Late in 1893, Churchill gained admission to Sandhurst, a military school – his third attempt. A year later, he graduated, in time for his father to see his effort, before dying in 1895.

Churchill was resilient, and why? Because failure, grief, and adversity teach us, if we are willing to learn. That same year, he joined the military, lost a dear friend, organized her funeral, and was deployed to Cuba, and on to India. He never hesitated. Called, and he went.

Within three years, he was back in England, began writing, He was always writing – and evolving, or so he thought, from war to politics. God is in charge. Churchill would learn that.

By this month in 1899, Churchill was talking at conservative meetings. When the country entered the Boer Wars, he went as a journalist, got captured, imprisoned, escaped, reentered the army, kept writing, in time returned to Britain to share what he had learned.

After joining parliament, and becoming an undersecretary, he wrote a book about his father. He discovered he liked writing books. Good things, because he eventually wrote 43.

In coming years, he got a minor appointment, lost an election for parliament, and married Clementine, maybe his best decision. Eventually entering Parliament, he managed riots, got appointed head of the Admiralty, like Secretary of the Navy, in 1911.

Now the current got fast. World War I, Gallipoli, unfairly blamed for failure, he resigned, now a Dad with two kids. Incredibly, he rejoined the military at a low rank, and joined the troops in the trenches. War over, he rejoined government briefly.

By 1921, he was painting. Painting? Yes, he liked it and painted the rest of his life. That and cigars and scotch and winning … well, let’s not get ahead of things.

More time, another child, and almost dying from appendix, he kept writing, as time ticked down toward WWII. By 1924, respect for him blossomed into Chancellor of the Exchequer, or something like Secretary of the Treasury. By 1928, he was abolishing taxes everywhere.

The world in a frenzy after the Great Depression, he published his biography. In 1933, Hitler became Chancellor of Germany, and Churchill’s focus tightened, life mission before him.

Churchill, with a special knack for looking around corners, urged the British government to up-fund defense, not down-fund it. By 1938, Churchill was all over Prime Minister Chamberlain, urging he tell Hitler not to take Czechoslovakia.

Chamberlain had no ear for Churchill’s warnings, and declared “peace in our time,”  imagining appeasement works. It never works. Churchill knew.

In May of 1940, after Hitler invaded Poland, Churchill set the record straight, made clear the stakes. Suddenly, things changed in an epic way. Churchill became Prime Minister.

You know the rest, Dunkirk, “we will fight on the beaches…,” entrance into the war, Great Britain alone, a relationship with FDR budding, Churchill’s address to the US Congress, his mother an American.

From there, four long years of war, victory, defeat at the polls, rising again to the prime minister, eventually checking out in his 90s, after a lifetime of faith, determination, resolve to win for the future, and a fondness for one-liners, scotch, and cigars.

When I think back on Churchill, who molded a generation, and taught us never to give up, his wit comes back like shafts of light in a dark room.

“Kites rise highest against the wind, not with it.” So true, in all things. Truth and resolve, work and belief, always surpass drifting. Or fortitude under attack: “You have enemies? Good, that means you have stood for something some time in your life.” May we all …

Of course, you know them as well as I do, his warnings – true now, as then. “An appeaser is one who feeds a crocodile, hoping it will eat him last” and “success consists of going from failure to failure, without loss of enthusiasm.” Is he not right?

Maybe three of my favorites will close today out. He noted, “Courage is what it takes to stand up and speak, and courage is what it takes to sit down and listen.” We need both.

Then, he wrote, and I believe “All great things are simple, and many can be expressed in a single word: Freedom, Justice, Honor, Duty, Mercy, Hope.”

My favorite, however, maybe the opening to one of his post-WWII books. He writes, succinctly, a life philosophy. “In War: Resolution. In Defeat: Defiance. In Victory: Magnanimity. In Peace: Goodwill.” Is that not the extract?

So, as we all know, life is filled with failure, but if you learn from failure, then it is rich with success. Churchill taught his generation, and he teaches us still.

Robert Charles is a former Assistant Secretary of State under Colin Powell, former Reagan and Bush 41 White House staffer, attorney, and naval intelligence officer (USNR). He wrote “Narcotics and Terrorism” (2003), “Eagles and Evergreens” (2018), and is National Spokesman for AMAC. Robert Charles has also just released an uplifting new book, “Cherish America: Stories of Courage, Character, and Kindness” (Tower Publishing, 2024).