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Learning to Fail

The Fabulously Flawed Winston Churchill

Why you should care

Because if Churchill can struggle to unlock his potential, then so can you.

The black limo exited the iron gates next to Big Ben and was greeted by a reverential crowd. The imposing figure in the back — bowler hat, bulldog face, cigar and iconic two-fingered salute — was heading home from his last day at work.

Fifty years ago, Winston S. Churchill retired from the House of Commons, his home for 64 years, leaving behind a legacy of wartime greatness, as well as a number of major setbacks — from academic failure and political exile to a crushing postwar electoral loss. He’s a hero today precisely because he was both triumphant and fabulously flawed — and persevered throughout, emerging from each disappointment tougher than before.

“To improve is to change. To be perfect is to have changed often,” he said. It was to be his lifelong theme.

Color photo of Winson Churchill coming out of black car

Source: Corbis

No Scholar

From the word go, Winston was a pain in the arse — defying parents, teachers, political opponents and even death.

At school, Winston was stubbornly defiant — one teacher called him the “naughtiest small boy in the world.” He did so poorly that his father, the 7th Duke of Marlborough, assumed he’d end up a “social wastrel.”

Continuous effort — not strength or intelligence — is the key to unlocking our potential.

– Winston Churchill

Desperate to win his father’s favor, Churchill set his sights on a military career. But he failed the Sandhurst entrance exam, twice, and just barely got in to the military academy on his third attempt.

“Continuous effort — not strength or intelligence — is the key to unlocking our potential,” Churchill would later say.

At the academy, Churchill discovered his talent for logistics and strategy. He finished eighth in a class of 150, and the pragmatic skills he mastered would be put to good use in numerous campaigns, both on the ground and in war rooms.

The Bigger the Risk

Churchill joined the 4th Hussars, a cavalry regiment in the British Army, in 1895, leaving a few years later to serve as a war correspondent in South Africa. He was persuaded to join a routine armored train trip, which went well until they were ambushed by Boers.

The journalist, 25, didn’t wait for the officers to take charge. He organized men to clear the railway line — bullets whizzing past — and got the wounded to safety. Churchill went back to help those engaging the enemy, only to find they’d already surrendered, and he was taken prisoner.

Churchill escaped within four weeks, hiding on trains and in mines until he made it to safety in Durban, where he regaled listeners with tales of his exploits. He wrote about his death-defying escape, and the acclaim he garnered led to his first electoral victory and seat in the Commons in 1900.

BW portrait of Winston Churchill

2nd Lieutenant Winston Churchill of the 4th Queen’s Own Hussars in 1895

Far From Perfect

By 1915, World War I was underway and Churchill had been named First Lord of the Admiralty. He advocated a campaign to seize control of the Dardanelles Straits and western Turkey, believing it could force Turkey out of the war while encouraging neutral countries to support the allies. Churchill was sure the plan would work, but some on the War Council were hesitant.

Decision-making muddles and delays meant a fortified Turkish force was ready and waiting, and the disastrous campaign ended with around 200,000 Allied casualties.

Churchill was forced to resign his post, suffered political and public ridicule, and slumped into a depression.

But he didn’t let it keep him down for long. Unable to sit still while World War I raged, he was soon back in uniform in Belgium.

Haunted by Gallipoli, Churchill would later fight both Roosevelt and Stalin over the timing of the D-Day landings.

Beaten but Not Out

Later, when Germany surrendered in May 1945, Churchill’s approval rating as prime minister reached 83 percent. He wanted to see the war through on the Pacific front, but Labour was pushing for an election. Confident he’d face a grateful electorate, Churchill acquiesced — and just two months after defeating Hitler, British voters rejected their warlord with a landslide Labour victory, making Clement Attlee prime minister.

Churchill had been so focused on war that he had failed to gauge the public’s desire for peace.

Profoundly hurt, but deeply respectful of the democracy his soldiers had fought and died for, Churchill took to his role as opposition leader with gusto — reclaiming the prime ministership in 1950.

Churchill remained in parliament until six months before his death in 1965. On his last day, colleagues paid tribute not only to his successes, but also his ability to overcome.

“Failure and success are, in their different ways, equal tests of a man’s character,” former Primer Minister Harold Macmillan said. “[Churchill] has overcome both triumphantly.”

As the British bulldog’s limo pulled away, a country bid farewell to its gloriously flawed hero.

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