The Mindset of a Serial Failure

Written by James

Hey Tribe,

Welcome back!

Recently I’ve become fascinated with Sir Winston Churchill.

The reason?

Throughout history there is no leadership figure with so many documented failures, who inevitably kept bouncing back.

His political career was littered with examples where Churchill was nearly right or just plain wrong about a situation.

Regardless, in the world of politics there is no near miss, you are just a failure.

And Winston failed so much, yet still managed to become Prime Minister during the biggest conflict of the 20th Century – an achievement which just defies logic!

The man stubborn in his beliefs.

The year is 1932.

After serving several high positions in the cabinet, his political credibility is zero, with a general view that he was an over the hill, Edwardian era throwback. Churchill had many enemies, which extended to people in his own political party.

Despite this, in seven years’, time he would go on to replaced Neville Chamberlin as Prime Minister.


He was very vocal and very right about his early analysis on the threat of Nazism.

"Germany is arming, she is rapidly arming, and no one will stop her."

Was the cry from Churchill on his backbench - he was seen as an alarmist, that was until 1935, when his German rearmament warning came true.

Faith was gradually lost in Chamberlin and in 1939, Churchill was seen as the man who had the guts to face up to the Nazi threat, the rest as they say is history.

Sticking to what you believe is a high-risk strategy, which is the very reason he had gone into political wilderness, being very wrong on some high-profile failures such as the Gallipoli campaign and his empirical attitude to handling countries like India and Ireland.

Most politicians do as much as possible to avoid being on the losing side of a cause, carefully changing their views for personal benefit, but not Churchill, who for all his faults, had a certain integrity to debate to the death on what he truly believed.

When he was provided correct on Germany he came off as a prophetic genius, building a level of credibility that is priceless.

Churchill the tryer

Churchill was best known as a politician, but he was also a journalist, writer and in his spare time had interests in masonry and painting.

Basically, he was a tryer – unafraid to explore new interests and pursuits without fear of being no good, an early exemplar of self-improvement before it was even a movement.

His political career wasn’t the smoothest either and he has a varied history of contesting and losing seats in various elections.

The biggest defeat was being voted out of power after winning the war in July 1945.

Some would have been bitter at such an outcome and when someone suggested to Churchill the electorate had shown ingratitude towards him, Churchill, recognising a Britain fatigued by war and looking to the future, gave a graceful response,

“I wouldn’t call it that. They have had a very hard time”

As a man who was nearly 71, many would take this as a sign now was the time to retire.

Except, at the next election in October 1951 the Conservatives came back into power and he ran as Prime Minister until ill health in 1955 made him retire from the position.

Many put a negative view on Churchill today, because they apply a modern lens, but whatever your views no one can deny his uniqueness – an exceptional stamina, drive and charisma, with abilities harden by numerous failures.

With a long prolific career, you could ask what is Churchills greatest achievement?

Personally, I think the biggest victory was over himself.

He never let failure define his mindset – an inner confidence, where he did not dwell on short comings or define his character.

To steal the great man’s words, he did not flag or fail and he never surrendered

Imagine how different history would have been if we didn’t have this great man.

I love to hear your feedback, please do contact me on Twitter to let me know what you think of today’s article.

Until next time,