What would Churchill tell us millennials? 

The end of the month marks 55 years since Winston Churchill’s death. With an estimated 10,000 books on the great man, one clearly needs to be careful in adding yet more layers of legend or biography.

But this reservoir is too good not to tap, especially for young people that can learn practical lessons from someone who, at twenty-six, “had done enough to fill several lives”.[1]

Far from existing only for his time “at the very gates of destiny”, in the eulogising words of Robert Menzies, millennials can draw from Churchill in everyday terms – from persisting in the face of immense setback to targeting one’s best efforts, getting married and thinking hard about the quality of the ideas we advocate for.

Conserve your energy

Ryan Holiday’s recent bestseller Stillness is the Key maps how the greats of history – from Seneca to Mill – mastered their craft. He notes the key factor Churchill placed his success on – a conservation of energy. “Never stand up when you can sit down,” Churchill said, “and never sit down when you can lie down.”[2]

According to historian Paul Johnson, Churchill implored people “to waste no energy on grudges, duplicity or infighting.”[3] He also showed us to aim high, notes Johnson, never allow mistakes or criticism to get you down, and to make room for joy.[4]

Stay active

Many people will see Churchill as a physically ballooned figure. But as a young man he threw himself into vigorous exercise and, after a few attempts, active service. He eventually became the only British prime minister, in the words of Boris Johnson, with the distinction of being “shot at on four continents”.[5] In 1899, far from moving slowly, one can imagine Churchill showing great agility in escaping the Boer War as a POW into Transvaal and Portuguese territory.

Aside from combat, in his later years, he was a mental locomotive. “Churchill’s psychological make-up meant that he had to work,” adds Boris, “he was incapable of idleness.” He sustained a Herculean work effort offset by meditative painting and brick laying.

Spend time alone

Such a grand public life tends to miss the years when, in the 1930s, Churchill spent a decade ‘in the wilderness’. He had enjoyed success as a young public intellectual with a stratospheric rise in politics. But his years of political exile were among the most painful. He noted that, while this time of solitude, deprivation and reflection was far from pleasant, it helped build the “psychic dynamite” that all good leaders are made of.[6]

One need not experience political exile to understand this lesson. Spending time alone enables reflection, resilience and growth. “If, as a young man, you don’t feel ready for interdependence,” notes Steve Biddulph in The New Manhood, “then don’t start. It’s better to spend a few years growing up, fending for yourself, travelling unaccompanied; being really, really lonely – and discovering that you don’t die from it.”[7]

Get hitched

As good as solitude is, however, Churchill was eager as a young man to partner up and get married. “After two failed proposals,” writes Michael Shelden in The Young Titan, “he was beginning to have his doubts.”[8]

Today many young people have unprecedented opportunities to ‘opt out’ and ‘go their own way’. Without the burdens of responsibility, it’s an alluring lifestyle.

But the young Churchill, with classic persistence, never gave in. “Time and circumstance will work for me,” he wrote to friend Muriel Wilson in 1904.[9] And at 33 time did work for him, marrying his wife Clementine – an immense and profoundly positive influence on his life.

Get a routine

“He was totally organized,” notes one of Churchill’s research assistants, “almost like a clock. His routine was absolutely dictatorial. He set himself a ruthless timetable every day and would get very agitated, even cross, if it was broken.”

Being good takes practice

Millennials live in a time of overnight success measured in likes, clicks and followers. But many of us realise that true success takes place away from the glean of social media.

Churchill was seen as a master orator. This skill didn’t come without great practice. “All day he might be heard boom away in his bedroom,” noted a close friend, “rehearsing his facts and flourishes to the accompaniment of resounding knocks on the furniture.”[10]

In not just speech but appearance everything was polished for effect and performance. “Everything had to be perfect, from the way he tugged at the lapel of his long frock coat,” notes Shelden, “to his manner of beating the air with a clenched fist.”[11]

Personality in politics

While Churchill’s leaps between political parties would alarm us today, he does offer a great example in independent thinking. “Nothing would be worse that that independent men should be snubbed out, and there should be only two opinions in England – the Government opinion and the Opposition opinion,” he told an audience in Liverpool in 1901. “The perpetually unanimous Cabinet disgusts me. I believe in personality.”[12]

This would, decades later, turn out to be much more than simple stubbornness – he had to convince Cabinet that taking on Hitler, and not striking a deal, was the best course of action. While speaking his mind wasn’t always helpful to his career, it was an inspiring early commitment to being an ‘independent man’ from which we can all draw.

Play the ball, not the person

Churchill was once asked in Cardiff if he hated his enemies. His answer was telling:

“I recollect what an American solider once said when he was asked: “When you aim your rifle at the men on the other side, do you hate them?”… His reply was: “No, I don’t fire at anybody. I simply fire at the line of the battle.” Really, that is what I have been doing all my life.”[13]

Live well, but don’t neglect the basics

Enough to live on, said Churchill, is the prime necessity of life. “Every man of us should think of nothing but that till it’s achieved,” he said. “Afterwards one can do what one likes – please keep that in front of you as the object of your life.”[14]

What was ‘doing what one liked’ for Churchill? Aside from hard work it was staying at the best hotels, eating oysters and knocking back champagne. Yet this was the result, and not in spite of, dogged hard work.

Be aware of your limitations

We often think that Churchill could do anything – slot into any role and do any job.  This wasn’t always the case. In 1905, for example, while making his upward mark in government, he turned down a coveted role as Assistant Treasurer in favour of a less impressive Undersecretary to the Colonial Office. While no doubt thinking hard about his image as more of a statesman from a swashbuckling adventurer, it at least suggests some alignment with his experiences and capabilities at the time.

Quality not quantity

Finally, Churchill advised young people to not bury themselves in mountains of paper or irrelevant information. The quality of their inputs, he said, mattered more.

Here it’s hard not to think about the shiny issues that many young people pick up and advocate for today, with very little thought on why things are the way they are or, at minimum, how a free society and market economy works.

“I gained a lot by not overworking my brain when I was young,” notes Churchill. “It is a mistake to read too many good books when quite young… Young people should be careful in their reading, as old people eating their food. They should not eat too much. They should chew it well.”[15]


[1] Michael Shelden, Young Titan: The Making of Winston Churchill, Simon & Schuster, Sydney, 2013, 25.

[2] Ryan Holiday, Stillness is the Key, Profile Books, Coydon, United Kingdom, 2019, 170.

[3] Ibid, 170-171.

[4] Ibid.

[5] Boris Johnson, The Churchill Factor: How One Man Made History, Kindle Version.

[6] Holiday, 179.

[7] Steve Biddulph, The New Manhood, Simon & Schuster, Sydney, 2019, 45.

[8] Shelden, 104.

[9] Ibid, 106.

[10] 28.

[11] 28.

[12] 91.

[13] 101.

[14]  114.

[15] Thomas E Ricks, Churchill and Orwell: The Fight For Freedom, Penguin Press, New York, 2017, 10.

Image source: The Great Courses

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