An idea (Churchill)

Winston Churchill wasn’t easy to work with.

He could be gruff, impulsive, and wildly stubborn.

He made major strategic missteps and was voted out of office twice.

He smoked cigars, stayed up too late, and rarely apologized for his style.

And yet—in the darkest hour of the 20th century, when Nazi Germany was sweeping across Europe—the world turned to Churchill.

Not because he was perfect.

But because he was clear, courageous, and committed to the cause when others wavered.

He didn’t try to be agreeable.

He tried to be useful.

And that made all the difference.

Here are five enduring leadership lessons from Winston Churchill, especially for those leading through uncertainty, fatigue, or overwhelming odds.

1. Clarity Is a Form of Courage

Say what needs to be said

Churchill didn’t sugarcoat reality.

He met fear head-on—not with fluff, but with language that gave people something to hold onto.

“I have nothing to offer but blood, toil, tears, and sweat.”

The Story: In his very first speech as Prime Minister, Churchill didn’t try to inspire with false hope. Instead, he named the cost and declared the mission: “Victory, however long and hard the road may be.”

His honesty didn’t crush morale; it galvanized it.

As a leader, we can be vulnerable and strong at the same time.

Vulnerability builds connection. Strength provides stability.

Do This Today: Don’t water down your message. Identify one place where you need to speak with clarity, not comfort.

Reflection Question: Am I using my words to soften the truth or strengthen those who must face it?

2. Defiance Can Be a Virtue

Grit is the combination of passion and perseverance.

Churchill was often alone in his convictions. Before WWII, many in Parliament favored appeasement. He stood nearly alone in warning against Hitler and was dismissed as an alarmist.

The Story: When bombs rained over London during the Blitz, Churchill refused to flee to the countryside. He walked the rubble. He visited victims. He stood in the street while air raid sirens howled.

“We shall not flag or fail. We shall go on to the end… we shall never surrender.”

His refusal to back down gave others the courage to rise up.

Do This Today: Name one principle you’ve been hesitant to stand for. Recommit to it (perhaps even in a visible way).

Reflection Question: Am I avoiding resistance or embracing the responsibility that comes with conviction?

3. Humor Is a Leadership Weapon

Churchill wielded humor the way some wield a sword—not to wound, but to cut through tension, fear, and self-importance.

He didn’t use humor to avoid the seriousness of the moment. He used it to create emotional space where people could breathe, laugh, and regroup, even in the middle of war.

“A joke is a very serious thing.”

The Story: His wit became legendary. When a political rival said, “If you were my husband, I’d poison your tea,” Churchill replied: “If you were my wife, I’d drink it.”

It wasn’t just sharpness for show; it was timing, tone, and knowing his audience. During the Blitz, Churchill’s ability to make light of grim moments gave Londoners something Hitler’s bombs couldn’t destroy: spirit.

He once said,

“If you’re going through hell, keep going.”

And sometimes, the best way to keep going is to lighten the load, even just for a moment.

Humor, when used well, signals confidence.

It humanizes leaders.

It disarms cynicism.

And in the right moment, it can break tension faster than a strategy memo ever will.

Do This Today: Find a moment to bring a smile or laugh to your team—not as a distraction, but as a shared breath in the middle of the push.

Reflection Question: How do I use my presence to shift the emotional temperature of the room?

4. Rest Isn’t Laziness — It’s Strategic

Churchill famously took long baths and midday naps.

He’d work late into the night, then recharge during the day.

His rhythms were unconventional but intentional.

The Story: In the middle of wartime crisis, Churchill would sometimes take a two-hour break in the afternoon. When questioned, he replied:

“Nature has not intended mankind to work from eight in the morning until midnight without that refreshment of blessed oblivion which even if it only lasts twenty minutes, is sufficient to renew all the vital forces.”

He wasn’t lazy. He understood that sustained leadership requires strategic recovery.

Do This Today: Block 30 minutes this week to recharge—not as an indulgence, but as an investment in your clarity.

Reflection Question: Do I treat rest as weakness or as wisdom?

5. Big Moments Require a Big Voice

Churchill didn’t mumble. He declared. When the world felt small and scared, he made people feel large and capable again.

The Story: Churchill spoke to more than just Parliament; he spoke to history. He knew words shape will. His speeches didn’t just narrate the moment—they shaped it.

“To each, there comes in their lifetime a special moment when they are figuratively tapped on the shoulder and invited to do a very special thing. What a tragedy if that moment finds them unprepared or unqualified for that which could have been their finest hour.”

Do This Today: In your next meeting or conversation, speak with the weight the moment deserves. Every moment to practice clear communication is preparation for future moments that might matter even more.

Reflection Question: What is one specific way you can sharpen your communication?

The Churchill Leadership Speech Rehearsal

Churchill shaped history with his words.

Imagine you’re called to give a speech about a topic you care deeply about.

What would you say?
What stories and illustrations could you share?
What would you want people to feel?
What are one or two memorable one-liners you could include?
What would you ask people to go do?

Your voice matters, and words can move people.

Lead like Churchill: with clarity, courage, and commitment to the cause.

With you on the journey,
Cal

A question

Where do you need to show up in person, not just in position?

A quote and resource

"Laughter is an instant vacation."

—Milton Berle

The Mission

I am on a mission to help thousands of leaders gain clarity, courage, community, and consistency in their lives. Thank you for joining me on this journey!

I'm rooting for you,

Cal

➡️ When you're ready, I can help you gain more joy and deep clarity with my Core Values Mini Course. It has helped over 150 leaders live a truly intentional life. Join here 🎯

Intentional Letter: Churchill's Leadership