Podcast #544: The Audacious Life of Winston Churchill

When we seek an example of great leadership, one man who often comes to mind is Winston Churchill — the iconic, visionary prime minister, who guided his country through war and stood firmly for his beliefs and impervious to his critics. But how did Winston become the legendary British Bulldog?

My guest today seeks to answer that question in his biography, Churchill: Walking with Destiny. His name is Andrew Roberts, he’s a journalist and historian, and we begin our conversation discussing why he thought another Churchill biography was needed. We then shift to the life of Churchill, beginning with a childhood in which young Winston often felt neglected. Andrew then discusses Churchill’s military career, why Winston was so eager to see action on the frontlines, and how he parlayed those experiences into becoming the world’s highest paid journalist by his mid-twenties. Andrew then explains how Churchill also became one of the 20th century’s great historians and how his appreciation of history and sentimental outlook colored his worldview and shaped his leadership. We also discuss why Churchill was one of the few leaders to foresee the threat that Hitler posed. We end our conversation discussing whether some of the current criticisms of Churchill, such as the allegation that he masterminded genocide in India, really hold weight.

Show Highlights

  • Why write yet another bio of Winston Churchill?
  • What was Churchill’s childhood like? How did it influence his later leadership?
  • Why did Churchill feel he was destined for greatness?
  • Winston’s military career, and his desire to see action
  • His early success as a journalist and his career as a writer
  • Churchill’s love of history and how it led to his success as a leader
  • His unconventional “religious” views 
  • His blunders while in charge of the Royal Navy 
  • Churchill’s wilderness years 
  • How was Churchill so stoic in the midst of criticism?
  • Churchill’s relationship with his wife Clementine 
  • Winston as a father 
  • What happened with Churchill met Theodore Roosevelt?
  • Churchill’s emotions, sentimentalism, and Romanticism
  • Roberts’ take on the modern criticisms of Winston Churchill 
  • Was Churchill born a great leader? Or did he fashion himself as one?
  • What are the leadership lessons we can take from Churchill?

Resources/People/Articles Mentioned in Podcast

Connect With Andrew

Andrew’s website

Andrew on Twitter

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