3 Lessons Bestselling Teddy Roosevelt, Winston Churchill, and Steve Jobs Biographies Can Teach You About Life and Leadership

3 Lessons Bestselling Teddy Roosevelt, Winston Churchill, and Steve Jobs Biographies Can Teach You About Life and Leadership

If you’re a history geek, it’s hard to beat curling up with a good biography. Award-winning writers Doris Kearns Goodwin, Erik Larson, and Walter Isaacson didn't merely write definitive books about Teddy Roosevelt, Winston Churchill, and Steve Jobs, respectively – all teased out key lessons about these pioneering figures. Here are three key takeaways that you can apply today:

  • Teddy Roosevelt’s Relentless Drive7

Though dismissed by Teddy Roosevelt as “a muckraking” magazine, McClure’s was in fact one of the finest literary publications ever, featuring award-worthy investigative reporting in the late 1800s and early 1900s (see Stephanie Gorton’s excellent book Citizen Reporters for the full scoop). Contributing writer Ray Stannard Baker had direct access to the White House and, once Roosevelt ascended to the presidency in September 1901 after the assassination of William McKinley, became an even more frequent visitor.

Many members of the press (at least, those who supported Teddy) were captivated by Roosevelt’s charismatic presence and booming laugh, which never failed to dominate every room he was in. Yet Baker tried to convey a more objective picture of the 26th president to his readership. In The Bully Pulpit, Doris Kearns Goodwin shares Baker’s contention that while most people fail to tap “vast stores of hidden energies,” the former colonel of the Rough Riders succeeded through “the simple device of self-control and self-discipline, of using every power he possesses to its utmost limit – a dazzling, even appalling spectacle of a human engine driven at full speed.”

When serving in the New York Legislature earlier in his political career, Roosevelt took on the corrupt Tammany Hall apparatus that ruled the Big Apple through a combination of intimidation, corruption, and nepotism. His brave stand was so dangerous that Teddy once unscrewed a table leg to use as a cudgel if he was attacked by his opponents whose political careers were at risk. He was similarly vigorous in his personal life, interspersing writing hundreds of letters a year and welcoming dozens of visitors into his office at all hours of the day and night with tennis matches and hikes on which he was determined to go over or through obstacles. Roosevelt also a keen boxer, once knocking down the head of the US Forest Service as they sparred in front of his desk. As Doris Kearns Goodwin’s vivid portrayal demonstrates, there has never been a more driven, self-motivated, and determined person in the Oval Office than Teddy.  

  • Winston Churchill’s Indomitable Will

As the king of microcosm history, Erik Larson’s trademark has been to focus on lesser-known protagonists – a meteorologist in Isaac’s Storm, the family of a US Ambassador In the Garden of Beasts, and a serial killer in The Devil in the White City (which has been optioned by Leonardo DiCaprio’s production company for a TV adaptation). But for his latest book, The New York Times bestseller The Splendid and the Vile, Larson turned his considerable research and writing talents to one of the most widely documented leaders in history – Winston Churchill.

In true Larson style, he zeroes in on a limited timeframe – namely, when the future of democracy hung in the balance as Britain stood alone while the Nazis swept across Europe with their seemingly unstoppable blitzkrieg (aka lighting war) strategy. Pressed by members of his own party and his Labour and Liberal Party colleagues in the coalition government to negotiate for peace terms, Churchill knew that Hitler’s hunger for power and domination would never be satiated by any treaty. After all, look at what had happened to countries like Czechoslovakia and Poland – they’d been overrun by the forces of fascism.

This story has been told before, most notably by John Lukacs in Five Days in London and through Gary Oldman’s Oscar-winning portrayal of Churchill in Darkest Hour. But in his six years of fact-finding, Larson managed to unearth some real gems about the character of the prime minister who stood firm in the face of tyranny. “He raised the specter of Britain, too, succumbing to Hitler’s influence and warned that a new and pro-German government might then replace his own,” Larson wrote.

Then he quoted Churchill directly as saying, “If we go down you may have a United States of Europe under the Nazi command far more numerous, far stronger, far better armed than the New World.” In the end, it was Sir Winston’s unshakeable courage – which Churchill once said was the most important virtue because it guaranteed all the others – that not only kept Britain from giving in but also galvanized the Commonwealth into standing united until Germany foolishly declared war on the US after Japanese bombers destroyed most of Pearl Harbor.

  • Steve Jobs’s Recruitment of A Players

Former Apple marketing executive, bestselling author, and host of the Remarkable People podcast, Guy Kawasaki, once remarked that B players hire C players, C players hire D players, and so on because incompetent and insecure leaders don’t ever want to be challenged or outshone, and so surround themselves with mediocrity.

Though he could be headstrong and had a tendency to oversimplify his assessment of people by dividing them into “gods or clods,” Apple co-founder Steve Jobs took the opposite approach according to official biographer Walter Isaacson. While the company was in its infancy, Jobs had a bad habit of forcefully taking over projects at Apple and dismissing anyone who he thought was slowing him down. But once he had matured emotionally, Jobs came to recognize that while he was undoubtedly a visionary and an A player, he also couldn’t do everything at Apple.

As the business grew in his second stint at the company’s helm, so did Jobs’s need to delegate. He would only do so to people that he fully trusted and considered exceptional. This applied to the technical prowess of his co-founder Steve Wozniak (aka “Woz”) in the early days, and later to the minimalist eye of Jony Ive – who was responsible for the iconic click wheel iPod and so many other classic Apple silhouettes – and Kawasaki’s marketing genius. Simply put, Jobs sought out the cream of the crop.

Explaining to Isaacson why he hired Ive, Jobs revealed, “If I had a spiritual partner at Apple, it's Jony. Jony and I think up most of the products together and then pull others in and say, 'Hey, what do you think about this?' He gets the picture as well as the most infinitesimal details about each product. And he understands that Apple is a product company. He's not just a designer. That's why he works directly for me. He has more operational power than anyone else at Apple except me.”