A Lesson From TR & Taft on Pursuing a Life You Like

The founders of the hit survival game Rust and The Stanley Parable offer lessons on how to live your life in a way that’s fulfilling. They have had wildly differing lives, but both maintain key priorities: freedom and creativity are two things they can’t find anywhere else.

“Riding for the disabled lesson plans” is a blog post written by two of the most successful people in history. They talk about how they pursued their life passions and what that taught them.

theodore roosevelt and william howard taft colorized photo.

I’m now working on a quest to read every president’s biography. The majority of the men seem to have been relieved to leave the office at the end of their tenure. It’s a demanding job in which the president’s opponents, and sometimes his own party, mercilessly criticize him. Even the president’s greatest achievements — the Louisiana Purchase, the Emancipation Proclamation, and the New Deal, to mention a few — were hated by the era’s partisans. It’s a difficult job. 

Theodore Roosevelt, on the other hand, adored it. He loved almost every element of his profession and considered his time at the White House to be the most rewarding of his life. He was still bursting with vitality and excitement for politics towards the conclusion of his 7.5 years in office, rather than looking decrepit and worn out like all presidents before and after. Roosevelt, more than any other president before him, was uniquely qualified for the role. 

He might have run for a third term, but following the 1904 election, he promised to allow someone else a chance at the presidency. Roosevelt was clearly a man of his word, unlike other leaders who have broken similar commitments. Of course, having a protégé to take over after him helped; he had been grooming William Howard Taft to follow in his footsteps for a long time. 

So on March 4, 1909, when Taft took the oath of office, Theodore stood to the side. He’d have a drastically different experience as the nation’s leader, in what turned out to be a great example of someone who was completely unfit for the post. 

william howard taft portrait as president.

President of the United States: William Howard Taft

It’s the bathtub tale that everyone knows about Taft, or “Will” to his friends and family. According to legend, the country’s most powerful ruler allegedly became stranded in a White House bathtub. The truth is that Taft was fully aware of his size, ultimately weighing in at well over 300 pounds, and had extra-large baths fitted when he moved in. So forget about that narrative and learn a few facts about the real Taft, the genial man whom Roosevelt adored and trusted. 

William Taft was a lovely creature even as a youngster. “It was difficult for anybody to be around him without adoring him,” stated Horace, the younger brother. He was always popular, but not in a charismatic sense, but rather in a warm, huggable one. Will despised argument and criticism, adored serious contemplation, and moved slowly but astonishingly deliberately. Taft went into law, which appeared to be a good fit with his personality (courtrooms aren’t nearly as dramatic as they are on TV, and this was particularly true a century ago). 

After receiving his first local judgeship in his late twenties, Taft set some lofty goals for himself. He aspired to be a Supreme Court judge, namely the Chief Justice. His inherent predisposition for pleasant interactions, calculated choices, and an intellectual existence made him an ideal candidate for the position of judge. He preferred a day on the bench utilizing his intellect followed by a peaceful evening at home in his library than rubbing shoulders with other politicians and fighting party leaders in the court of public opinion. 


William Taft accomplished an excellent job as a judge, ultimately rising to the position of federal judge. “No one on the circuit was more well known or more liked than Taft,” writes Doris Kearns Goodwin in Bully Pulpit. He was a happy guy on his way to being nominated to the Supreme Court. 

Will, on the other hand, married Nellie, a very ambitious lady who aspired to be President. The Supreme Court was wonderful, but it wasn’t the most prominent or exalted post in the country — it wasn’t the pinnacle of American success. Only one position could fulfill that ambition: President of the United States. 

When President William McKinley offered Taft the governorship of the Philippines in 1901, he accepted because he loved his wife and had an evident vulnerability when it came to being excessively influenced by people around him. Rather than remaining on the bench, it would be a better stepping stone to political development. 

However, McKinley was killed not long after. Will’s close friend Theodore Roosevelt was elected president, knowing that Taft’s ultimate goal was the Supreme Court. When a vacancy on the Supreme Court arose in 1902, Roosevelt offered Taft the position. It was all his to take. 

The huge man declined, arguing that his present job as governor of the Philippines was not yet complete. However, Nellie’s effect on the choice to hold out for something different is undeniable. She encouraged him to pursue better and higher positions throughout his career. As a result, when President Roosevelt asked Taft to be his Secretary of War, he accepted, moving up the political ladder and becoming, in Roosevelt’s words, “my counsellor and advisor in all the important matters that come up.” 

Aside from Nellie’s influence, Roosevelt finally pushed Will to follow in his footsteps to the White House and work as his steward. However, Theodore said that “the equation of the individual himself” must be the most important consideration while determining what to accomplish with one’s life. 

Regardless of such sound counsel, a submissive Taft didn’t want to disappoint anybody, so he rode Roosevelt’s popularity to victory in the 1908 presidential election. Despite the fact that Nellie was “finally completely at ease,” Taft despised the work from the outset. Goodwin argues that “within hours of his electoral victory, he was already distressed that his personality was ill-suited to his new post.” 

William Howard Taft had a mediocre four years in office. Unfortunately, Nellie had a terrible stroke only ten weeks into her husband’s presidency, putting her in a wheelchair for the rest of his reign. Taft was much more depressed about his work without his loving wife at his side. Roosevelt emerged from the ashes as a third-party candidate, finishing in second place behind Woodrow Wilson, after being dissatisfied by his friend’s performance as President (saying of him, “he means well, but he means good feebly”). Taft finished third and returned to Ohio, relieved to have put the worst years of his life behind him. In public recollection, the only thing that came out of it was the awful bathtub rumor.  


When Chief Justice Edward White died in 1921, Will finally had his opportunity to realize his goal. Warren Harding, a fellow Ohio Republican, gave Taft the post, knowing it had been his longtime dream. “This is the best day of my life,” Will declared on the day he was sworn in. It wasn’t the most prominent position in the country, but it was the one that William Howard Taft was most equipped for. Until his death in 1930, he cherished every moment of it. 

william howard taft portrait as chief justice of the supreme court.

Chief Justice of the United States, William Howard Taft. In contrast to the image above, notice how happy he seems.

When I read about Taft’s life and career, I couldn’t help but feel sorry for him. He might have spent twenty years doing what he liked instead of being forced into something he knew he wouldn’t enjoy. You may blame Nellie and Theodore for pushing the person too hard, but they weren’t trying to harm him. Taft had mutually and truly love and caring connections with each of them. 

Rather, this is a typical example of someone at the highest levels of leadership playing the “should” game. “I adore Theodore and want to protect his legacy; I should run for president,” I envision Taft saying, as well as “My wife is my rock and I want her to be happy; I should run for president.” The emotional pull of status was probably also at play; when he saw the brass ring hanging in front of him, he felt compelled to take it – that he was obliged to take it. He put off his own pleasure, his own satisfaction, for decades in this way. This sentiment is echoed by Goodwin: 

Taft struggled to turn [his] intuitive emotional intelligence inward to discover his own aspirations and apply that information to manage his life and career appropriately, since he was afflicted by procrastination and uncertainty. 

Are you able to relate? 

Your career is the obvious corollary. Is social media, family, friends, or society pressuring you to live a life you don’t want? 

Although entrepreneurship looks appealing on paper, you may prefer the less stressful, check-in/check-out aspect of your 9-5 job. 

Going to college and working in an office may seem to be the right option for you, but you may choose to attend a technical school and acquire a blue collar skill.

You may feel compelled to keep climbing the corporate ladder, but is transferring away from fieldwork and into a more management role really appropriate to your skills and desires?

A guy should pursue the things he actually enjoys outside of his work life as well: hobbies, books (and other content/media), leisure and fitness, and so on. 

Just because artisan beer is all the rage on Instagram doesn’t mean you can’t appreciate the cheap stuff. Just because your book group prefers Greek classics doesn’t mean you can’t read as many Jack Reacher books as you want. Just because every other millennial worships at the altar of international adventure travel, doesn’t mean you can’t be a homebody who loves regional road trips just as much. 


Don’t feel compelled to pursue the job, hobby, or concept that someone or something else has deemed the ultimate ideal. 

Spend time getting to know your own temperament and interests rather than chasing after what looks good or seems to be gratifying. Find strategies to seek the Good that are in line with your natural abilities and interests. Rather than self-flagellating discipline, live a life inspired by natural motivation. Get rid of your Taftian anxieties and totally accept and own what you adore.  

“Become who you are,” Nietzsche remarked. 



group riding lesson ideas” is a post by TR & Taft that offers life lessons on what it means to pursue a life you like. The article includes 7 tips for living a happy and fulfilling life.

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