Theodore “Teddy” Roosevelt – Leadership & Life Lessons In The Spotlight
Theodore “Teddy” Roosevelt stands as one of the greatest leaders in American history. Teddy was the 26th President of the United States and a leading force of the Progressive Era. He was also an author, explorer, soldier, naturalist, and reformer. Furthermore, Theodore Roosevelt is universally recognized as a consequential — indeed transformational — leader. Here are some leadership & life lessons that you can learn from Theodore Roosevelt.
Few American presidents have earned a legacy quite as prolific and inspiring as that of Theodore “Teddy” Roosevelt.
His bold, charismatic leadership style and his aggressive attitude toward government action resulted in an almost mythic persona that persists to this day. He won the Nobel Prize for Peace in 1906 for mediating an end to the Russo-Japanese War (1904–05), and he secured the route and began construction of the Panama Canal (1904–14). He also further developed and expanded the relationship between the press and the Oval Office by giving them more access via interviews and photo opportunities.
Theodore Roosevelt is widely regarded as the first modern President of the United States.
He made the President the center of American politics. Roosevelt did this through the force of his personality and through aggressive executive action. He believed that as President, he had a unique relationship with and responsibility to the people, and therefore wanted to challenge prevailing notions of limited government and individualism; government, he maintained, should serve as an agent of reform for the people.
Although sickly as a child, suffering debilitating asthma, Theodore Roosevelt lived a life worth admiring.
He read thousands of books, wrote a bunch of books himself, served in various levels of government (including, of course, the role of President of the United States), fought in wars, and nurtured a lifelong love of nature. And that’s just a taste of what he accomplished! His high-spirited personality, broad range of interests, and “cowboy” persona made him world-famous.
But what leadership & life lessons have we learned from Teddy? If you look deeper into what he did during his life, you’d see a handful of valuable things that you can apply to your everyday life.
You may think it’s almost hard to comprehend how much Theodore Roosevelt has accomplished in his life. To summarize, I will distill below five lessons from Teddy Roosevelt’s larger-than-life leadership.
Lesson #1: Leadership Is Action
Whether it was the construction of the Panama Canal, taking on J.P. Morgan, or any number of other memorable challenges, Teddy Roosevelt took the risks of action, over the greater (if sometimes less evident) risks of inaction or delay.
Theodore Roosevelt believed in taking initiative and decisive action, tenets that were likely influenced by his study of military history.
He understood the value of taking the initiative and tended to complete or delegate tasks quickly. This did not mean imprudence; Roosevelt still applied a methodical approach to decision-making, thanks to his military and legislative background. In one of his most popular speeches, known as the Man in the Arena, Roosevelt said: “The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood.”
Whether it was in the boxing ring, on the frontier chasing a grizzly, or in thick of battle Roosevelt leaned into action.
Early on in his life, his energy and self-confidence led him to make many mistakes. But over time, he learned to temper his words and his emotions. Still, such self-control never stilled his fearlessness. Even more, his fearlessness was not just his willingness to stand in the face of danger. He was equally willing to admit his mistakes and learn from them.
It seemed few things in life bothered Teddy Roosevelt as much as laziness. He maximized his time and he expected you to do the same.
Why It’s uncommon: We’ve built a shrine to busy-ness in today’s world. Nothing seems to please people more than saying that they’re too busy to do something. Any time you bring up a goal or pursuit, you’ll get a parade of peers eager to explain why they wish they had the time to do that. Think you don’t have the time? In Roosevelt’s day, the typical day lasted 24 hours. As far as I know, days today still clock in at 24 hours. You have the same amount of time that he did — what are you going to do with yours?
Leaders who want to make a change must not be afraid to act — action is what leads to growth. For Roosevelt, leading from the front was key.
During his time as Police Commissioner of the New York Police Department, he made the time to go into the field to check that officers were on duty during their beats. As President, he was the first to travel overseas during his tenure, a mark of how he thought America should play a larger role in world affairs. Theodore Roosevelt was not content to lead from behind a desk; he wanted to be out there to truly understand the issues that he had to solve as a leader.
Lesson #2: Stick to Your Guns
Theodore Roosevelt was one of the first American statesman who remained politically active even after he left office. He was driven by his belief in the progressive movement and his desire to effect change in his country. When he became disillusioned with Taft’s presidency, he was moved to re-enter politics in order to fight for what he believed in.
Teddy Roosevelt’s success hinged in large part upon his passion for his work.
The key to success is allowing passion to run through everything that you start. Roosevelt’s passion was rooted in his values. Many of his executive decisions revolved around the values of fairness, equal opportunity, and economic growth. With such lofty ideals in mind, he was able to enact major changes in the government’s relationship to big business, the role of the president as a whole, environmental conservation, and foreign affairs.
Compromise undermines our values. It isn’t about listening and learning from others, it’s about giving in.
When you make compromises or say yes to projects against your better judgment your values suffer. Imagining you are doing it to please someone or out of kindness or for a quieter life doesn’t change this. Being open to new ideas and being able to take advice is a mark of humility and flexibility. But doing whatever anyone else wants of you or saying yes to everything that comes along is simply weak and ill-considered.
Becoming a leader of strong character comes down to living true to your core beliefs and values.
These values help you determine what’s right and wrong, and are key to making wise decisions. Since our success is a composition of good decisions, having the character to lead based on core beliefs and values cannot be overemphasized. True character is not something for which you can take a class. It is who you are when people are looking, but more especially when they are not. Being congruent means you are the same person regardless of the circumstances or who is watching.
Values run deeper and are more important to a leader’s effectiveness than any other single factor.
It’s crucial for a leader to act on core values, not convenient ones, and leaders who are value-driven will never be shaken. No matter what happens in their lives, they can be confident that the right principles have shaped their values and have guided their decisions. That type of confidence provides emotional and spiritual stability.
Lesson #3: Keep Your Word
Today, commitments are violated willy-nilly as they become inconvenient or undesirable. This has always been even more the case among politicians. Theodore Roosevelt was notable in striving to meet commitments. He would meet commitments to his children to play, even if it meant that meetings of state would have to end.
Teddy Roosevelt was always a man of his word. He would go out of his way time and time again to meet any commitment he made.
This may seem incredible in this day and age that a politician always did exactly what he said he was going to do, but this is the kind of leader Teddy Roosevelt was. He applied this to all areas of his life. When he promised not to seek re-election, he acted the same way. He was given numerous opportunities to stand for President again, and by all accounts he would have won. But he made the promise and refused to go back on it. He understood that without trust, there was nothing.
How effective are you at keeping the promises and commitments you make — those commitments you make to others and those commitments you make to yourself?
The cost you pay for not keeping your promises may not seem like much at the time, but the true cost is a cumulative cost, a cost that, over time, will significantly erode the trust others place in you, your personal integrity, your self-esteem, your self-confidence and your self-respect. A high cost indeed. When you realize how important your integrity really is, you will stop making casual promises just to get someone off your back. You won’t sell your self-esteem for a little bit of momentary approval. You won’t make promises you don’t intend to keep. You will make fewer promises, and you will do whatever it takes to keep them.
Making a promise and carrying it out is, indeed, a measure of character.
Anyone who makes a promise, gives their word they will do something, or pledges their support and yet does not live up to the deal, or lies to you, has broken a sacred trust. Betrayal is the most undesirable quality of a leader and often the very reason so many leaders fail. A quick reading of Dante’s Inferno is a literature classic that demonstrates the depths of betrayal in a hard-hitting fashion. The lessons for leaders is simple. Make a promise; make it your new priority.
We must say what we mean and do what we say. There can be no daylight between the two.
Don’t over-promise and under-deliver. Be upfront and honest with your team and refrain from making promises that you know you cannot deliver on — it will only hurt morale and cause your team to question your motives. Knowing that you can trust your team to get the job done is essential. However, they will not trust you unless they know you are willing to follow through on your commitments and have their back. Mutual trust plays a large role in shaping an organizational culture that will thrive.
Lesson #4: Never Stop Learning
Leaders are Learners. From youth, Theodore Roosevelt was a voracious reader: “Reading is a disease with me.” His curiosity, his ceaseless learning, never abated. His example, combining the life of ideas and the life of action, was central to his project of self-creation as a leader.
Teddy Roosevelt is known as one of the most well-read presidents.
He once said he had read tens of thousands of books during his lifetime, and according to sources close to him, he would read up to 3 books every day. His love for reading began in his early years, when his asthma confined him to bed. This developed into a lifelong passion for knowledge, aided by Roosevelt’s ability to speed read and retain large amounts of information. Sometimes learning about something completely unrelated to your field can yield inspiration and insight on the issues you’re facing.
As president, Theodore Roosevelt was constantly pushing the limits of his individual growth.
He would have argued that true leaders are made, not born. He understood that the path to effective leadership was an ongoing process, one which was dependent in large part on self-reflection and self-improvement. Individuals who occupy positions of leadership must avoid complacency, he insisted. Satisfaction with having met particular goals is a good sign, but leaders should strive to continually develop themselves in productive, meaningful ways so that they can effectively serve others and gain their trust.
Often the adage is affirmed that leaders are born, not made. Theodore Roosevelt, one of America’s finest leaders, countermands that claim.
He was not born a leader, but a sickly child who had to literally and figuratively fight his way into adulthood. He made many mistakes and many enemies along the way, and yet he learned in every operation of life how to be a better leader. In this way, his life reminds us that leadership is a skill that can be learned, improved, and grown — especially through suffering — as diligent leaders seek to improve their leadership by admitting their weaknesses and improving their efforts.
Not all readers are leaders, but all leaders are readers. There’s a direct correlation between the amount of books you read and the quality of your leadership.
Most professionals tend to reach a plateau when it comes to learning. And we’re all busy, learning new things can easily be relegated to the backburner when it comes to priorities. However, it’s worth the effort because leaders who have a continuous learning mindset develop stronger leadership skills than their peers. To learn is to grow, to evolve, to master. If you’re not continually growing and using it, you will lose it. Yes, your experience does matters, but in the long run, it’s your curiosity, your thirst for knowledge and understanding that will make you an outstanding leader.
Lesson #5: Don't Take It Easy
Self-discipline is really important in order to succeed. Without it, we will be lazy, we will procrastinate. It’s one of the most important ingredients of success as it allows us to stick to our schedule, our plan. It allows us to focus on the goal, the end game, and that’s what going to make us succeed in the future.
Theodore Roosevelt always preached about the virtues of the “strenuous life”.
And the best lesson from this is that your happiness and the quality of your life is in your hands. It’s your choice. It’s based on your decisions. You control your destiny, in a way. Sure, things happen along the way. But more often than not, your unhappiness comes from the effects of your own decision-making and inaction. The beauty of this is that you now have the control to become happier and more successful. But you have to take that chance and put in the work.
Theodore Roosevelt was a warrior. His virtues and shortcomings are best evaluated with an eye toward the world in which he lived.
Death was a constant companion. The consequences of the barbarism of the Civil War was very much in evidence in every part of American life. In this world, courage was paramount. Physical courage was prized. Moral courage, perhaps even more rare, was necessary for enduring service. We’ve glorified success in this society so much that everyone only focuses on the “overnight” nature of success. It’s a romantic idea that simply doesn’t occur in real life. Overnight success only comes from work. Nobody hands you success and money over a good idea. They reward you for rolling up your sleeves and building something.
Don’t be afraid to speak out whenever you have any ideas. Don’t be scared of failure.
Always remember the simple fact that if you never try, you will never know what the result might be. Yes, there is a possibility that you might fail after you try, but you can rest easy knowing that at least you tried. Yes, failure is hard to accept, it has always been. But failure is also an opportunity to grow. It’s part of the path towards success. Every successful person faced failure multiple times before in their lives. Why did they finally succeed? Because they dared to try. They dared to take action to make their dreams a reality. They are never afraid of trying and taking action in their path to success.
Courage is a trait that seems to be in short supply these days, in leadership and elsewhere.
People are looking for the kind of bold confident leaders we’ve seen throughout history — leaders who spoke up and stepped forward, who took the risks of true leadership when radical change was required. Let people know they can count on you. Accountability means you take on responsibility, deliver on commitments, and own up to your own mistakes and limits. When you hold yourself accountable, you model that behavior to those around you and help establish a culture where it’s the norm. Be bold, be that guy!
Throughout his life, Theodore Roosevelt stood by his beliefs and was moved to action to support them. What do you believe in and want to achieve as a leader? The strength of your belief and your willingness to fight for them can inspire others to join you in the journey to success.
Be willing to step out of the norm and take risks in order to achieve your goals!
The message Theodore Roosevelt is trying to send is to grab every opportunity you have in your life, even if you aren’t prepared. If you don’t seize the opportunity, you may regret in the future. Besides, do you see the positive mindset in the quote? “Certainly I can” You’ve just got to believe in yourself!
In short, Theodore Roosevelt believed that happiness and success is a product of your actions and effort.
Take the time, be patient, and work hard — you’ll see the results you’ve always wanted. Theodore Roosevelt’s life and presidency validated my belief that collective success is a consequence of individual betterment. By embracing a growth mindset and multifaceted interests, while communicating consistently and authentically with those we serve, we can emulate Roosevelt’s leadership prowess in our daily lives.
Great Leaders demonstrate an ability to create a vision that can be embraced by the masses to the benefit of the masses.
They recruit great thought leaders to share opinions and work towards a common goal. They support, encourage and recognize the important contribution of all the stakeholders and make them feel they are critical to the agenda’s success. Most importantly, they promote others for the accomplishments when successful, and take personal accountability when they do not.
Becoming a great leader is up to you — nobody is going to give it to you.
While Theodore Roosevelt has made its mark on history, consider the ways his leadership still teaches us today. Remember: You must become the change you want to see in your team or organization. Leadership is about taking the leid. To find the way (from Old Norse) is being the leadership role model you want to see in everyone else.
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