Theodore Roosevelt: Turning Weakness into Greatness

On The Franklin Planner Podcast, hosts George Wright III and John Harding are joined by Misty Howard to explore the life of Theodore Roosevelt and how he transformed personal weakness and overwhelming adversity into legendary greatness. From overcoming a debilitating childhood illness to enduring tragic loss and leading troops from the front lines in the Spanish-American War, Roosevelt’s journey illustrates how mindset, discipline, and intentional choices build true resilience and character.  
Howard breaks down key defining moments in Roosevelt’s life, including his transformational years in the Dakotas, his rise as a reform-minded leader fighting corruption in New York, and the square deal policies that defined his presidency. The conversation highlights Roosevelt’s philosophy of “The Strenuous Life”, lessons from the iconic “Man in the Arena” speech, and actionable Franklin Planner activities—such as separating what you can control from what you can only influence—to help you take control of your response, lean into your fears, and lead your life with purpose.

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Episode Timeline

00:00 – Introduction: Turning Weakness Into Greatness  
01:14 – Why Teddy Roosevelt’s Story Matters Today  
03:38 – Overcoming Childhood Illness Through Discipline  
07:44 – Planner Activity: Identifying What You Can vs. Cannot Control
09:10 – Tragic Loss and the Light That Went Out  
13:40 – Adjusting Goals in Seasons of Grief  
15:45 – The Dakota Years & Developing “The Strenuous Life” Philosophy  
20:25 – Leading from the Front: The Spanish-American War & Rough Riders  
25:05 – Values-Based Leadership: Fighting Corruption in Politics
29:35 – Stepping into the Presidency: Preparation Meets Opportunity
32:25 – Modern Presidency, Trust Busting, and Conservation  
35:10 – The Man in the Arena: Action Over Criticism  
39:20 – Final Thoughts & Challenge: Daring Greatly in Your Own Life  

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Episode Transcript

​George Wright III: Okay, welcome back to the Franklin Planner Podcast. My name is George Wright III, here with John Harding and Misty Howard. John, how are you today?

John Harding: I’m doing well, George, and so grateful to be here with all the listeners, you, and the famous Misty Howard.

George: Yeah, Misty it’s so great to have you back. We’re really excited today because we’re gonna be highlighting Theodore Roosevelt, and the idea and the principles of resilience in character and leadership, and so we’re really excited. And so for those of you listening wanna make sure that you subscribe to the podcast, don’t miss any episodes. We’ve got some great new topics coming up: The 10 Natural Laws from Hyrum Smith, as well as many other topics that you have been requesting, so we’re super excited.

A Very Significant Historical Figure

But today we’re gonna be talking about Theodore Roosevelt and the idea of turning weakness into greatness. And so we’re gonna do that through the highlight of Theodore Roosevelt. So Misty, maybe you could start us out by letting us know, why should this be important? Other than being a well-known historical figure, what about Theodore Roosevelt prompted us to highlight him today?

Big impact

Misty Howard: Well, I would say that nobody is gonna argue with you and say that Theodore Roosevelt was not a significant person. A very significant historical figure. I think about Mount Rushmore, and how you have people like George Washington, Thomas Jefferson, Abraham Lincoln, and then of course, we have Teddy Roosevelt. And that gives you an idea of the type of person that he was in that he had such a big impact, not just on the history of America but on the history of the world.

But that being said, he also has a very inspiring story. And that’s something, you know, on a more personal note. He lived a life that was… [Laughter] full of good deeds. It was full of tragedy and it also came with a lot of challenges. But that itself is the reason why he’s so worth studying, is because he overcame a lot to become someone who was great.

George: Yeah, and John, we try to curate these topics and these individuals that we focus on because there are some really timeless principles. So from your perspective, what are some of the reasons you felt this was important for us to do today?

John: Well, I love the story of Theodore Roosevelt. I think he could be one of the strongest figures in this series because his life illustrates, at least for me, this central theme related to leading your life, that each of us face. And Misty, thank you for being here. Thanks to the listeners. Thanks for the homework you’ve done on this.

“An excellent person to study”

But here’s the idea of Theodore Roosevelt and leading your life and just creating the life you want or dealing with what comes: We do not choose everything that happens to us, but we repeatedly face the choice of what we will do with what happens. And I just think he’s an excellent person to study, and that we can really learn something here. We can really learn something that hopefully can inspire us when we need it. And when we’re using our planner, when we’re using the mindset of taking charge of our life and in the midst of a lot of things we can’t control, I hope that that comes out. I just think he’s a really strong example we can look to to strengthen what we’re going through today.

Turning Weakness to Strength

George: Yes, because success leaves clues, and I think this is a great example of that. So maybe let’s jump right into it. Let’s start with his childhood, Misty. At the end of the day he’s a great example of really turning weakness to strength, and so what challenges did Roosevelt face as a child? Talk to us about a little bit of the backstory for Teddy Roosevelt.

Misty: His childhood really is key to understanding who he was and how he became so successful. Because, you see, Teddy Roosevelt was born into a family of great affluence. His father was a New York merchant—very wealthy, very successful—but he and his family are proof that having all the money in the world doesn’t [Laughter] safeguard you from challenges.

A sickly child

Because Teddy Roosevelt, despite now how we look back at him as this robust figure who loved being in nature and conquering the wild, he as a young boy was very sickly. He was very prone to illness. He was thin and frail. He had terrible asthma attacks, and I say bad—I mean, in the middle of the night, he’d wake up feeling like he was suffocating and just had throughout his whole childhood these terrible periods where he felt like he was going to die because he just couldn’t breathe. And of course, he was terribly nearsighted too, which is why he would wear his big glasses throughout his life.

A loving family

But those are just some of the physical ailments that he faced. But you see, his family, he did come from a very loving family. His father was a very admirable individual, somebody who was involved in a lot of charities and really represented to Theodore Roosevelt, like, the perfect manhood and who he should aspire to be. His father—very involved in his caretaking and would come in the middle of the night just to hold him, and was very compassionate as he was dealing with these challenges.

But his father, as a good dad, also saw fit to challenge Theodore and to call him to overcome his challenges. He actually said to him, “Theodore, you have the mind, but not the body. You must make your body. It is hard drudgery to make one’s body, but I know you will do it.” So in other words, he’s challenging him to begin a regimen of exercise that’s going to help him become healthy. And it’s not just a challenge, it’s a vote of confidence. He believes that he can do this.

A show of immense determination

And so Roosevelt actually ends up turning his bedroom into a gymnasium, and he begins this intense exercise regime that helps to, slowly over time, build his body and help him to overcome these physical challenges. And eventually, he does. By the time he’s a young man, he is, you know—he’s become a strapping young person that is quite healthy. And I think that shows us that he was somebody of immense determination.

George: Yeah, those are great examples of both leaning into your strengths and rather than focusing—I talk a lot in business with people when we say “don’t focus on the problem, focus on the solution”—but leaning into your strengths. And he obviously had a nice support structure as well and just made the decision to move forward. But I like that it’s really a great example, John, of what you said, which is not letting your circumstances kind of determine your direction, right, John?

“Engage the difficulty”

John: We could say, hey, he was a sickly boy, and who knows all the details, ’cause we know out of these great lessons. And he really was great. But we know it’s hard, and there’s a lot we don’t know. But it seems like he encountered the difficulty, and his instinct, at least that he developed over time, was to engage the difficulty. He developed discipline, curiosity, and willingness. I think he’s a great example, a belief that if some capacity could be developed rather than merely accepting “This is what’s happened to me.”

Here’s kind of the— You know, as a team, we meet a lot around the planner and the concepts. And the whole idea is, how can this help you? How can it help us, the planning? And I have this question just for our listeners, and it is: What limitation are you facing right now, and what part of your response still belongs to you?

Now here’s a cool planner activity we do when we’re working together and working with others. And it’s, you take the planner and you divide the— Just take one of your days or a notes page and draw a line down the middle, and on one side list the things you can control, and list on the other side the things that you can’t control but maybe you can influence. And then choose one action where you can take action versus becoming focused.

That’s a cool thing that I think somehow without his planner—or maybe he did have something he used—he learned that through a number of difficulties. And I know that more will come, actually, in this story as Misty shares. As he got older, he had some tough things too.

George: Yeah, that’s a really great point. And I think more than anything, we wanna make sure our listeners know that there is greatness in all of you if you’ll identify those things that you can build upon. It’ll help you in your life, and so that’s a great way to identify it. I also think it’s interesting, Misty, that here he has been able to overcome challenges—and like a lot of our listeners, they overcome challenges—and then again, you know, trials hit him. And so in his twenties— You know, what’d help our listeners to understand that even though he really built himself up physically, what happened to him in his early twenties that sorta changed his life?

Prepared for Greater Things

Misty: I like that you said that, George, about how [Laughter] sometimes challenges seem to just prepare us for harder things that are to come in our lives. And I don’t think we realize sometimes how important that is, that we realize that, you know, those things prepare us for something great, and great things tend to be challenging.

An intelligent man with an aptitude for politics

Well, he ends up going as a young man, seventeen years old, he goes to Harvard, becomes a very successful student. He’s very studious. He discovers an interest in politics, which is surprising to a lot of people. His father had actually tried his hand in politics a little bit and had not been very successful. But he feels that he has an aptitude for this, and so he begins spending a lot of time studying history and philosophy, politics, and he actually writes a book while he’s a college student, which is not a common thing. Ends up getting a book published.

He also, as a college student, ends up meeting his wife, Alice Hathaway Lee, and he is instantly smitten with her. And again, that determination comes into clutch because she’s not initially as interested in him, but he pursues her and eventually is able to—a year later, they get married. And so, and right after this, he ends up becoming the youngest member ever brought onto the New York State Assembly. So it’s his first hand in politics. He gets the opportunity to do that, and instantly he begins developing this reputation of somebody who looks out for the small man, for the lower class individual who’s just struggling to make it. And maybe this is something that’s born from his father, you know, who was a philanthropist.

Devastating heartbreak in the home

But things were really looking up for Roosevelt. His wife became pregnant, and so it looks like he’s finally gonna be able to build a family. He’s twenty-five years old, and while he’s in New York at the State Assembly, he gets a telegram that tells him that his daughter has been born, and he is ecstatic. But it is shortly followed by a telegram telling him that his wife is very ill. And so he immediately goes back home, and when he gets there, he finds out that not only is his wife ill, but his mother is also running a fever and has tuberculosis.

And throughout that night, he is making trips from the top to the bottom floor, taking care of his wife and taking care of his mother. And his wife is not able to recover from the strain of the delivery, and she— Well actually— Sorry, let me back up just a little bit, because about three a.m. on February 14 of 1884, his mother will die. And he’s there with the rest of his family as she passes away. He goes upstairs, and at two p.m. that afternoon, his wife passes away. So within a matter of hours, he loses two of the most influential women in his life, his mother and his wife, on Valentine’s Day. And Alice is twenty-two years old. She has her whole life ahead of her.

And to say that this was something that rocked Teddy Roosevelt is about the biggest understatement of all time. He actually was— so he was an avid journaler; he would write pages and pages. But for weeks after this experience, he didn’t write anything. On the day that they died, he drew a black X across the page and just wrote, “The light has gone out of my life.” This was so crippling for him that it seemed like his entire life had collapsed, and he didn’t know what to do. And he was so grief stricken that he ended up doing something kind of crazy, [Laughter] deciding that he needed to run away from this grief, which I guess kinda takes us into then next section of his life.

It’s what you do with your challenges that matters

George: I think this is really important to note, because I know a lot of people probably see success in their life, and then they have these challenges or, in this case, some people might be dealing with some major tragedy losses and things like that. And I think one of the things we can learn from this—and John, I wanna get your feedback—is that your circumstances in your life can define you or they can change you in a couple of different directions, but—and we’re gonna talk about how it affected Teddy Roosevelt—but how you view those situations and what you do about them will truly define your trajectory, right, John?

John: Yeah, I agree. We just did a podcast a few weeks ago on the transformative power of goals and, wow, every time we dig into that, I learn a ton. So far, we could say Roosevelt suffered, and therefore he became successful. It’s almost like as we move along in life, there are times when just the suffering and what you experience, you reach a point where something you had hoped maybe isn’t possible. He had hoped that those things didn’t happen.

And there’s an extremely relevant learning here, I think, that no matter what it is—bereavement or divorce or retirement or illness or job loss or challenges with children or relocation or caregiving, or simply anything—we will face things that we hadn’t seen before, but we have the ability to realize, “Hey, this is the present season of my life. I may need to adjust a goal.” But with, I think, the timeless principles of the greatness in you and your ability to take charge of this, it’s okay to adjust, reset. You can still be anchored by your values and move ahead.

And the thing is that we’re not experts in mental health, but what we do know from our research is as we plan, as we adjust, as we work on this, we really can succeed. And each of these make us stronger as kind of a blend of timeless principles and setting goals and working with what you have. That is a powerful, powerful, you know, learning to have.

Roosevelt Rebuilds Himself Out West

George: Yeah. Yeah, and also it’s important to note that, you know, it takes time to move through things, but obviously how you do that is important, and the way you adjust to major issues in your life. And so, Misty, you know, he made a decision to basically, you know, go west. He went west, into the— [Laughter] into the Wild West, right? To the Dakotas. And so help me understand and help our listeners understand why he went west and how this helped him to rebuild himself, and what happened in that phase of his life.

Misty: Well to begin, I should say that Roosevelt had a love for the outdoors and he had a love for the West even before this happened. He had taken a trip out to the West and was amazed at the beauty of the landscape and the hard work ethic of the people. And when this happened, it seems like something broke inside of Roosevelt, that he needed a change of scenery. And I mean, this is pretty common for people who go through traumatic experiences, of wanting to remake themselves and get away from those difficult experiences.

A new kind of test

I can’t remember who said this, but I recently read a quote that said in essence, “Trials introduce a man to himself.” And I think that that’s what I would classify— These Dakota years in the Dakota territory that Theodore Roosevelt spent is when he really came to know himself in a new way. Because he had obviously overcome a lot of physical challenges and built a lot of strength and stamina, but the Dakotas would test him in a way that was completely different.

If you know anything about the West, it was not for the faint of heart. You’re talking about, like…the natural elements that you’re battling constantly. It took hard people to forge the West. And so for a New York city slicker to go out and try to pass himself off as somebody who’s going to raise cattle, initially the locals didn’t— [Laughter] They saw him as somebody who was never going to survive in the West. They expected him to go back to New York very quickly. But he proved that he had the grit and the determination to try and make his way in that world. And he did take a lot of trips back to New York. He had to leave his daughter behind in the care of his sister, so I imagine that that had to be very difficult in and of itself.

Finding purpose in a new challenge

But I think, too, this was not an— I don’t want to paint this in a way that sounds like he just ran away from his challenges. Because I don’t think that’s what this was, so much. I think he just needed something to occupy himself. Something new and difficult that he could conquer. He was somebody that found a lot of purpose, right, in a new challenge, and there was nothing more challenging than what he undertook in this scenario.

And it’s actually in this period of his life that he begins to develop what will be his life philosophy which is The Strenuous Life, and he talks about that a lot. You’ll find in the writings of Theodore Roosevelt that in his mind, it is in the facing of challenges that a person becomes great. That you’re not supposed to run away from what is difficult; you need to find what is difficult and then purposely go after it. And I love Teddy Roosevelt for that reason, and I think that we can learn that from this period between 1884 and 1887 that he spent in the Dakotas.

George: Yeah, I think it’s not even just about having challenges to define you. At the end of the day, it is a little bit of your perspective on your challenges, and he really did have a philosophy of knowing that, you know, moving outside your comfort zone, challenging yourself, pushing yourself, is what was the solution. And so this is really one of those things where of course, you know, there may be a change in scenery needed at times, but he didn’t slow down, and he continued to move forward. John, do you have some thoughts on that section of his life?

The intersection of interests and values

John: Well, just a quick one, and that is, what I see in this is there was something that he loved. And when he had difficulty, he went to something he loved. An interest. And I think that’s super powerful; that is part of sharpening the saw, but also in a time… You know, think, in a time of pressure, things that you’re interested in, things that you love that also might represent values— An interest might represent a value, and eventually that might lead to even a great contribution when you bring those together. And I think the history shows that his love for the outdoors and different things affected how he governed as a president. So, think of sometimes your interests; the things you love are a great strength when times are tough.

George: Yeah, and what matters most to you and what you’re passionate about, and the more aware you are of that, the more those will guide you through difficult situations and things that you have.

The Start of Political Success

So there’s a section of his life that comes next, Misty, where I think maybe he’s, you know, very well known for, and it really determines— or maybe it’s a good example of courage and action, right? Because it’s this section of his life where he was drawn into the Spanish-American War; you know, formed the Rough Riders, this kind of area. So take us down that path. What drew Roosevelt into the Spanish-American War and that section of his life?

Misty: Absolutely. I think that a lot of people are not super acquainted with the Spanish-American War. It’s one that we kind of breeze over and we’re like, “Wait, what? That happened?” Yes, yes, it did. And Teddy Roosevelt, his— I have to say this too. Sorry, kinda backtracking just a little bit on his time in the Dakotas. He actually made this note where he said, “I would not have been president had it not been for my experience in North Dakota.” And I think we could say the same about his experience in the Spanish-American War, that his path would’ve been totally different had he not experienced those challenges.

Marriage to his future First Lady

Well, he decided—partly because his cattle ended up failing in the Dakotas; everyone’s did in that period because of a terrible winter that they experienced. But also, he— After that time to heal and process his grief, he decides to come back to New York. He actually ends up reconnecting with an old childhood friend named Edith Kermit Carow, who he will eventually marry not too long after this, actually, and they’ll have six children together. So he did eventually have that family.

And I wanna make a note of that just because sometimes we don’t credit the women enough as far as the influence that they have. Because Edith really was the partner that he needed to go into the presidency. She was very…she was brilliant. She was an amazing hostess, somebody that really was perfect for his political career.

Assistant Secretary of the Navy during the Spanish-American War

Well, he did end up going back into politics, held a couple of different positions. He helped to campaign for William McKinley, which, later William McKinley is going to return the favor and give him a position as the Assistant Secretary of the Navy. Well, he’s in that position when the Spanish-American War breaks out.

The Spanish-American War was… It erupted because Cuba had been trying to gain their independence from Spain. And Spain was not about to see that happen. Well, America decided because the USS Maine exploded and they figured that it was probably Spain that had done it, that awoke the American people, and they decided, “We should get involved and help Cuba to get their independence.”

Fighting alongside his men

Theodore Roosevelt was very in favor of this; especially, you know, as somebody who was overseeing the Navy, he was very invested in what was happening. But what’s incredible about this is, as war broke out and troops began to be sent over to Cuba to fight this war, Theodore Roosevelt was in a very cushy position. He could have just stayed right where he was. But he felt that he needed to practice what he preached, and decided that, “If I’m going to expect men to go out and fight and give their lives for this cause, then I need to be willing to do the same thing.”

And so he decides to go himself. He volunteers, and he helps to form the 1st United States Volunteer Cavalry, which is going to become known as the Rough Riders. And they’re called the Rough Riders because all of them are pretty much… I mean, they have various backgrounds, but most of them have been, you know… They’re tough, independent men who are accustomed to outdoor life.

Returning home a hero

And so this is going to be what launches him as a national figure, because he decided to lead from the front of his men, and he is going to lead a charge up San Juan Hill that’s going to be a pivotal turning point and be really important for America’s victory in this war. So when he comes back, he comes back as a hero, and this is what’s going to get him back into higher positions in politics.

George: Yeah, it’s interesting because those situations in your life not only define you but they put you on a path, and they put you into a trajectory that ultimately can determine your destiny. And so that’s kind of what I think happened there. Not only did he develop the skills and the, you know, the courage and all those types of things and worked through a lot of the challenges he has, but it put him on a path. And it really led him into politics, and I think politics even prior to the presidency, right? ’Cause he’s always had a little bit of interaction in politics.

Talk to me a little bit about what type of leader Teddy Roosevelt was. Because his values and what he was focused on and his leadership over just the politics itself— Help us to understand, you know, what type of a leader was he as he had this rise in politics in New York and becoming a governor and things like that.

A Good Man in a World of Corruption

Misty: The period that Theodore Roosevelt lived in as far as politics goes was viewed by many as pretty corrupt. Maybe that’s partly why people were surprised when they saw him wanting to go into politics. They’re like, “You what? You of all people?” And that was— And so you have to understand, especially in New York, that a lot of the politics were run by the big bosses who had a ton of influence. They were after money and power.

“A rigid moral compass”

And so when Teddy Roosevelt came back to New York and he suddenly became a candidate for becoming a governor, one of the most powerful Republican—the most, I should say—the most powerful Republican boss was Thomas C. Platt. And he initially was like, “I don’t know if I want this guy getting into power.” He said, “But, ah,” he’s like, “Ah, he’s young still, I could probably influence him a little bit.” But he and everyone else in that sphere of influence found out pretty fast that nobody told Theodore Roosevelt what to do. He was somebody who knew his own mind, had like a rigid moral compass when it came to his public life and his private life. And that’s something definitely to be admired about Teddy Roosevelt. And he fought against the corruption that existed there on all levels.

And this is something wonderful too, is that you would think as somebody who had experienced such privilege in his life that he would not be really focused on, you know, the lower class citizens or people that are struggling in workhouses and factories. But he was not that way at all. He was very aware of that and sought to improve their condition constantly. And so that was something that really characterized his governorship, and it was—actually, he fought corruption so much, and the monopolies also is another one of his legacies, is fighting against big monopolies.

A scheme against Roosevelt

But the bosses were so frustrated about everything that he was doing that ruined all of their schemes that they actually conspired, like, “How do we get rid of this guy?” Like, “We know—let’s get him to run as vice president! The vice president doesn’t actually really do anything, doesn’t have a lot of power. We’ll just get him out of here by putting him on the ticket.” And so that’s what they did, and he ended up becoming vice president to William McKinley on his second term.

George: Yeah, it’s interesting, ’cause if I back up just a quick step, it’s— You said something that was important, ’cause most people get into politics or leadership because of the power, the influence, the notoriety. But when he did, he really took on corruption, and I think it’s a good lesson for us to learn from in the sense of, what are your motives? What matters to you? What’s important? Because he had values that he truly had guide him in what he was doing, even when it created enemies, even when it created people that were working against him while he was, you know, governor and leading.

And it really took him next into the presidency and this idea. So there’s this next level of his life or, you know, section of his life. But as we get into that, one of the things I wanted to comment on is, I think sometimes when we’re trying to determine what matters most to us, a lot of people get caught up in what other people think, and they’re living a life that’s based on other people’s values.

Staying true to his own values

And Teddy Roosevelt was a great example of someone who maintained his values, kept those consistent, and had it drive what he did in his life, especially in leadership. And so when he had these values of really fighting corruption and working to help the lower class, like you said, I think it’s a good example of someone who was principlely driven versus somebody that was influenced by his surroundings, wouldn’t you say?

Misty: Absolutely. Absolutely. And that’s something that would characterize his entire time in politics. And as we get into how he ultimately comes into the presidency, it’s interesting how fate conspires [Laughter] because—

George: Yeah, so let’s talk about that, because at the end of the day, you know, was Roosevelt prepared when the presidency suddenly came to him? And let’s talk about how that all came together. What happened there and what brought him into the presidency?

President Roosevelt

Misty: Well, when you say prepared, whether he was “prepared”—I don’t know that he expected it, but I think that his whole life had been in preparation for this moment—

George: Hm. Good point, yeah.

Misty: —in more ways than one, because— So his father was from New York, which I already mentioned earlier, but his mother was actually from the South and had been raised in Georgia. And so Teddy Roosevelt lived in a time when the North and South were still in such great conflict. I mean, when he was born… I think he was six years old when Abraham Lincoln was assassinated.

He understood the needs of the nation

And so a lot of the events surrounding the Civil War are still so fresh, but he came into this with an appreciation for the North because of his father and the South because of his mother. And his time in the West had given him an understanding of what expansion was going to mean for the country. And I think that that put him in a unique position to understand the needs of the nation at the time he came into the presidency.

But of course, the circumstances that brought him into it were very surprising, because William McKinley was shot by an anarchist—assassinated—and three days later, he died. So that’s, of course, gonna be a really traumatic entrance into power, and Teddy Roosevelt actually said something along the lines of how the vice president is— he said, “He may be everything at any moment, but until then, he is next to nothing.” So—

“His whole life prepared him”

George: Yeah, you make a really good point because, you know, John, we were talking about how this idea that he—was he prepared for the presidency? Well, his whole life prepared him for the presidency. And so, how important is it to both have, you know, these principles throughout life prepare you for that, but also be prepared at any moment to be able to truly create legacy, create change, and things like that?

John: I see courage and humility in these last few minutes, and I ask myself: Where do I need courage? And also, where do I need enough humility, like he did with Leonard Wood to let him lead when he could have led. So just going back, where do I need humility to ask for help, to accept help, and also support others that may be in more formal roles leading? That’s actually a really bold way to live, versus, you know, you’re leading all the time or… Anyway, I really love those examples.

George: Yeah, that’s so true, and I guess, Misty, a good question would be, you know, what did he really believe the role of the president should be? Like, what was his philosophy on the presidency?

Revolutionizing the Presidency

Misty: Well, Teddy Roosevelt, he’s seen as one of the first, like, modern presidents. He led us into a new century. And he did have a different idea of what a president should do or should be like. A lot of those who came before him, the presidents—especially, you know, in between him and Abraham Lincoln—had had kind of a hands-off approach a little bit, letting Congress take the lead on most things.

Wielding power noblely

And so when Teddy Roosevelt came in, he did take a lot more power into the presidency in his hands and made more decisions and upturned things a lot more than those who had come before him. He came in with this idea that government was meant to help the people in every way that they could. And so that’s what really determined a lot of the decisions that he made.

Policies for the people

He had what he called his Square Deal policies, which involved three Cs, you might say: the control of corporations, consumer protection, and the conservation of natural resources. And so this came down to him, again, working against corruption, what he called trust-busting—you know, breaking up monopolies, and then also, you know, trying to make it— I mean, he was involved in things even like making sure meat was clean, that food was held to higher standards so that people wouldn’t get sick, or that people had better working conditions.

And of course we also remember him for conservation, probably more than just about anything else he did in his Presidency. We think of him as the person who put aside thousands of acres of land for future generations. And in his mind, that was his responsibility for those who would come after him. So again, everything that he did came from a very ethical standpoint, that he felt that he needed to good with his position.

George: Yeah, it’s a great example how your philosophy shapes your life and the people around you. And I think this is what really drives to his overall legacy. And I wanna talk with both of you, before we end the podcast here, about his legacy, some final thoughts of people remembering and knowing these ideas, like “The Man in the Arena.” But before we do that, I would like to really pull this back towards the overall life of Theodore Roosevelt and how his systems and values and thoughts for life really apply to our listeners and to Franklin Planner systems, as well as how you lead your life intentionally.

What We Can Learn

So John, I’d like to kinda start with your thoughts on how you feel Theodore Roosevelt’s life really applies now to how you can lead your life and maintain direction and values.

Even incredible people aren’t perfect

John: He had a strong bias towards engaging—you know, stepping forward, and letting steps be guided versus waiting, overanalyzing. These are things that we see, and while I’m sure he had all the weaknesses that we all have— I thought it was interesting, last week when we interviewed John Covey, a nephew to Stephen R. Covey, he called him Uncle Steve, and the first thing he said, he says, “He’s not a perfect man.” I know that some people might think that, or that we think that, but what he did contribute was he moved— And I guess that that’s initiative of bias for action.

I sense a humility that he was willing… At least he has some very clear times where he could have said, “Hey, I’m great. I’m in charge. I’m doing this.” It’s kind of a humility to step back. And then I like how he brought this to the presidency in his life, that there was responsibility that went with power and kind of a stewardship, which I believe is a deep respect for others, is a deep respect for people around you, whether they’re people you know and love or just people you don’t know. And so I just think he’s a great example of aligning himself to timeless principles and moving forward despite, probably, an endless list of challenges we all have to help us grow.

George: Right. Yeah, no, I agree. I agree. And Misty, maybe you could just give us a thought as well on his overall daily disciplines and, you know, habits of learning and physical, and how that sort of applies to our listeners and people today, what they can take from that in helping them in their lives.

Misty: Well, Theodore Roosevelt is somebody who constantly challenged himself, whether that was mentally, physically, emotionally, even. And I mean, that’s where he gets that—you know, we think about him boxing, and we imagine that, and I’m glad that John brought up this point, though, that Teddy Roosevelt wasn’t perfect. Sometimes when we talk about people in the past, we’re like, “Oh, they were so great,” and we don’t— Obviously in this setting, we’re gonna talk about the great things he did.

An inspiring passage from “The Man in the Arena”

But of course, Teddy Roosevelt, he did make mistakes, and there are people who will look back and criticize him for certain decisions that he made as president, or in any of the positions that he held. But I love something that he said himself in a speech that he actually gave in Paris. He gave this in a speech that he called “The Man in the Arena.” And to me, this just embodies everything that he believed, and it’s very inspiring to me.

So he said this. He said, “It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.” Even though we don’t do things perfectly, it’s important that we do them. That’s what matters.

Build your life through your choices

George: I think that’s such a great thought for us as we start to end this episode, because the Man in the Arena philosophy, Roosevelt’s story, is a powerful reinforcement of a lot of the Franklin Planner principles, which are: a meaningful life isn’t simply something that happens to you, it’s something you intentionally build through your choices, your habits, priorities, and actions. And your philosophy will steer your legacy for sure. So John, let me give you… What are your final thoughts here as we wrap things up? What are your thoughts overall?

John: I’m grateful to have been here with you and with the listeners. I think it’s interesting that leadership—and when we profile in this leadership series these amazing founders, personalities, men and women in the United States of America, and as we also studied others—that I don’t think leadership history is a hero to worship. But it’s learning, right? It’s learning for us.

And when I think about Roosevelt—and there’s so many things we could say about how he expanded things, he pushed us onto the international scene more, he did all kinds of things—but I kind of like thinking, what did Roosevelt do with the next page? You know, when he encountered something. And kind of thinking of, you know, what we can write down and inspired ideas we have. What can we do when something is coming our way we don’t know about and happens? What does this experience have to teach me? I saw that in him.

Stay anchored to your values

And I think, George, I just would like to suggest we think about our lives, the values we have, and the power we have. And it doesn’t mean fear doesn’t come our way. It doesn’t mean doubts don’t come our way. But when they do come our way, I do believe there’s a fearless way that we can dismiss those fears. If we’re anchored, you know, on the things we value, and we go forward each day, and we plan, and we use the power within us. There is greatness in us, there’s a leader in us, and there’s a capacity to also help others.

And so I just think as we conclude this and this particular story of this particular man…his story is ended, but our story continues. And I have so many great examples around me, including you two, of people facing these things. And so I just almost, you know, wanna send out a congratulations and a thank you to all of those that kinda see the vision of these values and take it forward. Thanks for having the conversation with us.

George: Yeah, that’s great. Thank you so much. And Misty, do you have any final thoughts, or maybe you’d like to give our listeners a personal challenge or invitation?

Dare to confront your challenges

Misty: Yeah, I would love to do that. I think looking at Teddy Roosevelt’s life… You know, he’s somebody who built the Panama Canal. He launched America into becoming a world power. And I think about if he were here, what he would say to us. I think the advice that he would give us is that it’s not the easy life, it is the strenuous life that makes a difference. Now all we have to do is be willing to dare and to do great deeds, to challenge ourselves.

And so my invitation to the audience would be: Think of what is most terrifying to you. What is something that you find very challenging? Whether that’s something in your habits that you want to tackle or change, or if there’s something that you really want to accomplish but it terrifies you, then that’s exactly what you should do. [Laughter] I would recommend that you decide what it is that scares you the most, and Teddy Roosevelt would tell you to dare, because that is where greatness lies.

George: I love it. I love it. Lean into that. Lean into your fears, lean into the difficulties in life, because it not only shapes you and directs you, but it can cause some major legacy in a positive direction, which is what happened with Theodore Roosevelt. So, great. Well, I appreciate you guys both being here. I appreciate the listeners. As for the reason that we did this episode as well as the series was we wanted to bring you that inspiration, those ideas, those those things that will challenge your thinking but also give you some timeless principles you can use not just in your life, not just to focus on what you value most and what matters most, but also for productivity and examples to follow.

So do us a favor: follow the show, make sure you share the show. We’re excited to bring these ideas to you, but we also want to hear from you as well, so hit us up at Franklin Planner. You can also go to Franklin Planner Podcast social media properties; let us know what you’re dealing with, let us know what you’re working on. We wanna be able to celebrate the wins and also bring you more topics that you’re looking for. And with that said, we really appreciate you being here. We hope you have an amazing day, and we will talk with you soon.

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Thank you for joining us on this Journey to create your best life and to lead your Life and Teams. Please share this show, and we look forward to the journey we will take together.

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The Franklin Planner Team

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About Misty Howard

Misty Howard is a historian‐enthusiast and podcast host who brings a fresh, youth-oriented voice to timeless values and historical wisdom. She serves as the creator and host of the podcast Faith Ignited (described as “Immersive, real stories from history, seen through the lens of faith”). Her work focuses on exploring the lives of influential historical figures—especially from the founding era of the United States—and connecting their personal values with modern leadership, mission-driven living, and character development. Misty emphasizes the importance of self-improvement, purpose, and narration of historical truths often overlooked in mainstream narratives. Her style blends historical research, faith-based insight, and practical application for younger audiences.

Her contributions bring depth, perspective, and inspiration to conversations about proactive living and principle-centered leadership.

Guest Resources:

Podcast Link: Faith Ignited — available via Apple Podcasts, Pocket Casts, etc.