The Leadership Advice Nobody Follows (But Everyone Should) from Top Leadership Expert

I'm constantly looking for things I appreciate, things I love. And if you're looking for things you love in your friendships, in your relationships, if you're looking for things you love, you see more of them.

Ah, this is a great lesson. Your job becomes find things I like. You make it your job to find where people are actually going the extra mile, doing a little more, you know, doing good work. Even if it's a small thing, sort of say thank you, and you'll find you get more of it. Don Yaeger is the preeminent expert on John Wooden. John Wooden is the greatest coach in college basketball history. Whether you care about basketball or not, if you're interested in leadership like I am, you have to study John Wooden, which means you have to talk to Don Yaeger. This is why I was so excited to have Don on the podcast, to talk to him about love letters. With the release of his newest book, Mastering the Art of Storytelling, Don has written 44 books, including 13 New York Times bestsellers. A former associate editor at Sports Illustrated, he's interviewed the great athletes of our generation: Michael Jordan, Serena Williams, Michael Phelps, and of course, Coach John Wooden. And it was Coach Wooden who taught Don the power of a good love letter. After Coach Wooden's wife passed away, he wrote her a love letter.

She had passed away on the 21st day of the month, and every month for 25 years, on the 21st day, he wrote a love letter to his wife.

When Dunn asked if there was anything in those letters he wished he would have said while she was alive, Wooden replied, "All of it." Coach Wooden taught Dunn something simple but easy to forget. We assume there will always be time, but the best time to tell someone how much they mean to us is now. This is A Bit of Optimism. Don, it's such a treat to sit down with you. Your ability to tell a story, quite frankly, is captivating, and I know you've written a million books and had bazillions of New York Times bestsellers, but to sit down with you is something completely different. I could just sit back and listen to you the whole time. In fact, why don't I sit back and let you just tell stories, and I'll be very, very happy. You started off as a journalist. Yes. What did you do as a little kid? Like, what did you want to be when you grew up kind of thing? How did you come to journalism?

So it's funny, you could argue that I was meant for it. My father was a preacher. We lived in Hawaii, which is where I was born and raised. We ended up in Japan, and while we were in—

Military?

No, he was a Methodist preacher, but we were in Japan and my job was to deliver the newspaper, the Stars and Stripes. So I would get up every morning, 5 AM, go to the place, pick up the papers, deliver them to every place. Then I would come home and I would put recording session in progress on the outside of my door. And I would read parts of the newspaper into a recorder and then I would opine about what was happening at that time. And I'm 11, right, right. And so I, I loved the news. I loved what was happening in the world. I loved curiosity, and journalism really just kind of satiated all those things for me.

So you were in the school newspaper in high school? I mean, one of the very few people on the planet that literally was on a path, yeah, from, from a young age and actually brought that path to life.

That's correct.

And you studied journalism, and then where did you go? You went to Hard News?

Ball State University.

That's in Indiana, isn't it?

In Indiana. I went to the San Antonio newspaper, San Antonio It was the large paper in San Antonio. From there, after a couple of years, I went to the Dallas Morning News, and then I wanted to do politics, so I moved to Florida to be the political editor of a large newspaper. After a few years of that, I got an opportunity to go to Sports Illustrated, which was quite the departure. They only have, you know, about 30 writers for Sports Illustrated at any given time, and I got an opportunity to be wrapped around these people that I thought were so fantastic at every given moment and learn every day about the great skill that it took to tell stories as they did.

So what Sports Illustrated did is it opened up an opportunity for you to meet John Wooden. And you, I think it's fair to say, are the preeminent expert— is that the word to use— on John Wooden. You spent more time than anybody else other than probably his family and his— and maybe his teammates. John Wooden, this great basketball coach who's considered one of the greatest coaches of all time, His philosophies are sort of counter to what a lot of people think. One of the reasons I wanted to sit down with you, I wanted you to sort of share some of the things you learned from getting to spend so much time with Wooden about leadership and human behavior.

He would have been, by the way, he would have been a great Simon Sinek fan because you and he think so much alike. He believed that performance was fully driven by relationship. In fact, there were times he would run practices without basketballs. Right? I mean, think about it. You're a basketball team practicing shooting, but there's no ball in your hand. You had to visualize seeing it through, going it through the net, because the truth is, if you actually shoot it, there are times it won't go through the net, right? So he actually understood the power of, of, of the mind and how the mind could influence behavior.

And for people who don't know who John Wooden was, can you just sort of very quickly say why he's renowned and famous as a, as a coach?

He won 10 national championships while being the head coach at UCLA.

Is that a lot?

That is twice as many as anybody else in history.

And that's—

that statistic remains today, right?

He won the highest winning team.

Mike Krzyzewski has 5, right? Adolph Rupp at Kentucky has 5, but those two are the next in line after John Wooden's 10, right? And so— and he did that in a 12-year window.

Right?

He won 7 championships in a row at one stage. Wow. And you're playing with different players all the time because kids graduate.

You can't simply— people can't brush it off and say, oh, you were lucky you had the best players for 10 straight years, right? Or 12, because that's impossible in college, right?

They're, they're rotating off, they're moving. And back then, college players could only play for 3 years, so he had to constantly be developing. And, and the thing that made him so special was that he didn't have a way of winning, he adapted to the players that he brought onto his team. So if he wins the national championship with a 6'5" center, that's awesome. But the next year he has Kareem Abdul-Jabbar, who's 7'1". And so, you know, now it's a whole different game for him. He changed based upon the assets, the talent that he was graced with.

The thing that I have found amazing about Wooden is the winningmost coach in college basketball history was not obsessed with winning.

No.

And I think for a lot of leaders who are obsessed with performance and obsessed with outcome and obsessed with hitting numbers, to learn that somebody who had greater success than all the others was not obsessed with winning— reconcile that for me.

Yeah. When he was a high school basketball coach, high school coach, he built a pyramid of success, right? Of here are the blocks of what it meant to be successful, and it's industriousness and it's a willingness to be team first. It was all of these elements. And you get to the very top, and the top block was greatness. And he believed that you build yourself toward greatness. You don't take greatness on. And he never in any of these conversations talked about what it meant to be a champion. What he talked about was what it meant to be great in our universe. If we're good together, good things will happen.

So I understand he— it wasn't about being a champion but being a great teammate.

Correct. And being a team of great teammates. It's one thing to have— so many teams have good superstars and good teammates, and often the teammates are the they're just lucky to be here, right? This was— your best player also was committed to being a servant leader.

How did he manage ego? So let's take someone who truly is gifted in the sport and maybe even has a remarkable work ethic.

Yeah.

And so they carry themselves like, I'm the champ, you couldn't win without me. How did he manage ego? How did he teach, you know, teamwork to somebody who truly is a superstar?

Because he understood— he now used to say, I believe in patting everyone on the back, some of them a little lower than others, but you know, so, but I pat everybody on the back. But his whole model of leadership was this concept that you need to have a series of standards that you will hold everyone to. Your best player, your worst player, everyone abides by these standards. And sometimes Your best players will push that envelope and try to see, do you really mean that for me? I'm the best player. He had Bill Walton, right, one of the greatest centers of all time. Bill Walton liked to have hair that was a little longer than everybody else. It was the '70s when he was there. And so one day, for Bill's senior year— he was the 2-time National Player of the Year— senior year, he shows up for the team photo with long hair. Coach Wooden had a rule. We don't have long hair here. Because he believed that you would shower after a game, most people don't dry their hair well, you go out into the cold winter of some of the places they played, you catch a cold. If you catch a cold, you're not available. If you're not available, we don't win. You're disappointing the rest of your team by not being available. So he had a rule about hair, but he had a reason for it, right? Right. And Bill Walton decided, you know what, I'm best player in the world, best player in America, I'm just going to show up with long hair for Senior photo day, and John Wooden said, Bill, what's the story with your hair? And he says, well, Coach, you always encourage me to think independently, and independently I think long hair is good. And he says, you know what, Bill, I'm so glad you think that way, and we'll miss you. And Bill Walton went out, found a kid who was riding by on a bicycle, asked the kid if he could borrow the bike, rode the bike down to a haircut place, came back 30 minutes later with his haircut because he realized Coach Wooden had a standard, and we'll miss you was his answer. And suddenly Bill Walton didn't want to test to find out, is being the best player on the team going to give me a little more grace than anybody else?

So when you say standards, you don't mean performance standards?

Oh no, these are standards of being. This is what it means to be part of our team. This is how you're going to cheer for each other. He required that if you hit a basket but somebody had passed you the ball, that as you ran down the court, you need to look at him and point and say, thank you, thanks for passing me the ball, right? Because there was joy in recognition, right? And, and often the person scoring gets all the recognition, the person who passes it doesn't. He required that on the way down the court you look for any point.

It's an ego check too, right? Yeah, like you didn't get that basket by yourself.

So we, we do this together. Yeah, one of his players actually said to him, but Coach, what if I go to run down the court, the guy's not looking at me when I want to point at him? Coach said, if the guy knows you're going to point, he'll look at you, right? And so these are the kinds of things he was doing to try to establish not basketball standards, human standards. And if they were better together as a group of humans, they could win. And they won a lot.

And now name some of the players who came out of those teams that went on to the NBA.

Oh my gosh, well, one stage he had 26 All-Americans. Played for him over the course of several years. Walton, Kareem Abdul-Jabbar, Sidney Wicks, Henry Bibby, Marcus Johnson. I mean, you know, some of the biggest names in, in college and then ultimately the NBA all came from that window of time when they were best in class.

And I mean, I'm not a huge basketball fan. I do know Kareem Abdul-Jabbar.

Yeah.

And one of the things I know about him is he was known for his humility and being a great teammate. And even though he was a remarkable talent and a remarkable player unto himself, There was a— and to this day, a humility that he embodies.

And so much of that came from the environment.

Yeah, you know, this is why I think it's important whether somebody likes— you know, I'm not a basketball fan, but I do love the stories about Wooden because they're so universally applicable. Correct. And, you know, even the stuff I talk about, it's so funny in this modern day and age, you know, I'll talk about Navy SEALs and I'll talk about these high-performing teams or Wooden, and in all those cases we're talking about high-performing teams, and people take those ideas and those lessons and they try to apply them to individuals. And I always get a kick out of that, right? You know, we forget that all of the stuff only works because there's a group of us. A company is literally a group of people. That's what a company means, right?

And if we can pull that group of people together, if they can believe that when they've given you an assist you'll notice them, right? It's amazing how many assists you'll get.

What kind of person was Wooden? Sometimes what they're known for and who they are sometimes align. You hope they align. You know, they always say don't meet your heroes.

Yeah, you know, and I will tell you, over the course of my career, I've had some of those experiences where you don't want to meet your heroes. John Wooden does not apply. He was the greatest coach of all time and a better man. He taught me in our conversations, and I had the honor over 12 years, the last 12 years of his life, to have him as a mentor. And we ended up in a relationship that allowed me every other month for 12 years to fly to California to spend a day with John Wooden. And the responsibility was mine to lead the conversation. I had to come with a series of things I wanted to learn. When I was out of questions, the session ended.

He was no BS.

Oh no. And every day had to open in a mentorship relationship with him. I had to say, Coach, here's what you taught me 2 months ago when we were here together. Here's how I've used it in the interim. And here's how I'm better as a result. He needed to hear that it wasn't just me soaking up time with him.

He needed to know that he was changing me, because otherwise it's his time wasted, right?

Right, exactly. It was my job to come prepared to let him know how I used what he taught me to be better. It's better as a father, better as a husband, better as an employer, better as a, you know, a speaker, or whatever it is that I was out doing, right? He wanted me to, um, to come back to him with, with something I took and, and show how I became better as a result.

How did he help you be a better husband?

Coach Wooden, he's a great husband. He married the only woman he ever kissed, and sadly, she had passed away 25 years before he did, ultimately. And in that 25-year window, she had passed away on the 21st day of the month. And every month for 25 years, on the 21st day, if you were there to meet John Wooden, if you had an appointment with Coach Wooden, he didn't meet with you in person until he wrote a love letter to his wife. And he wrote these beautiful love letters. His penmanship was fantastic, and they would often be a page, maybe page and a half long. And then he would seal the envelope, lick it, seal the envelope, and he would walk into her side of the bedroom where her bed was still made up where she would have slept, and he would take last month's letter and put it in a box, and he would take this month's letter and lay it on the pillow. And, um, you know, one, one year— and I, I, I could probably tell you exactly when it was, um, it was November-ish of that year— I happened to be there on the 21st day. And so I had to sit at the dining room table as Coach sat there at the table and wrote this letter to his wife. And when he came back after putting it at her bed, he looked at me and I said, Coach, you write these letters every month, you've been doing it for years, there are boxes of them. Is there anything there you wish you had said to her while she was alive? And he said, all of it. I said, excuse me? He goes, oh yeah. He said, it's one of the great weaknesses for most of us as people our friends and our loved ones, the people that we are so engaged with, we're so busy telling everybody else how great they are, we forget to tell them how much we love them. And he said, I wished I had said these things when she was alive.

He said more to his players than to his wife.

Yeah, yeah. And he says, so these letters are my opportunity to get that, get that chance. Well, I was so taken by it that that year I went home and for Christmas I gave my wife a box with 52 letters in it. 52 letters where I expressed to her something I loved about her in each and every one of them. I made a list and I, and I knew what I wanted to write in each letter. And that Christmas, I mean, like, I didn't matter what I gave her, that was the gift, right? And it meant so much to her that the next Christmas I did it again and I did it again. And just last Friday she opened letter number 848 Wow. So however many years that is, is how many years it's been since I started doing it. And they're all different.

So she takes the box and opens one a week, right?

She opens one a week. Yeah. And then she keeps all the letters. Wow. She loves to point them out to my daughter and say, by the way, I hope one day you marry somebody that will love you enough to write you a letter. Wow. And, um, yeah, Coach Wood made me a better father, made me a better husband. I mean, there have been times when in our relationship where I'm pretty sure the letter saved me, you know, because I may have done something that really made her mad and whatever it might be. And then ultimately she'd go, yeah, but this guy's written me 500 letters, right? You know? And so, I mean, there's a little grace that I get, a little extra grace that probably plays into our marriage. It's been without question, it's John Wooden changed my life, changed my marriage.

What have you learned about your wife in writing a letter a week? Because you're forced to sit down and think, because I would imagine the first 10 or 15 were easy.

Yeah, smile, love the way you smile, your sense of humor, right?

Yeah, like, yeah, I got it. But when you start getting up to like 50, 60, 70, you're like, uh, love how you cooked my eggs this morning.

Well, I haven't gone there.

It was a perfect scrambled egg. No one can make scrambled eggs quite like you. I mean, it's like, I want to know what you've learned about her after, you know, over 800 letters.

I will tell you what it's done for me. Yeah. Is, you know, I mean, I just, I know so many friends who I'll sit with at lunch. They'll tell me all the horrible things their wife does. Like she doesn't put the toilet paper over right, right. Or, you know, she doesn't fold the towels like I like them. And, um, and I don't think about those things, but I know men who do. I know men who, who think about, you know, Gosh, the relationship they have, it's so troubled because she's an over-the-toilet-paper instead of under-the-toilet-paper kind of woman. And I know it sounds silly, but there are people out there who are looking for reasons to think less of someone else. I'm always looking for something. I write them all the time. I have a database on my computer of all the letters I've written, and I've got the next 75 or 80 already crafted, right, of what they're going to be. Next Christmas is already taken care of. Because I'm constantly looking for things I appreciate, things I love. And if you're looking for things you love in your friends, in your friendships, in your relationships, if you're looking for things you love, you see more of them.

Oh, this is a great lesson. You know, if you know you have the assignment to write the letter and you got to write something good, then as you said, your job becomes find things I like. That becomes your job, right? And this is, you know, Bob Chapman and, you know, dear to my heart, he would say of his employees, don't catch people doing things wrong, catch people doing things right.

Right.

And it's the same thing if you make it your job to find where people are actually going the extra mile, doing a little more, you know, doing good work, even if it's a small thing, sort of say thank you, and you'll find you get more of it. Plus it's fun to catch people doing things right because the other becomes insidious, right? Which is if you start looking for things wrong You'll find them. You start looking for things wrong. Just happened to me this morning, which is there's a couple things that happened at work that I've like reacted to and sent a note going, hey, this happened, let's not let it happen again, you know. And then it happened again. I was like, hey, this happened, let's not let it happen again. And so in a meeting today, I said, hey, I don't like this. I don't like reacting. I don't want to react. I I've got to believe that it sucks to be on the other end, on the other end of me reacting. Can you tell me what's going on that it's not working? And because I don't want to be this and you don't want to be in the receiving end of it. And they give me a very logical explanation as to why it happens. Turns out it was just a technological glitch, you know, not a human, not human failing at all.

But where do we go?

And we go, who screwed this up?

Right, right. And if we were in fact—

right—

give the grace and the opportunity and the open door for that conversation to occur.

And so the lesson for me was, of course I'm gonna notice things that go wrong, of course. But by asking the question, as opposed to coming in, because I don't wanna be the person who's always looking for things going wrong, that I just got an explanation that made sense, and now I can be like, great. And now that I understand the technological glitch, I can see what went right and be like, that was good, as opposed to focusing on the thing that didn't work. It's such a— I mean, it's so overdone and so overused, you know, the idea of what your mindset is. But it really is the mindset of giving people the benefit of the doubt, being curious, and looking for good.

Coach Wooden said, you will often find what you're looking for.

Yeah, you always find what you're looking for, right?

And so I have just taken that lesson from him. I didn't want to look back one day and say, I wished I'd written those things while, while she was alive, right? I didn't want to have—

you don't have the same—

I didn't want to have the same regret.

Yeah.

And so taking that moment of regret became probably one of the greatest things that's happened to me in my relational life.

Okay, I'm going to keep going because you're a font of this amazing stuff. Great corporate leaders that you've had the opportunity to, to either help them write their books or just help them, you know, maybe writing an article, that somebody who was even better than you expected— like, yes, they have their reputation but then you sit down with them, you're like, whoa, this is not smoke and mirrors. You know, I'm very curious who you met was not just good, as good as their reputation, but even better than their reputation.

I will tell you, the one that I'm just so fascinated with and have been working with for the last couple of years is Ed Bastian, the CEO of Delta. Yeah, yeah, we just finished writing a book together. It'll come out later this year. Many people think, well, you know, the customer's always right. That's not his philosophy. His philosophy is, I really want to understand my employees, and if they know they're cared for, they will care for the customer so the customer doesn't have to argue about what's right or what's wrong, right? And so he actually has what he calls a virtuous cycle. I'm going to go to work every day on making the opportunity for my employees to be successful as real as possible. I'm going to give them the assets they need. I'm going to give them the training they need. I'm going to give them the love they— that will make them feel appreciated. And if those things exist in, in the people that we're hiring and that we're putting out on the front line, they then will treat our customers, right, with the same level of dignity and, and positivity and energy. And if the customers are feeling that same level, they will then buy our product, maybe at a premium price, which Delta is known for. And as a result, I now have the revenue to take care of our employees better. I love it, right? He does every year 10% of corporate profit goes back to the employees in profit sharing. It's a cool thing, but he gives it to them on Valentine's Day. It's a love letter from the CEO, right? It's an opportunity to— on Valentine's Day, every employee at Delta knows, and for most of them, it's the equivalent of 1/12 of their income, right? They're, they're making that back if the company's profitable. Sure. When it's not, they, you know, it doesn't happen. But his ability to just And to stand up for employees and to believe that, that, that he is creating an environment for them that gives them their best chance for success is meaningful.

Hard to do at scale, right? Wooden had 5 guys on the court at any one time, right?

Ed Bastian has 120,000.

120,000. And, you know, there are many things standing in the way, you know, distributed workforce with hubs all over the world.

Um, there's TSA, TSA challenges, regulations. One thing that's interesting is that Delta is the only airline— they have a pilots union because all pilots are represented by the same union, um, but no other aspect of their organization is unionized.

And I remember they voted because Northwest was a union shop, and when they bought Northwest, I think I've got my math right, yep, they had to vote to deserve to vote.

And the—

it was the Delta employees that outnumbered the Northwest employees, right, that actually voted no, we're good, they take care of us. Right, we don't need it. Like, we want it if the company screws us, right, obviously, but we're good.

But I think it was the overwhelming— in a highly unionized industry, to be able to, to constantly keep your employees believing their best days, yeah, are when they're in the company of leadership as opposed to in the company.

And, and, you know, and, and just so people don't, you know, sort of write angry letters and things, you know, I understand that it's imperfect. I also understand that scale is difficult. It is an imperfect airline, but I like the attitude and I like the striving, which is the most important part.

Yeah. We began working on the book, uh, many years, several years ago, right after COVID. And one of the things that really fascinated me about COVID was he believed that in moments of crisis, your job as a leader is to overcommunicate. So he would sit on a white chair, much like ours here, in the corner of his office. And every morning he would livestream to all employees and he would tell them what he knew. And he would tell them when he didn't know the answer. He would take questions from employees, but he overcommunicated in that moment where a lot— when things are tough, it's the easiest thing to do is to say, I'm so busy, I don't have time to go step out front. It's harder to make it a regular piece of your being to actually deliver to those people even messages that might not always be comfortable.

Okay, so we've got a coach, we've got a CEO, history. You've written books about history as well. I have. Is there a historical leader that, as you're doing the research, as you're writing the book— because I know this from writing books, which is, you know, you go down rabbit holes like crazy, some of them good, some of them not so useful. The learning that I get from researching a book is better than the book because not everything goes in the book, right?

Can't— it can't.

And I know that I'm a better person because I researched and wrote the book, because I learned so much from other people and what other people are doing or other nuances. Was there a project that you worked on, a historical project that you worked on, that you are a different person having written, having learned those lessons, written the book?

I would argue it's one I'm working on right now, on Teddy Roosevelt and his son Teddy Roosevelt Jr. Teddy Roosevelt had a father who actually paid someone to take his place in the Civil War so he didn't go out and potentially be injured, right? Which was not completely uncommon, but still, it was dishonorable in Teddy Roosevelt's opinion.

Right, that he had a rich family that could pay for him not to go to war.

Right, and so he, Teddy, said, you know what, I will be none of that. And as you know, I mean, you look at his historic efforts on the battlefield and otherwise, Teddy Roosevelt never ran never ran from an opportunity to fight, right? Then he becomes president, and in the process of all that, he has a son, Teddy Roosevelt Jr., who is struggling mightily because he's thinking, how do I live up to a father that's so extraordinary? Yeah, how do I do that? And studying the dynamic of these two men, father and son, yeah, and how they— is, is a great— I mean, I'm, I've got a 17-year-old son, and it's a great open door for my son and I to engage in conversation. We're going to Normandy this summer because Teddy Roosevelt Jr. is the only general officer who actually stormed the beaches of Normandy with his troops.

So a star on his shoulder.

He has a star on his shoulder.

And he's in the Higgins.

And he took Omaha, he went on to Omaha Beach and actually, you know, he was using a walking cane because he was a little older at that stage and had been injured.

He must have believed that this was his last stand.

Well, he died 36 days later, ironically, but the bottom line is that.

But he He didn't die on the beaches of Normandy, right?

He didn't die on the beaches of Normandy. He's recognized with, you know, the Presidential Medal of Freedom. He's got, you know—

so what's the parenting lesson then?

Yeah, so the parenting lesson was that if I were to look at what I know of Teddy Roosevelt in my research so far, I don't think he saw the challenge that his son was feeling.

I don't think he understood the stress his son felt simply by being Teddy Roosevelt's son, right, is a stressful—

and having the name Yeah, and he was so, uh, caught up in what he had to do for history, right? This is Ted—

which one? Senior.

Teddy Senior. Yeah, so caught up in what he had to do for history, he in some ways missed that his very own son was literally in a funk for, for several years because he could not figure out, could I ever live up to what my father was?

Could I be a bad father? Teddy Roosevelt Senior, he was not a bad father.

He was an absent father, right?

Which is very common.

Right.

I just said— I just had lunch with a friend of mine just, just this weekend who, you know, CEO, big company. And we talked about— he's got, you know, 3 kids, and he's a good dad and loves his kids, and his kids love him, you know, they're not angry at him. But he admits, you know, he was so focused on the company and the career that he probably wasn't around as much as he would have liked to have been. I mean, he can rationalize it to some degree.

They're—

his kids are hyper-independent, you know. They're very sort of self-sufficient, partially because they had to be.

Right.

He can rationalize that good or bad, they turned out okay. Yeah, I can see it in him. He's like trying to make the effort to like make up a little bit for lost time, you know.

And so this obviously occurred before the Teddy Roosevelt Project did, but understanding that problem, that challenge from most successful men who become fathers, you know, 13 years ago my wife and I sat down and we, we made a contract with each other that I would never be gone more than 3 nights in a calendar week. That may still sound like a lot to most people. Yeah, but doing what we do, you could be gone all the time. Yeah, if I were to accept all these opportunities— and so at the end of a third night when I'm on the road, my calendar goes red and nobody can add anything to it. Doesn't matter how great the opportunity might be, because I needed to be able to say no to things in order for my children to know the level of priority that I was trying to present.

Here's the thing I'm learning right, which is these communications happen in the time of peace, not in the time of anger, right? Because these conversations for most relationships happen—

now, I would love to tell you that this one happened in peace. It was actually during a window in which I was traveling too much. Okay, so, so I will be honest with you that the—

I appreciate it. Well, then let's, let's give the advice for those who are listening to this to make the conversation happen in a time of peace. It would be so much better, which is How many days is reasonable for me to be away? What does a business trip look like? What is the contract? And I love the fact that there's a contract. Like, what's the agreement, you know, that we have in this for this family? Because nobody lies on their deathbed and wishes they went on another business trip. But people regret the amount of time that they're away from their kids. And I've heard people rationalize it up the wazoo. You know, I do this hard work for you to preserve the lifestyle that we live, blah, blah, blah. I was like, well, give me a little less lifestyle and a little more parenting, and I'll take it every day, you know. By the way, I think that answer is complete bullshit. Yeah, you know, I think anybody who says that, it's a rationalization. It's their own ego who likes the lifestyle or likes the money that they can rationalize to their family. I do all this for you, you know.

Yeah, that's complete— by the way, buy me—

but you've never asked me if I even want the thing, right? It's like, look, I bought this sweater for you, Dad. I hate sweaters, you know. It's like, I don't wear sweaters, but I bought it for you. But I don't wear sweaters.

It's super nice.

Yeah, it's the most expensive sweater there is, Dad. I don't wear sweaters. Yeah, uh, you know, so I, I think that's largely a rationalization and a pile of shit, which by the way, just because, you know, this is how my mind works, is the same bullshit rationalization when short-term shareholder-focused leaders say, but I'm doing this to help provide jobs. I'm like, right, meh, not true, not true, because you're willing to lay people off at the drop of a hat, right? So if you cared so much about job creation, why don't you work tooth and nail to preserve jobs in hard times? So yeah, that's it's all rationalization to make us feel good about the fact that our values are misaligned.

To make our question—

It's to rationalize our misaligned values. That's exactly what it is. But what I like about this is, okay, align your values. And I love the idea of making a contract. I love the idea of making an agreement. If I think of some of the great leaders in business too, they kind of make that promise.

Yeah.

You know?

And you have to, you have to because everything shows up. I mean, everything is temporary, right? When it comes to our work and our success and our this and that. There will be a day when none of that will be on anybody else's radar screen but ours. Yeah. And then you got to wonder what's, what's left.

Are you the John Wooden to somebody?

So not every other month, but I do have a handful of people that I have intentionally agreed to mentor and spend time with. One of the challenges of telling that story of like, you know, having— is that then suddenly you get it, right? Is that suddenly get all these letters going, hey, you know what, I heard you tell the story and I'm looking for a mentor too. And so I tried to set some standards that I expect of people if they want to be in a mentoring relationship with me.

I had somebody walk up to me on the street and said some very nice things and likes my work, which I'm super grateful for. And then, you know, he says, this is my opportunity. I know I didn't think I'd ever get to meet you. Will you be my mentor? And this is my, my absolute honest opinion about mentorship, which is true mentorship. And let's define what mentor is. Right? I think we misunderstand, man, right? We think a mentor is somebody who's achieved something or done more than we have and we want to learn from them, right? You know, which is only partially true. A mentor is somebody who makes time for you.

Mm-hmm.

I have a mentor by the name of Ron Bruder, and when I first met Ron, somebody introduced us. I was pretty young in my journey, and somebody said, you guys will get along. And I didn't know who Ron was, and in typical Simon fashion, didn't look it up before I met him. Somebody said I should meet him. What more do I need, right? And so I show up for Ron's office being like, ooh, who's this guy, right? I figure I'd learn, you know, over the conversation who he is. And I literally sit down and Ron's in a three-piece suit and he's got a folder filled with stuff about me. And I'm like, I'm a goner, right?

Yeah.

And we had such a lovely time and he was so charming and so wonderful.

This is because you were a good storyteller.

Yeah, exactly right. So he's a good storyteller. He was just charming and lovely. And I remember a few weeks went by and like I had a question or something that was difficult that I didn't know the answer. And I knew, you know, based on my meeting with Ron, I'd been like, I bet he has a point of view. So I called his office and said, is he in? And he took my call. And a few weeks later, something else came up. And I thought, I wonder what Ron would think about this. And I called his office and he took my call. And then it became lunch, and then it became, you know, why don't you come to my house this weekend and hang out? And he became a dear mentor and a dear friend. And I remember I used the M-word for the first time, and I was getting ready to leave, and I was saying my goodbyes, and I put my arm around him as it was sideways as I was getting ready to go, and I'm like, you know, Ron, I'm so glad you're my mentor. And he said something I didn't expect. He said, and I'm so glad you're mine. It never occurred to me that Ron was learning as much from me, from the questions I asked, or from a completely different perspective, just because I'm considerably younger than he is, that he derived joy and learning from my time with him as well. And I realized that great mentor relationships aren't this sort of hierarchical mentor-mentee, that I'm wise and I bestow my, you know, my wisdom upon thee. That's not what it is. That the mentor shows up with equal excitement to learn and to teach, and that's why it's more of a mentor-mentor relationship, though the lessons are different, right?

So it's interesting you have that relationship with Ron, because that was exactly what Coach Wooden was, and that's exactly what he said to me. Yeah, he said, you know what, I derive energy, I take energy from you coming back and telling me what you did. I take energy from the— sometimes you're asking me questions, you're asking me to go back in my in my memory and, and think about things I haven't thought about in years. And by doing that, I leave these sessions— yeah— energized. And this is a 90-year-old guy. Yeah, right. And I love that because he did— he saw the same thing.

And that's what I said to this kid. I said to this kid, I said to him, I'm flattered, I'm grateful, but you couldn't go up to a stranger on the street and say, will you be my friend? It doesn't work that way. Friendships evolve. You can't just choose. I said, it's the same with a mentor relationship. You can't just go up to a stranger and say, will you be my mentor? It doesn't work that way. I don't know you. I said, I'm sure you're lovely, but that's not how it works. And all the mentor relationships that I have evolved, and I got to know someone and they became my mentor. I never said on day one, will you be, because it sets up an expectation of a sort of a transactional relationship. And I think the way I define mentor is a mentor always makes time for you. They always have time for you. No matter how busy they are, they have time for you like a friend. And, and mentorships, like friendships, evolve. Now, that's different than a mentorship program. And though I know the words are the same, it's not quite the same thing.

Yeah, I struggle with those.

And a mentor relationship is not a champion. You know, they have no control over your career. They can't put in a good word for your promotion. That's a champion. You should have champions as well. And occasionally those things overlap. But the best mentors are not even in your company. They may not even be in your industry. The only thing they care about is you.

You, right.

I think everybody has to have a mentor, and basically it's these friends that the friendship kind of takes on a bit more of a parental caring dynamic, not just let's go out and have a, have a, you know, have a good time and, you know, share a meal. They take on more of an I care about you dynamic.

The relationship with Coach Wooden, for me, I mentioned it was, you know, 12 years long. And about the 10th year, Coach looked at me and he said, Don, you know, you've written all these books, you've written books on this and that, but why have you never asked me to write a book? And I went, because I don't want to pollute our relationship. Like, I love what I get the chance to learn. I'm not here to profit from you. And he goes, but what if we wrote a book on mentorship? And so we did a book together that came out on his 99th birthday. Pretty cool. The first half of the book were 7 people who mentored him. But what was fascinating to me was he considered two of his mentors Mother Teresa and Abraham Lincoln, two people he never met, but he studied them so completely. He believed that mentorship doesn't mean we have to sit at a table. I can actually grow by studying you, by studying you, right? And if I can learn what you've been through and I can read what you've been through, I can consider you—

I can, I can take lessons from you, an active part of my growth. I love that. I have a friend who's obsessed with Marshall You know, and like if you go to his house, there's like books about Marshall everywhere. He's read all of them, you know, and there's quote books and just like from stupid little quote books to like sophisticated biographies. He's obsessed.

Yeah.

And you definitely get the sense that Marshall is mentoring him.

Yeah, he thinks as he's going through challenges, what would Marshall do, right?

What would Marshall think, right?

Yeah, yeah.

Not because he's going to copy it, but he wants to understand the perspectives and the point of view. Yeah, this is so interesting. I wonder if young people— I can ask my— I can ask the crew, do you have a mentor?

No.

Do you have a mentor? Kind of, sort of, in your definition. Yeah, you do. But you don't?

You've never asked Simon if he would be your mentor? What's up with that? Yeah, I know. Now you know what his answer is going to be.

So on, on our set, we've got young people on the, on the team. I wonder if it's a generational— like, you and I are, you know, old-timers here. Like, are— like, do young people, do your friends have what we would call mentors, which people who've gone through the trenches, know a little more, not peers, that make time for you and your friends to just guide you and help you along the way. Different than a parent, but I think the dynamic is like a parent. My mentors were like the two that I'm thinking of, Ron Bruder and Bob Chapman.

I would say not long term. I would say I had mentors in stints, but not, not anyone I would like.

And by the way, that's not bad. I, I actually think there are mentors who are meant to be part of your life for a season, not for a lifetime.

Yeah.

And there's nothing bad with having mentors for a season. Yeah. Now, I, I still think there's, there's deep value in finding that Ron, finding that coach, whatever it is, somebody who is long-term invested in you. But a mentor for a season is not a bad thing.

Do you have a mentor?

Industry-specific? Absolutely. I think that folks where that is more part, like if that is something that exists within their industry as well.

So, so, so they're, what they're saying is in industry specific, yes, that exists.

I'm thinking politics, I'm thinking corporate.

But I'm, I'm curious about your friends or like, cuz you don't have one.

Yeah, no, those, those are my friends, those pathways. Yes. But I would say for folks like me who come up in like maybe the more typical like gig economy, right?

Oh, of course, of course. There's so much more gig economy, right?

They're not—

I'm meeting young people more and more now who are taking very untraditional paths of career where they're sort of fashioning out their own careers, that they do a little bit of this, a little bit of that. Some of them may have a quote-unquote full-time job, but they've— everybody's got a side hustle, right? It's, it's a thing now.

You and I are like, our life is a side hustle.

I guess our life— that's the thing. But I think that's really interesting, which is when you have so many balls that you're juggling in this new young person's economy.

Yeah.

And, and let's be honest, I think there's a large amount of distrust of jobs because they've seen their friends, their parents, they get laid off, you know, it's not a meritocracy, right? Nothing personal, we didn't hit our profit goals, you know, you're out, you're out. That I think they're quite right to not trust the company or rely on the company, that now they're sort of fashioning their own independent paths. But the question is, does that make mentorship more difficult to find because you got 15 balls in the air, right? That's—

I think it, I think it is, because you're also trying to figure out who, who do I go turn to, right? What, what am I looking to learn?

Everybody's a little bit of a competitor, right?

What do I want to learn from somebody? Who would I naturally go hoping to learn from?

We see it exploited, right? We see that exploited online where there's these sort of like self-appointed gurus.

Oh, now life coaches, right? You can get— I've got a certificate in life coaching, I can be your mentor.

And some of those are good coaches and they get coaching certificates, but I know what you're going down. But I'm talking about the online content creators where they always have something to sell you at the end of their advice, you know, always have some program to sell you that's high price. And what they're selling is the vision of being taken care of. It's a little bit like a multi-level marketing scheme, you know, but without the garage full of vitamins, right?

You know.

But the— but there is sort of like the, the people who are profiting are the people at the top selling you quote-unquote mentorship. But they're playing on, I think, a lot of insecurities and desires. I wish I had this thing.

And we're—

and again, it violates my definition because we're relying on a stranger whose program is available to me, but they're not available, right? And that's not a mentor. That's just somebody who gives nice advice, right? Go ahead and consume people's advice online. I'm not against that.

They don't give nice advice. They sell nice—

they sell nice advice.

Right. And that's a— that's an important— that's also an important distinction.

And it's okay to have that in a cadre of my experiences and how I'm getting information, but it shouldn't be the only one, right? Like, I don't have a problem with people selling advice, but that's not your mentor, right?

No, don't—

that's just a program you took that helps you learn some skill, right? And if it worked, it worked. If it didn't, it didn't.

But let's not mistake that for mentorship.

That's not a mentorship anything.

No, you're right.

Mentorship is generous. Yes, mentorship is is, is a give. It's a servant leadership conception, right, to be a mentor.

Yes. I mean, there's— it's not transactional, right? There is nothing there. Um, I'm not gonna gain something by being your mentor.

There was never anything asked of me, and I, by the way, I never asked anything of them, right? You know, and no more than we would ask of our friends, right?

Yeah. No, it's, it's, it's been interesting. Coach Wooden has passed. Dale Brown, another basketball coach who's been a great mentor. I had great relationships with some of the people I've written books with who have actually stepped in and become somewhat mentor-like for me. It's fascinating to try to think about, um, but each one brings something different to me, and I frankly bring a little something different to them.

And as we get older, I think it's important for us to be mentors, right? Because as we've just said, to have those younger people in your life, they will— it's just like you and Wooden, and just like me and Ron, and me and Bob. Like, it's energizing for them and they were always grateful to me, which sort of never made sense to me, you know. And I think as you get older and maybe you're sort of mentored out of the game, like, because everybody older than you and more experienced than you is like, gosh, dead.

But it's interesting, but I think Coach Wooden was 99, and I asked him like, do you have mentors?

Absolutely. Well, he had Mother Teresa.

Well, but he also had— but he considered, you know, me a mentor.

That's what I'm saying, right? So make sure you mentor people But that mentor-mentor relationship, regardless of age, right, you learn something different. It keeps you young and fresh.

Yeah, he argued your job every day is to mentor someone and be mentored by someone every day. And he made that his responsibility, and he believed he did it from the time he was a high school basketball coach till the time he died at 99 and a half.

Look, you've written seminal books and articles about Wooden.

Other people have written about it, though, you know not as good as your work.

And other coaches like Wooden, you know, these winningmost coaches, none of them are obsessed with winning. You know, there's the same, the same thread, the same irony. Like the best CEOs with some of the highest performance, like Herb Keller from Southwest Airlines, Jim Senegal from, from Costco— like none of these guys were obsessed with the outcomes, with the numbers. They were all obsessed with the teams and the people, all of them, every single one of them. And yet they outperformed their competition over the course of time, right? With so much written Why are more people not doing it? Why are these leaders and these companies always the exceptions rather than the rules?

Right. No, I ask that question all the time. I think about coaching, especially because of my relationship in sports. We know that that is— that there's something to that, right? That the coaches who are invested in development and— am I going to make you better? Are you going to— are we going to be in relationship for a lifetime, or is this transactional? Is this going to end at the end of the season? The coaches who say, I want to be in your life for a lifetime, are the ones that win consistently, year in and year out. And yet, and yet, not everybody does it.

Why?

It makes no sense to me. It's a lot more work.

It is more work. It is also— so there's a story that David Marquet tells. He was a Navy captain, and he talks about how on his submarine there was one kid who was like the best at parking the submarine when they're in port. So every time they came to port, whether he was on shift or not, he parked the submarine. Why? Because he's the best submarine parker in the whole crew. And it occurred to Marquet at one point, like, what if he's sick, right? What if he's like on leave? Like, who's gonna park the sub? So he took somebody else to park the sub, and turns out he didn't do a good job. So I think when we do—

I wonder what that looks like, right?

I think when it's like, you know, if you ever scrape your, your wheels when you park on a curb, it's like that. It's like that, only it's 300 feet long, much more expensive to fix. Sharpie won't fix that one. I think this is what happens, which is in leaders in business, you know, we're like, oh, I'm gonna get that— the young kid a chance, I'm gonna get the new kid a chance, I'm gonna get the kid who's not the best on the team the chance, and they completely screw it up and you're like, never doing that again. And this is where I respect Marquès, which is the kid sucked at it, and instead of taking him off the controls, he had him do it again. And again and again and again. And turns out he was really good at parking the sub. Now he's got two guys who are great at parking subs, so then he gets a third, you know. And the idea of building a bench— and I think to your point, I think a lot of leaders are so driven by short-term results and short-term gains that they feel like they don't have the time to foster the talent or foster the skills in others, right? And so they just don't, which works for the short term until that person quits, leaves, gets sick, or the technology changes, or the culture changes, whatever changes, and you just don't have a bench. So you've got a team that can win a season, right? But you don't have a team that can win—

win both—

can win 10 in 12 years.

12 years, right? No, it's such a great point, but part of it is also what are the expectations that are—

that are, well, you know, Wall Street boards are like 'Oh my God, you better get me my bonus this year,' right? Nobody says, 'You better build the greatest company that ever existed over the course of the next 10 years.' Yeah. And it goes exactly to what we were saying before, which is if you catch people doing things right— if your goal is to drive this year, you're going to look for all the opportunities to drive this year, even though you know that there's a long-term liability that comes with it, right? But if your goal is to build something that's built to last, then you will.

Yeah.

We just had it this morning. I had a team meeting and We totally have a self-inflicted wound. Like, we completely screwed something up. It's all of our fault, you know. We succeed together, we fail together, right? And it was totally a self-inflicted wound. And like, we're— because the numbers dropped, there's a bit of a panic. Mm-hmm. We had to sort of like remind each other, it's like, hold on, hold on. You ever, you ever listen to air traffic control when there's an emergency on a plane, right? The pilots are calm, right? Because they know that panic, you make bad decisions. It's still, it's still dangerous, it's still bad, but stay calm. Go through the checklist, go through the priority list, and go do your work and like do a good job, but do it calmly. And sort of like we just reminded ourselves, like, we still have a fire to put out, but let's just do it calmly.

And let's recognize, right, that if we do it calmly, we're gonna be playing this game for years.

And I think that, and I think the only way you maintain calm like that is with an infinite mindset, because you recognize that this month is not the last month Right. It's not even the second to last month. It's just a month, you know.

Unfortunately, as you said, for so many places— Wall Street boards, whatever it is, boosters if you're in sports, presidents of universities, athletic directors— are saying, well, the guy down the street can win every year. Why, why can't you win every year? We give you resources.

I'll tell you a real-life story that just captures how when it goes sideways. A bunch of years ago, IBM missed its quarter. Right, and the CEO of IBM at the time made a video message to the whole company basically chastising the sales organization for completely screwing up the numbers this, this quarter, right? And like, I saw the video, it was an internal video, but it got leaked. Of course, I think the Wall Street Journal reported it, and I talked to people who worked at IBM. I said, hey, I saw the video, and they were literally like, whoo, glad I'm not in sales, because you're publicly humiliated by your CEO to the rest of your company because, because they screwed up the numbers. Right? If you pulled the lens back a little bit, it was the first quarter that they'd missed in something like 137 successful quarters, right? They missed one quarter, and the CEO's response was to yell and chastise and humiliate the sales team, right? How'd that work out? And if memory serves, not well. Like, the company then sort of didn't do well for a while because Now everybody's in a panic mode.

And my guess is the CEO is the— also paid the price. It's something, you know.

And the problem is, is like, at no point did anybody say, hey, I don't think that was the right response, right? You shouldn't have done that. Like, let's— like, like, where's— again, it's short-termism. Those are the pressures. Don, I could talk to you all day.

We could do this forever.

We should just start our own podcast. You're one of my favorite storytellers. What's one thing someone can apply today to be a better storyteller?

The biggest mistake most people make in storytelling is they don't know enough about who they're telling their story to. They don't invest in taking an opportunity like you with your mentor Ron. You showed up and thought it would be cool. You didn't do the research. If you take time to, to just do a little bit of work about who it is that you're going to get a chance to spend time with, who it is that you're going to get a chance to impact with a story, it will allow you to to make a slightly different tweak to the story that might allow it to be heard differently, might allow you to have greater impact. Know your audience. Know your audience, right?

Because you're not writing for yourself, you're writing for— you're writing a story for someone.

Correct.

That's brilliant. And when people— that's so good. Yeah, when people screw up narratives, it's because they're writing for themselves. They don't know who they're writing for, right?

It's a me story.

Yeah.

If it's a you story, yeah, it's a different story.

Great advice. Don Jaeger, what a treat.

Simon Sinek, what a treat. I'm honored just to be here.

So good. A Bit of Optimism is a production of The Optimism Company, lovingly produced by our team, Lindsay Garbenius, Phoebe Bradford, and Devin Johnson. Subscribe wherever you enjoy listening to podcasts, and if you want even more cool stuff, visit simonsinek.com. Thanks for listening. Take care of yourself. Take care of each other.