LMSM 10 | Career Regrets


Are you too hard on yourself? Do you ruminate on failures long after they’re over, or spend too much time fretting over the past? You’re not alone. In this episode, Ian Mathews and Frank Cava talk about how top performers tend to be overly critical of themselves, which leads to incredible results but also contributes to a regular feeling of emptiness. They talk about how to cut yourself a break and celebrate more small wins, rather than lamenting big losses, as well as how to lead high achievers who are much too hard on themselves.

Also in this episode:

  • How to help top performers who live and die with every small setback
  • The type of feedback that works best with a high achiever
  • How to pick the right context where you can stand out
  • Why you should be careful not to define yourself too early in your career
  • Regrets only happen when you stop trying to grow
  • Why you might be scared to reach your peak
  • No event will define your career
  • How no one is paying attention and why it is silly to worry about other’s opinions
  • Frank Sinatra’s famous words on regrets
  • A leader’s responsibility to celebrate often with their team

Watch the episode here

Listen to the podcast here

How To Overcome Career Regrets And Move On

“Regrets, We’ve Had A Few. But Then Again, Too Few To Mention.”

We are in the midst of the baseball playoffs now. We are going to kick this show off, which this entire show is going to be about regrets, how to deal with them, where they stem from, how they impact our motivation. We’re going to start with Hank Aaron. Anyone who is a fan of baseball, if you grew up in baseball and you pay attention to any statistics by any measure, Hank Aaron is a top-five baseball player of all time. Some stats on Hammerin’ Hank, one, you had to be living under a rock to not know that Hank Aaron broke Babe Ruth’s all-time home run record but outside of that, there’s a lot more. He’s the career baseball record leader in runs batted in. He had 2,297 extra-base hits, total base hits.

He’s top five career in hits, runs and 1 of only 4 players to have at least seventeen seasons with 150 or more hits. He made it to 21 consecutive All-Star games. He won a league MVP. There’s nothing on Hank Aaron’s resume. There’s no gap over a long period of time. He consistently was one of the best players in the league every single year. He garnered MVP votes in more than half of the seasons that he played in. The reason why we’re starting with all that and drilling home all of those statistics, he was asked after his career was over. This might’ve been around the time where he was getting enshrined into the Hall of Fame to summarize his career.

The first thing out of his mouth, not all of that stuff that he was proud of was, “I felt like there was something missing in my career. I felt like if I had done what I was supposed to do, I could have won at least 1 or 2 Triple Crowns and that would have been something.” I have different opinions when I think about that quote especially stacked onto the staggering accomplishments that he had in the sport. I’ll start with you and what you take away from Hammerin’ Hank having regrets in his career that he didn’t do as much as he should have.

The first thing I think about when you hear someone with those statistics and incredible bio lines is as a younger person, I would have said, “You probably need to be easier on yourself. You’re pushing yourself too hard.” If you do something especially in sports at a high level, I don’t think you ever get there unless you have a massive chip on your shoulder and there’s something that pushes and drives you. Most of the readers are probably not going to the gym to shoot 2,000 free throws. Most of us are business people who want to succeed or build a business.

If you want to have a statue erected with you swinging a baseball bat, you have to have this. I think back to something that is somewhat different. I think about my drive as a twenty-year-old versus as a 45-year-old and how hard I was on myself. You have to realize where happiness is and what we want to accomplish. You have to divorce yourself from being in the throws of it and pulling yourself to the side and saying, “What do I want out of this?” If you’re a major league baseball player, I don’t think you have that ability.

I’m slightly different with you on this. I find that the older I get, the more relaxed I am about things that I came up short on in my career. When I was younger, every failure seemed to be career-defining. When I say failure, I’m talking about like, “I missed my sales number this month.” Something like, “I forecast $400,000 in February and I only did $100,000. What a disaster. My career is over.” You regret it. You lock in on and you can get frozen on it. The older I got, the more I’ve realized, stuff like that doesn’t matter and no one remembers anyway. Small things I don’t remember. Is there a bigger record in all of the sports in Babe Ruth’s home run record? A statistical number. I’m not talking about championships or one that you would pop out more in your mind?

If you asked me, “What are the best records in sports?” I would probably go to wins. I would go to Wooden as a coach, Bill Russell or LeBron James or Michael Jordan, I would think about championships. That was one of the things I didn’t ask you but I was curious of. He said Triple Crown in that quote but was it championship? Is that what was missing for him or was it that he thinks that he can string something together well enough?

Triple Crown is another individual statistic. You lead the league in RBI’s home runs in batting average. It was a more individual piece of it. For me, at least, baseball is filled with statistics. We know that Babe Ruth had 61 home runs. You don’t know the highest points total ever, maybe other than Wilt Chamberlain who had 100 points. To me, the home run record is hollowed ground. That is someone who could beat Babe Ruth’s home run record because until that happened for 50 years, he was the home run king.

Usually, these things happen about every decade. That record was there for 40 or 50 years before Maris broke it.

When I look at this, this is a person who is incredibly hard on himself and has incredibly high expectations. I look at you don’t break a 50-year-old record from a legend by having low expectations of yourself. That’s not going to be an individual that seems to let things slide. I bet that was a guy who would look every day at every game and agonize over, “I can’t believe I took that second pitch. I should’ve hit that over the left-field fence.” It’s like, “To be excellent, you have to hone in on every little thing and you’re always iterating and trying to get a little better finding a little edge.” When I look at that quote, I think it’s consistent with greatness. I don’t think you could be like, “No, that’s about all.” I don’t think a person is wired like that. That doesn’t sound like Kobe Bryant or Jordan or people that we look up to that are hyper competitors with success. It’s consistent with the numbers he put up. That stuff doesn’t happen by accident or because you’re a freak athlete, which he was.

For a broader audience, there’s something that you have to think about. I don’t think Hank Aaron was great. I think he was either generational or iconic. Do you want to be iconic or do you want to be great? In the business world to be iconic, you’re Jack Welch. To be iconic, you are Steve Jobs but to be great, you can still be a millionaire and be great. You can still have an incredible life. You can still coach your Little League baseball team and tell your friends you’re retired even though you aren’t because that’s your goal. You were great. To be iconic, it’s something different. What I think about with about regrets, as a younger person, I would have felt like I was missing out.

LMSM 10 | Career Regrets

Career Regrets: A top performer tends to lose perspective because they’re so used to being good that their standard is different than everyone else’s.


I’d have regrets that I didn’t have regrets. I would read something about a sports figure and think, “I wish I had that passion. I wish I had that success. I wish that.” As an older person, when I look at it, it’s different. I look at it and say, “That person was able to harness these things and accomplish that great stuff. That’s beautiful. That’s like a piece of art. That’s like a Michelangelo.” It isn’t me. I get to pay $50 for a ticket. I get to sit and have a hotdog. I get to watch it because that is something magical and that should be celebrated but it’s different than I should hold myself to that standard, which is something that I would have beat myself up over it as a younger person.

I don’t know how to judge how hard Hank Aaron should be on himself because I played baseball. I wasn’t as good as Hank Aaron. I didn’t grow up with that kind of skill. When I look at his stats, I’m like, “I would’ve killed to have one at-bat in the Major League.” When I look at him, I’m like, “Take it easy. You’re a killer.” I don’t know what it’s like to have Hank Aaron’s body, hand-eye coordination, eyesight and skill. How can I judge how he should feel about what he accomplished?

As a younger person, if you bumped into Hank Aaron, would you feel compelled to tell him your opinion? As an older person, do you admire it?

If I’d run into Hank Aaron anytime I would have been speechless because he’s Hank Aaron and he’s godly to someone who grew up playing baseball. I look at that and think how in the world could I know to judge? I know how to look at it like this. When I was younger, I wouldn’t have known that only Hank Aaron knows how good Hank Aaron could be. Hank Aaron is like, “I left something on the table.” He knows how good he was and how much easier the game was to him than it was to other people. He knows what he could have accomplished whereas to an average player, they’d be like, “What the hell is wrong with you? You’re an icon.” He knew what he was capable of.

Let’s ground this in a way. As managers, if you come across someone who’s incredibly hard on themselves. Let’s say you have someone who works under you that is incredible and we both dealt with that, but they’re hard on themselves. As a seasoned manager, what do you do? Learning from what we learn from Hank Aaron, what do you do with that person?

Giving them perspective is important. Someone who is hard on themselves a lot of times are the top performers. They’re not paying attention to everyone else. They’re top performers because they come in every day and they focus like hell on what they need to do that day to be great. They’re not looking at other people. They talk to them but they don’t know how those other people feel. Perspective is helpful every once in a while to show them something like this. If my son is having a tough day in baseball. Let’s say he has a bad game. He goes over three, strikes out and he’s down on himself, I would show him a longer period of, “You had a tough game but let’s look at your last five games. Look how many hits you had, how many runs you knocked in and let’s look at your teammates, what they did over that time. Do you know how many people on this team would kill to have your last five games?”

Sometimes, it’s showing them a little more perspective because they’re stuck in the weeds and they can’t see the forest. Showing them that other people in their job would kill for their results or would love it to come as easy as it does for them. A top performer tends to lose perspective because they’re used to being good, that their standard is different than everyone else’s and that’s the only standard they’re looking to live up to.

That’s what I wanted to dive into a bit. Let’s say you have someone, they don’t want to be 7th out of 300. They want to be number one. They’ve got the chops and the ability. What I have noticed in some instances is this, it’s important for you to help them with everything you said, remind them, show them, make it relevant. The other thing is this, I can see inside of you that you do not want me to hold you to anything else other than the standard that you want to hold yourself which has to be the absolute best. I think you can do it.

I don’t think you should drive yourself nuts. I think you’re going to be better and faster if you round off those edges and you’re not hard on yourself. When you’re having an average month, realize there’s another month behind it and then stack those things. Round off the bottom edges, don’t have those times or months or at-bats where you bought them out. That’s when your greatness can come through. That to me is critical because it’s rare that you find someone who’s incredible. When you find someone who’s incredible, I don’t want to perjure them with my opinion of what they’re capable of.

I’m going to give you a quick example of this. This is important for a high achiever, top performer. At GE, when I started in my sales account package, I was like 112 out of 112. I was dead last. I had almost no orders. They gave me a crappy account package. In two years, I got up into the top twenty but I was that guy that was nineteenth and Mac was one and it drove me nuts. I was like, “This sucks. I’m a loser. I’m not as good as him.” In two years, I had passed 100 people. My boss was like, “Give yourself a break. It’s unreal what you’ve done, look how far you’ve come.”

I didn’t want to hear that shit. I wanted to be one. I would be like, “I’m not looking for you to soft-pedal this. Look me in the eyes and tell me why I’m not one. I don’t want to feel good about being nineteenth. I’m not wired that way. I want to know what it takes to be one.” He was like, “Do you want to know? You waste too much time on small accounts. You love your little accounts. You love prospecting. You love running around to small customers that can give you $50,000 at a time but that’s a waste of time. Mac has three huge accounts and he is deep. He goes and gets $1 million and $2 million deals. You don’t ever close those. You do it by running around and you’ll never be Mac.” It was cut through the bullshit.

People who do incredibly well in their careers and make a lot of money are not afraid to be beginners all the time. Click To Tweet

He was like, “You’re not in BPM account. You’re not an ExxonMobil.” He named five huge accounts. He knew we’re in Chicago. He’s like, “They spend more than your whole account package together and you avoid them because it’s more work and you’d rather go close your little ones.” I was like, “That’s what I need to hear. Thanks. I want to be one. You gave me some biting criticism of what number one was doing that I wasn’t. I’m willing to do it.”

Take Kobe Bryant. He is the seventh-best player and he was asked a coach, “How do I be one?” It would be like, “Here’s what Jordan does. He gets into the gym at 4:00 in the morning.” Kobe Bryant would be like, “I’ll be there at 3:30.” That’s who he is but he might need that feedback of, “Here’s something that you can control, that you should do that can get you to where you want to go.” Instead of soft-pedalling, trying to make me feel good about not being one. If that’s all I care about is being number one, someone who’s a high-achiever like that wants to hear the path. “If you want to know it, here’s what it takes.”

Like you, I can’t judge Hank Aaron. We can’t tell him how he should feel. We can’t tell a top performer how they should react. At that moment that GE manager told you, “Do these things if you want to be number one.” They gave you the tools and then it’s up to you to then turn that into something. You were still having a fine career. As a manager, you need to listen to what your employee wants and give it to them. If they do want to hold themselves to that high caliber, don’t pull them back, give them the tools.

There are going to be plenty of people that are proud of being top 20 out of 120. If you’re a career salesperson, that wasn’t me at that time. I didn’t want to be a career salesperson. The top twenty are making money, doing great and they’re happy with that. For me, I didn’t want to be told nineteen was fine. Don’t tell me that crap. Tell me how I can get to the next level. That’s what I want. Those are the best people to challenge and manage. My manager was good at reminding me of where Mac was every month because he knew it would get me to work a little harder and think a little different.

We’re getting to the end of the Hank Aaron here. We’re going to move on to something else but I want to tell a brief story. I’m a part of a mastermind group and now I’m in the leadership team of this mastermind group. When I first started this mastermind group, I was a paying member. I was a young kid in the mastermind. There was a guy in that mastermind who was on the founding team of Kodak. Rich is how did fine. He had three sons who all wanted to be professional basketball players. This guy had retired early. He went to practice and got to watch all the practices and saw the stuff. He sat down with his sons and one of them was talented.

The kid thought he wanted to play in the NBA and the father was encouraging him, never said a word. His son came up to him sometime after high school, he had offers and he goes, “Dad, I don’t think I want to play in the NBA. I think I want to be in business.” The dad goes, “Are you sure?” He said, “Yeah, I’m sure.” He goes, “Are you positive?” He goes, “Yeah, I’m positive.” He goes, “I can’t change your mind?” He goes, “No.” He goes, “Can I give you my opinion?” The son said, “Sure, I think it’s a great decision.”

He goes, “Do you know how good you have to be the twelfth person on the bench of an NBA team? Now we’re in Europe, in Asia and they find people in Africa, you’ve got to be 300 on 7 billion, which is a hard life. Do you know what it takes to be a millionaire in business? The margin is greater.” As you’re reading this, if you’re young, you’re trying to pick your career path or you’re trying to pick, “Do I become a startup owner or one of these things?” You can build one hell of an incredible life without being Hank Aaron. There are a lot of happy landing places in the middle there. If you do want greatness, that’s great too but there are also a lot of great spots that are off-ramps between here and there.

Let’s go back to that 300 out of 7 billion people. If you want to be top 10% earners in this country or making three $350,000 to $400,000. That’s 30 million people in America are making $400,000. You’re trying to get into the 30 million. That’s not anywhere near as difficult as playing a professional sport. It’s not that difficult if you put the energy, if you put the time in, that’s not a real big number. I love that piece of it. Moving off from sports. We are talking about regrets. Leonardo da Vinci and Michelangelo lived around the same time during the Renaissance, both genius-level intellects by far. If you’ve ever seen any of their work up close, it’s outrageous that humans could build what they did without machines.

Especially some of the sculptures. Leonardo is interesting. He’s a hard guy to define. He was a great artist. You could call him a scientist, a mathematician, an engineer. He was an inventor, painter, sculptor. Mona Lisa? Yes, incredible. He invented scissors and parachutes. He came up with a glider decades before anyone built a real flying machine and it was close to what ultimately worked. He didn’t have time to jump off a cliff. He invented a tank hundreds of years before a real tank was built because there was no combustion engine when he was around but he came up with the idea of it.

He has work in human anatomy. It was crazy, all the kind of stuff that Leonardo da Vinci was in to make the world a better place. On his death bed, he’s quoted as saying, “I’ve offended God by not working more on my art as I should have done.” He confided with his assistant at the time that, “I have this gift.” What we’ve learned from then is he had an incredible mental capacity that I can’t even comprehend. At that time art was valued more than about all the other stuff he worked on. He had this gift and art during the Renaissance and he spent a lot of time on all these other little pet projects that in his mind, “I could have done more sculptures. I could’ve done more paintings,” because everything he did was incredible, like the Mona Lisa. He felt like he wasted it. When you hear and you think about da Vinci and you hear a quote like that, how does that make you think about your career or other’s careers?

It’s like we talked about with Hank Aaron. The first thing I realized as a 45-year-old is I can’t understand what he was thinking like and what a tormented place. Speaking of not having regrets, I’m thrilled that I don’t feel that way but people aren’t going to travel to Richmond, Virginia 500 years from now and see what I’ve done with my life like, “I’m going to go away and going to be gone.” There’s a torment that comes into greatness in art. That’s the thing I think about. It’s unrelatable. If you could wish anything for Leonardo, what would it be? It’s to show the sheer joy that five centuries later, his tinkerings, how close he was but that’s the part of it. It’s tormenting.

LMSM 10 | Career Regrets

Career Regrets: Aiming for greatness is great, but there a lot of happy landing places in the middle, too.


Michelangelo was the same. Michelangelo focused a lot more on his sculptures but it’s famous that he was forced into doing the Sistine Chapel and he hated every minute of it. It wasn’t that laying on your back for hours a day, sweating. The Sistine Chapel would be a miserable project to do. I don’t even like to paint a fence, to have to paint that ceiling. It’s incredible but he thought he wasted three years of his life doing the Sistine Chapel. It took away from doing more projects like David, which is what he thought his real calling was.

Sistine Chapel, probably six or a half-dozen from David on most famous things he’s done. It’s incredible if you’ve ever seen it. While he was doing it, he was tortured and he thought he was wasting time. One thing I take away from this because I think a lot of people get an occupation early. What did you do first out of Florida? You build houses. You’re a project manager. How many people start building houses as a project manager and five years later, they’re still building houses and they’ve defined themselves or don’t think there’s anything else in the rest of their career?

I’m glad you’re going this way with it because being Hank Aaron or Michaelangelo or Leonardo is abstract but this is where we can control our destiny. I remember coming out of the University of Florida, had a degree in Construction Management, which is a cross between Architecture and Civil Engineering. I saw a few things in interviewing with companies. If you worked at a commercial construction company, I thought you were arrogant, not a great communicator, your hours sounded miserable and there’s no way I’m going to have any fun doing that. I remember looking at different home builders. I looked at a couple of home builders. I went to Ryan Homes in Northern Virginia and they promoted a work-life balance. They promoted, “We hire people with no construction experience.”

They talk about, “If you’re good at this, there’s a ladder and you can progress.” I went to a company in South Florida, which is where I lived and it was 6:00 on Saturday and the office was 60% full. All I could think was, “If I’m going to get ahead of these people, I’ve got to work Sunday too.” What I remember being at 22 and 23 was honest. I’m not good enough or I don’t want that life. That looks miserable. What I want to do is I want to be able to dictate and I want to stand out. They’re never going to erect a statue for me. I’ve come to terms with that. The things that I could do, I knew that if I put myself in the right place, I could do well, have a life I liked and build something that I wanted. I couldn’t articulate it when I was in my twenties like I can now but I knew what to avoid. That’s the things that I think these poor guys that are geniuses can’t.

They have regrets because they didn’t focus on one thing. The common knowledge there is become a blacksmith, get good at it. Blacksmiths your whole life then teach your kid to do that occupation. That’s how things worked them. That mentality is still there. We worked for the same home builder but I worked in the mortgage industry. You have no idea how many people that were like, “You can’t get out. Once you’re in the mortgage, you’re in the mortgage.” The reason is it pays well. You don’t run into a lot of people that find joy in being in mortgages or financing or in building houses. They defined themselves early. They were beginners once but they didn’t want to be beginners the rest of their career.

I find that people that do incredibly well in their careers that make a lot of money are not afraid to be beginners all the time. That doesn’t mean you have to start a company but you’re willing to learn. The people that made the most money even in big companies were project managers and they were like, “I want to learn sales. I want to learn about marketing. I want to learn finance. I’ll be an analyst. I’ll go do that.” They were always thinking about being more well-rounded and then they could add more value to that organization. It’s the same if you’re not in a big company. You are still a builder. You could still build a project manager house all by yourself without anyone on your team.

You’ve not lost that. That’s not something you do on a regular basis anymore. You wouldn’t let yourself become defined as that. You were a project manager, I’m this, I’m a manager, I’m good at finance, I’m good at lending money and I’m an executive coach. You kept saying ‘and’ throughout your career. The more you can say ‘and’ and stack skills, the more money you can make, the more your career goes. If you limit yourself and say, “I’m just a medical sales rep.” That’s all you’re ever going to be but you could be a sales rep and something else. A lot of people stop at that. They think they have to define themselves early.

People that I know that are the happiest feel like they have free will and people that I know that are the least happy, feel like they do not. It’s the perception on both sides of it. You and I are different about what we worry about, how we handle things, how we reflect. One thing we’ve always done is we’ve taken control of our lives, our careers and we’ve always wanted to be striving for something else. We wanted to get into a role, do great with it but we were always willing to go to the next role or try something new even though we knew we could be colossal failures. I quit a lucrative job to build this business. For 5 to 7 years, I felt like a colossal failure like, “What a huge mistake.”

On the other end of it, I felt challenged, pushed, alive while I was doing it. When I got to the other side, the reward was incredible. There’s an honesty to it. The way that I look at life is being born when we were being born. It’s different than being born in the 1300s or 1400s like these two guys. Apprenticeships are gone. The speed of implementation is faster. You get to pick. That’s the whole point of what we’re talking about here is you get to set your own arc and if you are going along a path long enough and it makes you unhappy, it’s time that you’re honest about it and you change. It’s up to you to do it because no one else is going to do it for you.

If the people in my network that knew me and you’d ask them, “What’s he like in 2003?” They’d be like, “He’s an industrial equipment salesman.” Does anyone who knows me think of me that way? That’s who I was at that time. “He’s an industrial sales guy. He’s really good at it too. He sells some engineered stuff.”

I want to jump in right here and say this, who gives one shit what other people think of you? It’s up to you to think about what it is about you. Hank Aaron doesn’t care what we think of him. Leonardo and Michelangelo are long since dead but the point is most people in life are fucking miserable. “I don’t care what you think of me. It’s my life, not yours. I have little hurdles in front of me that I set.” When people ask me, “What do you regret?” They’re few. If I’m being incredibly honest, it’s few. If you said, “Frank, come up with five regrets,” I can’t come up with five because everything that’s happened in my life, I’ve turned into something better. Why we’re both on the other side of this thing looking back at it, talking about it is because it’s a mindset and it’s not going to define me. I’m going to get better and it’s going to be something that’ll spring forth. Who knows what’ll come around that next corner because of that setback?

Happiness usually comes down to enjoying the process and the grind. Click To Tweet

It’s fascinating how much people struggle to think that we are capable of anything we want. Even within the first six months after leaving NVR, I’d have people saying like, “What would you do next? You’re going to be a president of a mortgage company for another builder?” I’d be like, “I’m never going to work in that space again.” My saying is the same as you used to tell people, “My goal is not to ever put a suit on and interview again the rest of my life.” It was like, “I’ve done that. What’s the next chapter?” That’s not defining me. That’s not going to be every chapter of my life. That was one chapter in my life. I learned a lot. I had fun. It’s something I grew from. I’m ready to learn something else to be a beginner again.

I feel this way, I don’t think you have to have the aspirations that you and I have, to quit jobs, build businesses, become an author like Ian is. You don’t have to do that but you need to feel like you’re growing. If you feel like you’re not growing, even if you never progressed past. My mom was a school teacher her whole career. She always felt like she was making a difference, like she was growing, she was getting better and she’s the happiest person I’ve ever met in my life. It doesn’t matter how you corral that. To me, it comes down with regrets have a lot to do with not growing. It’s up to you to figure out how to do that inside of your life, your career. That’s what it is.

Moving onto our next example. Princess Leia and Han Solo, we’re going to talk about. Carrie Fisher played Princess Leia. She was nineteen years old when she took that part and new in her career. We’ll talk about defining yourself by one thing. She took that iconic role. We were introduced to Carrie Fisher with buns on the side of her head as a princess. Star Wars blew up and we got more of the princess in Empire Strikes Back and then Return of the Jedi. That’s what she did. That’s how she was known on that circuit for years. She was quoted years later somewhere in her 60s on a TV show. It was, “If I had known how popular Star Wars would have been, I would never have done it. All I did when I was famous was wait for it to end.”

You think about that and you can relate to it in one aspect. Once you are defined in the public eye, as something. She was defined as Princess Leia. It makes it hard for people to see you as anything else. It makes it hard for someone to take you seriously in a different role because all they can see you as is having those buns on the side of your head. What’s fascinating is why didn’t that happen to Harrison Ford? Harrison Ford for five years, same as Carrie Fisher was Han Solo. What else did Harrison Ford do? He was Indiana Jones. He did the Fugitive, Blade Runner and he was many other iconic characters that didn’t seem to hold him back. You don’t hear Harrison Ford saying, “I wish I wouldn’t have done it because it held my career back.” He went and did the next thing. What I get from that is being defined at a certain point in your career, that’s your mindset. That’s not someone else’s.

We were going to talk about some fun stuff with this. I’m a nerd for Star Wars and I love it. Star Wars 3, 4, 5 and 6, the originals and then there were the prequels. They dusted Carrie Fisher off and they brought her back. She made that quote somewhere between the height of the stuff in the late ‘70s, early ‘80s and in the 2010s when they rebooted it. It comes back to this. Harrison Ford had higher self-confidence. Maybe it was justified, maybe it wasn’t, maybe he was more talented. I don’t know the answer but do you know what The Peter Principle is? Can you explain it succinctly?

The Peter Principle was a satire book. It was meant to be a joke. It was a book written about a guy who had noticed a phenomenon in business and that people get promoted until they reach a certain level that they shouldn’t have been promoted to. It becomes clear to everyone that they’ve reached too far. The Peter Principle in essence means there is a certain level everyone can attain and that’s it. It’s largely satire. If you look around most companies, you find it, people get promoted, they’re a supervisor then they’re an office manager then they’re a district manager, they get to regional and they blow up. It doesn’t work there. Their intelligence isn’t there, their skillset doesn’t fit anymore. The Peter Principle is there’s a level everyone reaches that was one step too far.

Let’s go back to Star Wars, their Peter Principle was Luke and Leia. The best they could get, they got cast young. They had a superstar concept, movie producer, everything and they get elevated. Harrison Ford was way better than Han Solo even though he was incredible as Han Solo. He was in American Graffiti before he was ever in Star Wars. He was already a star. He was the one-star. He looked at it and said, “This will not define me. I’m better than this.” He pushed past it. If you look at Carrie Fisher, she also had a huge drug problem in the ‘80s. She got into the hype and didn’t push yourself past it and allowed the Peter Principle to stall her. Mark Hamill is an awesome actor in that series.

Most of the stuff he does is voice acting. He’s a voice actor. He had this one thing. This is what I hate about the human psyche. Instead of looking at it and going, “Holy shit, what a ride I’m on.” You don’t like it, hate it and want it to end. It ends and twenty years go by and you look back and say, “I wish I had that again.” That’s where doubt and unhappiness come from. One of the things that Ian and I talk about a lot, I was raised in a different way than Ian. I’m not this way nearly as much now but in my 20s and 30s, for sure. I used to be incredibly fit. I had abs and I have not had abs in decades. I would look at someone with abs many years ago and I’d be like, “Look how fit that person is.” Ian would be like, “Who cares? He’s going to go home and have ramen. You and I are eating steak.” He celebrated that. That was one of the reasons we became such good friends. We had different perspectives on the same thing. Carrie Fisher had this rocket ride and she didn’t enjoy it. That sucks because it’s over.

It’s the reason why there are more one-hit wonders than there are rolling. When you have success early in your life, it’s easy to say, “I don’t think it can get better than this.” That only happened to me one time in my life and that was right when I left NVR because there was a big payout. It was easy for me and my mind to be like, “Did I hit the top of the mountain?” You have to fight that. You have to in your mind say, “Be happy, embrace it. That’s incredible accomplishment.” Money shouldn’t be the peak. You should always be thinking of the peak as the next accomplishment something you’re proud of because there are some things I’ve done since that have nothing to do with the money, that I’m more proud of than that money than whatever I walked away and cashed out of.

I’ve got some things ahead of me now that I’m way more excited about than what I did in big companies. I had to fight that. Most people have to fight it too. Especially if you have success early. Carrie Fisher was thirteen years younger than Harrison Ford when she did that. Do you think it’s a confidence situation that Harrison Ford had done other things and he knew he could do them again? This was a stop. He had more confidence than she did. She thought, “In nineteen, I’m on every billboard around the world.” Do you think that’s it or she thought, “I can’t possibly beat this?” Whereas then he was like, “Whatever.”

You had talked about one-hit wonders. I don’t know what it is for Carrie Fisher. I don’t have a good enough history of her life but I can tell you this. One of the things that I have noticed with happiness is it usually comes down to enjoying the process and the grind. Harrison Ford had more grind to him than Carrie Fisher did it. Maybe he was older or something else. One of my favorite artists is Tom Petty. One of my favorite songs by Tom Petty is a song called Into The Great Wide Open and it’s a story. In that story, this couple finds random success. He becomes a one-hit-wonder and starts to party. He puts out a second album while he’s partying and loving life. There’s a line in there that says, “Their A&R man said, ‘I don’t hear a single.’” They hadn’t even realized it but it was over. You too, like them, dislike them, they grind.

LMSM 10 | Career Regrets

Career Regrets: Regrets have a lot to do with not growing. It’s up to you to figure out how to do that inside of your life.


Every album takes 3 or 4 years. There’s a process. It’s repeatable. It goes on over and over. I can tell you that I think Harrison Ford had better chops. He knew he had better chops but he also enjoyed the process, got into the process, could get into roles better. He was believable. When Harrison Ford was Indiana Jones, I did not think Chubasco was going to show up but whenever I saw Carrie Fisher and something else, I wonder when she was going to come in with the buns in her hair. She couldn’t compel me the same way.

I don’t think that’s a skill. That was a mindset that got stuck in that, “I’ve reached the top. I can’t do better. That’s who I am.” She let it define her. Instead of breaking through that mindset and trying different things because a lot of people can do that. Her destiny was not set until she made her mind up that it was.

I don’t disagree with that but it’s like we started off with Hank Aaron. There’s a grinding process to this and there is a holding yourself accountable piece. We don’t know her but for the readers, you want to build a career. You want to build a business. Hank Aaron had a lot of process behind what he did. What I see with this particular example of Carrie Fisher and Harrison Ford, to me, Harrison Ford was more talented. I don’t know if it was God-given or if it was a belief or if it was a process but it’s probably some combination of all three of those. That’s what propelled them forward in my opinion.

We started to get into it a little bit. I’ve known you now for over a decade. You and I are wired a little different. The question I want to dig into a little bit more here is the capacity to move on, the ability, which is a skill. The ability to drop what’s happened in the past, learn from it a little bit but move on, don’t emotionally dwell. To move on from failures or mistakes or things that you could have done better, do you believe that’s a learned skill or is that an inherent talent that we’re born with?

I think you’re born with something and you’re built with that in how you’re raised. My parents are both warriors, perfectionists, and people who have accomplished but have accomplished to a point. With growth comes the ability to realize the good and bad that you’ve seen in life and being able to grow past it. You talked about blacksmiths and apprenticeship, that’s the beauty of being alive in the 21st century. We’ve got YouTube, we’ve got training videos. If you want to figure something out that you think that you want to change, you can. You can vehemently argue either side of that and you could put together a winning argument but it comes down to choices.

Part of the reason why I asked this is in the time I’ve known you, you’ve grown a ton in this area. You used to strike me as a big-time warrior and someone who overly focused on the opinions of others. A lot of times it was imagined opinions of others. It wasn’t even you were stressing about something someone said or did, it was what they might perceive of you or what they might think about how something happened. I bring this up because I’ve seen you become a different person. Is that you needed more notches on your belt or you needed more successes? Is that you got a little older and more mature and you grew?

When did you see it? I’m curious what you think the catapult was. How did you see it change?

I saw you like that at NVR. I saw you that after NVR for 5 or 6 years. It’s not been a long time that I’ve felt, “Frank doesn’t dwell much on anything anymore. He moves to whatever’s next.” It has been a short period of time in the time I’ve known you that you’ve not been much of a dweller.

You were talking about your sales career and a little bit about your results. You said something about, “No one cares anyway.” I don’t know where the shift happened but the shift happened for me that people don’t give a shit about me, people care about themselves. People don’t realize what I’m doing or not doing. All they care about is what’s happening or not happening for them. When I figured that out, I realized, “There’s a lot of freedom and space out here that I don’t have to worry about this crap.” There are a handful of moments that got me there.

This is the rabbit hole. I built a house during the last recession, the person who bought it for me, the septic system failed and they ginned up a lawsuit. They sued me for $15 million and I thought I was going to die. I did not know how I was going to get through it. I felt like a terrible, insignificant human who didn’t deserve to live for a period of time. I was fucking miserable. My wife says I went through a period of depression and I don’t like to use that term but I think I did and I didn’t get help. I’m a meathead. I tried to figure it out. When I figured out that, “Screw this. If there was a mistake, I did everything I could to rectify it.” Not only that, I paid for it. It costs me over $1 million. On the other side of that, I said, “That wasn’t enjoyable.” I got my sense of smell back. I got my sense of feeling back and in the end, nobody gave a shit about the fact that I went through that.

No one knew.

No one cares about your regrets. Move on. Click To Tweet

Even people who did didn’t show up with envelopes of cash or put their arms around me. It was quiet. It was one of those things where you realize, even when something is public or private, it comes down to you and how you interpret it. Getting to the other side of that gave me the ability to say, “Mistakes are going to happen. They don’t define you, build a moat, figure out how to be strong. At the same time, let it bounce off you because the more resilient you are to crap, the better you’re going to be prepared to go further.” That’s what it was for me.

I got a funny anecdote on this. When I left NVR and semi-retired, I tried to figure out what I was going to do. I didn’t have an office to go to anymore. I’ve been going to an office for twenty years with 1 of 2 companies. I knew my routine and I thought everyone in my neighborhood knows that Ian leaves at 6:00 in the morning and leaves when it’s dark and comes back when it’s dark. I told my wife, “I’ve got to go somewhere. I’ve got to go to a coffee shop. I don’t want the neighbors to ask, ‘Why is Ian’s trucks in the driveway all the time?’”

She was like, “Do you think they’re paying attention? Do they give a shit about your truck? I bet they won’t even notice.” I’m like, “They’ll notice.” This is three months later. The first month I went to a coffee shop every day. For two months I worked out of the house. My truck was there all the time. I hadn’t talked to any of the neighbors in winter. It was like January, February, March and none of us come out. We hang out in the summer. This was like April. I brought it up to one of them and they’re like, “You left NVR?” It was four months later.

They didn’t notice that my truck was there all day. They didn’t notice that I wasn’t going to my office in Reston every day. They didn’t give a shit. They had their own problems with their business. It goes to show to your point, people care about themselves. They’re not thinking about you as much as you think they’re thinking about you. You’re not significant to anybody. Especially the people that you’re normally worried about their opinions, you’re not significant to them. There aren’t people out there actively rooting against you and following everything you do. That’s made up in your mind. It’s not even real.

Do I wish I had the body I did in my twenties or wish my knees didn’t hurt or wish I could run as fast? Yeah. Would I trade where I am now for that? No. The reason is there is peace and an ability to think and enjoy. If I’m ever harsh on myself, I think about things I might’ve missed because I was stuck in my own head. How many great things did I miss because I was worried about other crap? There are tons of it. I’m married, you’re married. We have kids. Being a dad and a husband is hard. If you focus on the parts that suck, it’s awful. You’re going to drink. If you focus on those couple of laughs you get or when your wife puts her arm around you and says, “You’re a great dad. Thank you.” Those are the moments that propel you. You have to forget about the crap and realize it.

You’ve got to embrace them. You’ve got to enjoy it. You’ve got to remind yourself. We both love Frank Sinatra and his My Way got a classic line which is, “Regrets I’ve had a few but then again too few to mention.” It’s one of my favorite song lyrics ever. I love it. It gives me perspective every time I hear it. One, the fact that he’s saying, “Too few to mention,” he’s saying it’s not worth me thinking about it but he’s also saying, “I’m not going to mention it because you wouldn’t give a shit about my regrets.” No one else cares. No one cares about your complaints, your gripes, your regrets, anything. I’m not going to even mention it because I’m doing it my way anyway.

That’s a great perspective. I remember being in high school and being stressed out in the state playoffs and telling my dad I was stressed out and he was like, “Do you have any idea how much I would love to be on that field tomorrow in the batter’s box one more time? You go up there with a smile on your face.” I remember every bat after that, I had a big ass shit-eating grin on my face. “I’m in the state playoffs. This is amazing.” It was one of the best streaks I was on. I was hitting the ball well because I was not in my head. I was trying to enjoy every moment. I do that now when I coach.

I do that now if I’m stressed about lineups or something’s going on in baseball, I’ll be like, “Get out of here and have some fun. Embrace being out here with your son and his friends and enjoy the hell out of it.” Everyone you talk to who has ever coached youth sports, whose kids have grown up will tell you, “You embrace it. Those are some of the best days of my life.” Your quote always that you say to Max is what?

“These are the good old days.”

Cat’s in the cradle and it’s easy to look back and miss everything because you’re focused on the bullshit when the truth is these are the good old days. Every day is the good old days. You embrace the fun like you and I are embracing doing a crappy nascent show which one day may or may not become something important but we got to enjoy it. It’s fun. You’ve got to enjoy things.

What I think about at this moment is this, if you’re not enjoying stuff, you need to. In addition to that, if you’re ever a manager of other people, the best thing you can do is remind them of the little thing. Everybody worries about what do other people think of them, even though you say you don’t but if you pick up little things on people and you compliment them or tell them it’s a great job, you never know how far that’s going to go. We do a team call-in and Fridays are longer days. We do a fun team activity and we’ve got parts of our business that were broken, that are great. What I’ll do from time to time is link a few things together and say, “This department was broken, this wasn’t happening. We’ve got a bunch of service tickets.”

LMSM 10 | Career Regrets

Career Regrets: With growth comes the inability to move past the good and bad that you’ve seen in life.


Let me show you why this happened. We hired Vince, who’s our head hunter. He went out and recruited these seven people. Those seven people went into this system that we had built but it wasn’t great. Now that we’ve added a few people, everybody in that system is better because Vince found them. Derek came in and we need to celebrate the fact that we had 40 work tickets in the system before and now we’re at two. It’s an awesome job.

I’m going to end this episode by saying that I brought my two-month-old puppy into the office to do this show. In the time we’ve been talking, I want some kudos from you now. I have not let you know that he pissed. There is a big log of crap on the carpet in my office, which is small, smells like puppy poop. I didn’t even blink. I’m not going to have any regrets for bringing this dog in because there’s got to be a lesson that I learned in this puppy in here who’s been pooping and peeing all over. God bless her. She’s been sitting here listening to you and I ramble. She’s like, “I’ve got to go. You’re not going to shut up and take me out. I’m doing alive. I’m going right here.”

Do you know why you have no regrets? You rent.

It was good to see you, Frank.

It was good talking.

No regrets. I’ll see you.

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