in: Behavior, Character, Podcast

• Last updated: September 28, 2021

Podcast #108: The Upside of Your Dark Side With Todd Kashdan

You can’t go anywhere these days without running into an article or a book on how to be more positive and upbeat. Pessimism and anger are seen as traits we should do all we can to avoid. But my guest today says that view might be a little too narrow and short-sighted. His name is Dr. Todd Kashdan, and he’s the co-author of the book, The Upside of Your Dark Side. Today on the podcast we talk about the benefits of getting in touch with your so-called “negative” emotions and the potential downsides of too much positivity. This podcast dovetails nicely with our recent series on depression, but it’s about much more than melancholy.

Show Highlights

  • The rise of “happiness fascism”
  • How positivity can make us stupid
  • Why our pursuit of comfort and happiness is making us more miserable
  • The benefits of anxiety and depression
  • How to make anger productive
  • Why mindlessness is great
  • What Teddy Roosevelt can teach us about the benefits of narcissism and psychopathy
  • How to be better managers of our different emotions so we can get the benefits of both the positive and negative
  • And much more!

Book cover, the upside of your dark side by Todd Kashdan.

The Upside of Your Dark Side is a great read. Engaging, entertaining, and actionable. It provides a much needed nuanced look at our emotions. I highly recommend it.

Special thanks to Keelan O’Hara for editing the podcast!


Brett: Brett McKay here, and welcome to another edition of The Art of Manliness podcast. Anywhere you go today, there seems like there’s a book or a magazine article or a blog post on 10 Ways to Be Happy, The Benefits of Happiness, Why You Need to be Mindful, Why You Shouldn’t Get Angry, yada yada yada. I mean it’s basically an article of faith in 21st century America that you need to be happy all the time or something’s wrong with you. Our guest today wrote a book along with a few other guys who say that’s not necessarily true, that there could be some downsides to positivity all the time, and there’s downsides to not getting angry. His name is Todd Kashdan. He is the author of the book The Upside of Your Darkside: Why Being Your Whole Self and Not Just Your Good Self Drives Success and Fulfillment. In the book, him and his co-authors highlight psychological research that shows the benefits of getting depressed, the benefits of getting angry, and the downsides of seeing things with rose colored glasses all the time and being positive and upbeat all the time.

Anyways, a fascinating discussion that dovetails nicely with the series we’ve been doing on depression on the site these past few weeks. A lot of great insights and research that we highlight. We also talk about Teddy Roosevelt. Teddy Roosevelt comes up and Todd calls something that Teddy had the Teddy Effect, and its psychological traits that we often associate with bad guys. Teddy had them in spades but he was able to use those to do a lot of good.

Anyways, fascinating discussion so let’s do this.

Todd Kashdan, welcome to the show.

Todd: Thank you.

Brett: All right, so your book is the Upside of Your Darkside: Why Being Your Whole Self and Not Just Your Good Self Drives Success and Fulfillment. The reason I love this book and it stuck out to me is that it’s a contrarian book. Right now it seems like we’re having this sort of positivity renaissance, or I don’t know. There’s all these books and magazine articles and blog articles about the Happiness Project, or being mindful, being calm. My question is, in sort of this positivity culture we live in, what made you research the downside of happiness and the upside of anger and depression?

Todd: My co-author and I are both researchers in the field of wellbeing. We’ve written books and we’ve conducted the research on the benefits of happiness, positive social interactions for a decade. We’ve read the books you mentioned, and we just thought that particularly it’s an American cultural phenomenon, this obsession with happiness.

What we noticed is it doesn’t resonate with how we interacted with the real world when we went to corporations, with parenting our kids, with dealing with our romantic partners, with friends that are annoying and friends that we love. Those often oscillate between we often dislike and like our friends depending on the day of the week. There are lots of obnoxious annoying people at work, on the road with you on the highway, that you see in stores that are in line with you, they yell at the stewardesses or bartenders that you happen to be a fan of. We realized that these books on positivity, while they’re uplifting and they’re enjoyable and they’re hopeful, they’re not realistic in terms of what we face, in terms of challenges on a daily basis.

We wanted to create a book that wasn’t about that happiness is bad, because nobody should listen to us if we say that. It’s not about that being kind is a bad thing. It’s just that we need to be more agile. There’s a time and place to be friendly and kind, and that should be our default when we first meet a stranger, but this is the show of the art of manliness, where there’s a time and place, after a certain number of attempts to being kind, where you have to switch gears into your psychological tool kit and show some dominance and aggression to get the best possible outcome in a situation. Nobody wants an argument. Nobody wants a fight, but if somebody messes with your romantic partner, if somebody messes with your kids in a very inappropriate way, you’d better have more tools in your tool kit or you’re going to have difficulty getting through life.

Brett: Being nice isn’t going to solve the problem oftentimes.

Todd: It’s a good first start.

Brett: Sure.

Todd: It’s a good first start. We talk about in the book, and a mantra we live by, which is attempt 2 shots at kindness, real wholehearted attempts, and after that, you get to be more flexible in how you respond to somebody. You get to remind them, “Listen. I tried 2 times to be friendly with you. Right now your attitude is absolutely inappropriate. We’ve got some talking to do.” You shift gears.

Brett: Got you. I love that idea of emotional and mental agility. We’ll talk a little bit more about that later on. I know you said you don’t want to emphasize, you were saying that happiness is bad, but you did say that this tendency in our American culture to emphasize happiness and positivity does have some down side.

For example, everyone wants to be happy, right? It’s like in the Declaration of Independence. Our goal as Americans is to pursue happiness. You highlight some research that says that we’re not actually very good at attaining happiness, even though we want it so bad. Why are we so bad at being happy?

Todd: You did a really good job of reading this book. We all want our kids to be happy and we all want to be happy. There’s a sort of paradox here which is when you try to emphasize happiness as the fundamental objective of your life, if I ask you, “Why are you trying to make so much money? Why do you want to enter into a long term relationship with this guy or gal? Why do you want to move to this place?” You’ll probably say happiness. But if your every decision, the determinant is will it make me happier, that’s a very problematic way to live. You will never go to graduate school. You will never work up the effort and the sweat equity in a work place to move up the ladder. You’re not going to get an increase in pay unless by some random way that all of a sudden everybody’s going to get a 3% or 4% bump in salary. You’re not going to have a healthy long term relationship because you need to argue to learn how to argue well. You’re definitely not going to be able to take care of kids because kids can be the ultimate hostage negotiators because they never stop fighting and coming back at you.

You need to deviate from positivity. You need to delay gratification. You’re going to, in a typical day, see people that are more physically attractive than your romantic partner, and more interesting than your friends. You have to sometimes resist these temptations. It’s really what you’re committing to when you’re saying you’re in a monogamous relationship. It’s not that you’re going to not have temptations. Can you resist them? Can you delay gratification? Can you do something that’s hard in the gym for the next 3 months because you want your body to be in a particular place so you can do a triathlon or do a Spartan Race? You don’t enjoy going to the gym at 5:30 in the morning. You do it because you’re on a mission.

This is all deviations from positivity. When we speak about positivity is the be all and end all we miss maturity, wisdom, personal growth, healthy relationships, and most of the things that people want in life.

Brett: Got you. I loved how you talked about the time traveler problem, where we think we know what’s going to make us happy, but then when we get there it doesn’t make us as happy as we think. It’s a problem with goals for me. I’ll set a goal for myself, and I think once I obtain that I’ll be happy. Then when you achieve it, you’re sort of like, “Nah.” What’s going on there? I’m a different person? What’s going on there?

Todd: Yeah. I remember reading about this guy Roberts, I forgot his first name. I think it was—nah, I forgot his first name. Roberts had at some point, was the strongest man in the world. You combine deadlifts, bench press, and squats. He had over 300 pounds. For everyone listening, just put that into your head in terms of his bench press was I think 920 pounds. This guy spent 10 years of his life. He was in the U.K., he was too short to make the national basketball team, and then he was deciding, “What do I want to do? I always wanted to be a professional basketball player.”

He was in the gym working out and someone said, “You know, you have really amazing form. You’re responding very quickly.” He said, “Can I take you under his wing.” He said, “I’ll take you under my wing,” this athletic coach, this strength trainer, he said, “If you can tell me what your goal is.” He said his goal was to be the strongest man in the world. He spent 10 years with that 1 objective. Again, this is not a happy journey. There’s moments of excitement and joy, but as anyone who’s really intensely working on running or strength training or agility training or even just increasing the amount of books they read, there’s a lot of non-joy, but a lot of meaning that comes there.

At the end of 10 years when he broke the record to be the strongest man alive, the next day, he was in a depressive spiral. At that point, what do you do next when you meet that goal? He got himself together in 1 week and said, “You know what? I’m going to teach these skills that I used and that discipline and bring it into the educational system and the workplace.” That’s what he’s been doing. He had to completely turn his life around. For a lot of people, you think of astronauts that have been on the moon, every one of them had a mental breakdown when they came back because what do you do after you’ve actually physically stood on another planet and then all of a sudden you’re taking out the garbage on Tuesdays and Thursdays.

Brett: Yeah, that’s a big letdown for sure. I thought it was interesting too; a lot of the positive psychology research emphasizes all these benefits of being happy, right. Better health, you recognize opportunities more often than maybe people with a depressive outlook on life. You highlight research in the book saying there are some downsides to happiness or positivity. What are some of those downsides that can kind of get in the way of living a meaningful and productive life?

Todd: I really want everyone to kind of think about this. When they’re in a really happy mood. You are much poorer at detecting cheaters. You’re much more susceptible to deception. If you go to Las Ramblas in Barcelona and you’re in an extremely happy mood, and you’re partying and you’re drinking, you don’t notice the tricks of the trade of some of these deceitful characters in the street, where one person distracts you with an attractive guy or woman, and someone else is picking your wallet out of your back pocket while this conversation is happening.

When you have a little bit of anxiety, or a little bit of discomfort, I’m not talking about despair or fear, when you’re a little bit skeptical at the same time enjoying yourself, you have your self-protective self that’s still available there.

We tend to be more self-focused and more selfish when we’re in a happy mood. This has been shown in tons of research studies in Australia. When you’re given an opportunity to split a windfall of money or resources that comes your way with other people, and they can’t see what you’re doing, you’re much more likely to take a bigger piece of the pie for yourself than when you’re in a sad mood or a guilty mood or a little bit of an irritable mood.

You’re less likely to remember details of emotionally provocative situations. Think about being in a fender-bender, think about having a disagreement with someone, with a professor or with your romantic partner about whether you’re holding your share of the chores at home. When you’re in a good mood you’re less likely to remember the details, which makes it problematic because often those conversations don’t go well and the second conversation afterwards, the next day, when you’re making your mea culpas, the more that you remember about the interaction, the more you can build off of it and have a constructive conversation about why you’re not contributing to the chores or why you should be contributing more to the chores and apologizing for not doing so. Hearing their side of the story for doing these things. When you’re in a positive mood you’re more distractible.

Basically, there’s a reason for this, which is when we feel good, we love the status quo, we don’t want to change things. We don’t want to exert ourselves 100% in the gym when we’re in a joyous mood. We don’t want to run interval training where we’re running at full speed for a minute and a half and then slowing down for a minute and a half and then going back to full speed. We want to just go for a jog. We want to just have a nice conversation. We’re not looking to shake the boat. When there’s a little bit of distress and a little bit of skepticism in our system, we’re much more open to listening to other people, thinking, “What can I do to tweak myself, other people and the environment to improve things for myself.”

When you hear this, it’s not that positive moods are better than negative moods. It depends what’s your challenge that you’re facing. If the goal is to live in the moment right now, go for a positive mood. If the goal is to pay attention to explicit details and remember things, being a little bit more downtrodden or anxious is actually better for you.

Brett: Again, it’s going back to that emotional agility.

Todd: Yeah, exactly.

Brett: Here’s another section in your book that really resonated with me, and I think will resonate with Art of Manliness readers and listeners. This idea that the pursuit of comfort and luxury paradoxically could make us more mentally and emotionally miserable. What’s the research on that, saying that comfort can make us miserable, and it can also make our kids miserable?

Todd: The best researchers of parenting, and there’s a term that Katherine Weare came up with which I love, which is called Emotional Safeguarding, which is about parents that just want their kids to be happy. I’m no different. I’ve got 3 daughters and I want my kids to be happy, but there’s a very interesting thing that happens with particularly middle class parents, which is they want their kids to be intellectually challenged in the classroom, they want them taking all the advanced courses. They don’t want them to miss out on anything. They want them to be on the Khan Academy, the website. They want to hire tutors, they want the best teachers that will really push them to the limits, and yet when it comes to their social life or their emotional life, we really try to safeguard them. We plan play dates so they’re with the right people that we’ve already pre-selected in advance, that has a good parent, they’ve got good stock, they’re good kids, they think like our family does, they have the same political orientation, they have the same religious views we do.

It’s a very weird thing. There’s this blind spot where the typical American parent realizes they need to be intellectually challenged in class but socially I want to put all effort … You know when you have your 5 year olds bowling, all of a sudden you have those bumpers that appear so they can’t actually have a … I forgot the term.

Brett: Gutter ball?

Todd: Gutter ball. Yeah, they can’t have a gutter ball. We set up these guard rails so they’ll only socialize with really good kids. Here’s the problem. Once you leave the nest, when you’re 12 years old or 13 years old even, and you start hanging out with kids from other schools, or you start meeting kids at the mall, or wherever kids hang out on the streets, they’re not choosing who they’re hanging out. They’re hanging out with lots of different characters. They need to be able to, how can I read people to know whether I can trust them or mistrust them.

I’ve been thinking about writing a parenting book. The whole premise of it would be this very simple idea, because I’m from New York City, which is if I was to take your kid and drop them off blind-folded in Grand Central Station with 2 dollars, could they make their way back to your house? Would they have in practical intelligence skills the ability to tolerate the stress, the ability to read and understand people? They can leverage that to get their way home. That’s kind of how I train my kids, and that’s kind of how I think about. When we train our kids to be comfortable, they don’t develop the practical intelligence because they don’t have any hoops or challenges that they go through. We did it when we were younger. Our parents did it even more than we did. Our grandparents in the great depression era were amazing at this.

We’re not saying … We obviously all want the creature comforts. I love having a king size bed. I love having a body conforming pillow. I love central air. I’m not saying any of those things are bad. What I’m saying is, if you don’t challenge yourselves regularly you become psychologically weaker.

Brett: Yeah. There was a great quote from King Cyrus, the Persian King, like “Soft lands make soft people,” or something like that. I love that idea of helping your kids develop practical intelligence. It sounds very much, that whole Grand station thing sounds very much like that free range parenting lady.

Todd: Yeah.

Brett: I think she just recently got in trouble, like family services investigated her because people reported that she was abusing her kids, which is weird. The kids are fine.

Todd: Right near me. 30 miles away from my house, because their kids were at a playground, 7 and 9 year olds, by themselves in a playground, and people freaked out and called 911.

Brett: That’s crazy, that’s crazy. Kids are supposed to be on a playground.

Todd: Yes.

Brett: We’ve talked about some of the downsides of happiness. Here’s another thing, and it kind of bugs me a lot. Everyone’s always talking about mindfulness. There’s blogs about mindfulness, there’s books about mindfulness, and don’t get me wrong, I’m a big believer in meditation and mindfulness meditation. Sometimes it’s just sort of irritating when you see it all the time, it’s this sort of end-all, be-all, and once you become mindful then your life will become wonderful. You make the case that there’s actually a benefit to mindlessness. What are some of those benefits?

Todd: This is exactly why … Your disdain is why we called our chapter The Tyranny of Mindfulness. It is tyrannical. My wife’s a yoga instructor, so I’ve been experiencing this for 15 years now. The tyranny of mindfulness in my house.

Let me just give an example of an outfielder on a baseball team. Think about them trying to catch a fly ball. Think about how far they are from the batter’s box, and think of all the variables, if they were to be mindful, to pay attention to, in terms of where do I need to be, how fast do I have to move, I have to pay attention to wind pressure, barometric pressure, the stance of the batter, the speed of the ball, their torque motion, how quickly they turn their hips when they actually hit the ball, the angle that the ball hits the bat, where the sun is. We can’t mindfully attend to all this information.

One of the things that separates human beings from other creatures and other animals, is not that we can become mindful and reach this higher state of consciousness. It’s that so many things that we do amazingly happens at an unconscious gut level. How does an outfielder on a baseball or softball team catch a ball? Extremely simple. 1 simple shortcut, which is, when I run, my eye contact with the ball, the angle, stays the same the entire time that I run. If I keep the angle the same, I will get to that ball. Sometimes I have to run faster, sometimes I have to actually back up for a little bit. We don’t even consciously think about that. That gaze shortcut, gaze to the ball, is all you pay attention to. If you had a baseball player listen to this and pay attention to all those variables to calculate where they should be, they will be completely paralyzed and will never catch a fly ball again. When people choke, I don’t know if you remember Matthew Sasser from the Mets in the late 80’s. Here was a guy hitting a 280, 290 batting average and he couldn’t throw the ball back to the pitcher after a strike or a ball. You’re talking 90 feet. He just developed stage fright. All these psychologists were working with him, which was, “Be mindful about the ball in your hands and what it feels like to be in a crouching stance as a catcher, and standing back up again when you throw the ball, and all that did was screw him up further. Finally, someone trains him, says, “You have to get back into the robotic automatic movements that you’ve been doing since you were 9 years old.” Only by becoming mindless about it was he able to throw the ball back to the pitcher, not by being mindful.

Brett: Didn’t the movie Major League II, they kind of spoofed that? I don’t know if you remember that.

Todd: No, no. I’ll have to see it.

Brett: The catcher, he all of a sudden couldn’t throw the ball back to the pitcher. Instead of throwing it back, he’d run to the pitcher and put it in his glove. The way he overcame it was the coach had him recite, because he read Playboy, and he read the descriptions of the models, what Sheila likes and she’s a Capricorn. He’d just recite that when he’s throwing the ball back to the pitcher. That’s how he got over his choking throwing back to the pitcher. Yeah, you should check that out. It’s hilarious.

Todd: That’s so awesome, because that’s exactly what I’m talking about. By distracting himself, he’s going into … We have 2 modes of thinking. There’s an automatic reflexive mode. If he’s thinking about Playboy centerfolds and all their interests, he’s not thinking about the ball, the sweat that’s dripping down his face, or a stand of 30,000 people. He’s doing it mindlessly, reflexively, automatically.

Mindful is we become very reflective and we become very thoughtful about what we’re doing. You hear people talk all the time about their gut instincts. “I don’t want to sign with this guy,” in terms of buying a house. “I don’t want to buy a car from this guy.” This gut instinct that this guy does not have my best interest at heart. Those gut instincts, underneath them is all of the years you’ve been collecting information about people. Millions of years of evolution have developed such that we have these quick signals of whether to trust someone or mistrust someone. We get the chills sometimes when we’re with somebody in the elevator, or we have the goosebumps when we’re walking next to somebody. We look and realize there’s some sort of chemistry there, there’s some pheromone that’s happening between the 2 of us. I’m not saying always believe your gut instincts, but what I would say is what we’re doing now is we’re discounting that your gut instincts is really your intelligence on speed, and that we should first pay attention to that before we think about, “I want to try and be mindful every moment of our lives.”

Brett: Got you. I thought it was interesting you talked about how Presidents doodle. Most of the Presidents doodle during meetings. That it’s sort of a mindless activity that actually helped them pay attention more.

Todd: There’s a big thing that we know about creativity, and almost every business organization gets this wrong. What normally happens is, you grab 15 people, you bring them into the large, oval table, and you have this brainstorming session. Extemporaneously, you’re sharing all these ideas together. That’s actually not how creativity works effectively.

People need to hear what the problem is, give them a couple of constraints about what they can or can’t do based on whoever the consumer is, whoever’s pulling the purse strings. We need to have 2 pages. It has to have a story. We’re looking for 20 to 35 year old women who will stay at home, that’s our target audience. With those constraints, have them think about some ideas, but give them time to do something totally distracting that has nothing to do with the project. Whether it’s going for a bike ride, going for a nap, going in the shower, having sex, whatever it is. Then come back to it and when you’re in the incubation period of doing something else, your brain is actively mixing ideas together. It’s like a smoothy. It’s blending ideas that are no longer being edited by you. That’s part of the magical process of creativity, that incubation period of doing something else other than the activity you’re trying to be creative in.

Brett: Got you. I think you’ve touched on it a little bit in your discussions of the downsides of positivity, happiness. Explicitly, what are some of the upsides of depression? Right now we’re doing a series about depression on our site, I feel like in America particularly, because we have this emphasis on happiness, that if you’re sad or you’re feeling down you’re broken. You need to get that fixed. You highlight research that there’s actually some possible benefits to being in a low mood for a period of time.

Todd: No question. One is, it’s very difficult because the appropriate norms for men of expressing sadness, the stigma is massive. You’re weak, you’re broken. Exactly how you described it. It’s particularly hard for men to acknowledge that sadness has a benefit. I’m going to separate … Depression has its own term, which is really a psychological problem. We’re really talking about sadness. It’s the feeling of being sad. You’re just kind of downcast.

There is no quicker way to solicit help and cooperation and support from other people than having a sad facial expression. We often don’t know what it feels like and whether we actually look sad to other people. If you look in the mirror you can do this. Method actors do this, like De Niro, all the time. We often don’t know. People say, “Oh, you look kind of sad today.” The typical male response, including myself over my entire lifetime, is “No, I’m fine,” and you try and snap yourself out of it. Why did someone ask you, “It looks like you’re a little bit sad today?” They’re right now in that moment, they saw that expression, and they want to do something for you.

What I would say is, your body, that emotion is not something to get rid of. That’s an emotion. We have to allow ourselves to recognize that part of being really psychologically strong, mentally strong, is allowing ourselves to be vulnerable. We can’t do everything ourselves. The reason that baseball teams and basketball teams and football teams are great metaphors is because you’re leveraging the strengths of a number of different people together. That’s the only way that these teams make it through the rankings and end up in whatever the final championship game for them to be in. Not because of just Kobe Bryant. It’s because of the supporting cast that does all these small little details that work with him. One person can’t get the game.

It goes like that with everything in life. In parenting, if you’re unwilling to accept support because you’re not feeling yourself, you’re a little bit out of your body for some reason, you’re going to yell more at your kids, you’re going to be less patient, you’re going to be less compassionate, you’re not going to have as much fun with them. These will lead to the memories of what childhood was like. A lot of us, we had tough dads. You go back a generation, they weren’t soft with us. We have these ideas that part of being a man is never showing that you’re fearful, never showing that you’re sad, and never showing that you feel guilty. That’s a problematic idea because we can’t live up to that because all these emotions have a use.

Guilt is this really beautiful emotion. It feels sad, but it’s a reminder that I need to … It’s a motivator. It’s telling us we should do something else, something to repair our relationship because we did something that pissed somebody off or upset somebody. That’s a good emotion. Prisoners that feel guilty when they’re in prison are less likely to go through the revolving door and engage in another crime and end up back in the system again.

Brett: What about anger? That’s something else that’s often directed toward men. You’ve got to get control of your anger. You can’t be angry, but there are some benefits to anger. What are those?

Todd: It’s been 2 years of interviewing people for this book and writing this book and now I’ve been running around talking about it. No emotion do people have more problems with than anger. This has been a real big surprise to me. I thought it was going to be sadness or fear. Part of them, for anger, is what you just described, that we have to keep these Neanderthal attitudes, these frat-like 20-something angering impulses to ourselves. We’re not allowed to be angry now that we’re adults. We’re supposed to be mature enough that we can handle all difficult situations.

Anger is the emotion that appears when we feel as if the goals that we care about are being obstructed by somebody else or something else. Our moral code has been demolished by somebody, so we feel angry. It ends up being, if you’re with your family and you’re having dinner at a restaurant and someone smokes a cigarette and blows it right over your table, you experience anger. If you’re waiting patiently in a parking lot for a parking spot and someone grabs it right before you, even though you’ve been sitting there for 2 minutes, you get angry. This is not an emotion to hide. It’s telling you something important. The question you ask, if it’s so important, is how do you effectively display this in a healthy way to get the best possible outcome?

A couple things. One is, and we talk about this in the book, which is the idea of having a caveat before you express your anger. Think about it at work. Think about if your boss pissed you off. There’s a power imbalance. What a lot of people say is, “It’s easy for you to say anger is good because you have tenure and you can’t get fired from a university unless you have sex with 17 students.”

In any workplace, if you feel that your boss is being disrespectful to you, if you feel as if someone’s harassing you, there’s a way to communicate this. When you schedule an appointment to meet with your boss, you don’t start off by right away screaming and saying that you feel disrespected and particularly because they did it in front of other people. You tell them, “Listen, I’m really uncomfortable about something I want to tell you. It’s important to me because I can’t give you the best possible work I can unless we have this conversation.” What that does is, when it’s said softly, is it brings his or her defenses down a little bit so he or she is ready to listen to you. It’s probably true. You’re probably going to be uncomfortable having the conversation so why not just admit it.

Once you have that caveat out of the way, there’s a couple things. One is your anger, your expression has to be proportional to the problem that you’re dealing with. If your boss was just trying to be funny, and ended up talking some smack about you in front of a bunch of people, you can’t grab a lead pipe and smash everything off of his table. That’s not proportional to the problem. You can raise your voice, but for firing you probably is too extreme for that situation. They will see it in your face. By you sitting up in your chair and looking them right in the eye and saying that, “Listen, the way that you spoke about me in front of that room full of people was completely disrespectful to me and I saw you laughing, which made me even more upset. What made me particularly perturbed about this which is why I felt so compelled to talk to you, is you didn’t do it 1 on 1 with me, you expressed some of the problems you had in front of a room full of people.”

What you’re inducing, you’re being very clear. The anger is about what they did not who they are. That’s really important for expressing anger effectively. I’m not going to say, “Listen. You’re an ass hole. You’re a bad manager. You are a hypocrite with the values you say that you have.” Anything in that nature, everything that you say is not going to be heard. But when I talk about the exact behavior and the specifics of you chose to say that in front of a room full of people, they can listen to that and that’s something they can actually acknowledge and apologize.

The other part of anger for making it effective is you need to be clear and be able to look at somebody and stand your ground throughout the expression of what was bothering you. A lot of people express their anger, what bothered them, in the beginning. Then they kind of shy of and let their voice get’s a little bit softer in pitch and a little bit more quiet and timid. It’s as if you’re not really fully standing up for yourself.

The final piece of expressing anger effectively is you have to allow the person to have an out, which is, “I don’t expect you to respond right now to what I just told you, but when you’re ready, if it’s a day from now, 2 days from now, you can come back to me. I had to tell you how I’m feeling.” They might be defensive, and they might not give the response you want. I know for me, I’ve got 40 people who work for me. A lot of times people tell me that they’re pissed off about something I’ve done. Immediately I respond in kind of a witty way, which is saying, somehow downplaying what they’re saying, and then 24 hours later I end up apologizing to them, saying they were absolutely right. I thought about it overnight and I couldn’t sleep as well as I wanted to. I’m glad you were assertive, I’m glad we have a good enough relationship where you can speak your mind. I want to get the best from you, I want you to feel good working here, so we need to have these conversations. It won’t always go that way, but it’s important to develop a pattern of standing up for yourself.

Brett: That’s some great advice there. At The Art of Manliness we’re big fans of Teddy Roosevelt. He’s like the patron saint of The Art of Manliness. I was really tickled that you had a whole chapter called the Teddy Effect, dedicated about Teddy Roosevelt and his sort of the dark side of his personality that made him successful. Can you talk about what the Teddy Effect is?

Todd: First of all, this is why I’m here. Anyone that has Teddy Roosevelt … I’ve got a bobble head of Teddy Roosevelt that’s on both of my desks, at home and at work.

Brett: That’s awesome.

Todd: He is my man, so I’m with you guys. I’m going to be a huge fan of your show now. Teddy Roosevelt is what every President should be and should aspire to become. Unfortunately, in today’s world, there’s no way you can have another Teddy Roosevelt, with the blogosphere, people having smart phones everywhere. Here’s a guy who would swim naked in the Potomac River right behind the White House in the middle of the night. Here’s a guy that would leave in the middle of, while the Senate was in session, and just go hunting for bears in North Dakota, because he didn’t want to listen to what they had to say, until they actually could resolve something on their own. Here’s a guy who in the middle of giving a speech, he had notes in his pocket and was shot and the bullet did not pass through the notes in his pocket. He took the notes out, looked at the bullet, put it down, and kept on giving his speech.

Teddy Roosevelt had a lot of the characteristics, similar to what we would call psychopaths, which is, Dexter, that HBO show, is a great example of a psychopath. If he was in, fell into the wrong peer group, this was a guy who would have been an amazing serial killer, the leader of a gang in inner city Chicago, and an amazing drug dealer. He happened to just have these leadership skills, he found a place in politics. Before he was in government he was actually with the police in New York City. This is a guy who, he’s a selfish guy. He recognized that he wanted his legacy to be amazing. He was willing to put himself ahead of a lot of people over the course of his career. He had a strong inner circle all the time that was considered part of him. He protected them just as much as he did. His loyalty was huge. This is a guy that was narcissistic. When we talk about narcissism, most people don’t realize that there’s a healthy side of narcissism and an unhealthy side. Teddy had a real good batch of the healthy side of narcissism. If you don’t mind, I’ll explain these 2 sides to your viewers.

Brett: Sure, that’d be great.

Todd: An example of the unhealthy side would be Metta World Peace for the Lakers. It’s you can call it narcissistic rivalry. Narcissistic rivalry is when, it’s almost as if you’re holding a sign that says “I will never let any of my rivals get what they deserve. I want everything to come to me.” Your focus, your obsession is I have these amazing strengths. I am an amazing person, and I’m going to make sure that nobody holds me down. You’re obsessed about where your rivals are, where your ranking is. All of your time and effort is not focused on achievement, it’s not focused on doing great things, it’s focused on being better than the other people that you’re competing with. Taken to the extreme, a sense of entitlement, a feeling that you’re better than everybody else. Focusing on passively aggressively blocking your rivals from getting the ball, preventing your colleagues from being acknowledged that they were part of the reason that this transaction was successful. It’s just a bad thing for organizations, it’s a bad thing for athletic teams, it’s a bad thing to find in a relationship.

Metta World Peace is a really good example of this. The guy had 100 domestic abuse problems, didn’t get along with the other L.A. Lakers on his basketball team, changed his name because he wanted the spotlight on him. He would not pass the ball to certain people on the team if they spoke badly about him in the media. You’ve just got to, you just don’t do as a colleague. You can dislike someone, but when it comes to tournament time, or game time, you’ve got to put that aside.

On the flip side, the healthy side of narcissism, we can call it narcissistic admiration, Kobe Bryant is the perfect example of this. It’s as if you’re holding a sign that says, “I have amazing strength that people still don’t appreciate.” Kobe Bryant, if you talk to any player in the NBA, they will say he’s the most, one of the most annoying people in the league, and yet he’s incredible, so he deserves it. Yes, he’s narcissistic. Yes he thinks he’s amazing. Yes. Before games actually start with the L.A. Lakers, same team as Metta World Peace, all the players practice on one side of the court, when they’re just shooting around, and Kobe feels he needs to be by himself to get in his Zen zone, and he’s on the other side shooting by himself. The team understands this, they’ve accepted this. There’s a sense of entitlement there. There’s narcissism there. They guy speaks 5 languages. The guy’s one of the best players in the NBA in terms of his ball handling skills. He screens other players but he does it because he believes he’s capable of doing amazing things, and he’s pushing everyone, including himself, to be the best possible person.

Michael Jordan was the same way. He’s famous for punching Steve Kerr in the face during practice because his dribbling was not up to par in practice. No cameras, nobody was there. He punched Steve Kerr right in the face. In that moment, he gained the most respect for Michael Jordan, and they became best friends on their team. Even him and Scottie Pippen. Steve Kerr and Michael Jordan were closer than him and Pippen, because he recognized that this guy wanted to be the best possible and a punch was not about to injure that relationship and that punch was not going to interfere with him wanting to be the best. It was the recognition: I’m amazing, I have gifts. They tend to be charismatic. They tend to attract other people. People want to emulate them. They love this and it just makes them work harder.

Teddy Roosevelt emulated narcissistic admiration. This was a guy who thought he was the best President they ever put into power. He did it, he felt that way, but because of that, he felt the necessity to live up to that expectation, that he had for himself and for his legacy. He worked hard, as hard or harder than any other president that got there.

Brett: Yeah, he’s the only person who … He petitioned for the Medal of Honor. He thought he deserved the Medal of Honor, after the charge with the Rough Riders, right?

Todd: Yes. The Spanish American War.

Brett: He got back and he was hoping for a Medal of Honor nomination and no one got it and he actually petitioned for it, which is sort of like a faux pas. You’re not supposed to ask for the Medal of Honor.

Todd: Absolutely.

Brett: I guess that’s an example of his narcissism. He finally got it, but it was like after he was dead. I guess that’s another example of his narcissism.

Todd: And to keep with that in terms of medals, this is the only guy ever who had the Medal of Honor and the Nobel Peace Prize. One medal is for war, and one medal is for diplomatic negotiations. You talk about social agility. You want to fight and you want to go to war, boom. Teddy Roosevelt. I’m your guy. It ends up being that we need to figure out how to figure out our differences and come to tolerate each other? Boom. You want peace? Teddy Roosevelt’s your guy. In fact, as opposed to, you look at how people are spoken about now in politics: you’re either a hawk or you’re not. Really what you want is agility. I think that’s what all of us want. I know that I want that for my friendships, I want that for my colleagues. That also entails that they’re going to piss me off sometimes. I want the best of the best and the best people who bring every dimension of their personality to the plate when it’s beneficial and necessary, and not prematurely discard it because it’s not appropriate to be narcissistic, it’s not appropriate to be Machiavellian and selfish. The best people appreciate every single side of their personality and bring it to bear.

Brett: Do you have any advice for folks who maybe aren’t naturally Machiavellian or narcissistic or psychopathic? Yeah, research shows that these types of people with this sort of dark triad often do well in leadership positions, they often advance faster. What do you tell for the guy whose temperament is just to be sort of humble and not rock the boat? What can they do to embrace the Teddy Effect?

Todd: It’s a great question. Actually, as a mentor, working in a university, I give this kind of feedback all the time. For people that are kind, this is your virtue. You’re kind, you’re generous, you’re compassionate, but there’s a tipping point where it can actually interfere with everything that we do in our work. A perfect example of this is, if you’re in my group to work on a project, I need you to disagree with me sometimes. I need you to take the devil’s advocate position, even if you don’t believe it. We need to think of what regulations, what are our competitors doing, what about the market have we not thought about as we get super excited about this product that we’re interested in, or this project that we’re interested in. I train people in our culture, that I seek dissidence. When you disagree with me you’ll gain more equity in my mind than if you agree with me. I’m not looking for people to agree with me.

The advice that I give to people is essentially, the goal is not to be a narcissist. The goal is not to be a psychopath. The goal is to think about we can learn from these people like Teddy Roosevelt and Kobe Bryant and Michael Jordan who have these qualities, and say, “There are behaviors that they engage in that we just want to add every once in a while.”

If you’re in a group setting and everybody’s agreeing about an issue, you can actually gain a great amount of leverage, like trying to really intentionally, what are people not thinking about, or even raising the question of, “I realize that everybody’s excited, and I don’t want to be a buzz kill, but I’m wondering if we should … I think we need to have the conversation about what have we not considered because we’re falling in love with our ideas too much.” If that kind of statement gets static or a negative response, that’s even a greater kind of smoke alarm alert that there’s a problem with the group. That’s what happened with the Cuban Missile Crisis which is that nobody would disagree with JFK. Everybody was so in love with him and so in love with the idea that nobody said, “Listen, let’s take 15 minutes and talk about what are we getting wrong.” There’s always something you’re not considering there. That’s one thing. The group setting, that’s something that I suggest.

The other one, I strongly suggest this for the dads, moms parents, who are listening, is you need to start being selfish. If you worry about whether or not you’re parenting your kids right, your kids are going to be fine. You’re thinking about it, you reflect on this, you’re good to go. What I suggest is, if you don’t recharge your own batteries, if you don’t spend time with your friends, if you don’t work on your body, if you don’t spend time reading books that you like to read, and take some time away from parenting, you’re going to be a worse parent. You’re going to be more impatient, you’re going to be resentful, you’re going to get upset at them more easily, you’re going to be actually less engaged and checking your smart phone more often. Take time, build in time for yourself and be selfish. It’s the diametrical opposite of what people speak of. It doesn’t mean that you’re a bad parent, it means you’re going to be a better parent. The parent that doesn’t take care of themselves is, by definition, an inferior parent because you’re a bad role model for your kids of how they should live their lives when they’re no longer under your wing. That’s the parenting piece of it.

The relationship part of it is, you need to know what your values are. You should, if you don’t know the answer to what are the values that you’re not going to move on, that are fundamental to your decisions, you need to spend some time and reflect on this. I know for myself, the idea of putting my own personal signature on my work, and not being replicating what other people do, is a fundamental value that I have. One of my fundamental values is making sure that I have an ancient Greek style taking care of mind and body and that’s the way I’m going to live every single day of my life. I’m going to spend at least 1 hour on my mind by reading books that aren’t related to my career, and 1 hour on my body. I make that almost like a monk in a Tibetan monastery. The day is not finished until I’ve spent time … It’s a value system that I abide by. You need to know what you value or else you’re running around aimlessly.

The reason you need to know this is because when your values are compromised, that’s when it’s time to deviate from kindness. It’s time to be willing to be angry. Be willing to disagree with people. Part of it, I suggest people clarify their values and be willing to step into a discomfort zone when someone does something that goes against what you value.

Brett: This has been a fascinating conversation. Before we end it, where can people find out more about your work?

Todd: I have a weird last name, so if you just put Todd Kashdan in Google, K-a-s-h-d-a-n, you’ll find my website and I give away … A ton of articles are available for free on my website at

Brett: Fantastic. Well this has been a fascinating conversation. Thanks so much for your time. It’s been a pleasure.

Todd: It’s been great being here. Anyone that loves Teddy is automatically a friend of mine.

Brett: Awesome. Our guest today was Todd Kashdan. He’s one of the co-writers and authors on the book The Upside of Your Dark Side. You can find it on Go out and get it. A really interesting read. You’ll also find out more information about his work at That’s

Well that wraps up another edition of The Art of Manliness podcast. For more manly tips and advice, make sure to check out The Art of Manliness website at If you enjoyed this podcast, I’d really appreciate it you’d give us a review on Stitcher or iTunes, whatever it is you use to listen. I don’t care what it is, just provide some feedback. I’d really appreciate it, and tell your friends about it. That’d be the best compliment you can give me is recommending the podcast to a friend.

Until next time, this is Brett McKay telling you to stay manly.

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