The Four Levels Of Thinking And How They Shape Your Life
May 13, 2025
Hosted By
Do you ever notice how some people obsess over things, gossip about others, or recycle old ideas? Why is it that true innovators think differently? Dan Sullivan and Jeffrey Madoff break down the four levels of thinking and explain why thinking about your thinking fuels creativity, collaboration, and breakthroughs.
Show Notes:
Most people spend their lives fixated on things, people, or others’ ideas, but true innovators think about how they think.
People who think about their thinking are looking for other people who are doing the same thing.
The highest level of thinking isn’t competitive—it’s collaborative. Two original minds create a third idea neither could alone.
Nearly every meaningful innovation stems from that fourth level of thinking, where you examine how and why you think the way you do.
Some of the most creative people don’t even realize how they think—they just do.
The moment you care more about stuff than ideas, you’ve lost the game.
Like casting a play, the best teams are built when you assign people roles based on their unique strengths, not rigid job descriptions.
If your team fears being wrong, they’ll never risk being right. Defensiveness is the enemy of breakthroughs.
Corporations reward conformity, but entrepreneurs win by asking, "What if we did the opposite?
Resources:
Casting Not Hiring by Dan Sullivan and Jeffrey Madoff
Thinking About Your Thinking by Dan Sullivan
Learn more about Jeffrey Madoff
Dan Sullivan and Strategic Coach®
Episode Transcript
Jeffrey Madoff: This is Jeffrey Madoff, and welcome to our podcast called Anything and Everything with my partner, Dan Sullivan. Today, we're going to talk about language, meaning, criticism, and thinking. And Dan and I were talking before we started recording here about what Dan calls the four levels of thinking, which I think is a great way to start, because we're going to go to at least four levels of thinking during our conversation for the next hour. What are the four levels of thinking, Dan?
Dan Sullivan: Yeah, this is from our coaching entrepreneurs. What I notice is that there's a particular type of entrepreneur that I enjoy coaching in Strategic Coach. And I'll tell you the three that I don't really like having as clients. People who constantly talk about things, and things means, you know, their belongings, their material, how much they have, you know, houses, cars. A lot of it's about technology. They have this thing with technology, and I find it really boring. And number two is people who talk about other people, and they're big social media fans, and they're always talking about people. And the worst ones are the ones who talk about other people's things.
So there's a compounding effect coming from the bottom here, okay? But, you know, they will know and interact with hundreds of people in a week. You know, it's more than I've met in my lifetime. And then the third level is really interesting because we mistake that these are really, really smart people and they think about thoughts, but they're the thoughts of other people that they're the experts of, and you see a lot of this in universities and colleges, they can have very, very astute thoughts, but their thinking is really about other people's thoughts. So they're not original thinkers, but they can comment on things, and there are people who have spent their entire academic career mastering other people's thoughts, and I don't find those very interesting.
The ones I find interesting, and you see a lot of it in entrepreneurism, but you would see it in any creative field, are people who have the ability to step back and actually observe how they're thinking about things, and they're looking for other people who also think about their thinking. This is how I'm thinking about this, and it's really interesting what I notice about my thinking. It's almost like they're watching a movie, you know, it's sort of like an animated movie where they're thinking, you know, is in scenes or it's there's actually a dramatic fashion to it.
And I find it fascinating that I acquired this pretty early in life and that I've been really lucky over my lifetime to really constantly come across people who have this other ability and some of them are really conscious of it and some of them aren't really conscious of it. It's just the way that their brain works. In my sense, everything new that gets created in the world really comes mostly from this fourth level of thinking. And you try to expand the numbers of other people that you have around you who also have this ability because together you can create really neat stuff. I think you have this ability.
Jeffrey Madoff: The ability to think about not things.
Dan Sullivan: No, just how you're thinking about things. And I know you took philosophy and psychology in university, but I don't think that's where it started. You took those subjects because they allowed you to think about your thinking.
Jeffrey Madoff: Well, that's right. That's right. I remember when I went to college, the way that I would choose classes after the very first semester, I would go to the university bookstore, I went to University of Wisconsin in Madison, and I would look at the books that were the reading for the courses. And if I found the books interesting, that were dealing with questions that I thought were interesting, couple that with having some good professors, that thinking about thinking was really fascinating because that helped me define who I was. How did I think about these things? Why did I think about these things? Why was this important to me?
And like you, people who just talked about things tried to look at life as a competition where I've got more stuff than you've got. I had an early roommate in college who was from a, I guess, a wealthy family. I had a nice record collection because I've been into music for so many years. And he came into my room at one point and said, you know, when I came to school, I thought, wow, you've got a bigger record collection than anybody I've seen. Well, I've got more than you do now. Good. That was my response. Good, good. Get out. Well, that hopefully is our last conversation.
Dan Sullivan: Well, I think the first three are competitive. I think the fourth one is collaborative. I think the fourth level of thinking because you know that what you're doing is original and you can spot what the other person is doing original and there's a real opportunity to put two original thoughts together to create a third. I think that's what we're doing, writing the book that we're writing, Casting Not Hiring. I've developed a lot of thinking about you know, that it's better that the people who work in your organization have roles rather than jobs. You've been in theater all your life. And we got talking about it, and it was basically just a conversation we were having about good hiring and bad hiring in the business world. And you said, you know, it shouldn't be hiring, it should be casting, casting roles. I thought, there's a book, and here we are, you know, with a deadline approaching.
Jeffrey Madoff: Thanks for that reminder.
Dan Sullivan: Actually, I think we're ahead of the game myself.
Jeffrey Madoff: And I think there's reasons we're ahead of the game in the sense that we're sharing the same goal. And that goal is not, this is my belief, this is your belief, but rather we're speaking from our experience about how we think about what we're doing and kind of growing the idea mutually. To me is what makes things exciting and fun.
Dan Sullivan: Yeah, and the other thing is I wouldn't have written this book on my own and you wouldn't have written this book on your own.
Jeffrey Madoff: That's right.
Dan Sullivan: I mean, it was an interesting thought, but it wasn't anything that triggered my forward schedule of things that I was going to be involved in. I do a lot of writing, and you probably wouldn't either, but there's the fact that we both got a real energetic thought about that, and we talked about it in the podcast, and I created a little form that says, you know, if we did this as a book, this is what it would look like, and here we are.
Jeffrey Madoff: Yeah, I think it's like a piece of stone hitting a flint and you get a spark. And that spark is exciting, especially when the originators of that spark, in this case, you and me, are sharing in that idea of creating a fire and warming ourselves with those ideas and wanting to communicate those ideas. And I think that's really exciting to do. Makes me think of many phrases drive me crazy. And one of them that drives me crazy is when somebody says you have to be intentional.
Dan Sullivan: Or authentic.
Jeffrey Madoff: Or intentionally authentic or authentically intentionally intentional.
Dan Sullivan: You know?
Jeffrey Madoff: So why does that bother you? I'll tell you then why it bothers me.
Dan Sullivan: Well, first of all, I think it's very, very difficult to know what the other person has in their mind. You know, and I'll tell you another one. You share a story about your life. So I'm not forgetting authentic and intentional, but I want to add this one to it because one of the stories I talk about is overcoming a real setback one day in 1978 where I was bankrupt in the morning and divorced in the afternoon. Two really bad report cards in one day. So I'll say it, and people say, thank you for being vulnerable. I said, what do you mean by vulnerable? And they said, well, just sharing that type of experience. I said, oh, is vulnerable sort of like telling the truth? I mean, is that what you're talking about? So what about a person, Jeff, who is authentically, intentionally vulnerable? You could write books of philosophy and psychology on that theme.
Jeffrey Madoff: Yeah, but what is it?
Dan Sullivan: It's like, I think it has to do that they're not actually having a connection with their own creativity and they don't actually have good connections with other people. So they've got, I'm being authentic, you know, I'm being intentional, you know, it's like an act or something.
Jeffrey Madoff: Well, there are people that I think are intentionally and authentically fake.
Dan Sullivan: Yeah.
Jeffrey Madoff: And I think that, you know, when somebody says be intentional, I don't know how else to be because I mean what I say. So if my intention is to communicate with you, and if I'm telling you a joke, my intention is to make you laugh. Sometimes that works, sometimes it doesn't. But everything I do has got a certain intention. I don't just blabber to hear myself blabber and fill the airspace.
Dan Sullivan: Yeah, it's like one of the founders of MGM, great movie company, Sam Goldwyn, he said, you know, the most important skill in Hollywood is sincerity. Once you can fake that, you can really go a long way. And I think it's the same thing with once you can fake intentionality, you're making real progress. Once you can fake authentic, then you're really there. It's like there's a faking way to approach life. Well, true. And I've seen it.
Jeffrey Madoff: So how do you recognize it?
Dan Sullivan: How do I know when someone's being authentic? One is that they don't use the word authentic. And the same thing would go for intentional and vulnerable. They're just communicating. And usually it has an idea attached to it. One of the things I've been thinking about is how the experience of writing this book together is so different from a previous experience I've had. And it took me a while, you know, it took me a month or two to kind of adjust that you do your best writing at night and I do my best writing in the morning. But we have a different approach to it.
But you really go for a deep foundation. And I just sort of sketch out blueprints. I sort of sketch out blueprints, like putting together the structure. I just want to see what the blueprint looks like. But you're really putting in the foundations of what's going to support everything else. And it took me a couple of months to actually, you know, kind of adjust to that, how you were doing it. I feel, you know, over the last month or so, especially when copies started getting developed, that we're both pursuing the same final design of what the book looks like. So, there's just an example of me thinking about my thinking.
Jeffrey Madoff: Well, and it's acknowledging that we have the same goal and then working towards that goal. And that what we're both doing is all of it's based in thinking about how you think about something. It makes me think of a situation that I had with a client and I was working with the head of a division of that company and very smart woman who worked for one of the networks before that. And I liked her a lot. But as time went on, her own opinion was, I was watching it evaporate. And she would precede everything by, well, I don't know that so-and-so is going to understand this. And I said, okay, well, all I'm interested in right now is your opinion. Well, I don't know if so-and-so is a level two thinker. And I said, I heard you say that, but I'm asking you, what is your opinion of it? She goes, you know, well, I know he doesn't like fast editing. I'm not sure that that's going to work for him. I said, but that's not what I'm asking you.
Dan Sullivan: She's a total level two thinker.
Jeffrey Madoff: What is a level two thinker? Define that for me.
Dan Sullivan: Thinks about other people.
Jeffrey Madoff: And what their reaction is going to be.
Dan Sullivan: Yeah, yeah. She's way, way far away from what the idea is that you're discussing. She can't think about the thinking that went into it. She immediately is saying, you know, is this politically possible? Well, thinking about other people is political.
Jeffrey Madoff: Yeah, and so I finally said to her at one point, I've asked you
Dan Sullivan: Well, the other thing you would have, today's things, you're using words and you're doing an image that is not ideologically correct. And that's someone who thinks about thoughts, you know, that their gradient is basically, is that a good thought or a bad thought? But not what the actual thinking is. They're not actually, that's really interesting. How are you seeing this, Jeff? Can you tell me how you're seeing this, you know? that would be really attractive to the idea. Can you explain a little bit more what you're seeing about the idea? It's not political and it's not ideological, it's just the thinking. What's the thinking going in?
Jeffrey Madoff: Well, exactly, because that's how you can then understand what they're talking about. And it got to a point where I said, you know, I've asked you now four times what is your opinion, and you haven't been able to answer me. And when you first came to work here, you were able to voice your opinion. I don't know whether it's the corporate structure that just shut you down and now you're just concerned about what everybody else thinks before you even have your own opinion, like a great Preston Sturges, what was it called? Something about Fourth of July.
And it was set in the advertising world. And the head of the advertising agency says to the character, when I want your opinion, I'll tell it to you. And it's that kind of thing, that your own thought process has become so paralyzed because you're always thinking about the consequences of doing something wrong.
Dan Sullivan: Or new.
Jeffrey Madoff: Or new, right. Well, and oftentimes new and wrong are the same thing to people, you know. And the answer that I hate hearing the most is, well, why are we doing it that way? And it's, well, that's the way it's always been done. Well, that's interesting. And so it was fascinating.
Dan Sullivan: I think the big thing is that your comment to her is really being in the corporation wore her down. And that's very true. And I would say that people who think about their thinking and develop a real skill around thinking about their thinking, for the most part, don't work in corporations. Well, they don't work in any pyramidical structure where getting to the top is agreeing with other people's opinions. Okay. And the other thing is that my observation is nobody ever floated to the top of an organization by saying yes. They get there by saying, no, you know, no, it doesn't cost you anything. Yes. It's a risk because yes, would be something new. No would be let's not do anything different.
Jeffrey Madoff: Well, the phrase that came about in the seventies was you won't get fired for buying an IBM. And it's because it was accepted, an accepted norm, if you were getting a computer, you got an IBM. Not that you were buying the best, not that you were doing anything new, it's that you were playing something safe. And that safety, I mean, there's a place for that in business, but for me, for you, it's not a very interesting place because the exploration, the discovery, the surprise, the innovation, the creativity is missing. And so that's when you become present in a kind of hall of mirrors because you can't even find your real reflection anymore because it's distorted through the perceptions of everybody else around you.
Dan Sullivan: Yeah, and we have evidence of drug addiction, mental illness today, that a lot of people are caught in this thing where they really don't know who they are. They've been told they're this, or they should be this, or if you're going to be accepted, you have to do this and everything else. But they don't actually have an independent point of view about whether they like that or not.
Jeffrey Madoff: Well, and the evidence for that, I agree with you, and the evidence for that, which is another phrase I can't stand, is be the best version of yourself.
Dan Sullivan: Mm-hmm. Mm-hmm. Or live up to your potential.
Jeffrey Madoff: Yeah. Yeah. Or you know what that is, and you know that I'm not doing it. But that best version of yourself, I'm not aware that I have any other versions going on. This is kind of it, you know, with the inherent limits of what I may have. This is the version. There's not a best version. Some things go better than other things, but that doesn't mean it's the best version. It just means that I'll try a bunch of things and they don't all work.
Dan Sullivan: Yeah. Jeff, we were both born in the 1940s, and I grew up in a radio world. I didn't grow up in a television world. I was nine years old before my family had its first television. And you're a little bit younger. And I used to listen to radio at night. You know, my mother would have some of the Gabriel Heatter that was a you know, he was a commentator on one of the big networks, you know. And, you know, the various radio stations, depending on what you were listening to, they had commentators. Fulton Lewis Jr. was one, Gabriel Heatter was another one. And, you know, they were very confident spokespeople for a particular point of view.
But the other thing is I had a lot of time by myself, and I made up games for myself. I would be various characters from the fictional world, like Robin Hood and everything like that. Farmland, I grew up on a farm and we had woods and everything else, I did that. And I got really used to being able to entertain myself and educate myself, you know, learn things and set goals and that. And I'm wondering if really early in life, you're in a social network and you're adjusting constantly to, and you miss the junction where you could have your own opinions regardless of whether other people agreed with you or not. People not agreeing with you is either the worst thing in the world or it's an interesting thing that allows you to develop your new ideas that somebody thinks differently than you. And then you think about how do I think and why do I think about that? But I'm just wondering if it's a social thing where they get socialized very early to be a kind of person that's acceptable to the group that they're in.
Jeffrey Madoff: Well, I think it's also a big part certainly in my case, a big part of. The parents.
Dan Sullivan: Oh, yeah. Them.
Jeffrey Madoff: That's right.
Dan Sullivan: Right. You know, my first thing I knew about my parents is that they weren't my friends. They were parents. There was God and your parents were halfway to God.
Jeffrey Madoff: You know, because my parents encouraged me to do things. You know, if I was writing stories, they'd read them if I wanted them to. You know, when I was doing drawings, they had retail stores and they would bring home big pieces of craft paper so that I could draw on a bigger scale and do that. And so from the very early years, whatever my talents might have been and whatever explorations I was in, my parents were always, they never said, don't do that. They never said that's a waste of time. They never said anything like that. And as a result, whether it was writing stories, which I started doing very young, drawing, which I did when I was very young, putting on shows, which I did when I was very young, as we've talked about in previous podcasts, having a movie theater in my basement and editing together soundtracks and all of that and creating the posters, all that stuff.
And I think a lot of ideas and creativity get squashed really early in life. And then there are those that their expression is a kind of rebellion against that. And so I think that creativity, creativity can come from a dark place or it can come from a positive place. The output of both can be fascinating and great. But I think in my case, I was fortunate that I was never discouraged and often encouraged to do things.
Dan Sullivan: Yeah, I think one of the things is your parents aren't living their lives through you.
Jeffrey Madoff: That's right.
Dan Sullivan: And I see a lot of that today, that somehow the child actually has control over their parents, because if the child doesn't do what the parents think is the right thing to do, it reflects on them. And, you know, they have their own social networks where they do that. I think the other thing, I mean, just reflecting on it, is it wasn't long in my life that I knew what an adult was, because adults sort of acted in a different way. And I think children are confused a lot these days by the parents trying to be children again. You know, then they're chumming around with their children, you know.
I was in an American Girl store in Chicago, and the American Girl is really an interesting experience. So it started as a magazine, I think, in the 1940s or 50s, and it would tell stories about girls, you know, girls in different countries, girls in different cultures. And somebody got the bright idea of creating a line of dolls, which was based on the characters that were being written in the magazine, and it took off. And the first store that I went to is the Chicago store, which is right on Michigan Avenue. It's in the Waterplace Tower. And you went in there, and I found it really fascinating from an entrepreneurial standpoint of how they had taken one art form, which was stories in a magazine for girls, and they had turned out dolls, and the place was packed, the place was packed.
And then they had a, not a cafeteria, but they had a cafe there, and you could go in and you would see mother, daughter, and doll dressed exactly the same. And it's really, really creepy. Yes, really, really, really creepy, you know. And they'd have a little thing that you attach to the table and the doll sat in the table and they had a doll hospital there. They had ER there if it was an emergency and everything else and they did that. It was really interesting what was going on with the mothers and daughters.
No boys, you know, there's no boys, no men are in the story and everything else. But I don't find it interesting that the little girl dressed the way her mother did, but I found it really, really interesting that the mother dressed the way that the daughter did, you know. So I said, I think something's off track here. And you wonder what, you know, they're like seven, eight, nine, ten years old. What are they going to be like when they're 20?
Jeffrey Madoff: Well, I may have told this story before, but for our new listeners, when I was taking over a factory, when I started my first company, which was the clothing design company, I went to Janesville, Wisconsin, Footeville, Wisconsin. Footeville is where the factory was. I'm sure you've heard of Footeville. And the woman I was talking to who owned the building, this was in 1969 or 70. And she said, you know, this is an ongoing concern. We do two things here. We make clothes, we make dresses for creep. I said, creep, you mean committee to re-elect President Nixon? And she said, re-elect the president is what that creep stood for.
And I said, I didn't know that he wore dresses. He said, oh, no, no, no, he doesn't wear dress, like I was serious. No, no, he doesn't wear dresses, but that all the women that work on the campaign and all of that, we made these dresses for them. It was kind of a uniform, I guess. And as we walk into her office and she's talking, she said, we also make clothing for Barbie dolls. Then I see this lineup behind her desk, 25 different dolls, and I go, one of the dolls is wearing the same outfit she's wearing. And she had outfits to match every doll. And I'm thinking, this is the twilight zone. What am I doing here? This is nuts.
And I said, so you're wearing the same clothes I see as Barbie. Oh yes, I have an outfit for everyone you see behind my desk. And I said, so who's the fashion inspiration, you or Barbie? He says, oh, oh, you know, we designed the Barbie clothes, and then I like the clothes so much that I have it made for myself, too. And I'm thinking, okay, this is getting stranger. But I ended up actually renting, taking over the factory. We did not wear Barbie clothes at work, and we didn't make any more Barbie dolls. It was all my designs that were being done. But it was your American Girl story of the mother and daughter and doll dressed alike reminded me of that.
Dan Sullivan: Yeah, but if you take it through the levels of thinking, it's definitely about things, because it's about that. You talk about thinking about people, it's definitely about people. There must be an entire class of people that this is an acceptable thing. From a social standpoint, this is neat. And I bet they hang out with mothers and daughters who do more or less the same thing, and in her case, too, and think about thoughts. I'm not quite sure what thoughts it relates to, but it certainly relates to conformity and political conformity and class conformity. I don't think there's much time left over for thinking about your thinking. I think that would be like pretty full day.
Jeffrey Madoff: And see, for me, I think about when I have conversations with people like that, whether it's just walking around in New York and getting into a conversation or, you know, meeting new people or whatever, I'm always thinking, wow, what's the story here? You know, why does this person believe?
Dan Sullivan: How did it get started? My big thing is, boy, I'd be fascinated. I'm an American girl. How did that get started? I mean, it would be really, really interesting to see the birth of that as a creative, because obviously it's very creative at the beginning with the magazine, it's creative with the dolls. But at a certain point where it becomes normal or there's a conformity going out, it stops being really interesting.
Jeffrey Madoff: That's right.
Dan Sullivan: Because it's like a lot of other things. It's now joined a lot of other things. It's like, I think about it, the neighborhood where we live, it's like a small town in a big city in Toronto. It's right on the lake, so it's got sort of a summer resort quality to it. And there's lots of retail stores, you know, within three-minute walk of where I'm speaking to you, there's a lot of retail stores, you know, neighborhood retail stores and everything else. And they turn over really, really quickly. And you can see when you have a specialized dog food store. And I said, you know, so much of retail is just a hobby that got out of control.
No, I mean, they're passionate about something. They're passionate, but the world really doesn't support this, so they turn over really, really quickly, and their second mortgage didn't do it for them. But I like thinking about these things, you know, how does this whole thing get started? You know, what else is going on in their lives? This is an example of what else is going on. What else do they copy? You know, what else do they, you know, attach themselves to? I find that really interesting. And why do they?
Jeffrey Madoff: You know, I think that something may start off as a creative enterprise, but if you've met with some financial success or you're on a growth path, I think it occurs to a lot of people that they have more to lose. And when you have more to lose, the good and bad thing is you might become more thoughtful about it. But if that thought is coupled with fear, then innovation stops, spontaneity stops.
Dan Sullivan: Well, yeah, the big fear is what do other people think? I think that's a major fear about conforming behavior. What are other people going to think about this?
Jeffrey Madoff: You know, Edgar Bergen, and this is going to be Candace's father. And I think in his mind, Charlie McCarthy's father. So I was reading an interview with Candace Bergen and Charlie McCarthy.
Dan Sullivan: I used to listen to that every week on radio.
Jeffrey Madoff: I'm glad you said that because this is the first thing that blew my mind is of ventriloquist on radio. What is unique about that? And by the way, in the same thing, the Arthur Murray Dance Party, remember Arthur Murray and was it Catherine or whatever, his wife? And they taught dance on the radio. And I'm thinking, this is bizarre. And then a ventriloquist on the radio. Then, you know.
Dan Sullivan: You had to know the listeners.
Jeffrey Madoff: Yes, yeah, yeah.
Dan Sullivan: And these were popular, these went for decades. Phenomenally popular. Yeah, I mean, until television started and then they went on television.
Jeffrey Madoff: Well, Arthur Murray actually flourished on television for a while, early television.
Dan Sullivan: And I thought … Shall we, Catherine? That's how he would always start, and then they would dance together, yeah. Well, people had imaginations, they could imagine what was happening.
Jeffrey Madoff: Yeah, I think it's so interesting. I mean, Candace Bergen thought, why does this dummy have its own bedroom? You know, it's a wooden dummy, you know, but her father treated it almost like it was a son and just bizarre.
Dan Sullivan: Yeah. And well, it was definitely paying for Candace's lifestyle.
Jeffrey Madoff: That is true. That's true. You know, if so, you said there are who pays for your lifestyle, Candace, some dummy. But I think it is interesting because I also think that what comes to play in some of these things is superstition. You know, if you do something and you have a particular thought about it, you want to somehow you feel like you have to repeat the circumstances. So the next time you're in a meeting or presenting or whatever, and you want to replicate the earlier success, whether it's your lucky tie, so to speak, or whatever it is, that gets built in. And the more things that you think are responsible other than yourself, for the success of something, I think you can get into some strange behaviors.
Dan Sullivan: Yeah. Well, I have one of those. I'll be authentically, intentionally vulnerable about it here. I was born in Rocky River. It's a city suburb of Cleveland. And at two years old, we moved to the farm. And our dog died. His name was Toby. And Toby had a blanket where he lay down at night. And I had Toby's blanket. And I couldn't have Toby, but I had Toby's blanket. And it was sort of a fleecy blanket. And after a while, my mother had to cut it in two so she could wash one part while I dirtied the other one up.
And all through my life, I've had a fleecy jacket that when I go on a trip or anything, I always, and on the plane, I'll take my fleecy jacket and it's like a blanket, it's like Toby's arm. And I've had it from age two, I've had something like that. But until I tell you the story, nobody even knows that story. But what I'm saying, the same way that I tried to hold on to my favorite dog's blanket, other people have something in their childhood. And they try to hold on to it, even in their adult life. And in this case, they make a fortune actually holding on to the thing.
Jeffrey Madoff: Yeah, it becomes like a talisman.
Dan Sullivan: Yeah, it's like a talisman. And it's a connection to an earlier time in your life. I understand it.
Jeffrey Madoff: Because Margaret and I are packing up, because we're going to be moving for four months.
Dan Sullivan: That won't do me any harm, will it, what I just shared?
Jeffrey Madoff: I'm going to see, first of all, if there's a market for The Secret. And then, depending on how high that is, we'll decide.
Dan Sullivan: By the way, it's a Ralph Lauren. The one I have right now is Ralph Lauren.
Jeffrey Madoff: Where it would get weird is if you told me that Babs cut that jacket in half, so she could …
Dan Sullivan: I just wear…
Jeffrey Madoff: Yeah, the right or the left side of it. That would be weird. Yes, which with a blanket, your mom could get away with that. With a jacket, I don't think that you could. But I think we all have our superstitions and truly I consciously will fight against those because I'll think, you know, if I'm meeting with my financial advisor, I'm thinking, so you mean the tie that I wear is going to affect hundreds of billions of dollars in the stock market? Because it's not just my stock that's going down, it would be everybody else's. And as I think about it, of course, it's absurd. And so I try to let go of those things. But I think we all try to replicate favorable conditions, or what we think was favorable because we have trouble giving ourselves the responsibility for how something turns out, so to speak. There's something else going on.
Dan Sullivan: But think about it in terms of the four levels of thinking. Maybe there's a thing at the level of thinking. And to me, I don't think it was the blanket. I think it was the dog, you know, that I really liked. I'm good with dogs. I really like dogs. But at the level of thinking, maybe the talisman is an object. And at the level of people, it's a person. It could be an imaginary person. The level of thought, there's … people kill over thoughts, so we know that they hold on to things for a long time.
But here's the thing, what if you had a way of thinking and it really was your solutions to some really, really tough situations in your life and you hold on to a particular way of thinking? I'm just bringing this up as a topic, I don't have any particular example. But I think in the area of thinking, for example, I've developed one over the last four or five years, and that is try as much as possible not to put the other person on the defense when you're talking to them. Nothing turns, if they go defensive, you can't have any conversation. So I'm much more careful now than I was 10 years ago when we're in a conversation not to say something that I know is going to put the other person on the defense.
Jeffrey Madoff: Well, because I think that, let's say that we put that under the umbrella, potentially, of criticism. And, you know, it's, I think a lot of people, first of all, have a problem not taking something personally. And if it's a negative, they'll second guess themselves and try to figure out why this is being levied. And it becomes defensive. And as a result, it can also shut down communication rather than enhance the communication, which is what I'm interested in, is always enhancing the power of the collaboration, the other opinions, and so on.
So I think one of the first questions that I ask to myself is, does this person mean well? Maybe they said it clumsily, but does this person mean well? Do they have a stake in whatever they're criticizing? Do they want to bring in one of their own people? And is the criticism valid? I know when Sheldon and I are, when he's giving notes on the script for Personality, I know that he means well, no question about it. We share the same goal, which is to put the best piece of entertainment on the stage in front of our audience. And is the criticism valid? In this particular case, there's never anything he said that hasn't been worth saying and worth thinking about. Doesn't mean that we change things necessarily, but it might if we agree that this is the best thing for the play.
And I think that, for instance, our relationship on the book is getting to that point. First, you gotta just figure out, like you were saying before, just what's it like working together. We have to figure out if the two of us can dance in a way that's complimentary. But I think that that's really important when you get something thrown at you, and if it appears to be negative, the first thing is, maybe they said something clumsy, do they mean well? Is their intent to actually communicate something they think we would all agree would make it better? Or do they have some other stake in what they're criticizing? And is it valid? Does it make sense? Is it something we should try?
Dan Sullivan: Yeah. Yeah. Yeah. I think the big thing, and this sort of relates to our entire conversation today, is the person's goal to actually create something together with me, or is it their goal to defend and hold on to what they already have? That determines whether there'll be any future relationship for me. You know, to win, is there a goal to win? You know, where there's going to be a loser, not really interesting. That never goes anywhere, where it's win-lose. That's not very useful.
Jeffrey Madoff: And if you're doing a collaborative project, like a book or a play, whatever it is, if you're looking at this as, I have to prevail, I have to win, and you look at it as a binary win-lose in every different discussion you have, that's horrible to deal with. And I don't think either one of us have an interest in doing that.
Dan Sullivan: Well, it doesn't go anywhere, you know, like it's wasted time, it's wasted effort, and actually it can be losing ground. Because if I get hooked into that type of situation, I always feel lousy about it afterwards.
Jeffrey Madoff: Yeah, well, my goal is to feel engaged and excited about whatever it is I'm doing. And when I'm interviewed, people say, so who's your favorite client? Who's your favorite client? And my answer is whoever I'm doing work for now. Because that's how you want them to feel when you are doing the work. And I'm not looking to create competitive experiences among my clients. And I think every client wants to feel like when you're talking to them, you're fully present. You're thinking about what their needs are in a situation.
And again, that doesn't mean that you agree, and that doesn't mean that you give in to whatever. I think it's always important to protect the work, but you also have to look at what's really at stake here, because sometimes it's just not worth the blowback. You know, it isn't worth it. You realize, I've had a couple of times where I've actually fired clients that I just didn't want to work with. And because it never gets better with people like that.
Dan Sullivan: But the big thing is, to go back to your story about the woman who lost her point of view in the corporation, I get a sense that you're constantly strengthening your point of view, but you're open to ideas that they're different from your point of view. And you're wondering, I wonder why the person looks at it that way. That's thinking about your thinking because you're keeping everything in play. But the other thing is, if you're thinking about your thinking, the things you have are really good things. The thinking about your thinking, the people you surround yourself are really good people. And the thinking about your thinking, you're looking for thoughts that are really good thoughts.
So my sense is the one that makes everything else good for you is actually the fourth one. Because she's saying that it's really neat. We all have a central bias about how we approach each new day's experience. I've got a total bias, which has been based on a lot of successful history that got me where I was. So I'm going to stay with it until it proves not to be useful. I'm really noticing it now because of the Canada. One of the things I found interesting was Trump's comment about Canada being a state, you know, the 51st state. You know, just, it was like an earthquake up here. I mean, every day there's articles in the paper about him saying that. And in our neighborhood, I've noticed over the last week, there's about 10 Canadian flags that went up where people didn't have flags before.
And what's happened, the previous prime minister, who just was, you know, he was succeeded by a new person, said in 19, 2015, he says, you know, we're past nationalism. Countries don't really matter anymore. Borders don't really matter anymore. And I saw an absence of Canadian flag. We have one in our yard. We're Americans, but when you're in the country you're in, fly the flag where you are.
Jeffrey Madoff: When in Rome.
Dan Sullivan: Yeah, yeah, you know, just show respect. But it's really, really interesting that they've done a lot of thinking. Are you a country or not a country? And people have decided to say they are a country and not a state. I said it'd be weird if that comment on the part of another country's leader actually instills patriotism and nationalism in the country where it was being downplayed for 10 years, you know, you'd almost never see Canadian flags in the city, and now all of a sudden they're all over the place. I said, that's pretty cool, you know, that one person's comments can draw such change in other people's thinking.
Jeffrey Madoff: Well, and the degree of, and the way that the comments were made.
Dan Sullivan: Oh yeah, yeah, yeah. I said, good, yeah.
Jeffrey Madoff: Yeah. You know, I've got a real-world example of, you know, what you were saying about the new idea and thinking about it. And that was when we were in Chicago and we were going to be starting rehearsals for Personality. And the director, Sheldon Epps, and executive producer, Adam Hess, and myself were having dinner together. And Sheldon said, if you're open to it, I have an idea that might be worth trying. I said, sure, what? And he said, well, you know how Lloyd is always solving the problems. And what if in the scene when Lloyd is just burnt out from being on the road, and he comes up with the idea of what to do next, and that what to do next is to start their own club.
Dan Sullivan: Instead of that being Lloyd's idea, the turntable.
Jeffrey Madoff: That's right. Have it be Logan's idea and change the power dynamic. And I said, oh, that's a cool idea. Because to me, the idea of then having to rewrite it from a different point of view because it not only, of course, changes what Logan says, it changes how Lloyd responds. And all theater and movies or so on are action and reaction, reaction and action. And so I went back to the hotel that night and rewrote the scene and worked on it, brought it in the next morning, sent it to the stage manager actually that night so they'd see it first thing in the morning so they could have it duplicated and we could run those scenes with Lloyd and Logan.
And it really worked. And it was really fun to do. It was a great exercise. And again, those key points, does the person mean well? The answer was yes. Do they have a stake in whatever they're criticizing? Yeah, we're sharing in the responsibility of making this play and creating it. And is the person's criticism valid? Yes, we're thinking about a new way of approaching something. Not that the other wasn't working, but it could be better.
Dan Sullivan: Well, it was another dimension, because if I remember the scene correctly, one of Logan's big goals was he kind of understood where blacks could have a nightclub, which was only Harlem, and that we could be right down in the center, we could be right down in the middle, and that was a big deal.
Jeffrey Madoff: Yeah, it was huge.
Dan Sullivan: I forget, what was it, 42nd Street? Where was it?
Jeffrey Madoff: I don't know. 52nd Street.
Dan Sullivan: Fifty-second, yeah. So you're right, you know, you're right in the theater district and everything else. But I remember it because he understood what the dynamics were of the geography of New York. Who could be here and who couldn't be there and everything, of course. Of course, it ends tragically, but yeah, it was terrific.
Jeffrey Madoff: And so that kind of thing to me is actually fun.
Dan Sullivan: Yeah, well, the big thing here is if you think about your thinking, you're gonna come up with new ideas, okay? If you're with someone else who thinks about their thinking, you'll have two new ideas, and then you can have a third idea that's better than the first two.
Jeffrey Madoff: Yes.
Dan Sullivan: And that only happens at the fourth level, it doesn't happen at the first level, second level, or the third level.
Jeffrey Madoff: And that to me sounds like a very good wrap up.
Dan Sullivan: No, but it's true. I mean, it's been happening all along as we've been putting this together. Oh, that's a great idea. Let's do that. Yeah, well, you never learn less.
Jeffrey Madoff: That's true. That's true. And I think to me, that surprise and that discovery, I think if you hold on to your ideas, I think you should hold on to your integrity with white knuckles. Squeezing that and always holding on to your integrity, because you can only compromise that once. And then you're compromised for life. But I think in terms of investigating ideas and thinking about thinking, I think that if you're open to the challenge of rethinking, because maybe it might be better. Maybe it's the fourth iteration that is better, but that idea is what inspired the change in the first place. It's not about, well, that was mine and that was his, and this was my idea and that. It's not about that. It's the work we're doing together is getting better and better.
Dan Sullivan: Yeah, and it also explains why the woman at the corporation, why she couldn't answer your question because she compromised her integrity long before you talked to her. The first time that she didn't have a point of view in a meeting was the beginning of her not being even able to have an answer in her mind for you.
Jeffrey Madoff: And the interesting postscript to that was, when I said that to her, that you don't know your own opinion anymore, you don't know what you think, what happened?
Dan Sullivan: She had to leave.
Jeffrey Madoff: She did, that's right. She left like three months ago.
Dan Sullivan: Well, good for her because she could have kept going down the slope.
Jeffrey Madoff: That's right. And she started her own business. Yeah.
Dan Sullivan: Well, my feeling is that if you want to be in the business of having an opinion of your own, don't work in a large corporation.
Jeffrey Madoff: Yeah, I mean, I'm grateful there are people that do all the things that I'd rather not do. And take care of things I'd rather not take care of. But I think when we're speaking to the audience that I think we're speaking to, which is creatives and entrepreneurs, you know, hopefully we're giving them ways to think about their thinking.
Dan Sullivan: Yeah. Yep.
Jeffrey Madoff: It was great. Thanks for joining us today on our show, Anything and Everything. If you enjoyed it, please share it with a friend. For more about me and my work, visit acreativecareer.com and madoffproductions.com. To learn more about Dan and Strategic Coach, visit strategiccoach.com.
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