What It Means To Think Beyond The Algorithm
February 24, 2026
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What happens when technology stops asking us to use our brains, our imagination, and our judgment? Dan Sullivan and Jeffrey Madoff trace the journey from radio and early television to social media and AI, and show entrepreneurs how to stay uniquely human, think critically, and build theatrical companies that technology can’t compete with.
Show Notes:
The shift from radio to television showed how adding visuals can change our engagement with a story, sometimes in ways that make us more passive as audiences.
Music videos and MTV forced musicians to become visual content creators, even when their real talent and passion were in the music itself.
If you rely on technology as your main point of differentiation, you lock yourself into constant, exhausting adaptation as the tools change overnight.
Treat social platforms as corporate media, not “social” spaces, and remember that if the service is free, you and your attention are actually the product being sold.
Algorithms tend to amplify negative, alarming content because it gets more attention and clicks, even though it often harms people’s thinking and mood.
Our brains are more reactive to perceived threats and negativity than to calm, positive information.
Great companies are built by entrepreneurs who cast people for roles based on character, potential, and fit, not just past experience or static job definitions.
Entrepreneurs also need to consciously recast themselves over time so their role stays aligned with what they do best and find most meaningful.
What many people label a “crisis” is often just a loss of convenience or comfort, which is a sign of how little real adversity they have had to face.
Technology consistently eliminates repetitive heavy labor, but it doesn’t automatically produce more creativity or fulfillment—those require personal choice and intention.
Resources:
Casting Not Hiring by Dan Sullivan and Jeffrey Madoff
Your Business Is A Theater Production: Your Back Stage Shouldn’t Show On The Front Stage
The Road to Serfdom by F.A. Hayek
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.
Dan Sullivan: Jeff, I was just telling something, and you will relate to the experience and to the decade that it happened in, but in the 1940s, our family didn't have television, and there wasn't much television in the ‘40s, not near Cleveland. And I remember there were three programs that were like four o'clock, five o'clock in the afternoon programs when you got back from school, and it was The Lone Ranger, it was Sky King, and it was Sergeant Preston of the Yukon, and I used to listen to those programs avidly, avidly. I would always make sure I was there to listen to them. And then when we got into the ‘50s and we got television, well, those programs made the crossover between radio and television. And I noticed that whereas I was an avid listener to the radio programs, I wasn't an avid watcher of their television versions. And I've been reflecting, because of the book that we're writing, Casting Not Hiring, and the whole notion of making your business into a theatrical enterprise, that there's something about when a technology comes along and it doesn't require you to use your brain, it doesn't require you to use your intuition and your imagination. It's not as interesting as when they tried to do the whole thing for you. And now AI will do everything for you. And I just wonder if it does anything for your brain. Probably diminishes it.
Jeffrey Madoff: I think it takes its toll. It's funny, the first shift that I had were the visuals, occasionally lived up to expectation, not expectation, but yeah, I guess lived up to the imagination is when MTV came on the scene. And all of a sudden it was required of musicians to create these little, you know, basically they're advertisements for the album, but to create these things, some of them were fun to look at for sure. But I really didn't like the fact that I like doing the imaginary work myself. All I want to do is hear the music. And there were exceptions, you know, the Beatles when they did “Yellow Submarine,” and it was just, you know, an incredible creative collaboration between the images we saw, the artists who created the music, who were also instrumental in creating the visuals, at least giving the okays for it and everything else. But for the most part, I thought it diminished because it made it a necessity for fantastically talented musicians to do things visually, which is not what they either wanted to do; in most cases, they didn't want to do it. But in order to be competitive for the audience, you had to do it. Maybe it's that, you know, we got a TV, even though there's only five years between you and I, those five years from the late ‘40s to early ‘50s, I think the growth of television was phenomenal during that time. So I didn't really go through the listening to the stuff on radio, but that hit me strongly during the birth of MTV and how that changed things, and I don't think for the better.
Dan Sullivan: Yeah, so I was noticing there's a new AI app. Google has one, it's called Anna Banana, and then there's another one called Sora. And anything that you tell them, they'll recreate the vision. And I was watching it, and people were saying, isn't that amazing? And I said, I find it boring within five seconds, okay? Because it's an algorithm. It's an algorithm that's doing it. I'm just wondering, as far as our book goes, we're saying that if you're using technology to differentiate yourself in the marketplace, you're going to be really busy day-to-day adjusting to what happens overnight. But if you think about your entire company, both back stage and front stage as theater, where there's constant growth of talent, there's constant growth of teamwork, there's constant growth of presentation, I think you're going to be much more unique in the marketplace than someone who's trying to do it with technology. I think that's true.
Jeffrey Madoff: My niece's husband, he's an editor, he does, you know, TV and movies, and he finished this two-month project. They're giving him basically documents and turn these things into commercials, you know, for online commercials. Forgetting about all the shortcomings that will eventually be overcome in terms of the creation, like just character consistency and scene consistency and all those things, which are getting better but still really hard, there is a hollowness to the visual that is, in some cases, when it's simple visuals, harder to tell whether it's a real person or not, which I think is a whole other barge load of problems, you know, in terms of that. But, you know, it makes me think about, so first we had books, but the oral tradition continued for some time. And then all of a sudden books started to have illustrations. I loved comic books. I still like comic books and graphic novels because that was integral to the message of the artist and the person who wrote the book. It was kind of like, you know, the person who wrote the book in some cases got to be like a film director in terms of, you know, what the scene would look like or something like that. There've always been things that have shifted how we hear a story, interpret a story; even who ends up starring in the film, you know, affects how we view the story and all of that.
But I think that, I don't know, I've always liked coming up with my own visuals. There are those exceptions where I really enjoy because it's truly a creative artist who did something. But you know, those people who say, you know, we'll take the transcript and we'll spit out 50 commercials in two seconds, you know, we're inundated with enough crap. Before we started recording today, I was saying to you how I find it actually offensive that I have to opt out, and it's not so easy to opt out of just AI imposing itself on every email and summarizing the messages and all that. I don't need that. I can reread it if I want to. And it can be very misleading how it condenses what the messaging is. But it's getting harder and harder to get away from it. And I think there's going to be a movement about that because it's, I don't know, I don't even know how to classify it yet other than it's intrusive. And we don't have any control over that at this point.
Dan Sullivan: When I first came to Toronto in the 1970s, just through odd circumstance, I got a chance to meet Marshall McLuhan, professor at the University of Toronto and one of the most famous academics in the history of Canada. And he was actually an English professor. You know, he taught the English literature and everything. And he brought out this book, which put him on the map. It was called The Gutenberg Galaxy. And then he came up with a line, and it's the line that he came up with that I'm thinking here, and that is that the medium is the message. And I was thinking about, you know, social media, I was thinking about AI and everything, that whatever they say is the story that they're presenting, the story isn't the message. What they're doing to you is the message.
Jeffrey Madoff: I agree. I mean, McLuhan ended up being right. Of course, he was even right before he uttered that, that the medium is the message. First of all, I always resented that it was called social media. And I would say to my students at Parsons, this is not social media. This is advertising. It's corporate media. And just like with television, going back to that model that, you know, it was a lot easier back then, but you had three stations essentially. So through those three stations, it was the aggregation of eyeballs and the competition among the three of them for advertisers during prime time and all that, because the more eyeballs you aggregate, the more you can charge people that advertise on your particular platform. And this stuff is never free. In this case, to me, it's just the product.
Dan Sullivan: Yeah. If it's free, you're the product.
Jeffrey Madoff: That's right. That's right.
Dan Sullivan: Yeah. If they're giving it to you free, then they're selling you to somebody else.
Jeffrey Madoff: Well, it's also interesting is now with AI, you can opt out. They will archive your stuff. But if they archive your stuff, and by they, I mean ChatGPT or Claude or Gemini or any of those, then they can use whatever content you put into it. They can basically use your content. I don't want that. I don't want my content to be used that way. I mean, the way that I've been using AI is basically as kind of an idiot savant researcher that if there's anything that piques your interest in the research that you want to use, you need to vet it separately. Because as the term goes, it hallucinates. And I've come across that. I'll bet you …
Dan Sullivan: What would be an example of that?
Jeffrey Madoff: You get a statistic, and the statistic doesn't quite sound right. Anything that I would quote from a study, or that a person is quoted, I want those sources verified. And if it can't be verified, I won't include it in what I'm writing. And so I would get a quote and I would ask for verification of the quote, and I would literally get a message, I'm sorry, I cannot verify that quote, it shouldn't be used. And I'm thinking, well, so why was this sent to me? But we've learned, even with email, because all you have to do is click it to forward it, that people don't vet information. Most people don't vet information, which I think is very irresponsible. If you're going to be passing it along to other people, then you should be vetting that information before you pass it along. And that happens constantly. And I've talked to lots of people who are way more knowledgeable about AI than I and are using it way, way more than I am. But I mentioned, oh, yeah, yeah, that happens 15, 20% of the time. You don't vet it. You can be sending out misinformation.
Dan Sullivan: Yeah. So I have a question about that. Do you think we ever did? Before the present technologies, did people ever vet information or did they just very easily pass on what they had heard?
Jeffrey Madoff: Well, I think it depends on who you're talking about. So, you know, I think, for instance, if you worked for a respected publication or you were on a TV network and you were Walter Cronkite or Edward R. Murrow or whoever, there were rules and thresholds for being verified that you had to clear before something would be published. Now, that doesn't mean there wasn't yellow journalism and all the rags and all that kind of stuff that pass on misinformation. I think that's been going on forever. It's not new. But I think what's relatively new is an individual can be in a position to all of a sudden send out several thousand emails.
Dan Sullivan: A million.
Jeffrey Madoff: Yeah, that's right.
Dan Sullivan: To a certain extent, you know, if you're Joe Rogan and you have a hundred million, you’re passing on, I heard it on Joe Rogan. But I'm just wondering in the scheme of things … like, I've never been on social media. Like, I'm an outputter of social media, but I'm not an inputter of social media. In other words, we use social media as a broadcast medium. So, you know, I'll do long podcasts and, you know, or I'll do interviews and they'll take sections of the interview and they blast it out on Facebook and the other social media. But I've never actually been on the receiving end of social media. I remember when it first started being talked about was sort of 2005, 2006, you know, that you could do this and people would chat back and forth and they would send things, keep each other updated throughout the day. And I said, well, I don't do that in real life, so why would I do it in digital life? But the other thing is I'm averse to gossip. I'm very, very averse to gossip. In other words, I have a rule that if somebody tells me something, it ends with me unless they ask me to tell somebody else. Like I never pass on anything. In a private conversation that somebody tells me, I never pass it on. And then when other people pass something on to me, I say, that's not going any further than me.
And it's both a personal thing, but it's also a professional thing that we have team members inside Strategic Coach who are called Program Advisors. And they're in-between workshop connectors with the company. They're not experts on anybody's business, but they are experts on the Program. They are experts on how the Program works. So somebody will say, the clients don't like this latest thing that you did, that they'll come to a meeting, the clients really don't like this. And I said, how many clients don't like it? And they said, well, you know, a lot of them. And I said, can you attach a number to lot? And it's three. That's three. Okay. And we're talking about three out of hundreds. So it's small. And I said, so the question I have, they don't like it. But my question is, what's your role in this? Are you a messenger from the clients to us, or are you our representative to the clients? Okay, I mean, are you a union steward for the clients? You know, talking to management.
And generally, if I have two or three encounters with them like this, they clean up their act, they don't pass me on information, and I said, they'll have a conversation about the workshop, they'll come and ask me about a particular concept that I'm talking about, and they say, could you explain to me what the concept really is, because I'm getting questions that I'd like to be in a position to answer. But I just cut it off, because it's like a, do you know what a Newton machine is?
Jeffrey Madoff: The Newt machine?
Dan Sullivan: Yeah, it's a rack, and it's got balls, and you take one ball, and you go like this.
Jeffrey Madoff: Yeah, yeah.
Dan Sullivan: And I said a lot of humans are like a Newton machine. They just walk, you know, like a rumor just goes through 10 people and it comes out the other end and everything like that. So I'm just wondering, and, you know, before we had our technological concepts in small communities where people would see each other personally, were they any better at vetting information than they are today?
Jeffrey Madoff: Well, so I think back, people couldn't read. The majority of people couldn't read. So things were passed orally. And, you know, from playing telephone when you're a kid at birthday parties, doesn't take very long for the message to get horribly corrupted from what it was originally. And the more it gets spread, the more corrupted it gets. And, you know, then as more people are able to read, there would be one-sheets, which were basically the newspaper headlines in the town square that people would look at. And I think that it makes me wonder, what was the birth of critical thinking? I believe initially the communication had to do with survival, you know, and as language began to get codified, then it was able to be printed and mass printed and distributed. I know that in philosophy, which was, I had a double major in philosophy and psychology, and what I liked about them is that you had to show your process in terms of, how did you reach the conclusion you reached and what you're talking about? That was in college where I had that.
I think that critical thinking has always been important, you know, because how do you discern what's fact from what's fiction? What's misinformation as opposed to lies? Whose agenda is this serving? All those kinds of things. I know that because I've been on the receiving end, how there are people that because this confirms their own bias and it appeared in print somewhere or somebody said it, oftentimes it's even the wrong attribution, and it gets distributed all over the place. And I think that people are unfortunately, I think, lazy, intellectually lazy. And if something reinforces what their belief is, I think that they will pass that along without questioning what their belief is or what the source of that information was. And I think that's a disservice if you're sending it to friends or out to your wider platform audience. I think that, you know, I wish that people had more of a sense of duty to vet the information before they pass it along. And that's not a political statement. That's just a statement of, how do you vet information? Why would you pass something on if you don't know what's true? But, you know, the negative information, as we know, most people are fed much more negative than positive information via the algorithms because they get more clicks and it becomes self-proving that it gets more.
Dan Sullivan: It also appeals to a different part of the brain.
Jeffrey Madoff: Yeah. Yes.
Dan Sullivan: I mean, it's easier to appeal to the back of the brain than it is to the frontal cortex.
Jeffrey Madoff: I don't know which is easier to appeal to, but we do know that negative gets more attention. This has, I guess, been forever. Negative gets more attention than positive, whether it's because it's titillating or whether it's because it could save you your life.
Dan Sullivan: Well, it's only recently in human history that we have relative safety. I'm reading this long, very, very interesting novel. It's by a writer in Great Britain. I think I've mentioned it. But he doesn't write for them to be manufactured as books. He just writes them in their Kindle format, and they just go to Kindle. You can order The Signal on Amazon, but you can't order the book on Amazon. And his name is Andrew Wareham. He has this book, and it starts around 1820. It's in Great Britain, and it goes to about 1850. That's a 30-year period, and it's right at the breakout of the Industrial Revolution in Great Britain, you know, where for the first time metallurgy has gotten very good, they're starting to make steam engines, they're starting to lay track, they're starting to create steam-powered boats. It's really quite extraordinary to see the whole revolution described just in dialogue of people talking about their ordinary lives and the class system in Great Britain, so that you have certain characters who represent the very privileged and very wealthy, and you have people who are laborers. And he captures the language, that they had different language and they had different experiences. The interesting thing about it is that nobody had a handle on the era that they were living in, from top to bottom of society. And I thought about that and I said, nor does anyone today have a handle on the era that we're living in.
Jeffrey Madoff: Well, I think we sort of make sense of things after the fact.
Dan Sullivan: Yeah. Now, we have a long run. We have about 70, 80 decades of experience that we can bounce things off of. And that gives us, I think, a broader context for understanding. There's massive change. Things have never changed like this. And I said, yeah, yeah, I've had experience of going from radio to television, you know, going from thinking that your father's 40-mile-an-hour car was fast, you know, and then finding out what fast really meant and everything like that. But the interesting is that there's a popular phrase, you can't be inside the jar and know what's on the label. We're all living inside of an experience and nobody's got an overview of what the whole experience actually looks like. Each of us just has the way that we've gotten used to living in the times that we live in. And we have a bias towards what we like and we have a bias against what we don't like.
Jeffrey Madoff: Yeah, and when you say, you know, like going from radio to television, I would take it a step backwards and going from basically just people talking in the town square to radio, there was like, nothing. So people's sources, all of a sudden you start putting together, other than religious services, I'm just thinking out loud here, other than religious services, there was no ritual for an audience. I actually, believe it or not, yesterday watched two episodes of The Lone Ranger. I hadn't seen that show for, I don't know how long, which was interesting to see. But anyhow, those stories that we were told, the antecedents of those stories, I mean, Fran Stryker wrote the books about The Lone Ranger. And it was first a book, and then it was the radio program that you listened to, and then it became, I think it was the same actor, Clayton Moore, I think, played.
Dan Sullivan: And Jay Silverhills was Tonto.
Jeffrey Madoff: Yes, yes. Lenny Bruce had a great joke about Tonto and the Lone Ranger, and it's Tonto and the Lone Ranger are surrounded by Indians, hostile Indians.
Dan Sullivan: All sides.
Jeffrey Madoff: Yes, all sides, they were surrounded.
Dan Sullivan: Indians on the north, Indians on the left.
Jeffrey Madoff: Yes, and he goes, Tonto, it looks like we have problems. And Tonto goes, what do you mean, we?
Dan Sullivan: White man.
Jeffrey Madoff: That's right.
Dan Sullivan: Yeah. Well, I'll give you an example. You know, this is 1941, but my mother was living out in the country in a home, and they didn't have radio, they didn't have telephone, and they didn't get a paper, and she didn't know about Pearl Harbor for days. It was only when she went to church on Sunday that she found out about Pearl Harbor. The next Sunday, actually. Now you know it instantaneously.
Jeffrey Madoff: Right. I mean, if you've got a phone, you get the news bulletin, which I also don't think is necessarily a good idea either, but that's not going to change. You know, what is information? And what do we need to know and how soon do we need to know it? But I do think my old saw is critical thinking. Most people don't question because it requires you to do something if you're going to actually vet the information. And I don't think most people are disposed towards doing any more work than they have to do to get through their day.
Dan Sullivan: Now, are you talking about information that's important to them or information that's just passing through? Because a lot of people are really good about information that's really important to them. In other words, it makes a difference in the day whether they have the right information or the wrong information.
Jeffrey Madoff: And I would say that you just spoke to the issue of local news. And people want to know when they leave the house—before they leave, they want to know what the weather is going to be, what the traffic conditions are on their route to work, and maybe if the hometown professional team or college team won the game. And that's more important than anything else to them at this point.
Dan Sullivan: I don't know what you call it where you are, but it's called Radio 830. And it's every half hour is news, weather, and sports.
Jeffrey Madoff: Yeah, I forget what it was called.
Dan Sullivan: It's not news, weather, and sports. It's traffic, weather, and sports.
Jeffrey Madoff: Right. Yes.
Dan Sullivan: It's not news.
Jeffrey Madoff: That's right.
Dan Sullivan: It's traffic, weather, and sports.
Jeffrey Madoff: Right.
Dan Sullivan: Yeah.
Jeffrey Madoff: Which was the backbone of local newspapers and the classified ads. You know, that was the backbone of that. I can't remember which radio station it was, but they had a very catchy slogan, give us five minutes, we'll give you the world.
Dan Sullivan: There's a very interesting economist, F.A. Hayek. Do you know F.A. Hayek?
Jeffrey Madoff: No, I don't.
Dan Sullivan: The Austrian, ‘30s, ‘40s, ‘50, won the Nobel Prize for a book called The Road to Serfdom. And he said that one of the things you have to understand about knowledge, he said that very little of what makes the world run and work is actually tacit knowledge. And this affects our book. This really relates to our book. He says tacit knowledge is knowledge that can be known by a wide number of people in more or less a theoretical way. In other words, it wouldn't be involving them personally. Political news for the most part is sort of tacit knowledge. The stock market is sort of tacit knowledge. It's organized in a particular way, it's packaged, and it's sent out to other things. And he said that that represents about 1% of what's needed to make the world run every day. But everybody has implicit knowledge about how they get their job done, how they get up in the morning, how they operate in their local areas.
So to bring it back to your topic of local area, he said, if you took all the academics in the world and put together all the knowledge, it would represent 1% of what the world needs to actually operate every day. You know, the teamwork that's required to get this done, the teamwork that's required to get this. And I think in our book, we're suggesting that if you run your company by job descriptions, you have very, very little of the knowledge that's actually very, very necessary for that to be a successful company. The phrase that I use in my section of the book is that job descriptions are blueprints for compliance. Here's the blueprint, and if you don't stick to this blueprint, you're going to be in trouble. Sticking to the blueprint 100% means that you're acceptable. Failing your blueprint in any way means that you're in trouble. And yet what we're suggesting is an approach, a theater approach, where everybody has a role and it's their job every day to continually adjust their role to everyone else's role, and then to the project of the team and then the project of the teams to the company. And there's this constant adjusting every day with new information and new understanding and new insights.
Jeffrey Madoff: Yeah, and that requires clear communication, not with messages you're getting on your screen, but with colleagues.
Dan Sullivan: Or three unhappy clients. Three out of 300 unhappy clients means that the clients are unhappy, yeah.
Jeffrey Madoff: Sometimes I will look, if I'm looking at a particular thing to buy, and I'll look at some of the reviews of them. And I'll look at, you know, the top reviews, I'll look at the worst reviews. And I realized a lot of times the worst reviews are things that the package arrived damaged. Well, it tells me nothing about the product. Why would you post that? It's meaningless. But what we're doing in the book is trying to give a sense of a dynamic process that a primary feature is the ability to be nimble, respond quickly, and not be boxed in by the traditional roles.
Dan Sullivan: Or jobs, job descriptions.
Jeffrey Madoff: Yes, job descriptions and that, as you rightly put it, then it becomes about compliance. You know what to do in this situation, but what if it's not exactly that situation? You know, how do you parry with it and bring about a positive result for your business? On one hand, I think we're getting further and further away from that. Try to get somebody on the phone, an actual human on the phone to solve a problem. And with any large company, it's staggeringly frustrating. I tried with Con Edison in New York when I was subletting while we were having our renovation done. So I was paying the utility bill at that residence, and then my payments ended at the end of August. Notified them to turn it off. I'm getting bills. I cannot get a human on the phone. Their voice prompts don't relate to this at all.
Dan Sullivan: Yeah, maybe that's the message.
Jeffrey Madoff: That's right. That's right. And basically, the message is we don't want to be bothered. Please write a check. Yes, we don't want to be bothered with this. But I think that the main thing we're talking about also is going back to, it makes me think of my parents and their stores, is we're actually going back to a way of doing business, which is that you did business with people you knew, who you had a connection with, you were members of the same community. And my parents and their stores knew their customers. They liked, they knew what they didn't like, they give them a call, some came in, you should come see this, I think you would enjoy it. It wasn't all process. And I think process like that becomes very, very limiting if you're only giving people the instruction of how to comply to a particular situation, not get in trouble.
Dan Sullivan: Yeah, I think there's really something about process, and we mention in it that things should be done by projects that have a beginning, a middle, and an end, so that you can learn from how you started, how you followed through, and how you finished, and then have another project where you can improve the impact and the quality of the project. So I do a book every quarter, and this is my 45th quarter, and I was just struck by how, you know, it started with me, with nobody, and now we have 10 people on the team who do something during the quarter to deliver the finished product. And I was just struck by how much each of us has improved teamwork with everybody else on the team. But the structure is always the same, but the content is always different, and it's got a theatrical feeling to it.
Jeffrey Madoff: Which has basically been the way you have been, the way Strategic Coach has been. And, you know, taking our theater comparison is, a few years ago, you were giving a performance on the stage.
Dan Sullivan: And I created roadshows.
Jeffrey Madoff: That's right.
Dan Sullivan: Then I credited somebody else on payday. Then we took it on the road.
Jeffrey Madoff: Yes, we took it on the road. Well, who's going to play Dan? Brad Pitt is booked. But you know, something that maybe our next podcast would get into, which I think could be interesting, is we're talking about the casting, not hiring, but the one person that we're not talking about casting, which is essential, is that entrepreneur, that founder.
Dan Sullivan: Yeah, well, I do that in my section.
Jeffrey Madoff: Oh, okay, cool, that's great. Because the most important decision you're gonna make is, how are you gonna cast yourself? What are you gonna do? And I think as we get older, we're different than we were. We know more. We also know more like what we like to do and what we don't wanna be doing. And if the book is talking about casting people for roles based on their character and potential and fit, well, who am I now in my company? I love the work that I did, traveled the world, worked with great people, all of that. But at a certain point, it wasn't as interesting to me. The play became something that was a creative, intellectual, and business challenge to try to bring to life and do. And that was more exciting to me. And because I was at that time 71, the notion of, if not now, when, came to my mind.
Dan Sullivan: The difference that I would make is that you're the leader and everybody else is management. The way the show is now, okay, not eight years ago, not the various, or your leadership role has been freed up to constantly be thinking about the next step for the play, okay? The director, the choreographer, the musician, is to make sure that we're maximizing what we already have.
Jeffrey Madoff: That's right. And what comes along with that, and you and I did a whole program about it a while ago, is at what point, if ever, at what point do you take your final bow? We've talked about how retirement to neither one of us is anything that's appealing at all. But there's nothing to matter with it if somebody hits a point where, and let's assume their health is good and financially they don't have to work, then the question is, well, why are you doing what you're doing? If it's still giving you fulfillment, satisfaction, keeping you active in ways you want and all that, that's great. But there are other people that make the decision, like a good friend of mine, who he's now making four trips a year to do humanitarian efforts, whether it's help build schools or whatever. That's fulfilling to him. His role has changed from being a CEO in a housewares company to doing this humanitarian work, which is fantastic. And he finds, you know, it's not through one organization. He does it through different organizations, finds things to do. That's cool. That's nothing I would do, but I have respect for him that he's doing that. And he has recast himself in a different role at age, you know, he's also 76. We also should turn the mirror on ourselves.
Dan Sullivan: Yeah, well, there's some indicators. One is that you're in the way. In other words, that you're now becoming a problem that interferes with the success of what you've created. And I've seen that. I've seen that where the entrepreneur, there's a phrase that's been brought up 20 times over the years in Strategic Coach, you know, what would you say your number one skill is? And I say, I'm really good at putting out fires. And I says, that's the total description of an arsonist. I said, you create the fire and then you put it out and you're a hero. Meanwhile, things got destroyed. But the other thing is, it goes back to that fundamental question that I used, do you have a future that's bigger than your past? In other words, your future of the company that you're working on, does it have a bigger future than we've already experienced? And do you, and what you're doing in the company, is your future importance more important than your past importance?
Jeffrey Madoff: You just kind of feel, you know, been there, done that. Yeah, then it's over. And so I think a lot of people don't look at that question. If you don't look at that question at a certain point, the options are gonna be taken away. You may be dealing with a failure in your health. You know, how can I say this? I think you have to act on the options before the options run out for you. Because at a certain point they will. So, you know, what can you do? And what do you want to do? And I think, you know, if you've worked hard your whole life and you decide, you know, something for whatever time I have, I want to do things different. I want to do humanitarian work. I want to write that novel. I want to take a photo safari across the United States. Whatever the hell it is, it's fine. But I think it's important to think about how we as individuals who founded a business like you and Babs did, like I did, like our friend Joe Polish, is that the role you want to continue to play?
Dan Sullivan: And the other thing was, to what degree was the company that you created a creative learning experience that had no destination? It was just a constant growth process that you're in. Okay. Or, the company you created was an opportunity to make as much money so you could stop doing it. And people are wired differently on that particular topic.
Jeffrey Madoff: Well, that's right. Interesting that according to a Harvard Business School study, 72% of people who decided to retire, and these are people that were successful, made lots of money, all of that, suffer from more depression as a group because they sort of don't know who they are or what their role is anymore. That was a staggering, that's almost three quarters. That's a staggering statistic.
Dan Sullivan: Why do you think? I mean, neither of us have done it, so we don't have the experience. I mean, what was it about what they left and got away that they're not experiencing something now after retirement that they did while they were still working? What is it that they are missing?
Jeffrey Madoff: A sense of purpose.
Dan Sullivan: That's one.
Jeffrey Madoff: I think that's a big part, a sense of their identity as it relates to that purpose.
Dan Sullivan: Two.
Jeffrey Madoff: And we are assuming that it's not an issue of money.
Dan Sullivan: That’s three.
Jeffrey Madoff: Nor that the option has been removed because of just ill health or whatever. You know, that's something else. So what would you have …
Dan Sullivan: You’re up to three. I mean meaning, identity. These are not trifle things.
Jeffrey Madoff: No, but I also think that a lot of people don't self-reflect on that at all.
Dan Sullivan: I think a lot of people don't self-reflect.
Jeffrey Madoff: That's right.
Dan Sullivan: Not just on that.
Jeffrey Madoff: That's correct, that's correct.
Dan Sullivan: You know what I noticed about that? I ask questions and we have thinking tools in Coach that they're philosophically pretty deep. They're psychologically pretty deep. I have a new tool I'm creating that I'm gonna test in a couple of weeks. It's called What's Worth Waiting For? And then you do a history in your life so far, what's been worth waiting for. In other words, you didn't get it right away, and Babs was worth waiting for, you know, creating the company was worth waiting for. You know, I mean, I've got a whole list of that. And then say, that's sort of in the past, and it's in the present, so you're enjoying it. But then the next column is new possibilities of things that might be worth waiting for, and you do that. And then you start putting them together, and you begin to realize that of all the things that you appreciate most, some of the most important are the things that were worth waiting for. You had to go through a lot of experience. You had to go through a lot of trial and error. There was a period of investment where you didn't see a return and everything like that. That's just normal thinking in Strategic Coach, you know. But I remember I was giving a public presentation and we got into something and said, boy, this is getting really deep. And I said, deep? Hmm, that's an interesting concept, deep. And what you realize that most people never think deeply about anything except in response to a severe crisis. Or you could have stopped it about anything.
Jeffrey Madoff: Yeah, yeah. Well, a crisis forces you. It forces your attention. You know, I mean, you kind of don't have the option to ignore it, because then you're dealing by its nature being a crisis survival.
Dan Sullivan: But I think that, you know, I'm always thinking of new book titles because I committed to writing 100 quarterly books and I'm at 45, so I've got 55 more to write. I was just thinking that a loss of convenience and comfort is a crisis to a lot of people. That's just how fast a crisis can happen to a lot of people, is that they're put into an experience of discomfort or it's inconvenient.
Jeffrey Madoff: Right. Well, yeah, I think I mentioned when I was on an airplane and this guy was getting all pissed off and angry at the flight attendant because the Wi-Fi wasn't working.
Dan Sullivan: Meanwhile, he's at 35,000 feet, he's traveling at 500 miles an hour, and he's sitting in a lounge chair, and he's probably being served beverages.
Jeffrey Madoff: Yes. In this case, probably too many of the wrong kind. But that's right. But it's like, wow, you think that's a problem?
Dan Sullivan: Yeah.
Jeffrey Madoff: You're being inconvenienced. And of course you want everyone on the plane to hear about it because you're yelling at this stewardess who can't do anything about it. What is a crisis? You know, if that's the nature of your crisis, you've got a pretty good life that you're not appreciating. That's what upsets you.
Dan Sullivan: Yeah, unhappiness is a bad habit. Do you suspect that AI, I mean, we talk about the dangers of AI, but properly utilized and properly understood, do you believe that AI will actually free people up to go back, you know, it's that phrase, systematize the predictable so that you can humanize the exceptional? Do you think, I mean properly think, that it'll actually allow us to really humanize all sorts of situations that we haven't been able to do it because our efforts were required to keep the system going?
Jeffrey Madoff: No, I don't. I don't. And the reason that I don't is I think that we're talking about issues having to do with human nature. And I don't think that changes.
Dan Sullivan: I'm not saying everybody can do it, but can you do it? I don't think the human race is ever going to do anything. There goes the human race. It's been going for a long time. There's probably some tricks to it, you know, that we have, you know, but I just wonder if, you know, because we're suggesting actually in the book that that's true, that there's a way of making this activity of having an entrepreneurial company in the marketplace, in a marketplace that's being more and more pervasively impacted by AI, that there's a way of really making this much more enjoyable.
Jeffrey Madoff: What I think is that the more you can eliminate the meaningless routines, be that through AI or be that through just a better structure of the business, and I think we're suggesting a structure of the business that is both practical and can be profitable, and I think that that in and of itself is really important. But I don't know that it used to take people three days to go buy a wagon somewhere that you can now go in a few hours in a car. Did that free up time for, I think there's always been times where repetitive heavy labor has been replaced by some kind of advance. Did that somehow cause a rising tide of creativity and innovation? I don't think so. I mean, in all the emails and crap that I get about, you know, filling my sales pipeline, being more productive, all of that, I think there's been this whole push on productivity. And to what end? How are you defining productivity? And to what end is all that productivity? Is it bringing you more pleasure? Is it making your life better? Is it making other people's lives better? I mean, you know, what is it? So I don't, when I hear things, this will make everybody's life better.
Dan Sullivan: I didn't say that. I didn't say everybody's life. I'm saying is the opportunity there for an individual who wants to look at it this way to actually get freed up from a lot of things.
Jeffrey Madoff: If you are predisposed to looking at things that way, whether it's AI or something else, I think that, you know, that means that you're on the lookout. And I think that being on the lookout will lead you. Does that make sense?
Dan Sullivan: Yeah. I don't think that humanity improves on a society-wide basis. I think it improves on an individual basis, that that individual influences other people who want to do the same thing, and there's a critical mass of movement among a small group of people. You know that because you've lived that life of people who are interested in great production, great video work, and everything like that. Well, not everybody's doing it, but certain people are doing it. Because I've only focused on one thing since I got involved with AI, and I've only involved myself with one AI program. I've gone to the higher levels of it, where it's not free anymore and it's $200 a month. But I've been very, very pleased with the amount of structured thinking and action that I can do with AI compared with what I could do two years ago.
Jeffrey Madoff: Yeah, I mean, I think that, look, just the ability to go online, forgetting AI for a moment, we can go back years. The mere fact that you could go online and do fairly sophisticated and large amounts of research, you know, that was great. And can AI help that? Yes, again, as long as you also pay attention to the hallucinations you may get in the results of some of this stuff. But, you know, it's interesting. I think of putting technology together. You've got a mobile phone and you've got GPS. We can do a car service that you can use that mobile phone. We can pinpoint your location. We can get you from A to B. And you know, what did that do? It opened up a way of operating on a daily basis. Maybe you don't need a car. You could do that. I mean, I honestly, although driving was fine with me, but I don't care if I don't drive. I'm happy not to.
Dan Sullivan: Yeah, I haven't driven in the city in 20 years.
Jeffrey Madoff: Right. And, you know, we were just in South Carolina and we stayed at this Airbnb for Thanksgiving, you know, went to my sister's. I said, instead of renting a car, let's just, you know, use Uber or Lyft, and let's compare it and see what we do. You know, how's that? Very roughly speaking, it saved over the three days, it saved like over $300. And we never had a problem getting a car. You know, the question was, well, so on Thanksgiving, you're gonna have a problem getting a car. We didn't. It's so interesting when new industries come about that can put together a technology like that. Of course, there's been a number of those ride sharing businesses that have gone out of business. But yeah, I think that typesetters, you know, you can sit at the desk and do the typesetting now, you know, through your computer, but all those things have changed. But I don't know that they opened up doors for more fun, productive things to do. But if you're the kind of person who's looking for those kinds of things, you'll find them.
Dan Sullivan: There was an interesting article, this young woman, she's maybe late teenager, 20 years old, and she says, you know, what are really becoming scarce are collective experiences. And she gave a very good analysis. that every online company is zeroing in just on her and what she wants. They keep convincing her she's this type of person and only they can provide what that wants. And she said, you know, what we're missing is there's sometimes I don't want to be the only individual that they're dealing with, I'd like to have a sense of collective experience. And she mentioned about entertainment that probably one of the reasons why Taylor Swift was such a phenomenon is that she was giving people a real sense of collective. They were Swifties, and they would line up, and they would have tent cities waiting for the concert. And then sports, of course, is always getting bigger. And the whole point is that there's part of our brain which feels good being connected in some way to everybody else. And there is part of our brain that really values our uniqueness.
Jeffrey Madoff: That raises an interesting question because I wonder how much uniqueness is often more feared than embraced, or if not feared, marginalized. And so I wonder about that. I think feeling a part of something is something that ultimately all people want, but I think that there are enough people that are damaged along the way in life that the more they isolate, the more problems that arise.
Dan Sullivan: Oh yeah, I mean, there's clear proof of that.
Jeffrey Madoff: Right.
Dan Sullivan: I mean, and it's related to social media, actually. Great work by somebody right in New York City, Jonathan Haidt. Have you ever heard of him?
Jeffrey Madoff: Yeah, I've actually talked to him.
Dan Sullivan: Oh, good. He's got the latest research out on the incidence of mental problems where you've sought a practitioner, and related to the number of hours that you spend on social media.
Jeffrey Madoff: Yeah, I met him after his first book, we were at a dinner together. I think he was one of the first people to capitalize on the whole notion of happiness studies. It's really interesting. You know, and you've heard the expression that, you know, we're building the plane as we're flying it. That's kind of what our popular culture is. We don't really know.
Dan Sullivan: It was probably true 2000 years ago in Rome.
Jeffrey Madoff: Absolutely. It is what it is.
Dan Sullivan: Yeah.
Jeffrey Madoff: On a certain level, what's unique is that nothing is unique, you know, that there's precedence and antecedence to those things. But it's a reflection of the times, what surfaces to the top, that seems to be the most important.
Dan Sullivan: Well, yeah. Okay, I think we've checked off both boxes. We've talked about many anythings, and we've talked about everything. Yeah, we've talked about some things, but not too long to become unbalanced. I think that we're going after a very, very important subject in our book, Casting Not Hiring, to be available in public in autumn of 2026. And what I think about it is that the more that people are given the opportunity to fully engage with their brain, the more they enjoy the activity.
Jeffrey Madoff: Yeah, I think so too. And I would qualify that it's also not about winning. It's about participating and processing.
Dan Sullivan: It's about learning.
Jeffrey Madoff: That's right. That's right. And to me, learning is a process. So I agree with that. And I think it's also about thinking you're the main character in this performance life career. And, you know, I've often thought about the fact that life spans a lot longer than it used to be. And when it used to be about careers, you know, maybe, maybe you had a 30-year working life and that was a career. And the thought of leaving the security of that career path, which doesn't really exist much anymore. I mean, if you become a doctor or a lawyer or something, there is, but you know, there's always been a lot of dropout from those professions too. But you know, I never felt like, where's it written that you can have one career? I remember reading Margaret Mead, the anthropologist, and I don't remember how many marriages she had, but a number of them. And she said they were all good marriages, you know, but then she wanted something else, you know.
Dan Sullivan: From one person's point of view.
Jeffrey Madoff: That's right. That's right. But you know, there's nothing saying that you've got to spend from the time you get your first job until you check out that you have to stay on a particular path. So I think it's really interesting because I think we're defining a lot of the social conventions that were just givens that just aren't the case anymore. And I think that uncertainty causes people to seek for magical answers and magical thinking that aren't necessarily going to help.
Dan Sullivan: Yeah. But neither of us really care either.
Jeffrey Madoff: 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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