In short
Uncertainty and why it feels threatening; how “certainty” can reduce thinking quality; and practical tools for making decisions without needing guaranteed outcomes (e.g., small experiments, predictions, red-teaming beliefs, uncertainty exposure).
Key claims
Humans are biologically wired to seek certainty (life-or-death rustling-bush analogy), but modern decisions aren’t predictable; experts’ forecasts are often no better than dart-throwing chimps (Phil Tetlock’s synthesis). People prefer closure and sometimes choose guaranteed pain over ambiguity (50% shock study). Certainty can become a cognitive crutch that blocks adaptation; intellectual humility and “certainty anchors” (values/rituals) help you act despite doubt.
Guest backgrounds
Simone Stolzoff is the author of How Not to Know. She discusses research and interviews with psychologists and decision experts.
Notable examples
“Year of living dangerously” relationship experiment (a married couple separates for a year, then breaks up); OCD “doubting disease” framed as seeking relief from anxiety (MP3 player comparison); business pivot from Glitch to Slack (Stuart Butterfield shutting down a successful game); Airbnb’s pandemic values-based decisions (Brian Chesky); Jeff Bezos “one-way door vs two-way door” decisions; uncertainty exposure examples like trying new foods/routes or starting conversations.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOThe Experiment of Living Apart
4:00 to 5:02
Discussion about a couple's year-long experiment to understand their relationship.
“I really appreciate you driving all the way down here.”
Understanding Uncertainty Responses
5:02 to 8:08
Exploration of how people respond to uncertainty and decision-making.
“And here they are running a little experiment on their life.”
Values and Decision-Making
8:08 to 10:04
The importance of knowing one's values when facing uncertain decisions.
“One of my favorite quotes is from this guy named Rolo May, and he said, Commitment is healthiest not in the absence of doubt, but in spite of doubt.”
The Human Desire for Certainty
10:04 to 13:08
Why humans crave certainty and how it affects modern decision-making.
“So designed uncertainty versus accidental uncertainty is what I took from that experiment as well, I suppose, just because if they break up, it's okay.”
Technology's Impact on Uncertainty
13:08 to 14:00
How smartphones and technology influence our tolerance for uncertainty.
“where we could be eaten by a lion, it's like, do I need 250 gigabytes of storage or I need 512?”
Navigating Uncertainty in Life Decisions
14:00 to 19:59
Explore how the rise of technology has impacted our tolerance for uncertainty and decision-making.
“but it's going to be in his pocket the whole time.”
Finding Certainty Anchors
20:00 to 22:20
Learn how identifying certainty anchors can help you manage uncertainty in life.
“Amidst all of the uncertainty in your life, here is something that I can return to, that I can come back to.”
The Upside of Uncertainty
22:21 to 26:48
Discover how embracing uncertainty can lead to unexpected opportunities and growth.
“We often think about the fear or the threatening nature of the uncertain moments in our life, when in actuality, uncertainty can also be the birthplace of possibility.”
The Role of Confidence and Credibility
26:49 to 28:00
Understand how confidence impacts our perception of credibility and the importance of humility.
“The problem is it's easy until it's not.”
The Challenge of Predicting the Future
28:00 to 28:31
Explore the difficulties of accurately predicting future outcomes and expectations.
“It needs a little bit more humility as opposed to the hubris of people saying that they know exactly what the world is going to look like.”
Show all 34 chapters
Understanding Uncertainty and Decision-Making
31:19 to 37:14
Delve into how uncertainty affects our decision-making processes and the human tendency to overestimate consequences.
“I just did a show about it's coming out in the future.”
The Impact of Uncertainty on Health
37:15 to 42:00
Examine how uncertainty can affect our mental health and well-being.
“He didn't know whether hosts would be able to continue finding guests in another weeks or months or years.”
Understanding Ambiguity Aversion
42:00 to 43:10
Explore how uncertainty affects our stress and decision-making.
“or an 100 % chance of receiving this painful electric shock.”
The Fear of Uncertainty in Life Decisions
43:10 to 44:48
Learn how fear of uncertainty prevents beneficial changes in life and career.
“One thing it does is it keeps people from turning towards uncertain situations, even when those uncertain situations could be potentially beneficial.”
Building Tolerance for Uncertainty
44:48 to 46:03
Discover techniques to improve your tolerance for uncertainty in daily life.
“Are there benefits to those who are good at uncertainty?”
The Irony of Career Risks
46:03 to 47:14
Hear about the ironic stability of unconventional career choices.
“People were like, well, were you going to stop doing your podcast thing, right?”
Taking the Leap: Podcasting Journey
47:14 to 48:25
Jordan shares his journey of starting a podcast with no expectations.
“But it is quite ironic that turned out to be much safer than my regular paycheck.”
Embracing Opportunities with Low Stakes
48:25 to 50:28
Learn how low stakes can facilitate taking risks and building confidence.
“It wasn't like, eventually this is going to be monetized.”
The Value of Experience in Writing
50:28 to 51:47
Find out why taking action is essential to becoming a writer.
“They were like, I will do nothing to screw this up.”
Exploring Risks and Responsibilities
54:59 to 56:00
Understanding how age and responsibility impact risk-taking.
“You know, I will say there's a counterbalance to this whole like, oh, Jordan took all these risks.”
Exploring vs. Exploiting in Life
56:00 to 59:00
Learn about the balance between exploring new experiences and exploiting known preferences.
“very similar to the last song they listened to.”
The Comfort of Certainty and Its Pitfalls
59:00 to 1:01:54
Understand how discomfort with uncertainty can lead to the acceptance of disinformation.
“Here's something I thought was fascinating.”
The Traps of Comfort, Hubris, and Control
1:01:54 to 1:05:23
Explore the three traps of comfort, hubris, and control that hinder personal growth.
“Comfort is that voice that says, stay where you know it's safe.”
Navigating Uncertainty: Control and Acceptance
1:05:23 to 1:10:00
Discover strategies for managing uncertainty through control and acceptance.
“I think there is an objective measure about whether your life is too comfortable or not.”
Understanding Control and Uncertainty
1:10:00 to 1:11:57
Learn how to differentiate between what you can and cannot control in uncertain situations.
“these situations is we try and control all the outcomes.”
Personal Experience with Decision-Making
1:11:58 to 1:12:40
Discover a personal story about choosing between job offers and the lessons learned.
“I ended up taking the job at the design firm.”
Making Decisions and Seeking Advice
1:14:22 to 1:15:24
Explore the dynamics of decision-making and the role of external advice.
“Struggling with weight that doesn't respond to traditional dieting?”
The Role of Uncertainty in Life
1:15:25 to 1:17:14
Understand how exposing yourself to uncertainty can prepare you for future challenges.
“It's funny because when friends ask which job, or a big decision, I should say, I do have a couple of tricks, right?”
Experimenting with Uncertainty
1:17:15 to 1:20:56
Learn practical experiments to embrace uncertainty in your life.
“It's found that the five highest points of uncertainty in the world have all occurred in the last five years.”
Decision-Making Frameworks
1:20:57 to 1:24:00
Discover frameworks for making better, more expansive decisions.
“No, you're just writing and publishing on your own.”
The Secretary Hiring Problem: Making Decisions
1:24:00 to 1:26:59
Learn how to efficiently make decisions by understanding your preferences.
“And what happens is one secretary comes in the room and then you have to decide right then and there whether or not you want to hire them.”
Understanding Trade-Offs in Relationships and Jobs
1:27:00 to 1:29:38
Explore the importance of recognizing trade-offs in personal and professional decisions.
“If you're really looking, what could be better?”
Trusting Your Future Self Amid Uncertainty
1:29:39 to 1:32:20
Discover how to build confidence in your ability to handle future challenges.
“And I think that is an empowering mentality when it comes to these crossroads in our lives or these moments of uncertainty.”
Approaching Uncertainty with Curiosity
1:32:21 to 1:33:07
Learn the strategies to navigate uncertainty and embrace new possibilities.
“And for Emily, for example, she's so glad that Bill gave her that pep talk because her mom ended up recovering.”
Transcript
Automatic transcript. May contain errors.0:00This episode is sponsored in part by Dell. Dell PCs with Intel inside are built for the moments that matter. For the moments you plan, and the ones you don't. Built for the busy days that turn into all-night study sessions. The moment you're working from a cafe and realize that every outlet is taken. The times you're deep in your flow, and the absolute last thing you need is an auto-update throwing off your momentum. That's why Dell builds tech that adapts to the way you actually work. Built with long-lasting batteries so you're not scrambling for the closest outlet. and built-in intelligence that makes updates around your schedule not in the middle of it.
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1:29Lufthansa Allegris. All it takes is a yes. Coming up next on The Jordan Harbinger Show. The version of yourself that will handle that tragic situation, if or when it occurs, will be born into existence in that moment. And that version of you will have more context, more information, and be better equipped to handle that tragic event than the version of you today. You have to trust in your future self to be able to solve your future problems.
2:05Welcome to the show. I'm Jordan Harbinger. On the Jordan Harbinger Show, we decode the stories, secrets, and skills of the world's most fascinating people and turn their wisdom into practical advice that you can use to impact your own life and those around you. Our mission is to help you become a better informed, more critical thinker through long-form conversations with a variety of amazing folks, from spies to CEOs, athletes, authors, thinkers, performers, even the occasional mafia enforcer, Russian spy, cold case homicide investigator, or hostage negotiator. And if you're new to the show or you're looking for a way to tell your friends about it, I suggest our episode starter packs.
2:38These are collections of our favorite episodes, some of them anyway, on topics like persuasion and negotiation, psychology and geopolitics, disinformation, China, North Korea, crime and cults and more. That'll help new listeners get a taste of everything we do here on the show. Just visit jordanharbinger.com slash start or search for us in your Spotify app to get started. Today on the show, we're talking about one of the most uncomfortable forces in human life, uncertainty. Not, will my Uber driver find the airport entrance uncertainty? I mean, the big stuff. Should I marry this person? Quit this job?
3:09Move cities? Trust this expert? Admit I have no idea what I'm doing? Keep pretending confidence is the same thing as competence, because the guy saying it has a podcast mic and a frickin' fleece vest from Patagonia. My guest today is Simone Stoltzoff, author of How Not to Know, and we're digging into why certainty feels so good, why it often makes us dumber, and why the people who sound most sure of themselves are sometimes just emotionally over-leveraged carnival barkers with a LinkedIn following. We'll discuss why humans are addicted to closure, why not knowing can feel worse than knowing something bad is coming, and how our brains would apparently rather choose guaranteed pain than sit with ambiguity for five minutes like an actual grown-up.
3:45We'll also get into the traps of certainty and tools to get better at understanding uncertainty, like running small experiments, writing predictions, red-teaming our own beliefs, and more. So today, Simone Stoltsoff shows us how to stop treating uncertainty like a threat and start using it as a tool. Here we go with Simone Stoltzoff. Thanks for coming on the show. I really appreciate you driving all the way down here. Yeah, it's a pleasure to be here. You opened the book with a couple. They decide to take a year apart. It's an experiment. So instead of breaking up, were they not married? They were married.
4:16They'd been together for 17 years. So most people would say this is kind of insane. Yeah, totally. So I'll set the scene a little bit. They're out having a drink at a bar. They have been together for 17 years, married for 10. They're having a drink at a bar, and they're talking about their relationship. And both of them feel like something isn't quite right. And so they do something that others might see as insane. They say, we're going to run an experiment. For a year, we're going to go our separate ways. And then we're going to come back to this bar in a year and decide whether or not we want to break up or stay together.
4:48They called it the year of living dangerously. And I won't spoil the ending because you have to read the book. But it is a great example of what it means to actually turn toward your uncertainty. Because so many people would either just break up or grit their teeth and carry on. And here they are running a little experiment on their life. Nice. Don't give my wife any ideas. Okay, so was that actually brave or was it just a way of avoiding making a hard decision? And I'm going to spoil some things from your book. Sorry, not sorry. They don't make it in the end. And it's okay, but you also kind of knew that going into this.
5:21Otherwise, why would you take a year off? from your spouse. Come on, man. They knew already. Read the writing on the wall. Well, I think my informal survey of people I've talked to about it, it's about 50-50. Half of the people think, oh, this is like the Pina Colada song. This is a Hallmark movie. They're going to go their separate ways, then come back together and fall back in love. Another half is like, no, there's no way. If they spend a year giving their energy outside of the relationship, it's like a plane that's tilted a few degrees off. They didn't have kids, and the spoiler is out there.
5:51They ended up breaking out. And so I talked to lots of people that I talked to this guy named John Gottman, who runs this thing called the University of Washington. Their couples therapist was Esther Perel, the most famous couples therapist in the world. And the thing that really stuck with me was from the psychologist that I talked to. And he said, when people are faced with uncertainty, they have either one or two main responses if they're really uncomfortable with it. They either try to gather as much information as they can. They act super impulsively. So say you're looking to like, buy a new pair of jeans.
6:23If you're super intolerant of uncertainty, either you try on every single pair of jeans in the store or you just buy the pair of jeans in the window. And a more sort of adaptive approach is maybe try on like a few pairs and then pick your favorite. But that sort of impulsivity or need to gather lots of information are both responses to the same stimulus, which is uncertainty makes me uncomfortable. What should I do about it? It makes me anxious thinking about making an impulsive move if I don't have certainty. I'm far more likely to try on every pair of jeans in the store than I am to go, oh, just give me the first one.
6:55I do know people like that, but I can't relate at all. That's making me itch somehow psychologically. We all have a friend who is maybe in a relationship that they know isn't working for them, but they'd rather the comfort of the relationship they're in than having to face the uncertainty of what might be outside of it, or maybe in a job that they know isn't working for them. And so I think it does require some tolerance, some ability to say, okay, I know this is an uncertain situation. Even if I gather all the information in the world and survey all my friends, I might still not have certainty.
7:27How can I develop the conviction to make a choice regardless? Gosh, okay. So what do you think most people misunderstand about this experiment? I think the big misunderstanding is that treating uncertainty as a problem to be solved. When we're making any sort of decision at a crossroads like this, we might think that there will be certainty if we just bang our head against the wall at the right angle, or we just talk to the right person or have the right couples therapist. But often when we're at these crossroads, whether it's a career crossroads and a relationship, what have you, you often have to make a decision and commit in spite of the uncertainty or the doubt that you feel.
8:08One of my favorite quotes is from this guy named Rolo May, and he said, Commitment is healthiest not in the absence of doubt, but in spite of doubt. I think making decisions in spite of uncertainty, one, is an inevitable part of being alive, and two, it gives you an opportunity to build your character, to make decisions on behalf of the type of person that you want to be. What did that experiment, you think, reveal that a normal breakup wouldn't have revealed? Well, the big thing that I got talking to the couple was that it helped them figure out who they were. So one of the things that I think is really important when we're in these moments of uncertainty is to have a clear sense of who you are and what your values are so that you can make a choice.
8:50And even if it doesn't work out, you can still be proud of the choice that you made. So I'll give you an analogy from the business world. So in the past, you've had Brian Chesky on this show. In the pandemic, he lost 80 % of his business at Airbnb. And he had to make all of these decisions in spite of not knowing exactly how they'll turn out. And the first thing that he did is he wrote down a list of his values, these principles that he was going to stand by during the pandemic. One was to keep all stakeholders in mind. Two was to try to win the next travel season. Three was to not be the villain.
9:21And so by getting clear on his values, getting clear on what he stood for, he was able to make decisions like reimbursing all of the hosts that lost money during the pandemic. Wasn't that like a quarter billion dollars? He had to go to investors and go, here's the thing, we're trying to survive. I need a quarter of a billion dollars and we're going to spend it all on essentially nothing, like goodwill. Totally. The business is hemorrhaging money and he's trying to make a choice to spend more money to foster goodwill amongst his hosts. But the thing that getting clear on your values does is it allows you to stand by your decisions regardless of whether or not they work out.
9:55And so one question I like to ask myself in these moments of a crossroad is what is a decision that I can be proud of, even if I don't get the outcome that I want. Wow. Okay. So designed uncertainty versus accidental uncertainty is what I took from that experiment as well, I suppose, just because if they break up, it's okay. We're single again. Now I can find out who I am. And then if it's a bad decision, I regret it. And if it's a good decision, great. But you do the one year thing. I guess the tricky part is what happens when the guy comes back and he's like, I missed you so much. And she's like, actually, I have another boyfriend.
10:30Yeah, I forgot what movie it was. It was some like Jennifer Aniston movie or something. And they're like, okay, I'm three. We're going to say what we want from our relationship. One, two, three. And one person says, a divorce. And the other says to stay together. That's sort of the worst case scenario. But at least it allowed them to bring some intentionality into the decision as opposed to just doing something off the cuff. Why are humans so obsessed with certainty, even when we might not be that great at predicting things? I think it's biological. You think about our ancestors. If you are in the jungle and there's like a rustling in the bushes, you're reaching for a poisonous fruit that you're not sure, maybe it's poisonous, maybe it's not.
11:09That uncertainty could potentially be lethal. Unless you find out what's making that noise, fruit is edible, you can potentially be life or death, exactly. But that same wiring is now transposed on a lot of these decisions that we have to make in our modern life that aren't actually life or death. So we love certainty. We love people who claim to know exactly when the market is going to crash or exactly how the relationship is going to end or who's going to win the 49ers game on Sunday. But the truth is any prediction about the future is not certain by definition. It is some level of chance. And it's the same reason why we like music that's based on repeating patterns.
11:48When prediction is easy, when we can feel like we can anticipate what's to come, we feel safe and secure. But the truth is, humans are really bad at predicting the future. So there's this really famous study by this guy named Phil Tetlock, and he collated data from a decade worth of predictions from the smartest people in the world. So economists, politicians, journalists, etc. And his finding was that the average expert was roughly as accurate as a dart-throwing chimpanzee. How can that be the case? We are just really bad at predicting the future, whether it's something like what the interest rate is going to be next quarter or when the Iran war is going to end.
12:31We try to make these predictions, and we put a lot of credence in experts' opinions, but there's very little accountability. Think about sports, for example. All of these talking heads on the TV are telling you who's going to win the game, this and that. There's such little accountability to what actually works out. And so even though we are attracted like moths to the flame to these certain predictions about what the future is going to look like, the truth is nothing in the future can be certain. And so we have to become a little bit more comfortable with the uncertainty that we face. So we're not wired wrong.
13:05We're just outdated for the modern world. because instead of a rustling bush where we could be eaten by a lion, it's like, do I need 250 gigabytes of storage or I need 512? So I just take what I have now and I add a little bit more, but I know friends that are like, I'll get a text or something like, what do you think I need? And then it's, man, it's 100 bucks more. I know that's not nothing, but also just this is not something where you need to agonize or be spending three hours on chat GPT gaming out the amount of photos that you're going to be taking on. Like none of that is necessary, but you give a good example in the book.
13:39There's this guy who gets like two MP3 players. Yeah, this guy has really severe OCD. So the extreme example of someone who has a lot of doubt in their life. And this decision about which MP3 player to buy takes over his life. He starts like comparing them and then thinking he didn't listen to enough hip hop. And so he listens to a little more hip hop. And then he thinks about the aesthetics, but it's going to be in his pocket the whole time. Is it the aesthetics matter? And this sort of flip-flop being of looking for certainty is just an example of how much time and energy we tend to waste on decisions that are a little bit more reversible than we may think.
14:14I'm glad you brought up ChatGPT. I think part of the reason isn't just that the world is incredibly uncertain right now. It's also that our tolerance for uncertainty is in decline. So there's this great research study from this researcher named Nicholas Carlton, who found that the rise of the internet, and particularly mobile phones, is correlated with intolerance of uncertainty. I think phones do two things. One is they bring all of the world's uncertainties into our pockets. So now we can track the whereabouts of our kids. We can track crises that are existing on the other side of the planet.
14:46But that often just fuels our anxiety. And the second thing it does is it robs us of the practice of being able to sit with what we don't know. Now we feel like every big question of our life, whether it is which MP3 player to buy, or what job to take or who to marry is something that can be approached with the same framework that you might approach a Google query that has a definite answer. Whereas some of these decisions are never going to have definite certainty. You have to be able to have the trust in yourself to make decisions without knowing how they'll turn out. I suppose that's true. I mean, I have a buddy who, if we say like, hey, I wonder how many cows there are in California.
15:25He's like, no, no, no, don't Google it. We can try to figure this out. What is he? a mackenzie consultant no but and i'm like where would we even begin and he's like it doesn't matter if we get it right we can google it later but let's just talk about it and i'm like all right fine so we're talking about how many cows there are like how many farms there are how many oh quick we're passing one try to count the cows you know it's just impossible and then we google it and we're way off but something about going through the exercise of trying to figure it out it was almost nostalgic it was like you're in the car hey mom is a donkey and a mule the same thing And then your mom's like, Don, is a donkey and a meal the same thing?
16:00And he's like, I don't know. I thought it was the same thing. And you just never find out the answer. And then you're 46 and you go, I never did get to the bottom of that. And then you Google it. You're like, turns out they're different. I had no idea. 40 years later, I'm getting the answers to stuff where my parents either made up an answer to get me to shut up or just didn't know. There's a balance here. But you're right. I routinely I'll be in the car. And now we have Grok in the Tesla, right? So it's like there's a Grok button. and you just go, huh, is a mule different from a donkey? Let's ask Grok.
16:30And then you get, but they're infertile. Why is that? So I'm learning a lot, but you're right. The uncertainty lasts very little time. And the problem is if I have a big decision that I can't Google or Grok or ChatGPT, now what do I do? I mean, I think I'm not arguing for the value of not Googling. No, no, no. If you want to find a fact that is demonstrably true, look up the fact. But it's made me worse at dealing with things that I can't look up. Like now it's like, what do you mean there's no answer? And it can create expectation. Imagine the difference between walking into a movie that you've watched the trailer, read all the reviews, done all the research versus walking in with a little less context.
17:08There's more serendipity. There's more surprise. There's more mystery. Same with restaurants. I feel like we live with this epidemic where people are grasping for certainty everywhere they look. And uncertainty, although it can be threatening, it can be a source of fear, is also where the texture of life comes from. Man, that's such a great example. I used to work at a movie theater, and you couldn't just go see a movie whenever you wanted, but okay, all your friends are the people manning the little podium. You can go see a movie whenever you wanted. Plus, if you're working, I'm going to step into this movie and watch a little bit of it, because I got to clean a gummy bear that's stuck to someone's seat anyway.
17:43So you see every movie a lot, and then when you're off, you're like, you know what, this movie looks really dumb, but screw it, let's go see it. I've seen everything else that's in this theater. So I remember sneaking into like Austin Powers and being like, oh my God, that was really fun. Yeah. Because I remember watching the trailer on TV and going, I will never see this. Well, I work at the theater, so I'll see parts of it. But this is so stupid. And then your friends like make you go see it because it's the only thing you haven't seen 58 times. And it's hysterical. And you want to see the same thing with like Team America, World Police.
18:14I don't even know what this is about. And I showed up and I was like, what is this? And my friend goes, it's puppets. And I was like, I'll see you guys later. He's like, no, no, no, no, no, come with us. And then you watch it and you go, that was genius cinema. Then you're just singing America. Yeah, exactly. I even have that as a sound sample on the show. So is certainty actually useful anywhere? Or is it like a psychological crutch that we just deal with? Yeah, I think it's an important part of life to have certainty and uncertainty. So one of the biggest pieces of advice I give for people when they're in an uncertain situation is to find what I call your certainty anchors.
18:49What are the things in your life that you are certain about? When we are certain about some things, it makes it easier to hold uncertainty in other ways. So say you're looking for a new job. If you know where you want to live, if you know your commitment to investing in your relationship in a certain way, if you know the sort of type of role that you want to work in, it makes it easier to hold the uncertainty of exactly what job you're going to get. if you're feeling very uncertain about the state of the world. Maybe there are things in your life that can be rituals that are more regular, that make you feel more grounded in the midst of this uncertainty that you're feeling.
19:29I'll give one practical example. My grandmother passed away last week. She was 99 and a half. Oh, sorry to hear that. It's all right. She lived a very full life. But in the Jewish tradition, there is the seven-day period after someone passes away called Shiva. And what it is, it's the set of instructions. of exactly what you should do on each day after someone passes. And so you're dealing with this big uncertainty of losing your loved one, and yet you have the certainty of the set of instructions that can be incredibly grounding. And I think that's the power of something like ritual. Amidst all of the uncertainty in your life, here is something that I can return to, that I can come back to.
20:05It was nice of her to wait until you had your book tour to give you that example. Exactly, yeah. Grandma's always... Grandma, hold on until me. She's always thinking about you. What's a real world example of where certainty maybe makes somebody worse at their job? Okay, I think there's so many examples in the business world where people stay fixed to a very certain idea of how they think the future will look precludes them from being able to adapt. So there's all the canonical examples of BlackBerry or Kodak or Blockbuster where they had this 10-year map of how they thought the world would look and they were unwilling to update their vision of what the world looks based on new information.
20:47In the early 2010s, there was this startup in the Bay called Tiny Spec. And it was a gaming company. And they built this online multiplayer game called Glitch. And it was heralded as being like the next big thing. It raised$70 million before it launched. Its launch was covered in the New York Times. It had tens of thousands of active players in its first week. And yet the founder felt in his heart of hearts that the business wasn't on the right track, that it wasn't sustainable. And so he did something that others thought was crazy. At sort of the peak of the company's success, he decided to shut it down.
21:24And he made his investors whole. He gave employees that wanted to leave the option to leave. And then he took the employees that remained and pivoted the business around something that was completely in a different industry, which is while they were building the game, they had built this communications tool to be able to collaborate while they were trying to make the game a thing. and that communications tool ended up becoming Slack. And that founder, Stuart Butterfield, the company sold for$27.5 billion to Salesforce. It became one of the fastest growing enterprise software companies of all time.
21:59But in interviews, he said, we didn't know that this was going to be the next big thing. I didn't know in the moment that shutting down Glitch was the right move, but we discovered the opportunity. We discovered the possibility that lived on the other side of my uncertainty by being able to turn toward that uncertainty. And I think that is the upside of uncertainty. We often think about the fear or the threatening nature of the uncertain moments in our life, when in actuality, uncertainty can also be the birthplace of possibility. And if you're willing to turn toward that unknown, you might discover something that is greater than anything that you would have imagined before.
22:41That's quite a vision. Because I think if I'm winning on all fronts and featured in the New York Times, I'm not thinking, all right, time to yank the plug out of the wall on this thing and focus on our chat. Totally. But it ended up being a big bet. It's what statisticians call overcoming a local maxima. So you imagine like a mountain climber who's on the peak of a mountain. I've made it. But they don't know that there's a taller peak right around the corner. And so they have to be willing to descend from that shorter peak in order to discover something that's greater. Yeah. I guess having certainty reduces cognitive load, right?
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23:13If I'm very sure that this is something that's going to work out in a certain way, I just don't have to think about it anymore, which I hate bringing people's religions into this and stuff, but I think there's an element of that. if you have existential anxiety about something, everything else in your life is harder. But if someone's like, this is exactly what happens when you die. This is how you guarantee that you are going to get it. It's like, that's a load off. I guess I'll just go back to work now. I appreciate that about organized religion in some way or religion in general, I suppose. Our brains are really prediction machines.
23:45You kind of touched on that with the rustling in the bushes and we'd love to know what's going to happen next. Any American movie will kind of scratch that itch for you. I think that's the critique people usually have, right? It's like, oh, you can always predict what's going to happen next. But we like doing that. It makes us feel warm and fuzzy and sad. Yes. And I have little kids. You have a little kid as well. Maybe too little for this analogy to make total sense. But kids love to look at the same book over and over, watch the same movie over and over, watch the same video over and over. And for you and I, that's boring.
24:16I asked an expert, why do they do that? Because I watched the same stuff, I thought, because I only had one VHS tape of cartoons. So I didn't have a choice. You've got YouTube kids. There's a billion hours on there of different things. Why are they watching Miss Rachel again and again and again and again? And it's because it makes them feel smart. That was the shorthand version. I'm sure there's more to it, but it was like it makes them feel smart. It makes them feel like a sense of control when they're like, oh, this is the part where she makes the letter O four times in a row. And I'm going to do that again and follow along.
24:47I thought that was kind of an interesting idea because music, and you mentioned this in the book as well, follows a repeatable pattern. And you're counting or you're learning how to dance. You can go like, oh, now they're going to change the music. And it's like, I was right. You know, it's like, well, of course you were right. It's the same. And you've heard the song before. It's the equivalent of like comfort food. It makes you feel like you're in a familiar place where you're safe and secure. The problem is when you stay too fixed to that one idea of what the future should look like, and then it becomes brittle.
25:19The difference between what I might call blind faith and a more conscious version of faith. And so the sort of religion example to the extreme is something like a cult where someone says, if you follow this 10-step plan, if you do exactly what I say, then I guarantee you will be rich or you will go to heaven or X, Y, or Z. and if you are completely outsourcing your own autonomy or your own agency or your own ability to think for yourself, that's when you can find yourself out above your skis. You can find yourself in a situation where it is more problematic than it is self-serving. You mentioned that research showing experts are basically as accurate as it was a dart throwing chimpanzee.
26:00So why do we still trust confident people if they're wrong all the time? I think it's for the same reason, which is that the confidence or the conviction makes us feel like someone's in control. I remember when I was growing up, I used to work at a summer camp. And one of the lessons that I remember from our staff training was that kids' biggest fear is that no one's in control. No one knows what's going on. And I think in many ways, it's the same for an adult. And so it's very comforting when Jim Cramer says you should buy this stock or when this online self-help guru says the key is fiber. And if you maximize your fiber, all your other problems will go away because it gives you a sense of control over a world that is otherwise unpredictable.
26:45And it's really seductive and easy to follow those steps. The problem is it's easy until it's not. Yeah, sure. See also every cult ever. And I guess we just assume confidence projects credibility. What is our discomfort with uncertainty, what does that reveal? It reveals that we want to go back to what we were saying before, be able to predict the future and be able to plan exactly how the future goes. So we kind of have it backwards. We think that just having confidence and saying that you're certain about exactly what the future is going to look like will breed more credibility. But the research shows that you actually need a level of intellectual humility.
27:27The best leaders are not the know-it-alls. They're the people who understand what they know, they understand what they don't know, and are able to communicate both. So there was this great study about scientists whose previous experiments turned out not to replicate, not to be true. And the ones who were willing to own up to their mistakes, admit that they had made mistakes in the past, and update their worldview, were perceived as far more credible and confident than the ones who just said, no, I stick to my guns. I'm going to dig my heels in. And so I think that's what our society needs a little bit more of.
28:02It needs a little bit more humility as opposed to the hubris of people saying that they know exactly what the world is going to look like. I think the problem is it's really hard to write a book that goes, hey, all my previous books were kind of wrong. Thanks for buying them. And hopefully you're buying this one. My future books will hopefully not be as right. It's like, no, no, no, you can't do that now. Totally. Or that my last eight weeks of predictions of who's going to win the NFL game were wrong, but you should listen to me this week. This episode is about how planning can become anxiety in a little productivity costume.
28:32On that note, let's take a planned break for capitalism. We'll be right back. This episode is sponsored in part by Dell and AMD. The Cybersecurity Tapes just released a new episode and part one is available now. This one takes cybersecurity out of the abstract and into the real world, right in the middle of a business trying to stay online, protect its customers, and make critical decisions under pressure. These days, cybersecurity isn't something a business can afford to treat as a let's-do-it-later problem. The risks are constant, systems are interconnected, and the consequences move fast. By the time an issue surfaces, it's already affecting operations, customers, revenue, and trust.
29:07This episode tells the story of a chief information security officer navigating these exact challenges after his company is acquired. Suddenly, cybersecurity isn't just about answering technical questions. It's about explaining what cyber risk really means in business terms so it can be communicated to the board. Can operations continue? How quickly can they recover? What happens if customers are affected? and what does downtime actually cost? What makes this story so engaging is how it follows a CISO learning how to translate the language of risk into the language of business. Speaking to the board, not in alerts and vulnerabilities, but in impact and accountability.
29:38When that translation lands, everything changes. When it doesn't, the most critical decisions may be made by the people least equipped to make them. Part one is a compelling story-driven look at why cybersecurity isn't just about stopping attacks, it's about being prepared before you're in the middle of a crisis. Check out the cybersecurity tapes wherever you get your podcasts. This episode is also sponsored by Bowling Branch. I run hot when I sleep, which is annoying. It's also terrible for your sleep. Your body cools itself down at night by releasing heat through your skin. That heat has to go somewhere, from your body, through your sheets, and into the air.
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31:08Many of the guests on the show subscribe and contribute to the course. Come on and join us. You'll be in smart company where you belong. You can find the course, again, free with no shenanigans at sixminutenetworking.com. Now, back to Simone Stoltzoff. I just did a show about it's coming out in the future. It's a skeptical Sunday, which is where we debunk a topic, the whole like alpha male thing, or it's like, oh, alpha, this is a concept in nature and blah, blah, blah. Well, it turns out the guy who originated this was studying wolves in the 70s or something like that, or the 40s. And he basically came out 30 years later and was like, yeah, that was wrong.
31:46It only applies to wolves in captivity that are not related and kept in a really small space. So if you were studying humanity and you were just like, all right, we're going to look at a prison yard and just extrapolate from there how every society works on earth. And it's like, oh, that doesn't work. Totally. Or like so many of the mid 20th century experiments were just run on like white male college students. Yes. And of course, like all of your models for what an optimal seatbelt looks like or what have you is going to be outdated or wrong when you think about extrapolating that to the entirety of the diverse population.
32:21Human race. Yes, exactly. I think there's another element of this, which is we often overestimate the consequences of making the wrong choice. I mean, like the MP3 player guy, the worst thing that was going to happen to him was he would have maybe the second best or possibly still the first best MP3 player. But he spent like weeks missing work and evaluating and all this stuff. And yes, he had a mental illness that was like untreated. But I think we do this a lot. I remember thinking like, what if this business idea fails? And like the risk was so you'd be a few months behind and have to do something else.
32:54But in my mind, I was like, no, I'm going to be homeless and my family is going to leave me in the streets and I will never reproduce. I mean, I don't even know. Was it just catastrophizing to an absolutely ridiculous degree? And I would like to say I'm not usually that person, but I probably am usually that person. But I'm not alone. I think most people are like this or many people anyway. There's a few costs. One is just the time it takes to do all of this analysis. The second is catastrophizing over something that might not come to be. And I think a lot of us would benefit from recognizing the difference between decisions that are a little bit more reversible versus decisions that are a little bit more permanent.
33:34So Jeff Bezos has this framework around one-way door versus two-way door decisions, which I find helpful. One-way door decisions are decisions like, should I buy this house? Should I marry this person? They're a little bit harder to reverse. two-way door decisions are the things that we can course correct. We can be more adaptable if we were to make the wrong choice. The problem is too often we bring the analytical framework of a one-way door decision to a two-way door decision. And the cost is that we don't make the two-way door decisions as quickly as we should. And so we wait around trying to find the perfect X, Y, or Z to try and make sure that we know exactly how everything is going to go before we try.
34:15And in that time, we are wasting a lot of opportunity that may no longer be there. And so one thing I like to say is that the fastest way to learn is through building, is through doing, rather than trying to listen to a million podcasts about how to start a business or try and do a comprehensive market analysis before you record your first podcast episode. Actually, just go out and do it. And that will teach you much more than the endless hours of desk research. So when you say that experts aren't really correct most of the time, having confidence in a prediction, is that a scam signal? Not necessarily.
34:52You want to look at someone's bona fides, their research, their reason for having confidence in opinions. Of course, if someone has the accolades and the time spent really understanding the context of a problem, hopefully they're making better predictions than someone who is just shooting at the hip on social media. I was going to say, we look at the wrong signals. Most people are going, oh, I just count the number of followers they have on TikTok and decide if that makes them right or wrong. But a PhD isn't necessarily a water airtight plan to show that someone is going to be correct about what they're saying.
35:33The truth is that, especially with anything that is going to happen, anything that's going to happen in the future, we really don't know. One great example is there's a lot of talk right now about AI, what AI is going to do to jobs. And one of the smartest sort of godfathers of AI said that by the end of 2025, the number of radiologists is going to fall off a cliff. And yet in 2025, there were more radiologists than when he made that prediction five years ago. And so there is something to be said for wanting to know the direction of the world. But I think, especially in these moments of transition, we have a tendency to pull to extremes.
36:15So with AI, maybe you believe that AI is going to automate all rote work and usher us into this age of higher level creative problem solving. Or maybe you believe that AI is going to lead to this class warfare where the robots show up with the pink slips and it's going to lead to all of this destruction. And the truth is, it's probably not either extreme. It's probably going to look somewhere more in the middle. But by attaching our identity to one of these hot takes, it allows us to feel more secure because we think, oh, I'm in the boomer camp or I'm in the doomer camp. And it's like, OK, I've already made my bet.
36:53What's the best way to sound credible without faking certainty? It's to be clear about what you don't know. There you go. And that is what I think, particularly in academia, we could use more of what's called intellectual humility, being clear about the things that we don't know. And we'll go back to Chesky as an example. During the beginning of the pandemic, he didn't know exactly what the future of global travel was going to be. He didn't know whether hosts would be able to continue finding guests in another weeks or months or years. But he found certainty about the things that he could communicate about.
37:27So he increased his cadence of how often he was communicating with his team. And he said, OK, now everyone can know that every day I'm going to give them an update. And sometimes the update is going to be there is no update today. But that sort of regularity of cadence can be something that people can depend on. I don't know exactly what the future of this business is going to be, but I know that these are my values. These are the company values. These are how I want to act in spite of not knowing exactly what is to come. You mentioned before that having a PhD doesn't necessarily guarantee accuracy when predicting the future, but you also note in the book that experts can be less effective than novices in certain fields and certain tasks.
38:04I'd love examples of that because I think most people are like, wait, that doesn't sound right. That's counterintuitive, right? The benefit of expertise is being able to spot patterns. You have these quick heuristics that allow you to, say, if you're an ER doctor, identify what's wrong with the patient. But one research study found that those more experienced ER doctors, especially with gray area cases, can also jump to conclusions quicker and not stay open to some of those educations that might exist. There was another study about biologists collecting field data, and they found that some of the experts collected less accurate field data than the novices because they were just looking for things within their realm of expertise.
38:48The analogy of when you have a hammer, everything looks like a nail comes to mind. Expertise can give you overconfidence in your own abilities and make you see the entire world through the narrow lens of what you know, as opposed to staying open-minded to what is actually presenting itself. We talked before about the guy who had OCD with the MP3 players. OCD almost seems, look, this is not a medical definition, but it's like an uncertainty disorder. You're super intolerant of uncertainty. Yeah, they call it the doubting disease. Oh, do they? I've never heard this. Yeah. I find that really interesting.
39:22I'd never heard it framed that way because that's really what a lot of these people are seeking, right? Who hasn't gone down a rabbit hole? Which phone is better or which computer is better or which MP3 player? And I literally did. Should I get a Sony minidisc player or should I get this MP3 player? And I went down this crazy internet rabbit hole in like 1998 or something about the Diamond Rio versus the Sony minidisc or something like that. and I spent too much time dealing with that. But this happens, I guess, with folks with OCD, it happens about maybe almost everything. Yeah, I mean, there's different types of OCD and it shows up in different ways.
39:59For one person, it might be certainty they're seeking about whether the door is locked or whether the stove is off. And two things actually changed my mind about how I thought about OCD through the research. One is it's much more of a spectrum, but it's not this sort of like binary thing. There's people that have varying degrees of it. And the second is, it's not certainty per se that people with OCD are seeking. It is the lack of anxiety that they get from that brief moment after they check the lock to make sure the door is locked, where they feel safe and secure. So an analogy is someone that is addicted to heroin.
40:36It's not necessarily the heroin itself that they're seeking. It is the high that comes from the heroin. And for people with OCD, often the certainty is like the heroin. And what they're seeking is that brief moment of relief, a brief moment of, oh, okay, the door is locked. That comes from having that sense of certainty. But that certainty-seeking behavior becomes like an addiction. And before you know it, you're locking yourself in your apartment for days trying to figure out the perfect MP3 player to buy. This guy went from having a very successful career to being out in the world to agonizing for hours about whether he should take the 137 or the 205 train back home to see his family for Thanksgiving.
41:21giving. It's that assumption that if we just think hard enough, that if we just gather more information, we'll know for sure the perfect way to live our lives, when in actuality, there's a level of uncertainty and chance that's inherent in any decision about the future. So OCD folks need less uncertainty to feel more anxiety, but all of us have those two bars somewhere in our psyche. Interesting. Yeah. I hadn't really ever thought about that. So why does that feel worse somehow than knowing something bad is coming. Yeah. So there's this famous study where researchers had participants either have a 50 % chance of receiving a painful electric shock or an 100 % chance of receiving this painful electric shock.
42:07What they found was the people who had a 50 % chance felt far more stressed than people who have 100 % chance. So we would somehow how rather no a bad thing is going to happen to us than have to deal with the ambiguity of not knowing. I think part of it is once we know, then we can begin to plan. We can begin to think about how we might brace ourselves for the worst. We might be able to respond. Whereas the not knowing doesn't give us a toehold. It doesn't give us anything to feel grounded in the moment. There's another study that found that professional uncertainty, So not knowing whether or not you're going to lose your job takes a similar toll on our health to actually losing our job.
42:51And it comes back to that ambiguity aversion. We don't like to not know what the future holds. The problem is we often don't have a choice. That's definitely the problem. It's crazy to me that we'd rather choose guaranteed pain over uncertainty. That is also counterintuitive. Where does this show up in everyday life, career, relationships, things like that? Yeah. One thing it does is it keeps people from turning towards uncertain situations, even when those uncertain situations could be potentially beneficial. So it keeps us from leaving a mediocre job to find a better job, a mediocre relationship to find a better relationship.
43:28relationship. It keeps us from taking a big bet to, say, pursue a new business opportunity when we can just stay in our safe, secure place. The problem is that the safe choice isn't always the optimal choice. And because of our intolerance for uncertainty, we don't open our minds to other possibilities that could exist. How do you train yourself to not default to that instinct, or is that not possible? Part of it is just through exposure. So similar if you had a phobia of spiders. You might research some facts about spiders, and then you might be in the same room as spiders, but 20 feet away. And then eventually you might allow a spider to get close to you.
44:06The same issue with uncertainty. One of the best things that we can do to build our uncertainty tolerance is to, one, remember times where we've been in uncertain situations before and we've overcome them. And two, expose ourselves to uncertainty in smaller controlled environments. So little micro doses of uncertainty. It might seem innocuous, but something like trying a dish from a restaurant that you've never tried before, or striking up a conversation with a stranger, or taking a new route to work. These are little exposures to uncertainty that rewires our brain to make it easier to hold uncertainty in other ways.
44:40The problem is in our current world, we are so conformed, we are so comfortable in these little bubbles that we've created for ourselves that we aren't used to exposing ourselves to the discomfort that actually leads to growth. Are there benefits to those who are good at uncertainty? I mean, it seems like there naturally would be. Yeah. The main one is that they can discover things that are on the other side of what they don't know. So if you think about any sort of breakthrough entrepreneur or scientist that really has this big discovery, an artist that produces a piece of art that is really original and groundbreaking, it all comes from someone who's willing to go to a place where they don't know what is to come continue to persist.
45:24The musician Brian Eno has this great line where he says, I want to make music unlike any music that I've ever heard. And that comfort with uncertainty to be able to say, I don't know exactly how this piece is going to turn out, or I'm going to make this big bet and we don't know exactly how it's going to be received by the market, or I'm going to try and do this experimental technique that hasn't been done before. And that's what actually leads to those step changes in society and those big breakthroughs. And it exists in our personal lives, too. On a personal scale, you have to be willing to expose yourself to a new situation if you want to be able to learn and grow.
45:59Yeah. I'm not trying to pat myself on the back here, but it kind of reminds me of when I went to law school and I became a lawyer. People were like, well, were you going to stop doing your podcast thing, right? And I was like, no, I like it. And I kind of wish it was my job. And so I'm just going to keep doing it. And then ironically, in 2008, when everybody got laid off because the market tanked, it was this crazy, stupid waste of time podcast that everybody thought, you know, what a turd. I just started doing that because I kind of had a backup plan that I was able to monetize. Obviously, not as much as a Wall Street position as a lawyer, but those guys were on they were collecting unemployment.
46:36Right. I think a lot of people have come to similar realizations that the safe, secure, certain paths that they thought existed in the past may not actually be as secure as you thought. And something like building your own business or building your own platform can be more stable and secure than even getting a job in, say, big tech or on Wall Street. And people who cared about me, not just other students, but people in career services were like, you cannot have a side hustle business if you are going to work at a law firm. And I basically told this, I remember like the law firm, people were like, you could better hope they never find out and you better do it.
47:12And I went to this law firm and I was like, just so you know, I have a radio show that I do and it's on the internet. And they were like, we don't care. That's fine. And I was like, oh, good. but the HR people were like you're gonna stop doing that and I was like no I'm already hired and I don't have to listen to you anymore and it was fine thankfully but other firms I remember career services being like they are not going to be okay with this and I'm sure that they were right most firms probably would have been like no you cannot have a monetized hobby that looks like another job that's not going to fly and I was just pretty transparent about it and told them it didn't take a lot of time which it didn't at the time you know doing it once a week whatever and that That was it.
47:52But it is quite ironic that turned out to be much safer than my regular paycheck. Well, I'm curious, what do you think about young Jordan allowed you to take that risk of starting putting your podcast on the internet or starting to publish things to iTunes when there weren't necessarily models of that all around? There was nobody making money. Zero people were making money in podcasting at that point. I think this is 2006. I wanted to do stuff on radio, wasn't going to get hired on the radio, had no idea how to get hired on the radio, started a podcast, thought it was fun, never really intended it.
48:26It wasn't like, eventually this is going to be monetized. It was kind of like, whatever. Then I started selling some sort of phone coaching because guys kept asking me questions. So I started charging them a hundred bucks an hour, 50 bucks an hour. I can't remember to answer them. And then people were like, I'll give you $5 ,000 as a retainer and call you whenever I want or whatever. I was like, great. And then I started selling other stuff on the show. And then eventually I did get picked up by Sirius XM satellite radio. But initially it was, what's the risk of doing a hobby of a thing that I like?
48:55There's no risk. And then, like I said, career services was like, here's the risk that you're not seeing. Totally. But you were able to build your uncertainty tolerance by taking each of those steps sequentially. Like by saying, I'm going to charge$100 for this. You're like, oh, I can just make it up and go as I... And then that gave you more confidence to charge$5 ,000. It gave you more confidence to see yourself as a podcaster and pitch yourself to Sirius. I do remember some specific examples. So there was one guy who paid the initial guy who goes, you need to raise your price and I'm going to give you a$5 ,000 retainer.
49:27That guy was great. His name was Alex Schechter. So if you're still listening, send me an email because your old email doesn't work. But I thought that was super fascinating. And I was like, huh, okay. And then I remember talking with him and going, here's the problem. He was like, can you come speak to my mortgage bankers or whatever. He owned like a bank. And I go, oh, the problem is I'm not an expert. And he goes, yeah, I've hired all those experts. They suck. The reason I'm giving you a $5 ,000 retainer is because I use your free stuff and it's way better than what these experts. And then I remember going, but I can't speak because I'm not a speaker.
50:01And he goes, you know who else is a speaker? Pretty much everybody that comes in here to speak. I don't want somebody who's going to perform. I'll hire a band if I want that. I just want you to come in and teach. And I was like, okay, I can do that. So it was a little bit of nudging from people or being pushed and pulled by people who cared enough to do so. But there was also the, hey, why don't I try this because the stakes are low? And that was a huge advantage because I think my friends who were lawyers wanted to be a lawyer their whole life, who couldn't imagine doing anything else, who got a top market job with me on Wall Street.
50:33They were like, I will do nothing to screw this up. Meanwhile, Well, I went to law school because I had nothing else to do. My other idea was to get a job at Best Buy selling frickin CDs. And it was kind of like, oh, my God, if I get fired from my law firm, then whatever. I never cared about this anyways at all. And it was kind of like, well, I already graduated from law school. They can't take my law degree away. So, like, who cares? There's so many parts of that story. One, like Alex was able to raise your ambition. He was able to show you the peak that existed around the corner that you weren't seeing.
51:07Two, you were able to lower the stakes. And so taking this uncertain bet didn't feel as risky as if you had built it up in your mind and it was all life or death. And that's what allowed you to build more uncertainty tolerance by actually getting proximate to these new experiences as opposed to just thought experiments in your mind. Like an example, a lot of people send me DMs asking, I want to be a writer. I want to write a book. I want to be a journalist. and I often ask them like, okay, so like, what have you written recently? What do you like writing? And they'll say, I haven't actually written anything, but I have all of these ideas of things that I want to write.
51:41And what I tell them is the best way to learn about whether you want to be a writer is to write. And you don't need someone else to give you permission to do so. The fastest way to turn that uncertainty into a little bit more clarity is through actually doing the thing that you hope to do. Today, we're talking about how comfort makes us dumber over time. So before your brain turns into a couch cushion with a LinkedIn profile, let's hear from the sponsors who make this show possible. We'll be right back. This episode is brought to you in part by Lufthansa. When people talk about travel, they usually focus on the destination, the hotel, the restaurants, all the stuff that happens after you land.
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54:52Someone here will surface that code for you and get to the bottom of it. It really is that important that you support those who support the show. Now, back to Simone Stolzoff. You know, I will say there's a counterbalance to this whole like, oh, Jordan took all these risks. Now that I'm older, I can't relate to 26 year old Jordan. Like I can't at all. And I don't know if I'm becoming worse at uncertainty with age or if it's just because I have more responsibility. Like I try to put myself in a place where, okay, how would I feel if I didn't have two little kids? I wasn't married to somebody who was dependent on my business.
55:28Would I also still be like, screw it. If this crazy cockamamie idea I have fails, I'll just move to Thailand where it's really cheap and I'll be fine for five years, which is enough runway to get me. Would I do that or would I still be like, I am not doing that? That's insane. I can't tell because I can't sort of isolate those variables. Yeah. I mean, there's this dichotomy that I talk about in the book called the explore exploit trade-off. Imagine you are an engineer and your job is you work for Spotify. You have to pick the next song that plays in someone's playlist. For someone, you might play a song that's very similar to the last song they listened to.
56:03This is what would be called exploiting in computer science. Or for someone else, you might pick a song that's very different from the last song they listened to. That would be called exploring. And there's benefits to both. Exploiting allows you to take that safe bet, to play something that is similar to what they listened to before. It's likely not to piss them off. But too much exploiting will lead to something getting stale. It's like someone who listens to a song on repeat into oblivion and then starts to hate it. Whereas exploring is riskier. You are trying to find sort of the bounds of the character map, but the potential upside is that you might discover something that the user likes that they didn't previously know about and expand your understanding of their taste.
56:49In life, we need both. So when you're younger, you have maybe a lot more capacity to explore. You can go backpack around Macedonia, try out these different careers, or take classes that are outside of your major. And as we get older, we get more refined, we get more calcified in our ways, and we can do more exploiting. But that being said, we all need both. And this is true in biological systems. So there's this great study about ants who are foraging food, and they need to do some exploiting if they find a food source. but they also need to do some exploring and peel off so that they're not overly dependent on that one food source.
57:29And I think it's a great analogy for life. Even though as you get older, you have more responsibilities, you might be doing more exploiting. You might know the order that you like from the restaurant or exactly how you want your days to go. If you get too fixed, if you're too attached to one particular vision of your life, it's like balancing on a really narrow platform and you're susceptible to being blown over. That does make some sense. Remember, Pandora, Pandora might still exist, but that used to do that with it. It used to have like a really good balance where you could listen. You go, oh, I really like Paul Olkenfold.
58:02And it was like, okay, but here's a bunch of other electronic artists you probably never even heard of, but they don't immediately go to, here's some weird experimental crap from Canada, from these three guys who use synthesizers in a garage. It's like, it's like too far in the exploring direction. But eventually you do get there and you're like, I kind of like that too. right but before that it's here's sasha he's also from the uk here's carl cox what do you think you're like okay maybe this is not this one and so it leads you in these different directions or it used to do that right remember it used to scroll from side to side and be like here's what you're listening to now and then yeah and eventually you get to i don't know like boards of canada where it's like what the heck is this and the best part of pandora was every so often you'd stumble upon an artist that you'd never heard of before that you fell in love with yeah and then your friends make fun of you endlessly for listening to some weird obscure canadian electronic experimental music.
58:50But yeah, you would never find that otherwise because it's not getting played on the radio. So you have to start with the Paul Oakenfold top 40 or whatever, I guess Avicii or something, whatever at the time. All right. Here's something I thought was fascinating. People who are less comfortable with uncertainty are more likely to accept disinformation as true. What's going on there? It comes back to our desire for certainty and for an easy explanation how the world works. And so I'll give one example from Wall Street. So there's a study by this researcher named Katie Milkman, and she was looking at stock pickers who were wrong in the previous quarter.
59:31And it roughly broke down into two groups. There were people who were wrong that were part of the consensus. So lots of people were also wrong with them. And then there were people who were wrong, who went out on a limb. And what she found was that in the next quarter, the people who went out on a limb were more likely to double down on their erroneous prediction than people that were part of the consensus. So imagine you're like a flat earther. A lot of your identity is probably tied to this opinion because it's countercultural. It's swimming upstream. And so So updating your belief isn't just changing your mind, it is potentially undermining your own self-image.
1:00:14And so for these stockbrokers who made picks that were out there on the limb, they didn't want to update their worldview because it would mean admitting that they were wrong. The same thing is happening for people who easily cling towards disinformation or conspiracy theories. They want to find a certain view of the world that makes everything make sense. I think at the beginning of COVID, we saw a ton of this. If I only find the right type of bleach, then I can make all of this go away. And that need for certainty gets them to both cling on to a silver bullet and be less willing to update their perspective because they're tying their identity to this silver bullet they're choosing.
1:01:00The term in psychology is escalating commitment to a negative course of action. You might be going down a path and then rather than updating your belief when presented with new information, you end up doubling down. Like with multi-level marketing. Hey, I didn't make any money. Okay, but I'm going to convince myself I did. Okay, but when I do the math, I'm still losing money. All right, great. I'm going to upgrade to diamond level by paying an extra$10 ,000. Totally. Like the canonical example is doomsday cults. I think the world is going to end on a very particular day. And then that day comes and then the majority of people hopefully leave the cult.
1:01:36But then some people double down and they're like, because of our prayer, we prevented the doomsday from coming. And then they're further deep in the rabbit hole. Some kind of mental gymnastics gets them back to the circle. So in the book, I talk about these three different certainty traps. The first is comfort. The second is hubris. And the third is control. Comfort is that voice that says, stay where you know it's safe. You don't have to go outside of your comfort zone. Hubris is that voice that says, you know what's best. And control is that voice that says, you can plan everything. You can be the architect of your future.
1:02:07And on the flip side is a virtue that I think you might be able to access if you're able to become more comfortable with uncertainty. So on the other side of comfort is growth. If you're outside of your comfort zone, then you can learn things about yourself and the world that you wouldn't otherwise. On the other side of hubris is humility. If you're able to become more comfortable saying, I don't know, you can see the world as it is, as opposed to as you wish it to be. And the third is control. And on the flip side of control is acceptance, accepting that you're not able to control every single outcome.
1:02:42And so each of the case studies in the book falls into one of these three categories. But when I think about people who are really intolerant of uncertainty, often you can see one of these traps. Either they're trying to control what they can't control, either they're overconfident in their own abilities, or they're too comfortable without being able to expose themselves outside. Interesting. Yeah, I just remembered something about the same girl. Again, she was very smart and talented, so I'm not trying to smack talk her, but she had a lot of these weird habits. So I used to underline things in my book with pencil or write notes.
1:03:13And we were done. We took the exam. She goes, what are you going to do with your book? And I was like, I'll donate it or sell it. And she goes, Can I have it real quick? And I was like, sure, because we're doing something. And she got a big eraser and she went through every page. And I said, why are you doing that? And she was like, well, you said you were going to sell it. I was like, yeah, but that's the other person's problem. It's a used book. And she goes, I can't let you drop this book off with underlines and circles and notes of your own and pencil in here. I have to get rid of this. And I was just like, oh, my God.
1:03:41I mean, talk about the need for control. It just made me think, what things are you doing that you don't let other people see? I'm excited to look at her stock drawer. Oh my gosh. So does comfort make us not dumber over time, but I assume that our pathological need to be comfort is not good for us. Ultimately, it makes us less adaptable and resilient. You think about someone in the past who was able to figure out how to brave the elements or figure out what to do if they didn't get the right dinner that they wanted to. Now our problems, especially in the first world are so much more minute. And what it does is it decreases our ability to be more resilient if things aren't able to go our way.
1:04:27So one of the people that I profile in the comfort section is a guy who creates a computer algorithm to make every life decision on his behalf. Where do I eat? Exactly. Where should I live? What should I wear? And on In one sense, you might think of it as a type of uncertainty exposure therapy where he's just leaving everything up to chance. But I talked to the psychologist about it and he said, actually, I think it's another type of avoidance. Outsourcing all of his decisions to his computer algorithm, he's staying where it's comfortable, which is not having to make choices himself and take responsibility for his own choices.
1:05:02And so I think the need for comfort is innate, but we also need to be able to teach ourselves that if we are in a situation that's unlike a situation we've been in before, we can develop the skills to be able to make it through. What's an early warning sign that maybe comfort has turned into stagnation? I think there is an objective measure about whether your life is too comfortable or not. The one that I would use for myself is, what is the last thing that I've learned? Or what is the last novel experience that I have? You can find yourself in the series of rinse and repeat days And that might be an indication that you need a little bit more disruption in your life.
1:05:45So Aristotle has this idea about a golden mean. And what he says is all virtues lie as a mean between two extremes. Maybe on one extreme, there is complacency where you are just in a stagnant place. On the other end is this, I don't know, feeling of being unmoored or like you don't know what you can rely on. You don't necessarily need to know where you are on that spectrum, but if you feel like you're a little bit too far in the complacency spectrum, maybe you need to push yourself towards some novelty. If you're a little bit too far on the sort of chicken with a head cut off end of the spectrum, maybe you need to find a little bit more comfort to help rectify your situation.
1:06:25I guess I just wonder how smart people end up in these belief systems that clearly don't make sense from the outside, but it's a slow drip. Yeah. Yeah. So that's comfort. I would love to talk about hubris because you mentioned experts. They seem worse somehow at handling uncertainty. I don't know. Is that my imagination? Well, what expertise does is it gives you confidence. The problem is when it becomes overconfidence. And you see this in a lot of different fields. One is sometimes someone has expertise in one field, which makes them think that they can pontificate about the best things to do in all these other fields.
1:06:57Oh, yeah. What is it called? Intellectual trespassing? Yeah, exactly. Oh, I'm really good at building machines. Therefore, I'm going to talk about a new virus and with authority that just absolutely is hallucinated. Totally. Another thing is when you have a really narrow area of expertise, you start to see the whole world through that area of expertise. The analogy you're like is you're like a drunk man who's looking for his lost keys under a streetlight because that's the only place where it's lit up. You don't see the bounds of your own understanding of the world. I write a lot about what's called the replication crisis in social sciences, which is in these industries like social psychology, there have been all of these canonical studies.
1:07:37You may have heard of, say, like the marshmallow study. Oh, yeah, the marshmallow test. So we tried that with our kids. And then, yeah, I've heard that maybe it's just bullshit. Yeah, I mean, it just hasn't been able to be replicated. And so your ability to withstand eating a marshmallow doesn't actually predict your future life outcomes and not actually the things that correlate are income and how much safety and security you had growing up. But it is this big existential threat for someone who might have dedicated their life to studying a particular psychological phenomenon. Not to mention all these perverse incentives around the need to publish papers in their field and the need to get recognition from their peers.
1:08:14And so how do we get past a moment where trying to be interesting is more important than trying to be right or tell the truth? We need to have a little bit more intellectual humility as opposed to hubris. Yeah. How do you stay sharp, though, when you become the expert? How do you go, okay, I'm an expert in this field, but I want to leave the door open for a draft and keep things flowing? Well, I'm sure it's something that you've seen interviewing so many experts on this show. A lot of the smartest people I know are the ones who are most willing to admit what they don't know. And they're able to say, oh, I am not sure.
1:08:50I've never thought about it this way. Oh, I need to update my thinking. Oh, I need to learn more about that. And that, I think, is actually a much better sign of someone who has expertise than someone who fronts like they know about everything. But a lot of people, a lot of smart people double down instead of updating. Yeah. So what's going on there? It goes back to that sort of escalating commitment thing, where rather than have to reckon with the fact that you might have been wrong in the past, we have this cognitive need to maintain a positive self-image. And so we think that admitting that we were wrong would somehow undermine our positive self-image of ourselves.
1:09:25And so we'd rather double down than update our beliefs. Even though updating our beliefs is what builds trust from the outside perspective. And it's what allows you to see the world in a more accurate way. Yeah. Okay. And control, we try to plan everything even when it doesn't work. I guess that's just also human nature. I think particularly in people's careers right now, we see a lot of this, where people are so uncertain and worried about how AI might impact their industry, how the future of their ability to provide for their family, whether they might get laid off or not. And part of what we do in these situations is we try and control all the outcomes.
1:10:03The problem is you don't always have power to control the things that we try to control. And so you might've heard of the serenity prayer. God grant me the serenity to know the things I can control, know the things I can't, and the wisdom to know the difference. That's the piece of advice I always give for people who are anxious or worrying about something that hasn't come to pass yet is step one, separate what you can and can't control. Step two, think about how you might be able to plan for different possible outcomes as opposed to being fixed on one particular vision of how the future might go.
1:10:37And then step three, accept that you might not be able to control all outcomes and try to regulate your nervous system, do what you can to be able to be okay with not knowing. Where does planning become a control addiction? When there's diminishing returns to the information that you're gathering. So in the beginning of information gathering, you may learn some new perspectives. You may be able to think about a problem in a different way. But at a certain point, you can see that productivity start to level off. So one example from my life, I was once deciding between taking a job at this prestigious magazine or at this design firm.
1:11:13And I couldn't make up my mind for the life of me. I had these sort of two job offers in front of me. And on one path, there was Simone, the journalist. On the other path, there was Simone, the designer. And I was insufferable. For like weeks, I flip-flopped. I talked to my Uber driver about it. I talked to my yoga teacher, every friend in my life, all my family members. And the thing is, I was looking for certainty about a decision where there was no certainty to be found. I thought that if I just banged my head against the wall at the right angle, then I I could control exactly what my future would look like.
1:11:46And the truth is, with a decision like that at a crossroads, there's some level of trust of having to make a decision in spite of not knowing that you need to be able to do if you want to be a human in this world. And so which job did you take? I ended up taking the job at the design firm. And my biggest fear was that it was going to be the worst thing that ever happened to my writing career because I had a job at a magazine. It's hard to get paid as a writer full time. and because I had that job at the design firm, I ended up having the capacity in my days to be able to write in the mornings and the evenings.
1:12:19And I wrote my first book and 10 years later, I'm a full-time author. Amazing. Okay, so that turned out fine. Good thing you wasted all that time thinking about it. No, I mean, come on. Surely that had a great effect on your decision-making, but you're right. Once you're talking to your Uber driver, who's like, I'm just taking you to the airport. I don't give a fuck what job you take. Right, yeah. We'll be right back after this short break. use it to hydrate, stretch, or pretend you're in control of your life because you organized your tabs by color while ignoring every meaningful decision you've been avoiding since March.
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1:14:58Get 15 % off plus a$40 bonus gift when you subscribe at prolonlife.com slash begin. Don't forget about our newsletter, We Bit Wiser. It is something specific and practical that'll have an immediate impact on your decisions, psychology, relationships, in under two minutes every Wednesday, almost. And if you haven't signed up yet, I invite you to come check it out. It really is a great companion to the show. JordanHarbinger.com slash news is where you can find it. Now for the rest of my conversation with Simone Stolzoff. It's funny because when friends ask which job, or a big decision, I should say, I do have a couple of tricks, right?
1:15:35One is like, oh, who have you discussed this with? And if they're like, just you, I'm like, okay, let's really break down pros and cons. I'll help you through this. But if I have a friend who's like, oh, I've talked to everybody about this and it's been weeks of deliberation, then usually I go, okay, tell me the options. Then I go, definitely this one. And they're like, really? And I'm like, definitely. No question in my mind whatsoever. And it's just, because I know it's, I'm basically the coin they're flipping. Totally, then they can react to something. Yeah, yeah. And then if they push back a bunch, I go, huh, interesting.
1:16:04It's almost like you really want the other one instead. And then they're like, yeah, actually, you're right. No, that's interesting. You're right. Or if they're like, I knew it. I'm like, yeah, you're welcome. See you later. Because I know that I'm just a human coin. Totally. And they wanted to roll the dice. Whatever decision they're going to make is probably going to be half. Exactly. One of the things that makes hard decisions hard is that one option is probably not better than the other in all different categories. There's probably trade-offs. If one option were clearly superior, it wouldn't be a hard decision.
1:16:32It'd be an easy decision. And so one of the philosophers I talked to in the book says, when you're in that moment, what you should do is make a decision. And then after you've made the decision, convince yourself of all the reasons why you made the right decision. There you go. You can sort of retroactively form the narrative. Which you're going to do anyway, probably. Exactly. But first you have to be able to transact. You have to make the decision. Do we need to design more uncertainty into our lives? Is there a benefit to that? or is that already just happening so much? If your life is too fixed, if you're too far on the exploit side of the spectrum, I do believe you benefit from exposing yourself to more uncertain situations.
1:17:08But more than anything, what it does is it prepares you for the inevitable uncertainty that you're going to face. So there's one study of uncertainty over time and it's been going on since the 80s. It's found that the five highest points of uncertainty in the world have all occurred in the last five years. wait is that real based on the metrics that they use so they track the mentions of uncertainty in newspapers etc but you think about it i thought i thought okay people's perception of uncertainty because i'm like man surely some roman empire industrial revolution or the bubonic plan world war ii since the study began in the 80s okay okay okay covid war in iran tariff policy war in ukraine etc we're seeing all these global spikes of uncertainty in people's perception at a time when their tolerance for uncertainty is at an all-time low.
1:17:57And so what it does, exposing yourself to uncertainty, is it prepares you for future uncertain moments that you might be exposed to. Okay. I'm glad we clarified that because I was just thinking, surely. Yeah. If you lived in Florence during the bubonic plague, you're like, oh, I'm sorry about your little overseas geopolitical fight right now. Right. Sorry the Strait of Hormuz was closed, but my entire family was wiped out by a plague. Yeah. Okay. That makes way more sense. Yeah. I love kind of the idea that we can try uncertainty experiments. Do you have any ideas that people can run just short, time-bound maybe?
1:18:33Yeah. Low stakes? So, for example, one thing I've been doing for myself recently is I hate marketing. Like, I hate having to try and push a buck onto people. I like to be the sort of like the writer behind the scenes. Yeah, not going to work. Not okay. In today's day and age, we need to be able to promote ourselves. And so one experiment that I've done is I'm just going to post an Instagram reel every day for 30 days. And of just me talking and just an experiment. And what I'm going to learn is whether this is something I want to continue with, whether this is something that actually has an ROI for me or not.
1:19:09I think when people are experimenting with different career paths, they could use that experimental mentality. So often we think that these decisions are life or death. They're so black and white. When in actuality, you can prototype the decision that you want to make. Say you're considering a move. Go to the city that you want to move to and spend a week in an Airbnb and see what that feels like. Say you're considering making a career switch. Try to get proximate to the actual experience of doing that work. Go intern or shadow someone as opposed to thinking that it's just something that you have to design the right thought experiment.
1:19:43How can you prototype it? It's funny you mentioned interning because somebody had written me recently and they're like, I'm really thinking about making a career shift, but I'm 38. And I was like, go get an internship. You'll be a shoe in because you actually have qualifications and everyone else applying is like 19. And he was like, an intern? I'd never thought about that. Or just shadow someone that does that work for a day as opposed to just making it in your mind, try and make it in the real world. I don't know about you. There are so many jobs where I would love to intern or shadow somebody for a week.
1:20:16It would be absolutely nuts to be able to shadow or intern someplace. And I won't give any ideas because I don't want to feel bad. People send me emails like, I would invite you to do this at my company. And I'm like, oh, gosh, I can't. I wish I hadn't said that. But imagine even in some of the jobs are crazy, like people who could get rid of landmines. I want to go check that out. I don't really want to be next to the guy doing that, but I kind of want to check it out. And yeah, you could probably do this. Especially if, let's say, you're in a position where you're leaving your job, you could probably ask for a sabbatical or extended leave, and you really could go do an internship at the magazine that you're thinking about writing for, even though you're retired from your other career.
1:20:55Like, you could do that. Or in today's day and age, you often don't even need someone else to give you permission to do it. Just write the article. No, you're just writing and publishing on your own. Yeah, that's true. Yeah, nobody has to put you on anymore. Exactly. Are there decision frameworks for hard decisions that you recommend? Yeah. One basic heuristic question that I like asking is which decision would be more expansive versus which decision is more contracted. And I think what it does is it takes a decision out of your mind and brings it more into your body. Tell me what you mean by expansive versus contractive.
1:21:28So I'll give you a personal example. When I was in my early 20s, I was trying to figure out what I wanted from my romantic life. and I was going on lots of dates and I thought the best way to figure out what I want is to try and date as many different types of people as possible. And I was getting into relationships and I'd leave them after a month or two and try the next one. And I realized that actually, the greater source of novelty for me was through commitment, was getting through the honeymoon phase of relationship and staying in it and learning that way as opposed to just trying to date many different people.
1:22:04And so what was actually more expansive, what was actually more novel for me, was staying with a relationship as opposed to the sort of crutch that I had relied upon, which is just like, oh, I'll try this for a date or two and then move on to the next. This is interesting because I don't have the studies handy in my head here, but I believe I could be wrong, but I believe there's plenty of evidence about people who have way too many options with dating being far less happy than the people who have decision constraints when it comes to relationships. So for me, people are like, oh, you must have dated a lot of people.
1:22:37So I went through phases where I dated a ton of people, but usually more or less I was a serial monogamist and people are like, oh, wow, that's really good thinking. And it's like, oh, no, look, don't get the idea that I was a serial monogamist because I decided to push through hard times and like stick it out with one person because that was the best idea. I didn't have a choice. At least in my mind, it was like during that phase of my life, the reason I stuck with one girl for a long time was because that was the woman that tolerated my shit for the longest period of time. This wasn't like, oh, I'm going to choose her out of the hundreds and hundreds of girls that are beating down my dorm room door in college.
1:23:10No, that was the girl that answered my email or whatever, right? That was the girl that kept talking to me after an hour. There's freedom in that constraint as well. I think the paradox of choice too often are problems today are through abundance as opposed to scarcity. Yeah, it's funny to think about. Of course, I did go through phases where it was like, oh, I live in New York and the ratio is two to one and I can meet a new girl every week and have a huge rotation. But I found that that wasn't making me as happy as I was when I just had one girl that I actually liked. So I was pretty lucky to have that serial monogamy experience before going into a city where I had maybe unlimited options, that gets old super fast.
1:23:50Yeah. There's this great experiment called the secretary problem. And it's a thought experiment where you have to hire a secretary for your job and there's a hundred potential options. And what happens is one secretary comes in the room and then you have to decide right then and there whether or not you want to hire them. And the question is how many secretaries should you interview before you make your choice? And what the research found is basically you should interview 37 secretaries and then of those 37 and determine which is your favorite, and then keep interviewing until you meet someone that is as good or not better than the first 37 that you interviewed, and then hire them on the spot.
1:24:28And the sort of rationale is those first 37 will give you a sense of what you care about, what you're looking for, what you value. And then once you know that, you should be able to have enough conviction to make the choice that you want to make. And so that same could be said from a dating perspective or from a job perspective. In your 20s, you want to take some time to figure out what is your rubric, what matters to you. But once you know what matters to you, you should be able to commit and actually continuing to optimize for optionality is not good for you in the long term. It's interesting.
1:25:00We hired a nanny and Jen had gone and like care.com and talked to different people and was like, it's a nightmare out there. There's all these people complaining and it's expensive and they're underqualified. And you get a 19 year old who's like, I'm not going to do that. And I'm not going to do this. And I want a one week off per month because I got to fly to New York to see my boyfriend and I want a green card is all these crazy things. And so we're like, all right, we're going to start this interview process. And the first person we interview is like a 50 year old woman who has four kids, all successful.
1:25:30One's a lawyer, two are nurses, one's in college. And she speaks Spanish fluently and is a trained nurse. And we're like, okay, she's awesome. And my wife's like, I love her, but she's the first person we interview we we can't hire the first person we interview and i'm like don't even let her go to the thing she's going to after us because they're gonna hire her if they've interviewed 50 people and she walks in the door totally so we just hired her on the spot and how to work out like yeah she's been here for four years it's amazing because you knew what mattered it was just like look this person checks all the boxes and is actually better than we expected who could possibly walk in this door that would be better than this person right now and we just basically had no answer.
1:26:11And the only way that you're going to learn whether she's the right nanny is through the experience of her watching your kids. There's limited information that you can gather through an interview. And the quicker you're able to transact, the quicker you can make that decision. And ultimately, it's a two-way door decision. If it doesn't work out, you can probably go back to the drawing board. That's what we said. We're like, look, we're not signing a five-year contract. She's not requiring a down payment. This is just somebody who wants to work with us. Let's just do it and give her a try. Like worst case, if she walks out that door and she walks to another interview, which I think she had right after us, I'm like, it's over.
1:26:43They're going to hire her on the dang spot. So that was really fortunate. But yes, we had to know what we wanted a little bit beforehand and not try to optimize. Whenever now when I try to optimize, I go, this is pretty darn good. Should I look at a few more? What could be better? Often the answer is, I don't know, maybe something. And it's like, that's not good enough. If you're really looking, what could be better? Oh, well, the person I'm dating now doesn't have a job and doesn't want one. Okay, that could be better. There's something defective about this relationship. But if you're like, I don't know, maybe the next person will be slightly taller than the one.
1:27:19It's like, you got to draw the line somewhere. And you don't understand the other trade-offs. The most popular New York Times op-ed in the last 20 years had a kind of click baity title, but it said, why you'll marry the wrong person. It was by this guy named Alain de Botan. And the argument he was making is basically, when we think about potential suitors or potential mates, we just think about their upsides and the great things about them. But it would be more beneficial to ask also, in what ways are they crazy? And the same thing is true with jobs. We think about the benefits of all of these jobs, but every job has a trade-off.
1:27:52You can work on Wall Street, you make a lot of money, really long hours. It may not be meaningful. You can work at a homeless shelter, and it can be incredibly meaningful, but maybe it doesn't allow you to pay for the life that you want to live. All of these decisions are about trade-offs. And so coming back to the very first situation that we started this conversation about, this couple deciding whether or not they want to get divorced, talking to this love expert, John Gottman, he basically said, when you're in indecision about relationships, the most important thing is you have to know thyself.
1:28:22And if you know yourself, then you'll be able to handle all manner of slings and arrows that might come your way. I talked to another ethicist who was talking about making decisions when you have uncertainty. And he said, I always ask three questions. What do you want? Do you want to want that thing? And what does that decision say about who you are? Yeah, let's talk about the kind of identity. When we're in these indecisive places, we want to make decisions that we can stand by as people that reinforce the type of people that we want to be in the world. And coming back to my own job decision about the design firm versus the journalism job, I decided to say yes to the design firm.
1:29:05And in that moment, I had this incredible sense of self-doubt. Did I make the wrong choice? Is the journalism industry going to blacklist me forever? Have I done something horrible? I went from this place where I had all these options open to me to foreclosing on those options. And it felt like a loss. But as a person, I wanted to be someone of my word. And I said, yes to the design firm. And so attaching it to my identity, the way I self-justified it to myself was, I said yes to this job. I want to be a person that is good on his word. And so therefore, I'm going to do this. And if I make this grave mistake, then I can course correct in the future.
1:29:42And I think that is an empowering mentality when it comes to these crossroads in our lives or these moments of uncertainty. How can you be the person that you want to be regardless of the outcome? So as we wrap here, I would love to hear, I know there's a few more practical things that we haven't touched on. Take us through some of that because I think it's important. Yeah. So we talked a little bit about how to handle acute uncertainty. That's like a question like, will I pass the bar or will I get this job that I want? Thinking about things like separating what you can and can't control, trying to contingency plan for different outcomes, and then ultimately doing what you can to regulate your body so that you can accept whatever decision you get.
1:30:23But I think there's also this realm of uncertainty that is sort of ambient uncertainty of the world that we're living in right now. And one of the biggest things that I think can help us in these moments of ambient uncertainty is to think about ways in which you can trust in your future self to be able to handle some of your future problems. So I have this friend named Emily who is a therapist. She's like a therapist to the stars. She works with entrepreneurs and people navigating uncertainty and change. But when she was in her early 20s, her mom was given a potentially terminal diagnosis. And so for weeks, Emily was by her side in the hospital and really struggling on this sort of roller coaster of anticipatory grief and fear.
1:31:11And one day, a family friend of hers named Bill, who's an oncology doctor, so has a lot of experience dealing with people end of life, came to visit her. And Bill said, Emily, how are you doing? And she says, honestly, not very well. I don't know what I'll do if my mom dies. And Bill said, Emily, the version of yourself that will handle that tragic situation if or when it occurs will be born into existence in that moment. And that version of you will have more context, more information and be better equipped to handle that tragic event than the version of you today. You have to trust in your future self to be able to solve your future problems.
1:31:57And love that idea because so often when we are faced with uncertainty, we think about the worst case scenario. We think about all the things that could go wrong. We catastrophize. We go to control the future allows you to not rush out to meet your suffering. If you're able to trust in your future self, you can be able to handle that moment if or when it occurs. And for Emily, for example, she's so glad that Bill gave her that pep talk because her mom ended up recovering. She didn't waste all of this energy suffering about something that didn't actually come to pass. And so when we are faced with that career crossroads or that relationship uncertainty, step one, separate what you can and can't control.
1:32:47Step two, focus on one right action at a time. And step three, choose curiosity over fear. And if you just take away one thing from this conversation or the book, uncertainty, yes, can be threatening and uncomfortable and the source of a lot of fear. but it can also be the birthplace of possibility. If you're allowing yourself to approach uncertainty with that sense of curiosity, you might discover things that you might not have otherwise been aware of. Simone, thank you for coming in, man. Look, none of us love uncertainty, but getting better at it, I never thought of it as a skill. It's a good way to look at it because it's almost like lifting weights.
1:33:31Oh no, I'm in all these uncertain situations. Good, I'm going to get some reps in and build this life skill that's going to serve me forever. And I think that's a pretty cool and healthy way to look at things. Especially in this world that we live in right now. Yeah, no kidding. Thank you very much. Thanks for having me. Chess isn't just a game. You're about to hear a preview where Danny Wrench shares how building chess.com put him face-to-face with cheaters, death threats, and a past he had to rewrite to survive. I was born into a cult. As I've talked about it more and more, I've gotten better at just saying that, naming it for what it was.
1:34:05The collective itself was called the Church of Immoral Consciousness. My generation, within a couple of years, was part of the first group of kids that were being born into the collective, which, again, at that point, it was full communism. People's finances emerged. When you came to the collective, you gave up all of your material belongings. You just sort of look at it and go, this was fucked up. This was not okay. There is no excuse to be made for this. And then Western media was paying attention to chess for the first time, maybe since Bobby Fischer in the 70s. This movie had come out and these two kids trapped in a cult were basically under house arrest and didn't have anything else to do.
1:34:40And anything that Stephen Camp was fond of, everybody was into, right? He was literally in charge of every human being in the collective. I went from zero to being one of the top kids in the country. Within two years, I was already an All-American. I was one of the top rated players. And I've worked very hard to heal my relationship with my own abusers. not because I'm trying to excuse their behavior, but because I really do believe that forgiveness is not rewriting the past. It's freeing yourself from it. And so with chess.com, accidental success 15 years later. So we have 25 million games a day, 623 games finishing every second.
1:35:16You can have a different relationship with your experiences if you want to. The obstacle can be the way and you can overcome hard shit. That was my goal with this. To hear the story of how Danny Wrench got on the hit list, check out episode 1289 of The Jordan Harbinger Show. Today's lesson, certainty feels amazing, which is exactly why it should make you suspicious. So does cocaine. So does yelling, I've done my own research into a Facebook comment section. Feeling good is not the same thing as being right. The goal isn't to become indecisive. It's to stop worshipping certainty like it's some kind of wisdom.
1:35:50Get curious, run experiments, write down your predictions, invite people to challenge you, ask what you're missing, and when some overconfident clown tells you they know exactly what's coming next, maybe check whether they're a real expert or just a dart-throwing chimp with a ring light. All things Simone Stolzoff will be in the show notes on the website. Advertisers, deals, discount codes, and ways to support this show, all at jordanharbinger.com slash deals. Please consider supporting those who support the show. Don't forget about 6-Minute Networking as well over at 6minutenetworking.com. I'm at jordanharbinger on Twitter and Instagram.
1:36:21You can also connect with me on LinkedIn. In this show, it's created in association with Podcast One. My team is Jen Harbinger, Jace Sanderson, Robert Fogerty, Tata Sidlowskis, Ian Baird, and Gabriel Mizrahi. Remember, we rise by lifting others. The fee for the show is you share it with friends when you find something useful or interesting. In fact, the greatest compliment you can give us is to share the show with those you care about. So if you know somebody who's dealing with uncertainty and maybe could use some of the strategies and advice here in this episode, definitely share it with them.
1:36:47In the meantime, I hope you apply what you hear on the show so you can live what you learn and we'll see you next time.
From the publisher
Why does not knowing feel worse than bad news? How to Not Know author Simone Stolzoff shows us how to make uncertainty work for us, not against us.
Full show notes and resources can be found here: jordanharbinger.com/1326
What We Discuss with Simone Stolzoff:
- Certainty feels like wisdom but often isn't — Phil Tetlock found the average expert predicting the future is about as accurate as a dart-throwing chimpanzee, yet we keep mistaking confidence for competence and rewarding the loudest voice in the room.
- Our brains are wired for the savanna, not the spreadsheet. The same alarm bells that once warned us about rustling bushes now fire over phone storage decisions, leaving us anxious about choices that have almost nothing to do with survival.
- We hate ambiguity so much we'd choose guaranteed pain over uncertainty — one study found people facing a 50 percent chance of a shock felt more stressed than those facing 100 percent. Not knowing whether you'll lose your job hurts as much as actually losing it.
- Intolerance for uncertainty traps us in mediocre jobs, mediocre relationships, and mediocre lives. The "safe" choice quietly becomes the costly one, because the breakthroughs — entrepreneurial, creative, personal — all live on the other side of not knowing.
- Treat uncertainty tolerance as a muscle you can train. Take a new route to work, order the unfamiliar dish, run small experiments, write down your predictions, and trust your future self to handle future problems — that version of you will have more context than the one worrying today.
- And much more...
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