1326: Simone Stolzoff | How to Make the Most of Uncertainty

Summary

Podcast Summary: The Jordan Harbinger Show – Episode 1326: Simone Stolzoff | How to Make the Most of Uncertainty

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Episode Overview

On this episode, Jordan Harbinger sits down with Simone Stolzoff, author of How Not to Know, to unpack the psychological roots of our craving for certainty, why overvaluing it can backfire, and how to build a healthy, practical relationship with uncertainty.

Through a blend of scientific research, illustrative stories, and actionable advice, the conversation explores why not knowing can sometimes feel more painful than knowing something bad is coming, how “certainty traps” hold us back, and how some of the best breakthroughs—both personal and business—come from leaning into the unknown.

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Key Discussion Points & Insights

The Human Obsession With Certainty

• Certainty is comforting but often deceptive: Humans are biologically wired to prefer certainty, an adaptation that served our ancestors well but now gets misapplied to modern dilemmas.

  • “If you are in the jungle and there’s like a rustling in the bushes... that uncertainty could potentially be lethal.” – Simone [11:06]
  • In today’s world, the stakes are much lower, but our intolerance for uncertainty is undiminished.

• We seek closure, sometimes at painful cost: Research shows people often prefer bad news over ambiguity. “We would somehow rather know a bad thing is going to happen to us than have to deal with the ambiguity of not knowing.” – Simone [42:03]

• Technology has eroded our uncertainty tolerance: The instant answers of the internet and smartphones reduce our patience for ambiguity in other spheres, making us worse at navigating inherently uncertain situations. [15:28–17:03]

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Certainty Traps and Their Consequences

• Certainty becomes a liability in fast-changing environments:

  • Overconfidence blinds companies and individuals to new opportunities or risks. Examples: Blockbuster, BlackBerry, and a detailed breakdown of how the company Tiny Spec pivoted from an online game (Glitch) to create Slack by facing reality and abandoning sunk costs. [21:58]
  • “Uncertainty can also be the birthplace of possibility.” – Simone [22:50]

• Comfort, Control, and Hubris – The Three Certainty Traps:

  • Comfort: Choosing what’s familiar over what’s potentially better.
  • Control: The compulsion to predict and shape every detail of the future.
  • Hubris: Overidentifying with one’s expertise and shutting out new information.
  • “On the other side of comfort is growth, on the other side of hubris is humility, and on the other side of control is acceptance.” – Simone [61:56]

• Expert overconfidence can be counterproductive:

  • “The average expert was roughly as accurate as a dart-throwing chimpanzee.” – Simone referencing Phil Tetlock’s research [12:28]
  • Experts may ignore disconfirming evidence (replication crisis, marshmallow study) or trespass into commentary outside their domain. [67:08]

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Embracing and Using Uncertainty

• Decision-making under uncertainty

  • True commitment must emerge “in spite of doubt, not in the absence of it.” (Citing Rollo May) [07:45]
  • Instead of obsessing over perfect decisions, prioritize decisions you can be proud of, even if the outcome is uncertain. [09:49]
  • Jeff Bezos’ “one-way door vs. two-way door” decisions: Don’t overthink reversible (two-way door) choices; just take action and iterate. [33:26]

• Uncertainty tolerance is a trainable skill:

  • Small, deliberate exposures to uncertainty—trying new things, changing routines, or making low-stakes experiments—help build resilience and adaptability. [44:01]
  • “You have to trust in your future self to be able to solve your future problems.” – Simone quoting advice from an oncology doctor [01:43, 89:53]

• Practical tools for managing uncertainty:

  • Identify and anchor in parts of life you are certain about (family, rituals, values), so you’re better equipped to handle uncertain domains. [18:47]
  • Use “red teaming” (actively challenging your own beliefs), run experiments, and write down predictions to avoid certainty traps.
  • Distinguish between decisions that are truly high stakes and those that are easily reversible; avoid wasting energy on the latter. [34:53]

• Designing healthy uncertainty into life and work:

  • Periodically introduce new experiences, projects, or routines to disrupt staleness and encourage growth (the “explore-exploit tradeoff”). [55:53]

• Intellectual humility breeds credibility:

  • “The best leaders… understand what they know, what they don’t know, and are able to communicate both.” – Simone [27:13]
  • Clearly communicate unknowns and process, not just certainty, for greater trust.

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Notable Quotes & Memorable Moments

• On the value of experimentation in life:
  “They said, we’re going to run an experiment for a year. We’re going to go our separate ways, and then come back in a year and decide.” – Simone on the couple’s “Year of Living Dangerously” [04:27]
• On the futility of prediction:
  “Any prediction about the future is not certain. By definition, it is some level of chance.” – Simone [11:06]
• On being the coin for indecisive friends:
  “I know that I’m just a human coin. And they wanted to roll the dice.” – Jordan [76:09]
• On comfort versus adaptability:
  “Ultimately, it makes us less adaptable and resilient.” – Simone [64:07]

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Timestamps for Key Segments

• 02:14 - Episode theme and introduction of uncertainty concept
• 04:17–08:36 - The “Year of Living Dangerously” couple’s experiment and lessons
• 09:40–13:13 - Certainty’s biological roots, expert prediction fallibility, and the modern mismatch
• 15:28–17:34 - How smartphones and instant answers erode uncertainty tolerance
• 18:47–20:15 - Certainty anchors, rituals, and dealing with personal loss
• 21:58–23:19 - Slack origin story: Pivoting from a failed “sure thing”
• 33:26–34:53 - Bezos’ one-way vs. two-way door decisions, opportunity cost of overanalyzing
• 42:03–43:07 - 50% pain vs. 100% pain study: The stress of not knowing
• 55:53–58:26 - The explore/exploit tradeoff over the life cycle and Spotify analogy
• 61:20–61:56 - Disinformation, commitment escalation, and the lure of conspiracy
• 72:09 - Simone’s own hard career choice, diminishing returns of information gathering
• 80:04–81:05 - Practical decision frameworks: expansive vs. contractive choices
• 88:37 - The three reflection questions for identity-aligned decisions
• 89:53 - The concept of trusting your future self in times of uncertainty
• 93:14–93:36 - Treating uncertainty tolerance as “reps” for building a life skill

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Actionable Takeaways

• Distinguish between reversible (two-way door) and permanent (one-way door) decisions; don’t overthink the former.
• Build uncertainty tolerance through small, low-stakes experiments and new experiences.
• Anchor yourself with certainties—values, rituals, relationships—when facing unknowns elsewhere.
• Practice intellectual humility: Own what you don’t know; credibility follows.
• For big choices, ask: What would make me proud, even if it fails? Does this align with the person I want to be?
• When assisting others with hard decisions, act as a human “coin”—sometimes they just need a push.
• Trust in your future self to handle future problems; don’t catastrophize what hasn’t happened.

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This episode ultimately reframes uncertainty not as a source of fear, but as a necessary ingredient for growth, innovation, and a richer life. Simone Stolzoff and Jordan Harbinger provide not only the mindset shifts, but also the practical strategies to make the most of not knowing what comes next.

Transcript

[A]

This 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 and built in intelligence that makes updates around your schedule, not in the middle of it. They don't build tech for tech's sake, they build it for you. Find technology built for the way you [e-mail] DellPCS built for you. You're listening to this podcast, so I

[B]

know you've got a curious mind. Here's a helpful fact you might not know yet. Drivers who switch and save with Progressive save over $900 on average. Pop over to progressive.com, answer some questions and you'll get a quick quote with discounts that are easy to come by. In fact, 99% of their auto customers earn at least one discount. Visit progressive.com and see if you can enjoy a little cash back. Progressive Casualty Insurance Company and affiliates national average 12 month savings of $946 by new customers surveyed who saved with Progressive between June 2024 and May 2025.

[A]

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[B]

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.

[A]

Welcome 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. These 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 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, move 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 Stoltsoff, 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 overleveraged 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 grownup. We'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 Stolzoff 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.

[B]

First of all. Yeah, it's a pleasure to be here.

[A]

You open 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?

[B]

They were married. They've been together for 17 years.

[A]

So most people would say this is kind of insane.

[B]

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 the 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. They 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.

[A]

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? Because. 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, otherwise, why would you take a year off from your spouse? Come on, man, they knew already.

[B]

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 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. And the other half is like, no, there's no way. If they spend a year giving their energy outside of the relationship, it's a plane that's tilted a few degrees. They didn't have kids. And the spoiler is out there. They ended up breaking up. And so I talked to lots of people about it. 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 buy a new pair of jeans. If you're super intolerant of uncertainty, you 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?

[A]

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, ah, just gimme the first one. I do know people like that, but I can't relate at all. That's making me itch somehow, psychologically.

[B]

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. How can I develop the conviction to make a choice regardless? Gosh.

[A]

Okay, so what do you think Most people misunderstand about this experiment?

[B]

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 in 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. One of my favorite quotes is from this guy named Rolome, 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.

[A]

What did that experiment, you think, reveal that a normal breakup wouldn't have revealed?

[B]

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, is to have a clear sense of who you are and what your values are. So that you can make a choice, and 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. And 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.

[A]

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 gonna spend it all on essentially nothing like goodwill.

[B]

Totally. Like, the business is hemorrhaging money, and he's trying to make a choice to spend more money to fost 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. And 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?

[A]

Wow. Okay. So designed uncertainty versus accidental uncertainty is what I took from that.

[B]

Yeah.

[A]

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, oh, I missed you so much. And she's like, actually, I have another boyfriend.

[B]

Yeah, I forget what movie it was. It was some, like, Jennifer Aniston movie or something. And they're like, okay, I'm three. We're gonna say what we want from our relationship. One, two, three. And one person says, a divorce, and the other says, like, 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.

[A]

Why are humans so obsessed with certainty, even when we might not be that great at predicting things?

[B]

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. That 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 market is going to crash or exactly how the relationship's 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. When prediction is easy, when we can feel like we can anticipate is 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, et cetera. And his finding was that the average expert was roughly as accurate as a dart throwing chimpanzee.

[A]

How can that be the case?

[B]

We are just really bad at predicting the future. We whether it's something like what the interest rate is going to be next quarter or when the Iran war is going to end, we 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.

[A]

So we're not wired wrong, we'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 a hundred 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 ChatGPT gaming out the amount of photos that you're gonna be taking on. Like, none of that is necessary. But you give a good example in the book, there's this guy who gets like two MP3 players.

[B]

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 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 because 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. I'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 Carleton, 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 that 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, but 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.

[A]

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? He's like, no, no, no, don't Google it. We can try to figure this out.

[B]

What is he, a McKinsey consultant?

[A]

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 mule the same thing? And 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.

[B]

And then you Google it anyway.

[A]

Turns out they're different. I had no idea. Forty 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? How is a mule different from a donkey? Let's ask Grok. And 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?

[B]

I mean, I think. I'm not arguing for the value of not Googling things.

[A]

No, no, no.

[B]

I'm just. You want to find a fact that is demonstrably true, look up the fact.

[A]

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?

[B]

And it can create expectations. 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. There'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.

[A]

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. So 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's true.

[B]

My mind is blown. Yeah.

[A]

Cause 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. Cause it's the only thing you haven't seen 58 times. And it's hysterical, and you want to see it. Same thing with, like, Team America, World Police. I 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.

[B]

Come with us.

[A]

And then you watch it and you go, this. That was genius. Cinema.

[B]

Totally. Then you're just singing America. Yeah.

[A]

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?

[B]

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. What 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. I'll give one practical example. My grandmother passed away last week. She was 99 and a half. 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.

[A]

It was nice of her to wait until you had your book tour to give you that example to use.

[B]

Grandma's. Grandma, hold on until. Matt.

[A]

She's always, always thinking about you. What's a real world example of where certainty maybe makes somebody worse at their job?

[B]

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. In 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 $17 million before it launched, and 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. And 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. 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.

[A]

Okay.

[B]

And that founder, Stuart Butterfield. The company sold for 27 and a half billion dollars to Salesforce. It became one of the fastest growing enterprise software companies of all time. But 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.

[A]

That'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.

[B]

But it ended up being a big bet. It's what statisticians call overcoming a local maxima. So you imagine 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.

[A]

Yeah, I guess having certainty reduces cognitive load. Right. If 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. Yeah, I guess I'll just go back to work now. You know, like, I appreciate that about organized religion in some way, or religion in general. I suppose our brains are really prediction machines. You Kind of touched on that with the rustling in the bushes. And we love to know what's gonna 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 gonna happen next. But we like doing that.

[B]

It makes us feel warm and fuzzy inside.

[A]

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 or watch the movie over and over, watch the same video over and over. And for you and I, that's boring. I asked an expert, why do they do that? Because I watch 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 Ms. 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. I 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, and it's like, well, of course you were right. It's the same. And you've heard the song before.

[B]

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. The 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 ten 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.

[A]

You mentioned that research showing experts are basically as accurate as it was a dart going chimpanzee.

[B]

Chimpanzee, yeah.

[A]

So why do we still trust confident people if they're wrong all the time?

[B]

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. And it's really seductive and easy to follow those steps. The problem is it's easy until it's not. Yeah, sure.

[A]

See also every cult ever. And I guess we just assume confidence projects credibility. What is our discomfort with uncertainty? What does that reveal?

[B]

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. The 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. 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.

[A]

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 it's like, no, no, no, you can't do that now.

[B]

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.

[A]

This episode is about how planning can become anxiety in a little productivity costume. On 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. This 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. When 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 Bolan 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. So sheets matter more than people think. They're sitting right at the point where your body's trying to dump heat. That's why Bolen Branch is such a great sleep upgrade. Their summer bedding is breathable and lightweight. And their sheets are made from 100% organic cotton, woven for airflow, not just softness. Airflow, that's the key. The percale sheet set is what I use all summer. It's crisp, cool, breathable. The kind of sheet you slide into and immediately think, oh, okay, this is what adult bedding is supposed to feel like. It's a simple upgrade, but once I felt the difference, I just cannot go back to regular bedding. Sleep cooler this summer with Bull and Branch. Get 15% off your first order plus free shipping at bull and branch.com jordan with code jordan. That's Bull and Branch B O L L a n d branch.com Jordan Code Jordan to unlock 15% off bull and branch.com Jordan Code Jordan exclusions apply. Don't forget our free course, Six Minute Networking. It's about building your relationship skills and developing relationships with other people in a non cringy, very down to earth way. Just systems, no awkward strategies or cheesy tactics. Very practical in a few minutes a day is all it takes. Many 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 [e-mail] now back to Simone Stolzoff. 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 alpha male thing where 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 the 70s or something like that, or the 40s. And he basically came out 30 years later and was like, yeah, that was wrong. It 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.

[B]

Or like so many of the mid 20th century experiments were just run on like white male college students.

[A]

Yes.

[B]

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 human race.

[A]

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 the risk was so you'd be a few months behind and have to do something else. But in my mind I was like, no, I'm going to be homeless and my family's 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.

[B]

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. So 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. And 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.

[A]

So when you say that experts aren't really correct most of the time, Having confidence in a prediction, is that a scam signal?

[B]

Not necessarily. You want to look at someone's bona fides, their research, their reason for having confidence and opinions. Of course, if someone has the accolades and 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.

[A]

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.

[B]

But a PhD isn't necessarily a water airtight plan to show that someone is going to be correct about what they're saying. The 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. So 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, okay, I've already made my bet.

[A]

What's the best way to sound credible without faking certainty?

[B]

It's to be clear about what you don't know.

[A]

There you go.

[B]

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 can go back to Cesky 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 a matter of weeks or months or years. But he found certainty about the things that he could communicate about. So he increased his cadence of how often he was communicating with his team. And he said, okay, 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.

[A]

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, in certain tasks. I'd love examples of that because I think most people are like, wait, that doesn't sound right.

[B]

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. The 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, 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.

[A]

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. It's like you're super intolerant of uncertainty.

[B]

Yeah, they call it the doubting disease.

[A]

Oh, do they? Oh, I've never heard this. Yeah, I find that really interesting. I'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 mini disc 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.

[B]

Yeah, I mean, there's different types of OCD and it shows up in different ways. For 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. 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. It's not necessarily the heroin itself that they're seeking. It is the high that comes from the heroin. And. And for people with ocd, often the certainty is like the heroine. 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 1:37 or the 2:05 train back home to see his family for Thanksgiving. 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.

[A]

So OCD folks need less uncertainty to feel more. 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?

[B]

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. What they found was the people who had a 50% chance felt far more stressed than people who had 100% chance. So we would somehow rather know 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.

[A]

We.

[B]

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. And 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.

[A]

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?

[B]

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. 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.

[A]

How do you train yourself to not default to that instinct? Or is that not possible?

[B]

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 with spiders but 20ft away. And then eventually, you might allow a spider to get close to you. The 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 microdoses 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. The 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.

[A]

Are there benefits to those who are good at uncertainty? I mean, it seems like there naturally would be, yeah.

[B]

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. Where they don't know what is to come, continue to persist. The 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. 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.

[A]

Yeah, 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, 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, Right?

[B]

So 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.

[A]

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 at the law firm, people were like, you could better hope they never find out and you better da, da, da. And 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 going to 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 was it. But it is quite ironic that turned out to be much safer than my regular paycheck.

[B]

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 you. There weren't necessarily models of that all around you.

[A]

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. It 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 100 bucks an hour or 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? There's no risk. And then like I said, Career services was like, here's the risk that you're

[B]

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. That gave you more confidence to see yourself as a podcaster and pitch yourself to Sirius.

[A]

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 the $5,000 retainer. That 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. And he goes, you know who else isn't 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. They were like, I will do nothing to screw this up. Meanwhile, 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 who cares?

[B]

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. Two, 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. And what I tell them is the best way to learn about whether you want to be a writer or 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.

[A]

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. But the flight is part of the experience, too. Just like a great hotel can shape an entire trip, so can a great flight. That's exactly what Lufthansa Allegris is built around. On a long haul route, comfort matters more than people realize. If you're cramped, tired and can't relax, you feel it the second you land. But when a flight is comfortable, you can actually stretch out, rest, work, or just enjoy the ride. It changes the whole trip. I was thinking about that on my recent Intercontinental Lufthansa flight. I got so comfortable, I honestly didn't want the flight to end, which is not something you say very often after a long international trip. That's why Lufthansa Allegris stands out. It's built around the idea that people travel differently. Lufthansa Allegris Business class has five seat options. You've got the suite, the privacy seat, and the extra long bed. The extra space seat and the classic seat so you can choose what works for you. And that's what I like most. It feels elevated, but still practical. More privacy, more comfort, more thoughtful design for the way people actually travel. Now visit lufthansa.com and search for Allegris to learn more. Lufthansa Allegris all it takes is a yes. Limited availability on select routes. More routes coming soon this episode is sponsored in part by AT&T. You know why I love summer? All those plans we made. They finally make it out of the group chat. Seems like there's more time to fit everybody in whatever you've got in store this summer. Capturing those memories is a must. That's why I love the iPhone 17 Pro I picked up from AT&T. Its center stage front camera auto adjusts the frame to fit everyone into group selfies. You don't even have to turn your phone. No awkward cropping or asking strangers to take it. Just the perfect group selfie every time. And AT&T makes sharing those moments with everybody easy because you gotta share the pic or it didn't happen right right now at, at and t ask how you can get iPhone 17 Pro on them with eligible iPhone. Trade in any condition requires trade in of iPhone 15 or higher excluding iPhone 16e and 17e requires eligible plan Terms and restrictions apply. Subject to change. Visit att.comiphone or visit an ATT store for details. This episode is sponsored in part by Progressive. You ever think about switching insurance companies to see if you could save some cash? Progressive makes it easy. Just drop in some details about yourself and see if you're eligible to save money. When you bundle your home and auto policies, the process only takes minutes and it could mean hundreds more in your pocket. Visit progressive.com after this episode to see if you could save Progressive Casualty Insurance Company and affiliates. Potential savings will vary. Not available in all states. If you like this episode of the show, I invite you to do what other smart and considerate listeners do, which is take a moment and support our amazing sponsors. They do make the show. All the deals, discount codes and ways to support the podcast are searchable and clickable on the [e-mail] deals if you can't remember the name of a sponsor, you can't find a code or something's not working for you. Email us jordanordanharbinger.com Someone 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? Would 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.

[B]

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 one that they listen to. This 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 that 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, 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 in 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. And 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.

[A]

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 Oakenfold. And 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.

[B]

It's like, that'd be going too far in the exploring direction.

[A]

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, eh, okay, maybe this is not this way. And so it leads you in these different directions. Or it used to do that. Right. Remember what, you used to scroll from side to side and be like, here's what you're listening to now. Yeah. And eventually you get to, I don't know, like, Boards of Canada where it's like, what the heck is this?

[B]

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.

[A]

Yeah. And then your friends make fun of you endlessly for listening to some weird, obscure Canadian electronic experimental music. But, 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?

[B]

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. And 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 updating your belief isn't just changing your mind. It is potentially undermining your own self image. And 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. The 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

[A]

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.

[B]

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. But 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.

[A]

Some kind of mental gymnastics gets them back to the circle.

[B]

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. And 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 in 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. And 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. Or they're too comfortable without being able to expose themselves outside.

[A]

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. And we were done. We took the exam. She goes, what are you going to do with your book? And I was like, oh, 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's like, well, you said you were going to sell it. And 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 in pencil in here. I have to get rid of this. And I was just like, oh, my God.

[B]

I mean, talk about the need for control, huh?

[A]

It just made me think, what things are you doing that you don't let other people see?

[B]

I'm excited to look at her stock drawer.

[A]

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.

[B]

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. So 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.

[A]

Where do I eat?

[B]

Exactly? Where should I live? What should I wear? And on 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 this computer algorithm. He's staying where it's comfortable, which is not having to make choices himself and take responsibility for his own choices. And 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.

[A]

What's an early warning sign that maybe comfort has turned into stagnation?

[B]

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. So 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 on the complacency spectrum, maybe need to push yourself towards some novelty, if you're a little bit too far on this 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.

[A]

I 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.

[B]

Yeah.

[A]

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?

[B]

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. And all these other things.

[A]

Oh, yeah, what is it called? Intellectual trespassing.

[B]

Yeah, exactly.

[A]

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.

[B]

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 I 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 you may have heard of, say, like the marshmallow study.

[A]

Oh, yeah, the marshmallow test. So we tried that with our kids, and then. Yeah, I've heard that. Maybe it's just bullshit.

[B]

Yeah, I mean, it just hasn't been able to be replicated. And so your ability to, like, withstand eating a marshmallow doesn't actually predict your future life outcomes and not actually the things that correlate or like 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. And 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.

[A]

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.

[B]

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'm not sure. I'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.

[A]

But a lot of people, a lot of smart people double down instead of updating. So what's going on there?

[B]

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. And so we'd rather double slow down than update our beliefs.

[A]

Even though updating our beliefs is what builds trust from the outside perspective, and

[B]

it's what allows you to see the world in a more accurate way.

[A]

Yeah, okay. And control. We try to plan everything even when it doesn't work. I guess that's just also human nature.

[B]

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. The problem is you don't always have power to control the things that we try to control. And so you might have 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. And 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, to be okay with not knowing.

[A]

Where does planning become a control addiction?

[B]

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 for my life. I was once deciding between taking a job at this prestigious magazine or at this design firm. And 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 could control exactly what my future would look like. And 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.

[A]

And so which job did you take?

[B]

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. And I wrote my first book, and 10 years later, I'm a full time author.

[A]

Amazing. Okay, so that turned out fine. Good thing you wasted all that time thinking about. No, I mean, come on. There was a. 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.

[B]

I don't give a fuck what job these are.

[A]

Right?

[B]

Yeah. Yeah.

[A]

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. This episode is sponsored in part by LinkedIn. Running a small business means every hire matters. A bad hire can cost you time, money, and momentum. A good hire that can help you grow your business. This gives me flashbacks to a nightmare hire in my previous company that really stunted the business, and even talking about it now makes my blood pressure go up. But the right hire is the exact opposite. Somebody who takes ownership, solves problems and helps the business grow faster. And when you're small, that kind of impact is massive. But finding great talent isn't easy, especially when you don't have the time or resources to sift through piles of resumes to find the right fit. That's why LinkedIn built Hiring Pro, your new hiring partner that screens candidates for you. So instead of sorting through applications, you spend your time talking to candidates who are actually a good fit. With Hiring Pro, you can hire with confidence, knowing you're getting the best talent for your business. And in fact, Those hiring with LinkedIn are 24% less likely to need to reopen a role within 12 months compared to the leading competitor. Join the 2.7 million small businesses using LinkedIn to hire get started by posting your job for [e-mail] harbinger terms and conditions apply. This episode is sponsored in part by Conspirituality Podcast. You know how I'm always talking about critical thinking and spotting manipulation? Well, there's a podcast that's all about dismantling New age cults, wellness grifters and conspiracy mad yogis. Basically, the wild overlap of spirituality and misinformation. It's called the Conspirituality Podcast. The hosts, a journalist, cult researcher, and a philosophical skeptic, dive deep into how this stuff spreads from Project 2025 and the Heritage Foundation's dystopian vision of the future to how former leftists get pulled into far right conspiracies. An interesting episode to check out is called Speaking Truth to goop, where Jen Gunter breaks down the pseudoscience behind the wellness industry in a way that is super entertaining and and eye opening. It's sharp, funny, and makes you a lot harder to fool. Which, if you listen to the show, you know I'm all about that. From exploring cults to analyzing our cultural and political landscape, the Conspirituality Podcast will help you stay informed against misinformation and resist fear tactics. Find conspirituality on Apple Podcasts, Spotify, and wherever you get your podcasts, 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 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. One 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.

[B]

Totally. Then they can react to something.

[A]

Yeah. And then if they push back a bunch, I go, huh, interesting. It's almost like you really want the other one instead of. And then they're like, yeah, actually, you're right. No, that's. You're 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.

[B]

Totally.

[A]

And they wanted to roll the dice.

[B]

Whatever decision they're going to make is probably going to be half.

[A]

Exactly.

[B]

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. It'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.

[A]

There you go.

[B]

You can sort of retroactively which you're

[A]

going to do anyway. Probably.

[B]

Exactly. But first you have to be able to transact, you have to make the decision.

[A]

Do we need to design more uncertainty into our lives? Is there a benefit to that? Or is that already just happening so much?

[B]

If your life is too fixed, if you're too far on the exploit side of the spectrum, I do believe you'd benefit from exposing yourself to more uncertain situations. But 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.

[A]

Wait, is that real?

[B]

Based on the metrics that they use. So they track dimensions of uncertainty in newspapers, et cetera. But you think about it, it's like

[A]

I thought, I thought, okay, people's perception of uncertainty. Because I'm like, man, surely some Roman Empire.

[B]

The industrial revolution. Yeah, like the bubonic pledge, World War II. Since the study began in the 80s.

[A]

Okay, okay, okay.

[B]

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 that an all time low. And so what it does, exposing yourself to uncertainty is it prepares you for future uncertain moments that you might be exposed to.

[A]

Okay, I'm glad we clarified that because I was just thinking, surely if you

[B]

lived in Florence during the bubonic plague, you're like, oh, I'm sorry about your little overseas geopolitical fight right now.

[A]

Right, sorry. The Strait of Hormuz was closed, but my entire family was wiped out by a plague.

[B]

Yeah, yeah.

[A]

Okay, that makes sense. 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 low stakes?

[B]

Yeah. So for example, one thing I've been doing for myself recently is I hate marketing. I hate having to try and push a buck onto people. I like to be sort of like the writer behind the scenes.

[A]

Yeah, not gonna work really, but not okay.

[B]

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 is actually has an ROI for me or not. I 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 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. How can you prototype it?

[A]

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 shoo 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.

[B]

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.

[A]

I don't know about you. There are so many jobs where I would love to intern or shadow somebody for a week. It 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 really can't.

[B]

But I wish I hadn't said that.

[A]

Yeah, but imagine even. And some of them, 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. Like, you could do that.

[B]

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.

[A]

Now 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?

[B]

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.

[A]

Tell me what you mean by expansive versus contractive.

[B]

So I'll give you a personal example. When I was in my early 20s, I was trying to figure out what I wanted for 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 in 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. And 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.

[A]

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. So 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. No, that was the girl that, like, answered my email or whatever, right? That was the girl that kept talking to me after an hour.

[B]

There's freedom in that constraint as well. I think the paradox of choice. Too often our problems today are through abundance as opposed to scarcity.

[A]

Yeah, it was just. 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's 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.

[B]

Yeah, 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, 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. And 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.

[A]

It's interesting, we hired a nanny and Jen had gone and like care.com and talk 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 under qualified and you get a 19 year old who's like, I'm not going to do that and I'm not going it to do this. And I want a one week off per month because I gotta fly to New York to see my boyfriend and I want a green card. All these crazy things. And so we're like, all right, we're gonna start this interview process. And the first person we interview is like a 50 year old woman who has four kids, all successful. One'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 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 going to hire her if they've interviewed 50 people and she walks in the door. So we just hired her on the

[B]

spot and how did it work?

[A]

And we were like, yeah, she's been here for four years.

[B]

It's amazing because you knew what mattered to you.

[A]

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.

[B]

And 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.

[A]

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, they'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. It's like, ugh, you gotta draw the line somewhere.

[B]

And there 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 clickbaity title, but it said, why you'll marry the wrong person. It was by this guy named Alain de Botton. 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. You can work on Wall street, you make a lot of money, really long hours might 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. And 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?

[A]

Yeah, let's talk about the kind of

[B]

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. And 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 for 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. And 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?

[A]

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 and take us through some of that because I think it's important.

[B]

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. But 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. And 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 and 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 on these sort of mental loops. But not being able 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. 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. Step 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.

[A]

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. Oh, 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,

[B]

especially in this world that we live in right now.

[A]

Yeah, no kidding. Thank you very much.

[B]

Thanks for having me.

[A]

Chess isn't just a game. You're about to hear a preview where Danny rench shares how buildingchess.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. The collective itself was called the Church of Immortal 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, and these two kids trapped in a cult were basically under house arrest and didn't have anything else to do. And 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. You 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 Rench 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. Get curious, run experiments, write down your predictions and 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 [e-mail] deals Please consider supporting those who support the show. Don't forget about six minute networking as well. Over at 6minutenetworking.com I'm ordanharbinger on Twitter and Instagram. You can also connect with me on LinkedIn and in this show. It's created in association with podcast one. My team is Jen Harbinger, Jace Sanderson, Robert Fogarty, 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. In 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. Here's a riddle for you. What costs less than my coffee actually makes me money and makes my mom proud? A domain from Wix. Mine cost me less than 2 bucks and only took a minute to register and I even built a whole website in minutes using WIX Harmony. After two years of dragging my feet, I'm finally in business. Don't wait like I did. Get your [e-mail] domains. That's wix.com domains. And, Doug, there's nowhere I wouldn't go to help someone customize and save on car insurance with Liberty Mutual, even if it means sitting front row at a comedy show.

[B]

Hey, everyone, check out this guy in. What is this, your first date? Oh, no. We help people customize and save on

[A]

car insurance with Liberty Mutual together. We're married. Me to a human, him to a bird. Yeah, the bird looks out of your league. Anyways, get a [e-mail] or with your local agent. Liberty. Liberty. Liberty. Liberty. My name is Mackenzie, and I started a GoFundMe for the adoptive mother of a nonverbal autistic child. The mother mother had lost her job because she wasn't able to find adequate care for this autistic child.

[B]

So she really needed some help with

[A]

living expenses, paying some back bills. So I launched a GoFundMe to help support them during this crisis, and we raised about $10,000 within just a couple of months. I think that the surprising thing was by telling a clear story and just like, really being very clear about what we needed, we had some really generous donations from people who were really moved by the situation that this family was struggling with.

[B]

GoFundMe is the world's number one fundraising

[A]

platform, trusted by over 200 million people. Start your GoFundMe today at gofundme.com that's gofundme.com gofundme.com this podcast is supported by GoFundMe.