Autumn: Hey everyone, welcome to the show! Today we're tackling something we all deal with: confidence. Seriously, how many times have you second-guessed a major choice, talked yourself out of something amazing, or maybe jumped into the deep end when you really shouldn't have? Confidence really dictates what we do and what happens to us, and honestly, we hardly ever stop to really examine it. Rachel: Exactly! Confidence is like this ultimate power-up, right? The more you've got, the better off you are. But is it really that straightforward? What if I told you that too much confidence could actually get you into trouble? And on the flip side, not enough could keep you stuck in your comfort zone forever? Autumn: Precisely. That's where this book comes in, because it totally rethinks confidence. Instead of pushing the whole 'more is better' thing, it argues for what it calls 'calibrated confidence'. Basically, it's about matching what you think you can do with what you actually can do. The book dives deep into psychology, throws in some real-world examples, and strategic thinking to show how being overconfident or underconfident can mess with your head and lead to bad decisions—whether you're leading a company, mapping out a project, or, you know, just trying to get through life. Rachel: Okay, I'm intrigued. So, today we're going to unpack all of this. We’ll hit three main points: First, why nailing that 'just right' level of confidence is so crucial. Second, how these hidden biases can totally sabotage our thinking, even when we think we're being logical. And third, some practical tools you can use, like probabilistic thinking and premortems, to basically sharpen your decision-making skills. Autumn: We'll explore the science, share some stories, and give you strategies to help you find that sweet spot when it comes to confidence. Ready to jump in? Let’s do it!

Autumn: Okay, so let’s really dig into this idea of well-calibrated confidence . Basically, it's about knowing yourself, as much as believing in your abilities . It’s hitting that sweet spot, right? Not “too” confident, where you're completely blind to potential problems, but also not so little confidence that you're too scared to even try new things . The trick is making your “actual” skills match how skilled you “think” you are . Rachel: Right, it’s that Goldilocks principle: not too much, not too little, but just right . But come on, Autumn, we all know that most of us aren't great at judging ourselves . Either we think we're geniuses who can do anything, or we're convinced we're completely useless . Why is it so hard to find that balance, do you think? Autumn: That's a great point . I think it comes down to cognitive biases . Think about the "better-than-average" effect, where everyone thinks they're better than average at something, which, statistically, is impossible . Or the planning fallacy—that overconfidence that your project will be done early, be cheap, and go off without a hitch... and that “never” happens . Rachel: Oh man, the planning fallacy . Remember that high-speed rail project in California? They said it would cost $25 billion and be finished by 2016 . Now, it's more like $77 billion, and it's still not done yet, right? Autumn: Exactly! Textbook overconfidence . Decision-makers often ignore risks because they're so focused on their vision of success . And what's really scary is it's not just personal—it affects everything . Overconfidence in decisions that big can undermine public trust, funding, and progress . Rachel: So basically, if you “don't” calibrate your confidence, you're not just messing up your own life; you could derail entire infrastructure projects . Okay, I get it . But what about when you're “under”confident? Because we’ve all met brilliant people who just don't believe in themselves . Autumn: That’s the other extreme, and it’s equally destructive . Imagine the talented students who don’t even bother applying to top-tier schools because they’re positive they’ll get rejected . The ability may be there, but they lack the belief . And what's so sad is that it's not just their loss; it’s a loss for everyone . These places need different perspectives, but that can only happen if people take the risk and apply . Rachel: Right, so it's like a self-fulfilling prophecy . "I'm not good enough, so I won't even try," and then, boom, the opportunity's gone . It reminds me of that author, Hugh Howey, saying about his writing, "I suck at it.” I mean, the guy's a bestselling author! If “he” doubts himself, then what chance do the rest of us have? Autumn: I know, right? It just highlights that inner critic that so many creative people struggle with . External success doesn't necessarily silence that voice of doubt . And that's why the idea of "calibrating" your confidence is super powerful . It's about being able to say, "Okay, here’s what I'm good at . Here’s where I need work . And here's how I can get better." Rachel: Okay, but how do you “actually” calibrate your confidence without going too far in either direction? Is there some kind of secret formula here? Autumn: Good question, Rachel . A great tool is something called a "premortem analysis." It’s a mental exercise where you pretend your plan failed miserably, and then you work backward to figure out why . Thinking about potential pitfalls ahead of time helps you see the areas you're blind to and forces you to be more realistic . Rachel: So, it's like playing devil's advocate with your own dreams . "Okay, my project blew up—what happened?" I see how that’s useful . It gives you a kind of roadmap of what to avoid . Autumn: Exactly! Another tactic is probabilistic thinking . Instead of relying on your gut, it’s about assigning probabilities to different outcomes . Instead of saying, "This is “definitely” going to work," try saying, "There's a 60% chance of success, a 25% chance it partially works, and a 15% chance it completely fails." It forces you to sit with the uncertainty and forces you to plan accordingly . Rachel: So, instead of betting everything on one outcome, you kind of hedge your bets . That makes sense . But doesn't that sound, I don't know, a little too cold? Where's the passion if it's all about risk percentages? Autumn: Well, I'd actually argue the opposite—that kind of clarity can actually make you “more” ambitious . Think about Alex Honnold free-soloing El Capitan . It was incredibly daring, right? But he prepped like crazy . He practiced every move to the point where it wasn't about being reckless, it was about calculated risk . And that’s really what well-calibrated confidence is all about . Rachel: The passion's still there, but it’s balanced with preparation and fact-checking with reality . So that's the "secret sauce," then? Autumn: Pretty much . Because when you have well-calibrated confidence, you're not setting yourself up for failure . You’re positioning yourself for meaningful, lasting success . It’s less about being fearless and more about being thoughtful . Rachel: Sure does sound better than walking across burning coals and just “hoping” for the best . Autumn: Every single time .

Autumn: Building on that, the book “really” digs into how this calibrated confidence plays out in society and in our own behavior. And one of the big takeaways is biases. They always seem to find a way into our decisions, twisting how we see things. I was “really” impressed with how the book handled this; it broke down the mechanics of these biases, gave some “really” convincing examples, and—importantly—suggested ways to deal with them. It was structured so well and very practical. Rachel: Exactly. Biases, like confirmation bias and the better-than-average effect, are “really” at the heart of why we make bad calls sometimes. These aren’t just little quirks we have; they change the choices we make and ultimately the outcomes, which can... well, shape history or, unfortunately, lead to disaster. Maybe we should start with confirmation bias, seeing as it's so common? Autumn: Absolutely, let's do it. Confirmation bias is everywhere. Rachel: Yeah, it is like a psychological "yes man." Confirmation bias is like that colleague who's always agreeing with your ideas, which then translates to an ability to filter out the dissenting opinions, which in reality is where you truly need the perspective, right? How does the book actually describe it? Autumn: Well, it defines confirmation bias as our tendency to actively seek out, interpret, and, yes, even remember information that supports what we already believe. At the same time, we end up dismissing or downplaying anything that contradicts it. A perfect example of this is the Cuban Missile Crisis. Back in October 1962, the U.S. leadership was pretty convinced that the Soviet Union was being explicitly aggressive and posing an immediate threat. And that belief “really” drove their decisions then. Rachel: Right, so when you're that rigid in your thinking, there's not much room to maneuver. So, what actually happened? Autumn: Well, the U.S. essentially based its entire strategy on defensive assumptions, and they were often blind to any other way of seeing what the USSR was doing. This inflexibility brought both sides dangerously close to nuclear war. It “really” took calculated diplomacy—and honestly, a bit of a cognitive reset at the last minute—to de-escalate things. The big lesson here is that biases, like confirmation bias, can trap you in one way of seeing things and make you miss other vital possibilities. Rachel: Wow, talk about flirting with disaster. I'm still amazed at how close we got to a global catastrophe simply because of a mental shortcut. But let's not pretend this is ancient history. Confirmation bias isn’t just for world leaders during the Cold War; it shows up in every heated debate at the office, every late-night argument online. So, how do people actually escape these ideological bubbles? Autumn: Well, one of the main solutions the book points out is to encourage different points of view and make sure that dissenting opinions aren’t just allowed, but they’re actually built into the process. Imagine a setting where every voice—no matter how different—is “really” taken seriously. For example, anonymous voting can stop groupthink because people aren’t influenced by louder voices. Rachel: That’s smart. So, instead of just ignoring the "wild-card thinker," you actually make their opinion more visible. Democracy in a brainstorming session, I like it. I get the logic, but it feels like we’re naturally inclined to defend our positions when someone disagrees. Does the book offer any alternative for breaking free from confirmation bias? Autumn: Yes, another extremely awesome tool is the premortem technique. It’s actually something we've touched on before on the podcast. It’s a process where you start by imagining that a project or decision has failed. Then, you work backward to figure out why. So instead of just jumping in with overly optimistic assumptions, you’re deliberately poking holes in your own plan. Rachel: Oh, so you're like playing offense against your own biases? That makes sense. Okay, now let's switch gears for a moment. What about the better-than-average effect? If confirmation bias is about creating your own reality, then the better-than-average effect is almost the opposite, right? It's about overestimating your own abilities, sometimes with bad results. Autumn: Exactly. It’s basically when you think you’re better than average at something, even when the numbers just don’t back it up. While that might make you feel better in day-to-day life, it can be “really” dangerous in high-pressure situations. One particularly scary example is the Lion Air crash in 2018. Rachel: Right, the one with the Boeing disaster. How does this bias relate to that tragedy? Autumn: The “really” interesting and sad thing is that the pilots were faced with a malfunctioning new automated system. Instead of “really” understanding the system, they were overconfident in their ability to fly the plane manually. This slowed down their decision-making because they assumed they could handle things themselves instead of figuring out what the technology was doing. And that resulted in a terrible crash that killed 189 people. Rachel: Wow, a tragic example that truly reflects a failure to course-correct both in flight and in mindset. The better-than-average effect can become fatal when there's a new environment or new tech involved where training and execution need to be perfectly aligned. Autumn: Exactly. And this is where realistic self-assessment is extremely important. As awesome as technology is, focusing on strong training and a full understanding of how systems work can prevent deadly mistakes. And to avoid the trap of overconfidence, some of the techniques we mentioned—like premortems or probabilistic thinking—can be adapted for use in critical industries like aviation. Rachel: Let me make sure I’m understanding this correctly—probabilistic thinking the one where you don’t try to make a single prediction but instead prepare for a range of possible outcomes? Autumn: Exactly. It basically means evaluating uncertainties and thinking about the chances of different scenarios happening. You might not get to one clear answer, but you avoid thinking in black-and-white terms, like "It’ll succeed or it'll fail." Life is usually more complex than that, and probabilistic thinking encourages you to take a more layered approach to decision-making, especially when a lot is at stake. Rachel: Alright, I see how this works in professional environments. But does this also apply to everyday life? I mean, what does probabilistic thinking look like in the regular decisions we make every day? Autumn: Absolutely. Think of it this way: instead of planning your day based on the assumption that "everything will go smoothly," you could assign probabilities to different things like traffic delays or unexpected weather. This way, you're adjusting your plans in degrees, not absolutes. It's a pretty subtle mindset shift, but this kind of thinking helps prevent frustrations or complete failures because you’ve already thought about the potential challenges. Rachel: So, the “really” big lesson here is humility—knowing what you don’t know, what could happen, and being ready for a reality check. I have to admit that it's not easy since our brains usually look for simple solutions instead of nuanced possibilities. Autumn: Yes, it “really” takes some mental effort to overcome those simple solutions. But once you “really” understand biases and how they affect you—how they distort your judgment—it becomes a lot easier to develop strategies to counter them. Ultimately, it’s about getting that calibration, not just in confidence, but in how you see and deal with complexity.

Autumn: So, understanding these biases is one thing, but really, the interesting part is figuring out how to deal with them, right? This book doesn’t just point out the problems; it gives you actual strategies to recalibrate your confidence and make better choices. We're going to talk about specific methods for getting to a more balanced sense of confidence. Things like premortem analyses, thinking probabilistically, getting different viewpoints, and creating a culture where constructive criticism is the norm. And the best part? These aren’t just theories; we’ve got real-world examples to show how useful they can be in leadership, decision-making, and even just growing as a person. Rachel: Okay, I’m listening. This "premortem" thing sounds like something out of a detective novel. What's the idea behind imagining a project failing before you even start? Autumn: It does sound a bit backwards, doesn't it? The premortem analysis, which was developed by psychologist Gary Klein, is all about flipping the usual planning process on its head. Instead of just focusing on how to make something succeed, you start by imagining that the project has already failed in the worst way possible. Then you ask yourself, "Okay, what went wrong?" This kind of reverse thinking can help you spot risks and blind spots that you might have missed if you were just caught up in the excitement of the project. Rachel: So you're looking for the weaknesses before you've even finished building, right? Do you have any good examples of times when this has really made a difference? Autumn: Absolutely. There was this massive, billion-dollar environmental project where a premortem revealed a risk that nobody in leadership had even thought about: the possibility of the CEO retiring in the middle of the project. Succession planning just wasn't on anyone's radar. But doing the premortem forced them to think about what would happen if that scenario actually played out. They were able to come up with backup plans, making sure that the project wouldn't lose steam even if the leadership changed. Rachel: So, by thinking about the worst-case scenario, they were ready for something totally unexpected. That's actually pretty impressive, and it sounds like a smart practice for any company. But what about for everyday life? I mean, not everyone is managing projects worth billions. Autumn: It's definitely something you can use in your personal life, too. Think about making a big decision, like switching careers or starting a business. Instead of just picturing the best-case scenario, imagine that it completely fails. Ask yourself, "Why would this fail? What skills, resources, or support do I need to keep that from happening?" It might be a bit uncomfortable, but it can really help you see things clearly. Rachel: So, instead of just trying to live up to some perfect image, you get a much more realistic view of what's involved. Sounds like good advice. Now, what about probabilistic thinking? That sounds like a math lesson wrapped up in a psychology course. Autumn: Actually, it’s more straightforward than it might sound. Probabilistic thinking is about moving away from these rigid, all-or-nothing predictions and embracing a range of possibilities. Instead of saying, "This is definitely going to succeed!" you try to estimate the likelihood of different outcomes. Like, "Okay, there's a 70% chance this will be really successful, a 20% chance of so-so results, and maybe a 10% chance it'll completely bomb." Rachel: So, you're hedging your bets, in a way? What's the advantage of doing that? Autumn: The big advantage is that it makes you more adaptable. When you acknowledge the uncertainties from the start, you're much better prepared for any setbacks. Take inventory management, for example. Companies don't just try to predict demand perfectly; they use probability models to plan for when customer needs change. That way, they avoid making costly mistakes by either overestimating or underestimating the demand. It’s the same idea when you're making personal or professional decisions – thinking in probabilities forces you to be both realistic and flexible. Rachel: It sounds practical, I suppose, but I can also hear people saying that it takes the passion out of decision-making. Do you think this kind of thinking can be “too” clinical? Autumn: I get why it might seem that way, but I think it can actually help you channel your passion more effectively. Think about Alex Honnold's free solo climb of El Capitan. He was incredibly passionate about it, but he also calculated every single aspect of that climb with incredible precision. His probabilistic mindset didn’t kill his ambition; it basically ensured his survival. By prepping for every possible outcome, he turned a potentially reckless act into a carefully measured success. Rachel: Good point – passion doesn't mean ignoring reality. Let's talk about getting different viewpoints. The book makes a strong case for this, especially in countering biases like confirmation bias. But how do you actually get people to disagree without things falling apart? Autumn: Well, it's about setting up structures where everyone is encouraged to speak up and is treated with respect. Think about Abraham Lincoln’s “Team of Rivals.” He made a point of filling his cabinet with people who often disagreed with him. They challenged his ideas, and all that tension actually helped him make better decisions during the Civil War. It's about seeing dissent as something valuable, not as a threat. Rachel: I like that. Definitely better than being surrounded by "yes men." So how can companies encourage that kind of environment today? Autumn: One way is to collect opinions independently before you have group discussions. So, for instance, when you're making hiring decisions, have each team member rank the candidates on their own first. That stops dominant personalities or groupthink from overshadowing other people's opinions. Research shows that this leads to better results, because you're actually considering every angle. Rachel: It's a simple but effective tool. It kind of reminds me of those murder mystery games – you put everyone's theories together to figure out who did it. Now, what about constructive criticism? That sounds easier said than done. Autumn: No question about it. Building a culture of constructive criticism really comes down to trust and accountability. A great example is Bridgewater Associates, Ray Dalio’s hedge fund, where they practice radical transparency. Any idea, no matter who it comes from, can be challenged, and no one gets a free pass because of their position. They record meetings, give constant feedback, and people rate each other’s contributions in real time. Rachel: That sounds… intense. I can imagine that kind of environment feeling like living under a microscope. Autumn: It is intense, but it can also be transformative. By creating that level of openness, you help people align their confidence with how they're actually performing, instead of just their ego. It gets rid of denial and bias, which leaves room for growth and better choices. It can be a real game-changer for organizations that are willing to embrace it. Rachel: Alright, so we've got premortems, probabilities, diverse perspectives, and radical transparency. I've got to say, these are concrete, actionable tools, and they're not just for CEOs or executives. It seems like anyone could benefit from these strategies.

Autumn: Okay, so to sum up everything we've talked about, today we really focused on what well-calibrated confidence actually means. It's not about being ridiculously overconfident or, you know, totally doubting yourself. It's about finding that sweet spot where your belief in yourself actually matches reality. And by understanding and tackling biases like confirmation bias and the better-than-average effect, we can make smarter, more well-thought-out choices. Rachel: Right, and the book also gives us some concrete tools to actually achieve that, doesn't it? From premortem analyses, where you basically imagine the project failing and then figure out how to prevent that, to probabilistic thinking, which gets you comfortable with uncertainty. These aren't just theories; they're ways to change how you view confidence and how you make decisions. Autumn: Totally. It's all about setting yourself up for growth, building resilience, and making choices that are both brave and based on solid information. Rachel: My big takeaway is that confidence isn't just some inherent feeling; it's a skill. And like any skill, you can sharpen it, refine it, and, well, calibrate it, as the book says. Autumn: Exactly. So, here's something for our listeners to think about: Where might your confidence be out of sync with reality? Maybe you think you're amazing at something when you're not, or maybe you're selling yourself short. Just being aware of that is the first step. Rachel: And once you know that, dig into the tools we talked about today. Get better at questioning your own assumptions, seek out other viewpoints, and think about all the possible outcomes. Success isn't about not being scared; it's about being equipped, ready to deal with whatever comes. Autumn: Absolutely! So, for our listeners, here's a challenge: Think about a decision you've got coming up. Use what you've learned today. Maybe think probabilistically, do a premortem, or just get someone else's opinion. See if those strategies change your confidence—and your results—for the better. Rachel: Sounds like a plan. Until next time, be bold, find your balance… and stay calibrated. Autumn: Bye everyone!