The One You Feed - Why the Need for Certainty Is Holding You Back | Simone Stolzoff

Episode Date: June 30, 2026

In this episode, Simone Stolzoff explores why the need for certainty is holding you back and how learning to live with uncertainty can lead to greater resilience, better decisions, deeper relationships, and a more meaningful life. Drawing from psychology, neuroscience, philosophy, and his own deeply personal experiences, Simone explains why our brains crave certainty, why that instinct often fuels anxiety and overthinking, and how embracing the unknown can become a source of growth rather than fear. If you’ve ever found yourself stuck waiting for the “right” answer before moving forward, this conversation offers a wiser—and more freeing—way to navigate life’s inevitable uncertainty. Free Guide: Outsmart the Hidden Saboteurs of Self-Control. What's been holding you back lately? In this free guide, Eric shares the six common saboteurs that quietly derail our best intentions—like autopilot behavior, self-doubt, and emotional escapism—and offers practical strategies to help you regain control and move forward. Download your free copy at oneyoufeed.net/ebook. Key Takeaways: The concept of uncertainty and its discomfort in a world that demands quick answers. The parable of the two wolves and its relation to embracing uncertainty. Biological and evolutionary reasons for the discomfort associated with uncertainty. The impact of technology and instant answers on our tolerance for uncertainty. Psychological traps related to certainty: comfort, hubris, and control. The importance of reframing uncertainty as a source of possibility and growth. Decision-making strategies and insights from experts on navigating uncertainty. The role of doubt as a positive force in decision-making and personal growth. The balance between exploration and exploitation in life choices. Personal experiences with uncertainty and their impact on life perspectives. For full show notes, ⁠click her⁠e! If you enjoyed this conversation with Simone Stolzoff, check out these other episodes: Embracing Uncertainty: The Key to True Intimacy and Connection in a Chaotic World with Prince EA How to Embrace Change for an Authentic Life with Najwa Zebian This episode is sponsored by: Quince: Refresh your wardrobe with Quince by going to Quince.com/feed for free shipping and 365-day returns. Now available in Canada, too. ⁠Shopify⁠ – The commerce platform that helps you build, grow, and manage your business all in one place. Start your $1/month trial at ⁠shopify.com/feed.⁠ ⁠David Protein⁠ bars deliver up to 28g of protein for just 150 calories—without sacrificing taste! For a limited time, our listeners can receive this special deal: buy 4 cartons and get the 5th free when you go to ⁠www.davidprotein.com/FEED⁠ ⁠Alma⁠ has a directory of 20,000 therapists with different specialities, life experiences, and identities, and 99% of them take insurance. Visit ⁠helloalma.com⁠ to learn more! ⁠Talkiatry⁠⁠⁠⁠ connects you with licensed psychiatrists for personalized, evidence-based mental health care, all online and covered by most major insurance plans. To get matched with an in-network psychiatrist in just a few minutes, visit ⁠⁠⁠⁠Talkiatry.com/FEED.⁠⁠⁠⁠ ⁠⁠⁠⁠Tiny Health⁠⁠⁠⁠‘s at-home gut health test provides science-backed insights into your microbiome, along with personalized recommendations to help you improve your digestion, energy, and overall well-being. Get $50 off your first test kit at⁠⁠⁠⁠ tinyhealth.com/FEED⁠⁠⁠⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

In order to build this uncertainty tolerance, we have to tell ourselves a different story, which is that uncertainty does not necessarily mean danger. Welcome to the one you feed. Throughout time, great thinkers have recognized the importance of the thoughts we have. Quotes like garbage in, garbage out, or you are what you think, ring true. And yet, for many of us, our thoughts don't strengthen or empower us. We tend toward negativity, self-pity, self-pity, jealousy or fear. We see what we don't have instead of what we do. We think things that hold us

back and dampen our spirit. But it's not just about thinking. Our actions matter. It takes conscious, consistent, and creative effort to make a life worth living. This podcast is about how other people keep themselves moving in the right direction, how they feed their good wolf. Simone Stolesoff was finishing a book on the value of uncertainty when he, He and his wife learned they were expecting. At a checkup around three months, the doctor couldn't find a heartbeat and asked them to come back a week later. So they waited.

He'd just been writing about how the waiting is often the hardest part. Now he was living in. They ended up losing the baby. What stayed with him wasn't only the grief. It was how present that week made both of them. And that's what we get into. How to stay close to your life when you can't know how it turns out. out. His book is How to Not Know, the Value of Uncertainty in a World That Demands Answers. I'm Eric Zimmer,

and this is the one you feed. Hi, Seymoh, welcome to the show. Thanks so much for having me. I'm really excited to talk to you about your latest book, which is called How to Not Know, the value of uncertainty in a world that demands answers. And this is a topic near and dear to my heart in many ways. But we'll get into it after we start the way we always do, which is with the parable. And in the parable, there's a grandparent who's talking with their grandchild, and they say, in life, there are two wolves inside of us that are always at battle. One is a good wolf, which represents things like kindness and bravery and love.

And the other is a bad wolf, which represents things like greed and hatred and fear. And the grandchild stops, they think about it for a second. They look up at their grandparent and they say, well, which one wins? and the grandparent says the one you feed. So I'd like to start off by asking you what that parable means to you in your life and in the work that you do. First and foremost, I love this parable because I find it to be so true. As a naturally doubting and uncertain and ruminating person, I chose to dig into this topic of uncertainty precisely for the truth.

the theme of the parable, which is we can choose to see uncertainty as a threat, as a source of fear, to catastrophize, to think of everything that will go wrong when we're in an uncertain situation, or we can feed that other wolf. We can choose to see uncertainty as the birthplace of possibility, as the precursor to learning and growth. And I often think about it in the context of this piece of advice that you sometimes give to people who are learning how to ski or snowboard, board, which is look where you want to go. And often, if we spend too much time looking at uncertainty as a threat, as a source of fear or anxiety or worry, that's where we go. And yet, if we're able to flip our frame, to change our mindset, and to see uncertainty as the place from

which learning and growth and development and possibility and opportunity is all born, we can start to move in that direction as well. Yeah, as a wannabe surfer, I'm learning. Don't look at your board. You have to look where you want to go on the beach. I am told consistently, I only get to do it about twice a year, so I never actually get better, though. But the point is a good one.

And what I like about your book is that it's part of a philosophy of why uncertainty is really valuable. and all these things we talk about and we'll get into that, but it does a really important thing also, which is it's lovely to know that uncertainty is good for us. It's a whole other thing to learn to tolerate it long enough that it can do good for us

or to even tolerate it in general. And I think your book does a really nice job of doing all those things. Thanks for saying, Sam. Yeah, I think that idea of tolerating it for long enough is a really important learning that I had through the reporting and research for the book. There's this comedian, John Cleese, who you might be familiar with from the Monty Python, and he was asked to speak at a big company one day. And they asked him basically, how are you able to be so creative? How are you able to continue to produce such original work? And I loved

his answer. He said, I'm willing to stick with a problem for long enough. And he has another friend, colleague in his office that is smart and has good intentions but never seems to produce truly original work. And Cleese basically says the difference, I think, between me and him is that he always goes with the first solution that comes to his mind, whereas I am more willing to stick with the problem. And I think that is exactly what you are saying about the value of building uncertainty tolerance, is that you can stick with the issue, stick with the problem, stick with your life for long enough to have that breakthrough for the possibilities to emerge as opposed to just going for the safe route or the quickest way away from uncertainty. This feels particularly relevant in our current moment where AI has the ability to shepherd us right past all the sticking with a problem long enough to come up with new ideas.

Yeah, very much so. In some ways, AI is a certainty machine. machine. You know, it gives you the probabilistic expectation of what you hope to receive based on the question that you ask. And especially speaking with young people, I see this all the time where they think that because they can answer some of their questions with a chat query or the right prompt that all of life's questions should be able to provide such immediate gratification or uncertainty. But I also see it to myself, you know, whereas 10 years ago I might have been okay, not knowing the name of a given actor.

Now I feel almost involuntary need to reach into my phone. And so I think all of our tolerances for uncertainty by nature of being in this hyper-connected digital age are at risk of deteriorating. Right. So uncertainty is naturally uncomfortable and is kind of built into us. And we're going to get into some of the biology of all that. But I think you're making a point, which is that we've gotten. worse at it because we don't have to endure it as much. Yeah, well, there's two things going on.

One is the world is getting more uncertain. So there's this economist from Stanford named Nicholas Bloom, who's been tracking global uncertainty since the early 80s. And he's found that the five highest measurements since he began studying the phenomenon have all occurred in the last five years. So you're thinking about the pandemic and shifting tariff policies, AI, and these wars overseas. So the world is more uncertain.

The trend that is less often talked about is what we were just talking about, which is the decrease of our tolerance for uncertainty. And primarily this is correlated with the rise of the Internet and particularly the rise of mobile phones. I think phones do two things. One is they bring all of the world's uncertainties to our pockets. So now we can track the real-time updates of a war overseas or what's happening in the straight of Hormuz. And we can also track the real-time locations of our children. all this information that hasn't necessarily made us any wiser and often just fuels our anxiety. The thing that phones do is they rob us of the practice of sitting with what we don't know.

And I know that you're a Zen practitioner, you know, a lot of what I've gleaned from my meditation practice is the value of feeling that discomfort, feeling that pain, feeling that uncertainty, and not rushing to solve it right away. And so the world is more uncertain, our tolerance for uncertainty is in decline. And that's why I argue so many people feel anxious and unbored. So when I read the title of your book, the first thing that popped into my mind is a Zen koan that talks about this that I was like, I'll bring that Zen co-on to the conversation. And then about three pages into the book, I was like, he's already got it. So why don't you share that with us? Yeah, another sort of teacher and student moment.

There's these two monks that meet in the forest. And the older monk, the more experienced monk, asks the student. what are you doing here? And the student says, oh, I'm on a pilgrimage. And the monk says, what are you on a pilgrimage for? And the student says, I'm not sure yet. And the monk says, not knowing is the most intimate. And I remember being in like a sangha in a meditation circle and the teacher telling us this koan. And I was like, not knowing is the most intimate. What the heck does that mean? The thing that I feel most intimate when I don't know something is Google, you know. But it's really changed my perception of uncertainty.

And I think what intimacy and my interpretation, what that means here is more proximate to reality as it actually is. When we are certain, when we think we know exactly when the market is going to crash or when the relationship is going to end or what the future of AI is going to bring, it has a sort of narrowing effect that closes our mind. But if we're able to maintain that not knowing mind, maintain that uncertainty without rushing for easy answers, then we can see the world as it actually appears, as it emerges. And so by not knowing sort of the purpose of this pilgrimage, the student is more open to what the pilgrimage might teach him. Yeah, and I think it's approximate to reality and I think it's also an attention mechanism. Right. When you think you know something, you stop paying attention to it. it. Whereas when you focus and give it more attention, and in that case, it actually becomes more

intimate because I think a lot of intimacy for me is about the things that I'm paying attention to. I am more intimate with. Yeah, it's beautiful. I think about that's when I'm traveling all the time. I'll be in a foreign city that maybe I've never been to before. I'll see an old man reading a newspaper outside of a cafe on the corner and say, oh my God, it's the most beautiful thing I've ever seen. And yet when I'm in San Francisco walking around, there's probably plenty of old men reading newspapers that I just don't notice because I have this assumption that I know where I am. Yeah. Okay. So let's start with talking about why is uncertainty so uncomfortable.

We can talk about it being something that's ultimately good for us. And yet it is one of the hardest states to be in. Why is that? It's biological. Cool. So you can think about it from an evolutionary standpoint. If one of your ancestors is in the jungle and there's a rustling in the bushes and they don't know the source of that noise, that uncertainty could be lethal. It could be a saber-toothed tiger. I feel like it's always a saber-toothed tiger in these sorts of examples. I know. I'm wondering, like, what did the mastodon have a bad public relations person? I mean, it's always the saber-tooth tiger. Exactly. But, you know, I mean, I think the point stands, which is when we don't know, we can't plan. We can't necessarily. guarantee our survival. And that is our primary function. It's our desire to stay safe and secure. And so from a feeling standpoint, when we are certain, it makes us feel like we can plan and by extension that we are safe. It's why we like music that's based on repeating patterns when you can

anticipate what's to come. Uncertainty, on the other hand, makes us feel incredibly uncomfortable because if you don't know the source of that noise, maybe it is the tiger. The problem is that our brains are also wired to see a lot of false positives. We often perceive uncertainty as a threat when it might just be a discomfort of being in a new place that we've never been or the precursor to learning or a feeling that is necessary to go through to discover the possibilities that might be sitting on the other side of our discomfort. So in order to build this uncertainty tolerance, we have to tell ourselves a different story, which is that uncertainty does not necessarily mean danger. Uncertainty can potentially be the cause

of fear. It can be hard to deal with, but it can also be something that shows us something about ourselves or the world that we didn't previously now. So you talk about three psychological or behavioral traps, I may be paraphrasing you there, comfort, hubris, and control. And then you turn around and say, you know, each of those has a sort of a corresponding virtue that would go with it, openness, humility, acceptance. Talk to me first about the three comfort, hubris and control, because that's really how you orient the book. Yeah. So every nonfiction book needs its framework. and this is my framework. I originally wanted to call them the three horsemen of delusion, but my editor thought that was a little too highfalut and so we settled on the certainty traps.

I like it, but yeah, I get it. In many ways, you know, there are just these psychological tendencies that we have that keep us stuck without accepting uncertainty. So for comfort, for example, we all have a status quo bias. We probably all know a friend who's in a job or in a relationship that they know isn't quite working for them, but they'd rather the devil they know. They'd rather stay on the situation that is known and comfortable as opposed to exposing themselves to the uncertainty of what happens if they walk away.

For hubris, this is our tendency to be excessively proud, our tendency to think that we know best. And I think this shows up all the time in the business world where people claim to know exactly how many entry-level jobs will be wiped out by AI, or how the market is going to behave, over the course of the next 12 months. The last is maybe the most pervasive, which is control,

which is our desire to plan for all future outcomes, to need to know exactly how our career will progress, to need to know exactly what the future of the climate or our own death day will be. And although all of these psychological needs are born out of a place of wanting us to stay safe and secure and survive. They also come with costs. With comfort, if we are not willing to expose ourselves to uncertainty, we will never learn, not just our own preferences, but what we are capable of.

With hubris, it can be indicative of blind spots where you can't see ways in which you may be erring or not seeing an accurate picture of reality. And with control, our desire for control, particularly about things that we can't control, like macroeconomic conditions or climate change or these things in our life that are outside of our realm of influence, can suck so much of our energy and attention and take us away from the realm which we actually can control, which is our realm of influence. And so that's sort of the flip side of each of these traps. So on the other side of comfort is the growth and learning that comes from being outside

of our comfort zone. On the other side of hubris is the humility that comes from admitting what we don't or can't know. And on the other side of control is the acceptance that comes from being able to separate what is in and outside of our power. I've often said that depression hates a moving target, but there's a cruel irony in there because moving is one of the hardest things to do with depression. And similarly, when we most need a therapist, it is often when we have the least ability to sort through the complex mess of depression. finding one, which is why I'm such a big fan of what Alma is doing. They've made the search part simple because that's often the thing standing between us and getting help. Alma has a directory of over 26,000 therapists, and you can filter by things that actually matter to you, like specialty,

identity, life experience, therapeutic approach, and critically, you can put in what insurance you have and it will show you therapists who take that insurance. Over one million people have found care with Alma and 95% connect with a therapist within a week. If you've been thinking about starting therapy or getting back to it, I'd recommend checking out Alma. Get started at helloalma.com slash feed. That's H-E-L-L-O-A-L-M-A dot com slash feed. I think that's an important point to note because I often think sometimes we think that

we need to get to a place where we're not uncomfortable for things. to be valuable. I mean, it's sort of the opposite of the comfort question. But there's a line you have from a researcher. And I love it. She says, uncertainty is annoying, difficult, and stressful for a reason. Because if it wasn't, we wouldn't pay attention to it and take action. Yeah, I love that too. You know, uncertainty is what incentivizes us to say put on a seatbelt before we enter a car because we're not sure whether the car is going to crash or to maybe think twice before we reach for that Barry that we're not sure is poisonous. And so in many ways, like many of the sort of emotions in the negative register, they can be great teachers. They can be instructive and tell us what we might

need to pay attention to, even in the context of something personal, like a relationship. If you're uncertain about something, maybe that is a flag that shows that you need to have a conversation with your partner about it. It doesn't necessarily mean that you need to abandon chip or leave right away. But uncertainty is that teacher. It is that sort of internal alarm system that's saying, pay attention to this. This might not be in your favor. I want to talk about decisions. And you frame up this making decisions through three different people's perspectives, Irobedzo,

Esther Perel, and Ruth Chang. Share about those. So the broader context is that the book is narrative-based. So each chapter of the book is its own sort of mini-case study. And in one of the chapters, I profile a couple. And they have been together for 17 years, married for 10, and they're out having a drink at a bar in New York City. And they decide to do something that other people thought was insane.

They decided to go their separate ways for a year and then come back to the bar to decide whether they want to stay together 12 months later. They called it the Year of Living Dangerously. And I remember first hearing this story and I was like, wow, I have to write about this. is stranger than fiction. And I won't ruin the end. You'll have to read the book to find out what happens. But in the context of reporting this story, I reached out to all of these experts. So Esther Perel, is this famed couples therapist, Ira Bredzao, is this ethicist who was at Emory University.

And then Ruth Ching is a philosopher. So it's through three different perspectives on this question of what do you do when you're uncertain about a relationship, but it can also be extrapolated to other facets of life. And they each have their own. perspective. One of the lines from Esther Perel that I really loved was that trust is an active engagement with the unknown. So so many people come to Esther and they say, how do I know whether I found the one or how do I know whether I am in the relationship or I should go on another date? And the truth is, you can't know, especially not at the outset. You can't know whether this person is the right person or be your one and only love or is worth exploring until you've actually transacted.

until you've actually been able to take some of those leaps and find out whether they continue to show up. And so I love that idea of trust being an active engagement with the annual. Bredzile is an assist, and so he works both at a hospital and with college students helping them figure out their career. And whenever someone comes to him with an uncertain predicament, he always asks them the same three questions. And I love them all. The first is, what do you want? Pretty straightforward. but the idea here is to get out of your head and into a more embodied sense of desire.

The second is, do you want to want that? Which is little heady, but it's what ethicists talk about as your second order desires. So sort of your desires of your desires. So do I want to smoke a cigarette? Sure. Do I want to want to smoke a cigarette? Maybe not. You're sort of more reflective self.

The third question, which is the one that I like the most, is what does this choice say about who you are? And why I like it is because when we're making a decision, when you're at that crossroads, and you can go left or go right, you can't necessarily know the outcome of your decision. And so that question, what does this choice say about who you are or who you want to be, taps into this aspirational version of ourselves. It helps align your choices with your values. And if you make a choice that's aligned, hopefully you can stand by your decision, even if you don't get the outcome that you desire.

And the third is this woman, Ruth Chang, who's a philosopher, and she says that what makes a hard decision hard is not that one option is clearly better than another, and you're just too stupid to work it out. What makes a hard decision hard is that one option is likely better for some reasons, another option is likely better for others, and neither is better overall. So rather than agonizing of,

or trying to make the right decision or trying to find the perfect fit. She says, make a decision by whatever means you can, and then spend your energy telling yourself a story of why that decision is right, sort of retroactively weaving a narrative about all of the reasons why you made that choice. And I love that. You know, the example that she gives is imagine you're deciding what to eat for breakfast, and you're deciding between a bowl of fruit and a donut. the fruit is healthier.

The donut is more delicious, but neither is better overall. And so you go back and forth and back and forth, and you make pro-con lists and you talk to your yoga teacher about it and yada-di-y-a-data. She says, make your choice and then tell yourself the story. Today, I am going for the donut because donuts are delicious and I want to start my day with joy. And I think we can make lots of life's cross-road decisions from a similar vantage point. Yeah, I think the danger there, of course, is

the narratives that we can very easily tell ourselves about consistently making the donut choice, right, if we're not, if we're not careful. But I flip a coin for a lot of things. It drives my partner nuts. She's like, you can't just decide by flipping a coin. I'm like, yes, I can. Because I've spent five minutes and I can't tell the difference. And so it doesn't matter.

I also love the Ruth Chang one because it also says something I think is really important, which is that we're too stupid to know which. Hard choices are hard not because of our ignorance. And I've been in situations where I've had to make very difficult decisions. The biggest, most wrenching one for me was my last marriage, right? And it just went on a long time, lots of many decisions. But one of the worst parts was that I just kept feeling like I should be able to figure this out. And it was a little bit of a relief to me, a little turning down.

of my psychological distress to go, you can't figure it out because this is a really difficult decision. And like you said, I've got two choices. Neither of these is particularly the one I want, you know, or they're both good and bad in very different ways. And I think, so for me, for the trivial things, just making the decision is really valuable.

And those more important things, I do think knowing that it's natural for this to be really difficult. It's helpful. Yeah, there's a line from a psychologist that I quote in the book that I really like, this guy named Rollo May. And he says that commitment is healthiest, not in the absence of doubt, but in spite of doubt. And what I love about that is it is not making an assumption that you should be able to rid or banish doubt or uncertainty from your mind. But it's by making choices in spite of not knowing exactly. how they'll turn out that refines our character that makes us into who we are. I remember in my own life, this maybe lower stakes, but equally as distressing decision between choosing to take a job as a journalist or to work at this design firm. And San Francisco, the journalism jobs on the East Coast. And on one hand, it's like world's smallest violin, you know, the agony of deciding between two

attractive job offers. On the other hand, it really sent me for an exasel. substantial loop and, you know, maybe some of our listeners have been at a similar sort of crossroads where they can see two very distinct paths. There were sort of Simone, the designer on one path, Simone, the journalist on the other, and I was insufferable. I could not make up my mind for the life of me, and I talked about it with everyone I knew, and depending on the side of the bed I woke up in, I would change my mind. And what I realized, in retrospect, is exactly what you just said. What made the decision hard is not that there was a clear, right path. It was one path was better for some reasons, another path was better for other

reasons, and neither was better overall. And so what I had to do is be able to make a choice to commit in spite of my doubt, in spite of my uncertainty. And in many ways, this book is just sort of a balm for the 28-year-old that was trying to make that choice in my life. You know, we write the books that we need to read. Yeah. Well, that idea of the Harvard psychologist Ellen Langer, talks about not making the right choice, making the choice right. And it's the same thing that once you do, it's really very beneficial, as was suggested, to start the narrative about how this is the right choice and to live fully into that choice. You know, I remember the more recently, for me, my son trying to figure out college was a similar thing.

I just was like, there's no right answer here. There are variables we can't even begin to predict. that we just can't know. Who's your roommate? Do you have a good roommate? Do you have a bad roommate? Who are your professor? I mean, there's so many factors that we just don't know. Like, let's make an informed choice, but then ultimately just realize, like, once the choice is made, now we go live it. Yeah, as my Russian friend used to tell me, you make a choice and then you murder the alternatives, which I kind of like thinking of that.

Especially in the context of something like a college. You know, there's this decision strategist that I talked to for the book, this former professional poker player named Annie Duke. And she gave me this tool that I think is very helpful called the only option test, which is imagine you're deciding between going on vacation to two equally as attractive places. Maybe one is Rome and the other is Paris. And, you know, it's a high-stakes decision because it's expensive. You might not be able to take many trips like this in your lifetime. And so you agonized. you make pro-conblest, you flip the coin, you flip the coin again.

What she says is imagine someone had a gun to your head and said, your only option is to go to Rome. Would you be happy? And then imagine if that same person had a gun to your head and said, your only option is to go to Paris. Would you be happy? And if the answer is yes to both, maybe the decision matters less than you think.

And so for your son, for example, maybe he's choosing between two schools. what makes the decision hard is the opportunity cost, is knowing that choosing one school means foreclosing on his options of choosing other schools. But if he only had one choice to make and he would be happy, maybe that's a decision that he can make relatively quickly.

Yeah. It's the other thing that the coin toss does for me is that I almost immediately discover that I had a preference after all when the coin comes up. Like it's just I can feel it. I'm like, no. Or yet. Right? And if I still can't discern, then I'm like, okay, truly, either one is a perfectly good choice.

Before we dive back into the conversation, let me ask you something. What's one thing that has been holding you back lately? You know that it's there. You've tried to push past it, but somehow it keeps getting in the way. You're not alone in this. And I've identified six major saboteurs of self-control, things like autopilot behavior, self-doubt, emotional escape, that quietly derail our best intentions. But here's the good news. You can outsmart them. And I've put together a free guide to help you spot these hidden obstacles and give you simple,

actionable strategies that you can use to regain control. Download the free guide now at one you feed.net slash ebook and take the first step towards getting back on track. I want to move on to the next chapter, which has one of my favorite titles of any chapter in recent memory, which is the prison of our preferences. Yeah, so the story here is a story of a young fellow named Max, and he is a software engineer. In college, he actually studied software engineering in art, fine art, which I think is a little bit illustrative of the way that his career and his life developed. But his software engineer, he gets a job at Google, a sort of dream job. He moves out to the Bay Area. And after a few years of working, he has this uncanny feeling that his life is just sort of acting out this expected script.

But each day just feels like rinse and repeat. And he goes to the coffee shop that's highly rated on Yelp. And he takes the optimal route to work on his bike. And he goes to the exact bar that you would think a 24-year-old living in San Francisco would go to. And so he decides to shake things up a little bit in perhaps an extreme way, which is he starts designing algorithms to make decisions on his behalf. In many ways, they're sort of like the souped-up coin flips that Eric uses. And the first one he does is it taps into the Uber API and calls an Uber to his house

and brings him to a location in this city known only to the driver. So it's sort of like a roulette, Uber roulette. and so he gets to see all these different neighborhoods, these different places that he wouldn't have otherwise seen. Then he decides to dial it up a notch. And at the time, Facebook had this feature where you could see all of the public events in your area around you. And so he created his Facebook random event generator

that would just tell him a random event to go to in the city and then he would go. And at its most extreme, he quit his job, and he created an algorithm to choose where he lives around the world. So each month he would roll the dice and it would say Gortina, Slovenia, and he would pick up his bag and he would go to Slovenia and he lived there for a year or a month. And then at the end of the month, he would roll the dice again and says, Ho Chi Minh's city Vietnam. And he sort of lived his whole life this way for over two years.

And what I like about it is, in the short term, you might think this man is like an uncertainty expert. This is like our sense. We can learn so much about him from his tolerance of uncertainty his willingness to expose himself into new situations. But I interviewed this psychologist named Mikhail Dugat, who really helped change my mind. And Dugat was one of the first people to link intolerance of uncertainty with a lot of anxiety disorders that he sees in his patients.

And he says that when people are particularly intolerant of uncertainty, he tends to see one of two different behaviors. The first is people become obsessively. information gatherers. You know, we probably all have a friend who needs to read like 300 reviews on Amazon before they buy a plastic water bottle. Or we become extremely impulsive. And he says, neither is really an adaptive behavior. Like, imagine you're trying to buy jeans. The information gatherer will have to try on every pair of jeans in the store. The impulsive person will have to buy the pair of jeans in the window. But both are sort of avoidant strategies

to try to get away from the uncertainty that is inherent in making any choice in your life. And so on the surface where you might see Max as someone who is really tolerant of uncertainty by outsourcing the responsibility or the decision to the algorithm, he's in fact avoiding uncertainty. He's finding certainty and is not needing to choose himself. And so it was a fascinating chapter to report. And I think it taught me a lot about this balance between exploits, and exploiting, this balance between wanting to learn about the world and novelty and new

possibilities while also committing and having stuff that compounds that we can continue to return to and find meaning. When I was reading that chapter, I was thinking about a story about the musician John Cage that I read recently. And as his career went on, he was a Zen practitioner to a certain degree. So his idea was that the ideal music is the music, is the music in which the composer's ego is completely absent, absent from. And so he would be doing things like just using the I Ching to pick chords. He was taking it like to such an extreme that when I first start reading about, I'm like, wow, that is really cool.

And then I listen to somebody's music. And I'm like, hold on a second. Like, you know, there is a role for the composer to be making choices. Again, I think he was proving points often with his music, but to me it was that like, you know, how do we find the middle ground of I obsess over every last detail of everything I composed to the nth degree? Or I absolutely, to your point, outsource all the decisions to some random generator. And I think the conclusion I came to after I read that and that you're sort of coming to you right now is like, we got to find that middle place. that works for us. And the other thing that I think's interesting

about that explore, exploit dilemma, right? The explore is you just keep doing different things. The exploit is maybe you try something that compounds or you just keep, like, you know you've got a good restaurant, you just keep going to the good restaurant. And what I found interesting about that dilemma is I think we can be on different parts of that spectrum

for different parts of our lives. Like food-wise, I'm kind of an exploiter, like meaning that my, uncertainty tolerance on food is less, you know, or my window of comfort is less. But other things, it's a lot more wide. But I think the prison of our preferences is just such a, I just love it because I see how more and more, particularly as I age, more of my choices get made by comfort. That's the one that is driving the engine.

and it is not the one that I want driving the engine. I don't want to banish it to the outskirts. I think that prison of our preferences is a lot because, you know, if we look at Buddhism in general, there is a certain degree of, hey, you are suffering because you are very attached to this going one way or the other. Yeah. Yeah, at the very least, if you're too attached to one way of life

or one dish firm restaurant or one job title, you become fragile because that thing might get taken away from you or you might not be able to go to that restaurant or you might get laid off or furlode. And so that's one case for diversifying your preferences. North Star, don't even say that North Star could go away. I hope not. Don't even suggest it.

But I think there's tradeoffs on both ends of the spectrum. So if you do too much exploration, too much novelty, seeking, your life doesn't necessarily move in a particular direction. And this is what Max ultimately found. You know, he spent all this time traveling and seeing the world, but it had diminishing returns. Whereas if you do too much exploitation, too much leaning into what you already know and you like, that has a few costs as well. One is you might miss out on a preference that you didn't know you had, you know, the restaurant around the corner that you might like a little bit better, like better certain days of the week, or the dish on the menu that you didn't know

that you wanted to order. And so in addition to it being person dependent and dependent on maybe different facets of your life, I also think it changes a lot as we age. And people who are older might need a little bit less exploration as they become a little bit more classified in their ways. Whereas if you're younger, you might need a little bit more exploration as you're trying to determine your tastes and figure out who you are. But the most important takeaway in my mind is that we all need both. We need to have some certainty and some uncertainty to live a fulfilling life. Yeah, I mean, I think when it comes to that aging piece, you raise a point that I think about a lot, is that I notice tendencies of aging in myself that I don't generally like and resisting the things

that come with aging is not exactly a graceful way to go about it, but nor is giving into the tendencies that come with it. So, you know, figuring that out is always sort of a nuanced path. Yeah, very much so. All right, let's move on from here, and I want to talk about doubt. Talk to me about the role of doubt as a positive force. in our lives or the cost of not doubting whichever way you'd like to go yeah i mean they go hand in hand right if you're too overly confident if you don't introduce any sort of doubt or uncertainty into

your thought process you're prone to have large blind spots and we see this all the time there is a benefit to having expertise and experience but the cost is that we are these pattern matching brains, and if you always expect something to go a certain way, you might miss out on something that's outside of your purview. The classic image, which I really like a lot, is you can become a drunk man looking for his keys under the streetlight because that's the only place that's illuminated. And so one of the things that introducing doubt, or maybe in an organizational context, dissent, or in your personal life, some uncertainty, is, is it makes you think twice.

It makes you pay attention to what you might be missing. It makes you find evidence to support your claims as opposed to making assumptions that you know are right. The problem is that introducing too much doubt or too much uncertainty can be paralyzing. It can keep you from making a choice at all. There's just one study that I talk about in this middle section about hubris that I really like a lot. and it was conducted at the university, and they broke students up into small groups to solve a murder mystery. And a majority of these students were in Greek life, so fraternities or sororities.

And in certain groups, they were homogenous, so they were all people from the same frat or sorority house. And in other groups, they were more heterogeneous. They had people from different houses. and then they worked on the murder mystery and then came up with their results and then rated how effective they thought their group was. And the findings were fascinating. Groups that had diversity in them, of people from different houses, were correct at a much higher rate. They were better decision makers. And yet the process of coming to a decision, they rated as less effective.

Whereas people that were part of in-group, this home. homogenous group of people that were all in the same sorority, for example, had an easier time coming to consensus. They thought that they worked better together, but they were less effective. And I think you can take this finding and think about so many aspects of your life or your organization that probably falls in line, which is to say that when we are surrounded by people who always think like us, it feels good. There's less tension.

There's less friction. but often you're prone to blind spots and mistakes and your thinking. Whereas when there is a diversity of perspectives or of ages or people of different teams or people of different life circumstances, there is friction. And maybe that's by a design. That friction is what leads to more comprehensive decision making. And even though it doesn't feel as good, often the ultimate outcome is more accurate. And so that's sort of a tension that we're all having to navigate in the context

of our businesses or our lives or families or relationships. Maybe there's no better source of a frictionless decision than one that you only have to make with yourself. And yet when we surround ourselves with other people, there is always going to be a little bit of a rub, which is maybe by design. Yeah, that was one of my favorite studies in the book, too. I found it absolutely fascinating that you would objectively be worse at solving the problem but think you were better at it because it made you comfortable.

it made me think of a couple things. My career before I did this was in software. And so a lot of times, you know, we would get brought a problem as a leader. And there's like one person that knows the answer. Yeah. And intuitively, it makes sense to me. I'm like, yeah, of course, that's probably exactly what's happening. And sometimes that was the case.

And rushing down that path would get us to an answer far faster. But there were plenty of times that I rushed just a decision because the people that I most liked agreed with me. Now, I couldn't see that at the time. You know, the other story that it made me think of is I did this like outward bound expedition several years ago. And it's an organization that takes people out into the wilderness and trains them to do well out there. And so we were out on a nine-day thing. and in the beginning our guides sort of told us where to go

but as the week went on we had to make more and more of the decisions with a map and a compass the whole process was always uncomfortable as you broke into like four groups and in each group you're debating what's the right answer then you have to all come together

and all agree on the right answer and collectively so the whole process was fraught with that uncomfortableness but I remember one time all of us except one woman thought we knew the right way to go. And this woman was by nature a very retiring, shy,

not comfortable confronting people, but she just sort of stuck to her guns. And you can see where this is going. She was, of course, was the right one. And I just loved that story as another example of like, sometimes that, you know, that dissenting opinion as annoying as it is. because I'm just like, can we just wrap this up? I've got like a 40-pound pack on my back.

Here we go. You know, but she saved us hours. You know, she saved us hours by being willing to be the one that disagreed. And I think in a beautiful personal empowerment way, I think it was a huge lesson to her that like I can, you know, like I can have an opinion. It's valuable and it's right. It was just a, it was kind of a beautiful thing. That is beautiful. And I think the fact that she is by nature shy.

gives her more credibility. Because often, like, especially in a business team context, you're often listening to the loudest voice in the room or the person that gets paid the most's opinion. And it shows, you know, this is classic group think, right? If everyone starts thinking one way, you just want to get on the bandwagon. But if you're willing to stick to your guns

and back it up with evidence and share your thinking, that actually will ultimately lead to better group decision making. Yeah, the thing that I found difficult in that, work context also is that sometimes there's just the person that disagrees because that's what they do, right? And you're like, I don't really want to pay that guy a ton of attention, but sometimes he actually is right, you know, and so there's a tendency to be like, are you just slowing this whole process down, you know? Anyway, no short answers to any of that, but it certainly made me think about that as we looked at that chapter. There's a framework that

I like when it comes to making these types of decisions in a business context, which is rather than thinking just about consensus is what we're looking for, like everyone's saying yes or everyone's saying no, there's a middle ground, which is safe enough to try. And so rather than it just being we need 100% in or 100% out, being willing to run the experiment, being willing to try something, let's say, let's go for this direction in five minutes and then reassess. It's often a better way of trying to balance that tension between wanting to, you know, disagree and commit versus wanting to talk it over one more time. And that's beautiful going back to the prison of your preferences also.

Like, is this safe enough to try is a great question. Like, oh, I'm not really not losing that much by, you know, moving outside of what I would normally do here. I love the Voltaire quote, doubt is not a pleasant condition, but certainty is an absurd one. Yeah. Now, one of the things that I notice in the world, and I'm not alone in noticing this, is that certainty is very rewarded in a lot of places. You know, even if I look at the world that you and I are sort of in, which is, I don't know, I want to call it personal development, business advice, self-help, whatever you want to call it,

right? The people are really certain that they have the answers tend to do well in a lot of ways. is this just back to the uncomfortability of what uncertainty is and just as a people will just be like, I'd rather not wrestle with that question. I'd rather not have all the nuance. Yeah, I mean, we all want to hitch our wagon to the leader that has a very clear idea of exactly what the future will look like

or, you know, in the most extreme, maybe a cult leader who tells you exactly what the world is going to do or exactly the steps you need to take to get to heaven. And the problem is these hubristic leaders are attractive and not always correct. And so it's easy to sort of outsource your worldview or to say, okay, I'm just going to follow this politician or this CEO or this self-help guru into the dark. And yet, especially with anything that hasn't happened yet, the idea that we can be certain is a fallacy. and particularly in these moments like the one that we're living through right now where there is so much precarity and uncertainty,

the peddling of certainty just increases. You know, you turn on the TV and there's someone that's going to tell you exactly who's going to win the election. You open your app on your phone and someone tells you the food that you need to eat if you want to live to 100. And it's attractive. You get it. It sort of taps into this, you know, person in the jungle that's like,

oh, when I'm certain, then I feel safe, then I can plan, then I feel secure. The problem is it's often wrong, or at least not the whole story. Yeah. Yeah, I notice it in myself, and I think like my entire worldview is sort of nuance and questioning, and yet I feel the same pull. I'm like, maybe they really have figured out how to do 200 hours of therapy in 20 minutes. Right? Maybe this person really has cracked the code.

Yeah, exactly. Yeah, I mean, we all have that tendency in ourselves to look for the path of least resistance or the easier answer. And to say that it's nuanced or it's not black and white or maybe you're wrong is not as attractive. And I think it's true. For example, thinking about a CEO, no one wants a leader that just says, I don't know what's going to happen. And yet the leaders that say, this is exactly what's going to happen, you know, they are often wrong. And so I think we need a little bit. of both. We need the types of leaders who are confident about what they know are humble enough to admit what they don't know and who are willing to design a plan for learning and figuring things out. Yeah, I face this when I was writing my book because I'm a big believer. There's not like one size fits all solutions, right? Everybody's life is different. There's so many varying circumstances. So my natural tendency, if I'm not careful, is to hedge everything and caveat everything and create 8,000 pages worth of end notes. But at a certain point, then I'm just not saying anything, right?

To write it's complicated and hand it back to my editor is not exactly a good book. Yeah, I love that quote. All models are wrong, but some are useful. And, you know, I think it's true. You can't take a picture of the whole world. You need to put up a frame. You need to have constraints. And, of course, you know, lots of pieces of advice are one size fits all.

or overly prescriptive, but sometimes they sort of function like the coin flip, where they give you something to react to. And you don't have to necessarily accept it whole hog, but it's nice to have people who are willing to put a stake in the ground. So one of the things that I really liked in the book was sort of a two-by-two decision matrix. Can you share that with me? Yeah. Basically, the two axes are, is this a decision that is, of high consequence or the stakes high or is the decision of low consequence with lower stakes. And is it a decision that is in my realm of influence or is it a decision that's outside of my realm of influence? And we spend a lot of time focused on decisions that we have no control over

or decisions that are of low consequence. And what we should actually be spending our time is is only that one quadrant of high-stakes decisions that we have control over. And another way to think about this is through what you might know as this serenity prayer, which is very popular in any sort of addiction or 12-step program. God grant me the serenity to accept the things I can't control, the courage to change of things that I can and the wisdom to know the difference. I think the majority of the decisions in our day-to-day lives are in that low consequence. quadrant. They are about what to eat or what to wear or what to watch on the TV. And not to say that

those decisions don't matter at all, but you can often make those decisions quickly because the cost of making a wrong decision is relatively low. They're what are sometimes referred to as two-way door decisions where if you make the decision, you walk the door, you realize you made the wrong decision, you can walk back through that door. My friend Chris gets hung up though because he can't decide what closed where he often ends up just going out in public with nothing on. Poor Chris, or maybe a blessing to everyone around to him for the positive. Well, I'm not going to comment on the second part. All right.

The other types of decisions that are in our control are, obviously, you know, the decisions that are more like one way to our decisions, questions like, you know, should I marry this person? Should I buy this house? And those are decisions that warrant a more analytical decision-making process. The problem is when we take our frameworks from one-way-door decisions and apply them to two-way-door decisions. And I'm sure we all have a friend that will go back and forth and back and forth and whether they want to get the pizza or the pasta and then they put in their order and they change their order.

We could afford to be making some of those two-way door decisions a lot quicker. Yeah, I love that idea of there's one quadrant that's worth paying attention to. I think the tricky part, because I've thought a lot about this, I've lived with a serenity prayer for 30 years now since I came into recovery the first time, is that so many things don't fit cleanly into either column. And I think that makes things trickier. I was talking with somebody who'd had a chronic disease for a long time, right? And we were talking about how, you know, there's part of that process,

which is learning to accept that your life is kind of the way it is, but also recognizing there's things you can change. Or I think about like, you know, we could say like, well, you're not in control of your, you know, what happens with your finances, which ultimately is true. The stock market could implode tomorrow. There's nothing there. But there's a lot that I can influence in that. And that's why I love you using the word influence more than the word control, you know, because I do think a lot of these things are matters of influence. Even like, you know, I may not be able to control when I die, but I certainly can influence.

influence how likely that is to happen in, you know, next week. Yeah, I really like that distinction a lot. And it makes me think that we can make decisions that plan for that uncertainty, you know, in the same way that, like, an investor benefits from diversifying the stocks in their portfolio as a tactic that helps them hedge against a future market that they don't know. We can do that in our personal life, too. You know, my first book was called The Good Enough Job. is about the value of diversifying our identities beyond just what we do for work.

And one of the main arguments is that when you're able to see yourself as more than just a software engineer or an accountant or a lawyer, it allows you to have a more broad foundation so that even if you were to lose one pillar of your identity, the house can remain standing. And I think that's a lot of our work in this current moment where we don't know what the future holds. We don't know whether AI is going to understand. mind these industries or whether the president is going to lead us to a world war or what have you. But you can do things in your life that are both commitments in spite of that uncertainty and things that planned for an uncertain future like hedging.

I was thinking of going to the story of you and your wife, the pregnancy. And part of what I really like about that is that even as someone who knows all this about uncertainty, how living in it is actually still challenging. Yeah, so while I was reporting the book, my wife and I were trying to get pregnant for the first time. And we did, and we were so excited. We started planning the future. We got the app that says, you know,

how big is your baby based on what week you're at? And we started calling this unborn kid, Poppy. And about three months in, we were at the doctor's office. And she said, at this stage in the pregnancy, we'd expect to see a heartbeat. And I'm not picking one up on the ultrasound. right now. And, you know, of course, our minds go, oh, shit, I know what's happening. And she said, why don't you come back in a week and then we can do some more tests and see where we're at?

So not only did we have to deal with the prospect of miscarriage, but we also had to deal with the waiting. And I just been writing about these studies, about how, you know, a study at the University of College London where participants were given either a 50% chance of receiving a painful electric shock or an 100% chance of receiving a painful electric shock. And those with the 50% chance were far more stressed and anxious than those with 100% chance. Or a study of breast cancer patients where they found that the period between getting a biopsy and getting a diagnosis is often the hardest part of the entire breast cancer journey. It's the waiting. It's the uncertainty. And here I am writing about this stuff and then I have to deal with it in my own life. And I remember

that week very clearly. It was tough. There was no or two ways around that. But there were also some beautiful moments. My wife and I would maybe make eye contact in a crowded room or hug for a little bit longer. It sort of had a slowing down of time. We were very present in our experience. And sure enough, we come back to the doctor a week later, and it was what was called a pregnancy demise.

You know, we lost the baby. And what that story taught me is that, Uncertainty is tricky by design. You know, in the last chapter of the book, I talked about grief and death. And there's this one line that I keep coming back to, which is the fact that we live in the death-denying culture robs us of the ability to appreciate how we want to live.

And, you know, the loss was really hard and mass. This is a few years later, we were able to conceive again, and I think we appreciate that baby just a little bit more because we went through that negative experience. But all of the wisdom of the book, this idea of finding your anchors, of finding the things in your life that you are certain about, this idea of trusting in your future self, this idea of being willing to transact in spite of not knowing,

I got to live it in my own life. And every time I look at my son now, I think a little bit about that loss and how it helped me become more appreciative of the life that I do have. Before we wrap up, I want you to think about this. Have you ever ended the day feeling like your choices didn't quite match the person you wanted to be? Maybe it was autopilot mode or self-doubt that made it harder to stick to your goals.

And that's exactly why I created the six saboteurs of self-control. It's a free guide to help you recognize the hidden patterns that hold you back and give you simple, effective strategies to break through them. If you're ready to take back control and start making lasting changes, download your copy now at one you feed.net slash ebook. Let's make those shifts happen starting today. Oneefeed.net slash ebook. Well, that is a great place for us to end. Thank you so much for taking the time to talk with us. going to continue in the post-show conversation where I'd actually like to take those four

lessons of living with uncertainty that you gave us in 15 seconds and explore them a little bit more, some, you know, even more practical tools for living with uncertainty. So listeners, if you would like access to that and not have to live with the gnawing uncertainty of what brilliant thing did Simo say, as well as ad-free episodes and really importantly, supporting something that you know, with no uncertainty you love, go to one you feed.net slash join. Thank you so much, Seymoh. Thanks to have me on the show. Thank you so much for listening to the show. If you found this conversation helpful, inspiring, or thought-provoking, I'd love for you to share it with a friend. Sharing from one person to another is the lifeblood of what we do. We don't have a big budget,

and I'm certainly not a celebrity, but we have something even better, and that's you. Just hit the share button on your podcast app or send a quick text with the episode link to someone who might enjoy it. Your support means the world and together we can spread wisdom one episode at a time. Thank you for being part of the one you feed community.