Why You Feel Stuck in Life | Simone Stolzoff

11 May 2026 · 58 min · 22 chapters

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In short

Why people feel stuck in life—Simone Stolzoff argues that uncertainty isn’t just a threat; it’s managed through three “traps”: comfort (staying in the familiar), information/optimization loops (seeking certainty instead of acting), and hubris (assuming you know best).

Key claims

Experts predict poorly (Phil Tetlock’s findings: average expert ≈ dart-throwing chimp). People also misjudge how they’ll feel later (lottery, breakups, accidents). Action—not more information—creates clarity; “action absorbs anxiety.” He recommends decision frameworks: distinguish fact vs hypothesis, use contingency planning, and make choices based on values/identity even without guaranteed outcomes.

Notable examples

A couple runs a “year of living dangerously” experiment—separating for a year to decide whether to stay together. A “helicopter vs hike” metaphor: AI can speed you to an answer but you miss the learning. He cites an MIT study where AI-assisted students didn’t remember what they wrote.

Guest

Simone Stolzoff is a journalist and author of How to Not Know, who spent three years studying how people handle uncertainty in careers and life.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

Introducing Simone Stolzoff

1:37 to 2:24

Introduction of guest Simone Stolzoff and his work on uncertainty.

“You have to trust in your future self to be able to solve your future problems.”

Understanding Uncertainty in Careers

2:24 to 4:21

Exploring how uncertainty affects careers and personal lives.

“Today we're talking with Simone Stolzoff, journalist and author of How to Not Know.”

The Challenges of Predicting the Future

4:21 to 6:26

Discussion on the difficulties of accurate future predictions.

“One, historically, we are very bad at predicting the future.”

Evolving Perspectives on Work and Certainty

6:26 to 7:04

The changing nature of career certainty over generations.

“What's really interesting about the cross-section of both of these books is that for much of our lives, career meant certainty.”

The Importance of Admitting Uncertainty

7:04 to 9:00

How acknowledging what we don't know increases credibility.

“challenging for a lot of members of our audience.”

The Dangers of Chasing Certainty

9:00 to 11:08

Exploring how the pursuit of certainty can hinder personal growth.

“So we're also wiring ourselves to chase that certainty with more information.”

Reddit Responses and Relationship Advice

13:54 to 14:24

Analyzing shifts in relationship advice trends on Reddit and LLMs.

“When you need the right person to cut through the chaos, this is a job for Indeed Sponsor Jobs.”

The Uncertainty Loop in Relationships

14:24 to 16:50

Discusses the trends in relationship advice and the role of uncertainty.

“We talked about this interesting review of Reddit responses and how it tied to LLM responses around relationships.”

The Year of Living Dangerously Experiment

16:50 to 22:49

Explores a couple's experiment with their relationship to tackle uncertainty.

“when I talk to people about it, I say, do you think they broke up or stayed together?”

Comfort Traps and Indecision

22:49 to 25:59

Analyzes the comfort trap in decision-making and its effects on personal growth.

“So how have you personally looked at this comfort trap?”
Show all 22 chapters

Making the Right Decisions

27:40 to 28:00

Discusses the nature of decisions and how to make them right.

“And Johnny, our co-host, his dad shared this with us.”

Understanding Decision Making

28:00 to 29:28

Explore how making decisions isn't about right or wrong but about the actions taken after.

“We double down on the decision and we move forward on it.”

Differentiating Decision Types

29:28 to 30:54

Learn the distinction between one-way and two-way door decisions and their implications.

“If you make a mistake, you can probably come back.”

The Comfort of Information Consumption

30:54 to 32:58

Understand how excessive information consumption can hinder decision-making and action.

“And a lot of these decisions are much less set in stone, much less final than we tend to assume.”

Acceptance in Uncertainty

32:58 to 34:46

Discover the importance of accepting what we cannot control and how it influences our lives.

“And I think the other thing that like these information loops do is they give us a sense of control.”

Taking Action Amidst Anxiety

34:46 to 36:50

Learn how action can mitigate anxiety and lead to greater clarity in uncertain situations.

“I think this is like real foundational, you know, wisdom for living is, you know, think about something like climate change.”

Growth Through Uncertainty

40:50 to 42:00

Explore how embracing uncertainty can foster personal growth and decision-making.

“With Red Bull Summer All Day Play, you choose a playlist that fits your summer vibe the best.”

Navigating Indecision: The Three Key Questions

42:00 to 46:00

Learn about three essential questions that help clarify decision-making during indecisiveness.

“And then I had all this like crippling doubt the moment after I said yes.”

Rewriting Your Narrative: Embracing Uncertainty

46:00 to 51:20

Discover how to recast life decisions into empowering narratives that reflect your values.

“Because the truth is, you're never going to know exactly what outcome you're going to get before you make the choice.”

Practical Strategies for Managing Uncertainty

51:20 to 56:01

Explore actionable steps to handle fear and uncertainty effectively in life.

“And part of what it means to be human or to build your tolerance to uncertainty is to continually wrestle with these different inclinations that we have.”

Trusting Your Future Self

56:01 to 59:08

Learn how to cultivate trust in your future self when facing uncertain decisions.

“That curiosity piece can feel like a trap going back to the information and the seeking of information, where we often find ourselves in hard decisions and we think, well, maybe there's an imbalance of information here.”

Promoting Future Resilience

59:09 to 1:00:15

Explore the importance of resilience in managing life's uncertainties and challenges.

“And I think so many of our audience members can relate to that because they are high achievers, they are self-improvement junkies, and they look at themselves where they are today and how far they've come.”
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Transcript

Automatic transcript. May contain errors.

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2:23Welcome back to the show. Today we're talking with Simone Stolzoff, journalist and author of How to Not Know. Simone spent three years studying how we handle uncertainty in careers and life. He shares why experts predict the future as well as darts throwing chimps, how chasing information robs you of actual wisdom, and why trusting your future self matters more than having all the answers today. Uncertainty is not just a threat. Simone shares the three traps that we all face when it comes to managing uncertainty. Welcome to the show. It's great to have you. Thank you. It's a pleasure to be here again.

2:57Last time we were talking, it was about finding the good enough job. And I think many of us are now feeling that that might not even be enough with the rise of AI, a lot of self-doubt, a lot of uncertainty in our career and what the future will look like. So how should we be thinking about that now versus when you wrote it? And what have your thoughts changed now with this new book around uncertainty? Well, if I had all the answers, I definitely would not be a journalist. I think one of the benefits of being a reporter is that I have these questions myself. The cliche is that you write the book that you need to read.

3:34And so my first book is about work and identity and how work has come to be so central to Americans' identities. And then I go out into the world and talk to people about it. And they'd say some version of, oh, that sounds great. How should I think about the future of my career with all of these generational technologies that are potentially undermining my entire industry? And some days I want to just throw up my hand and say, I don't know, I was a poetry major for God's sakes. But others, I was like, okay, this question of how do we get better at dealing with uncertainty is germane to our careers, but it's also relevant to the world at large to our personal lives.

4:09And so the last three years has really been my exploration, not as sort of an answer to the AI question, but the AI question as a catalyst to think more broadly about how do we get better at dealing with what we don't know. And so I think the biggest thing that I'll say about AI, and I'm by no means an expert, is that in these moments of transition, I think we have a really natural tendency to pull to the extremes, to either lionize the technology and say, you know, AI is going to usher us into this age of unprecedented creative expression and automate all of the rote boring tasks, or to villainize the technology and say, it's inevitable, we are going to be in a moment of class warfare, where the robots show up with pink slips, and we're not going to know what to do with our society.

4:57And I'll say two things to that. One, historically, we are very bad at predicting the future. So there's this researcher named Phil Tetlock. He collated a decade's worth of predictions from the smartest people in the world, the economists, the journalists, politicians, et cetera. And he found that the average expert was roughly as accurate as a dart-throwing chimpanzee. So if you even think about the people who are paid to do this professionally, to forecast and predict the future. We're very bad at those predictions. And the second thing is we're really bad at predicting how future events will make us feel.

5:38So even if we knew exactly what the future would hold, we're bad at determining what's called effective forecasting. So how we respond or react to those future events. So the canonical examples here are like people that get left at the altar or people who win the lottery or people become paraplegic. We think it will either sort of send us into a utopia or send us into a dystopia, be the end of our lives. We all have a friend probably who's gone through a breakup and said, oh my God, my life is over. And then you talk to them six months later and they're like, this is the best thing that's ever happened to us.

6:13So my sort of advice in this moment of transition is to reserve our judgment about how exactly these future events will affect us and have the humility and understand we don't actually know exactly what the future will hold. What's really interesting about the cross-section of both of these books is that for much of our lives, career meant certainty. So when we think about our parents, we think about our grandparents, there was a lot of certainty tied to get the credentials, get the job, stick with the company, work your way up the ladder. That's now changed quite a bit under our lifetime. And then on top of that, many of us work in an area of knowledge work where we have to have a level of certainty in our deliverables.

6:53What we're sharing, what we're delivering to the company, what we're working on requires a level of certainty in our own judgment and our work product. And I think both of those unraveling at the same time has been really challenging for a lot of members of our audience. Yeah. I mean, I think the thing with the second point about certainty in our products is I think there is this assumption that when we have higher levels of certainty, when we have lots of conviction, we are more credible or more trustworthy. But one interesting study that I looked at for the book found basically the opposite to be true, which is to say that when we are better at admitting what we don't know, that's actually what breeds more credibility.

7:37And some of the smartest people I've ever met are the same people that say, I don't know the most and have a real clear sense of, okay, this is like the realm that I do have expertise that I know. This is what I don't know. And I can distinguish between the two. And so in a business context, for example, for a knowledge worker, I think the most sort of productive and helpful employees are the ones that have a clear sense of what is the difference between, say, a fact and a hypothesis. And for the hypotheses, how can you run experiments to figure out what it is that you actually know, as opposed to maybe what we'd think of like the canonical example of the CEO that says, this is exactly what the next 10 years of the economy is going to look like, and this is how we're going to win.

8:24Having that level of humility actually makes you more open to the truth as it emerges. With that, I think many of us try to manage uncertainty with more information. And AI has made that even more available where we can just ask chat, hey, what do I do with this uncertainty in my life? And we feel good with the way that it confirms or changes our perspective so that we feel like we're driving towards a level of certainty, even in these moments like me as a new parent asking chat a lot of questions about, hey, how do I be a great dad? Or what do I do with the situation? My daughter's not sleeping.

8:57Chat rewards that with a level of certainty in its response. So we're also wiring ourselves to chase that certainty with more information. It's a trend that is an accelerant of something that was already going on, which is the rise of the internet and the mobile phones have created the expectation that answers should be readily available. I think there's two problems. One is that not all questions deserve a certain response from an LLM or a Google search. You can't say, you know, chat GPT, what should I do? Who should I marry? Et cetera. But we have this expectation that answers should be readily available.

9:36And the second thing it does is it robs us of the practice of sitting with what we don't know. There is a wisdom in not rushing to certainty, not grasping for that definitive answer and actually having to wrestle with the question to figure it out. I think this is very true in sort of a knowledge work thinking context. There was this great study from MIT recently where it had all of these students write essays and some were assisted by AI and some weren't. And basically the AI assisted essays, the students didn't remember anything that they wrote, even though it was still their product. And so it begs the question, why do we write or why do we think?

10:17And if the answer is to wrestle with ideas and come to your own understanding, just outsourcing that decision making to a chatbot or to technology will not actually help you grow. There's this metaphor that I really like that I read in The Atlantic recently, which I think is a physicist. Using AI to solve really hard problems is like taking a helicopter to the end of a hike. You might get there faster, but you miss out on all the reasons that makes the hike worth doing. Now, I'm not like a Luddite. I don't want to say you shouldn't use these tools at all. But if you think about outsourcing all of our questions to a chatbot, for example, at scale, what does that do to our own capacity to sit with the unknowns that are not necessarily solvable?

11:08Big questions like, how should I think about my mortality? Or what should I do about climate change? Or how can I make peace with geopolitics in the world that feel like they're not resolving? It can actually lead to a lot more anxiety and stress than the sort of wisdom of being able to not necessarily need to have certainty right away. Johnny, I've been wearing my quince linen shorts on repeat. I took them to the park over the weekend. They're lightweight, breathable, and the colors are so sharp. I always get a compliment. That's the thing about Quince. You look put together without even thinking about it.

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14:24We talked about this interesting review of Reddit responses and how it tied to LLM responses around relationships. And many of us were going to Reddit asking, should I stay with this person? Do I need to break up with them? Looking for certainty. Is this the right person for me? And they saw a trend over the last 15 years that those responses turned more negative. Like remove yourself from the situation, break up with the person. And wrestling with that uncertainty was not the predicted response then from LLMs. since llms are trained on a lot of reddit responses we're also now getting relationship advice that is the certainty of break up with them leave them where relationships do contain a lot of uncertainty that's a part of being in a partnered relationship with someone especially over your life there's going to be situations where it feels certain there's going to be situations where it feels uncertain but unfortunately even the way we're training these llms is to remove uncertainty in our responses.

15:22And therefore we're creating a feedback loop as we're chasing certainty in our lives. The story that I opened the book with is about a couple who had been together for 17 years, married for 10, and they were out having a drink at a bar in New York. And they were talking about their relationship. And both of them sort of knew that something wasn't quite right with the relationship, but they weren't sure what to do about it. And so they did something that others might see it as crazy. They said, okay, we're going to run an experiment. We're going to call it the year of living dangerously. And for a year, we're going to go our separate ways.

15:58And then we're going to come back to this bar exactly a year from today and determine whether or not we want to stay together. And it's sort of like stranger than fiction, you know, faster than a case study. And I won't spoil the ending for you. But what I think is interesting about the experiment is like normally in those situations, we would maybe go to our best friend or go to our chat bot and say, like, should we break up or stay together? And then you pull to one of those. Like you say, okay, I'm just going to grit my teeth and bear it and I'm going to carry on. Or like, I'm going to break up.

16:30That's the only option. But what I think this year of living dangerously does is it creates sort of a third door where it's like, okay, we're going to prototype what it might be like to break up. And then we're going to marinate in that uncertainty for an entire year and then come back together and determine whether we want to stay together or not. And even in sort of like my informal poll, when I talk to people about it, I say, do you think they broke up or stayed together? It's about 50-50. Like half the people are like, it's a Hallmark movie. It's the Pina Colada song. Of course, they came back together and they remembered their love.

17:04And then the other half is like, oh no, there's no way that they got back together after spending like a year of giving their energy outside of the relationship. But I think it comes back to that question of asking chatbots for advice, one thing that uncertainty does is it makes us uncomfortable by design. And part of what we do sometimes to resolve that uncertainty is try to get to the sort of safest option or get out as quickly as we can. One psychologist that I talked to said, you either try and gather as much information as possible or you become incredibly impulsive. You probably know intuitively which one you are.

17:43Like if you're going to like buy a pair of jeans, are you the person that like tries to try on every single pair of jeans in the store? Or it's just like, uh, I'll take the one in the window, you know? And like, neither of those are necessarily adaptive responses. Like maybe you should try on like three pairs of jeans and determine what you like and then make a pick. But I think we all have the friend that's either like talking to everyone they can about their relationship and like their Uber driver and their yoga teacher. And like, you know, what should I do? What should I do? What should I do without like doing the introspective work of like trying to get clear themselves?

18:13And then we have the other friend who like anytime something, there's any tension or struggle or whatever, they automatically just leave town. And I think those are both responses that under the surface come from an intolerance of uncertainty. They come from a place of, oh, I'm feeling uncomfortable. I need to get out of this place as quickly as possible. We got to break up or I've got to like feel certain that I'm going to stay in this relationship forever. I love that the book breaks it down in traps so that we can start to intellectualize how we're actually managing this uncertainty in our life.

18:44And you touched on the first one, which is just comfort and how much we seek comfort through this uncertainty, whether it's racing to Reddit to get an answer about something in your life, asking everyone you know, or talking to an LLM. Part of it is seeking comfort in finding, well, what is that correct answer for me? There's a good job analog here where we all probably have a friend who is in a job that they know isn't right for them. But they'd rather sort of the devil they know than have to actually explore what it would mean to leave the job. And that's the trap of comfort. Comfort says, you know, stay where you know it's safe.

19:23You don't need to make any changes. But the problem is that all sort of learning and growth happens at the edge of our comfort zone. And modern society makes it really easy to never have to leave our comfort zone. We can just stay in our sort of climate controlled rooms and get delivery service and not have to interact with other humans. But I think this whole trend of sort of friction maxing or finding ways to create a little bit of that rub in your life is a pushback to a life that feels too comfortable. And one of the benefits of getting better at tolerating uncertainty is you get to discover all the possibilities that sit outside of your comfort zone.

20:04If we just stay in our comfort zone, our sort of muscles to be more resilient, start to atrophy. And so it's by exposing ourselves to that novelty, exposing ourselves to that uncertainty, striking up that conversation with a stranger, even though you're not sure how it's going to turn out, going to that new restaurant that you maybe have walked by a million times but never have actually gone in, ordering that thing on the menu that maybe you don't normally order. Those are the ways you actually figure out what it is that you like and help yourself grow. And so that's sort of the first trap, right?

20:38It's like if we just stay comfortable and never expose ourselves to uncertain situation, we can be in sort of a prison of our own preferences. Especially for many of our clients, one of the issues that they have is catastrophizing. So the thought of the opposite of leaving that person, leaving their job is, well, I'm never going to find anyone again. I'm going to be homeless. I'm going to be destitute. there's no jobs available so I can't possibly do that and that that catastrophizing drives them back towards comfort and when you actually look back on your past in those moments where you catastrophized and what was the outcome it's never anywhere close to what our mind is capable of catastrophizing around and the other thing that it does is it just reinforces this false notion that you know the worst case scenario will always happen because like if you never put it to the test.

21:30If you never actually go out into the world and transact, then you never get the data to undermine that sort of limiting belief that you have. And that's one of the big things that I learned from a lot of the psychologists that I talked to for the book, is that we need sort of uncertainty exposure therapy. Like when you expose yourself to uncertain situations, it makes it easier for you to deal with uncertain situations moving forward. And so the person who is always sort of stuck in this like lukewarm existence or this job or this relationship that they know isn't working but are too fearful of leaving, it becomes this vicious cycle where they don't leave and so it becomes a bigger burden.

22:14They get less good at being able to deal with uncertainty and therefore they get continually stuck in the situation that they're currently in. But if you're able to expose yourself to uncertainty, even either proactively or retroactively, just thinking back to times in your life where you've been in uncertain moments, maybe you did get laid off or maybe you did get broken up with, and remember that you have the tools and the skills to be able to come out the other side. That is the confidence and the conviction that you'll need in order to be able to deal with the uncertainty in the future. So how have you personally looked at this comfort trap?

22:52Because I feel like we all have areas of our life where it is premonent. One of the inciting incidents for the book for me was, so I was working as a magazine reporter and I had a recruiter reach out to me from this design firm called Idea. And I was sent through like this existential loop. Like I couldn't make up my mind for the life of me, what job I wanted to take. And, you know, on one hand, it's like, oh, what was me? The agony of deciding between two attractive job offers. Like here's like the world's smallest violin. But on the other hand, it was like, I thought that my job was my identity.

23:28And the decision about whether to be Simone, the journalist or Simone, the designer was existential in nature. And I just like flip flopped every day, like I couldn't make up my mind, I'd make up my mind. And then I'd like wake up on the other side of the bed, or I'd have a conversation with someone and say, Oh, I'm completely wrong, I go to the other extreme. And what I realized is that two things. One is I was looking for certainty in a situation where there was no certainty to be found. Like, how could I know which job was like the perfect job or which job was the right job for me until I'd actually like done the job?

24:03And I think people often get caught in this trap when it comes to dating of like, is this worth my time? Should I actually go on this date? Whatever. You don't know until you've actually transacted and you've actually been able to get the data from your lived experience. And the second thing is that my ambivalence, this sort of like ruminative cycle that I was in, was its own form of comfort. I was comfortable in the indecision. And the minute I had to actually make a choice would mean some sort of foreclosure of the other options that exist out there, which felt like a huge loss. you know typical like loss aversion behavioral economics losing something feels worse than gaining something feels good and so by staying in this sort of indecisive mind space i was actually pursuing comfort even though it felt so distressing for me this is sort of my like auto self you know psychology analysis of my 29 year old or whatever i was back then But I think like in many ways, I wrote the book for that version of me who was so uncomfortable with uncertainty that I couldn't make any decisions.

25:19And I was convinced that if I just banged my head against the wall at the right angle, this like clarity and certainty will emerge without acknowledging that to make decisions, to be a human being is to get to an uncertain place and still be able to make decisions and persist nonetheless. less. And, you know, uncertainty is uncomfortable, yes, but it's also an inevitable part of what it means to be a human being. And unless we can make decisions and make commitments, not in the absence of uncertainty, but in spite of uncertainty, in spite of our doubts, that's what it means to actually be a human being continuing to grow and progress.

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27:20Who you wish for. Obsession is 96 % fresh on Rotten Tomatoes. I love you so, so, so, so much. It's blood-soaked nightmare fuel. What kind of sponge you put on her? You have been warned. Obsession. Rated R. Under 17 on a minute without parent. Only in theaters May 15th. With special engagements in Dolby. And we share this with our clients. And Johnny, our co-host, his dad shared this with us. Basically, there's no right or wrong decisions. There's just decisions you make right. And we often don't think about the effort that went into those right decisions in our past. And all the ways that it ended up working out.

27:56Because we applied ourselves. We fought through the discomfort. for it. We double down on the decision and we move forward on it. And there's so many of those decision points in our life that if we look back, we go, well, they weren't right or wrong. We made it right. It was our actions after making the decision that made it the right fit for us. And it's very similar in your career. You will make the right decision for that next step. And then when you land that role, you will lean in and all the ways that turn that into the right decision for you. And in the very worst scenario, like you make a decision, you realize it's the wrong path.

28:27And that's an incredible lesson. You know, I think there's this philosopher that I talked to in the book who said something very similar. She said, what makes a hard decision hard is not that one option is clearly better and the other option is clearly worse. And you're just like too stupid to figure it out. What makes a hard decision hard is one option is better for some reasons. Another option is better for other reasons. And neither option is better overall. all. And so, you know, if that weren't the case, it'd be an easy decision. So when we're in these hard decisions, it's really just about what trade-offs are you willing to accept in this moment?

29:04And then how can you spend your energy retroactively convincing yourself that you made the right decision, trying to make the most of the decision that you made? And if you really understand that you made a bad decision, course correcting. You know, Jeff Bezos has this distinction between one-way door and two-way door decisions that I think is really helpful, which is the majority of our life, the decisions we make are two-way door decisions, which is to say you walk through them. If you make a mistake, you can probably come back. These are decisions like what to do in our career, whether to go on a date, whether to eat the pasta or the pizza, whatever.

29:39One-way door decisions, they're few and far between. They're decisions like, should I buy this house? Should I marry this person? They're much harder to reverse. But the problem is we take our one-way door decision analytical process and framework and use them for two-way door decisions that actually matter far less than we think. And so part of my goal for this book, and so far as it relates to decision making, is to help people understand where they can lower the stakes and actually move a little bit more quickly in their decision making. this isn't to say that they should just like flip a coin necessarily but when you're choosing between a hard two-way door decision it's hard because they are trade-offs that you have to be willing to accept and it's just a matter of like which trade-offs are you willing to put up with like i think about this in careers all the time like sure if you work in finance you can make a lot of money but like there are really long hours and it might not be particularly meaningful If you work in the nonprofit sector, maybe you can make a big impact and it can be really fulfilling, but maybe you'll be stressed about how much money you'll make, etc.

30:51Like you can do that ad infinitum. And the question is, what tradeoffs are you willing to accept at this season of your life? And a lot of these decisions are much less set in stone, much less final than we tend to assume. What goes along with that, unfortunately, is consumption of information and optimization feels better than facing the tradeoff and dealing with the tradeoff. So many of us will sit in that rumination and optimization phase and say we're experimenting, but we're really just consuming before actually taking any action. weighing should I eat this food or do this diet or change this workout routine instead of actually just going to the gym and doing the thing that will prove out the experiment many in our audience many of our clients will sit in the information loop consuming consuming consuming to avoid the trade-off and avoid the decision ultimately yeah I mean it's a comfort thing right like it's there's got to be like a German word or something for rather than doing the thing like consuming information about doing the thing.

31:54I noticed this in myself. The other day, I was feeling really addicted to my phone. And rather than just put my phone down or try and touch grass or whatever, I read an entire book about phone addiction. And I think probably a lot of listeners to the show, maybe you have always had this dream to start a company. But instead of actually taking the first steps and start the company, you just listen to a lot of podcasts about entrepreneurship or the same about dating, what have you. And I think it's exactly what you said. You stay in this sort of information consumptive space, which is safe and comfortable, but doesn't actually get you closer to your goal.

32:32Unfortunately, life is full of trade-offs and we're going to have to wrestle with them. A life avoiding trade-offs, a life avoiding uncertainty is not a life well-lived. But in this information age, it just feels really good to consume those empty calories of another short form reel about iPhone addiction or another short form reel about what I should be doing in the gym to get a six pack.

32:59And I think the other thing that like these information loops do is they give us a sense of control. Like, yes, like if I just read about sleep training babies, then I feel like I can be like the master of this universe of like information gathering about parenting or same with the gym or entrepreneurship. But the problem is there's lots in our life that we can't control. And even if you read all of the books about sleep training, and even if you, you know, take a course and, you know, pay$19.95 to have a coach in your pocket every day, there's a difference between that sort of consumptive layer and what I'd call like the transactional layer or like the action layer of actually being in the world.

33:48And one of the other traps that keeps us in this hell-bent grasp for certainty is the assumption that we can control how the future goes or we can plan everything. And therefore, we don't have to like accept that anything is out of our control. and there's no better practice than parenting to this i think at least yeah i also have a young kid at home and there just isn't always a direct relationship between your effort and the outcome and you know it's just this great microcosm for learning about the value of acceptance you know and i think that is sort of on the other side of the desire to control is the desire to be able to accept what we can't control.

34:35And I think a lot about the serenity prayer that's used often in addiction circles of, you know, God grant me the serenity to understand the things that I can control, the things that I can't, and the wisdom to know the difference. I think this is like real foundational, you know, wisdom for living is, you know, think about something like climate change. It might be causing you so much anxiety to think about like the future of the planet. But the thing that will help with your anxiety is actually the same thing that will help make a difference with climate change, which is taking some sort of action.

35:11And, you know, I think of this line sort of action absorbs anxiety. Like as you take action, the clarity begins to emerge. That's the thing that actually will help you get more certainty and less uncertainty. but when we're anxious it can be paralyzing and that's sort of my favorite definition of uncertainty is like a sense of doubt that keeps you from taking action or keeps you from making progress and so that's the people just take away one piece of wisdom from the book it's that you know action is the process through which you can gain more certainty it's not gathering information it's not you know thinking really hard it's actually going out into the world and trying things.

35:55For me, coming out of COVID, this was probably the biggest lesson around my own dealing with uncertainty was this control trap. And I'm thankful that my partner and I will call it out in each other now. Like, is this something that we can control? And, you know, I'm falling into a very similar loop with AI of like learning everything I can about it, just like I was trying to learn everything I can about the different variants and how it's hitting different places in the world and the vaccines and everything that I could consume in a hope of trying to get some control back in my life as I was going through the pandemic.

36:25And now it feels very similar with AI. Like you could spend all day long learning about the models and how things are changing and what could possibly happen. And I'll come out of that and I'll share something with my wife. And she's like, well, what are we going to do about it? Can we control this? Like, is there some meaningful action we can take with this information? Or are you allowing it to just create this steady state of anxiety in you that's leading you to try to consume more information? Like what's the action that we can take for me has helped quite a bit to like, okay, there are things that I can control and I can take action around.

36:57And there are things that I cannot control that I don't really think doing more reading or seeking more information is one of those areas that I should be focusing on in this area that I can't control. I love that. Yeah. When I think about sort of like taking action in spite of uncertainty, I think sometimes about a decision tree. And the first question is, do you have the ability to influence the outcome? So, for example, imagine you are a senior in high school and you are really anxious and unsure about where you're going to go to college. If you're in a place where you can influence the outcome, say, like, you haven't submitted your applications yet or, like, you have the ability to, like, try and get good grades a semester, like, do that thing.

37:41Like, if you have the ability to change the potential outcome, like, try and write the best application you can, et cetera. But then if the answer is no, you kind of drop to one level deeper in the decision tree. And the question is, can you prepare for different potential outcomes? So this is what's often called contingency planning. And rather than just thinking about sort of one fixed future of exactly how you want things to go, can you think of like different potential futures? And maybe going back to this example, like if you got into that dream Ivy League school, do you know how you would pay for it?

38:15If you didn't get into that dream Ivy League school, do you have a good sense of like how you might be able to design a major at the backup school? if you don't get into any of the schools that you want to get into do you have like a plan for how you might deal with that situation and by doing some of that contingency planning it does two things one is it helps you find some agency so like take a little bit of control back from the universe and the second thing it does is it helps you feel prepared for these multiple potential scenarios so you don't feel blindsided and then if you've done everything that you can to plan for different scenarios and you can't do anything to control the outcome, that's when it just comes down to acceptance.

38:56And there are things that we can do, especially in like an acute sense. So one of the studies I read about in the book is breast cancer patients. And often breast cancer patients find the hardest part of the entire process of their breast cancer journey, the time between when they get a biopsy before they get their diagnosis, that waiting period. And it's harder than chemo or any of the surgery, et cetera. It's that uncertainty about whether or not they have this potentially terminal disease. And if you're in that waiting period, you can do things like plan for different situations. You can look for silver linings and potential bad outcomes.

39:34But really, at the end of the day, it just comes back to regulating your nervous system. How can you get to a place where you can be grounded through the uncertainty. And maybe that's something like breathwork or meditation. Maybe that's something like just an acceptance of the uncontrollability of the universe. But once you can accept the things that you can't control, you get out of that place of denial and it actually shrinks that anxiety. You might still have some worry. You might still have some anxiety. But if you're not trying to control things that you can't control. It helps right size that worry that you might be feeling.

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41:39the judgment. You cannot control them. You can think and hope and strategize around. But oftentimes when that then happens, our clients will find themselves pulling back. It's like, oh, I can't control that. So I'm not going to lean in. When in actuality, that is like the most important is to lean in in those moments where you can't control the other side, because that's where all the learning and growth actually happens. And if we allow our inability to control something to lead to us to again to be indecisive or not take action we're surrendering to that uncertainty those moments are incredible opportunities for us to refine our character which is to say to make decisions based on the type of people that we want to be and you know i'm thinking about that sort of clear indecision moment for myself like ultimately i said yes to the design firm.

42:31And then I had all this like crippling doubt the moment after I said yes. But what helped me sort of persist is I said, I want to be like someone of my word. And I said yes. And therefore, even if this is like the wrong job for me, I still want to be the type of person that is like good to what he says he's going to do. And therefore I'm going to make that choice. and it's like i spoke to an ethicist for the book about these sorts of decisions and he always advises yeah he always has the same three questions to people that he's counseling the first is what do you want to do which hopefully gets into that sort of more embodied sort of gut feeling as opposed to just being in your mind do you want to want to do that which taps into what's often called like our second order desires, like our higher level thinking, which is like reflecting on that.

43:32And so maybe you want to smoke a cigarette, but you don't want to want to smoke a cigarette. It gives you a little bit of psychological distance. Or maybe people in your life want you to do that, but you don't actually want to do that. And I find that a lot in career where our family and loved ones want us to do something because they feel that there's uncertainty in that path. And I faced that in my own career of like following along what would be certain for them and create safety for them, knowing that I got an advanced degree and I got a professional career. And then I was faced with the decision and I went with my gut in that decision.

44:05And 20 years later, you know, clients will ask me, well, how did you make that decision? Because I find myself ruminating and I find myself in indecision. And I was like, well, in that moment, I was able to tap into my intuition and it worked. In other moments, I've been faced with uncertainty and I've ruminated as well. But I think that want to want is such a key question because oftentimes we'll realize that societal pressures, family pressures are driving us in a direction that's not what we really want to want. Yeah, exactly. Like whose narrative is this? Whose voice is this in my head if not my own?

44:37And then the third question he always asks is, what does this choice say about you as a person? and so connecting that choice to like your values your identity and i think that is like such an eye-opening question often because like if i were to like say yes to the design job and then like renege and go back to the journalism job you can spin up many different stories about what that means but like i think the story that i would tell myself in that moment is like you are you know and consistent. You're not trustworthy. You're flip-flopping versus like taking the job, even if it isn't going to work out or it's like the worst decision I've ever made would say, you know, I'm a person of integrity.

45:22I have follow through. I'm willing to like turn towards uncertainty and see how they turn out. And I think especially for people that are in higher stakes situations, like, you know, asking someone out on a date or something like that. well who is the type of person that you want to be like do you want to be the person who like makes the ask or like goes on that date or do you want to be the person that is so crippled by uncertainty that you never actually transact you never actually enter the arena so to speak and i really like that sort of like three question framework for coming to a decision in these moments of indecision?

46:02Because the truth is, you're never going to know exactly what outcome you're going to get before you make the choice. The key is getting to a place where you can choose. The third question for me really strikes a chord because it's that part of the narrative writing that we do actually have control over. And we were joking a little bit before we started about writing a book and how the process is and how you go in with an idea and you test it out and you work with your editor and you're rewriting sections, maybe even full chapters of the book. That when you first wrote it, you thought, Eureka, this is it or this is perfect.

46:35But we have that control in our narrative at any point in our life to rewrite that decision, to rewrite what it ties to our new values as or what the lesson is that we got out of that decision that at the moment felt like it was out of our control or felt like the worst thing in the world. I can't believe that breakup. I'm never going to find anyone. we have the power to grab the pen and rewrite that narrative now to be like no that was actually the perfect thing that i needed in that moment to find this other career path or to meet someone new or to really challenge myself in ways that i hadn't while i was in that relationship so then the question basically becomes like what is a decision that you can stand by even if you don't get the outcome that you desire you know like how can you make decisions that are from a place of your values or from a place of the aspirational person that you want to be and let that drive you and not let the result of the decision determine the quality of the decision.

47:31Let the decision be what it is and then you get the outcome and then you can readjust from there. Yeah. One of the exercises we do with our X Factor accelerator members is that self-authorship of looking back at these moments in your life and recataloging them and rewriting the narrative around them because sometimes we will hold on to past stories or past versions of ourself that in that moment felt like us and were emotionally maybe impactful in a positive or negative way and if we actually do some introspection and look back now where we are in our life we can grab the pen and change the narrative and rewrite it as like no actually that was a key decision of me living to this value of being adventurous or being outgoing that i didn't realize it in the moment and I hadn't written the narrative in that moment around that exact value.

48:19And that kind of brings us to the third trap, the third sort of thing that I bring up in the book that keeps us from being able to tolerate uncertainty, which is hubris, which is our own assumption that we know best. And I think one thing that I really like about this sort of rewriting the narrative exercise is it trades some of that hubris for humility. And rather than thinking like I am the master of the universe I know what's best like I know it all I don't need to open my mind to new information it says like okay this is like the narrative I'm writing today but I'm gonna proceed with full knowledge that I can always rewrite that narrative that I can trade the sense that I know exactly what's best for me or I know exactly how the world works for a sense of open-mindedness that I can be able to assess new information as it presents itself.

49:15And that's really, I think, the benefit of developing more tolerance of uncertainty, is rather than approaching your life or the world through a fixed mentality where you're closing your mind to new information, when you're more tolerant of uncertainty, you can open your mind to the world as it emerges. And I think that's sort of the problem that I see in so much of society these days, where our desire to find certainty, to find the guru that'll tell us exactly when the market will crash or how the relationship will end or who's going to win the election, what have you. All of that certainty is actually a narrowing function.

49:57And once you are certain, you don't need to gather more information. But if you're able to maintain that space of not knowing, that space of humility, that's when you can actually see all of the possibilities that are opening up in front of you. Yeah. What struck me about the three traps as I went through the book was how those different traps hit me at different points in my life and what it meant in my 20s where hubris was really a driving force. I was comfortable with discomfort, going to college, moving away, all this change in upheaval in your life when you're younger and you're not as set in your ways.

50:36You don't have as many of these wired patterns in your brain to deal with. But that hubris of like, I know what's best often led to me falling to that trap. And now as a parent, I see control is like the trap that I'm really finding myself wrestling with as I crave safety for my daughter. And I really want to handle the uncertainty of this changing, evolving world that we're facing, especially now as parents thinking about school and what the job workforce will look like in the future. That's really the trap that I'm wrestling with. And I think what's interesting about thinking about these three traps is it allows you to navigate through it depending on where you are in your life and what those values orient around?

51:15As I mentioned earlier, I wrote the book that I needed to read. I think this is something that is never something that you fully have figured out. And part of what it means to be human or to build your tolerance to uncertainty is to continually wrestle with these different inclinations that we have. The reason why there are traps is because they're really easy to fall into. And so one metaphor that I like thinking about is to be a leader in this world is like being on a rowboat in a lake that is shrouded in really heavy fog. You might not be able to see very far in front of you, or you might not be able to know exactly where you'll end up, but you have two jobs.

52:03One is to maintain faith that you'll eventually reach land. Remember, you're in a lake. And the second is to keep rowing. And I think that's the key, you know, is to not let the uncertainty, not let your fear prevent you from continuing to take one step at a time. And that's really what I hope people take away from the book is how can you find a way to continue to take action in spite of uncertainty rather than waiting for this moment of perfect clarity or perfect certainty before you act. So for those in the audience right now who feel like they've been rowing the boat, but they're overwhelmed with fear, are there some practical exercises that we can share with them to manage that fear to keep rowing?

52:53It sort of depends a little bit on whether we're talking about like acute uncertainty. So a piece of information that will one day be revealed versus more ambient uncertainty, like the uncertainty of when I'm going to die or when this war overseas is going to resolve. But a few things that I keep in mind. One, I always start with trying to separate what we can and what we can't control and really give your energy to the realm of things that you can't control. The second is just to focus on one next right action at a time. There's this concept from Buddhism that I really like, which is, some version of the journey of a thousand miles start to the single step.

53:37Part of what's so hard about these moments of uncertainty when it feels like you're rowing the boat and you can't know exactly where you're going to end up is that we have this natural tendency to catastrophize or think about all the things that will go wrong or to focus on the myriad different tasks that you need to accomplish before you reach whatever your sort of version of enlightenment is. But all of these paths start with just one stroke, one row at a time. Like there's this chapter in the book that I write about crisis management. And there's this image that's like really stayed in my mind since I learned about it.

54:13The woman that I profile gets brought in to companies at sort of their worst moments. And she had this client, they were a big manufacturing firm and there was a big accident in one of their factories and some of their employees had died. And so she shows up to this boardroom and there's all these executives and they're just freaking out like chickens with their head cut off. And she took this big piece of butcher paper and she rolled it out over the table in the boardroom. And she wrote down every single thing that needed to be done. We need to communicate with investors. We need to issue a press release.

54:46We need to talk to employees. We need to check the factory and make sure it's safe. We need to make a plan for how we're going to talk about this in the press, et cetera, and wrote all of the things down on the piece of paper and then asked sort of like, where do we begin? And that is sort of like the mental exercise that I often encourage people that are feeling really overwhelmed by this uncertainty to do is like, what is the first step and not have to worry about everything after that. And then the last one is just a mindset shift, which is to try to choose curiosity over fear. So often when we are in uncertain situations, we are only thinking about the threat that's posed from uncertainty, which makes sense.

55:30Biologically, if you think about our ancestors, if there was a noise in the bushes, you didn't know the source of that noise, that uncertainty is potentially lethal. And I think often we still feel that way in a sort of a fight or flight response when we approach uncertainty. But the other side of the coin is that uncertainty is also the birthplace of possibility. Without uncertainty, there would be no serendipity or surprise or magic. It is the uncertainty that gives our life texture. And so if you're able to see the uncertainty as a potential source of opportunity, you choose curiosity over fear, that's what will allow you ultimately to keep rowing, even in those moments where you're not sure exactly where you'll end up.

56:21That curiosity piece can feel like a trap going back to the information and the seeking of information, where we often find ourselves in hard decisions and we think, well, maybe there's an imbalance of information here. So making a hard parenting choice. Well, I just got to read every Reddit thread and I got to talk to Chad about it. And I got to weigh what all my friends who are parents who are further along did. When in actuality, the information doesn't change how hard the decision is. It's hard because both options are on par. Either path could work for you. Maybe there's one more piece of advice that I'll give, which is maybe a little more philosophical.

56:58I have this friend named Emily. And Emily is a therapist. She's sort of like a therapist to the stars. She advises CEOs and leaders on how to navigate change and uncertainty. But before she became this sort of star-powered mental health professional in her early 20s, her mom was given a potentially terminal diagnosis. And Emily was like 23, 24. For a week, she just spent by her mom's bedside day after day. And she was really struggling. She felt like she was on this roller coaster of anticipatory grief and fear. And one day, a friend, a family friend of theirs named Bill, who is an oncology doctor who has lots of experience dealing with people at the end of their life, came by and visited Emily and said, Emily, how are you doing?

57:46And Emily said, honestly, not great. I had no idea what I'll do if my mom dies. I'm not sure I'll be able to handle it. And Bill said, Emily, the version of yourself that will deal with that tragic event if or when it ever comes to pass will be born into existence in that moment. And that version of you will have more experience, more context, and will be better equipped to deal with that than the version of you today. You have to trust in your future self to be able to solve your future problems. And I love that line, trust your future self to be able to solve your future problems. In the moment of parenting, you may not know whether you're doing the right thing for your kid.

58:37You may not know whether this is the best approach. But if you're able to cultivate some of that self-trust and think of your future yourself as someone who is capable and someone who is resilient and someone who will have more context and information than you do today, then hopefully that will give you the encouragement you need to keep taking action, to keep focusing on what's in front of you, as opposed to letting the fear take over and paralyze you. I think it's so beautifully said. And I think so many of our audience members can relate to that because they are high achievers, they are self-improvement junkies, and they look at themselves where they are today and how far they've come.

59:23So if we bring that into the future, saying whatever decision I make, I will be able to handle in the future with that information or who I've developed into, it's just a much better way to manage that uncertainty, especially in moments that we're all going to face. Our own mortality, or family members' mortality. These are going to be challenging moments, but we can muster in those moments based on all of the work we've put in to get there. I kind of said it better myself. Well, thank you so much for joining us. Where can our audience find out about your latest book and your work? Yeah, well, the book's called How to Not Know, as you can see over my shoulder.

1:00:01You can check out howtonotknow.com. That's probably the best place to go, but anywhere books are sold. and I can't wait till you read it and develop a little bit more uncertainty tolerance for yourself. Thanks again for joining us. It's wonderful. Cheers.

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From the publisher

Most people think uncertainty is the problem. It’s not.
AJ sits down with journalist and author Simone Stolzoff to unpack why our obsession with certainty may actually be making us more anxious, avoidant, and stuck. From AI and career anxiety to relationships, decision-making, and control, Simone explains why experts are terrible at predicting the future — and why learning to tolerate uncertainty is one of the most important modern skills.
This episode explores the three traps people fall into when facing uncertainty: comfort, control, and hubris — and how taking action, instead of endlessly consuming information, is what actually creates clarity.

Chapters00:00 – Why we’re addicted to certainty08:00 – Experts predict the future like dart-throwing chimps16:00 – The comfort trap and avoiding uncertainty24:00 – Why overthinking becomes emotional safety32:00 – Control, anxiety, and the illusion of certainty40:00 – Identity, values, and making hard decisions48:00 – Curiosity, future self-trust, and taking action

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Episode resources:

https://simonestolzoff.com

https://www.amazon.com/How-Not-Know-Uncertainty-Demands/dp/1324089458

Check in with AJ and Johnny!

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠AJ on LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Johnny on LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠AJ on Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Johnny on Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠The Art of Charm on Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠The Art of Charm on YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠The Art of Charm on TikTok⁠⁠

uncertainty, decision making, anxiety, overthinking, AI anxiety, career uncertainty, self trust, emotional resilience, control, mindset, personal growth, relationships, ambiguity, action taking, uncertainty tolerance

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