Financial Feminist - 285. Why You Stay Stuck in Jobs, Relationships, and Financial Patterns That Aren’t Working with Simone Stolzoff

Episode Date: May 12, 2026

Why do we stay in jobs, relationships, and financial patterns we know aren't working? Author and journalist Simone Stolzoff is back on the show to talk about his new book, How to Not Know — and the surprising answer has everything to do with our relationship with uncertainty. We're getting into the three certainty traps keeping you stuck, why more information is actually making your anxiety worse, the difference between one-way and two-way door decisions, and what it really takes to break the cycle when you can see the problem but can't seem to move. This is one of the most powerful conversations we've had on this show, and one you'll want to send to everyone you know. Simone’s links: How to Not Know: https://bookshop.org/a/90037/9781324089452 Learn the exact strategies to save money, pay off debt, improve your money mindset, increase your net worth, in The $100K Club. Get the details here: ⁠https://herfirst100k.com/ffpod⁠. 00:00 Intro  01:08 Why Uncertainty Feels Worse Than Bad News 03:14 Three Certainty Traps: Comfort, Hubris & Control 04:49 Why We Struggle to Admit We Were Wrong 05:36 Identity, Doubling Down & Changing Your Mind 10:23 Why Our Tolerance for Uncertainty Is Declining 14:28 More Information, More Anxiety 16:18 Escalating Commitment 16:52 Stop Loss Strategies & Rules-Based Decision Making 20:13 Outsourcing Your Willpower & Knowing Your "Enough" 28:08 Connie & Andrew's "Year of Living Dangerously" 30:21 How to Run Your Own Low-Stakes Life Experiment 35:16 One-Way Door vs. Two-Way Door Decisions 44:39 Ghost Ships: Making Peace with the Paths Not Taken 50:39 The Miscarriage, the Uncertainty & Finding Your Anchors 54:54 How to Not Know Learn more about your ad choices. Visit megaphone.fm/adchoices

We just got done recording today's episode. It was one of the most powerful conversations we've had on this show. And as you can tell, if you're watching on YouTube, this episode deeply moved me. And I think it'll deeply move you too. Today we are talking about uncertainty. And this is uncertainty that makes us deeply uncomfortable as humans. It's uncertainty about the worlds and politics and the economy. It's uncertainty about our relationships. It's uncertainty about not knowing if we are on the right path. Today's guest is a a repeat guest, and we loved him so much, we brought him back on the show. Simone Stolzoff is an author and journalist who has spent his career asking the questions no one wants to sit with. He's the author of two books, The Good Enough Job, which we talked about the first time he was on this show. It is the number one work-life balance bestseller that's been translated into over a dozen languages, but we're here to talk about his new book, How to Not Know. Right off the top, I will give you a content warning that we do discuss loss and miscarriage in this episode. But this is an episode you will want to listen to again and

again and send to people in your life to talk about too. All right, I've blubbered enough. Let's get into it. But first, a word from our sponsors. This podcast is sponsored by Squarespace. When my partner was launching his business last year, I was like, great, you need a Squarespace website. That was the first thing we did was sign up for Squarespace. And we signed up on Friday using my code. and by Monday he had a brand new website and was already making money. Yes, really. He used their cutting edge design tools to design a perfectly navigable website. That's a word.

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or domain. Okay, so I want to start us with a really interesting research study. People who had a 50% chance of getting a painful electric shock were more stressed than people who knew they were definitely going to get shocked. More stressed than the people who knew that the bad thing was coming. What does that tell us about why we stay in jobs, relationships, financial situations that we know aren't working just because leaving would mean not knowing what's coming next? A fascinating study, right? And Like I read it for the first time and was like, oh, I would totally be willing to roll the dice. And then I thought about it a little bit and I was like, wow, maybe the anxiety of having to deal with an ambiguity is actually worse than a certain bad thing happening. I think your question is spot on.

Like so many people, we all have a friend who's like in a relationship that they know isn't quite working for them, but would rather have the devil they know than have to deal with the ambiguity of knowing what life is like outside of it or in a job they know isn't working for them. but would rather just stick with that job than have to deal with the uncertainty of being back on the job market. And I think it points to just our natural wiring and our discomfort with uncertainty. Like, of course, you can think about this biologically. Like, when we were ancestors in the jungle and there was a rustling in the bushes, and you didn't know the source of that noise. Like, that uncertainty could be lethal. It could be life or death.

But the part that people don't appreciate is that uncertainty doesn't necessarily have to be a threat. it can also be the birthplace of possibility. There might be something waiting on the other side of that uncertainty that is better than what you could have ever imagined, not to mention if you already know that you're in a bad situation, it probably makes sense to get out. So if we're in a situation, like a relationship or a job, I find that when I talk to people who are unhappy, the justification starts, right? Like, they'll go, yeah, things aren't really working, but there's this good thing and this good

thing and this good thing, why do we feel the need to justify a situation that isn't working? Is it because that prevents us from having to actually do something about it? I think there's a few different ways to explain it. So in the book, I break down three different certainty traps. The first is comfort, our desire to stay comfortable. The second is hubris, our desire to think that we know best. And the third is control, our desire to plan out every single outcome of our future. And I think they all play into the situation where you have something that is like a known, not great outcome that you choose over a potentially uncertain outcome. On one hand, there's the comfort of what you already know. So you know this

relationship. It's why you might stay in the bad relationship or go back to your ex. There's something sort of reassuring about knowing. There's the hubris of feeling like you know best, like you can figure it out. And I think that's where a lot of the justification comes from. It's like, oh, it's not great right now, but he's having a really hard time at work. But I haven't been showing up as the best partner or this is just a phase, this is just a season, hopefully we'll come out of it. And then there's the control aspect of it, which is when you have to leave a relationship or leave a job that isn't working, it requires you to see some of that control over to an unknown outcome. Whereas if you feel like you're already in a situation that you can control, that you can know,

there might be comfort in that control. The problem is that it can be incredibly brittle to cling onto this sense of certainty, whether it is that not great job or that not great relationship, it might seem easier in the short term, but in the long term, there will probably be real consequences. So you mentioned the three certainty traps being comfort, hubris, control. Can we talk about hubris for a second? Because I imagine most women listening maybe don't have a lot of hubris, right? There's not a lot of toxic pride. But the way I see this show up for so many women is the like sunk cost thing where, oh, I've already put this much into this relationship or I've already put this much into this MLM or financial scam. Like I think about like index universal life insurance all the

time. Like that's a question I get. And I totally think it's a scam. I don't think it's worth your money. But people go, well, I already put 10K into it. And I think that's where the hubris can come in of I don't want to admit that I got conned or that, yeah, this relationship hasn't been working. So talk to me a little bit about that hesitancy to really get honest with ourselves? I'll bring up another study because I think it's illustrative of this point. So there's this researcher from Wharton named Katie Milkman and she looked at stock traders. So people whose job it is to predict whether a stock will go up or down. And what she wanted to look at is people who got their predictions wrong and whether they would update their predictions in the following court. And what she found is that when

you are wrong, but you're part of the consensus, so you're part of lots of people being wrong, it's easier for you to update your position in the next quarter and say, okay, I got this wrong, I'm going to try and course correct. But if you are part of the minority, if you're out on a limb with your prediction, people tended to double down on their wrong predictions. And I think it really comes back to people's identity. Like, you think about someone like a flat earther, and if they have this belief that the earth is flat, their identity is often wrapped up in that belief. And so changing their mind isn't just a matter of like updating their opinion based on new information. It's potentially undermining who they are. And I think that's where you get a lot of that

sunk cost fallacy of people saying, oh, if I admit that this is an MLM or I admit that this job that I chose or this partner that I chose isn't a good fit. Or the president I chose. Yeah, my own, idea of who I am and my own positive self-image. The other place I think this shows up is not necessarily people looking for real strong conviction in their own life, but looking for it from others. So our desire to follow the, say, guru that tells you exactly when the market is going to crash, or the wellness influencer that gives you the five-step plan to better gut health, or the mom influencer that says, this is the only way to get your... or six-month-old to sleep through the night and no other way it works. It's this desire to find

certainty about these uncertain situations where there actually is no certainty to be found. I mean, I think about that with Dave Ramsey's work a lot. Like, I'm obviously very critical of it. And I think one of the things that lacks is nuance. It doesn't talk about a lot of nuanced situations. It's very much like if you have debt, you should never go into a restaurant, you should always do this first. And I think that is why he has become so popular. The advice is very black and white. It's very like, this is what you're doing. There's no exceptions. And that's appealing.

That's appealing to be like, yeah, we're going to ignore all the systemic issues and racism and all of that. And we're just going to focus on just doing this. It's like it does feel very comforting. Yeah. Like the first chapter of the book is about someone who falls into like a religious cult. And I think a cult is maybe the best example of people looking for certainty where there's no certainty to be found. And it's incredibly alluring. You know, it's attractive for someone to say.

like if you just follow this protocol, you will go to heaven or you will achieve financial freedom or you will find your dream partner. The problem is when you are just outsourcing your worldview or letting someone else determine what you value, you're not actually wrestling with what it is that you value for yourself. Well, and something you just said struck me of like, I do think about the unfortunately very few people, but the people who do say I was wrong. I shouldn't have voted for somebody like Donald Trump. And I think it's very easy for people on the left to make that a pile on of like, oh, you just figure that out now.

And I actually think that might be the bravest thing humans can do is go, you know what, I was wrong because of what you just said of it being so attached and tied to our identity. Where if you've gotten to the point where you can admit, especially publicly or to your friends and family, like, yep, I had this belief. It was such a core belief. and I was wrong, that has taken a deep amount of bravery, but also a deep amount of inner work. Totally. Yeah, I think the other side of hubris is humility. And the humility to admit that you were wrong in the past is a sign of such strength. Like, I think the idea of flip-flopping has such a bad

brand. Like, we need to celebrate people who update their thinking based on new information, who are willing to change their mind. I think it's true from our leaders and our politicians, but also just true as individuals, we need to normalize being able to say either, I don't know or I was wrong, because those are the first steps to learning and to growth. And that's why I'm so passionate about this topic of uncertainty. Uncertainty is the precursor to learning.

You need to be able to admit what you don't know before you can know it. You are saying in the book that our tolerance for uncertainty is actually declining, that we're getting worse at this over time. What is driving that? There's some really fascinating research on this, too, from this researcher named Nicholas Carleton at the University of Virginia. And he basically has found there's a direct correlation between the rise of smartphones and the internet and our intolerance of uncertainty.

And, you know, this makes sense. When you have a computer in your pocket that promises to give you instant answers to every question that you have, it robs you of the practice of sitting with what you don't know. like even maybe 10 years ago, I might have been okay not knowing the name of a given actor. And now if I don't know the name of someone, I feel it almost like involuntary need, like in the movie itself to like look it up at my phone. And so I think there's two things going on. One is like our intolerance for uncertainty is rising, but also our felt experience of the uncertainty

in the world is rising. There's some research that shows that the five highest measurements of uncertainty in the past 40 years have all occurred in the past five years. So COVID wars, geopolitical instability, job market uncertainty. And so the world is uncertain. Our tolerance to that uncertainty is in decline. And that's why I think so many people feel so anxious and unmoored. I think one of the best examples of this, yes, is the,

I have to must pull out my phone to figure out that fun factor, that actor's name, but also the checking of comments. I cannot form my own opinion. I have to go, I experience this all the time, and I just recently started noticing, Tori, are you actually watching the thing and creating your own opinion on it, or are you being told what you should think by what's going on in the comments? And that was one I even noticed in my own life of, oh, I'm just letting random strangers dictate what I believe about this thing. Yeah, I was reading something about, particularly Gen Z, likes to read the comments before they

even watch the video. It's like, let me formulate the crowd's opinion before I formulate my own. And I think we see this in people who are looking at restaurant reviews and want to be absolutely sure about every situation that they're entering. I think there's two problems. One, as you said, it is a hindrance to our own ability to think and formulate our own thoughts about what we believe. And the second is that it just creates expectations. Like if you walk into every situation in your life, thinking about exactly what you're going to get and going to only 4.5-starred restaurants and going to only movies that have 95% on Rotten Tomatoes, you're never going to find the sort of surprise and serendipity of delight. It's like trying to watch a movie trailer before every single

life experience that you have. When we know that what brings our life texture is entering situations that you don't necessarily know how they'll turn out, entering into a conversation with a stranger, not assuming that you know everything about someone just because of who they voted for or, you know, what flag they fly, but going into those uncertain situations and being willing to have an open mind. I think if the book had just one thesis, it's that certainty closes our minds while uncertainty allows our minds to stay open. And that is the problem with so much of the certainty that gets peddled by TV news commentators and politicians and gurus on social media. They claim to have certainty about things that they frankly just can't know. Anything that hasn't happened yet

has some degree of uncertainty baked in. And the more that we're willing to admit that, the more accurate picture of reality we're able to see. I am very self-aware of I am the person who is checking the movie or checking the restaurant before I go. Absolutely. So I think it's something I probably need to work on. I mean, I don't think it's a problem, absolutely. I think in life we need some certainty and some uncertainty. Totally. But you're always doing that. Exactly. There's the problem. You've heard me talk about Built as the loyalty program that lets you earn points on rent wherever you live.

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this. I think we all deeply know this. And in fact, the day after the most recent presidential election, I did a whole episode about how I was going to remove myself from watching a lot of the, or listening to a lot of the news podcasts I was listening to. And I will say, it has bettered my life. Like, I feel so much better. And yet, I did feel like I have to prove that I'm informed. So we have more answers available than any other human beings in history, but it's somehow making things worse. Why is that happening? Yeah. I mean, let's start with the prescription. I don't think we need to like put our head in the sand and be like la la la I don't want to pay attention to court events at all. I just think that like tracking every political crisis or scandal in real time is not actually

making us feel more grounded. I mean parenting is a great example of this. I have a one year old and now you can like literally have an app that tracks your kids every movement. You can like watch them while they sleep if they are at daycare. There's expectation that you're getting like updates every 15 minutes, half hour, hour, hour. about what they're doing. And the more ignorantly blissful life is a little bit more blissful. I think there's, it's okay to not know exactly where your kid is or what they're doing in every moment of the day. We just let the sort of fear of this worst case scenario drive our behavior. I mean, it's the same thing with the news. Like, you can track real-time updates of the straight-of-hormuz,

but like scrolling down to refresh the New York Times, is that actually making you more informed and grounded? Or is that just fueling your anxiety about all the problems that the world has? You name the psychological phenomenon called escalating commitment where the more we're invested in something, the less like we are to change course

when we see it isn't working. And we talked about this briefly. But you use it to explain cults. We've had a couple different cult members on the show or previous cult members. I want to bring it even closer to home, though. What does escalating commitment look like maybe in our financial lives, in a job, in a general strategy for the way somebody's thinking about their career, maybe in a relationship,

like what does this look like in practice? There are so many financial examples. I think the best is probably gambling. Like you imagine someone in a casino and they've lost $100 and then they think, okay, I need to like make it all back. And so I'm going to bet $100 in the next hand and they double their losses. There's a few tactics that we can use to counter this tendency to want to escalate our commitment or double down or dig our heels in. My favorite is what's called creating a stop loss, which means, say, you buy a stock for $50. If you make a pre-commitment to either sell that stock when it goes down to 25 or sell that stock when it goes up to 75, you're making a rules-based decision that can't be swayed by your emotions. So the canonical example of this is people

climbing Mount Everest. And when you're climbing Mount Everest, there is a fixed turnaround time, which is 2 p.m. regardless of where you are in the mountain, at 2 p.m., you turn around because as a sun sets in the sky, the weather gets worse, the risks increase. And the reason they have that pre-commitment is to prevent you from it being sort of 155 and just trying to push all the way to the summit. And I think a lot of problems come to bear when we're in that position of making emotional based decisions as opposed to rules-based decisions, particularly in our financial lives. It can be really easy to feel the sort of emotions of financial nihilism or your uncertainty about your career and let that influence your portfolio or your strategy. But a lot of the best financial moves

are coming from a place of really clear principles. I'm going to have a diversified portfolio. I'm going to make decisions and think long term, as opposed to doing things on a short-term basis. If a stock goes up and down, or if the market goes up and down, I'm not going to make a rash decision just to, like, pull it out of the stock market

because I'm feeling anxious or unsure right now. And I think it's a great sort of case for outsourcing some of this decision-making, whether it is to like a financial planner or an expert or a third-party app or a robo buyer or something like that. So it's not on you to have to ride the emotional roller coaster of these ups and downs. Yeah. I mean, my strategy is always, you know, put it in an index fund and then you don't have to worry about a random company. It's like, cool. Every company that's, you know, it helps mitigate that risk a little bit. This reminds me, I have a friend who is an entrepreneur and decided years ago that

when she hit this amount of money in her investments, she was going to take a step back from her business. She actually did it. Like, she hit the amount of money, did not move the benchmark, and it has stepped back. And when she was telling me this, I know myself well enough to go,

oh, I would have moved the benchmark. I would have moved the benchmark. So what does somebody actually do in that moment when they're faced with a situation where they're like, okay, I set up the rule. So that was step number one. I set up the rule. But two, the rule's here. And I don't like it. It feels uncomfortable. Like how does somebody in that moment go, no, we're going to stick to the rule? I think in my life, what I try and do is try to outsource my willpower as much as I can. So for example, like for writing, it's hard to just like sit down and write when I say I'm going to write.

But if I have an editor that's holding me to a deadline or I have like a writing partner that's like, you know, going to check in with me and ask how much I've written this past week and how much I planned to write next week, those are ways of not just relying on my own will to get the thing done. And so one thing that you can do is find people to hold you accountable in your life to your commitments. So when your friend told you that she was going to step out of her business when she got to a certain point, That is a way of not relying purely on her own willpower, but actually outsourcing a bit of that willpower so that you can hold her accountable as well. That being said, it's really hard to do. We have this natural tendency both towards hedonic adaptation to sort of get accustomed to our new lifestyle creeps and to keep pushing the girl posts further out because then we start comparing ourselves to like a new subset of peers. And I think one of the things that has really helped me, I'm sort of, you know, a kind of middle class author, you know, and I think a lot of my financial anxiety comes from my ability to, like, provide opportunities from my kid and support my family, you know, my wife is a teacher. But when I

actually sat down and made a budget, it came from my head, the sort of like amorphous anxiety and fear and uncertainty about the future, into the practicality of, oh, this is actually how much I'm spending month to month. This is actually how much I need to survive. And so the sort of answer for me isn't just like always up and to the right, but it's actually to pay for a lifestyle and to be able to save and then know when my level of enough is. I think that's so smart and it's something just again from the like financial point of view, the amount of people I talk to who don't truly know their numbers. And yet they have so much anxiety around money. And they equate thinking, oh, looking at my money gives me anxiety. So I'm not

going to do it. I'm like, no, you're actually anxious because you have no idea what the fuck is going on. Like, that anxiety is not actually from, oh, I look at my money and I'm not doing as well. It's like, no, you're driving a car without a gas gauge. Like, you have no idea when your car is going to break down on the side of the road at two in the morning without cell reception in a place you've never been. Like, that is actually what you're stressed out about. You know, even if my lights on, it's stressful. I don't have a lot of gas, but I know how far I can get.

And I think that that is a very different experience than just rod-dogging life and expecting your anxiety to just go away. And you also made a distinction that I really love, which is that discomfort is not always a sign that there is something wrong. Sometimes it's a sign that you're really on the verge of a breakthrough. I just heard this. I'm listening to Emma Greed's new book. And what she talks about is like, fear is actually sometimes a good thing, because it means you are pushing past your comfort zone. It means you're doing something that is a little scary, but that has the potential to change your life. So how do we tell the difference between, oh, this is good discomfort.

This is something that is going to push me to get where I want to be versus, oh, this is my gut telling me this is bad. Yeah, that's a tricky balance to strike. I'll give one example that actually isn't in the book that I think is a nice sort of way to wrap up this question. There was a startup in the Bay Area in the early 2010s called Tiny Speck. And they were a gaming company. They built this game called Glitch that was heralded in the New York Times

when it launched. They raised like $17 million. They had tens of thousands of active players in their first few months. And it was this success story, like this incredibly hyped new multiplayer game. And yet the founder felt in his heart of hearts that the business wasn't actually sustainable. It wasn't on a path towards success. And so he did something that others might have seen as crazy. He decided to shut the company down at sort of the peak of its success.

and he offered to make his investors whole. He gave employees the opportunity to leave if they wanted. And then with the employees that were left, he decided to pivot the entire company around this internal tool that they had built to communicate with each other while they were building the game. And that internal tool is Slack, one of the most successful B2B businesses of all time,

and the founder's name is Stuart Butterfield. And you hear him talk about this decision to turn towards the unknown. And he said, we didn't know exactly how it was going to turn out. We didn't know the opportunity that we were pursuing. But what he was able to find was that on the other side of his discomfort, the other side of his fear was something that was greater than anything he could have imagined.

There's this metaphor that gets used often in statistics, which is the idea of like a local maxima, where you might be standing on the peak of a mountain. You think, like, I'm on top of the world. but you might not know that around the corner there's another peak that's a little bit higher and requires you to descend, maybe face some of that uncertainty, face some of that discomfort, but then you can end up higher than you ever did before. And that's maybe a piece of advice that I give to our friend that's stuck in a dead-end job

or stuck in that dead-end relationship is that uncertainty doesn't necessarily have to be a sign that something is wrong. It can be the beginning of a new chapter or a breakthrough. Is that the thing that breaks the cycle? Like when someone's in that wrong job, the wrong relationship, the wrong financial pattern, when they can see it but can't move, is that the thing that breaks the loop? The thing that breaks the loop is action. You know, there's a common phrase, which is that action absorbs anxiety.

And I think that's incredibly true. Like the metaphor that I like is that being a leader in a business or in your own life is like rowing a boat on a lake that shrouded in heavy fog. You might not be able to see very far in front of you. You might not be able to know exactly where you'll end up, but you have two jobs. The first is to maintain faith that you'll eventually reach land. Remember, you're on a lake.

And the second is to keep rowing. And I think the keep rowing is the key. You know, I think so often the sort of cost of our discomfort with uncertainty is that it keeps us paralyzed. We feel that sense of doubt or that not knowing, and it prevents us from taking any action at all. Whereas the only way to move through your anxiety is to take one step at a time,

and that's how the clarity will emerge. I love having Simone back as a guest, and you just heard him talk about fear and uncertainty around money, and if you thought, well, cool, that's me. I know I could be better with my money, but I feel so frozen. I know exactly where you are, and I've literally built a program just for you. The 100K Club is the place to learn everything you need to know about money at a basic level.

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slash ff pod. All right, let's get back into the episode. Tell me about Connie and Andrew. and why you chose to open your book with them? Fascinating story. They are a couple. They've been together for 17 years, married for 10, and they both sort of know that there's something that isn't quite right in their relationship. And so they're out having a drink at a bar,

and they decide to do an experiment, and they call it the year of living dangerously. And what they do is they say, we're going to go our separate ways for a year, and then we're going to come back to this bar, a year from today and determine whether we want to stay together or not. And when I first heard it, I was like, this is like fiction. You know, like this isn't real life.

Like, people actually do this. And they did. You know, I won't spoil the ending of like what they determined. Like when I do sort of my informal poll of like, do you think they broke up or stayed together? It's like 50-50. You know, half people are like, it's the Pinia Colada song. Like, of course, they fall back into each other's arms. And like, the other half of people are like, no, there's no way that they like stayed together

after like spending a year giving their energy outside of the relationship. But I think it's this fascinating little case study of what would it mean to actually turn toward the uncertainty you're feeling in the relationship? And this isn't to say that like everyone should like do their year of living dangerously or their like relationship, Rum Springer or whatever. But it was so fascinating to talk to them. And maybe the kicker is that they're a couple's therapist with Esther Perel, like the most famous couples therapist of all time before Esther Perel became like Esther Perel.

became like Esther Perra. And so I got to like talk to all of these experts about the situation. I talked like an ethicist and a philosopher and a psychologist to all get there sort of read on what was going on. And it really kind of changed the way that I think about decision making. Okay. So most people who are listening to this, I would dare to say maybe all, are people with kids or people with a financial condition where they, you know, they don't have the ability to do this. or, you know, they're like, yeah, I can't break up my marriage for this. So, like, what is the accessible version of the year of living dangerously? Like, what does a personal experience or personal experiment like look like for this person listening?

Yeah, I think that's sort of the upshot that we can all take from it. Like, what would it mean to prototype a question that you're wrestling with in your mind? So maybe you're considering moving. Rather than just treating it as like a thought experiment, could you go to, you go to? to the city that you're considering moving to and like rent an Airbnb and like try it out for a week, say you're considering like switching career paths or switching your jobs. Rather than just be in your mind thinking like, is this really what I want? Is there a way that you can get proximate to the actual experience of doing that work? Like for example, I am a writer. I got a lot of people

in my DMs that are like, hey, I want to write a book or hey, I want to be a journalist. Like, what should I do? And the first question I always ask is like, what do you like to write? What have you written recently. And the most common response is like, well, I haven't actually written anything, but I have all these ideas of what I might want to write about. And my advice is like, just go write the damn thing. Like you don't need anyone else's permission to try and run a time bound, low cost experiment to try and give you more information about the thing that you're trying to decide between. And I think it comes back to this paralysis point where so often when we're at a crossroads, we just feel stuck.

And it's through that action. It's through maybe lowering the sakes and creating a little safe environment where you can try it out, that you actually will get more information. I talked to this therapist about the Connie Andrews situation. And he said that when people are really uncomfortable with uncertainty, they tend to go one of two ways. They either become really impulsive or they become like insane information gatherers. And you probably know just listening like whether you're on one or one. under the other end of the spectrum. You know, we all have that friend who's, like, trying to decide what job to take or something,

and they, like, ask everyone, and they can't, like, their Uber driver and their yoga teacher and their best friend. And, like, they don't actually get quiet enough to listen to what they think for themselves. Or we have another friend who, like, just, like, makes really rash decisions, which I think is its own way of, like, avoiding turning toward uncertainty. Like, the example the psychologist gave me is, like, if you're really uncomfortable with uncertainty and you need to buy a new pair of genes, and you need to buy a new pair of jeans, you maybe either try on every single pair of jeans in the store or you just buy the

pair of jeans in the window, whereas a more adaptive approach might be like, try on three pairs of jeans and figure out what you like and then make a choice. Two things from that that I find so interesting. I'm trying to remember where this quote is. It might be the artist's way, but basically like, if you want to be a writer, write, then you're a writer. Like, no one is coming to bequeath you and knight you and say, you are officially a writer once you have published a book or a New York Times bestseller or written 10 books. It's like, if you write, you are a writer. If you act, you are an actor.

If you do improv, you are an improviser. There is no person who or society that's going to tell you, oh, you haven't achieved this so you're not the thing yet. If you want to be that person, you just have to become that person. And the thing with, you know, uncertainty of, are you the person that's going to be impulsive? Are you going to do, you know, every single Google search you can? I see this so much with money, which is either, for me,

would be ostrich effect, which is like bury their head in the sand, act like their financial problems don't exist, they're like, oh, I'll just ignore it. Or the opposite, which is like so much research but no action. And we call that analysis paralysis where it's like, I am not going to open the high yield savings account that I've heard Tori talk about a million times. I'm going to Google best high yield savings accounts and spend like 10 hours over the next couple weeks researching, which should be like a 10 minute decision. And so those are the way. ways I see the inaction crop up with our community in particular is it is like I'm either going to completely ignore it. I'm just not going to do anything about it or I'm going to do so much

about it that keeps me from actually doing anything. Totally. Yeah, I see this in my own life all the time. Like the other week I was feeling super addicted to my phone. And rather than just like put my phone down, I read an entire book about phone addiction. There's got to be like a German word for this. like you like do something that's like adjacent to the thing that you want to do as opposed to doing the actual thing. It's like rather than start the business, I'm just going to like listen to a thousand podcasts about entrepreneurship, you know? Well, because we're, we're uncomfortable with uncertainty. I mean, it's all back to your thesis statement. It is, it's actually easier to read the 12 books about how to start a business and to watch the 100 videos because that means you don't have to take a risk.

That means you don't have to do anything. You can say, oh, I'm doing research. No, actually you're at the point where the research has been over for a while. You're just using that as an excuse because you're just terrified to actually get started. Yeah, there's two frameworks that help me make decisions. The first is just understanding the difference between one-way door and two-way-door decisions. So one-way door decisions are decisions that are decisions that are, harder to reverse. You like walk through the one-way door and it's harder to go back on questions like

who should I marry? Like should I buy this house? Should I assume all this debt to go back to graduate school? Two-way door decisions are decisions that are easier to course correct. There are decisions like, you know, should I open the savings account, which if I figure out it's the wrong choice, I can probably go back. Should I like order the pizza or the pasta, whatever? And the problem is so often we take the analytical framework of a one-way door decision and apply it to a two-way door decision. Like even a decision that feels high stakes like what job should I choose, we have much more agency and ability to adapt and course correct than we give ourselves credit for. And the real risk is that you never transact, that you never actually make a decision

because you're waiting for that certainty that may never come. Like how would you know which of two jobs is better for you until you actually start working one of those jobs? Like we have to be able to make decisions not in the absence of uncertainty, but in spite of uncertainty. And that's what it means to be a human. We have to be able to make decisions in spite of doubt. And I think the most successful people do exactly what you just said. I've never heard it approached from that. And so I think that's brilliant.

the one way door versus the two. Like, I think that if you look at the most successful people, they are very good at making a decision and being like, okay, if it's not the right decision, I'm actually quicker to figure out it's not the right decision and make a change rather than spending all of this time doing nothing. It's like, nope, I'm going to make a decision. I think it's the right decision.

And usually it is. And if it's not, then my energy is actually in course correcting as soon as possible as opposed to A, waiting to make a decision at all, or B, not course correcting because of all of the hubris we were talking about before. Yeah, there's this philosopher named Ruth Chang, and she has this great idea, which is what makes a hard decision hard is that one option isn't better than the other option overall. One option is better for some reasons. Another option is better for other reasons, and yet neither is better overall. If one option was better, clearly, it wouldn't be a hard decision. it would be an easy decision.

And so rather than agonized, going back and forth, creating the pros and cons list, creating the spreadsheets, talking to your Uber driver, you just have to be able to accept the trade-offs that you're willing to choose, and then retroactively you can spend your energy convincing yourself of why you made the right decision. Another way to think about it is there's this ethicist

who I talked to named Ira Bredzel, and we're talking about sort of moments of indecision in life. And he is a guidance counselor at a university. And he says he always asks his students the same three questions. The first is what do you want to do, which is a way to try and get out of our head and into like our body, our felt experience, our gut. The second is do you want to want to do that, which is a way to sort of abstract a little bit from the decision itself and tap into what's often called our higher order self or our second order desires. Like I want to smoke a cigarette, but I don't want to want to

want to smoke a cigarette. And then the third is, what does this decision say about who you are as a person? And that is a way to try to connect your decision to your values and your identity. And hopefully, we can make decisions that align with our values so that even if we don't get the outcome that we desire, we can still stand by that choice. And I think that is a really freeing way to think about uncertainty and decision-making. How can you make choices that reinforce the type of person that you want to be? Because you never know exactly what the outcome will give you. And to be honest, as humans, we are really bad at what psychologists call effective forecasting,

which is thinking about how we're going to feel about how future events will affect us. The canonical examples are like people that get left at the altar or people that win the lottery or people that become paraplegic. We all have a friend who like went through a breakup and then was like, that was the worst thing that ever happened to me. It's my life is over. And then you talked to them six months later and they're like, that was the best thing that ever happened to me.

What a blessing in disguise. And that's a great example in that to like rush to certainty about how an event will affect you is we honestly don't know. I've talked on this show before that in, yeah, 20, speaking of breakups, I went through a very hard breakup. But it was hard because I thought this person was my soulmate.

Like I thought this person was my person. And so, you know, I look back at the, that time and at that person I was with such fondness because it was, you know, many people have breakups that were terrible and it is like devastating for that. But it was devastating because I thought, oh, I'm losing the person I'm supposed to be with. And one of the worst things I did was I tried to muscle through the grieving process. And I was, you know, I was feeling very deeply. I thought I was doing it correctly. You know, I was crying a lot. I was feeling a lot of emotions that,

you know, very up and down. And I thought, you know, I was doing it correctly. And then finally one day I realized like, oh, I'm just trying to get to the end of this so that I can, this all, this whole experience can have meaning. Because if it doesn't have meaning, then this is just hard. And as, you know, again, cliche as it sounds, I just had to sit in it and time did its thing. And that was what truly allowed me to like recover and grieve and then look at that relationship and be like, oh, that was the best thing that ever happened to me. it forced me to deal with uncertainty. It forced me to sit in it and not know what was coming next and be okay with the unknown. And yeah, it's taught me so much about the way I live my life,

but it was deeply painful while it was happening. It was not a fun experience. Yeah, the canonical psychology finding. The only way past something is through it, you know, Carl Jung. I think that is so true about every anxiety that we have in our lives. Have you ever heard of the the parable of the Chinese farmer. Oh, I have it as a question, but I would love to hear it from you. This is the horse running away, horse returning. Is that what this is?

Yeah, exactly. Yeah, I mean, I just think it's such a great little story that gets to the heart of a question about, like, will a breakup be a good or a bad thing? Yeah, tell us. Tell it for us. So there's this farmer, and his horse runs away from the village where he lives, and his neighbors come to his door and they say,

we're so sorry to hear about your horse. It is such a tragedy. and the farmer says, maybe yes, maybe no. The next day, the horse comes back, and behind it, there are seven other wild horses in tow. And so the farmer is just like, you know, eight-ax to his supply. And the neighbors come to this door and they say, oh, we are so grateful to hear about your horses, what luck. And the farmer says, maybe yes, maybe now. The day after that, the farmer's son is taking out one of the wild horses for a ride.

and he falls and he breaks his leg. And again, the neighbors come back and they say, what a bummer, we're so sorry to hear about your son. And the farmer says, maybe yes, maybe now. And the day after that, generals from the military come to the small village to draft people into a war. And because the son has broken his leg, he gets out of the draft. And the neighbors, again, say, you're so lucky.

This time you can join me, the farmer says, maybe yes, maybe no. And what I love about that story is that it shows the wisdom of not rushing to judgment about how something might affect us. There are so many financial versions of this where we think that our portfolio is ruined or we're going to the moon because crypto went up or whatever. And really, like so much financial advice is I'm sure you dispel on the show, comes back to putting yourself in a situation that can weather some of those ups and downs and trying to stay the course. Because, you know, Nvidia goes up one day, what great luck. Next day, like a news headline, the stock goes down. What a tragedy. And if you are just riding that emotional roller coaster, that's no way to feel grounded in your life. That's no way

to feel stable and secure. That's no way to actually get what you were looking for from your money, which is like opportunity to make choices. And so by reserving the judgment to think about any event as like a blessing or a curse right in the moment, we allow ourselves to stay in that space of unknowing and stay in that place of uncertainty where we can actually see what emerges as opposed to just trying to validate our assumptions. I've been the collecting staples lately. I've been a lot more intentional about finding pieces in my wardrobe that I can just drag and drop. I literally came from packing for a work trip to record this. I have my cute little tank top from Quince that I wear for everything. I've worn it on stage. I wear it out on a date.

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the idea of like every choice we're making is our other possible selves sailing away. And I, if you were to talk to my partner, he would joke that, like, peak Tory porn is any sort of media that talks about timelines or, like, you know, books, movies that talk about, oh, this one decision. If I made this one different decision, how would my life look? So for a listener who is realizing that some of those ships have sailed, some version of herself is not going to be, what do you want her to take from that idea? So the image is, you know, every decision you make, there are many different decisions, many different paths that your life can take. And you can see each of them represented by the decision to, like, jump onto a ship. And the minute you jump onto a ship, all of these other ships sort of depart from the dock. They're all the other people you could have been. and we can't ride every single ship.

The takeaway is that you have to be able to make peace with those ships that you didn't take. And part of what makes decision making so difficult is the moment before you make a decision, all options are still on the table. All those ships are still possibilities in your life. And then you step onto a ship and immediately you foreclose all those other options, which feels like this incredible loss. And often in the immediate aftermath of making a decision, you can't necessarily see what will come of the decision

that you've chosen to make. You just can feel all the decisions that you didn't make. Choosing to marry this person means that you can't marry that person or that person or that person. Choosing to move to this city means that you can't live in that city or that city or that city. But there's an incredible freedom if we are able to accept that we can't ride all of the ships. I used to be an international correspondent, like a travel journalist.

And I remember when I was like 26 or so, I had this realization that you can go to a city like Paris. You're never going to be able to see everything. Or eat at every restaurant. That's the one that always gets me. Or eat at every restaurant. I can't eat at every restaurant in this city. But the natural extension of that is like, then maybe it's okay to go to Paris and not go to the Louvre. and you don't have to feel about the opportunity cost of how you've chosen to spend your day, you can just be grateful for how you did spend your day. And so the sort of ghost ship's story comes

from the decision about whether or not to have a kid, which I know is one of the hardest decisions for a lot of people, especially in this world that we're living in. And you can look to like a guru like Cheryl Stray to say, like you should definitely have a kid or you should definitely not have a kid. But the truth is each of them is a choice that will come with different life paths for you. You'll have the opportunity to make new choices.

And if you want to live at peace, you have to be willing to wave at those ghost ships as they fade into the distance. And find like a genuine, I don't know, like both. It's actually very similar to the way I view that relationship that ended where, you know, I don't have any longing for, that relationship anymore, I just have a quiet contentment of just like, yeah, I genuinely cared about that person. I continue to care about him, but I don't long for that anymore. And I think that is hopefully how we can view our ghost ships, where it is an understanding of like, that would have been a path my life could have taken, and I probably would have been very happy. But that's not, that wasn't the path that happened. And so rather than, you know, I,

again, I went through my grieving process, but rather than continue to, like, long for that and then make myself miserable, there is this quiet contentment of, yep, that wasn't supposed to happen, at least not this lifetime. So, yeah. Have you read the book, The Bell Jar by Sylvia Plath? I actually have never. It's on the list of, like, I will get around to eventually. It's like, you know, of course, like canonical high school English class book. But there is this great image at the end of the book. about this woman, the protagonist, sitting underneath the fig tree. And she looks up at the fig tree,

and each fig seems to represent a possible path that her life could take. There's like the path where she marries this man or a path where she marries this man, the path where she becomes an astronaut, and a path where she becomes a banker, a path where she chooses to pursue this sport and goes to the Olympics,

and the path where she moves to the woods and becomes a writer, what have you. And she's beautifully talking about all of these different potential paths that her life could take. But in her indecision, she's just sitting there under the fig tree, and slowly the figs are rotting and falling off the tree. And then there are no more paths that are available to her. And the lesson is that you have to choose a fig.

You have to get on a ship. You have to transact in the world. And I think probably what would have been the worst thing that happened to you out of that breakup is for you'd be so fixed on that one relationship to think that the only way that your life could progress is if you went back to the way things were. And that's what made me miserable. And that was the source of your misery. For that first year, I could not move forward past that. Yep. It sounds like I'm going to have to add the bell chart of my list because that is my name written all over it. I wanted to end our conversation if you're vulnerable enough to talk about it. There was a moment in

your book where your wife, Katie, went through a miscarriage. You both went through this miscarriage. And then also the subsequent pregnancy, which congratulations on your child. You're writing this book about uncertainty while living inside one of like the scariest kinds of uncertainty. So what did actually living the material teach you that the research didn't? Yeah, great question. So the story is basically, you know, my wife and I were trying to get pregnant. We got pregnant. We were so excited. You know, we named the unborn baby Poppy because the first time we, like, looked up the app of his size. He was the size of a poppy seed. And, you know, we wanted to be parents for a long time.

And we go in for a doctor's visit around, you know, 10 weeks or so. And the doctor says, basically, at this point, we'd expect to see a heartbeat, but we're not willing to call it just yet. why don't you come back in a week and then we can check in there. And, you know, I'm writing this book about uncertainty. I had just written about this one particular study where they found that for breast cancer patients, often the uncertain period between when you get a biopsy and you get a diagnosis is the hardest part of the entire breast cancer journey. Harder than chemo or any surgeries, it's the waiting. And here we are in this week of waiting.

and with this dream of having this kid that we wanted to have for so long. And in some ways it was hell, you know, like in some ways I thought back to this shock study and I was like, just shock me already, you know, like, say the quiet part. Yeah, say the quiet part out loud. But there was also something really beautiful about that week of waiting where, like, Katie and I would be at a party and we'd, like, catch eye contact with each. other and like hold it for a little bit longer or just like you know have a little bit more sweetness and the way we held each other's hands as we are waiting to receive this news and

the mantra we kept repeating to ourselves was um we are open we are open and we come back a week later and we got the bad news that we lost the we lost the pregnancy and you know thankfully we were able to get pregnant again there's like a happy ending to this story but I don't think the fact that there was a happy ending is what makes the story illustrative. I think the beauty of that experience for us, tragic and painful as it was, was that it really made us understand what we cared about and how much we cared about each other and what it is that we valued. And one of the pieces of advice that I give at the end of the book is to,

find your anchors? What are the things in your life that will remain certain amidst all of the changing winds? And my relationship was an anchor. I knew that Katie and I would go through this experience together regardless of whether we got the good or the bad outcome. And another piece of advice I give was to separate what you can and you can't control. And as much as we wanted that baby and that pregnancy to work out. And for the doctor to say, we found the heartbeat, everything was okay. Everything's fine. Yeah. There's nothing we could have done. And so rather than resisting reality, we had to accept reality. And through that experience, we were able to grow. Okay, hello. If you're watching on YouTube, I had to take a minute because that made me very

emotional. But I do want you to plug your incredible book because I'm excited to read it for where I'm at in my life and I think everybody listening, whether it's a moment of uncertainty you're having now or sometime in the future, this will be applicable to you. So I'm so excited to have you back on the show. Please tell us about this new book. Yeah, the book's called How to Not Know. I think the cliche for authors is that you write the book that you need to read. Yeah. But I feel like I'm also the beneficiary of very good timing. So whether you're anxious, about the uncertainty in the world or in your career or something in your personal life, I hope there's something in it for you, and you can find it wherever books are sold.

You're one of our favorite, most thoughtful guests. Thanks for coming back. Thanks for having me. Thank you for listening to Financial Feminist, produced by her first 100K. If you love this show and want to keep supporting feminist media, please subscribe or follow us on your preferred podcasting platform or on YouTube. Your support helps us continue to bring this content to you for free. If you're looking for research, resources, tools, and education, including all of the resources mentioned in this episode, head to herfirst00k.com slash s-spod.