We Study Billionaires - The Investor’s Podcast Network - TIP580: Clear Thinking w/ Shane Parrish

Starting point is 00:00:00 You're listening to TIP. On today's episode, I'm joined by Shane Parrish to discuss his new book, Clear Thinking, turning ordinary moments into extraordinary results. Many people fall prey to making decisions based on our instincts and our gut feelings. Shane's book gives you the tools to recognize those moments that reshape how you navigate the critical space between stimulus and response. Shane Parrish is the founder of the highly esteemed blog Farnham Street, and he's also the host of the Knowledge Project podcast where he focuses on mastering the best of what other people have already figured out.

Starting point is 00:00:36 Shane's work has been featured in nearly every major publication, including the New York Times, the Wall Street Journal, and Forbes. During this episode, we cover how Shane differentiates between high quality and low quality information, what the enemies of clear thinking are, why we should prioritize the outcome over the ego, preventative measures we can use to combat the enemies of clear thinking, why we can't rely on willpower to achieve the outcomes we desire, frameworks related to differentiating our outcomes from our underlying decision-making processes, what the truly important things are in life for Shane and how he remains grounded in what's most important to him,

Starting point is 00:01:14 what led Shane to invest alongside Howard Marks and Bill Ackman when joining Tiny's board and so much more. When going back and listening through this episode, there are just so many parts that made me stop and really think through it. And there's so many tips here that we can use to make better decisions, whether that be in investing, in developing relationships, making choices in our careers, and so on. Shane is incredibly thoughtful, and I really appreciate him taking the time to join us on the show for the second time. With that, I really hope you enjoy today's episode with Shane Parrish.

Starting point is 00:01:46 You are listening to The Investors Podcast, where we study the financial markets and read the books that influence self-made billionaires the most. We keep you informed and prepared for the unexpected. Welcome to the Investors Podcast. I'm your host, Clay Fink, and today I'm absolutely thrilled to be joined by Shane Parrish, Shane. Such a pleasure having you here. Thanks, Clay. Excited.

Starting point is 00:02:21 Well, I just read your new book. It's titled Clear Thinking. And as I was preparing for this interview, funny enough, you were on the show with Preston and Stig back in early 2018, so over five years ago. Also, we studied billionaires. It was one of the earlier podcasts in the space that started in 2014. And as I was researching, I noticed that your podcast was also very early on in the space. As you released an interview with Michael Mobison back in episode one in 2015. Yeah, we're part of the OG podcasting crew here.

Starting point is 00:02:53 Well, let's dive right into the ideas in this book here. When I look at you, Shane, and I look at the work that you do, I think that you're very much in the pursuit of wisdom. and you're reading all these books, studying all these great people and, you know, having all these experiences and then bringing in that wisdom and then sharing that wisdom with the world. I'm curious how you differentiate information that's low quality and maybe not as helpful from that information that you believe is true wisdom that will stand the test of time. Yeah, so there's a couple ways to do this.

Starting point is 00:03:25 And one of the ways that I sort of differentiate between high quality and low quality information is sort of from the source, right? So if I'm reading something in a newspaper, for example, and a journalist is writing about it, and that journalist writes about 52 articles a year, and there are 52 different topics, I know it's probably not the highest quality information of inputs that I can get. And that doesn't mean anything to the journalist, it just means that they're not an expert in that particular subject. So you want to go to people with direct expertise, and you want all the nuances and details. And I think this is where people get mistaken when they search out information. They're looking for the answer. And if we, let's just back up for one second and think

Starting point is 00:04:04 about how we learn. I have a concept called the learning loop, which is how we actually learn something. And so you start with an experience. Imagine a clock. At the 12 hand, you have an experience. At the three hand, you have a reflection. So you have a reflection, you reflect on that experience, and you create a compression or abstraction, which is the six hand. Based on that compression or abstraction, you go to the nine hand, which is an action. So you can just imagine this in your head, right? You go from experience, reflection, compression, action, which leads to an experience. And so often the information that we consume is we're actually consuming other people's abstractions or compressions. And that works for the person who creates it. But for the person who doesn't

Starting point is 00:04:46 create it, it's the illusion of knowledge. It's like me when I'm at home making a recipe. I can make that recipe for all the instructions, but, you know, maybe I miss a step or I forget something and it doesn't turn out quite the way I want it to. But the person who created the recipe, the chef who created it, they would instantly taste it and know exactly what happened. That's the difference between sort of the illusion of knowledge and actual knowledge. If things go right, it tastes the same. If things go wrong, the person who actually earned the knowledge knows exactly what to do, what went wrong, why it went wrong. And so when we're looking for high quality sources of information for something that we want to be an expert in, we're looking

Starting point is 00:05:24 for detail and we're looking for nuance, which is the opposite of sort of the world, the information world that we live in, which is full of sound bites and full of these one sentence, wisdom, quotes, and all of that. So you want to look for somebody really close to the problem and you want to look for a lot of detailed information about it. And you want to vacuum that information up yourself. You don't want to have a filter in between you and that source of information. And you want to, if you're talking to somebody, because if you think of experience, it's not just direct experience. You're experiencing something when you read a book, when we're having this conversation, it's an experience. And so when you're having that experience,

Starting point is 00:05:58 you want to see how somebody reflects on the information because that's going to help you distill with a lot more context in your head about what happened, why it happened, what's likely to happen in the future. But it also changes the questions you can ask people. So when it comes to asking people for input or advice or anything like that, what you're really trying to do, if you think about learning this way, is I want to know how you reflected on the experiences you had. It's not what is your compression or what is your abstraction? It's why did you come up with that? Like, how did you distill these gigabytes of sort of raw material into this sound bite? And why do you think that that's valuable? And what are the edge cases and what are the limits to that knowledge? And these are all

Starting point is 00:06:38 sort of the questions that you can ask to get higher quality information. A great example is, like, if you go to your doctor and he says, hey, you need heart surgery and you go, who should I use as a surgeon? That's going to give you the answer. But if you ask him, how would you think about picking a surgeon, that's going to show you how he thinks about it and why he thinks that way. I love that. For the introduction of your book, you discussed the power of clear thinking in the ordinary moments. And when I think about something like the Pareto principle, it would suggest that few big decisions are going to drive a lot of the direction in our lives. You think about who we marry, the career we select, the city we live in, who our friends are. But you actually

Starting point is 00:07:15 argue that it's the decisions in the ordinary moments that matter most to our success. So I'd love for you to expand on this concept here. This is hard to appreciate. So perhaps an example, we'll just make it very salient to people. You can pick the right career, the right person to marry, the right town to live in. You can get all of that right. And in those moments, you know you're making a decision. So you consciously weigh tradeoffs. You think about it. You're generally right. Often we're mistaken, but we're mistaken sort of like later on because things change or something's different. We're not mistaken in the moment. We usually generally make those decisions right. But if I pick the right career for me, and I don't show up Monday morning

Starting point is 00:07:55 every Monday and work my butt off, it doesn't really matter that I pick the right career. It just multiplies by zero. If I pick the right partner, but I don't invest in that relationship and I take it for granted and I'm not there when they need me and I'm not a good partner, it just goes to zero. But all of those things I just mentioned are the everyday ordinary moments that we don't think about. And what tends to happen in those ordinary moments is we don't realize we're making a decision. A great example is sort of a common one that I hear is sort of the dishwasher. One partner loads the dishwasher one way. One partner loads the dishwasher the other way.

Starting point is 00:08:32 And this is a source of tension in quite a number of relationships for some reason. And so you come home and it's been a long day and all of a sudden there's a little passive aggressive comment. And that passive aggressive comment, then you escalate. you reply with a passive aggressive comment. And before you know it, you're basically like not talking to each other on a Friday night. And nobody wanted that outcome. And nobody was conscious about that.

Starting point is 00:08:53 If I tapped you on the shoulder halfway through that and said, hey, Clay, you're about to pour gas on this situation or water onto this situation when you reply. Then all of a sudden, this ordinary moment, you would be like, oh, I want to put water on this. But you don't know you're doing that because you're just responding. Your defaults are in charge and your biology is in charge. And so if we want to tie this to some of the concepts in the book, like, we're animals. Like, we're just, that is who we are. The difference between humans and other animals is that we have the ability to reason before

Starting point is 00:09:25 responding, whereas no other animal really has that ability to the extent that we have it. So what do we share in common with animals? Well, we're territorial. We're self-preserving. We're hierarchical. And then also, on top of that, we're emotional, we're ego-driven. We follow the social cues of society. and we follow inertia.

Starting point is 00:09:44 And so we have all of these things working to basically circumvent our ability to think in these moments. And then what happens is the situation ends up thinking for us. And so when I say territorial, let's put that in context because people think, oh, like, I'm not territorial. You know, I don't go around pissing on the corner and sort of marking my territory, like a dog or a wolf. Well, no, but your territory is your identity and how you see yourself.

Starting point is 00:10:07 So a passive aggressive comment from your partner all of a sudden triggers a biological instinct for you to respond. And when it triggers the instinct, you're not thinking. You know, when you tie this into investing, I think about how people just become their own worst enemy when it comes to the decisions we're making. And that's why I think this book is so important. It's understanding the common pitfalls we have. And that's what's covered in the first part of your book. You call it the enemies of clear thinking, essentially outlining all these biological hardwirings that are ingrained in us. And we don't even realize that, you know, we're just acting based off our instincts. So like, something goes up and we get FOMO and we just kind of chase because everyone else is getting into it. So what are

Starting point is 00:10:50 some of the common pitfalls you found that people fall prey to when it comes to these biological instincts? Well, it's just that, right? So it's like if somebody slights you into meeting, you're going to respond. If you're emotional, you're hungry, you're angry, you're lonely, you're tired. We talk about halt in the book, which is a cue for Alcoholics Anonymous, you're going to respond. If you're thinking that you're right and everybody else is wrong or you're trying to prove yourself right, you're going to ignore information. You're driven by ego. And so you're putting your ego ahead of the outcome. The phrase that I like to use all the time with myself, it's actually here for a video, it's a little sticky note that's on my desk, on my monitor, and it says outcome over

Starting point is 00:11:31 ego. And that's just a little visual reminder to me that like I'm searching for the best outcome. I'm not searching to satisfy my ego. My ego is satisfied by the best outcome. And I think that we just don't think about these things. Like, we're socially pressured into these situations. And so if you want to think about clear thinking, it sort of boils down to three core elements. The position that you're in at the time you make the decision, and the position is all the things that lead up to the moment of the decision. And can you manage these urges that get other people in trouble when it comes to your emotion and your ego? And can you recognize when you're not thinking, in the situation is thinking for you, such as inertia or a social situation. And then when you do

Starting point is 00:12:12 that, you have the ability to think independently. And what you're trying to do, whether you're investing, you're running a business, or you're just working in an organization, is you're trying to create positive deviation. And positive deviation only comes when you go against what's happening and you're correct. You can't just go against what's happening. You have to be correct. And I think most people miss that. And so it's good to follow best practices, but you need to know when to opt out of those practices where it doesn't make sense. So a couple of the points you hit on in the book, you have the ego default and the inertia default. And I think it ties in well where, you know, an object in motion tends to stay in

Starting point is 00:12:49 motion. So you buy it into a company and you can fall prey to just hanging on to it because we don't want to regret having to sell it. So we're kind of protecting our ego in a way. If you sell it out of loss, you don't want to regret it and watch it rise after that. And it also is really painful to admit that you were wrong. Yeah, that's the biggest problem. So putting the outcome ahead of your ego is just really an act of admitting that you've made a mistake in those cases. The very act of investing, though, is an ego-driven activity. You're buying from somebody who's selling. So you are assuming that you're smarter than they are or that you're going to get a better result than they are or you have a longer time horizon than they do. But there's all these

Starting point is 00:13:33 fundamental assumptions that go into that, that drive that behavior. But the act of buying an individual stock is fundamentally an ego-driven behavior. And your ego helps you. Like our ego isn't all bad, right? It compels us to sort of like try to land rockets on the moon and put up satellites in space. And it compels us to build higher buildings than we've ever built before. And it compels the world to go forward. On an individual level, ego can be very destructive. But on a societal level, it tends to, so far, it's worked out to our advantage, all the weapons of mass destruction aside. But like, we just need to know when our ego is serving us and when it's not. And you can sort of come up with situations. Like one example is like, how do we get out of these

Starting point is 00:14:16 defaults, right? The emotion, ego, social, inertia. Like, what do we do to sort of step out of this? And, you know, I'm angry. I'm going to make a decision. Well, you know, in that moment, I don't recognize that I'm angry. So it's one thing to say, please, you know, you just have to catch yourself and take a breath. We sort of talk about that in the book. That's one element to sort of avoiding these situations. But can you avoid them? Can you create rules to circumvent them when they do happen?

Starting point is 00:14:41 And fail safe being, if I can't do any of that stuff, then can I recognize that I'm in the moment and do something about it? But every other book I've read about this is like, oh, you just need to recognize your hands getting your jaw getting tight and your hands getting sweaty and then you're angry and you shouldn't make a decision. And everybody I've talked to, it's like maybe you get 20% of the time. You actually can catch yourself in the moment. But most of the time, I don't know, but you ever send a nasty email, right?

Starting point is 00:15:08 You're angry. You're just, like, sitting there typing. And in that moment, like, you're angry. But, like, you don't think you're angry. You're not making a decision in that moment. So, like, you need sort of like safeguards to avoid that, which is like, I don't send email after 9 o'clock. Or you can come up with these little automatic rules to prevent that from happening

Starting point is 00:15:26 or time delay, which is, you know, every email I, I type after 5 p.m. I just send the next day. That gives you a little bit of space between what's happening and sending. Let's take a quick break and hear from today's sponsors. All right. I want you guys to imagine spending three days in Oslo at the height of the summer. You've got long days of daylight, incredible food, floating saunas on the Oslo Fjord, and every conversation you have is with people who are actually shaping the future. That's what the Oslo Freedom Forum is. From June 1st through the 3rd, 2026, the Oslo Freedom Forum is entering its 18th year, bringing together activists, technologists, journalists, investors, and builders from all over the world, many of them operating on the

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Starting point is 00:19:48 You have a number mentioned in the book. You have prevention. you have automatic rules for success, creating friction, putting in guardrails, and then shifting your perspective. So I'd love for you to tap in on a couple of these. Yeah, my two favorites are sort of automatic rules for success and then shifting your perspective. And let me tie that into like, we've been taught our whole life to follow rules. Here's the speed limit you follow it. Here's the tax code. You follow it. You break the rules and you suffer the consequences. And we've been taught so well to follow rules that they actually

Starting point is 00:20:20 just work as the default. We don't consciously follow the rules. We just follow them. We learn the rule and that our brain sort of like just follows along with it. We don't even negotiate. And this is a crazy idea when you think about it because what we've never done is think about, well, how can I use these rules to my advantage? How can I create my own set of rules that my brain is going to follow independent of the situation, independent of the context, that's going to allow me to turn my desired behavior into my default behavior. And so, like, some of the rules that I have are like, this month aside, it's on pause for this month, but no meetings before 12. And I work out every day. And one of the, the workout every day, one, has changed so many people's

Starting point is 00:21:03 lives. And the reason it changes your life is because it, most people, I assume, are like me. I was trying to work out like three days a week. And I would wake up and I'd be like, you know, I'm really tired today. I'm really busy today. And I would start negotiating with my It's like, oh, I'll do extra tomorrow. I'm not going to work out today, but I'll lie to myself and tell myself that I'll do extra tomorrow. And that's all it was. It was a lie. And why am I negotiating with myself over something that I want to do? And so I just changed this around to like, I'm going to work out every day. I'm going to change the scope and duration because when I wake up, my conversation isn't, am I going to work out today? Am I going to sweat today? It's when

Starting point is 00:21:39 am I going to fit this in and how much time do I have. So I might go to the gym and just do a set of squats and then leave. I might just go for a quick run and then that's the end of it. Or I might go for 60 or 90 minutes depending on what's going on in the day. The negotiation with myself has changed from should I do this today to how much am I going to do today? And that allows for a powerful momentum and inertia and consistency that sort of works to my advantage later on in life. You can think about other automatic rules like investing in an index fund every month or I stopped drinking at nine. It's my rule. A friend of mine created a rule. A rule around not eating dessert. He was sort of like trying to eat healthier. But every time you try to

Starting point is 00:22:19 eat healthier, he didn't want to be on a diet. He's just like, I'm trying to eat healthier. But he goes to a restaurant. He's out with his colleagues. They're celebrating. They're like, here, we're having dessert. We're having all of this stuff. And you need to celebrate with us. And it's a willpower choice at that point. And everybody loses the battle with willpower eventually. You are not that strong. You're not stronger than your environment. You are temporarily. And you might deceive yourself into thinking you're stronger than your environment, but you're not. So you have to create an artificial environment in your head that circumvent all of these choices. So you don't even make a choice. You just follow your rule. And the idea for rules came to me from Daniel Conman. I was in his

Starting point is 00:22:57 penthouse. He answered the phone. And I remember hearing him say, you know, my rule is I don't say yes on the phone. And when he hung up, I was like, tell me more about this. And he's like, you know, I found I'm a pleaser. And I'm saying yes to things I don't want to do because I don't want to disappoint the person on the other end of the line. So I tell them my rule is I don't say yes on the phone. I reply back to more via email. And I was like, well, what changed? And he's like, well, I used to say yes, like 80% of the time. And now I say yes, like 10% of the time. And I'm like, that is so powerful. Another really interesting point on that is the social pressure when it comes to making decisions. People tend to not question rules, but they will question your decisions. So if you tell someone,

Starting point is 00:23:41 hey, I'm not going to have a drink tonight, they'll like, you know, maybe attack you a little bit. Maybe it can give you a hard time. But if you say, you know, I don't drink on Friday nights or I don't drink, period, then they'll just be like, okay, like this is enough for negotiation. Yeah, because it's not a willpower choice. When it's a willpower choice, they're going to push back. But it's the same reason you don't drive down the highway going like, why is the speed limit 70? It should be 75. You know, you just don't think about it because that's the rule. Are there any rules that come to mind when it comes to investment decisions? Or is that something you've thought about when it comes to this idea of having rules in place?

Starting point is 00:24:18 Sort of. I mean, I guess it really depends on what you mean by investment decisions, right? I think of a lot of investing as positioning in terms of like, can the company survive across time? Because one of the biggest lessons from history that everybody seems to forget is that things fluctuate. Interest rates fluctuate, environments fluctuate, access to capital fluctuates. And if you look back at most of the greats in history, the people that we would think of who have built great businesses, they're always playing offense in periods of panic or uncertainty. So they're always well positioned to thrive when things are good and thrive when things are bad.

Starting point is 00:25:00 A great example of that in plain sight is sort of Berkshire Hathaway, right? there's $150 billion on the balance sheet and cash. So the stock market goes up, he wins. Stock market stays the same, he wins. Stock market tanks, he wins. Interest rates go up, he wins. Interest rates go down, he wins. He just wins in every scenario.

Starting point is 00:25:21 And one of the most underappreciated facts to sort of clear thinking and why people get consistently better results than other people is they put themselves in a better position to be successful, long before the moment of decision. And if you'll indulge me for a second, I'll give you an example of this and how I applied it to parenting a few weeks ago with one of my kids. And he came home with one of his exams and he got a really bad grade. And he hands it to me and he's like, I did my best. And he walks by and I look at the grade and I'm like, oh my God, don't say anything in this moment because I know from playing sports when I was a kid playing football that like most of my friends ended up quitting

Starting point is 00:26:00 sports in the car ride on the way home after the game, and it was always the parents. So I was like, I'm not going to say anything. I wait. The emotions sort of like calm down. And then we talk about it. And I'm like, well, you said you did your best. Like, what does that mean? And he's like, well, at 10 a.m. when I sat down for my test, I'm like, yeah, walk me through it. Like, I want to know all the details here. It's going to sound silly, but like indulge me. And he's like, I read every question. I figured out which questions were worth the most. Like, he followed his little procedure to take on tests. And he did the best of his ability. And I'm like, That's great. So you did the best in the moment of the decision, but let's rewind here. Did you get

Starting point is 00:26:36 a good night's sleep the night before? No. Did you eat a healthy breakfast? No, because I slept in. Why were you up late? Well, I was cramming. I was trying to predict what was on the test because I didn't want to spend the time studying all the material. Did you get into a fight with your brother? I did because I was really aggravated in the morning. So, like, did you study in the three days before? or did you try only to cram? Well, I tried only to cram. So, yeah, you did your best in that moment, but you put yourself in a poor position

Starting point is 00:27:04 by not doing these things that are all within your control before the moment of decision. And so we think about decisions as being rational in that moment, but a lot of rationality is also just putting yourself in a position. You can't predict the future. Things are going to change. You don't know when they're going to change. Nobody's going to give you a warning,

Starting point is 00:27:26 saying, hey, go home. In two weeks, COVID's coming. No, it's just the world shuts down and you have to deal with it as you are. Same with emotional crisis or relationship crisis. All of these things just happen without warning. And they always just sort of like hit you at the worst possible time. And so that's why it's so important to think about your positioning on a daily basis. And that positioning can be as simple as sort of like sleep, working out, eating healthy, doing the basic things within your control to be able to withstand and reduce your emotional forces at the same time. But it can also be investing in your relationship and sort of building that with your partner and your spouse. Why is that important? Because when the inevitable crisis hits,

Starting point is 00:28:10 when the inevitable argument hits, if you have a solid foundation, you're going to be a lot better off. A friend of mine, Peter Kaufman mentioned, you know, there's a patch of grass between you and your partner. And every time you invest in your relationship and you cuddle and you connect and you spend time together and you do things that are fun, you're watering that grass. And if you don't do those things, the grass dries out. And any little spark will set that on fire when you have dry grass. But if you have wet grass, you can basically pour fire on it and it's not going to start. And I thought that was like such a powerful way to frame this. A minute ago, you talked about how we can't rely on discipline. And I wanted to tie this into

Starting point is 00:28:54 managing our environment here. You talked about how many of our habits, these are very hard-coded into us. And many of those hardwirings, they come from our environment and the people we surround ourselves with. And in your book, you wrote, many of the algorithms you're running have been programmed into you by evolution, culture, ritual, your parents, and your community. Some of these algorithms help move you closer to what you want. Others help you move further away. You unconsciously adopt the habits of the people you spend time with, and those people make it easier or harder for you to achieve progress

Starting point is 00:29:28 toward what you want to achieve. So this idea of thinking that we can be disciplined, it's like, oh, it's okay if I hang out with these group of people. But over time, we just unconsciously pick up the habits, pick up the thought processes of these people. And it just points to really, we need to be mindful of who we surround ourselves with because our defaults are essentially going to drift or just go astray into the direction we maybe don't want it to if we don't hang out with the right people.

Starting point is 00:29:59 Yeah, it's not only who you hang out with. You can think of your environment in multiple ways. One of your environment is sort of your physical environment, which would include the people you hang out with. But another aspect to your environment that's really important to everybody listening to this podcast is sort of start at the top and the inflow and the filter. Who am I listening to? Who am I reading online? I might not know these people, but I'm spending a lot of time consuming their information. And those thoughts are going to dictate. The thoughts that I led in my head are going to

Starting point is 00:30:27 dictate my future thoughts. They're going to impact me in a way that I can't really perceive and I can't really know, just the same way that your friends impact you. It doesn't happen all at once. It's gradual, gradual. It's gradual, gradual. If you are an ambitious person and your three closest friends are super lazy, you will become lazy. It's just sort of inevitable. You think you can't. You can use willpower. You can fight it for so long, but over time it's just going to change. Just like if your three closest friends smoke, you will eventually start to smoke. It's just sort of, it's such a powerful force, but we don't think of environment. But we can also, part of what we're doing with automatic rules for success is we're

Starting point is 00:31:07 creating an artificial environment where we can thrive and turn our desired behavior into our default behavior. You can do that with people too, where you're hanging around people that you want to learn from, that maybe more driven from you if you want to work harder. You hang around with people who work hard. Take jobs where you're required to work hard and you're going to start working harder. I wanted to tap in more to decision making here. When I think about, you know, this is an investing show. Most new investors, they associate a good investment with something that goes up in price and they associate a bad investment with that which goes down in price. And I always think of the example of poker when I think about this, you know, expert poker players know that you need

Starting point is 00:31:50 to learn to differentiate a great decision from a great outcome. You know, you could make it the best decision, but it could just totally turn against you. And, you know, you made the right decision, but you just have to accept the fact that eventually things just don't go your way. And we don't live in a world where there's absolute certainty, especially when it comes to investing. So I'd like for you to talk more about how we should distinguish between, you know, the process of making a decision and separating that from the ultimate outcome that ends up happening. Yeah, so a few thoughts there. One, if you're wrong on any individual decision, like you get a bad outcome, not that you're

Starting point is 00:32:28 wrong, but you get a bad outcome on any individual decision, that doesn't mean you were wrong, If the body of work collectively indicates the same pattern, then there's something wrong with the way you're making the decision, the way you see the world, your perception on it, you're making the mistake. So one decision is a signal, but like a body of work is like, that's a really strong signal that something's wrong. You can't just look at the outcomes, but what you can do is create a decision journal for what you knew at the time you made the decision.

Starting point is 00:33:03 And more importantly, what you consider relevant and why. Going back to what we talked about earlier with the learning loop, you sort of articulate the situation and then you reflect on it and that reflection draws out a conclusion, but you're writing it out and you write it out in pen. Don't use a computer template for this because you'll read it later and convince yourself that somebody else wrote it or somebody else edited it. You need to see your handwriting. So it's like, what's the situation?

Starting point is 00:33:30 What do you think is going to happen? why, what are the odds of it happening? And then when you go back and you look at the outcome, well, here's what I actually thought was relevant. Here's what I thought was going to be the determining factor. More often than not, a lot of times what we see is that we got the answer right, but not for the reasons we articulated. And is that luck?

Starting point is 00:33:52 There's an element of that, or maybe your body's feeling something that you can't quite articulate. But what you're really trying to do is calibrate, where do I make good decisions, where to make bad decisions, how do I get better at this? And I'm not just looking at the outcome. Now I'm starting to evaluate the process I use to come up with that outcome. So if I'm consistently missing on, you know, I'm overconfident or I'm consistently missing on the range of outcomes, well, now I can incorporate that into my process. So I have a better process for making decisions. You kind of touched on this here. It's really hard to differentiate between a good process and a good

Starting point is 00:34:26 decision and something that just happened to be luck. So could you talk more about how we can distinguish between a good process and good decisions and maybe just getting lucky? Yeah, well, it sort of depends on the type of decision you're making too, right? If you think in terms of like Jeff Bezos and he says one way doors and two way doors, if you have a two way door, you really don't want to think too much about your decision. The cost of failure is really low, so the biggest cost is going slow. Whereas with a one-way door, the cost of failure is really high. So the biggest problem is, you know, you get it wrong. So you want to go slow. And I think that those two processes lend them, and it's a continuum. You're sort of like, it's not quite binary either way.

Starting point is 00:35:08 There's very few things that are completely a one-way door. And there's very few things that have sort of no cost to undo. But when you're looking at those decisions, you want to have a different process around those decisions. And so the one-way doors, as you get towards that end of the continuum, you want to have a more rigorous process around that than the one-way door or the two-way door when you allow people to exercise judgment and go really fast. And so it comes down to, hey, you know, on this individual decision, you were wrong, we evaluated it. It didn't come out the way you wanted it to, but that doesn't mean that you made the bad decision. It means we got the bad outcome. And I think that that's really

Starting point is 00:35:48 important to figure out, but you have to do the work to figure that out. And it's not always easy to do that work. And again, one decision is a bad signal, but a body of decisions collectively where you're making repeated decisions in a very similar environment, you're getting really solid feedback that there's something wrong with the process. So I would look to change the process. And you want to incorporate this, right? Like if organizations tend to be wrong in one way, you want to add that to the process. If something is going into the process, it's not valuable. This is an important component too. You want to remove it from the process because you don't want to have too much weight to the process. You want to have just enough to get the best outcomes possible.

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Starting point is 00:39:34 the investment material before investing, including objectives, risks, charges, and expenses. This and other information can be found in the income funds prospectus at fundrise.com slash income. This is a paid advertisement. All right. Back to the show. I like how you also in the book, you talk about what really matters. You know, before we figure out what sort of decisions we should be making, we need to

Starting point is 00:39:59 understand what's important to us and what is going to lead to a happy and fulfilling life and a life that we truly want. so we know what it is we're actually working towards. As I was reading your book, I was actually reminded each summer with my family, I go on vacation to the Ozarks and I see all these nice lakehouses and I just think how wonderful it would be if I saved up some money and go by one of these wonderful lakehouses and how that would make me so much happier. And another point in your book I deeply resonated with was you talked about how when you first

Starting point is 00:40:30 joined the workforce, you naturally just push for the promotion, push for the raise and become so fixated on this belief. that that is going to bring you that happiness and fulfillment. And the problem with all this is that it sort of ties into the hedonic treadmill where we're always pushing for more, more, more. And we don't ever become satisfied with what it is that we have in that moment. And much of our intuition, it might tell us that these things are going to make us happy. But if you really zoom out and you look at the big picture, it doesn't really matter all

Starting point is 00:41:01 that much if you got that promotion or you had that lakehouse. So could you talk more about this idea? of what truly matters to us and what's going to truly lead to a more happy and more fulfilling life. Yeah, there's a big difference between getting what you want and wanting what matters. And I think we're culturally influenced and pressured into thinking something matters when if we step back and pause, it doesn't matter to us. And what that means is we end up playing life by other people's scoreboard instead of our own scoreboard. And we know this because if you read Carl Pilmer, work or anybody who you go to a retirement home or you go to an old age home and you talk to people,

Starting point is 00:41:42 you'll quickly realize that most of what we think matters doesn't really matter when we get to the end of our life, but how can we turn their hindsight into our foresight? And a great example of this is sort of like, who do we know that got everything they wanted in life, everything that they thought they wanted? And, you know, what are we taught? We're taught we want money, we want power, we want control. We want to be well known. We want all these things. Well, there's a book that was written a long time ago called A Christmas Carol. And what did we know about Everneeder Scrooge? Well, he got all of these things, right?

Starting point is 00:42:15 Money, power, success, most well-known person in his community. And what did he want at the end? He just wanted a do-over because the way that he achieved those things was mutually exclusive from what really matters in life and what's meaningful in life. And I think that there's a lesson there for all of us. and there's a reason that book is still published and it still resonates with us. And so often we just wake up too late and we realize we've played somebody else's game and it's too late for us to change it.

Starting point is 00:42:44 And the important thing is just being conscious about what matters to you and what doesn't. And that's going to change throughout your life. That's not to say what you want at 19 or 20 is going to be the same as what you want at 25 or 30. And what you want at 30 is not going to be the same as what you want at 60. The point is that you're working towards your own goals and you're playing towards your own scoreboard and you're not letting somebody else tell you what the scoreboard is. You also talked in your book about the happiness study and they interviewed all these people who were later on in their lives. And one respondent said, in my 89 years, I've learned that happiness

Starting point is 00:43:19 is a choice and not a condition. And then later you wrote, happiness requires a conscious shift in our outlook in which one chooses daily optimism over pessimism, hope over despair. And here I realize that happiness is largely, it's something that's just internal. It's not necessarily dependent on these external factors, as you mentioned, and, you know, thinking about the digits in our bank account or something else external. And once we have these basics, we can really start to appreciate them and be happy. And it just ties into this piece of gratitude, which I also think is so, so important. Happiness is really a mindset.

Starting point is 00:43:55 And if it's a mindset, it's a choice. You're choosing what you look at. you're choosing what to value. You're choosing where to focus your attention. And in any given moment, in any ordinary moment, you can choose to focus on all these negative things. You can choose to focus on all the negative traits about people or situations or you can choose to focus on the positives. That doesn't mean you have to be somebody's best friend, but if I think negative things about you, it's going to affect my relationship with you. And I'm only going to see those negative things. and I'm not going to see all the good and the joy that maybe you offer to your partner or your

Starting point is 00:44:31 kids or all these other aspects of your life because I've written you off. And when I've written you off in my head, I stop even listening to the information that you provide. So now I got a big blind spot because you could be coming to me one day and say, Shane, you're about to go off the rails here. I'm going to save you from this, but I'd be like, ah, Clay, like, I don't like him. You know, and then you discount this information in a way that you shouldn't. And so I do think happiness is a choice And I do think that we prefer that it wasn't a choice because then we can blame somebody else and we're a victim. And I just don't buy all that. I think that, you know, we get one life and it's our choice to be happy or not.

Starting point is 00:45:06 And that means what you focus on and the mindset and the attitude you approach things with. And those are all things you control. When I look at you, Shane, I just see someone that has been pretty successful to say the least. yet you've been extremely successful in building out your blog and your newsletter, your podcast. You have a holding company that's very successful. And I'd love to get your insights on, you know, when you look at your own life and what's most important to you, what are some of the top things that, you know, make it to the top of your list? Because there's all these things, I'm sure you're sort of grappling with in your own life and all these decisions you have to make, all these sort of

Starting point is 00:45:43 balances you need to try and find. So what are some of the things that make the top of your list on what's most important? Oh, that's easy. It's just kids and, you know, my family and freedom. And freedom means that it's not just free to say what I want, live in a country where I can speak my mind and have a different opinion. It's freedom of time and freedom of obligation, the freedom to say no to somebody else. And that requires financial independence in my mind. But that's just one part of sort of wealth to me is not, you know, there's a difference between money and wealth. And a lot of people want money. I want, wealth and wealth incorporates relationships and it incorporates health and it incorporates all the things

Starting point is 00:46:24 that sort of bring me joy and that's very different than just money. And so I don't overly index on the making a lot of money. I want to do good things with good people and I have a long runway. So I just want to keep doing that. And I think that one of the advantages for me of not taking outside money or other investors is that I just don't need, there's no rush. I have a saying that a lack of patience changes the outcome. And I feel like everybody's just in a hurry to do things. And, you know, I got another 60 or 70 years of this if I want to keep going. And that's a long runway. And I love what I do. And I'm so happy and blessed that I'm able to do it reasonably successfully. And with really good people, people I want to be friends with people I trust, people I've worked with for a long time.

Starting point is 00:47:09 I love working with people for a long time because you have high trust. You can just instantly, like when I get documents from people, people I've worked with for a long time. I'm not looking for how are they going to screw me over. What legal clause do I really need to like focus on here? I'm like, I can just be excited and I can help people and amplify them. And then we can use our platform to help people too. We have 600,000 people sort of reading our weekly newsletter and our podcast reaches hundreds of thousands of people. And I just love being able to share some of these experiences with other people. And yeah, it's just really fun, man. Like, I wake up every day and I'm just so happy to go to work and I do the things that I want to do. We have a great team here at Farnham Street. Like, it's really important to me to

Starting point is 00:47:54 work with good people and to do things together. And sometimes that means going slower, but I think it means going farther in the end. Is there anything that any sort of practices, whether it be journaling or sort of reviewing, kind of reviewing the big picture, is there anything that comes to mind that kind of keeps you going in that direction that you want to go and make sure you're not straightened too far away. Yeah, I mean, I do an annual review with myself, and I do sort of like a quarterly check-in. The quarterly check-in is, I'm just asking myself, like, how am I spending my time? And then I look at my calendar because I don't want to just ask myself, and I put a lot of things in my calendar. So, like, am I focused on, I'm saying these

Starting point is 00:48:34 things are my priority. And I have this saying, don't tell me your priorities, show me your calendar. And so I have these things in my mind that I say are my priorities. And does that line up with my calendar. And, you know, I said my kids are important to me. So one of the most important things for me is I'm home every day when they get home from school. And they're in high school. One's in high school. One is still in middle school. And a lot of people are like, oh, they can just, they can get their own snack and start their own homework. And I'm like 100%. They can. I don't need to be there. They can watch themselves. They can easily get together a snack. That's not the point of me being there. The point of me being there is because I want to be there. And if they have a bad day, I want them to be able to

Starting point is 00:49:13 talk to me. And if they don't want to talk to me, that's okay, but they know that I'm there. And it's really important for me. They just know that I'm there for them. And I think I've missed like two days in the past couple years where I haven't been home from school and that's happened. And so like, I just think like, does what I say that I want line up with what I want or what I'm doing? And then do I still want the things that I said I want? And this will all change, right? They move out. I'm going to have a different relationship with them. I don't need to be home at 330 anymore. What does that enable me to do that I haven't done before? But until then, man, I just, I don't want to regret this. And I think so often I watched parents when I worked at the

Starting point is 00:49:53 intelligence agency and their kids got to these teenage years. And then they started parenting, sort of less and less. And it's not about parenting because I'm more of a coach now than a parent. But they just stop. They're like, oh, I'm going to work harder. Now's the time to focus on my career. And I just watched how that relationship affected their kids. And all of a sudden it goes from, I'm going to be late getting home to you eat dinner by yourself, to I'm going to show up after dinner. And then all of a sudden it's like, I don't know anything about my kids. I don't have a good relationship with them.

Starting point is 00:50:22 And I just don't want to regret all this time. I don't want to be in my, you know, later on in life go, oh, I wish I could have a do-over on that because we don't get a do-over on this. And I just think, yeah, I get a lot of joy out of that. I'm quite boring, actually, I think, when you think about it. I think one of the big takeaways from media book is. is implementing more rules. You mentioned the quote, you know, don't tell me your priorities, show me your calendar. I think this is certainly something I can work on myself. I'm always willing to,

Starting point is 00:50:52 you know, send someone a link to hop on my calendar and chat with me and, you know, someone kind of has priority over my calendar when I send them that. I notice how some people I happen to see their calendar on their phone, they're pulling up their schedule or whatever. And I see they've got time scheduled for like their workouts or time scheduled for like they're doing something on their own. they're not meeting someone else. They're putting time on their calendar for themselves. I think that's a really important rule that I think just looking at some people, it just seems to be something that works really well. Yeah, totally. I mean, I don't usually book meetings before 12 for that reason. I never want to have to find time to do something important to me. So I just block the time. And that's when I do

Starting point is 00:51:32 something important to me. And it doesn't matter if I'm walking the kids to school or I'm sleeping in or I'm going for a workout or I'm working on a book or I'm, you know, thinking or researching a guest. It's whatever is most important to me, I want to have time built into my schedule to do that. All the other stuff, all these sort of like urgent, responsive tasks, I can do that in the afternoon. And when you do it in the afternoon, you actually tend to be a lot more ruthlessly efficient about them than when you do them in the morning. So they take a lot less time. In the morning, you know, you're sort of, oh, how's it going?

Starting point is 00:52:05 and, you know, like, what could be a five-minute conversation with Clay, turns into like 30-minute conversation with Clay. And I've just, you know, I've wasted 25 minutes in a way. But if I do that conversation in the afternoon, it's like a five-minute conversation. Well, now I can do five of those conversations in the same amount of time that I did one, especially when it comes to getting stuff done. I just don't think we're conscious enough about how we spend our time. And that's, again, it comes back to, there's a difference between getting what you want

Starting point is 00:52:31 and wanting what's worth wanting. And it's really important to think about both of those things. I think another big challenge that people struggle with me included is that there's oftentimes not just one thing we want. We value our health. We value our work, career. We value our friends. We value our family.

Starting point is 00:52:50 And it's just sort of this balancing act of constantly balancing, you know, I want to spend more time with these people, but I also want to get these other things done as well. Yeah. I don't think in terms of balance. I think that's a really flawed way to think about it for me personally, and that's not to critique anybody who thinks of it that way. I used to think of it that way, but then I always felt out of balance. And I was like, what is wrong with me? And I realized there's nothing wrong with me.

Starting point is 00:53:16 Maybe there's something wrong with thinking of things imbalance. I don't need to balance work and my relationship. Think of it as a mosaic and the pieces are all the same. And the pieces can shrink or expand depending on what's going on in your life. If your partner's having a health crisis, you want to be there for them. that's going to be a huge portion of your mosaic, but it can't really eliminate all the other portions. And so you can never go to zero in any of the pieces, but the pieces sort of like shrink and expand to what's going on in life.

Starting point is 00:53:43 Sometimes the kids are going to be more hands-on and require more attention. And work is going to shrink. Sometimes work, you get a big project or a big book coming out or something like that. It's going to expand. But I'm not trying to balance these things at all points in time because I'm always failing if I'm trying to balance. And that implies like taking a little bit from here and there. And no, I think of it in terms of shrinking and expanding.

Starting point is 00:54:04 And I even talk to the kids about this, which is like, hey, for the next few months, work is going to be a little bit busier than it normally is. That sort of happens. And it's important that they see that happening, that they know that it'll go back to normal at the end. And it just changes sort of like how you think about things and approach things. But the real question is, what's in my mosaic? What are those pieces?

Starting point is 00:54:26 You have relationship. You have community. You have health, you have work, you have all of these different pieces, and you have to determine your own pieces. And what's important to you, for some people, it's religion, for other people it's something different. But all of those pieces need to be there for you to live a meaningful life. And I think that if we don't think about them, and what tends to happen when we get busy

Starting point is 00:54:46 is we start dropping some of these important things for life in the, and it's not balance. It's just like we never think of, oh, I'm going to skip my workout. Okay, well, that's fine. You skip it one day. It doesn't matter. but you skip it for weeks, well, now all of a sudden you're in less health. If you stop sleeping to get more work done, well, you can do that for a day, but now it's going to affect your relationship. It affects your mood. It affects your decision. Has all these downstream effects that we don't

Starting point is 00:55:10 think about coming back to positioning. We just put ourselves in a bad position. So I never let them all go to zero. And I never want to sort of like, oh, sleep is so foundational. So it was working out. So is eating healthy. These are the foundations that have massive downstream effects on not only my decision making, but my happiness. And so I want to make sure I get those right and I get them nine times out of ten. I don't have to be perfect with them, but I want to be really good with them. As if having this newsletter blog and podcast wasn't enough, you also run a holding company where you go out and you're open to purchasing great businesses or wonderful businesses, whatever you want to call them. So how does this sort of fit in to what matters for you?

Starting point is 00:55:54 I want to work with great people who are. doing amazing things and want a really good partner. And so I set up Cyrus as just a holding company to partner with great businesses for a long period of time. I never want an exit. So if we write a check, I'm never, you know, there's no LPs that we're not concerned about when we get our money back. We just want to partner with businesses that have a long runway with people we trust and respect and admire and people who are fanatical about what they're doing, whether that's, we're on the cap table as a minority investor or we purchase the entire business from them. partner with them or we haven't done a replacement or anything yet of a CEO. But like,

Starting point is 00:56:31 we're just really looking for good opportunities of people who have a long runway, passionate about what they do, fanatical about what they do, and just, yeah. And then also looking into your background, you're a board member of Tiny, which went public this year through its merger with We Commerce. And I found this to be quite interesting because we interviewed Andrew Wilkinson earlier this year. And it seems to be, you know, it seems somewhat counterintuitive where you have this holding company with Cyrus and then you're on the board of Tiny. So how does that sort of interplay and what led you to being on their board? So we bought a company called Pixel Union a long time ago. I think it was like, I'm going to guess, 2017, 2018. And Andrew had started that company earlier and

Starting point is 00:57:19 sold it to private equity. And then a group of investors, including Bill Ackman and Howard Marks and myself and Andrew, we bought that company back. And then we took it public during COVID. And we did a reverse takeover on the Toronto Stock Exchange. And I became a board member at that point in time. The company changed the same from Pixel Union to eCommerce. And then in January of this year, WeCommerce subsequently purchased, I guess, tiny, which was bigger than we were. And so now we have Tiny, which is this huge sort of holding company run by Andrew Wilkinson and Chris Sparling. And Cyrus is sort of a different entity, right? Cyrus is private and not public.

Starting point is 00:58:01 And so not exposed to sort of some of that stuff or those pressures and different in the way that I control Cyrus. And I don't sort of control Tiny. I'm just on the board and trying to do the best I can and help us make the best decisions possible going into the future. Awesome. Well, Shane, this is going to be a conversation I'll look back on and probably listen back to a few times. And I'm excited to have this one go out. It's quite an honor having you on the show. Before we close it out, I want to give you a handoff to where the audience can learn more about you and pick up the book.

Starting point is 00:58:33 I appreciate that. So if you just go to any bookstore, you should be able to get it. It's called Clear Thinking, Turning Ordinary Moments into Extraordinary Outcomes. You can find out more. Get a free chapter at fs. blog, or you can Google Shane Parrish or listen to the Knowledge Project. There's lots of ways to find me. But I'd love to hear from you.

Starting point is 00:58:51 One of the things that I've really enjoyed when I sent out books to friends for pre-reading before it came out was they would take a picture of a page or send me back just a note with the subject line saying this page really impacted me. So if you want to send me an email at shane at fs.blog, I'll read everything. I don't promise to reply. But tell me what page really impacted you and change your mind about something. I'd love to know. Wonderful. I can attest that there's a lot of pages that'll definitely make you think. So thanks again, Shane. This is great. Thanks a lot.

Starting point is 00:59:21 Thank you for listening to TIP. Make sure to subscribe to millennial investing by the Investors Podcast Network and learn how to achieve financial independence. To access our show notes, transcripts or courses, go to theinvestorspodcast.com. This show is for entertainment purposes only. Before making any decision consult a professional, this show is copyrighted by the Investors Podcast Network. Written permission must be granted before syndication or rebroadcasting.

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We Study Billionaires - The Investor’s Podcast Network - TIP580: Clear Thinking w/ Shane Parrish

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