251. Clear Thinking with Shane Parrish (Part 1)

Ladies and gentlemen, today we have the distinct privilege of welcoming a true luminary in the world of clear thinking and continuous learning. Our guest is none other than. Shane Parrish is the mastermind behind the widely acclaimed Farnham street, which itself is a platform dedicated to mastering the best of what other people already have figured out. But it's not just him. As a thought leader, he's like a navigator in the vast ocean of knowledge, helping us to try and clear steer of the cognitive errors of our lives. His contribution is enormous but also amazing with his new book, Clear Thinking. It's like a guiding light to people who are trying to be smarter in the world. So his journey is fascinating. Even from his early days where he was experiencing challenges and the opportunities of frequent relocations as a child to his thought provoking career transitions, Shane's life is a testament to the power of curiosity and lifelong learning. At Farnham Street, Shane doesn't just share knowledge, he cultivates, let's say, worldly wisdom. He challenges us to think deeper, question our biases and embrace the complexities of this world. Shane, welcome to the podcast.

Well, thanks for the incredibly generous introduction, Craig.

Well, it's deserved. And I want to just dig into some of this journey. Let's start with your early years. You were, I think maybe 8 years old, 9. I don't know, you'll correct me. And school was not so enjoyable. But then you had a moment in the library where you came across a book. Is it is the Watch Stop Gang? Am I saying that right?

The Stopwatch Gang.

Tell us about what that is and why it mattered so much.

Yeah, so, I mean, I, I, you know, I can't speak to other people's childhoods, but my childhood was a bit rough, especially when it came to school and academics and for whatever reason, I just didn't fit in a classroom and I was bored and reasonably intelligent. So I would start getting into mischief over and over again. Maybe it's a cry for attention, who knows? I mean, those are all questions like.

What kind of mischief would you get into?

Reorganizing books, vandalism, deleting stuff from computers. Just petty mischief that you get into when you're sort of 13. Going out on my dirt bike with my friends and, you know, so in grade seven, I had skipped school for seven weeks and then I decided to go live with my.

Hold on, you skipped school for seven weeks?

Yeah, this is back when, you know, you used to have those answering machines that still had cassettes in them. So I used to erase the school message every day. I mean, I set it up right, like when I, when I said reasonably intelligent, I was like, oh, we're going to Florida for a month, like we'll be back in a bit. And you know, this is like the teachers didn't really ask questions back then. And you know, so they started calling when the month was up and they call every day and I just delete the message. And you know, I would go outside and pretend to walk to school and my parents would leave for work and then I go back to my tree house and I'd eat eggs. I'd make myself eggs during the day and that's sort of what I would live off of. And they wondered where all the eggs were. But I was like, oh, when I get home from school, I was just eating all these eggs. And then eventually, you know, the school principal I think came and knocked on my door one night and I was like, oh, this gig is up. And I thought it was funny in terms of I just didn't want to go to school, I didn't like the classroom. And as a condition of sort of not being expelled, I had to go see a child psychologist. And she's like, you know, there's nothing wrong with him, he's just bored, which was good. And then I decided to go live with my biological father in grade eight because I thought a fresh start might offer different advantages. And you know, it didn't end up working out that way. And so I fell in with the wrong crowd. In grade eight, Grade seven, I was sort of on my own getting in trouble. In grade 8 I was encour by the people I was hanging around to get into trouble. And I remember it was increasingly getting worse and worse. Right. Like I was on a path to really no good. And you know, I hadn't crossed that line. As if there's a line, but I hadn't really crossed the line. And then you know, one night, well, during the day we had went to the library and we had to do this book report and I hate book reports. I hated school. I hated everything about school. I hated somebody telling me what to read. I hated somebody telling me what to do. I hated somebody having a subjective opinion in about my thoughts and whether they were right or not. And you know, just a really troubled childhood in that sense. Anyways, so I ended up in this true crime section of my Create 8 library, which had two books. One was called the Stopwatch Gang. And I was like, oh, this one looks interesting. I just randomly picked it up off the shelf, started Reading it, reading the first page. And you know, it's about these bank robbers. I was like, oh my God, this is my kind of book. This is awesome. So I get home that night and I start reading the book. And you know, I get halfway through it. And then the next night I'm reading it again because I can't put it down. I'm like, oh man, how did these guys work? And I start trying to figure out, like, how do they pull this off and what does it take? How do the cops catch them? And it became this real life sort of, I don't know, it was a true story and it was so captivating and I was so into it. And my friend showed up at my door on the second night and I'm like one chapter away from finishing. And they're like, come on, they're on their dirt bikes. We live in the middle of nowhere. And I was like, no, I'm not feeling well. Well, I'm not coming out tonight. But I really just wanted to read this last chapter. And I knew if I went out, I wasn't going to read that last chapter. And I was just so pulled into this book. Anyway, they went out that night, they broke into somebody's house, which we had never done before. And I would have been with them. I doubt I would have gone in, but I definitely would have been there. And I'll skip over the. The bad part, but it happened to be a cops house and their lives changed.

Sorry, what do you mean? What do you mean you skipped over the. The bad part? This feels like kind of the bad thing.

But yeah, I mean, they get caught, there's a lot of trouble, a lot of drama. The cop came home, saw flashlights in his house, called it in, and, you know, went in and their lives changed. They never returned to school. And so, you know, in the blink of an eye, through sheer luck, I ended up staying at home. And then, you know, I went to the school the next day and I'm like, whoa, where are they? What happened? And, you know, sort of like went to their house and I got no answer. And then, you know, eventually it just came out that they're not coming back to school this year. And then it came out that they sort of, you know, went to juvenile detention or, you know, whatever the consequences were for, for them at the time. And I just got scared straight. I don't know if that term makes sense to everybody, but I was like, man, I could have been there. And this was a coin flip, 50% like, you know, I Could have gone either way. And I felt bad because maybe it had been there. I could have warned them and they would have gotten less trouble or, you know, and alternatively I also was like, O man, my life just flashed before my eyes in a very different way because of this book, right. And I was pulled into this world and that was this sort of thing.

Right.

And so after that I was never a problem in anything. I mean, I was mischievous a little bit, but like, not like I was before. And so in grade nine, I went back to living with my mom and my dad and you know, I found computers in grade nine and computers, my grades did not improve in school because I was sleeping in school most of the time. I would stay up all night playing on my computer, programming my computer, and then I would go in the next day and try to finagle my way through school. And yeah, it just definitely changed my path. And we all have these random moments where, you know, one choice and it's not even a choice, it could be luck, it could be thoughtful, it could be sort of conscious and. And you'd be just in a completely different situation than you are right now. And I'm cognizant of that. And sort of I escaped through this fiction, well, non fictional world in this case. And you know, that's how I survived the rest of grade eight. I just actually read books. Read books I wanted to read, not the books the school was telling me to read. My grades did not improve. I was a straight D student all the way until grade 10.

There's so many places to go with that, but. Well, one place to go is just. Is, how did you go from that description to being a spy for the Canadian government? I mean that's quite a shift. Other than there's something. There's like a golden thread through everything you've just shared, which is sort of kind of low key, nefarious, you know, like wanting to. I mean, that's seven weeks you're away from school. That's more than just, oh, I took off for a day. You know, there was strategy to that deception. And I don't mean to make more of it than it is either, but there's something there. So was that the theme that continued?

It's interesting. I've never thought of it that way. I mean, there's definitely an angle to people who think outside the box and think differently and have to look at a situation and see different things in that situation. And I get to work with a whole bunch of people like that who saw systems as Puzzles. And the puzzle was, how do we get what we want out of that system? And then can we arrange it so that it happens? And whether you wanted to skip school or do good in the world, it is a system that we operate in. And understanding the system we operate in, its limitations and its strengths can have certain advantages and disadvantages. Right. There's not all pros to it.

So you said that your grades changed when grade 10. What changed in grade 10? Do you know what changed?

Yeah, so I. I switched schools every year until grade 10. So grade 10 and 11 were the first two years I went to the school.

That's a lot. That's a lot of schools. That's a lot of disruption.

Yeah, it is. I knew in grade 10, I had moved from grade nine to grade 10, different provinces. And I knew in grade 10, I had a good shot at being in high school for three years together. And I decided, like, I'm good at making friends. I mean, you know, byproduct of. Of moving so often is I can walk up to people, I can talk to them, and, you know, I can fit in with almost anybody. I can fit in with the jocks. I can fit in with the nerds. And so I decided, you know, I was going to join a sports team, and that was a good way to meet people. So I show up for football practice on day one, and, you know, they're running around the field, and I'm like, this does not look like a lot of fun, but the guy's like, what do you want to do? And I'm like, well, that guy over there is, like, throwing football, and he doesn't look like to be working so hard. So I'm like, you know, I just point over there. I don't say anything. The guy's like, oh, you want to be a quarterback? And I'm like, yeah, yeah, that sounds good. I had never thrown a football on a team before or anything. You know, that first year was a bit of a disaster. I got the nickname third string because I definitely did not see the field the first year. And anyways, I ended up talking to somebody after practice who became my best friend in high school. And his father is actually. His father and my grade 11 English teacher are probably the two people more than anybody who in high school changed my trajectory for the positive. And I remember two distinct moments. One, in grade 10, it's sort of October, and I go over to my friend's house. His name was Scott, and I go over to his house, and his dad sort of pulls Me aside after dinner, because at dinner we were talking about university and what I wanted to be, and I was like, I don't even, you know, like, what is university? Like, I don't. That's not a word that we use in my house. I don't know what that means. It sounds expensive, right? Like, it sounds like it costs money, and, you know, we can't really afford that. You know, I'm just having this very different conversation. He pulls me aside, and I don't know if he remembers this, but he was a very stern and straightforward man and not somebody you wanted to be on the wrong side of. And he did this very tactfully, too. He waited for his son to, like, go to the bathroom, and he sort of like, nudges me outside, and he's like, look, I don't know where you come from. I don't know where you're going, but if you're not going to university, you're not hanging around my son.

Wow.

And I was like, I don't. I don't even know what university is. Like, you know, it sounds good, but he's like, I'll help you, but that has to be the path you're on, and that means good grade. And he, like, laid out pretty much like, what that means.

Wow.

And his son, you know, became my best friend. And it was okay to be smart all of a sudden, you know, when you're hanging around bad kids and you start hanging around good kids, you adopt the behaviors of the people you're around. And it was okay to do good in school. It wasn't uncool anymore. Wow. And so I ended up doing pretty decent in high school, I would say. I didn't do homework, so I got 0 out of 10 in most classes on homework, but I still got high 80s in my grade, so it was good. And I worked full time for most of high school to pay for university because, like, Mr. Corkery sort of instilled in me that if I want to go to university, that I would have to do that. And so I started working 30 hours a week, and I would close up the store. And, you know, that was my means of saving money so I could go to university. And then I wanted to take computer science because that's what I did every night. I love playing on computers. I love programming. I love that I could connect to other computers. And, you know, you can imagine all the mischief that I would get up to when I could connect to other computers and play around with things. Back in the 90s, right? Buck before that sort of got a bad name to it.

It's another extension of this theme that's come out of the conversation earlier. These inflection points. I mean, you're subscribing it to luck, or it could be luck, but, you know, the meeting of that particular friend, the conversation that his dad has with you, you know, but for the fear of God, go I, you know, like, how different life would have been even at that point without that intervention.

100%. And then there's another moment that probably actually got me my job, which, you know, it took three years to sort of play out. But first year university, I had to take a physics class, and I didn't have time to do the assignments and to put things in context. Each assignment was unique to each student. So no two students had the same assignment. There was 10 versions of question one, and each version of question one had different numbers. So no, no two assignments were exactly alike. And you had to log in and submit your results over telnet. For anybody who remembers that, what that is, you basically have to, like, enter the right answer and then go on to the next question. And, you know, these assignments took like, 20 hours to figure out they were for physics majors. They were not for computer science majors. This was like a serious physics class.

That is impressive.

All the kids in my class used to hire the same two tutors. And these tutors had a spreadsheet, and they basically looked at what version of the test you had, enter your numbers and spat out the results. People would take those results, and for 20 or 50 bucks or whatever it was at the time, they would be done their assignment in a matter of minutes. And I couldn't afford this tutor. And since nobody else had my question.

So by tutor, you don't really mean tutor. You mean just someone who did the work for them.

I'm using a very kind word in this situation. Yeah. And so I was like, oh, well, how do I solve this problem? So I remember spending a night on the computer, the physics website, the school's website, and I read every rule there was to read about submission of assignments and electronics, and nowhere did it say that I had to enter my numbers manually. So I wrote a little program, and this program guessed negative 100,000 to positive 100,000 in increments of 0.1, because that was the margin of error. And so I just ran this program at night, and I would wake up in the morning and I would have 100 on my assignment. It would just guess the. There was no limit to the number of guesses that you could have on this question. So it wouldn't even read the physics questions. It wouldn't even read my variables. It would just literally guess the answers. And anyways, come in in March, and he shows this little presentation, and on the bottom is your student number. So on the x axis is your student number. On the Y axis is number of guesses. And, you know, the average guess number of attempts per assignment was, I don't know, like 8 or 12. And then there's one student who broke the several times, and he's like, I would like to see the student in my office after the. After the class. And so I show up at it. Everybody's like, what the heck? And I was like, oh, this is like, oh, God, I'm probably in some sort of trouble. And so I show up at his office, and I'm like, hey, it's me, you know? And he's like, yeah, so I'm going to give you zero on your assignments. And I'm like, whoa, what do you mean, zero? Like, that doesn't make sense. And he's like, well, you violated the rules. And I was like, no, I have a copy of all the rules at home. And he pulls up his website and he shows me. And I was like, that is. That was not there. You just added that. Like, that's. That's not fair. Going forward, I won't do this. You know, I. I can't afford to do what all the other kids are doing. And I didn't rat anybody out, but I just said, like, I can't afford to do. Do whatever everybody else is doing. And I'm working 40 hours a week while trying to come to this class and, you know, basically like a sob story. And he didn't buy it. He gave me a zero on that. I ended up failing physics because he gave me a zero on my assignments. So, long story short, to bring this full circle to how I got my job, when I'm doing my interviews, they ended up talking to him. And he finds me in the hallway, and he says, I'm sorry, this is still coming back to bite you. You're probably not going to get your job. I had to be honest with them. And I just remember looking at him and I'm like, I'm really glad you were honest with them, because that's why I did get my job. I didn't violate any rules, and I thought outside the box about how to solve a problem. And that's what they. They want people to do at intelligence agencies. And you know, I thought that that was a good way to sort of bring that full circle, right where he taught me a really good lesson. And at the same time, that lesson came back to be a positive thing in the future.

How long were you working for the intelligence agency?

Can I just preface this with, like, I had the best job in the world, right? Like, I started two weeks before September 11th. I get to work with, oh, my goodness, some of the most insanely talented, unsung heroes in the world for 15 years, people who got no recognition for what they did, people who sacrificed countless hours, who spent more time at work than with their family, especially in the wake of September 11th. And insanely, insanely talented, amazing group of people who I still love to this day. And so I worked there about 15 years.

Can you give me just a tiny but concrete example of something someone did that makes you preface it like that?

No, not without going to jail. I don't want to walk any lines.

Here, you know, give me this sense then. Do you. So you mean people on the front lines of action. You don't mean the. Or do you Give me more. Something more.

I worked for the Canadian version of nsa, or if you're listening in the uk, gchq, you. And so we worked in concert with agencies around the world. The choices that we made through what we were doing affected our country and other countries and troops in theater. You know, I was never brave enough to sort of like, pick up a gun and be on the front lines. And I did have a huge sense of patriotism growing up with two parents who were in the military full time and dedicated their life to service and a grandparent who fought in wars. And, you know, I was lucky to be born into a country like Canada. And I do feel, and I still feel that there's an obligation to give back and to make Canada the best that I can make it. And I just choose to do that in a different way today. But for 15 years, I literally dedicated my life to my craft.

What else do you want to share about that period? You know, you're saying sort of that's the preface. What's the main course?

Well, so when you start working at an intelligence agency, you end up with problems that you've never encountered before that there's no solution before. You can't Google. And what I loved about it is you can't ever not play the game, if that makes sense. And I use the word the game, but don't take it too seriously. You can't opt out of this. You have to play. And you're competing in a global market similar to business, where people have better talent than you in some cases, more money than you in some cases, and more resources in some cases. And you can't complain about that. You just have to deal with the hand that you have the best of your ability and find a way to compete. And for anybody interested in those type of problems, intelligence agencies are like the place to be. But the flip side of that is I dedicated 15 years to that, and I ended up getting divorced and deciding I didn't want to spend my life at an intelligence agency anymore, and I wanted to do my own thing. I wasn't quite sure what that thing was in the moment. I just knew. There's a saying in the military that the uniform doesn't fit anymore, and it basically means the military is not going to change. And so if you're expecting it to change, then you're going to have a problem. And so there's that little, little thing. I think it was Steve Jobs who said, hey, if you wake up on a Monday and you don't want to go to work, that's fine, but if you do that too many Mondays in a row, like, you can waste your life. And, you know, I just woke up a few Mondays in a row and I was like, this isn't. I'm done. I need to find something else.

This isn't healthy.

Yeah, well, it wasn't healthy for me. It's not what I wanted, and it was for a long time. And that's awesome. But that doesn't mean I'm going to be unhappy going to work every day and trying to figure this out.

I've got sort of two things in my head now. One is I have this kind of image of you when you say game. It gives me the idea of Ender's game. And I can kind of imagine you now as. Is it Andrew Ender? Is it Wiggins? Gosh, it's wild. But I sort of imagine you as Ender in that game that must be played.

I would be more like Ender's assistant, maybe. I was. I was super. I was super lucky. I ended up, you know, working with probably just through luck again, like a lot of moments of luck in life. But I ended up working with, I. I would say one of the top three people in the world at the craft that I was in, and that had had ups and downs. And if you read my book, you can find some interesting stories about some of the downs. He's one of the most brilliant people I have ever met in my life. And to put things in context, he's the person that everybody calls when they can't solve a problem, even to this day, even though he runs a cyber defense company now called Field Effect, he was and is sort of the Michael Jordan, the Kobe Bryant, the whatever you want to call them of that.

The ender.

The ender. He was the ender. Yeah.

So he, he's, he's this, he's this leader with a very particular set of skills.

Yes.

That allows him to be extremely useful, extremely valuable in the most complex no win situations.

Yeah.

But his obsession, his, his level of it really, in some ways his level of competence and, and commitment has an unintended consequence on your life and your experience.

Well, his standards.

Right.

Were definitely higher than the standards I had for myself when I arrived. And you know, one thing that I find really interesting is that the very best people in the world, one thing that they all have in common, and you know, you and I have spoken to a lot of them, is they tend to have extremely high standards of themselves and they have extremely high standards of the people that work with them. And it can be a shock. There's quite a contrast between, you know, when I started and when I didn't. And somebody tells you there's no excuses and you have to do your job and it doesn't matter that the bus is late, it doesn't matter that you don't know how to do it. It doesn't matter that you like, none of your excuses just matter and they hold you to a higher standard. And that standard raises where you're at. You can run away from it or you can embrace it. I remember walking out of a meeting with him once and somebody walked up to me and said, hey, most people just avoid him. Don't worry about it. And he had basically called me out in this meeting and made me look like an idiot. I had tried to explain how something work and he just stood up and like really explained it. And I was like, oh. And then this guy, you know, comes and he's like, yeah, most people just avoid him. Don't worry about it, happens to all of us. And I was like, avoid him. And I remember pausing in the hallway, I'm like, I want to, I want to be around, I want to work with this guy. I want to be around him. Like, are you kidding? Like, he's clearly brilliant. I can learn so much from being there. And so I guess how you interpret being around people who are exceptional has a huge impact on, on where you go? And I was like, oh, no, man. I ended up spending more time with him than my girlfriend at the time. And it was just a great learning experience about learning not only the craft that I was involved in, but learning the standards of excellence that are needed to be at the highest level in the game.

Now, you said earlier on, and I don't want to delve if you'd rather not, but you said, okay. So I ended up at the end of this 15 years, I'm divorced. So are those related? Do you see the obsession of the work that you were being required to do at this crazy level of totally of expectation, no excuses. This is your whole life. Is that connected? I see you nodding. So, you know, do you have thoughts on that?

I mean, how could it not be connected? You know, for eight years, I basically spent 16 hours a day at work, six days a week. All the time that I could have been investing in my relationship, you know, I was at work. And so, you know, we all go through inevitable ups and downs in relationships. And, you know, I was in a bad position when we went through a down. And I think that that definitely was part of my contribution to my marriage not working out. And hopefully this can become, you know, hopefully my hindsight can become somebody else's foresight and make their relationship better. And so if you think about it in terms of positioning, which is something I talk about in, in clear thinking, it's, you know, if you water the grass in your relationship every day and you invest in it and, you know, you make sure that you're connecting and you're close with your partner and you're spending time together, then you're still. It doesn't mean you're not going to have these stupid arguments from time to time or disagreements or that something's not going to come and get between you, but it does make a huge difference in how you handle those moments and the ease at which you handle them. And watering the grass is such an apt phrase, because if we water the grass, what happens? It never goes dry. And if a spark goes on wet grass, it just goes out. But if we don't water the grass, the grass goes really dry and a spark can start a raging fire. And I think of it in terms of positioning, right? How do you position yourself to invest in your relationship? And how do you position yourself with your partner so that you're building something together, that it's going to survive these ups and downs?

That's a beautiful way to wrap part one of this interview, this theme. It runs like a golden thread. How we can learn the best of what others know. That's a theme that continues as we move into the second part of the conversation about the journey to Farnum's Tree, to the Knowledge Project, and to the Clear Thinking Book. For everybody listening, what is one thing that you have heard in the conversation so far that stands out to you? What is one thing that you can do differently as a result of this conversation? And who is somebody that you can share that with so that the conversation can continue? Now that this part of our conversation is over.