Greg McKeown:
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. He’s the mastermind behind the widely acclaimed Farnam 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 steer clear of the cognitive errors of our lives. His contribution is enormous but also amazing with his new book Clear Thinking. He’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 when 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.
Shane Parrish:
Well, thanks for the incredibly generous introduction, Greg.
Greg McKeown:
Well, it’s deserved. I want to just dig into some of this journey. Let’s start with your early years. You were, I think, maybe eight years or nine. 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, The Watch Stop Gang. Am I saying that right?
Shane Parrish:
The Stopwatch Gang.
Greg McKeown:
Tell us about what that is and why it mattered so much.
Shane Parrish:
Yeah, so I mean, I can’t speak to other people’s childhoods, but my childhood was a bit rough, especially when it came to school and academics. For whatever reason, I just didn’t fit in a classroom, and I was bored and, you know, 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 questions to be.
Greg McKeown:
Sure, like, what kind of mischief would you get into?
Shane Parrish:
Reorganizing books, vandalism, deleting stuff from computers. Just you know, petty mischief that you know you get into when you’re sort of thirteen. Going out on my dirt bike with my friends. So in grade seven, I had skipped school for seven weeks, and then I decided to go live with my biological…
Greg McKeown:
Hold on, you skipped school for seven weeks?
Shane Parrish:
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 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 treehouse, and I’d eat eggs. I’d make myself eggs during the day.
Greg McKeown:
Wow.
Shane Parrish:
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, this 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. You know 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. In grade seven, I was sort of on my own, getting in trouble. In grade eight, I was encouraged by the people I was hanging around to get into trouble.
And I remember it was 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, um, 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 about my thoughts and whether they were right or not. And you know just a really troubled childhood in that sense. Anyway, so I ended up in this true crime section of my grade eight library which had two books. One was called The Stopwatch Gang, and I was like, “Ah, this one looks interesting.”
I just randomly picked it up off the shelf and started 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 ah, 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 you know what does it take? And you know how do the cops catch them? And it became this like real life sort of…I don’t know if it was a true story, and it was so captivating, and I was so into it, and my friends 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, you know, they’re on their dirt bikes. We live in the middle of nowhere. And I was like, “No. You know I’m not feeling 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, and 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 bad part. It happened to be a cop’s house, and their lives changed at that moment.
Greg McKeown:
What? What? What? Sorry? What do you mean? What do you mean you skipped over the bad part? This feels like kind of the bad part.
Shane Parrish:
Well yeah, oh, 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, well, 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 them at the time and I just got scared straight. Like, 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 I could have gone either way, and I felt bad because maybe had I been there, I could’ve warned them, and they would have gotten in less trouble. Or, you know, and alternatively, I also was like, oh man, like my life just flashed before my eyes and in a very different way because of this book, right? And I was pulled into this world, and that was the sort of thing.
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 ah before. And so in grade nine, I went back to living with my mom and my dad, and um, you know, I found computers in grade nine. 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. 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 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 and, well nonfictional world in this case, and you know that’s how I survived the rest of grade eight. I Just actually read books. I 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 ten.
Greg McKeown:
There’s so many places to go with that. But well one place to go is how did you go from that description to being a spy for the Canadian government? I mean, that’s quite a shift.
Shane Parrish:
Yeah.
Greg McKeown:
Other than there’s something. There’s like a a golden thread through everything you’ve just shared, which is sort of, how would you describe it, kind of low-key nefarious. I mean that seven weeks you’re away from school, that’s more than just, “Oh I took off for a day.”
You know there was a strategy to that deception. You know there was, 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?
Shane Parrish:
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.
Greg McKeown:
Connect the dots here.
Shane Parrish:
And I got 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, you know 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.
Greg McKeown:
So you said that your grades changed. What changed in Grade ten? Do you know what changed?
Shane Parrish:
Grade ten. So I switched schools every year until grade ten. So grades ten and eleven were the first two years I went to the same school two years in a row.
Greg McKeown:
Good grief, that’s a lot of schools. That’s a lot of disruption.
Shane Parrish:
I knew in grade ten, I had moved from grade nine to grade ten different provinces. And I knew in grade ten 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 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’d 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 was like, “What do you want to do?”
And I’m like, “Well, that guy over there is like throwing a football and he doesn’t look to be working so hard.”
So 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.”
And I’ve never thrown a football on a team before. That first year was a bit of a disaster. I get the nickname third string because I definitely did not see the field the first year. Anyway, I ended up talking to somebody after practice who became my best friend in high school. And his father and my grade eleven 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 ten. It’s sort of October. And I went 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 like what I wanted to be, and I was like, “I don’t even, you know, like what is university. Like, that’s not a word that we use in my house.”
Greg McKeown:
Wow.
Shane Parrish:
I don’t know what that means. It sounds expensive, right? Like it sounds like it cost money, and you know we can’t really afford that and 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. He was 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 to go to the bathroom, and he sort of like nudged 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.”
Greg McKeown:
Wow.
Shane Parrish:
And I was like, “I don’t even know what university is.” Like 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 grades.”
And he laid out pretty much like what that means. And his son, you know, became my best friend, and it was okay to be smart. All of a sudden.
Greg McKeown:
Wow.
Shane Parrish:
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. And so I ended up doing pretty decent in high school I would say I didn’t do homework, so I could get 0 to 10 in most classes on homework, but I still got the high 80s in my grades, so it was good.
And I worked full-time for most of high school to pay for university because Mr. Corcury sort of instilled in me that if I wanted to go to university, 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 loved playing on computers. I loved programming. I loved 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? Back before that sort of got a bad name to it.
Greg McKeown:
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 the conversation that his dad has with you. You know, but for the fear of God, Go I. You know, like this, how different life would have been even at that point without that intervention.
Shane Parrish:
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 up. At 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 were 10 versions of question one, and each version of question one had different numbers, and so 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 would basically have to like enter the right answer and then go on to the next question, and you know these assignments took like twenty hours to figure out. They were for physics majors. They were not for computer science majors. This was like serious physics.
Greg McKeown:
Wow. That is impressive.
Shane Parrish:
All the kids in my class used to hire the same two tutors, and these tutors had a spreadsheet. They basically looked at what version of the test you had. entered your numbers and, you know, spat out the results. People would take those results and, you know, for 20 or 50 bucks, or whatever it was at the time, they would be done with their assignment in a matter of minutes.
And I couldn’t afford this tutor, and since nobody else had my question, I had…
Greg McKeown:
So by tutor, you don’t really mean tutor you mean just someone who did the work for them.
Shane Parrish:
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 you know 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 point one 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. There were no limits 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 March, you know, he shows this little presentation, and on the bottom is your student number, so on the x access is your student number, on the y axis is the number of guesses. And you know, the average guesses, the number of attempts per assignment was, I don’t know, like eight or twelve, and then there’s one student who like broke the chart several times, and he’s like, “I would like to see the student in my office after class.”
And so I show up at it.
Greg McKeown:
Wow.
Shane Parrish:
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.”
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 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, “I can’t afford to do whatever everybody else is doing, and I’m working forty hours a week. While trying to come to this class.” You know, basically like a sob story.
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.
And so, long story short, to bring this full circle to how I got my job. When I was doing my interviews to get the job, they talked to everybody. They ended up talking to him, and he finds me in the hallway and he says, “You know? 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, “You know, 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 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.
Greg McKeown:
How long were you working for the intelligence agency?
Shane Parrish:
Can I just preface this with like I had the best job in the world, right? I started two weeks two weeks before September 11th. I got to work with some of the most insanely talented unsung heroes in the world for fifteen years.
Greg McKeown:
Oh, my goodness.
Shane Parrish:
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. They are an amazing group of people who I still love to this day. And so I worked there for about 15 years.
Greg McKeown:
Can you give me just a tiny but concrete example of something someone did that makes you preface it like that?
Shane Parrish:
No, not without going to jail. I don’t want to walk any lines here.
Greg McKeown:
So you mean people on the front lines of action? You don’t mean the…give me more, something more.
Shane Parrish:
Well, I worked for the Canadian version of the NSA or, if you’re listening in the UK, GCHQ. 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 lives 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.
Greg McKeown:
What else do you want to share about that period? You know you’re saying sort of that’s the preface. What’s the what’s the main course?
Shane Parrish:
Well, so when you start working at an intelligence agency. You know 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. I use the word the game but like 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 to the best of your ability and find a way to compete and for anybody interested in those types of problems, intelligence agencies are like the place to be.
But the flip side of that is, you know, I dedicated fifteen 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 at the moment; I just knew that 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 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, 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 it. I’m done. I need to find something else and so yeah.
Greg McKeown:
This isn’t healthy.
Shane Parrish:
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.
Greg McKeown:
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, was it Andrew Wiggins? I sort of imagine you as Ender in that game that must be played.
Shane Parrish:
I would be more like Ender’s assistant. Maybe. I was super lucky. I ended up working with, probably just through luck again, like a lot of moments of luck in life. But I ended up working with, I would say, one of the top three people in the world at the craft that I was in, and that had ups and downs. And if you read my book, you can find some interesting stories about some of the downs you know. And he’s one of the most brilliant people I’ve 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. You know he was and is sort of the Michael Jordan, the Kobe Bryant, the whatever you want to call them of that field.
Greg McKeown:
The Ender.
Shane Parrish:
The Ender. He was the Ender. Yeah.
Greg McKeown:
So he’s this leader with a very particular set of skills that allows him to be extremely useful, extremely valuable in the most complex, no-win situations, but his obsession, it really, in some ways, his level of competence and commitment has an unintended consequence on your life and your experience.
Shane Parrish:
Well, his standards 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, 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. You know they hold you to a higher standard and that standard raises where you’re at, and it. 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, you know most people just avoid him. Don’t worry about it.”
And you know, he had basically called me out in this meeting and made me look like an idiot. Like, I had tried to explain how something worked, 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. 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 be around him. I want to work with this guy. I want to be around him. Like, are you kidding? 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 where you go. And I was like, “Oh no, man, like I want to.”
I ended up spending more time with him than, you know, 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.
Greg McKeown:
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 fifteen years I’m divorced you know are those related.”
Do you see the obsession of the work that you were being required to do at this crazy level of expectation? No excuses. This is your whole life. Is that connected? I see you nodding, so you know you, do you have thoughts on that?
Shane Parrish:
Yeah, I mean, how could it not be connected? You know, for eight years, I basically spent sixteen 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 Clear Thinking. 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 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 app 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 and 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.
Greg McKeown:
That’s a beautiful way to wrap part one of this interview. This theme, it runs like a golden thread on how we can learn the best of what others know. That’s a theme that continues as we move into this second part of the conversation about the journey to Farnam Street, to the knowledge project, and into 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?
