Paige Bainbridge

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Ultralearning: An Interview with Author Scott Young

by Paige Bainbridge on September 3, 2019

I started following Scott Young’s blog several years ago when I worked for YouScience, a company that sold an online aptitude test (if you aren’t familiar with YouScience, you should check it out. It’s an amazing resource). When I stumbled upon Scott’s site and learned about his MIT Challenge, all I could think was, “who IS this guy?” In one year, Scott took on the project of learning the MIT computer science curriculum online. By himself.

He then went onto a language fluency project where he and a friend lived in four countries during a one year period. Their goal was to become fluent in the four languages (three months in each country) through immersion. Scott’s blog shares many of these extreme learning challenges and adventures, as well as helpful tips based on research and his own trial and error process through the years.

His new book Ultralearning was recently released. In it, Scott shares the principles needed to be an “ultralearner,” being able to master hard skills quickly. Scott lives in Canada and I had the pleasure of doing a phone interview with him. He shares his thoughts on everything from how to motivate high school students to procrastination and spectacular failures.

What was your childhood like? Were you always such a highly motivated individual?

It’s a hard question for me to answer because I think for each of us, we are just ourselves, right? We don’t think there’s anything unusual about how we do things. It’s only when someone points out a comparison we might think, “Oh, most people don’t do X.” I had wonderful parents and they did a great job raising me, but I don’t think they pushed me to do these kinds of projects. But when I was around 15, I discovered this guy, Steve Pavlina, who now is a popular alternative personal development blogger. But at the time, he was running a software game business online.

He was writing about his experiences and it struck me as really cool. Oh, you could be your own boss and have your own business and just, like, make things? And people will pay money for them? The idea that it’s something you could do for a living immediately appealed to me. I was aware of how difficult it would be to do, but nonetheless it was interesting to me. So that’s where I got started not only working hard on things but in the whole self-improvement arena. 

And then another big motivator I had, which was years later, was meeting Benny Lewis. I mention this in the book. Again, I’d always been interested in learning. I was a student at the time so I was interested in learning from a perspective of how to get good grades without stressing too much about studying. But when I met him, it was about learning outside of the school context.

It wasn’t just about how do you pass classes, but how do you acquire meaningful skills?

Also, his approach to learning, like the fluent in three-month challenges. I’d never seen this before. I really liked what he was doing in taking on an ambitious challenge and documenting it while you’re doing it. It was exciting. So yeah, my first project was the MIT challenge. And then the response I got from that put me down this path even further to do more projects like that. To take learning interests and turn them into ambitious projects. 

So you had a business degree from college, and you wanted to be more entrepreneurial, and maybe write software?

Yeah, I wanted to have my own business like this person I admired who had his business online (Steve Pavlina). When I went into university, I was thinking that the most important thing would be learning business because if you want to start your own business, you should know the business. But I came to the realization that what you really need to know how to do is make things. And so the computer science degree is something I thought about for a while. Then when I found these MIT classes online, it seemed like, “Oh, here’s my chance to do something like Benny Lewis does.” I could stake out a challenge and do it.

Scott Young did the MIT Challenge. He's an expert on learning. Here he is with some books he's studied.

And I thought it would be interesting because my blog at the time was still focused on these student topics of studying for exams and the like. And so it seemed natural to me. Computer science had been something I’d wanted to learn for years. I had learned a little bit as I’d used some of my electives to do some classes in my business school education. And so here was an opportunity to learn a subject that I’m interested in (and kind of wish I’d majored in), but also to do this kind of ambitious blogging/learning project like Benny Lewis and see what comes from that. 

The MIT project was really ambitious. There are very few individuals who would be able to pull that off. Or even have the desire, much less the fortitude, to seek it.

Yes, it was an ambitious challenge, but I felt like when I first encountered Benny Lewis’ projects, those were ambitious to the point of parody. The fluent in three months project was so ridicoulsly out of line with what I thought a person could accomplish. That was my impression of it at the time. Because I had been studying a language; I was living in France.was doing the “right things” to learn. I was studying at home, and I wasn’t getting anywhere close in that time frame. So there was a sense that there was something magical about that, or possibly fraudulent. Like how can a person possibly do that? In the years after that, I did a project that was similar in learning languages.

And for me, it was a realization of, oh — the status quo for doing these things is actually not very efficient.

My point is not to say everyone can do the MIT challenge. I don’t think that’s the case. But I also don’t think I’m some kind of rare genius in learning to have done it. I think the reason the MIT challenge succeeded is because, first of all, the simplifications I had to make to an MIT degree, like focusing on just final exams and programming projects actually do offer a lot of flexibility now. I mean, it’s possible to learn more effectively if you have total control over all the parameters. And I could take exams whenever I wanted to. I could watch the lectures at twice the speed. There were a lot of things that could impact them. 

Now, I don’t mean to say that every single person reading this could do that, but if you were dedicated enough, you could do it. And it’s funny to talk about dedication because people say, “how the heck did you stay motivated to do this year-long project where you have to put in these crazy hours?” And I say, “how do you medical students do it?” It’s way more than a year and they work harder than I worked. How does every single high school student in China do it?

To me, I think the thing that is odd is people are unable to put in that kind of effort if there isn’t the social pressure. Not that people are unable to put in that kind of effort. Because people regularly do that for formal education. I did work really hard, but I was excited about it — it was a chance to do something unique and original. So when I think back to the project, yes I did work hard. But there were some areas where I got lucky.

I picked doing this over a year, and I did some planning. And I could have gotten halfway through and realized it was going to take over a year. It didn’t turn out that way, but I kind of look good in hindsight. But it easily could have been that the later classes were much harder than they turned out to be. And I think that for some people, if you don’t have the background and aptitude, it would take them longer to do the class under the same constraints. So I’m not going to say everyone is equal.

But there are tons of smart people who I think could do something similar. I think the reason they don’t is maybe it’s hard for people to pursue goals that don’t have that strong social pressure.

I do hesitate to say, “everyone can do this.” I chose it because I thought it was going to be ambitious and difficult for me to do. I’m a reasonably clever person and I was super-motivated to do it. Maybe a lot of people couldn’t do it. At the same time, people regularly work harder on their studying than I did during that year. I’ve met people during other residencies in medical programs where they do 30-hour shifts and they sleep like 6 hours in a week. I wasn’t doing any of that.

I wasn’t working in the evenings or studying on the weekends. It was a strenuous project and I was working hard, but I don’t think I was approaching what the human limits for focus were doing that year. So I think it was some choices I made that not only made it easier to pursue than an MIT student would do because I was simplifying things and also because there’s no social background supporting this kind of goal. 

The whole time you were still doing your blog and supporting yourself with money you made from that?

There’s a sub-project there. Not only doing the thing you’re learning but also documenting and blogging about it. So I did maintain a minimal version of my blog and business. I didn’t make a ton of money that year. I made enough to get by. It was fine because I was just out of university and I’d had the experience of being a broke stunt up until that point. I think I would have had a lot of difficulty managing my blog and business now, but I didn’t back then. I had to record videos once a week, I was writing blog articles. So my schedule was Monday to Friday doing the actual MIT challenge and then Sunday was doing the business. 

After that, the language project came next. How did you select the languages you would learn?

Oh man, that was a long discussion between my friend and me. We had considered learning a lot of different languages. At first, we wanted to do a world trip and cover a lot of different continents. That was one of the reasons we chose Portuguese. I think we both wanted to learn Spanish, and then I also really wanted to learn Chinese. My friend really wanted to learn Korean. In the time since I’ve put a lot more effort into my Chinese so my Korean is not as good as I’d like it to be. Whereas with learning Chinese, I worked really hard when I was there and I’ve continued to work hard the last five years. So I’m nearly fluent in Chinese. But with my Korean, I can’t discuss global politics or stuff like that.

I love the story about when you got off the plane in Spain and there were British girls you couldn’t talk to because you had made a “No English” rule for yourselves…

Oh yeah, there were a lot of stories like that. Spain was the country we were the most strict about the No English rule. Part of that was we were just starting out, and you can’t be wishy-washy off the bat. But then when we were in Spain, we got so much success with it. Really, it’s hard to communicate the feeling we got in Spanish because I think in some ways even the objective level we reached in Spain doesn’t capture it.

Because the way that you’re learning when you’re doing immersion is that it’s not that you’re learning some random subset of the language. You’re learning exactly what you need to know how to survive in this place. We were having conversations with friends and going to parties. I think it’s hard for a lot of people to even think about it because the normal process of learning a language is so slow.

But Spain really worked. That was the clearest example of, okay, this principle worked.

In Brazil, we made some mistakes that held us back. One was the location we picked, which was a small, touristy town, and it made it harder to make friends. A lot of friends that we did make were from Argentina or other Latin American countries, so we spoke to them in Spanish. We did get better at Portuguese, but we didn’t reach the same level as we did in Spanish because we didn’t have the ideal environment like we had in Spain.

Asia was a different story because the languages are so much harder. So there were moments where we would crack. Particularly in Korea, we would crack and not adhere to the No English rule. Although, I’ll say in thinking about it now, It’s much better to go to a place with the idea of the No English rule and break it from time to time if you have to. That’s better than going to a place and saying, “I’m going to speak the language as much s I can.”

Because if you go with the No English rule and you break it 5% of the time, you still spoke the foreign language 95% of the time. But if you go with the idea, “I’m going to practice as much as possible,” what are you going to speak? Maybe 30% of the time if you’re lucky. So even in China I was really strict. My friend was not as interested in learning Chinese as he was Korean, so there was motivational disconnect there.

Scott Young traveling and learning languages.

And for him, he was struggling a lot more in China. It was a little unfortunate but the solution was we didn’t hang out as much as we did in the other two countries. So I spent more time with friends that I met in China where I could practice, as we had more separate existences. And then in Korea, I think we were both burned out by then. So, again, it was unfortunate, but our solution to the No English rule was to become more introverted.

We were not communicating as much as we had in previous countries. Which is a little disappointing looking back on it. A lot of people would say, “doing immersion must be exhausting.” But it didn’t get exhausting until country number four. We were fine for the first three countries. Then we finally got tired. But that was after a year of travel, too. And Korea had some other things I didn’t like. We were staying in a crappy little dorm room and I got bed bugs. So there were some other things going in in Korea that made it less than pleasant. 

What would you say about the benefits of learning a foreign language for your brain?

Yeah, I’m skeptical of the whole neuroscience argument in favor of learning another language. I mean, I’m not ruling it out, but my whole research into transfer weighs against that. I think the main benefit is that you don’t realize as a monolingual speaker (and having been one for 2/3 of my life) how much of the world is invisible to you. People say, “I can get stuff through translation.” No, you can’t. I don’t want to be one of those snobs who say, “Oh, if you’re not learning the language, you’re not really understanding things.” I don’t want to be like that.

But at the same time, you don’t realize how much of the world is just opaque to you. Because the people who have different perspectives from yours can’t talk to you.

So yes, you can communicate with people from other countries, but invariably the people you can communicate with are those who have learned your language. So in a certain sense, they’ve learned your way of seeing things and know how to translate into your way of seeing things. They’re already coming onto your side of talking about how the world looks.

 I found especially in China, there’s almost this entire parallel universe that has a completely different culture and traditions. China is 1.6 billion people. We’re talking about a huge portion of the world. And they are more aware of the Anglophone world than we are of the Sinophone world. Even so, you can go there and realize the things you think are global politics are just so local. The things that you think are global perspectives or values are just your perspectives or values. And also the ways we’re all similar, too. So it’s not even just to say that other cultures are so exotic and alien and different from ours. Sometimes the things that make us seem really different are the incomprehensibility of language.

Once you are learning another cuture you realize how parents in China love their kids. And they’re trying to study for exams. And they’re also dealing with the ideas of how do you fit into a society and have personal freedom, and have the things your’e passionate about? So you have lots of conversations that also reveal the deep similarities. That’s the reason to travel and learn other languages. It’s to realize how narrow the perspective of the world is if all you do is stay and home and do everything in your native language. There’s so much of the world that’s invisible to you.

Do you have any opinions about male vs. female learning, especially regarding high school students?

Interesting. I think we we’re talking about men vs. women, this is a contentious area of research because some people point to innate differences and some think these are overblown. Again, a lot of these learning mechanisms that underlie a lot of the techniques I’m talking about are not gender-specific. I know there’s a bit of a stereotype that girls are more organized and conscientious than boys are. I’m not sure that’s true. For instance, I don’t know any research that shows girls generally score higher on conscientiousness when they do big five personality tests than boys do. I have heard that women score higher on agreeableness than men, but I think that’s also probably cultural, in what we expect from men and women. I think there are probably cultural differences in attitude toward school. Especially in North America. I don’t think this is a universal phenomenon. 

I remember being a high school student. For a girl to succeed academically, it was a neutral thing about her. But for a boy to succeed academically, it was often, “oh, you are kind of a nerd and sort of brainy and you should be more macho and masculine and good at sports.” At least in the area that I grew up in. In some ways it was like being culturally conditioned to be negligent toward studies on purpose. “You don’t want to be like one of those people who are trying too hard.”

Scott Young and friends

I have a good friend, the one I went on the language trip with, and he’s from India. I was explaining to him about the high school culture I came from. And he thought it was the most bizarre thing he’d ever heard. Because at his school, if you were top of the class, you were the most popular kid. Everyone was trying to succeed in school. So if you were acing all the exams, that didn’t make you a nerd or loser — that made you cool. 

I think there’s something very dangerous about how we enculture men in Western society to have a kind of anti-education.

“Oh, that nerd stuff,” like it’s somewhat less masculine. I’m sure there are things we are doing wrong with how we enculture women as well. But I think definitely at the high school level, a lot of boys are falling behind because they subtly pick up from the surrounding culture that it’s not what they should be getting good at. I felt that way when I was in high school. Maybe it’s changing, and maybe it depends on the high school environment. But when your friend is saying, “I don’t think boys should do that,” I think it’s partially because we subtly try to teach boys in our culture that they ought to be tough and masculine and that’s somewhat contrary to being smart and good at school. And that’s very worrying for me.

I think that does tend to go away as you get older. But at that level it’s often a critical juncture for these people. This is deciding where they go to college. Maybe this isn’t universal and I think there are some schools that aren’t like that. There is often this perverse anti-intellectual streak that I think happens in North America. I do find that very interesting and it does tend to impact boys more than girls just because it seems to be tied up into our concept of masculinity. Our concept of who boys ought to be and what is cool. Not nearly a rebelliousness but also a kind of — you’re sort of macho and street-smart and good at sports — and those all perceived as contrary to academic success. 

For me, when I was in high school, if I did well in classes, I would try to conceal that. It wasn’t a bragging thing. It was something to hide because it was considered uncool or unpopular. It’s going to be really hard to motivate a young boy to do studying tactics even if it will help his long-term future if in the short-term, it’s going to affect his peer image. It seems to be changing, and it’s really hard to generalize. But it’s something I’ve noticed in Western culture that I think is perverse and affects boys more.

Speaking of motivating high school students to improve their study skills… what would you say?

If we’re talking about teenagers, and we’re not just talking about a three-year-old that we’re telling them what to do: give people tools so they can solve their own problems. For a lot of people, they are just not aware that if you spend the same amount of time learning something, but instead of cramming it right before the exam, you spread it out over the course of the semester, you’re going to remember it better and not have to study so hard. So I think faced with that information, it’s like, “how do I implement this in a way that’s relatively painless?” One way of doing that would be instead of studying a lot right before the exam, you’re just doing regular review sessions.

Graphic from Scott Young's blog about spacing for exam studying. He's an expert on learning.

 We talked about retrieval in the book. There’s certainly a lot you can do with flashcards or a repetition system. Why does the person feel like they don’t want to do homework or study in this way? Is it because they don’t feel like they need it? Or is it because they feel, “oh, I know how to do this,” and they’re not aware of some of the blind spots they have with their own learning? Spacing was not something anyone had ever taught me when I was in school. The idea that retrieval works better for studying was not something anyone had ever taught me in school.

The selling point to a teenager student or anyone who wants to learn better is these are tools: it’s your choice if you want to use them. But if you do use them, they will allow you to get better results with less stress and effort.

And it does require planning, but I think that’s attractive to a lot of people. And I think it’s a better pitch than, “Oh, you really ought to be doing this.” If you’re a student in high school, you want to be able to get results with less stress and effort. I think co-opting someone’s own motivation is better than prescriptively telling them what to do. That’s one of the things I didn’t like about school is they just tell you to do stuff and they don’t explain the rationale. “Just follow my instructions because I know better.” But I think if you don’t explain to someone why something is better than what they’re currently doing, and that explanation really makes sense, it’s often lost on students.

I remember being in university and professors would say, “well you really ought to be doing X.” It’s not that students are lazy. But if you multiplied that by the five other classes they had, no one would have time for that. Sometimes a student is trying to balance all the values they have in their lives. So they’re not just trying to succeed in school, they’re also trying to appeal to their friends and succeed romantically, be good at sports.

Scott Young working on his computer

I think treating people like whole human beings who are making decisions for themselves and you’re saying, “Hey, look, maybe you don’t know this, but if you’ll do retrieval practice rather than review, it will feel harder, but you’ll score better on the test.” Each individual has their own situation. I think sometimes we don’t give students enough credit for being sophisticated individuals who really are trying to balance all the other things they care about in their lives of which school is just one.

Procrastination: is it a paralysis of being overwhelmed at how much you have to do, so people cower and hide from it?

I think our decisions our driven emotionally, but I feel like there’s an implication that if you were rational, you wouldn’t do that. And this is an emotional decision so it’s irrational and no reason for it. But what’s often missing is that everyone makes all of their decisions emotionally. That there are almost no decisions that are made rationally. We all make our decisions based on how things feel to us. And those feelings are a complicated set of pattern recognition going on in our mind, weighing all sorts of values and past experiences and integrating them into “do I want to do this or not?”

I think there are a couple issues when it comes to studying. One of them is (and this is particularly true of high school students) that they are complex individuals who have multiple values they are trying to pursue of which succeeding in school is just one. In the same way that you wouldn’t want to study all the time, you would have other things that you care about, students are like this as well.

Graphic from Scott Young's blog

And so sometimes the lack of performance in academics can be because the student cares about something that maybe the parents don’t think is very important but is important to the child. Like having good relationships with their friends, or achieving something in a video game. I remember being a high school student or younger and playing video games , and those things felt really important to me. They were an important part of my life in a way they wouldn’t feel now. Sometimes there’s a value shift. I think that procrastination often hits when we have an aversion to doing something. We learn how to feel about things.

There’s a concept known as hyperbolic discounting. Basically, what it means is we really value short-term experiences a lot more than long-term experiences.

And a lot of people are puzzled over this. Some people say it’s because in our ancestral environment, it was so uncertain that if you didn’t take advantage of some opportunity now, it would be gone. And that there was no such thing as planning; it was just surviving from moment to moment. I’m skeptical about that explanation. I think it might be rooted more deeply in information processing. 

For instance, let’s look at machine learning. A common algorithm for learning from feedback from the environment is called reinforcement learning. The way it works is whenever you get some reward from the environment, you look back at the last several sets of decisions you made. You then say, “okay, do more of those in the future.” And if something bad happens to you, you look back at the several sets of decisions you made and say, “okay, do less of those.”

And the problem is that the further something is separated in time, the further reward is separated from the behavior, the harder it is to learn this way. If we’re playing a game of chess, and a decision you make on turn one leads to losing on turn fifty, that’s much harder to learn than if a decision you make on turn forty-eight leads to your losing on turn fifty. And so it may be related to that.

My idea here is that we tend to be fairly myopic and short-termed focused in our emotional responses to things.

And so, yes, you can say “of course you need to focus on learning and studying.” Well, why? “Because you have to go to college.” Why? “Because when you go to college, you’re then going to get a good job. And that’s going to lead to your success in life. Etc.” But we’re talking about something that is decades-long that the student doesn’t have any personal experiences with. So they have no way to learn this intuitively. They just know that the culture expects them to do this. I think managing our motivations in those situations can be difficult. Because studying is less fun than doing some other activity. It is less intrinsically rewarding. What I talk about in the book is recognizing that this is a reality. But we also recognize that we can cope with it by investing in these things I call crutches. 

When does it feel that you don’t want to do it? Very often, it’s the initiation of an activity that feels the worst. So maybe you can make it a habit so that you just start initiating it. The other thing is we’re talking about habits being so important. I think a lot of students (and adults) don’t realize how much of our behavior is automated. How much we are running on autopilot. If you require manual intervention every time you start studying, well, yeah, of course, it’s going to be difficult. Because that’s always going to represent a decision that requires some of the executive control centers. “Okay, I guess I better go study.” That can be difficult to do.

Scott Young

Whereas I think investing in a productivity system is better: I always study at these times. If you can get into the habit of doing that, then it becomes automatic. And so, again, this isn’t something I would impose on the student. You can say, “Hey, I know you haven’t been studying as much as you want to. Let’s have a conversation about how you can get your studying done. I know you want to accomplish the other things you want to do, like playing sports or video games or hanging out with friends.

And what would be a way of doing that so that it’s less stressful and painful for you?” I think if you become that kind of consultant role, a lot of students will respond well. They’ll say, “Oh yeah, I should have better habits than this.” And it’s not just the student saying, “well, someone else is nagging me to do something that doesn’t fit within my priorities.”

Instead, it will be, “oh this is something I actually care about.” Because I think most students do want to succeed in school. They want to do all these things. It’s just that they also want to do other things. And they also have to deal with the fact that maybe at this sort of emotional level, they haven’t had the life experience that you’ve had. Those experiences allow you to say, “this is why this is important; this is why you have to study and focus on learning. Because as an adult now I see the wildly different futures that people generate based on their success in education or based on how hard they work during the early stages of their lives.” So I think that’s something…they just don’t have as personal experience.

One of your blog posts talks about how we should all have more spectacular failures. Do you think our society discourages failure these days?

Oh sure, all societies discourage failure. All people discourage failure. No one likes to fail. The point I was making in that article is not to say that failure is good. I’ll put it this way. I’ve had friends who have gone out and done something ambitious. And when you do something ambitious, there is already a quizzical look in your direction like “why are you doing this?” But if you fail, it’s doubly embarrassing. Because you not only worked really hard, but others think or say “why were you sticking your neck out so hard doing that in the first place?” I think there can be a lot of social pressure to conform and to avoid not doing these goals that aren’t socially mandated.

Starting a business, going on a diet. People say, “well, counting the days til this person goes off their diet and eats and piece of cake.” And it’s kind of perverse that we treat each other this way. But I think there is a lot of our behavior that’s like the crab. You know that apocryphal example of a crab trying to climb out of a pail and the other crabs are pulling it down so none of them escape from the pail. I think there is some sense that we as human beings are like this.

When someone tries to do something ambitious or hard that is not the default social path, others around them are like, “who does this person think they are?” And it’s unfortunate, but I think it’s universal, in all places. 

Partially it’s because you’re setting the bar. Others say, “oh if people are expected to do this now, then I have to do this now and what does that say about me?” I think the idea of spectacular failures is that often when we engage in pursuits, we are always trying to manage our self-image. And part of that self-image is that we don’t want to look like failures. We want to maintain confidence. So it’s easier to say, “oh I just changed my mind about that.”

It’s much more socially palatable to say that instead of “yeah, I tried my best on this and still came up short.” Or, “I studied hard to be a doctor, and it was my third time in a row. I still didn’t get into medical school, but I decided to do something else because I didn’t want to work those long hours.” It’s not that the reason is bad, it’s just when it’s used as a rationalization because you were afraid of failing, that’ something else. You were afraid of not actually doing it. 

So the idea of spectacular failures is realizing as a life’s goal, you should be having situations where you fall flat on your face.

Graphic from Scott Young's blog, an expert on learning

Where you really tried your hardest and it wasn’t enough. The idea is I’m going to pick this goal and instead of midway through when it looks like it may fail, I’m not going to pivot to something else to protect my self-image. Instead, go to the end. Let’s see it explode in my face and not be worthwhile. And I think if you can cultivate that — it’s difficult because of the social pressure — you will have more spectacular successes as well.

Forgive me, Scott, but you don’t seem like the kind of person who’s had spectacular failures. You’ve achieved so much and it’s all so impressive.

Well, thank you. I think that’s one of the great things about writing a blog: you get to curate your own life and present the best picture of yourself. I’ve definitely had things that failed. Not perpetually. But when I started my blog, I felt like a failure most of the time. I was writing and working hard. Then I would see friend after friend become successful.

I remember a real moment of failure for me. At 15, I had decided what I wanted to do with my life. I’d really like to run my own business, and that’s not a normal career path. Most people are not successful at starting a business, especially this kind of business. I mean, it was an unusual kind of business at the time. Running an online business had a vague “is that a scam” quality to it. So I felt shy about telling other people. But I worked hard on it. Originally, I thought I was going to make video games (around age 16-17). I worked on this game for about 2 years and I just gave up. I didn’t like how it was going so I quit. There was a guy helping me out some and he was very disappointed I was quitting.

And that was when I started getting really into personal development, so I thought I could do something more in that vein. Then I pivoted to blogging. I was writing it for about 3 1/2 to 4 years. At this point, I’d written hundreds of articles. And I’d had a little bit of success with an E-book I’d written while in university called Learn More, Study Less. A few bigger bloggers had linked to it with an affiliate link and it grew in popularity. There was a month in the summer that I had made $4,000 from this E-book, and I thought, “that’s it — I made it!” I thought all  I have to do is to keep doing this. Time to double down and write another E-book that would do even better.

And I spent a long time in the summer writing another E-book which had a terrible titled called Think Outside the Cubicle. And it was so dumb of me to try to be clever and a half. But the idea was I wanted to write a book about productivity for people who work outside an office. So it wasn’t about how to start your own online busies or anything. It was how to be productive when you’re working from home.

My market was freelancers, entrepreneurs, and students. If you have complete control of your time, what should you do? 

The reason that was important is I was advocating a departure from the 40-hour work week. I was saying it’s better to work in these concentrated bursts even if it’s less than 8 hours a day. A lot of people who go into working from home try to put in these long hours, but they’re really inefficient. So by measuring your productivity by the hours you put in is kind of perverse because you feel burned out but you don’t get a lot done. It’s better to be task-driven. I had this whole philosophy.

I would say I still largely follow the ideas I wrote about in that book. And I put the ideas together and I made all these images for it. I was so excited about it. And I think it sold…it was pitiful. I sold maybe 50 copies. I remember I made the announcement about the book and I got one comment; it was some person saying “how dare you sell this?” And I was crushed. I’d been working on this goal for five years. 

It’s not a small thing to work on something for five years, absent a lot of positive reinforcement. It’s not a small thing to every single day having to motivate yourself, “this is my dream.”

And to go through failures like trying to set up a project and having it fail. Having friends become wildly successful while you’re still unrecognized and broke. And I remember at the time I was crushed thinking maybe I was wrong. Maybe this is a stupid thing. Being a blogger online is not a career. I remember being pretty bummed about it. I was living in France at the time. My thoughts were, “I’m still a student and this is a side project.” So I got a bit of a pass on it.

But I thought I was going to graduate in a year, and when I graduate, I’m not making enough money to live. But I was also thinking, “well, I don’t have anything better to do.” It’s not like I had some other idea for a business. So I thought, let’s just keep working on this until I graduate from university. And if it doesn’t fail, I’ll still have a blog. It just might not be enough to live off of full-time. Then I can get a job somewhere and start thinking of a new kind of start-up or entrepreneurship think that I like to do. 

So this kicking the can down the road helped me deal with this failure. “Well, I’m not going to do anything differently anyway so I might as well still work on it.” I very well could have decided, “screw this.” I had been working really hard. For a while, I was writing 10,000 words a week. I decide I’ll keep going with it and see what happens.

Scott H. Young, author of Ultralearning

And the real irony of that is about maybe 4 months later, I made a program called Learning on Steroids, which was a monthly subscription. That program turned out to be very popular, and it gave me enough to live off of. I’d gone five years without having enough success that I could reasonably live off of this, and success was just a couple months around the corner. The thing that allowed me to do it full-time. So we’re talking about spectacular failures and I get to play up my successes on my blog. But I’ve definitely had my share of disappointments and things that didn’t work out. I just tend not to be so public about it.

What’s so fascinating in hearing all of this is seeing the stepping stones and puzzle pieces on your path. All the things that you talked about that you were frustrated by and failures were all very significant learning experiences. Think about how many people might just quit right before success is right around the corner?

Yes, I think you’re absolutely right. When we’re talking about something like the MIT challenge, I think that kind of background context is important. I’d already spent 5 years knowing how to work really hard on goals that society doesn’t care about. So to do it for one year was nothing. People would say, “how did you do the for a year?” And I would think, “well how did I grind for 5 years before that?”

 I think I cultivated the kind of mental habits in learning to push through those kinds of projects. The MIT challenge is funny because to this day, it’s the thing that’s brought me the most attention. And that’s ironic because I like my language learning project more. But people like the MIT challenge more. While I was doing the MIT challenge, I didn’t feel like people cared that much. It was only after I finished that people cared. So while I was doing it, I was like “well, this didn’t really do anything for my blog. But it was still a fun project.” 

Again, with hindsight, you interpret a story totally differently than you do when it’s happening. That’s part of the whole idea of spectacular failures; it’s a perspective mindset.

It’s about thinking about your future in terms of, “yeah, if I’m going to fail at this, let’s fail at it hard.” But life isn’t like that. You fail at it and it’s just temporary. What is that quote? Success looks like failure right up until the moment you succeed. So in thinking about these projects, I also thought that way about the MIT challenge. I thought it was fun and I was glad I was able to do it. But I thought it was too bad people weren’t interested. And it’s so funny now because that’s obviously the thing people are interested in the most.

Do you ever veg and chill out? You seem so organized and motivated all the time…

If you could meet my wife and talk to her about what I’m actually like at home! I really care about productivity, but I’m very much the person where I have these bursts of intensity. A good 2/3 of the day I take a nap in the afternoon. I don’t set an alarm in the morning, so I just wake up when I wake up. It’s usually between 7-8am. It’s one of the things I talk about in my blog. I have the luxury of being lazy because no one is judging me for how it looks like I work; they’re just judging me for the work I get done. And I think in a lot of offices, everyone is trying to pretend to be busy. I don’t have to pretend to be busy. I can just read a book. 

Yesterday, for instance. I finished a podcast I recorded, then I got a haircut. I went to the park and laid down in the grass and read a book. I’m not always hyper-focusing getting everything done. But I feel like the skill that I’ve tried to cultivate is I make progress on the projects that are important to me. So if I’m trying to do something, I word hard. When I’m doing the MIT challenge or one of those projects, like when I was learning Chinese, I was studying pretty hard. But even then I was still within the confines of a normal work day. When I was doing the MIT Challenge, I was 24 years old, and I was still going to bars with my friends. I wasn’t living a monk-like lifestyle.

 I think that’s a learning lesson I try to teach because a lot of us are caught up in the appearance of things rather than the actual thing. So I think the appearance of being productive can vary. If something is difficult for you to get done, and you have a lot of anxiety about it, there can be a lot of struggle. That’s how it was with my book. I felt like it was a lot of anxiety trying to write and I procrastinated a lot. But there are other times where you say, “okay,” and you sit down for five hours straight and work. Then you go take a nap. I think that’s the kind of thing that can’t be done in a lot of other environments where people are judging you for how much work it looks like you’re doing rather than the actual result. 

************************************************************************

To purchase Scott’s book Ultralearning in order to improve your mastery of learning hard skills quickly, click here: Ultralearning.

To read my previous post on journaling, click here: 3 Ways Journal Writing Can Improve Your Life

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