James Altucher on Accelerating 10,000 Hours to Mastery

Chase Jarvis: Hey, everybody. What's up? It's Chase. Welcome to another episode of The Chase Jarvis Live Show here on CreativeLive, the show where I sit down with amazing humans. And today's amazing human is James Altucher. Now, you probably know James because he's written somewhere on the order of 20, count 20 books. His most recent one is called Skip The Line, which is a fascinating book. The subtitle of that book is The 10,000 Experiments Rule and Other Surprising Advice for Reaching Your Goals.

You can imagine a little bit of the subtext of our conversation in this. We also explore how curiosity is perhaps one of the most important vehicles for pursuing the thing that you ought to be pursuing with this one precious life. We also recap a really fascinating story where James wrote an article about how New York was forever changed by the pandemic only to be responded to by the one and only, Jerry Seinfeld in the New York Times.

And if that doesn't shake up your world, I don't know what will. There's so many nuggets in this episode about how to pursue your dreams, how to navigate difficult times. James talks very frankly about having a lot of failure going from depressed to bankrupt and recovering through processes like a gratitude practice. So fascinating episode. I can't wait for you to get into it now. So I'm going to get out of the way. Enjoy yours truly, plus James Altucher.

James Altucher, welcome to the show, bud. Welcome back.

James Altucher: Chase, I'm always so glad to be on the show. Thanks for having me here.

Chase Jarvis: A lot has happened. We were speaking before we pressed the record button about what a crazy last couple years. And as you said, this is the conversation that everyone's having, because we're talking to each other again, trying to uncork what has happened and where this is all going. You dropped a book somewhere in the middle. You've moved to Florida. You exchanged hate mail with Jerry Seinfeld. There are many things for us to talk about.

James Altucher: Well, to be clear, I did not hate on him. I exchanged solutions and possible problems and I think maybe he took it the wrong way.

Chase Jarvis: That's fair enough. For those who do not know, this is a fun and interesting way to dive into the show. Of course, James, you've been a guest on the show before. I've been a guest on yours. I think our relative audiences are aware or respectful. Our respective audiences are aware of the work that one another do, but to start just to give anyone who's new to this, new to our relationship, for example, or new to you in your work, how do you describe what you do? Because you do so many things.

James Altucher: Yeah, I don't know if I do describe what I do. I really like to pursue things that I'm passionate about and I've been a writer for the past 30 years. I've been an entrepreneur. I've started several companies. I've built and sold companies and then gone completely broke afterwards and had to always bounce back. And it's not pleasant. But that's something that I've written about. I'm a podcaster. I've had over a thousand podcasts and close to 100 million downloads. I'm an investor. I've been a standup comedian for the past six years.

I am currently obsessing on improving at chess. S I do a lot of things. I list those things with it because you shouldn't just list your career as the thing you are.

Chase Jarvis: I love that. And the fact that your passions play a role in each of those in the career side and the personal side and in the work side, career, work, hobby, all of that stuff is critical. Those folks who are orienting, they're either looking up right now and they're going, "Of course, I know James' work." So we're in their head and it is an interesting place to jump off we're two years into the pandemic now. And I would like to think we're emerging. That's still somewhat in question, but you wrote a year and change ago that New York is forever changed.

You wrote this post on your blog and, I think, in LinkedIn, you sent it around to all your different channels. It was a heartfelt earnest piece about why you went to New York or why one goes to New York because of the culture and the business. You can always trip over, I think opportunities, was something that was said in the article. You said the pandemic has changed that and will forever. This little known comedian named Jerry Seinfeld read your post and wrote back to you in the New York Times.

James Altucher: Yeah. As far as I know, it was his first op-ed ever. He took a whole page in the New York Times to trash me. I remember I woke up that morning, it was like a month morning or a Sunday morning and I was getting all these texts from people I vaguely knew calling me a putz. And I'm like, "Why is everybody suddenly using this like 1930s depression era insult to wake..." I don't even know these people. Then it turned out, I realized Jerry Seinfeld had written about me and written about my article.

What happens a lot is that I addressed serious problems that were happening in New York. Since then, no one has denied that these problems exist. The mayoral candidates, who some of them who I know very well called me for advice talking about these problems. But I think maybe it was the first time someone had pointed out that these problems could be more than just might last longer than the pandemic, and I think people got afraid, and maybe I wasn't sensitive to that. Like people, if you own property in New York City or if your family...

Look, my family is in New York City and I'm born and raised all around New York City. I lived there for my entire adult life. And it's a scary thing to be told this. A lot of people didn't even read my article. I'm not even sure, Jerry Seinfeld read my article, but felt the need to lash out. But the problems are real and I'm glad the incoming mayor is aware of them, and he's a good friend of mine.

Really the article was about, "Don't be in denial. These problems are serious. New York City is an expensive city to run. If your entire tax base is leaving, maybe you don't like the people that are the tax base, but you still need the tax revenues to support teachers, police, firemen, sanitation and so on. And 60,000 businesses were in danger of going out of business, did end up going out of business." So there's there's issues.

Chase Jarvis: Yeah. And I want to use our time here to talk less about those individual issues and more about what I think you are a master of, which is cultivating conversation, asking questions, doing things differently. The fact that you can very comfortably share your opinion out in the world in a very cogent, well-thought out constructive way as you pointed out, and I will attest. And that belief in what you're doing is genuine and real and honest.

That creates a response in the world, and where I would juxtapose that to someone else who had a sort of a half-hearted, conservative, don't want to offend anyone, or really uncertain of if their opinions will stand-up in the world or not. It's very different than James Altucher. What you did is you put your ideas out there in the world. The fact that Jerry Seinfeld did his first op-ed ever that it was in the New York Times and that millions of people, all of a sudden read your work, to me, that's the interesting part.

Not what Jerry said or not necessarily even what you said, but mostly why you said it, how you said it, the approach that you took. So I think it's an interesting overlay to your most recent book, which is called Skip the Line. In many ways that was a masterclass in skipping the line, right? How do you get the attention of millions of people around your ideas? Well, you did what felt natural to you. You wrote your bit of post and a lot of people happen to see it.

So if I'm making this connection incorrectly, then you tell me, but since I have a little bit of conviction and I believe this is a masterclass, ironically, in the book, Skip the Line, why don't you articulate a little bit of, is this standard for you? Because I've seen you do this over and over. This is like it's natural to you and that's what you're trying to teach us.

James Altucher: Yeah. And for better or for worse, it's standard to me because sometimes these backlashes are incredibly unpleasant and everyone says, "Oh, don't care about what people think about you." But of course, everybody cares somewhat, and it depends on the people too. But what's interesting to me is that, first off... Chase, we've talked about photography, you're a photographer, but from way back in our very first time together, I asked you, "How can one be a good photographer." And you said it best, "Take a photo of something that interests you."

You have to be interested in it first, what interests you. And for me, if I'm thinking a lot about something, I want to be able to express it and I want people to read it. So I might be thinking about something that I'm seeing a problem in the world or I'm seeing people what I think are making bad decisions. Or maybe I want to express what happened to me that you could bounce back from total bankruptcy and depression and suicidal thoughts and so on, and survive and flourish.

But a lot of times you have to always be able to say something in a unique way, and you have to say something that's unique. So whenever I write something, I don't even hit publish, unless I'm afraid of what people will think about me after they read the article. Because otherwise, if I'm not worried about that then I'm probably not saying something new. Then why say it at all if you're not saying something new? If I'm just a reading with the crowd, then what's the point of being one more voice in the crowd?

Now, that doesn't mean you try to be controversial. That would be bad writing as well. I could always tell if someone's just writing something just to be controversial. So I tend to write about things I'm afraid about. I love New York City. I was afraid people were in denial that New York City was in trouble. But more than that, there's a lot of cognitive dissonance that causes people to not want to hear that New York City is in trouble.

Maybe they own property there. Maybe they have a job that they can't leave. It's similar like let's say I write don't send your kids to college, which is another article I've written that had a lot of backlash. It's a huge financial decision to send your kids to college or to go to college and take on that kind of debt. So that creates cognitive dissonance. Once you do it, your brain is not going to say to you, "Oh James, you did something wrong." Your brain is going to reject the idea that college might be bad or home ownership is another one. That's one of the biggest financial decisions also you'll make in life.

If someone says to you, "Home ownership is no good," you're going to have a problem with that person. And intertwine with that, you can't just say, "Here's why I believe this X, Y, and Z." You have to tell a story. People only listen to stories, a photograph, a picture is worth a thousand words. A photograph is a story.

At the end of the day, no one wants to be lectured to. No one to hear a list of facts. Everybody wants to be entertained even from the things that they learn from. So you have to tell stories. So I write an article about, let's say why I hate owning a home, and I'll tell stories about times I've owned a home and lost everything and lost my home and so on. And then people are drawn in.

They're drawn in by the cognitive dissonance. They're drawn in by the story. They're drawn in when you're saying something in a unique way. So all of these things together creates... I hate to use the word viral. It does create an article that goes viral, but it makes people think. If I just said, "Oh, here's Kyle Rittenhouse, blah, blah, blah," It's nothing. I just joined this hoard of people shouting into a vacuum, and I don't like doing that.

Chase Jarvis: Let's look at it specifically to the lens of your most recent book, which I think you have, if I'm not mistaken 18 total books, is that right? Something like that?

James Altucher: Now, it's probably more like 21, 22.

Chase Jarvis: Okay. One loses count, even though one tries hard after 10. But Choose Yourself is the one that's quite popular where I really enjoy that one. And then this of came out, again, during the pandemic. And there's a through the lens that we've just been talking about, this idea of doing being uniquely you, doing things different, not just better. There's this undercurrent of one of the keys to continuing to evolve and grow and to echo the sentiment of the title, to Skip the Line to be able to go, this is not about a shortcut. This is how to authentically be catapulted to the front of any discipline.

You argue it's very much around uncertainty, being comfortable. As you said, "I don't know, if I'm not uncomfortable, when I hit publish, then I'm not doing it right." How does this combination of curiosity and discomfort play into what you wrote about and Skip the Line and your philosophy on life in general?

James Altucher: Yeah, it's so interesting because, look, you've created this learning platform and learning has been transforming so much in the past few decades. When we were kids, we would learn facts. Here's the first president. Here's the dates of the Civil War. Here's what happened in World War II. Fact, fact, fact. The reality is facts and information now are our commodity.

I can Google facts. I don't need to remember all of them anymore. But what real learning is, is that we're getting back to discovery. When you discover something new and you discover who you are in the context of what you're passionate about. And this is what you've been teaching in your platform. And Skip the Line is sort of about this, which is it's okay to return to your passions and learn them and even monetize them.

The pandemic make has accelerated this. Everybody was told, "Hey, everybody. Sit at home for a while and watch TV." Well, many people did not want to watch TV, they wanted to learn new things, go back to the passions they had when they were younger, and maybe even monetize them, as you were talking about. It's difficult to do because for one thing, everyone is out there saying, "You can't do that. You've worked hard as a rising up, as a marketing manager of a Fortune 500 company. You should stick to doing that and then retire. Then after you retire, you could play around with cooking or photography or whatever it is interested in."

Then everyone else says, "Oh, you can't do it. You need 10,000 hours. It's the 10,000-hour rule. You got to do something for 10,000 hours to be good at it," which is not really what the 10,000-hour rule says. And so I wanted to say, look, if you are interested and passionate about something, it's okay to pursue it. It not that hard to get in the top 1% of your field. You don't need 10,000 hours. You just need to get into the top 1%, not in the top 10 humans, but the top 1%.

Let's take photography as an example. There's probably a hundred million people on the planet who love photography and who consider themselves photographers. So the top 1% means being in the top 1 million of those 100 million. It's not in the top 10 it's in the top 1 million. My conviction is, is that if you're in the top 1%, you can monetize it in some way, whether you're a photographer, whether you blog about photography or podcast about it, or have a newsletter about it, or sell photography equipment. There's a million ways. We're just riffing.

So I wanted to write a book, how to quickly learn what you... How to find what you're passionate about, learn enough so that you're in the top 1%, which is not easy, but it's not as difficult as people think, and then how to monetize it. For writing, for instance, we were just talking about, "Well, how does a story get people's attention?" You learn in each field, what kind of the Skip the Line techniques are? "Okay. I want an idea to get attention. Well, I need to tell a story. I need to affect people's cognitive dissonance, and I need to be afraid. I need to make sure what I'm saying is unique, and with my own voice."

Those three things I can guarantee you almost any idea is going to go viral. Again, assuming you're passionate about idea. So one thing that I did during the pandemic was I decided this TV show, the Queens Gambit came out. It is about a chess player. I decided I'm going to use the techniques in my book and pursue chess. I'm going to stay disciplined to the techniques in my book. And it's worked incredibly well.

I just came back from a tournament. I won some money there and I did... I'll describe some of the techniques I use. So there's one I call plus minus equal. Find a coach who's better than you that could teach you. Find equals who you could play with and exchange notes with. And find a minus. Find people you could teach, because if you can't explain something simply then you don't truly understand it. So that's one technique for learning fast. I could go on and on. I'm obsessed with these different learning techniques.

Chase Jarvis: Keep going because this is exactly why we're here, James. The podcast is long form. Don't stress about our time. For example, I just made an entire podcast yesterday, which will be released in the next couple of weeks here about exactly that point. And the idea was in my brain from Skip the Line was something that I personally benefited from. So to retry out what you just said that when you're learning something, there are people who are further along either in the food chain or on their journey that have more information, more value. You can watch them. You can be mentored by them, learn their moves, having a set of peers that you can exchange these ideas with, people are doing the same things that you are at the same time, and those are ways to learn together.

If you can't teach it, as you said, then you don't know it well enough. What's better in this world than passing information on to others and building a community. That is factually effective. I've personally experienced it. You about it in your book. And you just demonstrated that fact with your chess example. Give us some more. This is like endless goodness for people who are listening right now.

James Altucher: Another one that's very important is what I call micro skills. So take entrepreneurship as an example. People say, "Oh, I want to be an entrepreneur. I want to get better as an entrepreneur." There's really no such skill as entrepreneur or entrepreneurship or business. That's not a skill. That's like a basket of skills. So you have to learn marketing. You have to learn how to have ideas. You have to learn execution. You have to learn how to manage people. You have to learn how to sell an idea. You have to learn how to create value in your business. And on and on and on.

You have to learn these different micro skills in order to know the kind of macro skill of business. I imagine with photography. What are the micro skills there? You have to know what is-

Chase Jarvis: Lighting, composition, communication. There's infinity skills.

James Altucher: And they're mutually exclusive. So knowing lighting is not the same as knowing composition. They're completely different.

Chase Jarvis: For sure.

James Altucher: You don't have to learn every skill perfectly, but if you know this basket of micro... If you identify the micro skills and then come up with a training regimen of how you're going to learn a little by little each day, you're going to be a great photographer. If you say, "I want to get 1% better every day of this year at composition." Well, 1% better compounded is 3800%. So I don't know... We're talking about something qualitative with quantitative words. So I don't know what it means to be 38 times better at composition or 38 times better at chess, but understanding that if you push yourself just a tiny bit each day and you know specifically you've broken apart the micro skills, you've broken apart, how to learn with this plus minus equal, and you will get good.

There's no question you'll be in the top 1% of your field. Then of course, there's the question of how to monetize. But for me, let's say for comedy. In 2015, I had set out the year I was going to write a novel. And then of course I got on a stage just for a fluke and did some standup comedy. I fell in love with it. I absolutely loved it.

So I put together my plus minus equal. I figured out what the micro skills were and that's by talking to people, but there's everything from writing a joke to acting out the joke, to how do you move around on the stage, to how do you use the microphone, to how do you do different voices? What are the different types of comedy like absurdism, storytelling, one-liners? And you start building this repertoire of micro-skills that you've learned, and that builds you as a comedian. But in everything also, it's discovery too, of who you are. So you have to answer this question, who are you? And that's sometimes a hard question to answer.

Why are you? When you say, why are you, what are the things that are important to you? Why do you exist? And then you have to also answer why now? So for instance, if you're photographing something, my guess is not only do you... Who are you is what you're interested in, what kind of photographs you want to do? Why are you doing photographs... There's a hundred million people doing it? Why are you doing it? What is going to be special about you?

Then why now? You're taking a photograph right now. There has to be an answer to the question at some point, why this photograph now is an interesting one for you? And this is another skill of asking these questions all the time means you're not just kind of following in the footsteps of those before you, but you're going one step further. You're bringing yourself into the history of photography and changing photography because of what you do as opposed to just following the greats before you, which is important as well, but at some point you need to take the step where it's you.

So for instance, with me with writing, I feel that over 30 years, I can say why me, is because I have my own particular perspective on building something, losing something, coming back from it. I'm really afraid to lose again and again. I've gone broke like five times. I'm terrified of doing it again. So this gives me my own particular voice, if I'm honest about it in writing. It helps me to see things maybe that other people don't always see when I tell my story in this way. So all of these things together help to catapult you, to skip the line, so to speak in whatever field you're interested in.

Chase Jarvis: The fact that you've repeated it so often in numerous disciplines is part of what's fascinating to me. Therefore, it's not just a skill set that's nuanced to one particular thing like writing. I think you've done it with cryptocurrency. I think you have done it with comedy, for example. And that these skills or this concept of lens that you put on this is extensible to numerous different areas of passion.

If I'm a listener right now, there's many reasons to care, but that's a big important one why Skip the Line makes a ton of sense. So you've repeated... Go ahead. Sorry, James.

James Altucher: Oh, I just want to mention there's one important thing too, which is this idea of experimenting, which I think is not familiar to the classroom we grew up in. So in the classrooms we grew up in, we get a book, we have to read it, we get it tested on it, we get lectured on it, and then we go home and we pass the grade. But very important for learning, and this is just as important in photography, as business, as comedy, as chess, or writing is you have to be able to do lot of experiments.

What's an experiment? An experiment is you have a theory about something that either you don't know or the world doesn't know, and you have a cheap way, it has to be very cheap of testing that theory. And the upside is enormous and the downside is you learn something. So like Thomas Edison, it took him 10,000 different wires before he figured out how to light a light bulb.

Someone asked him, "How does it feel to fail 10,000 times?" And he said, "Sir, I didn't fail 10,000 times, I learned 10,000 ways, how not to make a light bulb." I'm sure with photography, you could take a photograph of something. Let's say I want to take a photograph of a fruit. Well, okay, now let's do a little experiment. How about I look at the fruit through a microscope and take a photograph of a fruit that's so enlarged through the microscope that no one could tell what it is, but I'm seeing the innards of this fruit.

That might be an experiment done a million times, but I wanted to experiment just to see what happens and see what it looks like to me. Is it beautiful to me? And on and on. I'm sure while you were building up your photography, it's all about experiments, because that's how you find your unique voice.

In writing, okay, what if I'm going to write an article about... I'll tell you one experiment I did. That was a really great for me. I don't know if you remember like... It's like three or four years ago, Trump tweeted, "I want to buy Greenland." I think it was the prime minister of Denmark tweeted back, "It's not for sale."

I'm like, A, I didn't know you could negotiate and buy an entire country and do it on Twitter. And B, why was Denmark involved in this? I didn't know if Denmark had anything to do with Greenland. So I did a little research and it was fascinating. I figured out why someone would want to buy Greenland and that Denmark actually did own Greenland.

So I could have just written an article about what I learned, but instead I wanted to try a different format than just like, "Here's what happened and here's why this is important." So I started a Kickstarter where I wanted to raise $100 million so I could buy Greenland. I had never used Kickstarter before. You have to put together these, I guess, prizes. If someone donates $1,000 they could become a duke in Greenland. If someone contributes $10,000, maybe I'd give them 100 acres. If a million dollars, they could get a holiday named after them.

It was an experiment for me, and then you write the summary of why you want to buy Greenland and why this is important. So this has becomes a writing experiment. "Oh, I'm going to use, instead of writing this in the third person or the first person, I'm going to write this in the Kickstarter person."

So I learned more about writing. I learned about Kickstarter. I learned about Greenland. Kickstarter shut down my project because they knew I was raising money. I had raised already a couple thousand dollars and they shut it down and returned everything. And they reasonably did so because they eat the cost on the credit card fees when they returned the money. But I learned a huge amount.

Then I got another story about it which is telling that story. So for writing, you always want to experiment. Should you write this in the second person, the third person? Maybe write this in the form of two people sending letters back and forth to each other. But here was, I had never seen someone write a story in a Kickstarter format. So my downside was I learned a huge amount and my upside could have been, "Oh, I'm going to buy Greenland." But that's an example of experiment that made me an incrementally better writer and now I know Kickstarter.

Chase Jarvis: And you brought a lot of joy to it clearly, personally. I remember I was laughing in the background as you were introducing this because I remember reading that and saw that you had done that after the hilarious and buffoonery that kicked it all off with buying Greenland.

James Altucher: Here's another one. When I was first starting stand-up, I had two problems like every comedian might. What do you do when the audience is an hostile audience? It's hard to make people laugh when the lights are shining on you and the gun is to your head in saying make people laugh. You can't get enough stage time when you're just starting. So I went on a New York City subway and I figure you can't find a more hostile audience than a New York City subway during rush hour.

You have to make people laugh quickly or they'll totally hate you. So I had to work on my one liners. So I basically went on the subway and every stop I got off the train and went on to another car and did stand-up in front of the subway. It was scary. I didn't think I would do it. I even got on the subway and I thought to myself, "This is a waste of time," but I had someone there to videotape it, so I could study the video afterwards.

I did it. I don't think I did that great, but it was an experiment that put me in a high stress situation. I definitely learned about comedy. I definitely learned what I was capable of doing in a subway, just on the fly, and it was interesting.

Chase Jarvis: And it provides a backstory, as you've already said a couple times now for telling the story, like the story about I got anxiety first. A little micro twinge of anxiety just thinking about walking into a subway cold and starting to drop your act. That's very bold.

James Altucher: I got on there and I said to the video person, "I'm sorry, I wasted your time. I'm not going to do this." And then I said, "You know what? Just turn on the video anyway." As soon as my friend did that, I went off on a roll. I got some people to laugh. So it wasn't all bad.

Chase Jarvis: This idea of experimenting, you've talked about your personal failures, mentioned it several times in this conversation and in others, just building it all up. And you talked about going bankrupt, for example. Are these not just experiments that get bigger? And as you've done it a couple of times, the first time you lost everything and you came back, you're like, "Okay, that wasn't that bad. It was painful. I've learned some things and I know what I don't want to do next time." Is that in some way related to your passion for running these micro experiments? Is the subway experiment that you just gave in some ways analogous to your first bankruptcy say?

James Altucher: That's a really good point, and I haven't made that connection before. Part of experimenting is also a way of practicing failure in a very safe way. So take that subway example. Failure would be everybody yelling at me and saying, "Get off the subway. We don't want to hear you. You're awful." And that's it. That's the worst case. No one is going to kill me. No one is going to take my money or family away. I mean, when you go broke or fail in business... I mean, I've lost my home. I have lost my family.

There's all sorts of bad things, that can happen when you lose in a really big way, and it's really sad and horrible. When you experiment, it's like you're giving a chance to practice challenging yourself in ways that could be disappointing, but you get comfortable with it. And I'll give you an example, because this is six years after this subway thing.

Two days ago, I was in an airport and my plane was delayed not for like a half hour or an hour, my plane was delayed for 11 hours. So I was with a group of people. We were told don't leave the gate because we might take off at any minute. So every minute for 11 hours, we're thinking we could take off in another minute. And then finally they make this announcement. We found a crew except we're looking for a second flight attendant.

Everyone is yelling out and they're all upset. Everyone is yelling out, "We don't need a second flight attendant. We'll just go. Just put us on the plane." So I stood up and I said, "I am not leaving this airport unless there is a second flight attendant and she is handing me peanuts. That's why I pay to go on this plane." And people didn't know how to react, but then suddenly everyone starts laughing.

So I'm able to use this offbeat skill and stand up in front of an audience, which is something that I was scared to death to do years ago and make a tense situation a little calmer, not only for myself, but for everyone. And I enjoy doing that. But this skills translate into other skills. If you're good at chess, you might be good at analyzing business situations or handling the discipline to learn something, because chess requires a lot of discipline.

For instance, when we were talking about photography and I said, what if you do an experiment where you take the classic example of photographing a fruit, but then do it as if you're photographing it through a microscope. Well, combining knowledge of two fields is a good way to experiment. So let's say I use a microscope a lot if I'm a biologist. What are some techniques from being a biologist that I could bring into photography?

Or I've gone broke a lot, what if I take those experiences and bring it into comedy? So combining your passions and skills and interests is another way to bring your own uniqueness through, find ways to experiment and discover this unique intersection of skills that you have that make you the best in the world for those intersections. I think that's important as well.

Chase Jarvis: That is absolutely brilliant insight. Absolutely. I can personally attest to that on a number of levels. We'll use photography. I came from a world. My passion was the ski snowboard skate surf world because that's what I was doing. All my friends did that. I was living in Steamboat, Colorado. I was skiing 150 days a year. I was incredibly passionate about that. And in that community, there were people who were sponsored. You were sponsored by some ski manufacturer, sponsored by K2 skis and they gave you money to travel. They gave you all the equipment that you could use because you, as a leader in that particular genre of skiing were someone that people looked up to.

That seems very obvious, and perhaps in sports, this idea of being sponsored or endorsing something was normal. I was like, "Okay, cool. I'm taking pictures of those people. Why don't I try and do that in photography?" They thought I was crazy. I would see a picture on a back of a magazine of some photographer holding a Canon camera. I would speak to the person at Canon and say, "How much did this person get paid?" And they're like, "Oh, that person didn't get paid at all. They were lucky enough to get on the back of that magazine." I'm like, "Wait a minute. Bullshit."

So I set out to build a large audience. And when I had an audience that was large enough, I said, "Hey, camera manufacturer, in order for me to use your camera, you have to pay me." And that concept was so foreign in that industry. And guess what? Everybody is doing it now. Now, I'm not saying me alone can take credit for something like that. But that is a perfect example that mirrors what you just said of, I was experiencing something in one industry, thought I would experiment with to another. I ended up making millions of dollars doing that instead of a new pattern.

James Altucher: And think about all the skills you brought together for that. So first was your passion for skating and surfing. Maybe there was not that many photographers because they weren't getting paid. So there was nobody doing artistic photography in that area. So you're able bring that passion in, the passion for photography, your understanding of business and social media, and so on.

Combining those three things, of course, they're going to pay you. You're the best in the world now at the combination of photography, skate, surfing, and business slash social media. When people think of that intersection that became you. Stuff like that is really important. Again, I do the plus minus equal. I give chess lessons as I'm learning more chess.

I give chess lessons from a very entrepreneurship perspective. I've been an entrepreneur of many businesses. I give lessons to entrepreneurs and make all the analogies so they like, "Ah, yeah. Now, I see why you do this in chess. Now, I see why I do this as an entrepreneur, because all these things are connected." So that's my unique aspect is I'm not a professional player, so I can't really teach in that sense, but I teach from the sense of being, "Hey, I'm an entrepreneur chess player. This gives me a good platform to teach on," and so on.

Chase Jarvis: My point in sharing my experience with that is if you're listening right now and you have the areas of interest of photography and you're a biologist, let's go back to your photographing something of fruit and I bet, if you actually looked through a microscope and were able to capture an image and you've shot images of oranges and apples and watermelons, you could make some beautiful shit. There's probably at some level, whether it's what the eye can see or deeper at the cellular level, there's beauty.

I could see an art show right now, this is like watermelon, and orange, and apple. It would certainly be extraordinary. That is a great example of right now whoever's listening, watching, what are areas. This hearkens to the point that you are a master at James being uniquely you leaning into that. You have a set of experiences. Every person listening has a set of experiences that are unique. And if you can combine those in interesting and unexpected ways that is part of the expression of you. I couldn't help, but take that away from Skip the Line, James. The point was so well made.

James Altucher: Yeah, thanks. It's really important to me that concept because let's say... Again, it's very difficult. I'm 53 years old. It would be very difficult for me to be the best photographer in the world. Maybe I could be good, maybe I can't. But I know being in the top 1%, if I worked at it and I studied it and I did it, it would take me a while, but I could do it. But the only way to really do something new is if I'm bringing my own perspective, if I discover something new. So what do I have in me?

Well, I can focus on people who have been broke or entrepreneurs or photo photographing comedians or chess players. These are all intense type of activities that take a lot of blood, sweat and tears. I imagine photography in those areas might be interesting or I don't know. There's so many ways to combine who you are with those passions so that whether or not you're good... No one can tell if someone's 20% better photographer than someone else. I would not be able to tell. But I can tell if someone's bringing something unique to the table. People value unique more than better.

Chase Jarvis: There's a phrase-

James Altucher: I'll give you an example that applies to not only my own experience, but one of my daughters. So she was having trouble getting into college, and I actually am against kids going to college and she's aware of that, but whatever. She was having troubles getting in. I said, "Look, why don't you take a year off? And everybody who's applying to these colleges, they all have a 4.0 average. They've all done charity work. They all played in a sport in their school and they were in a lot of clubs. There's nothing unique about that. And if you have a 4.2 GPA, it doesn't make a difference to a 3.9 GPA. Take a year off, figure out what you like doing, and let's do it."

So I suggested a bunch of different things and one that she chooses, I sent her to race car driving school. There's very few female race car drivers. I could think of Danica Patrick and that's it. So she went to a race car driving school. She got a professional race car driving license. She participated in a couple of races. Then when she applied to college a year later, she's a professional race car driver. How many girls applying to your school are professional race car drivers. She got in every single place that she applied.

So that type of thing too, when you look for what's unique and you experiment and you try things and you try what you're passionate about, that makes you unique. Don't try to be better, just try to be unique and say things with your own voice. Be the person who wakes people up when they see who you are and what you do.

Chase Jarvis: There's a phrase that has been a part of this show for the 11 and a half years it's been running and that's, "Don't just be better, be different."

James Altucher: It's so important.

Chase Jarvis: Literally, that has been a pattern, a phrase that has been uttered every half a dozen shows for 11 and a half years here. Different is the better you've been looking for. You've just given us a very specific example. That example of your daughter, by the way, extraordinary. I'm going to use that and I'll tell it authentically as you have here, because I'm making notes to myself as you're saying this, because it's the perfect lens. That approach to life to me is so affirming because what do we all have? What does every single person who's listening to watching have? They have, if not lots of other things, they at least have their own experience. When you start to understand that, that's what people and culture and... That is interesting. Again a 4.11 or a 4.12 GPA, that is not interesting.

We are told that that's what's interesting because we are raised in an achievement culture where that is where it's something that's applaudable on a chart, so it's easy to talk about being a 4.11 is better than a 4.10, and yet the example that you've just given, that is how the world actually operates. We tell people to go to college, the most celebrated... Many of the most celebrated people in our culture dropped out of college.

Bill Gates, Steve Jobs, these are people who started college and said, "I'm not being..." I'm not saying that college is not for some people. It will be great for some people, but it's ironic that the most well tried path says that's what you do, and then you look at the people in our culture. Jon Bon Jovi, Steve Jobs, Daymond John. I don't care background, socioeconomic status. Be uniquely you. Be interesting, be different. There is room for that.

James Altucher: Yeah, and that's why it's so important to let your passion be somewhat of a guide as to what you should do next in life. And by the way, you don't have to just do one thing. You could work as a marketing manager and pursue your passions. Maybe you're passionate about marketing. I don't know. I shouldn't make assumption, but sometimes I look back and I say, "Well, okay. I just spent the past five years doing this, whatever this is. Maybe I should have been in Silicon Valley and hanging out with everybody and I could have gotten in that round of Uber or whatever."

But you can't look at that way. I really have enjoyed every single thing I pursued. And by the way, when you pursue something that is interesting to you, it's not that it makes you happy because... Let's say your passion is tennis. You're not going to be happy most of the time, while you learn tennis, you're going to lose most games you play. It's hard to learn something to get out there and study and learn and fail, and fail, and fail. But it'll give you wellbeing.

One of the components of wellbeing is mastery. When you start to master something, you get an enormous dopamine hit from it and it just feels good. Then when you bring that mastery into other disciplines, well, A, you have learned the language of mastery. This is how I master something new. And B, it gives you this buffer that you know who you are. Well, I know I can get good at things. I know I'm good at business, or comedy, or chess, or writing.

Nobody could take that away from me, because that's something internal. So you don't necessarily do something to be happy, but you do something because you love it no matter what. And chance are, it's going to be so challenging. You're not going to be happy most of the time. So that's a big misconception about doing what makes you happy. There's a subtle of friends, but it's more like doing what you love.

Chase Jarvis: And in that subtlety, there's some profundity too. I think you hit it spot on. James, I didn't know that... These are philosophies that you're sharing on the show that you're just like hand in glove with things that I've believed my whole life. I've read most of your work and it's interesting to me that I'm really just hit me like a ton of bricks here. There's so many of the things that you've articulated in this conversation are things that I will go to the grave with that I have that have been a part of my psychology ever since I started trying to leave that path that other people have tried to lay for us.

These are people who care a lot about us, right? Your parents, your teachers, your career counselors. These are people who try and steer you the right way. Let me ask the question. So how does one in the face of all this pressure, because let's face it, not many people's parents are saying, "You know what, you should go be a rock star. You should go try and be a professional gamer. You should go be a stand up comedian." So what's the advice that you have for people who are listening? And maybe it's one's spouse. You shouldn't go try and be a professional YouTuber at age 53 because our family needs you to pay the bills, for example. So how does one make the decisions that you're encouraging people to make now in the face of real consequences or people who are not attuned to this universe of which you speak.

James Altucher: Yeah. It's a great question. Particularly, if your spouse is saying, "Listen, we need to pay the bills. We can't just downsize. So you could pursue comedy because very few people make money. There's not that many people filling out stadiums in comedy, or even being a writer or being a photographer, or any of these things. Anything that's attractive to the population that's hard to monetize. So again, I think the key is experimenting and start off small.

Okay. I want to learn chess. I'm going to play online. I'll play online for... I'll take a lesson once a week. I'll play online, maybe a couple hours a week. You know what, when I play online, I'm going to turn on Twitch and I'm going to stream it. I'm going to try to build up my skill as a streamer, which is a hard skill too.

I have to be able to talk while I'm playing and be entertaining while I'm doing something. I have to do two things with my brain at the same time that are both difficult. These are little experiments. By the way, all of those things, I listed cost zero and take a modest amount of time. So do that for a few weeks, months, whatever. See what the results are. That's an experiment. Nobody will deny you that experience.

Now you could also say, "Well, screw all the people who say I can't do something. I'm going to show them." But that won't necessarily make you better at something. So you could take in all the input, but you could still design experiments that are worth doing, that'll change you as a person and there's really no downside and there's enormous upside.

So for me to try stand-up comedy, who was going to... Everyone could tell me, "You can't do this," but no one can stop me from just going up on a stage and trying to tell jokes for a while. No one could stop me from bringing comedians on my podcast as a way of getting them to mentor me without realizing it because I would bring a comedian on and I would just ask, "What if this situation happens to you?"

I would just be talking about what happened to me the night before. What if there's a drunk woman who's heckling you? And I would learn valuable things like, "Well, you can't... Be careful with a drunk woman because the audience might be on her side. They don't want to see you making fun of someone like that." And on and on. You learn little tips. And these are all just experiments.

Even with chess. "Okay. I did my plus minus equals. I did my micro skills, and I played online, but I hadn't played in a tournament in 25 years. 25 years ago was the last time I played in a tournament. So what does it hurt to play in a... I'll find a local place, a Friday night. I'll play in a small tournament, see what happens." "Oh, okay. You did well." "I'm going to now play for a weekend in some place." And on and on. You just try experimenting.

And that's kind of a way to ease into something. What about entrepreneurship? Well, don't just have an idea and raise $2 million for it. Is there a way to experiment with it? Is there a way you could do this service that you were going to automate? Can you do it manually for a while and get one of your friends to be your customer and see what they liked and what they didn't like. Would they be willing to pay?

That might be an experiment to do. You could have done for Chase Jarvis online, you could have called some of your friends and said, "Let's do some videos. We'll we'll just put it up on YouTube. We'll call it chase Jarvis Online and see if there's interest and more. See if the feedback is good before we raise $10 million and try to make this a full business without really knowing if it's going to be good or not."

All businesses should start as an experiment by the way, because before you start a business, you have no way of knowing if there's going to be demand or not. Unless you buy a laundromat, which has kind of a built in demand. There's no other way other than through experimenting, whether you're going to know if you're going to have demand.

Chase Jarvis: I'm going to ask the reverse psychology here. Again, let's go back to Skip the Line because I really encourage people to pick up a copy of that. If the premise of Skip the Line is running these experiments and living your life or planning through this lens that you've been sharing, what are the downsides? What are the unexpected pain points that one might encounter in following your advice?

James Altucher: Well, there's a lot and some are unfortunate. For instance, if you're a writer and you're a writer like me where I tend to write things that I think that might... I don't try to be controversial, but again, I don't want to say something if everyone else is saying it. I'm going to write about things I'm passionate about and tell stories around it, but it might be some things that bother some people like this New York City article.

You're going to gain some friends and you're going to lose some friends. You're going to gain some family and you're going to lose some family. All of these things have happened to me and sometimes it's really painful. You can't believe I thought this person was my family or my friend. And you have to be able to accept that. If you're going to be different in the world, some people are not going to like that.

Some people are going to be threatened too. If you want to be a photographer, previously you were a lawyer, other lawyers might be threatened. If you suddenly become a successful photographer, they might hate you for it. They might not say that they hate you for it, but they'll find some other reason to hate you. So there's that downside.

The other downside is of course to do... It's like what we said earlier, to do anything challenging, you're going to be miserable some or even much of the time. If you're going to try comedy, you're going to bomb on stage. And if you truly care about it, you're going to hate yourself afterwards. You're not going to be able to sleep that night. Or if you play in some competitive area or if you want to be a professional investor, there's going to be days, weeks, months, you lose money and it's not going to be... And you're going to think to yourself, I thought I could be good at this.

Stuff happens and sometimes you figure out like, well, some strategies don't work or sometimes you're going to lose money or sometimes you're going to fail a tennis or chess or whatever. It's very disappointing. It's very, very hard to pursue something that's difficult. There's a psychology to it. Ultimately, you have to be able to convince yourself that every time you fail, these are the only times you learn. And people say, "Oh, I failed at a business. This must mean I learned something."

No, you have to do a full autopsy on why you failed otherwise you won't learn anything. But it's very important, the flip side. Let's say you tell all your friends, "Oh, I have this business idea." And they all say, "Oh, man, that's a great idea." You have just learned nothing. People tell yes to you for lots of reasons. People will tell no to you for only one reason is that they legitimately think that's a bad idea. But they'll say yes to you because they just want to get you away. Like, oh, he'll go away.

If I say, yes, that's a great idea. Or I don't have to insult him if I just say yes. So there's a lot of reasons why people say yes to things. Yes or success, give you no actual information. When I play a game of chess, if I win, I have no information about my skill or ability. If I lose, I could look at that game and figure out what was going on in my head when I made that bad move that caused me to lose?

Now, I have real information that I could work on. When I did comedy, I would take a video, I'd watch the video afterwards and I would say, "Oh, I could see why people didn't laugh at this point because I said uh or I stuttered a little bit. Or I moved just in a little weird way that I could tell didn't connect with the audience." If everybody's just laughing all the time, I learn nothing. So while at the same time failure or lack of success is very painful... My first chess tournament that I played in, in 25 years, it was... I was a great chess player 25 years ago, but you lose skill if you don't play for a long time.

So I played in this tournament and I had five losses and three draws. It was eight games. I didn't win a single game. I'm like, I have never... Since I was a... I have never had an experience... I was horrified like this is horrible. I had never had a tournament like this before in any area of life. But I realized, okay, this is a treasure trove of information now about why I lose. There's only upside. It's Been Down So Long It Looks Like Up to Me is a famous 1960 novel. There's only upside from here.

A month later, I've studied maybe four or five of those games. I have almost a hundred pages of notes on these games from studying them. If I had one, I would have zero pages of notes. So painful parts have upside, but you have to... It takes a psychology to learn that because it's going to feel bad while at the same time, you have to tell yourself this is a good thing.

Chase Jarvis: This has been an extraordinary conversation. The last topic I'd like to explore is very related to what you just said. I was asking... My notes were here to explode this as a final topic, but it couldn't have come together more eloquently because what you just said reminds us that your mindset in these moments, this sort of willingness to experiment, to review your experiments, to learn, to be made fun of for either failing or for being so obsessed that you're taking 100 pages of notes about your chest tournament.

Both of those things are weird, right? But this idea of willing to be weird or different or unnatural or obsessed or any... There's a whole host of ways we could describe it, has so much to do, so much reliance on mindset it seems like. So I'm curious if you could talk a little bit about mindset. Is there anything that you do to program your mind other than just what you've talked about here? It seems like there has to be some layer because to be able to withstand those funny criticisms and to be willing to be laughed at on the subway when you're trying to produce stand-up comedy in the moment.

Are there things that you'd do to fortify yourself or to strengthen your mindset, or to reengage the belief that you have in yourself? Or is it just part of the process to have all those darts thrown at you and you get good at being tolerant and move on?

James Altucher: It's a little bit of both, because no matter how long you've been doing something, you're going to be negatively affected and have negative thoughts some of the time. When I wrote this New York City article and Jerry Seinfeld responded, to be honest, so many people were then saying, "Go, Jerry." Andrew Cuomo sent out an email to 10 million people about Jerry Seinfeld's article trashing me. De Blasio, the mayor of New York did a press conference about it.

So many people were unfriending me on Facebook and I didn't know why. I had good intentions. And I was in comedy. Seinfeld was like a hero of mine and a lot of comedians worship Seinfeld, comedians that I respect. So I was starting to get negative feedback from this subculture I had been a part of.

I broke down and cried at one point. I didn't understand what was happening. You're going to have those bad moments, but you always need to step back and say, "Listen, it's the who are you? Why are you? Why now?" You're doing something for a reason. And it could even be a bigger reason. Am I playing chess because I want to be in a chess magazine and, "Oh, this guy got a certain title or whatever"? Or do am I playing it because I just love it and I want to get better?

A lot of times we convince ourselves, "Okay, I want to be a photographer because I want all my skating friends to look up to me as a photographer and then I want to make money at it and be famous for being the first..." So that's kind of like an external motivation, but ultimately you have to step back to your internal motivations. Like I love this. I want to get better. It doesn't matter where I rank in the world of this, but that's my first motivation.

Then you have to say, "And this is important for me. I'm telling me this more." And this is a cliche, but you have to be grateful that you have the opportunity to do this. However, it is, you don't have to be rich, poor, but you've carved out an opportunity to do something you love, that's something to be grateful for. Then all of the, "I'm grateful I have a support system around me. I'm grateful, my friends who stuck with me. I'm grateful..." All the cliche things.

Mindset is incredibly important. If I go into a game of chess thinking, "Ugh, I suck. I'm going to lose this game. I'm tired. I'm not feeling well." Or if you go in and you... I tried this actually. I tried this, this last tournament. It worked really well. Between every move, I would look around and I would look away from the board and I would think of the things I was grateful for. Because then when I look back at the board, it gives me a whole new perspective. I'm not sucked into whatever mindset I was in before, even if whether it was good or bad.

And that was incredibly useful because mindset, you're never like at this... Let's say photography skills rang from one to 10 or one to 100, and you say, "Well, I'm at least an 85." Well, you're not an 85 all the time, you're always a range. You're from 65 to 90 maybe. On a good day, you're 85, but on a bad day, you're 65.

So mindset's a big part of where you're going to end up on that spectrum that day. What really helped me the first time I went broke, what really helped me was I started writing down... After two years of depression, I started writing down 10 ideas a day on a waiter's pad. I don't know what happened, but after two or three weeks of that, I started seeing possibilities in my life. Like the ideas I was writing down were like, "Oh, here's 10 books I could write. Here's 10 businesses I could start. Here's 10 ideas for Chase for his show. Here's 10 ideas for Google."

Suddenly I felt like more creative because I was exercising that creativity muscle and it just allowed me to see possibility. As long as you could still see possibility, you're going to have a positive mindset. I think that is really important for performance so that you're at the upper end of your range and the spectrum of your ability. The idea of seeing possibility and finding confidence that you'll always find new possibility in what you're doing.

Chase Jarvis: Brilliant. Again, we've talked about a lot, your book that we were originally going to talk about this more than a year ago came out last February. Congratulations on the success. Skip the Line: The 10,000-

James Altucher: Thank you.

Chase Jarvis: ... Experiments Rule and Other Surprising Advice for Reaching Your Goals. Aside from the book, where would you steer people who have been intrigued by our conversation and want more? Where do you want to send them?

James Altucher: I don't know. Like you mentioned, there's the book, Skip the Line. I wrote another book, Choose Yourself, which was very popular and it has similar themes and talks more about when I was going broke and stuff. I don't know. Lately, I've just taken a break from social media and all that kind of stuff. I got a little burnt out, I think, on social media.

Chase Jarvis: Understandable.

James Altucher: Just Google me. You'll find me. You'll find me on The Chase Jarvis Podcast. Listen to our earlier episodes.

Chase Jarvis: I've got some great ones in there for sure. I want to say, thanks again, James. It's always a treat to speak with you.

James Altucher: Thank you.

Chase Jarvis: So this was particular light bulb for me, all of the ways in which our thoughts are similar. Thanks for showing up and continuing to inspire and be so vulnerable. It's really, really impacted me. And I think the show is going to be a doozy. So let James know when you watch the show that you appreciate it and him. We're always out there listening. James is not because he's taking a break on social media, but I'll be paying attention. In the meantime, thanks again, James and signing off to everybody out there on the internet land. I bid you adieu.

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