in: Behavior, Character, Podcast

• Last updated: September 28, 2021

Podcast #149: Taking Action in an Uncertain and Hack-Focused World

Three of the best and most popular pieces of content we’ve ever published on the site are 10 Overlooked Truths About Taking Action, 5 Tools for Thriving in Uncertainty, and Stop Hacking Your Life. While each was published months to years ago, I still get tweets and letters from men saying how much they appreciated the articles, and how they inspired them to adopt a better mindset and take more action in their lives.

Those 3 pieces all have something in common: they were written by a fella by the name of Kyle Eschenroeder. Kyle’s one of the most interesting guys I’ve ever had the pleasure of meeting online. He started day trading in high school and now he runs a successful company called StartUp Bros that help individuals with their e-commerce businesses. While that’s all really impressive, what impresses me most about Kyle is how well-read he is and how earnestly he grapples with a lot of hard ideas. He’s extremely thoughtful and I love how we tries to connect all these disparate ideas in creative and useful ways that are relevant to navigating our current culture and its unique challenges and opportunities.

Seeing how Kyle’s posts have really resonated with AoM readers, I thought it would be great to get him on the podcast to discuss some of the ideas he’s explored with us. So today on the show, Kyle and I have a conversation about action, uncertainty, and why life hacking is overrated. Lots of great takeaways from this show. You’ll want to take notes.

Show Highlights

  • How studying philosophy made Kyle a better businessman
  • Why you should never forget to play the long game with your business
  • How to transition from starting something to maintaining it for the long haul
  • Why managers are just as important as the start-up entrepreneur
  • Why passion and motivation follow action
  • How planning can get in the way of taking action (but why it’s still important to plan)
  • Why you should develop systems instead of goals
  • How to create a more antifragile life
  • Why you should be taking more small bets
  • How to tell when you or a company have run out of good ideas
  • And much more!

We recently published a book with Kyle called The Pocket Guide to Action: 116 Meditations on the Art of Doing. Grab a copy for when you need to refocus on taking action.


Brett McKay: Brett McKay here. Welcome to another edition of the Art of Manliness podcast. If you’ve been reading the site for a while, you’ve probably seen some content written by a guy named Kyle Eschenroeder. He is a business owner, owns a company called StartupBros where he and his partner train individuals how to start their own online business, but besides being an entrepreneur, Kyle reads deeply and he thinks deeply about a lot of important topics on how to live the good life.

The two pieces of content that he has written for the Art of Manliness that have resonated with a lot of readers was the first one is about the miss of taking action. It’s about the excuses we tell ourselves that prevent us from taking action we know we need to take. The other one was on how to thrive in uncertainty, taking on this idea that in modern life, we’ve deluded ourselves in the thinking that we have more control over our lives than we think we do. There’s an app for that mentality. With a click of a button, you can solve a new problem. The reality is there are some things in life that we just have no control over and the trick is figuring out how to create a life that not only can survive that uncertainty, but can thrive in it, and that is what that article talks about.

I brought Kyle on to the podcast. I want to discuss these topics in detail and get really deep into it. That’s what we’re going to do today. Really great conversation, I think you’re going to like it. So, without further adieu, Kyle Eschenroeder on Thriving in Uncertainty. Kyle Eschenroeder, welcome to the show.

Kyle: Thanks for having me, Brett. I’m looking forward to it.

Brett McKay: You’ve contributed some articles on our site that have really impacted a lot of people. We get emails about them all the time. We’re going to talk about some of the themes you’ve written about in these articles. I’d like to really have this discussion with you, but before we do, let’s talk about your background because it’s really interesting and pretty unconventional. Can you tell us how you became this philosopher/entrepreneur guy that you are?

Kyle: Oh, man. I’ve always read deeply. I think I started day trading under a mentor in high school and in order to do that, it’s very emotionally trying. Getting into meditation and philosophy is a natural progression for anybody who does that. I went to college and continued to trade and started to dabble in startups. I got involved with early on and really was excited by the potential in value creation that a startup can have. It seemed to me one of the best ideas, these ideas that I was studying as an extension of trading, you could really have a bigger effect in the real world through startups. That’s where the entrepreneurial part came in.

Really, early on, it was more self-development, focus stuff, and self-help stuff, and I think if you read enough of that, you start to question their premises and realize that they haven’t really, and I say “they” broadly, but you need to look at maybe why you’re doing something. What’s at the core of this? What need is this fulfilling? That is where you get down into more, I guess, intense philosophies.

Brett McKay: Is that what got you in the researching, studying, and writing about philosophy, just trying to find some balance to the uncertainty that you find in startup culture and day trading? Is that what it was?

Kyle: Yeah. I think it’s a great balancer, but also a driver. If you’re just going to be an entrepreneur and that’s the only thing you’re focused on, you’ll still create value, but you don’t have a solid of a foundation or perspective on what you’re building, this society that you’re building it in, and how you can kind of do the most good.

Brett McKay: You can read this personal development books. A lot of people do. I do. They’re often very practical and there’s always the bullet point list of thing you can do right now to apply to your own life or to your own business, but how does studying things like the uncertainty principle or Nietzsche, or Seneca, how has that made you a better businessman in your day-to-day talking practical brass tax level?

Kyle: I think these things give you a great grounding in dealing with people and in dealing with struggle gaining perspective. Honestly, Brett, there’s a lot of entrepreneurs who don’t read a lot, who don’t have a strong foundation in Nietzsche who are much better entrepreneurs than me. I think of Steve Jobs. I think of John Rockefeller. These guys are famous for reading very little. Carnegie barely read. I think it depends on what you’re doing.

In the businesses that I have been involved in, I deal with people a lot, and for me, it’s very important to have an understanding of where I’m headed. Everyday I can communicate to people more directly kind of vision and how we sit as a company, in the community, in our society today, the good that we’re doing, maybe more fully than somebody who hasn’t read as widely, but I do hesitate to say that as far as an entrepreneur creating ROI, I don’t know that it has a direct impact.

Brett McKay: Let’s talk about that because I love how you as a businessman. You’re thinking of the bigger picture. Oftentimes, there is this cult of the startup in internet businesses where it’s just about making enough money for yourself so you can live the dream, travel, be location independent, right?

Kyle: Uh-huh, oh, yeah.

Brett McKay: My question is how do you get past that where there’s this filter bubble, whatever we’re just talking about. “Okay, here’s what’s about me. Here’s what can I do for me.” How do you see startup cultures and businesses taking on a bigger approach and actually having effect on the community around them?

Kyle: That’s a really interesting question. I think it maybe a natural cycle and that’s what I’m hoping on, is that this kind of obsession with location-independent entrepreneur is almost wearing itself out, exhausting itself, because there is so many people who have accomplished that now who are, they are empty, they realized that this is not the best way. They realized it’s not as easy as four hours a week. It takes full time commitment. You take on massive responsibilities.

Also, once you hit a certain level, you realize that the only way that you can be fulfilled is by helping other people truly not in the kind of empty way that many of these businesses go about it. Honestly, Brett, you can look around at the businesses that sustain themselves. Very few of those get a business up and running so I can create half and income and then forget about it and go live my life in, I don’t know, Hawaii or whatever.

I’ve watched a lot of them. This whole kind of group of people just throws stuff up and it fizzles out immediately. The only people that have staying power to be true entrepreneurs are ones that do want to create something that’s bigger than just them. As much as we want to talk about it, as much as entrepreneurship can be broken down into steps or made systematized, it’s always hard.

Business is one of the most abstract things you can do. It’s extremely difficult to create something lasting and unless people have that kind drive to do something bigger themselves, it’s not going to last. I guess my answer to you is I think it’s taking care of itself.

Brett McKay: Nice, sort of like natural selection.

Kyle: Yes, exactly.

Brett McKay: That brought up an interesting point. One of the things I find about people who are into entrepreneurship and startups, they love starting things, and they get really excited about starting new projects. I have some acquaintance who call themselves serial entrepreneurs. They’re always starting something new. It’s always exciting to start something new, but if you’re that type of person who loves to start things, how do you make the transition to, “Okay, I started something. It’s gaining momentum. It’s got some teeth,” how do you transition to managing and maintaining that business for the long haul?

Kyle: That’s why you have two options. This happens at every level, from people starting blogs to people starting companies that end up being valued at billions of dollars. There comes a point when you decide to become a manager or to leave the business. Once you develop a business … This has happened with StartupBros, the company that I started with my friend, Will. It has gotten to the point after a couple of years that it’s taken on a life of its own.

We’re no longer a startup. We’re now managers. We’re now managing growth. We’re now feeding this separate thing that has its own life now. There’s less freedom in it. It’s a completely different mode, and so, you have to either decide whether you want to switch modes, whether you want to become a manager and deal with the grind, or if you want to go look for the next start-up opportunity.

Like I said, a lot of startups since Silicon Valley, investors pressure these start-up CEOs at a certain point to either they need to leave or get trained in serious management, and it’s not a transition everybody can or wants to make.

Brett McKay: Maybe this is just me. I feel with this whole start-up culture where startups are really sexy, it’s fun, you get the Nerf guns at lunch and you get food cater in, I feel management part, right? It’s de-emphasized. People who their talent is telling people how to do things efficiently and getting things done, and maintaining the momentum that a start-up person to start, they’re like the unsexy dork at the dance who hides in the corner, but those people have incredible value.

Kyle: Yes, and I think you’re pointing out something that I like to call the sexy tax that you pay. If you want to do the thing that’s being celebrated by culture, you have to deal with generally decreased returns and increased competition. A start-up culture, it only celebrates a very few young billionaires or down the other side, it celebrates these teenagers that are all starting businesses.

I’ve been involved in this start-up shows and we actually get approached by these television studios, these production houses that are trying to launch startup, the real world of startups basically, and everyone fails because the highlights are, like you said, it’s the very beginning. It’s initial exciting ideas, and then it’s the idea or when you sell to Facebook or Google, but everything in between is just agony.

It’s just sitting at a computer typing, programming, desperately trying to sell your services. It’s boring and it’s a, like you said, it’s not exciting. When people have this Hollywood idea of what it is to be a start-up entrepreneur, they act on this abstract ideas that they have of what an entrepreneur should be instead of actually focusing on what does my business need from me today? How do I build this thing into something real? How do I provide value? Those are the boring questions that nobody is going to make a show on, but those are the things that actually grow businesses.

Brett McKay: I’ve encountered this paradox or this problem my own life. In my backyard, I have some land, so I decided to build a trail through it. It was really, really fun blazing the trail. I have this awesome machete that I was cutting through all the weeds, the fizzles and the thorns, and it was great to see my progress.

Then, winter came and I didn’t go out there. Then, I came back in the middle of the spring and it was all overgrown. I was like, “Crap, I’ve got to maintain this thing now.” Maintaining it is not fun at all.

Kyle: Right, and that’s what you have to do for decades. It takes about a year to build the thing and that’s exciting. You get to see progress. Then, the rest is just fighting off decay entropy.

Brett McKay: This is just isn’t something that applies to business, but also applies to someone with their personal development. It’s always fun to start a new goal. “Oh, yeah. I’m going to go to the gym. I’m going to start journal writing. I’m going to be awesome.” Then, you get into the grind, and you’ve got to keep doing it.

Kyle: Right, and that’s where the payoff … The payoffs only come after that grind, after that getting through that super boring plateau where you get to the next peak of whatever.

Brett McKay: Let’s talk about one of the articles you wrote for us last year. Today, we still get emails and letters about it. It was 10 Overlooked Truths About Taking Action. A lot of people talk about taking action on the web; deeds not words, carpe diem, take action, blah, blah, blah.

Kyle: I think they write that in their Facebook profile.

Brett McKay: Yeah, exactly, but people still have a hard time taking action on their intentions, their goals, their dreams. Why is that? Why is it so hard? You feel really motivated at the beginning of the day, but taking that motivation and actually turning it into action is really hard for folks.

Kyle: That’s the tough question that I can’t really answer and I don’t think anybody really can or maybe even should. There’s an infinite amount of good reasons, probably, not too good rationalizations. One of the most interesting ones I came across recently came from Mark Manson. He calls it the Manson Principle that we don’t do things that threaten our personal identity even if it would make us better. We have this homeostasis, it was a term from Ludwig Sandstrom that it sticks us where we’re at. There’s an infinite amount of forces hitting us from different directions.

I think my suggestion and what the article is attempting to do is to trick us out of pointing out these reasons and tricking ourselves to take action anyway. Freudian, one of the psychoanalyst, have had a pretty terrible success rate in fixing people because they are so obsessed with finding these hidden causes, and a lot of times, it might be more helpful just to forget about them, not worry about them. That’s where I think we should try to trick ourselves into taking action even though it feels like there might be reasons not to.

Brett McKay: What are some miss that people have about action?

Kyle: I think one of the most interesting ones to notice is that people believe things like motivation, passion, purpose, courage, reasons, justifications, or even planning always must proceed action when in fact, all these things more naturally follow action. It’s very, very difficult to believe because we’re so wired to believe the opposite, but once we can wrap our heads around that and once we prove that to ourselves, it becomes extremely easy to take those actions that we know we should.

Brett McKay: You see that again and again on the internet. Everyone is always talking about you got to follow your passion, find your passion. People even put up the means on their Facebook profile or Tumblr. They have their totem animal versus “I’m the gym beast. I’m going to be awesome,” then they don’t do anything. They don’t go to the gym.

Kyle: If you notice this, it tends to be the most out of shape people who know the most about fitness, who know the most about exactly what exercises to do to get X results. They tend to have this extreme book knowledge, but then, just forgot that kind of vital part that means “go to the gym.”

Brett McKay: Go to the gym and get started.

Kyle: Yeah.

Brett McKay: You see this not just in business, but with their personal development. People have these goals and they feel like “If I want to lose weight, I’ve got to get motivated, and once I get motivated and I feel like it, then maybe it’s going to be a breeze,” but that’s not how it works.

Kyle: Right, and “I need to get motivated and I need a perfect plan.” Once I have just this perfect plan and the perfect outfit, and the perfect gym partner or whatever, then, I’ll do it, but it never happens. Any of those people who get, if they have a friend that’s good enough to drag them to they gym for a week consistently, those people are motivated. All those abstract barriers to entry have been deleted and they understand that it just means going to the gym and sweating.

Brett McKay: Stephen King is a great example of just doing it. You don’t have to be motivated. You don’t have to have the perfect everything. He just wrote. When he wrote Carrie, he was living in a really small house and he would just write on the kitchen table in the corner while his wife was banging pots and pans in the kitchen, and it didn’t matter. He wrote the book.

A lot of people think, “Well, if I’m going to start a business or write this blog post, I need to do my ritual. Here’s my little thing that I got to have and this got to be perfectly set up, and I have to have my headphones and my background music, and my binaural beats, and then the motivation and the inspiration will just come.”

Kyle: It’s just so ridiculous. I think one of the things that tricks us into this is this endless supply of clickbait that says, “This will maximize your productivity and this will maximize your productivity, and if you’re going to be a writer, you will need your walls painted this color.”

Really, when you look at anybody … I have this book called Daily Rituals. It’s a couple hundred people that are these artists and just high achievers in many different creative areas. Everyone of them have different rituals and they were all developed over time as people found out their own personal needs.

Every writer will tell you that you don’t sit down and just know exactly what you’re going to say. You sit down and you try really hard to say something. It usually comes out terribly, then you have to go back and edit it. It’s very messy.

We were so hungry for answers. People feed us answers and then we paralyze ourselves when we can’t set up this perfect instance when in reality, it’s equivalent going to the gym and sweating, just sitting down writing garbage until something golden comes out.

Brett McKay: There’s also this big emphasis on goals. I’m a big fan of setting goals for myself, but how can goals get in the way of taking action?

Kyle: Before we get into that, I want to say that goals worked really well for a lot of people. I know a lot people who have a lot of successful goals. For me, they didn’t work as well and I think a lot of people get stuck with goals because they rely on a fantasy future and deny the present moment.

Everyday you go the gym and you’re still chubby, you’re failing, because your goal is to be ripped or to be X pounds, so everyday that you go, it’s not motivating to know that you’re behind schedule. Then, when you do hit that goal, when you do get ripped let’s say, you have to immediately set a new goal that you’re then failing at and start to achieve that one, so say maybe it’s bulking in the gym.

It’s always just your set up for disappointment and failure. A fix for this was actually suggested by the author of Dilbert comics, Scott Adams. He suggested setting up a system. You have this general aim to get ripped. Instead of saying “I’m going to have 4% body fat by the end of two months,” you say, “I’m going to go to the gym for one hour everyday, four days a week.”

You set up a system and every time you implement that system, you are succeeding. You spend the whole time that you’re on the right track winning, and like we were talking about action before, that then shocks you into appreciating the actions being taken instead of just the results, obsessing on this abstract outcomes of actions taken now.

Brett McKay: Process oriented as opposed to results oriented?

Kyle: Right.

Brett McKay: One thing you mentioned is that planning can get in the way of taking action. Shouldn’t it play some role in your business or in your personal life? What role does planning and deep reflection fit to this ideal of action?

Kyle: Brett, I’m glad you brought this up because that’s one thing that the article really didn’t deal with and that it’s difficult to talk about when you want to balance two ideas. The goal of the article was there’s 10 overlooked truths about taking action. The reason I wanted to really dig into helping us understand what action is so that we can put it into a more healthy context.

A lot of people mistook that as “I should always be taking action. Thinking is terrible. Planning ahead, terrible.” Obviously, that’s just not the case. There’s no one-size-fits-all. If you’re planning out a trip to Mars, if you’re Elon Musk’s team, planning out a trip to Mars, you need every detail exactly right because there’s going to be very little improvisation you can do from Earth to help that mission out. You know what I mean?

On the other end is we’re just talking about the gym, going to the gym. You don’t need any plan to get in a better shape than you are today. Yes, reading a fitness book might be helpful and creating a plan might help you stay consistent, but going today, doing that thing now is going to invigorate the plan that you do create and give you better context for it.

The business version of this is the lean start-up methodology. This is especially true of software companies, not companies with complex plight change and requires huge investment up front, but you basically create an MVP which is a minimum viable product, what is the smallest thing that we can create to test this assumption that we’re making about our business?

You plan minimally and then you take action, and then, that allows you to take advantage of both sides of the coin. You take all advantages of taking action like watching new opportunities emerge, watching unforeseen problems pop up without as large of an initial investment, but at the same time, you have this minimal plan that is driving you in the right direction.

Brett McKay: It depends on the context, right?

Kyle: Yes, and for all of us in our individual lives, it’s always less than you think. It’s always you need to read less books, then you think you need to read less blogs, and you think when you’re risking very little, you need very little planning.

Brett McKay: Got you. One reason a lot of people don’t take action, and you wrote about this, is uncertainty. They’re surrounded by uncertainty. They don’t want to make that investment in the business because they don’t know if it’ll be a success or who knows how the economy will change. With out ever-changing modern world, things are just speeding up because of technology, things are unstable and always changing. How should we manage our life and career in the phase of such uncertainty?

Kyle: I think one thing that is extremely helpful to do initially, and this just helps you emotionally deal with uncertainty, is to differentiate between the uncertainty that you feel versus the uncertainty that actually exists. You don’t have to feel uncertain about a situation just because that situation isn’t 100% likely to happen. Once you differentiate between those two things, it makes everything else a little bit easier.

Brett, I know you’re a fan of stoicism and the stoics recommend one really interesting tool for dealing with uncertainty and that is the triad of control. As you go through life, you can separate situations or events into three parts. They’re either in your control, out of your control, or partly in your control.

Something that’s in your control is the effort you put into something. Something that’s outside of your control would be, is the company you work for going to stay in business? A mix would be you getting the job or getting into that school, or having success with this business because you can put in everything and that tips the odds in your favor, but it may not absolutely get you there.

Once you’ve separated things out like that, you can then totally focus on and do your best to tie your emotions to things that are in your control, and that goes back to the systems. If you tie your emotional life to completing your system successfully that day, then, you’re more likely to have the grit that’s needed to get through possible failures and stuff like that.

Brett McKay: Besides the emotional resilience, I think that’s really important in the phase of uncertainty, but what do you do about it on an operational level or tactical level, I guess? What can you do to manage the uncertainty so you’re not on the bad end of it, so you can adapt?

Kyle: Absolutely, yeah. You wrote a great post on this, too, based on Taleb, the Beyond Sissy Resilience, I believe. There’s two big ways that you can expose yourself to the upside. That is you don’t know what’s going to happen, but you’re sending yourself up to take advantage of something crazy happening, because you know that in the future, there are going to be wild shift, especially now, that’s increasing with the increasing rate of technology like you mentioned.

The first way to do that is to increase your optionality. That means give yourself more options to select from so when the time comes, you can make the best most advantageous choice. Examples of this would be having savings in the bank. If a business opportunity comes or investment opportunity comes, and maybe you can jump on that. Going to parties that you might not want to go to just because you are then exposed to interesting people who might be able to affect your life in a positive way, learning new skills that could be useful in the future.

Also, just I really don’t like talking about perspectives, but shifting your perspective to be open to the opportunities that come up, that increases your optionalities like crazy, because if you’re just focused on what you believe to be worthwhile today, you’re going to be blind to what might be the next big thing, or this wave that you’re sitting on that you don’t even realize it. Shifting your perspective to noticing new options.

Another way that we can take advantage of this uncertainty instead of having it bared down on us is making small bets or making small experiments. An example of this is the MVP that we talked about. This is how startups take advantage of this uncertainly.

Investors, in general, they don’t know what startup is going to be the next Facebook, the next Google, and so they have to invest in many different businesses, and they like to see a business that does believe that they know what’s right, what the future looks like, but then, they also want to be able to see that a business can pivot.

If their business model is disproven, they should be able to create something new, create something that based on what they learned from their failure will then help them win. Then, in our everyday life, if you’re looking for a girlfriend, making small bets is talking to multiple girls at the same time.

For our blog at StartupBros, when we decide what kind of program that we want to put together next, the training program, we used blog posts to gauge the demand for that type of project. We make small bets to know what we should double down on.

Brett McKay: Going back to optionality, I think a lot of people, particularly young people, misinterpret it as keeping your options open. What ends up happening is that they don’t make a decision. They have always different choices and they don’t actually take one because they still want the options available for them at some time when something doesn’t pan out. They want to maximize their choice. How do you balance? How do you maintain optionality while still getting going in life, making decisions, and making progress?

Kyle: That’s a good question. I think that it’s appreciating that the world is not totally uncertain and so, it’s not like the goal of life isn’t optionality. It’s not just about having options open because the things that you decide on, that’s why there’s depth. Optionality is your width, but it’s important to have depth. I think that that kind of model might be helpful. That’s how I think about it, but it’s difficult to measure. I think necessity forces people into that depth.

You talk about young people. It’s young people that aren’t forced into having to create something now. Honestly, they’re trying to hack their way to this place of, like you said, not deciding, of not committing. Yeah, optionality is not commitment. I don’t know if that’s helpful, but that’s the best I got.

Brett McKay: Got you. Speaking of hacking, the most recent article you wrote for us was called Stop Hacking Your Life and it went after the whole hacking culture, and we’re not talking about computer hacking. We’re talking about life hacks. I feel that’s one of those things that’s eating itself and it’s slowly going away to a certain extent, but you make the case that there are two approaches to life hacking. What are they and how can one of them be detrimental to our development?

Kyle: I think you’re absolutely right about it eating itself up. I think there’s two kind of relationships or postures that we have towards hacking. You’re either hacking in order to achieve an aim or to get a certain outcome. That means when you go to look up the best way to tie a tie, you do that when you need to tie a tie. You have an awesome video on that, by the way.

Brett McKay: Thank you, sir.

Kyle: It focuses you things that you’re going to use now that are specific to your situation. You’re optimizing for a specific outcome. Then, the unhealthy posture is hacking for hacking’s sake, which is this perverse meta-hacking and it’s where hacking becomes the primary instead of the result that the hacking was supposed to get you.

An example of this is scrolling through life hacker, just collecting articles on things that you probably don’t do, you don’t need to do, but they just blast you with this clickbait of “Here’s the answer to this question that you didn’t know you had until just now. Here’s 100 ways that you’ve never used to live a happier, better life.” That ends up, just like you said, frustrating the user and then they realize that life actually doesn’t get better because the goal is optimization itself, and when you optimize for … I like to look at it as a multiplier.

When you optimize for something, it multiplies on that number, but when you optimize for no reason or for life in general which is impossible, you’re optimizing for zero, and that it totally frustrating and ineffective.

Brett McKay: Have you read any GK Chesterton?

Kyle: I’ve read one piece. I believe it was one of your man vocationals.

Brett McKay: Manvotionals, yeah. He’s this fierce critique of Nietzsche. His critiques are fascinating. Really, Chesterton, he’s a great writer, super funny. In one of his chapters in his book, Orthodoxy … he’s a Christian writer. In Orthodoxy, he goes all over the place, but in this one part, he talks about when cultures or organizations start focusing on efficiencies, it means they run out of big ideas.

Kyle: Yeah, that’s it. That’s really interesting.

Brett McKay: I think that’s what happens frequently with business. They just focus on optimizing. We got to optimize our website so we can get more subscribers. We’re going to increase our option rate by 0.4%. What’s your big idea? What else are you doing? At that point, you don’t really have one. You’re just trying to squeeze out as much as they can from this thing that they’ve already done. There’s nothing wrong with that, I guess, but at the same time, it distracts you from the bigger picture of trying to create something better and bigger than you had before.

Kyle: I think one illustration of what you just mentioned is demand media which was basically, it’s just media company created by a belief of the founders of Myspace, and it was all based on creating content based on big data. They just would measure what is trending at all today, yada, yada, yada, and then they create just very quickly, very crappily create some piece of content that maps on to something that some big data system suggested and it’s terrible. Nobody wants to read it because there’s no soul. There’s nothing there.

I believe in that wholeheartedly. It’s a tough balance because there’s information that you do want to use. You do want to make sure that you maximize conversions, but only to the point that you’re not giving up what’s truly valuable. Brett, I got to say one of the reason I love Art of Manliness so much is because you more than maybe anybody else in this “industry” has refused this kind of perverse incentives and kept data in its place.

Brett McKay: I appreciate that, and honestly, the reason I don’t really pay much attention because it bores me to tears.

Kyle: Right.

Brett McKay: Yeah. Hacking your life, how can it hurt you in the long run if that’s all that you’re focusing on in optimizing your life? It brings you short-term benefits for sure, but in the long run, are there detrimental effects?

Kyle: Yeah, and there are very insidious, I would say, because like you said, because you get benefits upfront and it feels like, “Oh, my God. I’m optimizing my life which means I’m optimizing literally everything I do.” This is obvious, it could never be a waste of time. It’s not only just a waste of time, it puts you in a bad posture towards life.

In the article I go through very quickly, but there’s six ways that it perverts your perspective. One that it assumes that effort is failure because hacking is always trying to find the easiest way out. It’s aim is at whatever means less effort. Then, it forces you into bad decisions because it overvalues hype and undervalues the old and effective.

Anybody who pays attention to fitness, I honestly don’t know how people still read new books that come out about nutrition because it seems like every six months, they negate what they said the time before, and 99% of us know very specific things that we could do to make ourselves more healthy, be it going an exercising or eating some more greens, or eating less ice cream, or stop smoking. It doesn’t matter how much organic stuff you eat if you’re still smoking cigarettes.

Charlie Munger, Warren Buffet’s partner in investing, has this idea. He says “Take a simple idea and take it seriously.” I think that would get us past a lot of hype. Another thing, it puts us in the posture of aimless optimization. Like I said, when you optimize for zero, you’re still left with zero. The hacking posture, it makes us constantly worried that we’re using too much time, so we have this anxiety about literally, if something takes an hour, we feel like it should have taken 20 minutes or something like it. If we knew just the right way to do it, we could’ve done it faster.

That’s what stops people from starting businesses, is they keep deluding themselves because people keep promising them ways, a painless way, turn the key systems started business. If there’s truly a turn key system, then they didn’t require any personal effort. That company would just be a manufacturer of that type of company. It also makes you dependent on perfect circumstances. You mentioned Stephen King. If you’re trying to hack your life, find the optimal environment to write in, you’ll never start writing.

Finally, it favors irrational rationality. Actually, you came off of this. You just wrote a great piece on Nietzsche and you mentioned this in that piece and I thought that was super interesting, that when he said “God is dead,” his true fear was that our sense of meaning was going to be destroyed because of this new obsession with science taking God’s place in a way, and it absolutely has.

Depression is more prevalent than ever because it’s just we think that everything falls into rationality, we think that everything is explained by a material world when it absolutely can’t be. The antidote to this is to dose yourself with rational irrationality. Joseph Campbell who’s famous for The Hero’s Journey, he even said that rational irrationality is essentially the key to becoming the modern hero. The modern hero is someone who can create meaning by caring for something more than it rationally or reasonably should be cared about.

I blew through those, but those are all ways that this hacking posture can really mess us up.

Brett McKay: That’s awesome, awesome stuff. There seems to be an underlying theme in all your writing and thinking. What do you think it is?

Kyle: You mentioned this. Maybe do some soul searching. Honestly, I’m probably the least qualified person to answer this question, but my best idea is I’m trying to continue the project of self-trust. We’re shocking ourselves into self-trust.

Brett McKay: Self-trust, I like that. You mentioned one of my favorite guys, Charlie Munger. He’s really big on this idea of developing mental models in order to thrive and take action and I love his idea because mental models are just different ways of looking at the world. It could be a legal model, an economics mental model. Biology can be a mental model. You can take these different things and approach them to any problem life and find insights, right?

Kyle: Uh-huh. Yeah, absolutely.

Brett McKay: Are there topics or areas of studies or disciplines that you think folks should focus on in order to build these mental models to help them be more effective managers, thrivers, in the uncertain?

Kyle: You mentioned a couple of them. I think the big standards that Munger mentions are physics, biology, psychology, engineering and history. Bill Gates and Mark Zuckerberg will tell you that programming is the essential model. I like to use philosophy a lot as well as biology and economics specifically, but I think … My recommendation to people is to respect your interest. If that underlying theme is self-trust, then I say, trust your interests to provide you with some of these powerful models at least to start.

You see athletes and even big sports fans that use sports metaphors to get them through life, to make management decisions like big gamers that I know. They gamify everything in their life and they make it so much easier and enjoyable just by imagining at some RPG or something. Even fiction books or movies that people relate to, I think these stories provide really great foundational mental models and just how to be in the world. That’s my advise, is self-trust.

Brett McKay: Last question. I’m always impressed whenever you submit articles to us because you’re always quoting the source and and thinkers like Seneca, Nietzsche, Munger, all sorts of people. It’s all over the place. Obviously, you’re well read. How do you read so much and how do you keep track of what you’ve read?

Kyle: I read a lot of books because I think everybody reads a lot, but I just prioritize books over social media feeds, clickbait, bad TV. I refuse to watch TV show unless it’s True Detective or Game of Thrones basically, and that opens up an amazing amount of time. Everybody reads so many books a year worth of words just in really bad clickbait. I only read what I’m interested in, so it makes it very easy trusting those interests and following them. It’s fun to pick up the book and it’s not something I have to use willpower to do. I think you asked about tracking, sorry?

Brett McKay: How did track of all that stuff?

Kyle: I really don’t. I highlight all the books. I have a type of highlighting system. Books that I really, really care about, I put into Evernote. I type up all my notes, but that’s very few. Generally, when I’m writing, I just remember the gist of some passage in a book and I have to go find the book and open pages. Just to sift through to try to find it, it’s a huge, huge waste of time.

Brett McKay: That’s how we do it around here, too.

Kyle: Really? That makes me feel a little bit better, because there are some people with such big systems.

Brett McKay: I’m completely inefficient, but whatever, I think that’s okay.

Kyle: The important ones pop up.

Brett McKay: Right, it allows it to stew with all the other stuff in your brain.

Kyle: Yes. I think that makes it even more organic, you get the best quotes at the best time.

Brett McKay: Kyle, this has been a fascinating discussion. Where can people learn more about your work?

Kyle: Sure,, and especially, if they’re interested in everything that we’ve been talking today, probably just googleing Art of Manliness Kyle will get them the three articles that we really dug into today.

Brett McKay: Fantastic. Kyle Eschenroeder, thank you so much for your time. It’s been a pleasure.

Kyle: Thanks, Brett.

Brett McKay: Okay, guys, that was Kyle Eschenroeder. He is the co-founder and co-owner of the company StartupBros where they train individuals how to start their own online business. For more information about his work, you can find that at

That wraps up another edition of The Art of Manliness podcast. For more manly tips and advice, make sure to check out the the Art of Manliness website at, and if you enjoy this podcast, I’d really appreciate it if you could give us a review on iTunes. Tell your friends about us. Thank you for all your support and until next time.

This is Brett McKay telling you to stay manly.

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