Interviews → Knowledge Project / Shane Parrish

Shane:

Shane:

Derek, so great to finally get to talk to you.

Derek:

Shane, I am a super fan and super psyched to be here. There are only three podcasts I subscribe to, Conversations with Tyler, Seth Godin’s Akimbo and yours.

Shane:

Oh, thank you. We’ve been trying to do this for so long and we’ve been like, “Oh, I’ll just wait until the next time I’m over, and then we’ll do it in person and it’ll be so much better.”

Derek:

Yeah, and I’ve been a paid member of Farnam Street forever, and I’ve just been reading your stuff forever. It’s great to finally have this conversation.

Shane:

I’m looking forward to it very much. Part of the research that I did for this, it’s fascinating, because I know of you, I read your stuff and then going a little deeper behind the scenes is always fun. I found this really interesting story. You worked as a librarian at Warner/Chappell Music and you quit, and that is like one of the most interesting stories I have ever seen with somebody quitting. Can you share that with me?

Derek:

Sure. It was my first real job. It was at Warner Brothers in Midtown Manhattan, the music publishing division. It was an office with about 14 employees, and I was 22 years old and I’d been working there for two years. Just the bottom entry level position, running the music library. I loved the job and I loved my colleagues, but after two years I was ready to quit so I could be a full time musician. I was earning enough on the side as a musician that I could quit. So I found someone to replace me. It was an old friend that I knew would be perfect for the job. I knew that she would do it really well. She had the right temperament. She was in the right stage of her life. I knew that she’d be psyched about it and really give it her all like I did. So I offered her the job and she said yes, and she moved to New York City to do it. She stayed at my place for a while. I trained her and I taught her everything.

After a week or two of that, that’s when I told my boss that I have to quit now, but here’s my replacement. She already knows everything, and she’s starting on Monday.

Shane:

That is just phenomenally mind blowing that somebody at that age, let alone any age, would sort of think to do that.

Derek:

But I didn’t know otherwise.

Shane:

This is sort of the interesting aspect to this for me, because you started CD Baby after that. I think most people are generally familiar with that story, but the first time somebody quit, you were like, “Okay, who’s your replacement.”

Derek:

I guess when I quit that job at Warner Brothers, my manager just kind of went, “Oh, okay.” I basically said I quit and I walked out because everything was all taken care of. So yes, 12 years later I had my own company. I was running CD Baby, and the first time one of my employees came up to me and said, “Hey man, I’m going to have to quit.” I said, “Oh wow. Okay, no problem. Who’s your replacement?” Then he looked at me kind of confused. He said, “Dude, I think that’s your job.” Then I was confused. I was like, “Wait, but you’re the one quitting. Why is that my job now?” We were both confused.

Shane:

There’s definitely some benefits to being naive about the ways of the world. Can you share some of those with me?

Derek:

First principles thinking, baby, you know it well. I honestly didn’t even know it was called that until reading your site. In fact, I still don’t know that much about it, but I was really excited to buy your new books last night to learn more about it. To me, the world feels unnecessarily ceremonial, like people imitate others without questioning it enough, but I don’t want to learn their ways. I don’t want to be like them. Instead, I just ignore it all and ask myself, what’s the real point? Meaning like, what am I really trying to do here? What’s the real point of all of this song and dance? If it turns out that traditional complexity was actually needed, well, then I’d rather find that out for myself. Notice that this approach is more creative, right?

It’s more inventing instead of imitating, which then means it’s more fun. Let’s pick a concrete example of software.

Say I want a website to share my thoughts, so I look at WordPress. That’s what everybody else does. Let’s just look at WordPress. I go to wordpress.org and I download the zip file and I look inside and it’s like, what the hell? There are 884 PHP files in here. There’s 602 JavaScript files in here, 19 database tables. What the hell? No way I’m going to learn all of that. I just want to put five paragraphs of text on a webpage. Okay, so what’s another option. Everybody seems to like medium.com. Let me look at medium.com. I pull up an article, I’m like, what the hell? It was like 2.5 mgbs of downloads, like 33 JavaScript and CSS files, just to display an article? No way. That’s like a thousand times bigger than it needs to be. To me, if I were to tell all of my readers, go to medium.com to read these five paragraphs of text I wrote. That would be like those companies, if you order something small like a USB stick, and they mail it to you in a big box full of styrofoam. It’s like, no, no, that’s junk. You’re giving me your garbage. It’s like dumping my garbage on everyone.

So I’ll ask, what’s the real point here? I just want to post an article on a webpage. I’ll just open up a blank document. I’ll just type out the article and I’ll put paragraph tags around it. I’ll put the title in an H1 header tag, and I’ll just put a couple little HTML headers and footers, so it’s a valid document, and then put it on a server and okay. I need a homepage to list the articles, so we’ll add some ULI list tags to the homepage, a HREF to the article and I’m done. Now I have two HTML files, no PHP, no JavaScript, no database, and the file size is like less than 1% of the typical medium.com or WordPress blog post. Talk about complexity, in the case of WordPress, I understand that their complexity came from making generic software that pleases everyone from Disney to CBS. There are companies with hundreds of employees needing to use WordPress all at the same time to manage their content, but I’m just me and I don’t need that complexity. I think that this is a nice metaphor for life. It doesn’t have to be so complex. You can do just what’s best for you, not need to adopt the legacy software that everyone else uses.

Shane:

That’s really interesting. Two themes stuck out to me there, the complexity theme, but also the imitation versus innovation. If you don’t imitate, one of the byproducts of that, that I can see is you’re going slower. It probably took you longer to do that than it would have to download WordPress, and that goes back maybe to the complexity, where they’re intertwined in the sense of maybe we don’t have to do as much as we think we have to do.

Derek:

Right. Rich Hickey is the inventor of the programming language called Clojure and he has a brilliant talk that’s up on YouTube. I think if you search like “simple versus easy,” Rich Hickey. He makes this beautiful comparison about how anybody can go to their computer and type, “Gem install hairball.” You can type one command and install WordPress on your server. He said, yes, that was easy, but you just installed a big steaming pile of garbage on your server that is massively complex, because he defines complex as having the word root in the word “complect,” which means to braid two things together. He says complexity is when you’ve got many things braided together. He said, it was easy and fast for you to type a gem install hairball or install WordPress, but look what you’ve just done. You’ve now just installed thousands of complex files when it would be a little harder for you to just make your own HTML page from scratch. But notice that by definition, that’s simpler, so simple is not always easy.

Shane:

I like that a lot. I’m just trying to figure out like in my head where to go with that. I think of Farnam Street, we’re always trying to reduce. I’m trying to reduce the size that people download. I’m trying to take away the things that people don’t need and just leave what’s left, but that is not easy at all. That’s hard.

Derek:

Yeah, you have to nerd out on it. I really nerd out on this stuff. In fact, this, my little rant that I just gave you about WordPress, for example, I said this to a friend of mine. When I was done, she said, “Yeah, but so what?” I said something like, “Do you know that the average user’s going to download like 98 files just to read your four paragraphs of text. It’s so unnecessary.” She goes, “So what, most people aren’t looking-”

Shane:

Not many people think about that.

Derek:

Yeah, she goes “almost nobody but you is actually looking at the code.” For most people, they just click a link on their phone and they read the article. They don’t care that behind the scenes, 98 files were downloading. I’m like, “Oh yeah, I forget. I nerd out on this.”

Shane:

But you do, and that’s what’s important though. It’s something that you care about. You care about other people’s experience with your stuff, which is really rare these days. I was thinking yesterday, as I was preparing for this, I was trying to order some wine for some friends of mine and it was online. It was just so difficult and I was trying to support local businesses and I was trying to do something nice for my friends. It’s like 90 minutes later, and I’m still trying to order this wine, and it’s like, copy-paste the order number into your e-transfer that you send to this address with this password. Holy cow, have you used the product that you are getting other people to use?

Derek:

Innovation versus imitation, for most things, I just find innovation more fun, and we’re humans, fun matters. If I get more joy out of doing it this way and it takes me six hours, but it’s fun. Versus, I could just click this link and be done with it in 10 seconds, but it’s less fun. I’m sorry, now I’m back to the making a website, not ordering wine. I wouldn’t find it fun to order wine for 90 minutes, but if you find the process fun. Some people make their own furniture. You can visit somebody’s house, and it’s like, I made that table. I made that chair. Of course, they could have gone to Ikea to buy one, but they chose to make it because they wanted to. I take that approach to a lot of things in life.

Shane:

Well, one of the other things I’ve noticed with imitating is that we often don’t know what’s next. You consider hiring somebody with a skill, but a skill that they’ve just sort of copied from somebody else. Then when things change or they’re different, they have no idea how to respond or how to deal with that.

Derek:

Right. Well, isn’t that your interest in the first principles thinking? It’s get to the root of what you know. You have this Fineman quote opening volume one of your book, right?

Shane:

Yeah. We’re the easiest people to fool. That much is clear, but I also think that we try to, not consciously, but we do try to fool other people. Maybe Warren Buffet’s a good example, the 2008 housing crisis hits, and there’s a whole bunch of people who imitate Warren Buffet. They talk like him. They go to McDonald’s every morning and they eat their Egg McMuffin and they say all the right things. Being able to distinguish between Warren Buffet and these people, if you couldn’t see them, it would be really hard. Then a crisis hits and they’re paralyzed. They’re not Buffet, and it’s only through that crisis that it’s revealed. This whole thing in life is also like, how do you tell the difference between somebody who’s imitating and somebody who’s the real deal, who actually understands?

Derek:

That’s a great question. That’s great.

Shane:

I was hoping you would have an answer.

Derek:

Nope, let’s just leave that as a beautiful rhetorical question for the audience.

Shane:

How do you decide what to work on? You have a unique framework. You’re known for this “hell yes” or “hell no” sort of framework. How did you come about that? Expand on that for me.

Derek:

Hell yeah or no, to be clear, this is just one tool in the toolbox. I don’t have that much to say about my monkey wrench. It’s not meant to rule the world. It’s just a monkey wrench, but here’s the problem. We tend to say yes to whatever we can. We like to stay busy. When faced with a decision to do something we ask, can I do that? And if yes, then we often say yes. Maybe it’s the fear of missing out. Maybe it’s optimism. Maybe it’s because time is like distance, where we can’t see far away so clearly, so we mistakenly think that we’ll have more free time in the future, but then today comes and now it’s all close and vivid.

Now you can see it clearly and ah, you’re too busy. You curse your past self for saying yes to that thing that you have to do today. Three months ago, it was easy for you to say yes to this thing in the future when you have infinite time. The solution is to raise the bar all the way to the top, say no to almost everything and leave space in your life, leave free time. But this is not relaxing. It’s strategic, because then when something great comes along, something that makes you say, “Oh, hell yeah, that would be awesome.” Then not only can you say yes to that, but now you have the time and energy to throw yourself into it completely. Now you can give it your all. You know the baseball metaphor, you can knock it out of the park? I think strategically it’s better to do five big things with your life instead of 500 half-assed things.

Shane:

I think that applies to a lot of things. It’s better to be thoughtful and tweet less than just throw ideas out there. How did you come up with this?

Derek:

Yeah, I’ll tell you, but I’m sorry, I have to say one thing, what you just said, like it’s better to tweet less instead of more. I still just say that it’s just different. Some people do get their best creative ideas by just spewing out as much as possible. Maybe they spew out a thousand times more than most people, but if 1% of those ideas are better than it’s the net better result. I don’t want to say like, this is the best approach to take for all things. That’s why I say it’s just one little monkey wrench. I think it’s a tool to use when you’re overwhelmed and almost drowning in opportunities, and therefore, you don’t have the time to give your full attention to any of them.

As for how it came about, it was just a situation where I was telling my musician friend, Amber Rubarth, about a decision I was trying to make about whether to go to this conference or not. As I was explaining my thought process behind the decision, just thinking out loud, Amber Rubarth is actually the one that said, “Basically, you’re not trying to decide between yes and no, you’re deciding between fuck yeah and no.” I just laughed and I loved it, and so I blogged about it the next day. I changed the word to hell to soften it a bit and the idea caught on and that’s all.

Shane:

When you started implementing that, was it a gradual process or what was the feedback from people?

Derek:

It was instant. Sometimes it takes somebody else to say things that you might have already been feeling or thinking, but then somebody puts it into better words. We love when poets do that. We love when books do that, when you read a little wise book, an old one, like Think and Grow Rich or something. You go, “yeah, yeah, there we go.” I already felt this, but she just put it so well, that’s the way I feel. My friend, Amber Rubarth, who’s a songwriter, just gave me that nicer, simpler mantra. If it’s not a hell yes then say no. I just started using that for everything instantly. But to be fair, I was at a time in my life where that made sense. I had just sold my company a year before and everybody was throwing everything my way and everybody wanted everything from me. It was a good time to raise the bar all the way. But strategically, there are other times in your career when really the most strategic thing to do is to say yes to everything, because it can be like lottery tickets. If you got nothing going on and somebody’s offering you an infinite amount of lottery tickets for free, well then, how many do you want? I’ll take all of them please. I don’t think that hell yes or no is something that should be applied to everything in life. You have to know when you’re drowning in opportunity or starving for opportunity.

Shane:

Is that the only criteria by which you would sort of like gauge when to use this, is like your opportunity cost?

Derek:

I think so. Off the top of my head, yeah.

Shane:

When you’re running a CD Baby, you had to learn to delegate, and you hinted in your book that we’ve run into this, like small businesses run into the ceiling. I think my friend Brent calls it the ceiling of brute force, which is you get caught in this trap of not delegating, doing everything yourself. Can you expand on that, and how did you learn this?

Derek:

First, we’ll define it. Every solo freelancer or person doing anything knows this feeling where you’re so busy, you’re doing everything yourself, and you know you need help, but to find and to train someone would take more time than you have. Instead, you just keep working harder and harder and harder until you break. How I learned it, I broke. I hit that breaking point. I did exactly that, and then I broke. My company was three years old and I had eight employees, but I was still doing everything else myself. I was just working 7:00 AM to midnight, seven days a week, and a lot of things in the company still went through me, meaning like every five minutes, one of my employees would have some kind of question for me, “What do we do about this? What do you do about that?”

It was getting hard to get anything else done. I felt like I would just show up to work and just answer my employees questions all day long, and I hated it. I hit my breaking point. I really like deep work and I really love focusing. For work to turn into this constant state of every five minute interruption just made it unbearable. I stopped going to the office. I started shutting off my phone until I realized that I was running from my problems instead of solving them. I realized this was a do or die moment, like I need to fix this or I’m toast.

I just had a long night of writing and thinking and reflecting on this. I just realized I need to make myself unnecessary to the running of my company. I need to do this. This is now super important. I’m at the breaking point. The next day I was like a changed man. I walked into work. As soon as I walked in the door, as usual, somebody asked me a question, “Oh, Derek you’re here. Hey, what do we do about this?” But this time, instead of answering their question, I called everyone together for a minute. I was like, “Ben, over here, Tracy come. All right everybody, Nicky just asked me what to do when a customer asks this. I’m going to tell all of you my answer, but more importantly, I need to tell you the thought process behind it. Here’s what I think we should do and here’s why. My rule of thumb is, if this then that. The big philosophy here is this. I want to make sure that everybody’s happy and dah, dah, dah. I’ll explain my philosophy.”

Then I asked around to make sure that they weren’t just pretending to listen, and I made sure that everybody got it. Then I asked Melaina over here to start writing this in a manual.

I said, “Can you start a manual today? Let’s make this like the company manual,” and wrote down the answer to this one situation and the philosophy behind it, and then everyone got to back to work. Of course, five minutes later, it happens again. Somebody asks me another question. Once again, I gathered everybody around and we repeated the process. I just kept doing that until every last thing that was my job, even like, I think I was still doing the accounting or the putting stuff into QuickBooks or whatever myself, even that. I said, “This is the last thing that is still mine. Amber, I’m handing this off to you. This is yours now.” That was it, and suddenly I was completely not necessary.

I started working entirely from home, and there was a funny moment where I’d call into the office after not being there for a week, somebody would pick up the phone and say, “CD Baby.” I’m like, “Hey Dan, it’s Derek.” He’s like, “Oh, hey man.” I’m like, “How’s everything going?” He was like, “Good.” “You need anything?” He’s like, “No, we’re all set.”

Shane:

“Why are you calling?”

Derek:

I was like, “Okay, well, I’m just home if you need any help with anything.” He’s like, “We’re all set, man, thanks though.” And that was it, I was unnecessary. At the time my girlfriend had just moved down to LA to go to film school, so I was like, all right, I’m going to come join you. I moved down to LA, which I thought was like a nice symbolic show that it’s like, all right guys, I’m no longer here. This is up to you. Then what was most interesting about this is that once it was done, like once I was really not necessary, I still was working these 12 hour days because I enjoyed it. But now I was only working on the improvements and the innovations, like the new stuff. To me, this was the fun stuff. This wasn’t work, this is fun. This is creating. While I was away in California. My company grew from 1 million to 20 million in four years. It grew from eight employees to 85 employees while I was away, just basically without me.

To me, that was the lesson. The huge difference between being self employed and being a business owner. It was actually from the book, Rich Dad, Poor Dad by Robert Kiyosaki, that I learned this idea.

You know you’re a true business owner when you could leave your business for a year and come back a year later and find that it’s doing better than when you left. That’s when you’re no longer self- employed, you’re a business owner.

Lastly, for anybody interested in this subject, if you think this is really speaking to you and this is something you need, the best book on this subject is called E-Myth Revisited by Michael Gerber. It says it way better than I could. I didn’t discover that book until after, like years after I’d gone through the process, but when I read it, I was like, yeah, there we go. This is the masterpiece on this subject.

Shane:

Somebody putting into words what you feel, right?

Derek:

Exactly.

Shane:

That’s a really interesting philosophy. I like the idea that you moved from self-employed to a business owner when you can walk away. Did you have any sort of feelings of I’m not needed in a bad way?

Derek:

I think only that one week that I described calling the office and being almost like a little sad that they didn’t need me for anything, but it was a fleeting moment, and then it was just joy after that. Then it would blow people’s mind that I’d be down in LA and meeting up with somebody. Especially somebody else who was still in that trap. They’re like, “Oh my God, I can’t handle everything. I’m so swamped.” They’re like, “Dude, how do you do it? You’re sitting here at lunch with me. You’ve got a whole company going on up in Portland.” I had to tell them this tale. It was hard work, but I delegated everything, and it just, I had to. I was really at that breaking point where I was ready to walk away if I didn’t.

Shane:

You’re such a thoughtful person. I’m curious as to what you’ve learned about delegating that most of us would find surprising.

Derek:

You have to have a long-term perspective. You have to know that it’s like, all right, this is going to be hard. Or, yeah, it’s going to be harder at first for the long-term gain. Right? Like, if you realize that you’re at this breaking point, your time is already full. You’re already not sleeping enough. You’re already working too much.

Now, you’ve decided that you need to hire and train somebody. Well, yeah. Sorry. It’s going to get even harder before it gets better. You’re going to have to sleep even less until you’ve found and trained somebody to do it. But then, you keep your eye on the horizon instead of the obstacles. Look at the distance instead of today and know that it’s going to pay off.

Shane:

How do you think about the pairing between ideas and execution?

Derek:

Oh, you know I’ve got something to say about this, don’t you?

Shane:

I do. I hope so.

Derek:

All right. All right. Actually, that was a funny storytelling segue, because this came from living in Los Angeles where the people I was around in L.A. were all speaking in future tense. It was always about what they were going to do, the deals that are going to happen, everything. So, yeah. We’re in talks with this guy at EMI and we’re going to be working on this thing. The pilot for this show, it looks like Fox is going to be picking up this pilot. Everything was always future tense. At first, I was smiling and oh, wow. That’s great. But after a while I realized like, oh man, everybody is speaking in future tense about these things that are going to happen and they never do. So, what was all that hot air about? I felt like wearing a tee shirt that says, tell me when it happens. Like, why are we talking about this?

So, it was during that time that a good friend of mine asked me to do a favor for him to hear out his friend’s business idea. People tell me lots of business ideas, but this one was kind of a bit of a breaking point because this guy insisted on making me sign an NDA to hear his business idea. Like ordinarily I would have just said, no, I’m not going to sign an NDA to hear an idea. But it’s because of this situation where it’s like a good friend of mine asked me if I could please, as a favor to him. I was like, all right. All right. Here’s your NDA. Then, I drove across town, sitting at a restaurant and finally, okay, nice to meet you. “What’s this big idea you want to tell me?” And he said, “okay. You ready?” I said, “yeah. I’m ready.” And he goes, “it’s online dating with music.” And I said, mm-hmm. And he goes, “dude, online, dating with music.” I said, yeah. “Is there more to this idea? “And he goes, dude, “that’s the idea, man. Online dating with music.”

I was like, “wait, do you have like any implementation,” again, it’s like he’s telling me something profound. He’s like, “dude, no. Online dating with music.” Then, he said, “so here’s what I’m thinking, dude. My friend, our mutual friend tells me that you know how to program. So, I’m figuring that you can make this thing, you do the programming to make this thing happen. I’m the idea guy. Like you and I can go 50/50 on this, man. This thing is going to be huge, man. Online dating with music. I’m the idea guy. You’re the execution guy.” Or he said, you’re the programmer. I was like, what? No, no, no, no, no. So, I said, “all right, look, how do I explain this?”

It actually took me till later that night to think of how to think of a nice metaphor that was easy to explain. What I wrote is that I think of ideas as a multiplier of execution. Right? So, let’s pretend that we have two columns of numbers here. So, an awful idea, let’s say that’s a negative one, but a weak idea is a one. An okay idea is a ten and the great idea is a 20. Okay? Now, imagine another column over here. That’s the execution column. No execution, doing nothing about it, let’s say that’s a dollar. Weak execution $1,000. Okay execution, $100,000 dollars. And great execution, let’s say $1,000,000. But the real point is that, to make a business, you need to multiply those two columns. That the most amazing idea with no execution is just, okay. Let’s take a great idea, worth 20, no execution, one dollar. That great idea was worth 20 bucks if you don’t do anything about it. But, on the other hand, you could have like an okay idea and okay execution and maybe make a million dollars. But, if you have a great idea times great execution, then you can make 20 million dollars, or more. So, that’s just my rule of thumb way to explain this. Why I’m not really interested in hearing people’s ideas. It’s just not interesting without the execution.

Shane:

I think that’s a brilliant insight. I had another way of coming at this exact same philosophy with different words, but it was adding too much value. So, we used to work in boardrooms and people would pitch ideas for projects, sort of like Shark Tank. I mean, a lot of organizations have these like gates where the people who can allocate resources decide which projects to fund. One of the things that I noticed was that the people making the decisions were always trying to make the ideas just a little bit better.

So, somebody would come to you with like a 95% idea. And you would be like, oh my God, have you thought of this? This is going to move this from 95 to 95.5 and I am a genius.

Derek:

Right.

Shane:

And what I noticed was that the willingness of the person to own the idea, to be motivated, to execute went down. So, the quality of the idea almost inarguably went up a little bit. How much is sort of like irrelevant. But the ability, the desire of the person on the other end to own the idea, to execute it went down. It always went down by so much that the expected outcome from the project is always, almost always worse off.

Derek:

I love that you brought this up. I think this is a very underrated insight. Did you read I think it was Marshall Goldsmith’s book called-

Shane:

Yeah. I think that’s where I actually sort of got the words around it. What got you here won’t get you there.

Derek:

Yes. What got you here won’t get you there. Yeah. I think the way he put it there, in America the slang term is you say, here’s my two cents on that idea. So, it wouldn’t make sense if you don’t have that currency, no matter where you’re listening. The American slang is, here’s my two cents. So, Marshall Goldsmith in what got you here, won’t get you there said, yeah, don’t add your two cents. And he gives a very vivid description of somebody coming to you with an idea. And he said, even if you have an idea for how it could be better, just zip your lips, smile. Say, sounds great. Go for it.

Shane:

Which is weird that it took me so long to hit on this myself. Right? Because I mean, I was on the other end of that and so annoyed with these people. Can’t you see how willing I am to own this and run with it and I want to execute on this. You’re telling me, do this one little... change the color of my button from blue to red. I’m like, that just lowers my desire to sort of lead this project.

Then, when I got on the other seat, I was like, oh. Now I can add my value. Right? And then, it took me a while. I stopped doing it and I found this really amazing thing. Like everything got better. People worked harder. They were more motivated. They owned things instead of just being somebody who executes what they’re told. I mean, they actually own the project as much as you can own a project in an organization. Everything was so much better. Even if I had ideas that were like, oh, here’s a roadblock, I would let them go as far as they could, right before they had to execute on that part and then have a conversation with them. Nine times out of ten, they figured it out. So, I never even had to say anything because they figured it out because they were in the weeds doing the work.

Derek:

I love that about books. That it’s like, yeah, you and I both experienced this, I mean, everybody. Probably everybody listening to this goes, yeah, I’ve had this situation too. Like my boss told me to make this one change. It’s like, I’ll do it with a grumble and let’s them do it. I love when the authors of these books that just take the extra time to think something through deeper, and take the extra time to put it into good words, and take the extra time to edit it down to a way that makes it spread, makes it easy to remember and communicate. It’s just such a valuable thing. I love it.

Shane:

Speaking and reading, books changed your life at an early age. You read Awaken the Giant. How did that change things for you?

Derek:

Ah, yeah. Tony Robbins, Awaken the Giant Within. God. It’s like asking someone what they learned from their religion. The stuff that Tony Robbins preached in that book is like so deeply ingrained in me that it just feels like reality.

Shane:

I’m embarrassed because I’ve never actually read it.

Derek:

Well, it’s funny. Tim Ferriss and I met for the first time in 2007. He told me what book made the biggest influence in his life and I told him what book made the biggest difference in my life. The next day we both went out and read each other’s favorite and both of us were like, no.

That does nothing for me. So, comparing notes later, we realized that we both read this formative book for ourselves when we were teenagers. So, I think it’s more about timing. Like I don’t know if Awaken the Giant Within is actually a great book, but I read it at a very, very formative time when I was like 18 or 19 and just super ambitious and ready to take on the world. Not only that, but someone who I cared about very much and was gorgeous, gave me this book and said, you need to read this. So, of course, I read it with like a maximum, what do you call it? Suggestibility.

Let me try to think. The things in my philosophy or like how that book changed my life, the philosophies that I got from that. I think the important ones are, you can change the way you feel about anything in an instant. So, if your emotions aren’t working in your favor, you can just change them. Related to that, events are neutral. You can interpret events as good or bad. You can interpret a neutral event as crisis or as opportunity. He makes this great example of New Orleans funerals, saying like, even if you think of something that we think of just as objectively sad, like somebody you care about has died, well, look at how they do funerals in New Orleans. They play the sad music as they’re marching down the street with the coffin. At a certain point, the drummer comes in and it turns into a celebration as they dance and celebrate this person’s life. He said, that’s the perfect example of how you can change your emotions in an instant and you can feel about an event however you want to. You can celebrate somebody’s death with joy.

The big idea then is you can choose whatever interpretation works for you. Whichever one you feel like taking on is the one you can. Your emotions are completely under your control. He gives specific techniques on how to do that. He talks about asking yourself better questions and how the questions you ask yourself change everything. Like, when something goes wrong, you can ask yourself, what’s great about this? And again, he gives this colorful example of some horrible thing that happened in his life, like a manager of his ran off with millions of dollars of his company, like embezzled. He said, okay, I’m going to follow my own lesson. What’s great about this. And he said, nothing. Nothing is great about this. This is horrible. He said, okay. Keep asking, keep asking, until he found something. He found a perspective on this neutral event that now empowered him instead of disempowered him.

He talks about what you focus on, changes everything. And again, the colorful story here, I can’t believe I’m like remembering all this. God, how old am now? I’m 50. I read this book when I was like 18, 32 years ago. I’m remembering all these vivid stories. Right?

So, he talks about going to a party. Just imagine yourself going to any random party full of a bunch of people. You take a bunch of photos at that party of people. Later you decide to show just the happy photos to somebody. They would get the impression that that was a really fun, happy party. But you could also take just the photos that you caught candidly where someone was looking sad, or alienated, or lost and show somebody only those photos. And now, it looks like a really sad, depressing party. It was actually the exact same party, but you’ve just chosen a different filter. Of course, metaphorically, we all do that in life. Like you could just look at a newspaper today and you can choose to get outraged by it. Or you could choose to get depressed about it. You could choose to get excited about it.

Shane:

It’s almost like a thermos, right? Like it reinforces whatever you bring into it.

Derek:

Yes, Shane. It’s exactly like a thermos.

Shane:

No. But, I mean, like your lens.

Derek:

It’s so good.

Shane:

If you put something hot in, it’s going to stay hot. And, if you put something cold in, and it’s going to stay cold.

Derek:

Yeah. I’m imagining some kind of like sci-fi thermos where you could twist something and it would instantly turn from hot to cold. Anyway, let’s do one more. So, I think I got my idea of long-term focus from him. The big idea is like, there’s no such thing as failure until you give up. Because, until that point, you’re still just getting feedback. You could have just tried a hundred things. The old classic example of Edison with the light bulb filament, you’re just getting feedback. Like, okay. That didn’t work. What else? He talks about how people overestimate what they can do in one year, but underestimate what they can do in ten years.

Focus on where you want to go. Don’t focus on what you fear. He had a little story about how he learned race car driving. And he was like suddenly getting terrified. He found himself looking at the wall like, oh, no. I’m going to hit that wall. And he said, my trainer literally grabbed my head and turned my head towards the road where I wanted it to be going. And he said, that’s a great metaphor. Look where you want to go, not at what you fear. God. Yes. Sorry. I guess I have a lot of these. These are so ingrained in me. Like they all just feel like, well, yeah, duh. That’s life. That’s reality. But the truth is, I got all of these things from that book.

Shane:

That’s so powerful. What makes for good writing for you? Have you read it again, actually, since then?

Derek:

So, I think I read it when I was 18, and like again when I was 20, and again when I was 22, and maybe one more time when I was like 25. But that was like a paper book, which then I’ve given away. And so, I think just like a year ago I tried getting it on Kindle. And I looked through it again and it was like somebody telling you that water is wet and the sky is blue.

Shane:

Right. Of course.

Derek:

It’s like, okay. This stuff is just too ingrained in me. Sorry. I can’t read it again. It’s all just obvious now.

Shane:

How do you filter what you read now?

Derek:

It’s usually either to solve a current problem in my life. Like say, if I’m having issues with parenting, or having issues with keeping up with my habits, or even like a knowledge problem like I don’t know who those old philosophers are. People keep talking about Nietzsche. I don’t know anything about Nietzsche. So, I’ll let go read a book to solve that problem. I often read just because I think that this book’s insights could help my life right now, even if it’s not a concrete problem. But like whenever I read anything by Mark Manson or Steven Pressfield, I always come away feeling like, yeah, that’s a really cool insight. Like it wasn’t to solve a concrete problem. I like their philosophies.

Often it’s just for curiosity. Like I just, two days ago finished a big, long course on linguistics and that was a blast. John McWhorter, The History of Language. It was fascinating. I love reading about geography. I love reading about the culture of different countries. I just read a book a few months ago about the culture of Finland and just found it fascinating.

How do I filter though? Knowing that what I’m looking for is what I just described, then how do I choose exactly what book? I think I probably rely too much on Amazon reviews or just if there’s a wise person that I’m a fan of them and they say that this book is a great book, then I’ll go read that book.

Shane:

Do you read it cover to cover? Like, when you pick up a book, are you searching for something that you wanted to learn? Like what’s your process for picking up a book and then reading it?

Derek:

Yeah. I don’t skim. I know a lot of people skim. But, whenever it’s like reading time, I try to slow down my internal clock. Focus on just this. This is a different pace than being online, and clicking, and surfing, and clicking. I try to read just start to finish, unless a book really sucks. Unless it’s like I’m a third of the way through, I’m like, yeah, I don’t like any of this. Then I’ll trash it. But, for the most part, I hear them out. I go start to finish. And, most importantly, which we can really nerd out on if you want, is I underline every surprising or interesting idea that I want to think more about later. So then, when I’m done, I take all of those underlined, ideas and I put them into a text file. I usually just kind of put them into my own words. I remove their unnecessary words. I think I’m more of a harsh editor than most people. I chop every unnecessary word.

So, now I have the core of this idea in eight words. Then, in that text file, I separate each idea with two line breaks. So, the idea is on one line or maybe two or three lines, but whatever it is, I hit enter twice to leave two line breaks before the next idea so that later I can write a little ruby programming script to parse them when needed. Later I reflect on these ideas. That’s why I saved them. I’m never trying to summarize the book. I actually don’t care about the book. I just want the interesting ideas inside so that I can reflect on them later and ideally add more to them myself.

Shane:

Talk to me about the reflecting on them later part. I mean, a lot of us highlight a whole bunch of things in a book. We’re like, oh, that was amazing. This is great. And then, we’re onto the next book. We never sort of like go back and think about, or digest, or do the mental work of sort of like making those ideas our own.

Derek:

Right. Okay. So, I have a new approach to this. So, I used to just take this one big text file with all my notes from one book and I would just keep those text files on my phone. If I was just sitting on the bus to get somewhere, I would just look at my folder of text files and I would just open one up and just kind of reread it and just kind of stop and look out the window and think about something interesting. But then, I found that, again, I don’t really care about the book. I like the ideas inside. So, here’s a project that I’ve been working on for a long time. I’ve just been dabbling with this for a long time. I’m tagging every single one of those ideas from every book I’ve read since 2007. I’m tagging them with keywords and loading them into a database.

So now, if I’m thinking on a subject like commitment, or regret, or hedonism, or memory, or pain, then I can just search for my notes around that subject. I can pull up like 173 ideas that came from 28 different books instantly, but just browse these ideas. Because again, I don’t care what books they came from anymore. I just want the ideas. So, I’ve separated them from the book and I’m keeping them as their own little atoms to play with. The main thing I do now is to pull up all my notes on a subject like this, like say hedonism. Then, with all of these notes in front of me, I open up my own text document to start from scratch with my own thoughts on this. So now, it’s almost like I’m in a room of some really smart people talking around this subject. It’s inspiring really interesting thoughts of my own that are often like a reaction. It’s like I’m joining the conversation of these thinkers. I want to see what I can add.

That’s honestly what my next book called, How to Live, the book that I’m writing right now, this is kind of what the book ended up being. It’s grown out of this process of surrounding myself with a bunch of thoughts around one subject, and then writing my own thoughts around that subject as kind of a reaction to the others around me.

Metaphorically, it almost feels like if I was a painter and I was allowed to bring a blank canvas into a great museum and I could sit in a room of my favorite paintings ever and paint my own, which is not imitating theirs, but it’s influenced by. I’m kind of building on that, inspired by that. Does that make sense?

Shane:

I think so. I mean, the geeking out part of me is like, okay. So, you have this private database and you tag things so that you can easily search it. And, when you’re thinking on a topic, you look at it. And, through that regular digestion and hitting on those things, you make them your own. And then, you write about them.

Derek:

Yes. So, it’s about internalizing it, not memorizing it. So, I’m into anki and flashcards, and spaced repetition. So, I used to think, I wonder if I should somehow feed all of these ideas from all of these books into spaced repetition so I can memorize them. Something never felt quite right about that. That took me a while to realize what it was is that, no, I don’t want to memorize these people’s thoughts. I just want them to lift up and inspire my own thoughts, which I really need to internalize these things. To me, that only comes from reflection and giving it time. So, yes. Like you said at the beginning when you asked that, I often would read a book, go, wow, that was really good. Then, onto the next book. Yet, as time went on, I thought, wow. I’m not remembering these books unless I really stop to reflect. I feel like the reflection time is when you really learn. The moment when you read somebody else’s idea, that’s a wow moment, but you don’t really learn it until you’ve put aside the time to reflect on it.

Shane:

And is that where you come up with your directives?

Derek:

Oh, the directives. The directives, I think, came from... sorry. Everybody listening, Shane is talking about something that I’ve blogged about a few times, which is this idea of taking an idea and turning it into a directive, which is telling you to do an action. If you go to my site, if you go to sive.rs, or if you read anything I’ve written, or even the TED talks I’ve put out into the world, or whatever, you might notice that I like being very succinct. Maybe not in conversation with Shane right now. But, when I put something out into writing, I like being very, very, very succinct.

I like chopping out every possible word, leaving only the words that need to be there. So, I noticed that, as I was learning about certain things, I felt like most books use way too many words. I came to this idea that probably the most succinct way to communicate an idea is to focus on the action itself. Like, if you command the action, then the action, like a seed, I think there’s like a nature metaphor in here somewhere, that the action has the seed of the idea in it and that the action carries the idea along with it. You can talk for 400 pages about calories, and this kind of fat versus that kind of fat, and protein versus that. But instead, you could just tell somebody, eat this, don’t eat that. Those actions would carry that 200 pages of information in the actions. Therefore, the succinct directives, the actions, please my minimalist, ruthless editor sensibilities more.

Shane:

I want to talk about directives a little bit more. What’s interesting to me when I think about directives is they’re great if you can get them from other people, but they’re different, again, going back to this imitation versus like knowing and understanding. So, you’re coming up with these directives. Like you’re doing the work, the mental work. Like you have an experience. You’re reflecting on it. That experience can be yours, or it can be from reading a book, or somebody else’s story. But you’re doing the mental work of reflecting, integrating, digesting, and then you’re coming up with these directives. So much of life today is, “Just give me the directive,” and we haven’t done the work.

Derek:

In spaced repetition, like Anki as far as flashcards, a lot of people say, “Yeah, just give me somebody’s deck so I can learn JavaScript or whatever.” I’m like, “No, no, no.” The whole point of flashcards and memorization is after you’ve learned this thing, you make the flashcard to help your future self remember it. The flashcard is not the moment of learning.

I feel the same way about the directives. Although, there are different subjects in life where I want to know more about this or not. So actually the example that I gave about this fat versus that fat and these calories versus those calories, I don’t care about that subject so much. So I would not want to read a 400 page book about nutrition and diet. That’s an example where I just want somebody to tell me what to do, tell me eat this, don’t eat that. That’s all.

I don’t need the details. So because I feel that way about nutrition, I can imagine somebody else feeling that way about, say, technology or stoicism or language learning, or whatever it may be. No, I don’t want to talk around this subject for 300 pages. Can you tell me what to do in one page, and then I’ll just do that? I think this comes down to trust. If you trust the source, then you don’t need all of the supporting evidence.

Shane:

I would add one caveat to that, which is I think and the environment’s not changing rapidly, right? So the source came up with these in a certain environment and you just have to make sure that that environment still exists, because if it changes rapidly, then the source is likely to be right but right at the time or right for that particular environment, and then you won’t know what happened.

Derek:

Why would you be thinking of that in April 2020 Shane?

Shane:

Let’s do a deep dive on directives. Why don’t you give me some of your categories and go through some? I don’t want to put you on the spot. But-

Derek:

Oh, sure. I don’t mind.

Shane:

How to be Antifragile or thriving in an unknowable world.

Derek:

This is like you’re a talk show host and you say, “Hey, why don’t you perform one of your songs for us?” “Sure, I’ll be glad to do that.” No, really, I don’t mind. All right, hold on. We all like the Antifragile concept.

Shane:

It’s particularly apt right now too.

Derek:

Exactly. How to thrive in an unknowable future. Again, to give context, this is where I’ve read a bunch of books on this subject. I took a bunch of these book notes, lots of paragraphs, and condensed them down into these. What is it? Six directives. One, prepare for the worst. Since you have no idea what the future may bring, be open to the best and the worst. But the best case scenario doesn’t need your preparation or your attention.

So mentally and financially prepare for the worst case instead. Like insurance, don’t obsess on it. Just prepare, then carry on appreciating the good times.

How to thrive in an unknowable future, number two, expect disaster. Every biography of a successful person has that line, “And then things took a turn for the worse.” So fully expect that disaster to come to you at any time. Completely assume it’s going to happen and make your plans accordingly. Not just money, but health, family, freedom, expect all of it to disappear. Besides, you appreciate things more when you know that this may be your last time seeing them.

Three, own as little as possible. Depend on even less, the less you own, the less you’re affected by disaster. Four, and this is straight out of Antifragile, choose opportunity, not loyalty. Have no loyalty to location, corporation or your past public statements. Be an absolute opportunist doing whatever’s best for the future in the current situation, unbound by the past. Have loyalty for only your most important human relationships.

Number five, choose the plan with the most options. I got that one from Kevin Kelly. The best plan is the one that lets you change your plans. For example, renting a house is buying the option to move at any time without losing money in a changing market.

Number six, avoid planning. For maximum options, don’t plan at all. Since you have no idea how the situation or your mood may change in the future, wait until the last possible moment to make each decision. Funny thing is I posted that in 2016 on my site and I just, last month in March 2020, in the middle of quarantine and all that, went back and read it just smiling and nodding like, “Yeah. Prepare for the worst, expect disaster. Yeah.”

Shane:

Dude, this is like gold. I just want to sit here and listen to you keep going on this stuff.

Derek:

We’ve got to do the Munger. You and I are both... Hey, actually Shane, have you heard of Charlie Munger? And I think you would like him.

Shane:

Vaguely. I mean I think I remember coming across him in a headline somewhere.

Derek:

So you and I are both Munger fans. So I’ll just do this one more that is totally not a rip off, but Charlie Munger’s idea. I think it was in Poor Charlie’s Almanack, one of his speeches to one of the schools where he did the reversing it. How to stop-

Shane:

Prescriptions for misery. Guaranteed prescriptions for misery.

Derek:

How did you just happen to know that? Guaranteed, yeah. Thank you. That was it and I loved that format. So yeah, I tried my own version of that which was how to stop being rich and happy. Number one, prioritize lifestyle design. You’ve made it, so it’s all about you now. Make your dreams come true. Shape your surroundings to please your every desire. Make your immediate gratification the most important thing.

How to stop being rich and happy, number two, chase that comparison moment. This is from the book Stumbling on Happiness. You have the old thing, you want the new thing. Yes, do it. Be happy for a week. Ignore the fact that the happiness only comes from the moment of comparison between the old and new. Once you’ve had your new thing for a week and it becomes the new norm, just go seek happiness from another new thing.

Number three, buy, not rent. Why rent a house, a castle, a boat, or a car when you can buy? It’s not about the thing, it’s about identity. This shows who you are now.

Number four, internalize your new status. You worked hard to get here. Celebrate, relax, admit that you’re in a different class of people now with different needs. Understand there is no going back.

Number five, how to stop being rich and happy, be a connoisseur. Learn what others say is the finest. Insist on only the finest. You will now be unhappy with anything but the finest.

Number six, get to know your possessions. Now that you own the best, it’s time to focus on what you’ve got. Learn all about the features of your new possessions. Spend more time getting your surround sound and your heated floor just right. Work out the whole solar panel charging of your Tesla car. This is important. And lastly, number seven, how to stop being rich and happy, acclimate to comfort. Eliminate every discomfort from your life.

Blame others when the world seems hard and is not living up to your standards.

Shane:

That’s so beautiful and so true.

Derek:

I really like this format of making things as succinct and as actionable as possible. So I really need to turn all of these into a book. I have just a rough draft of a book called Do This that would just be a book full of these directives.

Shane:

I love that idea. I hope you do that. I think the world needs that.

Derek:

I hope people email me and tell me to do that and keep annoying me until I do it.

Shane:

I will. You know what I’ll do is, because I can program, I’ll just create a script to email you every five minutes. I’m curious how you go about making important decisions.

Derek:

Well I don’t aim for reality and I’m actually really interested to read your book. Like I said, I just started reading your new Volume 1 last night, but the first thing I underlined in it was the thing about blind spots. It was right there in the first few pages and you said about blind spots. And I think, “Okay.” This is actually a new idea to me because I’m not used to aiming for reality. In fact, I used to have a record label called Artificial Records and my slogan was quote, “Why settle for reality?” I think the Tony Robbins stuff I said earlier was a bigger influence on me than searching for reality, because you heard maybe the common thread in there is it’s about looking for a perspective that helps me, right?

I don’t remember what book I got this from, but credit to this goes to some book out there that says... It gives this idea that imagine that you need to walk across an elevated plank, but you’re too scared so you’re not doing it. So does it help you to think that the plank is lying on the ground? Right? If it was just lying in your backyard, you’d walk across that plank no problem. You wouldn’t fall off of it, you wouldn’t be scared of falling off of it because why would you fall off of the plank? There, you walk across it. What’s the big deal? So does imagining that elevated plank just lying in the grass in your yard help you? Yes or no?

Does it help you to believe that there’s a safety net below you? Yes or no? Does that make you walk across it? Does it help you to picture that on the other side of that plank is a burning building and your child is inside, and also there’s a hungry tiger behind you chasing you and it’s going to kill you in three seconds if you don’t walk across that plank? Now does that get you to walk across the plank? Okay, well then that’s the winning perspective. Whatever makes you take the necessary actions is the perspective that helps you. I’m never aiming for reality. I’m trying to make decisions usually based on finding the perspective that helps me take actions. I’m not even aiming for results or effectiveness. The real answer is I think I’m usually making life decisions because they’re fun. Granted, I’m not an investor. I’m not making investment decisions, right? Usually, I choose things more based on the compass of fun and adventure, right? Having a different perspective can make something more of an adventure. If you think of the stereotype, the old classic stereotype of the explorer with the pith hat, right? Going off into darkest Peru to places that no one has explored. Well, I like doing that with perspectives. I often think of any random thing and I think what approach could be fun or could be exciting or could be new and uncharted, then that’s creative, right? I don’t even care very much if this fails because my only goal was to just try it out. Let’s see what happens if I take this approach.

I think sometimes, just like you asked me about Awaken The Giant Within, and I have to try hard to imagine what of me came from that book. I think it’s actually the same thing with music. We haven’t really talked about music itself, but I think I’m so damn influenced by the fact that I was a full time musician for 15 formative years. From the age of 14 until 29, all I wanted from life was to be a successful musician. So I think now I still approach life like I approached music, with lots of, “Let’s see what happens if I do this, let’s see what happens if I run my voice through this guitar pedal. Let’s see what happens if I use this flute like a drum.” I think that music thinkers were probably my first favorite thinkers, like Brian Eno for example, or John Cage. Here, I have at all times, handy, some of my favorite Brian Eno quotes. I love these quotes so much, not just Brian Eno’s, but from a collection of musicians whose ideas inspire me. I ended up making a little website called musicthoughts.com, where I put all of these inspiring quotes about music. Here are four from Brian Eno, just to give a concrete example. “Art doesn’t end at the edge of the canvas.

It’s position in the world both physically and culturally can completely change the meaning of the art.” Okay? That’s one idea. “Instead of writing songs, let’s make a hypothetical film and then make a sound track for that film.” That’s an idea. Here’s a favorite one, “Cut a vital connection. Find what’s holding everything together then eliminate that.” And last one, “When you listen to Miles Davis, how much of what you hear is music and how much is the context like all the things you know about Miles Davis?”

So when you’re listening to music, you’re actually, quote unquote, “Hearing all the stuff around it too.” Okay. So I’ve got a thousand of these on this website called musicthoughts.com, and I think I forget that I’m still taking this experimental musical approach to life. So when you ask how I make decisions, I think it’s very similar to Brian Eno making musical decisions in the recording studio. Like, “ Hmm, this approach sounds fun. Hmm, let’s try this.”

Shane:

I like that a lot. I want to go back to something you said at the beginning of this which was whatever compels you to take action. But how do you decide what actions to take in a situation?

Derek:

I don’t know. I think that’s just one of those, every situation is different. Sometimes, you have a concrete goal, right? “I need to exercise more. What philosophy, what mindset-”

Shane:

What’s going to help me do that, yeah.

Derek:

Right. But other times, you just don’t really know what to do. All right, I’m going to give a concrete example from my life. This is personal. But after I sold CD Baby, I felt really lost and lethargic for a year or two. I didn’t know what to do with myself. I felt like I had peaked and I dabbled in this and dabbled in that and thought, “Maybe I’ll do this, maybe I’ll do that.” But then there was one moment on one airplane where I was just reading something. What it was doesn’t matter because it was just a random story about Benjamin Disraeli or something, but there was a sentence in there that made me go, “Oh my God, I know what I want to do.” It was just talking about how Benjamin Disraeli never shied away from the spotlight that he courted attention and took on the extra responsibilities of courting attention.

That tiny idea to me, it just set off a bunch of other things in my head like, “Oh my God, I’ve been running from responsibility, because I didn’t like having 85 employees at CD Baby and so I’ve been wanting to avoid all responsibility for the rest of my life. But by doing that, I’m turning invisible. I was considering legally changing my name, but oh my God, if I step into the spotlight more instead of less and just take on that little bit of responsibility, that extra responsibility, then oh my God, I know what I want to do now. I don’t want to be this ex-music store guy. I want to be a writer, speaker, thinker kind of guy. I want the TED conference to invite me to speak and I want people to want to hear my thoughts on things, to buy books of my thoughts.” At the time, I was just a guy running a music store and this was a totally new idea. But Shane, it was like the first thing in a year and a half that made me bolt up out of my seat and instantly I was like, “Oh my God. Yes, I know exactly what I want to do.” And it turned into action. When the plane landed, I just bolted into action and made things happen for the first time in a year and a half. So I didn’t know what was the right action to take and I didn’t even try to ask myself, “Is this the right action to take?” I think you can tell when something feels like the right action to take.

Shane:

That’s really interesting, because when you said that, what I internalized a little bit was it’s not the tactic, it’s the direction. So you knew where you wanted to go, not necessarily how to get there. I mean you’ve lived it.

Derek:

No, I didn’t. No, sorry. But until that moment, my plan was to legally change my name and disappear into Europe and be an open-source programmer.

Shane:

Yeah, yeah. But then you changed. You wanted to be this thinker, you wanted to do this. So you came up with this direction that you wanted to get to and then it was a matter of establishing those tactics.

Derek:

Oh yeah. And then making a plan relatively is the easy part. Once you know where you’re going, once you pick a place on the map and say, “I want to go there,” it’s like, “ All right. That’s North East of here, let’s head North East.” Of course, you’re going to adjust along the way to continue to use our explorer with the pith hat metaphor.

Shane:

I don’t know if a lot of people think that way. I think a lot of people are just like, “What’s best for me in this particular moment,” without necessarily a direction.

Derek:

I’m no expert at this. But to me, that would sound like that’s how I felt in my year and a half of muddling around.

Shane:

Right. Oh, I think we all feel that way at various points in our life, right? Switching gears a little bit. What’s the biggest mistake you’ve ever made? And how did you recover from that?

Derek:

Did I? The only one that I can say really objectively, “Yeah, that was a big, huge mistake,” was carelessly wrecking what could have been a great romantic relationship. So, yeah. Sorry Rae. But let’s talk about my second biggest mistake, because that was financial so it feels like it would fit in better here.

Shane:

I want to dive into this relationship one if you’re okay talking about it. What happened? If you’re not, we’ll just skip it over.

Derek:

I mean I don’t mind. I’ve never talked about it publicly, but yeah. I’m going to change her name and call her Rae. She was amazing and wonderful and we were totally in love. Then in some split second weird moment, when we were hanging out in Singapore, I got some bug or something in my head that bothered me about something she said, and I just kept it to myself instead of bringing it up. Then while she was asleep that night, I called a friend of mine to say, “Yeah, what should I do?” And my friend was like, “Just run. Run the other way. This is clearly not working, just get out of there. Just tell her sorry and get on the next plane out.” And I went, “Yeah, I guess you’re right.” Speaking of different perspectives on any given thing, my friend gave me that perspective in that moment. And so when Rae woke up in the morning, I said, “Sorry, I’m going to get out of here on a plane today. We’re done.” And she was devastated and I coldly left.

So a couple epilogues to this that actually make the story is that a couple of months later, that same friend that gave me advice on what to do in that moment was doing some reading about relationships and going to see a counselor and learning some stuff and said, “Hey, guess what I found out?

I’m what they call love avoidant and they tell me what that means.” And I was like, “Oh my God, I have those tendencies too.” And I thought, “Man, I really called the wrong person that night.” I was in a suggestible influenceable state of mind that if a different friend would have told me, “Dude, go back in there, that you love her and she loves you. Do not let this go. Relationships have times that you need to work through, do not get on that plane. Stay with her,” I would have said, “Yeah, you’re right.” But instead, I randomly called the other friend. In fact, I actually tried to call three or four different friends and the one that I talked to was just the one that happened to answer the phone.

Shane:

Just by chance, yeah.

Derek:

Just by chance. So I destroyed a great relationship and another epilogue is that sometimes when that happens, you never talk to the person ever again and you never get to apologize, you never find out what they were thinking. But in this case, I did talk to Rae again many times. I think a whole year later, I told her the full story of what happened that night, how it was just that one thing she said on the subway that bothered me, but I kept it to myself and I didn’t talk with her about it because I didn’t know how and she said the sweetest possible thing. She said, “You know what? You and I were always so good at talking on the phone,” because we’re doing this over the phone, and she said, “I wish you would have just gone to the next hotel room or called me from the lobby, and we could have talked about it over the phone.” I went, “Oh God, that is such a beautiful thing to say.” Then when I told her the whole story of what happened, she said, “Yeah, I’ll admit I don’t think I’ve ever cried so hard in my life.” She said, “I’ve never been that in love ever in my life. I’ve never been so hurt in my life. That was really devastating.” But then we continued to talk about it and the funny thing is, she’s probably my best friend today. We talk all the time, but relationship wise, it’s too late. It killed that thing. So yeah, that’s probably my single biggest mistake. Wow, I just told that story to Shane on the podcast. Hello world.

Shane:

What does love avoidant mean?

Derek:

I don’t know exactly. Here, let me Google that for you. I don’t know. I haven’t dove into that.

I think it taught me to take these things more seriously and to not be lighthearted. There’s a beautiful line in the movie Before Sunset with Ethan Hawke and Julie Delpy, I believe that’s the third one. They made three of them. So the first one was Before Sunrise, when they were in their twenties, then they made Before Midnight I believe, in their thirties, and then 10 years later, they made Before Sunset I think. I think that’s the correct order of the titles but it was in the third one, which I generally didn’t like that movie because they were all like now they’re married and they’re just fighting for the whole movie, and I didn’t really like seeing that. There was one killer line where they’re reflecting back on when they met 20 years earlier, and what they did in that first movie 20 years earlier is they just decided to trust the universe and they didn’t even trade phone numbers or last names. They just said, “I’ll meet you back here in a year at this spot.” And she said, “Okay, see you here in a year.” And then they departed. So now 20 years later in the third movie, they’re going, “God, why did we do that? What were we thinking? Why not just trade phone numbers?” And one of them said, “I know why we did that is because when you’re in your twenties, you think that these amazing loves will just come all the time.” You think, oh, that was a really sweet meeting. But if this one doesn’t work out, I’m sure there are plenty of others.” He said, “Then you get to your forties and you realize they don’t. Those are really, really rare.”

So I think that’s why I still objectively, when you ask what’s your biggest mistake, the first thing that comes to mind is me messing up that relationship. That was me not taking it seriously enough. I think it’s so impressive that as I continue to know her now, she’s still the most amazing person I know and I messed it up. What’s funny is after that all happened, and I told some friends about my deep regret, different friends than the love avoidant friend, all of my friends do the thing that friends do to each other is they say like, “Oh dude, it’s all right. I’m sure it’s for the best. I’m sure something inside you probably knew that this wouldn’t have worked out anyway.” I was like, “No! Hold on.” We should not sugar coat everything, because we really learn best from pain. Pain teaches us like nothing else. I think I need to feel the pain of this mistake and not write it off. It’s like, “Oh, it’s for the better anyway.” No, it’s not. I need to feel that pain, so that the next time something like that comes into my life that I don’t make the same mistake.

Shane:

Yeah, man, you definitely messed that one up. Is it hard being friends with her now?

Derek:

No, she’s amazing. She’s the most forgiving. Her heart is ginormous. It’s amazing. No. We’re awesome.

Shane:

That’s awesome. What’s your compass?

Derek:

It’s situational. It’s not steady. Sorry. That’s not the admirable answer, but I think maybe because I’m exploring so much. I like that metaphor today. I’ve never used that. “The pith hat in the darkest Peru.” Isn’t that what they say in the Paddington book, the jungles of deepest Peru? Anyway, explorers don’t go in a straight line very much. We’re exploring. I often focus on an aspect of my life that’s lacking, and then I’ll enhance it until maybe it’s almost overflowing. Then I turn my attention to whatever aspect is now lacking after that. I think it’s really interesting that we all have conflicting needs simultaneously. At the same time, we have a need for stability and a need for adventure. That we have a need for the comfort of the known, and for the excitement of the unknown. We have those needs at the same time. I imagine that the “perfect” person would plot a path perfectly between those two needs. But more likely, and in my case, I tend to be a bit of a pendulum swinging back and forth. Yeah, I think my compass is not steady. It’s situational.

Shane:

I think that’s really interesting that you said “plot this perfect path between them.” I think that would be a less interesting life.

Derek:

Maybe. Well, some people like this approach to life. James Clear wrote this masterpiece of a book called Atomic Habits. If you take that book all the way to heart, I could imagine someone taking of their important values and making sure that they address them all every day or every week. “I need a little bit of time for adventure. I need a little bit of time for what’s known. I need a little bit of learning, a little bit of creating and a little bit of family time.” That is amazing and admirable, and I’m sure there’s some people that would thrive. I mean, I would probably thrive if I lived like that. But I guess we all have a nature. A way that comes, I was going to say comes easiest to us but maybe our nature amplifies certain ways.

We can do things that are against our nature. But if we do things that are in line with our nature, then those things are really supercharged, right? Because that’s just our nature. Cheetahs can also swim, but a dolphin does it better.

I just don’t find myself to be that kind of person that can do one thing for an hour, and something else for two hours, and then this for an hour, and this for 30 minutes. I throw myself completely into whatever I’m doing almost to a fault. I love just doing one thing all the way. And I’ll do that for hours, or days, or weeks, or months, or sometimes like in the case of CD Baby, I did one thing for 10 years. Then at a certain point, I think, “Okay, I’m done. Now, I’ll do something else.” But I obsess.

Shane:

That’s beautiful. I love that bit. I wanted to make a point before we went back to habits, which was sort of like working with the world versus working against the world. Right? The way that you sort of mentioned that made me think of that. I’m going to look up a quote by Joseph Tussman. It’s so indicative of this. He says, “What the pupil must learn, if he learns anything at all, is that the world will do most of the work for you, provided you cooperate with it by identifying how it really works and aligning with those realities. If we do not let the world teach us, it teaches us a lesson.”

Derek:

Holy crap. That’s good.

Shane:

I think that’s just a beautiful and sort of like what you were hitting at. I think that’s just another way of looking at it. Where we can fight our reality, but it takes a lot of work and effort. Or we can align with who we are, and our realities, or how the world works. It takes a lot less work and effort. And when we do that, we’re amplified. You can think of it as tail wins versus head wins.

Derek:

Nice one. Yeah. Thanks for pulling up that quote and bringing up that subject, because I think I spend a lot of time feeling a little bad about my nature. I loved the book Atomic Habits.

Shane:

James is a phenomenal writer.

Derek:

Yeah. But then I look at my actions, and I just dive completely into one thing at a time, and then I feel like I should be more like the Atomic Habits role model and I’m not. That’s a really nice way that you put it with head wins and tail wins, and nature, and just calling it the world instead of calling it your nature. This is your reality. We’re all experiencing our own reality and in my reality, diving into one thing at a time is the way that the world rewards me.

Shane:

I think that word “should” is really interesting. Right? You said, “I should be this way,” so you’re feeling some sort of guilt about not being the way that you feel you should be. But do you actually want to be that way? I mean, there’s so many ways to dive into that.

Derek:

I’ll do one more Tony Robbins quote. He calls that “shooting all over it.” Look, I love changing my mind. I love having my mind changed. I love changing. When I’m reading Atomic Habits, for example, I’m sitting there going, “Yeah. This is the way to live. Right on! Yes.” In that moment, yes, I want to be like that. There have been many ways, obviously. Look, we’re all walking instead of crawling. We’ve all changed in our lives, and so there are some ways that you might have said when you were 16, “Hey, this is just the way I am. I’m always going to be this way.” But then at 36, you are very different than you were at 16 and no, it turned out not to be true. I’d like to think that that can keep happening. Even at the age of 36, you could say, “This is just my nature. This is how I am.” But then at 56 you can be very different. You could have taken on some new skills. Maybe it was gradual, but you can be a very different person than you used to be. We can all construct who we are, I think.

Shane:

Speaking of who we are, do you have foundational values?

Derek:

Those probably change based on situation. A few months ago, again here we are in April 2020. A few months ago, I would’ve said that travel and cultural exploration was one of the most important things to me. This is why I moved to Europe. I’m living in England right now. I moved here so that I could travel my ass off. I have a list of 50 places in Europe that I’ve read about, learned about, know about, but never been to. I want to go to all these places.

I want to learn the culture in each of these places. If you would’ve asked me a few months ago, “Derek, what are your foundational values?” I would’ve said, “Well, Shane. Number one, cultural exploration. Travel.” And here we are in a quarantine, which I was sad about for a minute. Then I had to just question that. Is that the only way I’m going to learn about other cultures is to get on a plane, and go there, and walk around? Or is that a bit of a red herring? How much did I really learn about Turkey from walking around Istanbul. Wouldn’t I have learned more about Turkey by reading three books about Turkey, maybe watching the top five most popular movies in Turkey, and maybe scheduling phone conversations with 20 people from Turkey? That’s the same number of hours invested, but I think I would learn more about the culture in that way. So, hey, I can do that from anywhere. All right. My values have just changed. Travel is no longer my most important value, which means that I guess it was like friends of convenience. Like those friends in high school that you were friends with because they lived next door, but you weren’t really that good friends. As soon as you moved away, you never talked again. I guess you weren’t that good of friends. I guess travel wasn’t really that much of a foundational value for me, was it? If I was ready to let it go in a minute. So, if I ask myself what doesn’t change?

Shane:

Yeah. What’s invariant?

Derek:

Invariant. Oh, good one. I love changing my mind. I love understanding a different point of view. I love creating useful things, whether that’s books, or articles, or software companies, or who knows what in the future. I think those are my big three. I love changing my mind, understanding a different point of view, and creating useful things. If I look back decades, those are always there. Those don’t change. And you know what’s really nice that I actually just thought about yesterday morning when I woke up? This was one of those 5:30 AM, before I feel like getting out of bed thoughts. All of the things I love that mean the most to me in life don’t take any money.

Shane:

Oh, that’s interesting.

Derek:

I often ask myself what I would do differently if you were to suddenly give me a hundred million dollars or a billion dollars.

Just open up my journal. In fact, I have a recurring journal on this subject. I call them topic journals or thoughts on, where I come back to certain subjects repeatedly. I just give them their own diary on that subject.

This one is called Richard.txt. What would I do if I had a hundred million dollars? I often do that as some kind of brainstorming thought experiment. Over, and over again, every time I try I’m always stumped. I actually try really hard. I ask really hard. I really try. But every time, the answer is basically nothing. If you were to give me a hundred million dollars, I’d just give it right away because I just won’t use it for anything. I just don’t want it. All the things that I love the most in life, just learning, thinking, and creating. It doesn’t take any money. In fact, money is probably a distraction that would take me away from those things if I suddenly had to attend events or whatever. Wearing a tuxedo to attend this event now that I’ve been given the Nobel Prize. I don’t want to Nobel Prize because it would take me away from these things. You know what I mean? Put in whatever example you want there, but that was a nice thing to realize in bed yesterday morning.

Shane:

It goes back to the Notorious BIG, man. More money, more problems.

Derek:

Exactly. I thought that was Warren Buffet that said that.

Shane:

He doesn’t strike me as a guy with a lot of problems.

Derek:

That’s true.

Shane:

How did you become a minimalist? Where does that come from? Were you always that way?

Derek:

No, it’s because I moved house a few times. I think like I said earlier with my woe is me story of the relationship, I think you learn best by feeling the pain. You can preach minimalism to people, but then they can still go buy that desirable thing. I think it’s only when you felt the pain from having too much stuff that you finally get it. Right? I used to have too much stuff, and I moved house like three or four times. And every single time, I’d load up the big U-Haul van full of my stuff, and then get to the new place and unload the stuff. The first time it was annoying. The second time it was really annoying.

The third time I was like, “Oh my God.” Every time I unpacked this stuff, what is it for? Why do I have all this stuff? Then it was an accident of fate that I moved to Portland, Oregon while CD Baby was in full swing. It was just taking off when I moved from the little village of Woodstock, New York out to Portland, Oregon. Because I was just so damn busy with work, I put all of my stuff into storage temporarily,meaning it to be like for a few weeks until I could find a home. But then I ended up living at my grandma’s house.

Shane:

And you realized you didn’t need all this stuff.

Derek:

The stuff stayed in storage for six years, until finally six years later as a present to my employees, I’m like, “Okay, everybody. Help yourself to my stuff. Everybody can have one thing.” Somebody took my guitar. Somebody took my speakers. Somebody took my mixing boards. Somebody took this and that. Yeah, I just gave away everything I owned. The last thing that I had that nobody wanted to take, of course, were my diaries. I used to have like 20 or 30 big notebooks that were my diaries ever since I was a teenager. I looked at them when I was like, “I’m really going to lug these around for the rest of my life?” I was like, “Nah, just throw them in the dumpster.”

Shane:

If your house was burning, what would you grab?

Derek:

My kid. That was easy.

Shane:

What non-living thing?

Derek:

Are turtles living? Yes.

Shane:

I knew you were going to say your kid, but then I was like, “Oh, I just phrased that wrong.”

Derek:

Actually, yeah. I have a real answer. I have all of my passports and yes, it’s plural, in a little Ziploc bag for that specific purpose.

Shane:

You’re either a spy, or-

Derek:

Well, that’s just different subject. I left America 10 years on my explorer mission, you know? I have five different driver’s licenses from five different countries, and I have like four different resident ID cards, and a few different passports from different countries. I keep them all in one folder. Actually, I’ve put them into one safe place for that purpose. My one thing that’s irreplaceable. And I keep a little USB backup of my hard drive in there. I’ve had this happen where my computer just completely dies. I’m like, “All right.” I just take this little USB stick, I stick it into any new computer, and I’m good to go in 30 minutes. Those things are in one grab bag. Everything else can be bought and replaced. Those things would be really hard.

Shane:

How old is your son now?

Derek:

Eight.

Shane:

That’s a great age, man. That is such a fun time.

Derek:

Yeah. Oh, they’ve all been fun times. It’s funny. I did that to somebody once. When my kid was four, I talked to a dad whose kid was eight, and I said something about like, “Oh, I can’t wait until he’s that age.” And he said, “You know what, man? We always say that. The time you’re at, it’s always the best time.”

Shane:

I’ve noticed that the people that are around me that are the unhappiest parents have almost something universally in common, which is you can tell when they first have a child that they’re going to be an unhappy parent because they’re always hoping for the next phase. This is my heuristic for identifying people who are sort of unhappy parents, but haven’t admitted it to themselves. When their child’s in diapers, it’s like, “I can’t wait until they’re out of diapers.” Then when they’re out of diapers, it’s like, “I can’t wait until they go to school. My life will be so much easier.” And you’re never in the moment with them. You’re always just like, “I can’t wait until the next phase.”

Derek:

Wow.

Shane:

But they tend to be like that across the board. Right?

Derek:

Right.

Shane:

Like, “If only my spouse or partner was like this, then I would be happier. If only work recognized my value.” It’s really interesting. I don’t know how accurate it is, but anecdotally it seems to hold.

Derek:

Yeah. To me, the person I knew that was most like that didn’t have a kid, but she was in a perpetual state of, “I’m going through a hard time right now.” At first, I thought I just happened to meet her when she was going through a really hard time. But I knew her for years, and years, and years, and years, and years, and no. She is always going through a hard time right now. It’s just a way of seeing the world, it seems.

Shane:

Yeah. I mean, there’s a great quote. I forget who said it, but it’s like, “People show you who they are. Let them.” Which is interesting, because we often meet people going through a hard time. We write this off, right? Like somebody is like, “Oh, I just can’t wait till they’re out of diapers.” Oh, they’re having a bad day. But then it gets reinforced over and over again. You’ve mentally just sort of like walked away from it. What’s the most common mistake you see people repeat over and over?

Derek:

The most common? Drinking alcohol. Sorry. That’s not profound.

Shane:

Do you drink? No. Do you drink?

Derek:

A little bit. I mean, every few months I’ll have a drink. Yeah. Sorry. That’s not profound. I just tried to quickly think what’s the most common. You didn’t ask me, “What’s the most important to addressing humanity,” but that’s the most common.

Shane:

No, just common. Like, drinking or abusing? Walk me through that a little bit more. A lot of people are on that gray area between them. I think the mentality that says hey, anytime you get together with friends, of course. You need alcohol.

Derek:

“Hey, I’m having friends over. Get the wine.” I think that blurs kind of quickly into like, “Well, we’re having friends over. We need wine.” Which at that point becomes something other than close to addiction. But I don’t know. Sorry. I don’t have profound thoughts on this. That was just off the top of my head.

Shane:

No, that’s really interesting. I have a friend who, just to add to this for a second. Because he showed me something, or he put things in a way that made me see things in a new light. He said, “I was in that gray area for a long time.” And he’s like, “I realized I was hanging out with people I didn’t want to hang out with just to consume a few beers or a few glasses of wine.”

Derek:

Wow. Yeah. I’m almost unreasonably averse to anything that looks like addiction. Even recently, I used to always keep mints in the car. When I was driving I would have a mint. Then one time I noticed. I was like, “Oh my God, I’m out of mints. Oh my God, hold on. I need to find a gas station to go get some mints, because I have no mints.” I was like, “Whoa. Hold on. What was that? Why do I think I need mints?” I was like, “Okay, no more mints for me.” Just even little tiny examples like that, I’m wary of. The thing is with people who drink, I don’t think of things as mistakes much. Your real question was: what’s a common mistake? I don’t know if I could call drinking alcohol a mistake. In fact, I actually really appreciate it when people think and act differently than me. Right? If I think that it’s wrong, that makes it even more interesting because now I want to understand their strange perspective. It’s more interesting when somebody thinks differently from me. I tried living in San Francisco for a little while. I had to leave after a few months. I hated it, because everybody thinks like me. I’m happier living in a place like Singapore where most people don’t think like me. I’m like, “Ah, there we go. This is much more interesting.” I want to know more about people that are not like me. They’re more interesting to me.

Shane:

All right. Final question, but it’s a big one. I mean, it’s a big gnarly one. Goes as in detail as you want to.

Derek:

Now I don’t know if you’re being sarcastic or not.

Shane:

No, not at all. What does it mean to live a meaningful life?

Derek:

I don’t think life has meaning. I don’t think anything has inherent meaning. I think it’s all just a blank slate that we can project whatever meaning we want onto. Like my example of walking the plank before and sorry if anybody wants to remind me what book that came from. You try on different meanings, and none of them are correct. They’re all just different ways of thinking of something. Then if one of them makes you take better actions, well, then congratulations. It’s nice to remember that meaning is not a fact. It’s just a belief that you’re wielding for now. It’s just a perspective that you’re choosing. When people ask about the meaning of life as if it’s a geode you’re going to crack open and find some factual answer inside, I find it useful to remember that it’s just a perspective. It’s just a belief that you’re taking on for today.

Shane:

That’s beautiful. Thank you so much, sir. This was a phenomenal conversation.

Derek:

Thanks, Shane. You asked great questions, and I am so psyched to continue reading your book tonight.