The Learning Leader Show With Ryan Hawk

659: Derek Sivers - Not Waiting for Permission, Hell Yeah or No, Leadership Lessons From The Dancing Guy, & Why The Standard Pace is for Chumps

56 min
Oct 26, 20257 months ago
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Summary

Derek Sivers discusses how questioning institutional defaults, maintaining high standards through deliberate practice, and understanding the difference between explorers and leaders can accelerate career growth and business success. He shares lessons from graduating college in two years, building CD Baby into a $22M company, and delivering a viral TED talk on leadership.

Insights
  • Most institutional pacing is designed for the slowest person; ambitious professionals can accelerate significantly by questioning defaults and finding alternative paths
  • Deliberate practice and obsessive editing (100+ rehearsals, year-long manuscript refinement) separate exceptional work from adequate work
  • Explorers innovate and discover; leaders execute with clarity and unwavering direction—conflating these roles creates frustrated teams and poor leadership
  • Early-career professionals should say yes to many opportunities to discover what the world actually wants from them, not what they predict it wants
  • Creative differentiation in mundane interactions (shipping emails, customer communications) can generate organic viral growth and brand loyalty
Trends
Rejection of hustle culture in favor of intentional scarcity and deep focus as a competitive advantageShift from expertise-driven to curiosity-driven leadership that questions assumptions rather than enforces doctrineViral marketing through authentic personality and creative deviation from industry norms rather than paid campaignsCareer path non-linearity: success often comes from unexpected pivots rather than planned progressionEditing and refinement as a core business discipline, not just a creative practiceSabbatical and selective engagement models replacing always-on availability as a status signalEmpirical testing of beliefs and prejudices through direct experience rather than accepting inherited narratives
Topics
Questioning institutional defaults and standard operating proceduresDeliberate practice and obsessive refinement for excellenceLeadership vs. exploration archetypes and team managementEarly-career strategy: optionality vs. specializationViral marketing through authentic differentiationHell Yeah or No decision framework and its limitationsWriting and reflection as tools for clarity and learningBelief systems and challenging inherited assumptionsCD Baby business model and independent music distributionTED talk preparation and public speaking excellencePace acceleration and institutional skepticismFirst follower leadership dynamicsValue creation as a measure of career successSabbatical and selective engagement strategyExploration vs. execution in business contexts
Companies
CD Baby
Derek's company that became the largest seller of independent music online; sold for $22M and he gave the money away
Warner Music
Derek's employer after Berkeley where he worked in the tape room and learned about alternative networking approaches
Berkeley College of Music
Derek graduated in two years instead of four by learning at accelerated pace from instructor Chemo Williams
TED Conference
Platform where Derek delivered his viral 3-minute talk on leadership lessons from the dancing guy with Bill Gates and...
People
Derek Sivers
Entrepreneur who built CD Baby, gave away $22M, and created viral TED talk on leadership and movement dynamics
Chemo Williams
Berkeley instructor who taught Derek four semesters of harmony in one hour, demonstrating that standard pace is unnec...
Alan Tepper
Warner Music employee who walked in without a job offer and created value by connecting music catalog to advertising ...
Ryan Hawk
Host of The Learning Leader Show who interviewed Derek Sivers about leadership and excellence
Seth Godin
Author of Tribes and Purple Cow; influenced Derek's thinking on movements and mentioned CD Baby's shipping email
Malcolm Gladwell
Author of The Tipping Point; influenced Derek's analysis of the dancing guy video as a movement metaphor
Peter Gabriel
Musician who approached Derek after his TED talk to praise it as the best thing he had seen
Tony Robbins
Motivational speaker who was in front row at Derek's TED talk and later tweeted about it
Bill Gates
Sat in front row during Derek's TED talk delivery, creating high-pressure speaking environment
Larry Page
Google founder who attended Derek's TED talk as a VIP audience member
Tim Ferris
Podcast host and friend of Derek who mentioned him in conversation with Ryan Hawk
Quotes
"The standard pace is for chumps. You can do so much better than that."
Chemo Williams (via Derek Sivers)Early in episode
"Most things are paced so that the slowest person can keep up. But if you're driven, if you are motivated enough, you can go so much faster than the standard pace."
Derek SiversDiscussing Berkeley acceleration
"I'm not going to put a single sentence out into the world that doesn't need to be there."
Derek SiversDiscussing editing philosophy
"Hell yeah or no is a specific tool for a specific situation. It's the wrong strategy to be using straight out of college when you'd be smarter to say yes to everything because opportunities are like lottery tickets at that point."
Derek SiversClarifying Hell Yeah or No framework
"A leader goes in a straight line. An explorer is trying everything. If you're calling yourself a leader but you're actually an explorer, you might need to take a different approach."
Derek SiversDiscussing explorer vs. leader archetype
Full Transcript
This episode is brought to you by Insight Global. Insight Global is a staffing and professional services company that builds world-class technical teams for clients around the globe. If you need help with your applications, infrastructure, or data layer, Insight Global's team of technical experts can build custom or manage services to deliver the outcomes you desire. Getting the most out of your technology can be tough, but growing your business with the right technical solutions can be magic. Visit InsightGlobal.com slash LearningLeader. That's InsightGlobal.com slash LearningLeader today to learn more. Welcome to The Learning Leaders Show presented by Insight Global. I am your host, Ryan Haugh. Thank you so much for being here. Go to LearningLeader.com for show notes of this and all podcast episodes. Go to LearningLeader.com. Now on to the night's featured leader, so great Derek Sivers, the entrepreneur who built CD-baby from nothing into the largest seller of independent music online. Then he sold it for $22 million and gave the money away. You might know Derek from his viral TED Talk called How to Start a Movement about leadership lessons from a dancing guy or from his books including anything you want, hell yeah or no and useful, not true. During our conversation we discuss why the standard pace is for chumps and how you can go faster at whatever it is you're doing. And Derek shares how he put together his viral TED Talk and how he handled having Bill Gates, Tony Robbins and the founders of Google sitting in the front row staring at him while he gave by the way a three minute TED Talk that earned him a standing ovation. And then we close talking about the difference between explorers and leaders. Ladies and gentlemen, please enjoy my conversation with Derek Sivers. So you're 17 years old and you're about to start your first year at Berkeley School of Music and you meet this guy tell me from pronouncing his name wrong, chemo Williams. That's right. And you have a conversation with him. What happened next? It was about two months before I was set to go to Berkeley College of Music and I mentioned to him that I was going and he said oh really he said I used to teach there. He said I have an idea. He said come by my studio tomorrow morning at 9 a.m. and I think I can help you graduate Berkeley in two years because it's a four-year college. And I showed up at 9 a.m. which surprised him because he said that he often says this to people that show some mild interest and nobody ever shows up at 9 a.m. But there I was at his door at 9 a.m. ready to go and that impressed him. And then he sat down with this intense pace and taught me four semesters of harmony classes in an hour because he just went really quick and intense and I was quick and up to keep up with it. And what I lacked, he said learn this over the next week and we met a week later and he taught me four semesters of Berkeley College of Music's arranging classes in two hours. And we met maybe four times total and that was enough for him to teach me essentially two years of required courses at Berkeley because his main point was most things are paced so that the slowest person can keep up. But if you're driven, if you are motivated enough, you can go so much faster than the standard pace. He said the standard pace is for chumps. You can do so much better than that. You can graduate a four-year university in two years. And I did. Man, what do you draw? I mean, 17 years old, what a great life lesson. How have you taken from those moments with chemo to say, wait a second, I can go way faster. This pace, that's for chumps, right? The regular speeds for chumps. What have you taken from that that has helped you later on in life? Institutional skepticism. When someone says you have to go through the usual channels and file the forms as such, I think not necessarily. And when someone says that'll take this long or you need to do this first, I think there's probably a hack that's probably the standard way that most people do it, but there's probably a better way. Derek, let's say somebody who works in a corporate America or just a corporate job in the world. And they're ambitious and growth focused for the right reasons, right? They want to provide for their family. They want to enjoy their work. They want to build a career. And then there's a slightly different way that you've looked at it. But I think that's a lot of people and I still love to do whatever I can to try to help them. What could they take from that story to say, maybe there's a different way? Maybe there's a better way to do this thing than just try to climb the regular corporate ladder like everybody else is trying to do. Here's a real example. After I graduated Berkeley College of Music, I got a job at Warner Music in New York City. Even the way I got the job, quick aside, was because of visiting speaker from New York City from a different music company was visiting Berkeley College of Music. And as he walked into the classroom to begin speaking, I heard him say to the teacher, are we starting now? And the teacher said, yeah, and he said, I thought we were going to eat first. He said, Oh, man, I haven't eaten lunch. I thought we were going to eat first. So I quickly, while the class was getting settled, I dashed out to the pay phone. And I called Supremes pizza, whose phone number I had memorized. And I had them deliver three pizzas to room number three, 14. And so about 30 minutes into his talk, the pizzas come. And I paid the guy and brought the pizzas up to the speaker who looked at me and said, all right, good one. I owe you one. And we kept in touch for the next few years. He's the one that got me the job at Warner Brothers because he heard them mention in passing that they were hiring a new guy to run the tape room. And he said, I've got just the guy for you. And he called me in Boston and said, I got you a job in New York City. If you can start on Monday. And that's how I got the job. I never had to interview or anything. His recommendation alone just got me the job. So that's not even the real story I'm telling them. That's just another example of how there's always a different way than the usual channels, right? Be proactive, take action, like get it done, be valuable. That's something I will talk about that in a second. But yeah, I want you to finish the story. So while I'm working at Warner Brothers, there is one empty little office that one day wasn't empty. And there was a guy there named Alan Tepper who just showed up and said, Hey, I'm Alan. I've started working here. And I said, Oh, what do you do? And he's, well, I don't officially work here yet. But I told them to just give me a desk. And I'm going to make the company a lot of money. I said, how? He said, because I used to be in advertising. And I saw that Warner Brothers is not proactively pushing their music catalog to advertising agencies. So I said, just give me a desk, give me a phone. You don't have to pay me. Let me show you what I can do. Alan Tepper, later that year made more money for the company than anybody had in years. And officially they did hire him eventually. But the company was not hiring. He walked in saying, I know how I can make you more money. Just let me show you. And that's it. I love this story because you don't have to wait until a company's hiring. If you can get a little insight into an industry or a company and see how you can benefit them, you don't have to wait for them to hire anyone or say that they're hiring. You can just walk in and show them what you can do for them and say, you don't even have to pay me. Let me show you. And I've seen this work in action. I think it's a great approach. I love that. One of the things you also did was give a talk to the Berkeley students. And it was titled six things I wish I knew the day. I started Berkeley. And I think the one that I pulled out from that six that I want you to expand on is very similar to what Alan Tepper did. And that is when done be valuable. Right. When you leave here, you said to them, head to the business aisle of the bookstore and start reading a book a week about entrepreneurial thinking, things like marketing. Make sure you're making money. That's a way to continue on and make sure you're doing something to add value to others. Sometimes you will think like, oh, I'm just going to be good or I'm going to make this art or I'm going to do this thing. And you said, no, there's a part of it that you got to create a business. You got to add value to other people. You have to make money. And I think to be excellent at whatever you're doing, constantly thinking about how am I adding value to others is a good way to approach it. How have you used that in your life? First, I got to give a little context that probably people listening to this podcast say, well, yeah, duh, making money. I know, especially on the internet, it feels like that's all everyone's talking about. It's how to make money. But at a music school, there's this tendency to go too deep into chord voicings and tombur and the structure of your second verse as it leads into your pre-course and whatnot. It's just diving deep into the mechanics of music, which is important. It's super important, which is why elsewhere in that talk, I say, shut out all distractions, stop reading all media, dive deep into these things that I just mentioned. But then, yes, when you're out of here, shift your focus and find a way to make that valuable to others. Because we've all heard the phrase starving artist. The essence of the starving artist is someone who is spending all of their time on work that's valuable to them, but not valuable to others. Meaning, they might be pouring hundreds of hours into some expression of their feelings of the meta universe we all live in, but other people can't relate to it. And so nobody wants it, nobody's interested, but that person is spending all of their time on this thing that nobody else is interested in. That's a problem. It's a very common problem for artists, writers, musicians. So the point was keep in touch with the objective measure of value we call money, which is so loaded with baggage. But if you think of it just as a neutral measure of value and try to find ways to make money with your art, it's a way of making sure that what you're doing is valuable to other people, not just to you. Yes, I think the key learning for anybody, whether you view yourself as an artist or not is, what am I doing to add value to the lives of the people around me? I learned this in sports early in my life there, where if I didn't give our team the best chance to win. I played quarterbacks, only one guy gets the play, then they're going to play the other guy. And that happened to be in college, right? Where the coaches looked at me dead in the eyes and said, that guy gives us a better chance to win than you do. He's adding more value to our team than you do. That's a great lesson to learn, man, especially when you're 19 years old, as you learned valuable lessons at that age and your formative years, because that's kind of how the world works. Like if you add value to people's lives and help them and put them in a better position, you are probably going to have a lot of work. And if you don't, you got to find a way to do it. I think, I don't know. What do you think? I see you thinking right now. Yeah. Well, I'm thinking about when you had the dating coach on how a hard thing with dating is to how to see yourself through other people's eyes. And this kind of the same thing, isn't it? To get out of yourself and stop thinking of the intrinsic internal value of what you're doing to you and think of it as how valuable it is to someone else. Yes. I think that something would be regularly thinking about that shows high levels of emotional intelligence, high levels of self awareness, supreme levels of intelligence. There's a million different things to get to with your story, Derek. I love it. We've talked about it in the last time. But one of the things you did is I love how you put together one of the many viral things you've done, which the title, if you just search leadership lessons from the dancing guy, maybe it'll also say in parentheses, first follower, I'm curious, what were you thinking when you put that talk together with the video? And then maybe you can describe it too for those who haven't seen it yet. Sure. 2009, I was living in New York City. And there was a video, maybe it was Reddit, maybe it was dig. I don't know what it was at the time that just somebody showed this video of a guy dancing alone. There was this shirtless guy dancing kind of like tripping balls as we'd say, dancing at this music festival, just all alone. And people are just casually sitting there looking at the funny shirtless dancing guy. And at one point, somebody jumps up to imitate him and starts doing all the same moves he's doing. And because one guy imitates him, a second one jumps in right away. And now the two of them are imitating the shirtless guy. And then right away, three, four, five, six, seven, eight, 20 people all jump in to do the same thing because that first one had the confidence to do it. And I had just finished reading two books. One was tribes by Seth Goden. And one was the tipping point by Malcolm Gladwell. And both of these books describe how actions start a movement. And so while I was watching this video of the dancing guy, I thought this is kind of like a visual metaphor of what Seth Goden's tribes in Malcolm Gladwell's tipping point are talking about. So I just blogged it. At the time I was blogging almost every day. So just that day, I posted a blog post showing that video saying, isn't this kind of like making a movement? I said, but notice how we focus on the shirtless dancing guy. But actually, it was the first follower. That first guy that jumped up, that's what made everything else happen. Until then, it was people keeping their distance from the freak. But the first person jumped up and started imitating him. That let the second person do it. And then there was no reason not to. Because other people had already begun. And I thought it was really interesting then how the first and second followers were the ones that really showed everyone else how to follow. And then, of course, you think of the metaphors in real life. Like if you find some lone nut doing something great, it might be a mad scientist in their computer basement somewhere. But if you find somebody doing something great, one of the best things you could do is to follow that person and show other people how to follow. And then when you put it together, there was a TED talk, right? Yeah, it was a TED talk. Oh, yeah. Okay. So sorry. So yeah, I just blogged it. And that was it. But then a few months later, the TED conference put out a call saying we're taking submissions for new talks. So I just submitted that and they said yes. And then began the day that I thought my heart would explode is I was there at the big main stage TED conference. I mean, like Al Gore, Surgey, Brynn, Larry Page, Tony Robbins, all of these VIPs, Bill Gates is sitting right there. All of them in the front row looking at me like, all right, anonymous speaker I've never heard of. Impress me. So I got up on stage and delivered that talk to that room. And it was terrifying. Because I mean, you made it look easy. Well, thank you. But what was terrifying is it was like memorizing a four minute long monologue. Like if you think of being in a school play or something like that, you have to memorize a monologue. Because if I forgot a single sentence, the whole thing gets out of whack with the video. I have to memorize word for word this four minute long speech about leadership in order to match up exactly with the video of the dancing guy. And to do that while my heart was racing was so scary. I thought it was going to have a heart attack. But God off stage and one of the coolest moments of my life is the musician Peter Gabriel, whose music I loved for years saw me interrupted his conversation with someone else and ran up to me to shake my hand saying it was the best thing he had seen. And then later that day, Tony Robbins and a bunch of other people tweeted it and I was very proud. Wow. How many times did you practice it? Oh God. At least a hundred. Really? Yeah. Over and over and over and over again. I would just call up friends and say, come on, let me do this one more time with you on the phone. Okay. Hit play on the video. I'm going to do this with my eyes closed now. Let's see how I do. Wow. I think that's the inspiring part to me, Derek. It means it is possible. We can do it. Now, you're a really smart dude, but it's the practice. I had Nikki Glazer, the stand-up comedian on this podcast and to hear her talk about the number of times she has wrapped her material before any of us see it. It's very similar to what you're saying. And so to me, that is inspiring. Now it's a ton of work. And you got to be super dedicated to excellence and wanting it to be great because you probably you wrote the blog. You knew the material well enough where you could have just kind of rift on it. And it probably would have been decent. But instead, you're like, I want this thing to be excellent. I wanted to be as good as it could possibly be. So I'm going to practice it with my eyes because I'm going to practice it so many times that I can't forget. I think there's a lot to take from that. It started this idea of wanting every sentence to matter. So anybody listening here, if you check out any of my books, you'll see that they're all very short, like my three-minute TED Talk. They offered me to 18 minutes. I said, no, I think I can do this in under three minutes. So same thing with my books. My books are 90 pages, 100 pages. They're meant to be written in hour. But the reason is the rough draft is a thousand pages. And then I will literally spend full time for one or two years to squeeze it and squeeze it and squeeze it and chop every sentence that doesn't absolutely positively need to be there. And in the end, what's left is this itty-bitty little book that's almost like poetry because it's so succinct. But the idea is I'm not going to put a single sentence out into the world that doesn't need to be there. I think a lot of us as leaders could learn from that. Think about your next quarterly business review, Town Hall meeting. Monday morning meeting. Thinking about pruning that thing down, making it so that every word that comes out of your mouth has to and nothing more. It's kind of like Robert Green, do not speak unless you can improve upon the silence. But thinking about that, for everything you say and do, we'd have a lot better meetings, man. Hell yeah. That's one of the things you said speaking of that. So a little bit of the background, I asked you to come back on because when I was talking with Tim Ferris, one of your good buddies, he talked about you. He brought up quotes of yours. We talked about you off air too, you know, all this stuff. And so I sent that to you like, hey, you know, I thought you might want to check this out because we talked about you a little bit. And I'd love to have you back on. And you said basically like you're going to go on a sabbatical from doing podcasts, but hell yeah, let's do it. And you have this thing that has not been copied, I think by tons of people of basically hell yeah, or no. So either I'm going to go do it 100% give everything I got or it's going to be zero. I'm not going to do it. Can you go deeper on that hell yeah, or no, that's also the title of the book. But that mentality of how you approach projects, how you approach life in general. We've all felt the pain from saying yes to too many things so that you're spread too thin. And I did this like everyone else at a certain point I realized that if I were to say no to almost everything, what it would give me is the space and the time. So that when that occasional thing comes up, that I'm actually really excited about, well now I can just fucking smash it. I can throw myself into it entirely and do something like the hundred closed eye practices of a speech or an entire year editing a rough draft down to a hundred pages. I have the time to do something like that because I've said no to almost everything else. So it's about leaving space instead of filling your space. It's leaving the space so that when that opportunity comes up, you can say yes absolutely and I can start right now and I can throw myself into this entirely because I said no to almost everything else. What's the response to that book into that mentality from people like I'm more curious about the negatives because yes, I'm glad you brought that up. I personally have borrowed this from you, stolen it from you, share it with like leaders I work with who have the counters that you've probably seen them back to back to back to back. That's every day. That's like five. Sometimes they meet on Sundays like and I'm like, dude, you got to are these all hell yeses? Like all of them, every single one of those, every one of them, you know, they're pre-important, man, I got to do this stuff. I have a lot of people who report to me and I'm like, wow, I don't know, I don't know. So I'm just curious to the response you get to that. Well, two things. For one, it's cute when people contact me out of the blue and say, well, I'm sure you're very busy, but I say, no, I'm not busy because busy to me implies out of control. Yeah. You're busy if you've let other people shove shit into your schedule. If you leave space, then to me, it leaves time to think part of the reason people buy my books and want to hear my thoughts is because I'm this weirdo that spends a lot of time thinking. I don't spend a lot of time doing. I don't have a full schedule and because of that, I'm able to sit around and think for six hours about the impact of language on our approach to life or something like that, that most people don't have the time to do, but I do because I sold my company and retired and I spend my time thinking. So if you tune into my thoughts, ideally, you're going to hear something you haven't heard before because I just spend more time thinking about the kind of stuff that most people don't have the time to think about. That's why you outsource it to me. Okay, so that's one hell yeah or no aspect, but where I thought where you were going with this when you said the negatives are that I get emails from people that are straight out of college saying, hey, I saw this hell yeah or no book of yours and I'm applying this to everything now. I'm not taking any jobs unless it's really a hell yeah and I say no, no, no, no, no, no, no, no, look, it's one tool in the toolbox. Yeah, you don't use the monkey wrench as a hammer. You don't use the monkey wrench as a toothpick. It's a monkey wrench. It's meant for a certain situation. So hell yeah or no is a tool for when you're overwhelmed with options and it's time to raise the bar all the way. It's the wrong strategy to be using straight out of college when you'd be smarter to say yes to everything because opportunities are like lottery tickets at that point. The more the better, sleepless work 21 hours a day say yes to nine jobs at once. If that's what it takes to open those lottery tickets and then once something's rewarding you and pays off, then you say no to these other things you double your efforts and raise the bar all the way. But hell yeah or no is a specific tool for a specific situation. Okay, I like that clarification because I think yes sometimes people just hear the part they want to hear and then yeah, you're 23 and you're like, I don't know. I'm like, dude, the job you get when you're 23 for most of us, most, you know, I don't mind cubicle pounding the phones 60 cold calls a day. Sometimes you go over 60 in a sales job. Great job though. It was hard. I didn't love it most days, but I grew to get good at it and I grew to develop skills that have helped me for the rest of my life. If you would have said like, well, is that a hell yeah or do you love that job? I'd be like, no, are you kidding me? When I got done with college, that's what I thought I was going to be doing. Of course not, but I'm so grateful for that experience and that opportunity that it's maybe better and all of the things. Now, I want to shift there to I think this is a leadership thing. You may view it as a creativity thing. So when you were running CD babies, so this is your company that you already mentioned that you have sold when somebody makes a purchase of something, you usually get like a canned email like, hey, you ordered these socks and they're going to get there in three days from Amazon or whatever. And you had that same thing initially when people would order a CD, but you changed it. So can you tell me how you changed the, hey, you bought this CD email? I love that you said socks and we'll come back to that in a minute. Okay. But imagine this, yeah, it was 1998. I had just started my little online record store in my living room. No employees, just me, a little tiny website I made myself that had a hundred musicians selling their music through me. And yeah, the default shipping notice was the default. It said your order has been shipped. It's on its way. Thank you. And I just looked at that and thought, I can do better than that. Like, why be normal? I think this is a lesson that every musician learns is you don't want to write a song that somebody else has written. You want to write something that nobody's done before. Say the lyric that's never been said before. And so same in business. Don't just do the same thing that everybody else is doing. Ask yourself constantly, what has nobody done before? What would add something to the universe and make the world a better place? Surprise somebody. Make eyebrows go up. Not down. So in 10 minutes, I wrote this silly little thing saying your CD has been placed onto a satin pillow and a hush fell across the crowd as we lit a candle and put your CD into a gold-lined mailer and onto our private jet, which is on its way to you in Dayton, Ohio. On this day, Friday, August 13th, we hope you had a good time shopping at CD Baby. We're all exhausted and your picture is now on the wall as customer of the year. We can't wait to hear from you again, etc. And that's it. I wrote it in 10 minutes. It was a bit of silliness. It became the default shipping notice. I just said it to automatically send that to everyone that bought something. But because it was so weird and different, people started forwarding it to their friends and then blogging about it and then talking about it. Seth Godin had a chapter about it, I think, in the Purple Cow or a mention of it somewhere in Purple Cow and other business books mentioned that particular email as one of the most viral shipping confirmation emails ever. And then just two years ago, here in Wellington, New Zealand, I heard about compression socks because I was flying a lot and somebody said you should look into having compression socks if you're sitting on planes a lot. I don't know what compression socks are, but I went online, typed New Zealand, compression socks, found a seller, ordered two pairs. The next day, I got an email that said, your socks have been placed onto a satin pillow and into a hush fell across the crowd as we lit a candle. And your socks are now on our private jet on their way to the, and your pictures on our wall is customary the year. And I said, wait a second. Are you doing this because you saw my name in the shipping notice? And the woman running the shop said, what? Sorry, no, I don't, what are you talking about? I said, I wrote that 25 years ago. I wrote that. And yeah, she had no idea. She just copied it out of a book. Oh my God, that is awesome. Again, though, you're thinking differently. And anybody can do this. Anybody can think differently about how you do, and it's hard to quantify what that did for your business, but the virality of it, how creative it was, caused it to spread. And then ultimately had to have had an impact on your business. I had to. Oh, yeah, like literally hundreds of customers that I knew about that mentioned it said, I heard of you from this blog post about your shipping confirmation. I heard of you because of this book mentioned your shipping confirmation. So a lot of people heard of me because of that silly email, I wrote in 10 minutes. But the bigger deal is not looking to the outside world to see what we can imitate, but to look at what's been done already and see how you can try something different. It's harder, but I bet part of why this happens is because you were writing a lot. You were getting your thoughts out of your head onto the page regularly. You published a lot of them. Maybe some of them you didn't, but I think that is the ultimate tool for clarity. It's the ultimate tool for teaching. And I think teaching is the ultimate tool for learning. This show is called the Learning Leader Show. I'm very focused and fascinated by people who are chasing down their curiosity with great rigor and trying to learn to grow to get better and hopefully positively impact the world and other people. Can you talk more about the importance of being a regular writer of getting those thoughts out of your head onto the page? For me, it's healthy doubt, skepticism. It's questioning the defaults. If you jot down your thoughts, ideally, you occasionally question them. If you say that person wronged me, ideally, then you add a question mark. That person wronged me? Maybe. Maybe not. How can I look at that situation through another light? We need to adopt AI. Let's add a question mark. We need to adopt AI. Everybody says it's the greatest thing. Is it necessary? Do we have to do this? It gives you time to question assumptions and to not just stick with your first impression. Our first thought is an obstacle. We should not be honoring the thought that came to us first. Like a brainstorming session, you need to acknowledge that that's the first idea. Okay, what else? Give me another one. And then don't stop it too. Don't stop it. Three, make yourself come up with a bunch of different perspectives. Sometimes the silly ones can help seed a really great idea that you never would have thought of if you didn't have the silly step in between. But all of this is taking the time to go past your first thought, past that obstacle on to the more interesting perspectives. Just by taking the time to think through it. Whether that's in writing or just make sure that just in case somebody is a verse or allergic to writing, it can also just be talking into a voice recorder. It could be talking to your cat or talking to a friend. It could be journaling into a paper notebook. It could be typing into a text file. Just some way of collecting your thoughts and just giving yourself the time to reflect and think. Well, I think part of it, this comes from your book Useful Not True, is that we just make these assumptions that our beliefs are true. And I like this part. You said, for hundreds of years, people worshipped Zeus and Athena and others. And now, this was crazy. Now we call that mythology. Those are myths. But now when it comes to our beliefs, no, no, no. Those are just true. Other people's beliefs, those are superstitions or those are myths. But my beliefs, they're true. That part really spoke to me because I think as a learning leader, as someone who's chasing down my curiosity, really, really hard, I'm always questioning like, maybe there's a better way. Maybe there's something I don't know. Maybe what I currently think is wrong. And if I find that, I get pumped. I'm happy. Like I found a better way. This is great. So bringing in this kind of like, Hey, people used to like worship these gods. I think that's why it's worth it for us to question our own beliefs because that could be our beliefs. You know, I don't know. Yeah. What do you think? I went to China for my first time last year, only because my boy had watched Kung Fu Panda enough that for his school holiday, he asked if we could please go to China. So I thought as part of his education, I should take him to China. But I expected it to be awful. You hear American news stories about this awful place. It's always spun negative with the dystopian government and the oppressed people and the ghost towns from the stupid real estate developers that built skyscrapers that nobody wanted. You only hear the negative. But if you go there, it's wonderful. The cities are amazing. The people are happy. Just forget every other measure. Just sit and observe all the smiles you see in the middle of the major cities. People are happy. They're thriving. They're productive. The cities are clean and the people are entrepreneurial and driven and optimistic about the future. And it's amazing. So I've been back four times in the past year more than anything really surprised how pleasant this place is that I've always been told was part of the evil empire. And then you think about how many other things we've been warned against are not actually bad. It's just that maybe the two governments or even the two corporations have something against each other. And so they tell us to agree with them. But there's so many different perspectives to be had out there. And it's worth it to go experience them, to go try to gain your own perspective and approach it with curiosity instead of judgment, right? There's like this spectrum. Yes. So now I even use this as a compass that if I noticed, I'm prejudiced against something, that makes me want to go into it to find out more about it. So let's give a non-political example. To me, Burning Man sounds awful. Me too. It sounds like the last place I'd want to be in a desert for a week with no food and water, except what I bring in myself and everybody's on drugs and it's all crazy. It sounds terrible. Therefore, I should probably go. I saw what's another insane clown posse. I don't know their music. I've heard maybe one song once, but I think the fans of insane clown posse paint their face black and white and they call themselves jugaboo or something like that. And then once a year, somewhere in Indiana, I think they have the annual jugaboo festival where all the fans of insane clown posse get together for this crazy festival. And somebody passed a little YouTube clip of it and I thought, that sounds awful. I should go because I'm full of prejudice against it. Yeah. Therefore, I should steer into it. It's kind of like the Lincoln quote, right? I don't like that man. I must get to know him better. I never heard that. That's Abraham Lincoln. I think so from what I wrote on the internet that might not be true. But from what I've read, yeah, I don't like that man. I must get to know him better. I think that is kind of a broader way of, you know what's funny is like usually when you do meet those people at times, I've seen people on the internet where maybe I cringe a little bit and then I'll be at a conference or something and we're both there. I'm like, good dude. He's a good guy. Yeah. Yeah. Good guy. Yeah. He was great. He was great. We had fun. Maybe you'd share it a meal or something. It's like, yeah, good guy. There's one thing to darek about and use for not true about leadership and exploring. And I wanted to touch on this because you've openly talked about you not being a good leader and not many people do that, especially on a leadership podcast where they admit like, no, I'm not really that good of a leader. Yeah, you create this business and it grows and you sell it and make a bunch of money and now you do whatever you want. And you have for a while now. But can you talk to me about the difference between explores and leaders? Yeah. I learned this lesson in hindsight, hard lesson learned. While I was running my company, I was actually a pretty bad leader as proven by how frustrated my employees were that I loved changing my mind. And I loved changing my mind for the reasons that we've talked about right here. Interspection, reflection, considering other approaches. I'm always hoping to change my mind. That's one of my favorite things to do in life is to change my mind. It's great when I find a new perspective that changes my mind. But my employees were so frustrated by this that only years later in hindsight, looking back, I can see now why I was such a bad leader. It's because let's use the archetype of the 1800s explorer from England that gets on a boat for six months to go to the unexplored jungle, machete in hand with the pith helmet, a few workers carrying the baggage. But for the most part, it's an explorer going into uncharted lands to hack around and see what's there. To go where nobody else has gone, maybe go up that hill, there's nothing up that hill. Let's go into this inlet. There's nothing in that inlet. What about this inlet? Oh my god, there's a gorgeous bay. Look at this amazing paradise bay in this inlet. Oh, nobody's ever been here before. This is a great harbor. This would be a great port. So then the explorer sends a message back to the queen saying, I've found this great harbor. And then the queen appoints a leader. Now, this is very different than the explorer who's trying everything. A leader is someone that goes in a straight line that says, we're going to this harbor, we're going to set up a city here. These are the benefits. This is how you will gain by doing this. Follow me. And the leader goes in a straight line. And if halfway there, somebody were to say to the leader, hey, what do you think about going to a different direction instead? The leader would say, shut up. Lock that man in the jail. We're going straight ahead. I'm not changing my mind. And the leader goes in a straight line to the destination with a clear mission undeterred. That's a great leader because that person is easy to follow. It's clear where we're going. Even if you're in the back of the crowd and you can't hear what the leader is saying, it's easy to see where we're going, what we're doing. And in hindsight, I see then the difference between the explorer and the leader and how I was just an explorer, which made me a really bad leader. But next time if I were to do it again and I wanted people to follow me, I would pause my explorations, declare a certain harbor to be the destination. And I would set that project as having a clear unwavering mission. Even if I personally might go explore some other things, I would declare this project to have a clear mission straight line easy to follow. Is that distinction to black and white? In the real world leadership is a little bit more messy than that. I think it's a little bit more gray. Whereas you can have some exploration and some set the vision and the objectives. And let's go. No deviations. Follow me. We're going. But the great ones I feel like also are curious enough and humble enough to listen to people on their team, even if those people work for them when they say boss or leader, dude, this part of the plan is actually not right. Like this part needs to be tweaked a little bit and a good leader say, hold on, let me think about that. Ah, you're right. We still have the same vision, right? We're still heading in the same direction. But yeah, what you're telling me, I missed on that part. Let me adjust, right? So like there seems like there is a little bit of gray in there. Whereas the explore versus leader thing seems more black and white. Two thoughts. Okay. Black and white examples are made intentionally purified for the sake of clarification so that we can see what we're talking about. Good call. But even in that metaphor of the leader going on the boat to the harbor across the world somewhere, yeah, you're right that ideally if there was a storm in the way, a good leader would not go through the storm. You'd go around the storm. The destination hasn't changed, but maybe the path changed or in that metaphor, you're right. If somebody looked at the map and said, hey, boss, by the way, I love how you said boss leader dude. Hey boss leader dude, we could actually get there better or faster if we were to take this alternate route, which you had not planned, but it actually gets us to the destination better. I think anybody listening to this yet, you get the metaphor for your own situation, but it's good to realize that some of us have started businesses for our own satisfaction of inexploring. Yeah. And you should be wary. If you notice that you were more of an explorer, but you're calling yourself a leader, you might need to take a different approach or keep your explorations personal and keep your business in a straight line, even if your personal interests are keeping you astray. What would you do? Would you get help from other great leaders? Would you ask them questions? Would you read their books? What you read tons of books I know? What would be your approach to be a better leader next time? I would just define it as a project, kind of like how we incorporate a company. You set up an LLC and you say, for this project, this project has this goal, clearly stated straight line. This is what this project is doing. Follow me to this destination that this project is out to pursue. We're aiming to discover this technology. We're aiming to solve this problem and just set it as a clear defined project so that then even if you hand that off to a different leader, that person also knows the clear aims of this. It's easier to communicate your marketing's easier. You're able to more clearly see exactly what this is, what it solves, how it will help, where it's going. Leave that as an individual project that goes in a straight line. I think my dad was so, and he still talks about this, being so good at being vividly clear in the message and narrating the journey and making sure we knew how we play a role in helping us get to whatever that thing is. And we're like, okay, I got it now. I can go execute on this thing. That's the job of leader. That was the rally the people and make sure you're clear enough as a communicator that they know where we're going, why we're going that way and how you specifically help us achieve this big thing, then you can get on board. Derek, I got one more question man before we run. This is also my appreciate you getting up early over there in New Zealand. It's kind of cool that this technology exists that I'm here in Ohio. You're in New Zealand. We can talk like we're just hanging out. But let's say you're meeting with one of those. We mentioned the early college grad when Hell yes or no might not always work for them. But let's say they're like, hey man, I want to, I want to leave a positive dent in the world. I really do. Like you have. But I'm not really sure yet how or what I'm going to do. What are some general pieces of life slash career advice you give to that person? If you see yourself from the outside, like we talked about earlier with the starving artist, it's almost impossible to predict what the world will want from you. You can read the stories of successful people that maybe moved to California to take a job in insurance, but then suddenly randomly got a job as an actor because somebody saw them in a restaurant and saw they fit the part of a Haggard Army general. And they took that job and it ended up being their biggest success. You never know what the world wants from you. So therefore, it helps to try lots of things and not get too hung up on one thing that your guessing is going to be your contribution to the world, but it might not be. I'm going to use a music metaphor here. In my years in the music business, I'd occasionally run across somebody who had written the song, one particular song that meant the world to them. And they kept trying to push that song onto everybody, but people just didn't like that song. But it was frustrating for them because they said, no, this is the song. This is the song. The song has great value. But listen again, maybe you'll like it the second time. They were trying to push this thing that people didn't want. And then I see that in business too. Somebody that has an idea that they're just sure that the world is going to want this, but the world doesn't want that. And it's unwise of you to keep persistently pushing without changing. You need to persistently keep trying variations until you find the thing that the world clearly tells you, yes, we want this from you. That's what happened when I started CD Baby. I had done many, many, many things. I had a booking agency, a record label recording studio. I had my own music. None of it went well. It was just failure, failure, failure, failure. And then this silly whimsic little thing I did on the side to help a few friends. That's the thing that took off and it feels such a difference. Suddenly all the doors that had been locked were suddenly opened to me. Everybody that had been booting me out suddenly was inviting me in. And I never could have predicted that it was that one thing that would have been the big success. So do lots of stuff. Try many things. Keep yourself out there and listen closely to what the world is telling you. It wants from you. Yeah, you never know, but you got to like keep chopping, like keep going, keep trying to add value to other people's lives. And like eventually, it seems like things find a way of working themselves out. Derek, part of the reason I love your approach just in general to life is your dedication to excellence is your willingness to do a lot of the hard work that nobody sees to edit down these massive books down to small ones where there is literally not a single wasted word. I even read the transcripts that you've published of podcasts you've been on, including this podcast. And even the transcripts are edited beautifully. I know I don't speak as well as what it looks like in those transcripts and so I'm thinking, was I really that good? I'm like, no, obviously I wasn't Derek edits them because he cares about even the transcripts that he puts out. So like this dedication to excellence, these high standards that is inspiring to me. And so I just want to make sure you know that I appreciate that. And I would love to continue our dialogue as we both progress, man. Thanks, Ryan. I really appreciate it. So good. It is the end of the podcast club. Thank you for being a member of the end of the podcast club. If you are sent me a note, Ryan at learningleater.com. Let me know what you learned from this great conversation with Derek Sivers. A few takeaways from my notes. The standard pace is for chumps. Most things are paced so the slowest person can keep up. You don't have to go that slow. In fact, you probably shouldn't think of ways you can increase your pace much like Derek did by graduating from college in two years instead of four. The standard pace is for chumps. Next, we should question our beliefs for hundreds of years. People worshipped Zeus, Athena, and others. Now we call that mythology, they're myths. But when it comes to our own beliefs, those, no, no, those are just true. Only others beliefs are myths and or superstitions. We should question our beliefs too. We should get excited when we find that something we had originally thought to be true turns out not to be. I love that. Then the shipping email he wrote for his customers at CD Baby initially. He was like everybody else when the CD was actually shipped. The first note was just normal. Hey, your order has shipped today. Please let us know if it doesn't arrive. Thank you for your business. Then he changed it to a variety of fun creative things. One of them being your CD has been gently taken from our CD Baby shelves was sterilized contamination freak gloves and placed onto a satin pillow. The whole point is to be yourself. Be different. You don't have to do it like others do. In fact, you probably shouldn't be creative. Be funny. Enjoy it. Create something that might make somebody forward to their friends or write about it in a book or want to spread a cool story. We all can do that. Once again, I would say thank you so much for continuing to spread the message and telling a friend or two. Hey, you should listen to this episode of the Learning Leader Show with Derek Severus. I think he'll help you become a more effective leader and because you continue to do that and you also go to Spotify and Apple podcasts and write a thoughtful review and rate the show. Hopefully five stars and subscribe to it doing all of that helps me continue to do what I love on a daily basis and for that I will forever. Be grateful. Thank you so so much. Talk to you soon. Okay, wait.