Interviews → Jenny Blake

Jenny:

Hi. I’m Jenny Blake, your host of the pivot podcast, an author of the book Pivot: Turn What’s Working For You Into What’s Next, which comes out with Portfolio/Penguin in September of 2016. In this podcast, I talk with peak performers to reverse-engineer their most successful career Pivots, interview experts on what it takes to be agile in a rapidly evolving economy and open the kimono on what happens behind the scenes of my book in business. You can learn to capitalize on risk, fear and uncertainty as the doorways of opportunity. My promise is that you will leave every episode with practical tips, tools and tactics. For show notes from this episode, visit Jennyblake.me/podcast. If change is the only constant, then let’s get better at it. Here we go.

Hello, everyone. I am super excited today geeking all the way out to be talking to Derek Sivers. I was fortunate enough that he said yes to be on the Pivot podcast. Derek is a musician, programmer, writer, entrepreneur, student and author fascinated with the usable psychology of self-improvement, business, philosophy and intercultural relativism. He’s an introvert, an INTJ, a minimalist, and a California native now living in New Zealand, Singapore and Belgium. I reached out to Derek after reading Anything You Want, which I read when it first came out in 2011 with Seth Godin’s Domino Project Team. And Derek just republished with Portfolio/Penguin. We share the same publisher. And I loved this book so much that I read it before bed one night and then I got about halfway through. I finished reading it the next morning. I gave my copy to a friend that day and I bought six more to distribute to other friend. So Derek, thank you so much for being here.

Derek:

Thanks, Jenny.

Jenny:

I don’t think I’ve ever done that. I recommend a ton of books. I’ve never actually bought seven or eight copies and distributed them within one week of reading a book.

Derek:

I did that with the book Geek in Japan. I’ve been to Japan like four or five times, and it’s a hard place to understand and even harder to explain to others. And I thought that the Geek in Japan did it so well that, yeah, that’s the most recent one that I went and bought a bunch of copies and just gave them to people like, “You need to read this.”

Jenny:

That’s awesome. What is Geek in Japan about?

Derek:

Japan.

Jenny:

Okay. No, you don’t say…

Derek:

It’s a Spanish guy that moved to Japan a few years ago and he explains the culture, explains the mindset really well. It’s also a very photo-filled book pointing out interesting things about Japan. But in the middle of the book, it’s really a chapter that really describes the mindset of Japanese culture very well.

Jenny:

That sounds fascinating. We’ll have to link to it in the show notes. I want to give a little more of your bio because this kind of sets the stage for Anything You Want. You created CD Baby in 1998 and ended up becoming the largest seller of independent music online with 100 million in sales for 150,000 musicians. And then in 2008, you sold CD Baby for 22 million and gave the proceeds to a charitable trust from music education. And my dad was also an independent musician for 25 years. He’s still teaching himself how to play guitar and writing songs. And I remember that he updated his – he uploaded his albums to CD Baby in the very early days. I tried to ask him how early, and he said, “Just when Derek was sleeping on his couch.”

So I know that that was a really empowering thing for my dad at that time. Yet, the thing that attracted me to you most several years ago was it was right around the time or maybe just after that you sold CD Baby. I remember thinking about how unique it was that you gave the proceeds to a charitable trust and watching your pivot out of CD Baby and how you choose what’s next and what you choose to say yes and no to. That’s been the real magnet for me. The numbers are so awesome and impressive and such a huge accomplishment and how you’ve navigated the choices afterwards in such an authentic way. There are just so much that we can all learn from that.

So can you talk a little bit about right when you sold CD Baby? Did already have a plan for what’s next or how did you navigate those first years afterward?

Derek:

Okay. The day I sold CD Baby, I actually had no plan that day. It was a really interesting liberating feeling going to bed that night feeling like, “Wow, after ten years, I’m no longer derek@cdbaby.com. Whoa! Okay. I’ve slept for like 10 hours that night, which I never do. I’m usually kind of five hours a night kind of sleeper. I slept so long that night with just as peaceful empty head. It was just such a mind vacation. And I thought it was going to last indefinitely. I didn’t know how long that feeling of wonderful emptiness was going to last. But then the very next day, I was eating breakfast or maybe it was a few hours later at lunch. And suddenly, I had this idea. It’s like, “Oh, I know what I need to do, “and I came up with my next idea. And in fact, I came up with a name for it. That was MuckWork. And you can even see the – I have to laugh when I look at the who is on the domain name. That day, literally the day after selling CD Baby. I read just through the domain name for my next company and immediately started programming all day long and built the database and started to like spill out everything the way it was going to work for this new business.

And I think I even, yeah, I hired somebody to help me manage it. And I was feeling very serious about taking the momentum from CD Baby and throwing that kinetic energy into the next thing and capturing the momentum and throwing the next thing, answering everybody’s big question about like, “So what’s next for you?” And I would say, “This is what’s next.” And I was going to try to make that company really big.

But after a few months, I had to ask myself what I’m optimizing my life for, which is a geeky way of saying, “What are you doing with your life?” But some people are all about making as much money as possible. And other people are all about getting as famous as possible. Other people are about, say, contributing as much as possible or making the biggest change in the world than to the universe, whatever you want to call it. We all have the different things that we’re being able to do. That’s like the underlying theme behind or under your actions. Right?

So I had to ask myself, “Wait, what am I really doing here? Because if I do capture this momentum from selling my last company and immediately throw all that momentum into my next company, aren’t I actually just staying on the exact same trajectory I’ve been on? Nothing will really be changing in my life. I’ll just swap out one company name for a different company name and really be doing the same thing living the same life.” Which for some people, yeah, that’s what you want to do. You do want to capture that momentum. And keeping the same trajectory is a good idea if that trajectory was heading the direction you want to keep heading, right?

But I guess for me, I really like change and I really like learning new things. I’m all about the process, not the goals. And I suddenly felt that starting this new company immediately we’d just be doing the same old process without really making a real change. So after a little soul searching, I decided to pause that. I even had to let go of the one guy I had already hired. And I started just making huge changes in my life very deliberate saying no to everything I used to say yes to and saying yes to everything I used to say no to. It’s doing things that were very unlike me all in the name of optimizing my life for maximum learning and maximum change, maximum experience, I guess you could say.

Jenny:

I love your metric of as much as possible. And as you said, for some it’s money, for others fame. It sounds like for you it’s learning and growth and change. And also, I would say from reading your book like a calm happiness that if that’s not present, there’s no maximizing anything.

Derek:

Right. Ideally, that should go without saying. But before we hit record on this call, you and I were talking about Singapore for a bit. That in Singapore, the cultural norm there is to go make as much money as possible. And it’s for good reason because only one or two generations ago, it was a very impoverished country. You could call it a third-world country. And now, it’s the richest country in Asia. And that just happened in two generations. And the reason that happened is because of this focus on making as much money as possible. It’s kind of a way of saying like, “Look, it doesn’t matter what your dreams and your goals are. It doesn’t matter what your personal tastes are. It doesn’t matter what color your parachute is. Just go make as much money as possible because that’s your duty to your family and your country. Go make as much money as possible.”

So, that’s still the main prevalent culture there. It’s slowly changing now that this new generation is growing up in an already affluent kind of – it’s not quite as desperate and maybe even the next generation will be told to follow their dreams by their parents that have plenty of money and gave up their dreams to make more money. But anyway, point is, yeah, there are some situations where it would be wise to go make as much as possible. Another situation is where it would be wise to stop trying to make money and just follow your dreams instead.

Jenny:

But that’s one of the things I loved most about your book is how – you counteract notions of the way it has to be in business. And that just because you start a business or a blog or fill in pursuit here, you don’t have to just scale at all cost. And I found it so interesting this recurring theme of question question those expectations. And you even say – one of my favorite lines of the whole book, I’m just going to read it so everyone can hear. You say, “To have something, a finished recording, a business or millions of dollars is the means not the end to be something. A good singer, a skilled entrepreneur or just plain happy is the real point. When you sign up to run a marathon, you don’t want a taxi to take you to the finish line.” Can you just share for all of us listening that philosophy in business and how you constantly pull back from that pressure to get outside funding or grow at all cost?

Derek:

Sure. The DNA of something matters, right? The DNA is what decides if something is going to be a pine tree or a penguin. So the DNA of CD Baby was just a favor that I was doing to my musician friends, for my musician friends. I never wanted to start a company. I was busy making music. I was making my full time living as a professional musician at that time. I even bought my house with the money I had made in touring. So I was already living my dream. Like I was living the musician dream. There are so few musicians that actually get to make a full-time living doing it. And I was doing it. I was living that dream. So as a favor on the side, just because I was kind of geeking out back in mid90s about making websites, as a favor to my friends that needed somewhere to sell their CD, I just made this little thing. But it was really meant to be a favor. So as it started growing, I felt like, “No, no, don’t grow. I’m busy. I’m trying to make music. I don’t want this little hobby to take over my life.” So, that’s what its DNA and that shaped its growth. It was this feeling of the reluctant business, like I didn’t want this to grow.

And, yeah, I wasn’t at a desperate place in my life. I was already making enough money doing music that I was able to buy a house. So I wasn’t broken starving. So I wasn’t desperate for money and – yeah, I think that’s why I got on this path of not wanting to – not wanting it to be bigger. But then even as it gotten bigger anyway, like it or not, there was still the opportunity to make it even bigger. It was the late 90s when I started it. So I could’ve done the whole IPO path and had shareholders and investors and all that stuff and made it ginormous.

But that’s when you just have to search inward and say, “Well” – kind of like you asked earlier, like why are you doing this? What’s the reason? Yeah, I just took some inward searching to realize that that wasn’t the lifestyle I wanted. Some people like Jeff Bisberg, Mark Zuckerberg or Richard Branson seem to want that lifestyle. But to me, I think I just prefer a simpler life. So back to your original question, when you quoted that line from the book about – to have something is the means, not the end. The funny thing is realizing that most people aren’t that way. All right?

Jenny:

Right.

Derek:

This took a long time to realize. Actually, I did a TED Talk about something similar called weird or just different where you realize that with almost anything, you could look at it from the opposite point of view and it would still be correct. Right? Like there are people that believe that Australia is at the top of the map and Canada is at the bottom. Well, because the earth is round, they’re also correct. It’s just an unusual way of looking at it. Right?

So the whole reason I’ve ever done anything has been for self-development. It’s always just a bit of a challenge to myself to see if I can do this thing, whether it’s writing a song or a book or doing a TED Talk or starting a company or programming. It’s all just this kind of self-development feeling of seeing if I can do it.

But it wasn’t until probably in my 30s that I realize that other people seem to do things for the sake of the thing, for the goals. That was just hard for me to understand. I think maybe it’s like one of those introvert, extrovert ways of seeing the world. To me, it’s all about the process. I don’t really care about the outcome that much. I just love the process of whatever I’m doing, even doing the dishes.

Jenny:

All right. That’s so fine about reading the book and how you program CD Baby from the start and found it fun. I remember teaching myself HTML and CSS by reading books on the elliptical machine at the gym. And so, I could resonate with how you went out and bought a PHP and a SQL book and started teaching yourself. And it was really fun to see that throughout building CD Baby for as long as possible, you kept doing much of the coding. And that’s such a fun choice to make. As CEO, you could’ve easily delegated and hired at the end of the day and only doing management or dealing with the big finance guys. And instead, you wanted to be there coding.

Derek:

Oh, exactly. You find what you love doing and you do that part, especially if it’s also the thing that is useful to others. Right? I do think there are two things to take into consideration, what do you love doing and what is useful to other people. So if what you love doing is playing videogames, well, that’s not very useful to other people. You probably cannot expect to do that. And also, get a rewarding career out of that. There might be three or four people who do, but most don’t.

So you’ve got to find the balance between those things. So luckily, programming fits that for me. It’s something I really love doing and seems to be useful to others.

Jenny:

Right. It’s interesting because this podcast is about pivoting specifically in one’s career or business. And as you were talking, I recalled I had a similar moment as you and that I’d become a manager at Google. I was 24 years old. And until that point, I thought, “Of course, I want to be the CEO of a company someday. That’s just what I should strive for.” And during that year, I really enjoyed coaching people. But there was a lot of pressure and rigmarole that came with it. I remember when I was 25 realizing, “I don’t want this. I don’t want to be working my way up through middle management and becoming a director or even CEO of some big huge company.” And that was what I think first sparked the thought that I could go out of my own and keep a relatively small business. And in a way on or my sort of introvert side, which is I want to think and read and do the work. And I actually don’t have these ambitions of having a huge team. But sometimes seeing online, even in the online space or books, there are so much talk about marketing and numbers. And it’s not always easy to pull back and say, “What’s the process? What’s the day-to-day experience that I really want and where I can do my best work to help others just as you said.”

Derek:

The thing about growing your list, and you said like this kind of pressure to have a big list. I often hear people say young entrepreneurs that are starting new business or have started new business will contact me and ask my advise about getting millions of users. And I have to ask those questions of are you doing this thing to serve others or to serve yourself? Because if you’re doing this to serve others, well then, you need to do what’s best for each individual person. Like are your clients asking you to grow your list? Probably not. That would be a pretty weird client who says, “The main thing I want you to do is to grow your list.” Now, each individual doesn’t care about the other people on your list. In fact, they’d rather get more of your personal attention for themselves. So grow your list is not something that my clients are requesting me to do. Therefore, I don’t.

Jenny:

I love that. It’s so true. That’s what I really love about the now page movement. Also is that you’re just kind of sharing, “Hey, here’s what I’m doing,” and I know it has become a huge movement. It caught on so quickly because it just truly seemed like, “Hey, I think this would be a helpful page for me to create.” And if you think so too, by all means do the same. And now, there’s hundreds of them. It’s been so cool to watch that unfold.

Derek:

Yeah. That was a really – oh, so we should tell the listeners what we’re talking about. And what Jenny is talking about is that about nine months ago, I put a new page on my website because people often ask me like, “Hey, so what are you working on now?” People who know me from years ago, whether CD Baby or my book or my TED Talks, or whatever, would email and say, “So, what’s up? What are you working on now? What’s going on with you? Where are you living these days? What are you doing?” And I would answer that question so many times that every time I’d get asked I’d kind of go, “Okay.” It takes me like five minutes to write out my answer to like, “What’s going on with me now? Okay. Well, here’s what I’m doing, I’m living in New Zealand, working on this and programming this thing. Here’s what I’m not doing. I’m not doing anymore public speaking. I’m not traveling as much anymore.”

And finally, after answering this question a few times, I thought, “I should just make this webpage that I can just point people to since this comes up a lot.” So I put it at Sivers.org/now. It was a nice short URL that was easy for me to remember. So if somebody was asking my email, I could just type out. Go to sive.rs/now. That’s what’s up with me.

But I also found it had this interesting side effect of making me ask myself what I’m working on now, and therefore what am I not working on now. Like I said, it with public speaking for speaking, like for years I did lots of public speaking at events and now I’m not. And I had to publicly admit that for myself like, “You know what? Yeah. I am not speaking at any events. That’s not something I want to do.”

Nine months ago, I put that page on my site, and I found it useful. But that was that, and nobody really mentioned it much. But then just one month ago, some guy sent me a tweet saying, “Hey, Derek, I liked your Now page idea, so I made one for myself.” His name was Gregory Brown, and he’s a Ruby programmer. And I checked it out. I said, “Cool.” And so, I re-tweeted him, and all I said was, “I wish everyone had a Now Page.” A few hours like eight people said, “That’s a great idea! I’m making one too. Here’s mine.” And then the next day I wrote a little blog post about it, just a bit that I mentioned already here. And within a couple of days, like another hundred or 200 people made one. And then a month later, I announced it again and a few hundred more people made one. And what I love is that each one of these are on their own domain. And I love that because I do think it’s a bit of a shame how the web has gotten so centralized on Facebook, Google, Twitter, etcetera. I really love the original decentralized web where everybody had their own space that they were in charge of instead of just putting everything in one shared – having all of our stuff owned by Facebook, or whatever.

So I love these, I don’t know, I forgot the number. It’s up to know 5 or 600 sites that have a now page. Each one is their own domain and…

Jenny:

Oh, cool.

Derek:

Yeah, and kind of celebrating the decentralization of the web.

Jenny:

Right. What I love about it, it’s the perfect antidote to the sometimes stressful question, “What’s next?” because instead it’s just right now. Here’s what I can know. I can know what I’m doing right now. And that’s enough and that’s okay and that’s something to celebrate and create a whole page on my website for. And then the inherent usefulness, I mean the second I saw your blog post and thought, “Oh my goodness, I need that ASAP,” because my about page is always about six months out of date. If not, a year.

Derek:

Right.

Jenny:

It just cannot keep up with the changes of and what I’m actually working on. So it’s been so fun to see the movement. And now, there’s even a Twitter account that will tweet out people of now pages, which is so cool.

Derek:

Yeah. Yeah, it’s been fun. It’s been pretty much my full-time job for the last month. It’s just doing now. So, anybody listening? If you go to nownownow.com, you’ll see that’s all about. And even that, it was like a domain that I had for a few years and I just wasn’t using. Years ago I actually made a little android app called Now, now, now. That was a totally different thing. It was more for that immediate kind of time tracking, like what am I doing at any given moment. I was trying to do the quantified sell thing where I would ask myself. I was like, “God, today just flew by. What was I actually doing?” So I made a little app where I would just at every single moment when I switched actions I would tap it to note what action I was now doing. And then later I could look how many minutes per day am I spending on programming versus traveling versus working out, or whatever. So, that was a different thing. But that’s why I have the domain name and Twitter account for Now, now, now. So, anyway.

Jenny:

You know an entrepreneur or an online nerd when you collect domains for fun as so many of us do. It might be hoard domains. And then it’s so fun when years later, after you’ve purchased you come out with the ‘uh-huh’ moment of what it can be used for.

Derek:

Oh, well, all right, Ms. Jenny. On that note, I’ve had this idea forever. Part of the reason –sorry, one thought at a time. Part of the reason I let myself stop what I was doing and work on Now, now, now for full-time for the last month is because it actually taps into something I’ve been wanting to do for years, which is to get to know the people in my contacts better, sort of just being a list of many contacts. I wanted to know them better and know where is everybody and what does everybody doing and what are your skillsets and maybe even finding a way to tag people as or first by location, Chicago or Prague, or whatever, and then by skillsets, what they have to offer. This person is really good at Photoshop. This person is a drummer, and then they’d be what people are looking for. So this person is looking for a photographer and that person is looking for a guitarist. And realizing that like it or not, I am already a connector. I’m not that type of personality that Malcolm Gladwell would’ve described in his tipping point book as a connector.

But I’ve become one just by circumstance. And so, for years, I’ve been wanting to do this thing that I was calling Karma List. You can find a blog post about it like five years ago on my site called like Karma List, wish list or something. And that’s one of those ideas that I never got around to doing but have always wanted to. And suddenly as people were giving me more information about themselves because of this Now page thing, I realized I was learning more about everybody, and it was really cool. So I’m kind of reinspired to maybe make this Karma list idea happen. It’s like an off-shoot of this Now, now, now thing.

Jenny:

I love it. I absolutely love it already. I posted my Now page and someone wrote through my blog and email me and said, “Derek Sivers is the genius, isn’t he?” and then he shared kind of what he’s doing. And I felt so grateful that here, the two of us share you as a connection. But then it created our own unique connection. I have this thing I called Brilliance Barter because I have a concept too I called Career Karma, which is seeds of generosity and don’t expect anything back, but so much good will follow. And my Brilliance Barter is in momentum and I bought this domain but correlated into momentum, which I called Take a Penny, Leave a Penny. So come to this forum. And if you did their karma list, Take a Penny, Leave a Penny. Ask for help and then throw out a seed of help somewhere. And just if we all did that, it’d be so great. There’s so much mutual sharing and connection happening as you’re already facilitating, like you said.

Derek:

Cool.

Jenny:

With the Now page movement, so it reminded me of your TED Talk which is how a movement happens. And one of the keys you say, hint, it takes two. So it was really interesting to hear how you first setup the page and then Cragery chimed in. And that that’s actually what became the catalyst.

Derek:

Yeah. I couldn’t believe that. But here, I’ve got this famous TED Talk. But I don’t actually see it in action so clearly so often. And here, it happened to me. And I didn’t make it happen, it just happened just the way I described in the talk. Just like you said, yeah, I was just – I had been doing this thing for a long time and it wasn’t until the first person invited me that everybody else started to. I just had to laugh at just how similar it was and…

Jenny:

That’s awesome. Well, keep us posted if you create karma list and we’ll all spread the word and jump on board as your beta testers. I also got a big smile when I read the dedication to Anything You Want. You dedicated to entirely to Seth Godin. You say, “This book only exists because of his encouragement.” What inspired you to write the book in the first place and then republished it a few years later?

Derek:

Well, Seth did. I mean that very literally that I never wanted to write a book. In fact, I think for years publishers had asked me to write a book. I said, “No, I’m not interested. That’s not one of my goals in life. I don’t care if I have a book in the world or not.” But then Seth Godin started to do publishing company and called me up and said, “I’m starting a publishing company and I want you to be my first author.” And so, I said, “Sure.” How could you say anything less than sure to that? So I said, “Okay.” I said, “What do you want me to write about?” He said, “I don’t know.” We talked about what it could be it. First he thought it might be a book about the music business. I said, “Nah, I don’t know. I’m feeling a little tired of that.” And he said, “Well, why don’t you maybe share what you’ve learned from ten years of starting, building and selling that company?” And I said, “Oh yeah. I could talk about that.” And I felt like it would be a nice way to wrap up all of my life lessons and put a little bow on it and call it done on to the next phase of my life.

So, that’s why I did it. Mostly just because of Seth asked. But then the other reason was…

Jenny:

That’s a good reason.

Derek:

Nice way to change chapters in your life, is to share what you learn in the previous one, which kind of helps cement the lessons for yourself too. We all know the feeling where you learn a life lesson, like Thursday at 2 o’clock. You have a little mini epiphany and you go, “Wow! I think I really learn something,” and you might share it with a friend. But a month or a year later, that feeling is lost, unless you’ve found a way to cement it. And I think that writing very public blog post that stay in the world on your side forever is one way of cementing these lessons and putting them into a book is another way very similar. But it really helps to share the lessons you’ve learned, especially if done in a very succinct and readable way. I find that to be very important, the fact that each one of these little lessons I learned, I found a way to make it into a short article, a short point because I read a lot of books. And I feel bad for the brilliant ideas I find on page 320 of a book because I know there’s so few people in the world that will ever get to page 320 in that book. And that idea will be lost for most people.

But if each idea would’ve been given its own little spotlight, it would spread better, last longer, be heard by more people. I try to take that approach.

Jenny:

Well, it really works. It’s so sticky and addictive and it’s really incredible to see how you’ve distilled these 40 lessons, even the graph. The graph in the opening page is the growth of CD Baby sales by month. It was so cool. And I don’t know if you found it cool looking at it upon reflection. Just to see your story out of glance, even just 10 years in one diagram.

Derek:

Sorry, I realize I didn’t finish answering your question about and you were citing to acknowledge it. So really, again, it was really all Seth. In only wrote the words inside. He came up with a title, the cover, the blurbs, the everything. I just wrote the essays inside. But that graph at the beginning, that was me. Because, yeah, for years I had looked at the bar graph of CD Baby sales and just went, “Wow!” It’s so wild to look at 10 years of my life in that chart. I remember when – you look at when it was four or five months old and it was tinny tiny little two pixel little blips down there. That felt big at that time. And then you look at year later and it’s like it’s still tiny little 25 pixels, and that felt big at that time. And then later you see it was just grew to this big ginormous thing. And I remember how awful that felt at that time. Oh, it just felt like too much. And it’s really interesting to see it in a graph. And I had the idea of taking the life lessons I had learned that are shared in the book.

I think the subtitle for the book is something like 40 lessons for a new kind of entrepreneur. So yeah, it’s broken into 40 little chapters each with a single point to single lesson in each. And then matching them up that graph saying like, “Here’s the point where I learned this. Here’s the point where I made that big mistake. Here’s the point where I learn this the hard way and lining them up to the graph. That was a fun way to see it visually.

Jenny:

It’s really powerful. And as you said that, just because the numbers grew did not mark the same point that your happiness was at its peak that actually there was a point where those two things crossed over.

Derek:

Yeah. I’m still fascinated with that. I would love to talk to anybody about this subject. So if you’re listening and you want to talk about this subject we’re about to talk about, please contact because I’m still – I feel like I haven’t gotten my answers to this. It’s about how different people have different set points for success and happiness or different levels of success where they feel happy. So think about Richard Branson. I’ve read I think all of his books that are out. He is totally cool with having 100 companies and being worth whatever tons of billions. That’s his set point where he feels happy. And I feel that there are – see, even on Tony Robins, for example, I remember long ago like whatever 25 years ago, he wrote this book called Awaken the Giant Within. And he wrote about buying a resort on Fiji.

And it’s funny to look back and realize that he was only like 25 or 26 when he wrote that book. And he was already speaking about having bought this resort in past tense. And I think about this now like, “Wow! At 25 his self-image was such that he saw himself as the kind of person that would own a resort in Fiji.” I still can’t imagine myself the kind of person that would own a resort in Fiji. That still feels like totally out of my realm of self-image of how I see myself the kind of thing I can imagine myself doing. So I’m really interested in how some people are very comfortable being a billionaire versus those like me that only want a million dollars. Again, I realize where I’m at in the spectrum that I’m around a lot of people. My friends here in New Zealand, most of them are broke artist that they would feel uncomfortable if they had $10,000 in their bank account.

So it’s all a – sorry, to be clear, I mean if they had as much as $10,000. Most of them only have enough for a few month’s rent. And if they had $10,000 at their bank account, that would feel weird. So a lot of my friends are like that. And I find this a very interesting subject, like where we have our set points of where we see our self. So, yeah, for me having a small company with a few people or maybe even up to like 15 people. I felt cool with that. That still felt like me. That felt all right. And I remember when CD Baby grew to the point where it had like 50 employees. I felt like this is kind of uncomfortable. I don’t like this. It’s getting too big and then it kept growing to 85 employees because it was just – even then, it was absolutely necessary. I wasn’t doing the typical investor growth thing where I was hiring ahead of need. It was those 85 people. Every single one was absolutely needed. And it just felt too much for me. So, yeah, I was much happier to walk away and go back to being just me again.

Jenny:

Oh, even your choice to sell the proceeds, to give the proceeds to the charitable trust, I think you’ve done such an incredible job of leading the way and having self-awareness around decoupling how much money you have in the bank with your work or your happiness and constantly realizing and reminding yourself and others that those do not guarantee the same thing that you can strive for money all you want. But it’s not necessarily going to be each individual’s packed to happiness. And it seems like you’ve continued defining that for yourself, and it was a really courageous move and bold. Maybe you don’t think so, but to give all the proceeds to charity is amazing.

Derek:

Thanks. I mean, yeah, it’s that same thing we were just talking about that CD Baby has already been profitable for years. I already had a few million dollars saved up. I’ve already paid off all of my debts. And when it became obvious that I was about to sell a company for $22 million, it just felt like I’m never going to use that ever. Why do I – I’m just going to give it all away, anyway. So it was really my lawyer that suggested that he said, “Look, if you’re serious, if you’re really going to give that all away anyway, well then, don’t be stupid. Don’t receive the $22 million, pay $7 million in tax and only have 15 million left to give away.” He said, “If you’re really serious about giving it all away, we can structure it in such a such way where the entire $22 million gets given away.” I said, “Yeah, let’s do that.”

So, it’s something I still wrestle with though is it’s hard to break the habit of doing things for money. We spend so much of our lives trying to make money and it’s hard to stop sometimes when it’s just irrational. So I still wrestle with it, even just like a couple of weeks ago. Somebody offered to pay me, I don’t know, I think like $20,000 plus all expenses to come out to some Santiago, Chile to speak at this business conference. And even then, it was like, “Just give a 30-minute speech.” That’s all we ask and it was really hard to look at that and say no because I’m working on other things. Going to Santiago is not something I’m looking to do right now.

So, it’s hard to say no to money.

Jenny:

Absolutely. On the subject of I’m glad you bribe your lawyer, there’s an interesting dichotomy in your book around being scrappy, ditch business plans, you don’t need it, terms and conditions, I mean you’re not saying be reckless but you’re saying question your assumptions about how much of that infrastructure you really need versus the chapter on the $3.3 million mistake. And I don’t want to give it away because that was such a powerful story to read in the book. But let’s just say there was a $3.3 million mistake. So, how can people strike the balance between these two things?

Derek:

Okay. The$ 3.3 million mistake was because I didn’t read the contract I was signing. So let’s just give that as the context. Okay?

Jenny:

Yeah.

Derek:

For the next point. So there’s a programming phrase called, “You aren’t going to need it,” and it’s often abbreviated to the acronym of YAGNI, you aren’t going to need it. And programmers used this phrase often to avoid adding features that you think you might need in the future. Like, well, we might as well allow for people to have multiple email addresses per account because they might need that. Let’s give the ability for people to download the file they’ve paid for later instead of immediately. So it’s a wise bit of a programming advice to keep telling yourself you aren’t going to need it for that future stuff and only focus on what you absolutely need right now. And then programming wise, you can always add in that other stuff later when you need it, when lots of your clients are saying, “We need multiple email addresses per account, then you can say, “Okay, now we need it. But until then.”

So on a personal level, you can use the same phrase, you aren’t going to need it, for your personal life. Say, like camping for example. You all know in the camping metaphor that you can’t bring everything with you. You can’t afford to bring everything you think you might need. You have to make some decisions when you’re packing your bag. What’s absolutely going to be necessary versus probably not and you don’t bring the probably not stuff. And same with how you fill your house with stuff, do you really need to buy 16 plates instead of 4? People often do this thing, like, “Well, what if I have guests over?” Maybe it’s better to wait until you’re actually having a party to buy 16 plates. Until then, two to four probably enough. For design, people often do this silly, goofy page bloating things like this sliding JavaScript thing that makes the text fade in slowly.

Jenny:

All flash websites from…

Derek:

Right. Or even the very common things that most people don’t even question. Like most people with a blog have that stupid column on the right hand side with a list of all past archives grouped by month. But come on, how many people are demanding to know what you wrote in March of 2011? You aren’t going to need it. You can leave that off. You don’t need that. Even though it came by default in WordPress, go find a way to delete that from the template because you don’t need that. So, that was all my little mini rant about why I still think it’s crucial to question these things, like putting terms and conditions and a privacy policy on your website or all this stuff. Or even when you start a business and especially when you start to have employees, you’re going to be contacted by a bunch of consultants that say, “You really need to talk about your employees and make plan. You need to have the,” I don’t know, there are a lot of consultants that come at you trying to make you think that you need this stuff. But you don’t need it. So I still think it’s crucial to say no to everything possible because just use the phrase, ‘you aren’t going to need it.’

Jenny:

I love that.

Derek:

Just use that as the base assumption and wait till you actually need it. Then, yes, for the few things that you do accept and you decide that you need, make sure you read the fine print.

Jenny:

Yes! Very good advice. I agree. I feel like when it comes to career pivots of just something I’m studying, looking too far ahead is kind of pointless because we can’t predict the future. So whether it’s – what we’ve talked about with money or features, if you’re not going to need it, you just don’t know right now. Or the dinner party that you mentioned that actually by looking at where you are right now – and it’s not being too shortsighted. Of course, we want to plan for some growth. But that starting with the fundamentals and the basics and letting – I think that’s you said at the very beginning that you love change, which not everyone does, even though it’s the only constant we have in our life. And that I think part of being agile to change and career change is assessing your need in the moment and kind of planning around that and not getting too wrapped up in the future.

Derek:

Yeah.

Jenny:

How can people be more agile with change? I know it’s something that my come more naturally to you than others.

Derek:

I think it at first, just have a confidence in knowing that everything is going to be okay. I think that it’s scary for a lot of people. I think of these worst-case scenarios. Yeah. I think confidence really helps in change. And confidence comes from two things. One, it’s needing as little as possible to make yourself happy. Like for example, if you know that all you really need to be happy is, say, a good book and a warm enough environment where you’re not freezing and some food, or something like that. Well then, you’re going to be okay no matter what. You could even get fired and lose all your money, or whatever. And it’s like as long as you’ve just got a basic – these basics, you’re going to be happy, and anything above that is just extra.

Jenny:

That is true.

Derek:

That’s a good starting point to remember how little you actually need to be happy and then define what it is. Say, you found from experience that you just can’t be happy without a view, that’s good to know. Make sure that no matter how cheaply you’re living, maybe it helps to move out to the middle of Oklahoma, find a cheap place, as long as it has a view. You don’t have to be in Manhattan to be happy. But you do need a view. Know what your priorities are.

But the other thing that most people don’t talk about is the importance of pessimism. I hear from people a lot, whether friends or strangers emailing me. This feeling like somebody saying, “I’m really scared about this thing I’m doing” or “I’m scared about this new project,” or “I’m scared to launch this.” How do I get over that fear? That’s the big question. Like, how do I stop being scared? And my advice is always to not stop being scared, but to honor those fears because like the camping metaphor, we said earlier, if say you felt like, “I’m going to go spend three days in the woods. But I’m scared. I might starve. I’m scared I might freeze. I’m scared I might get lost.” Well, those are very valid concerns, and you should not try to get over your fears in that case. You should make sure that you bring plenty of food and make sure that you bring a warm sleeping bag and warm clothes and you should bring some kind of compass or GPS so that you don’t get lost.

Yeah, prepare for those things that you’re scared of. Don’t get over your fears. So I think the same in life situations that you think about what you’re scared of you address those things. Like, “I’m scared nobody will sign up for my new service I’m launching next week.” Well, it’s a valid concern. How do we address that and tackle that one and then – once you’ve packed your sleeping bag and plenty of food and a GPS, you’re no longer scared because you’ve addressed your fears. So whether it’s a career change or launching a new project or getting at the guts to quit your job or whatever, I think it’s very worth addressing your fears.

In fact, as a little PS to that point, Daniel Kahneman is the name of the Nobel Prize winning Behavioral Economist that wrote the book Thinking, Fast and Slow. Very widely renowned in this industry. I think I read a dozen books before he’s came out with other people referencing him and quoting him and calling him like the master in his field. So when his Thinking, Fast and Slow book came out, I was thrilled. And afterwards, just in fact, a couple of months ago, somebody asked him one of those petite, tiny, little one sentence interview where they ask a bunch of different people one sentence questions. And the one sentence question was, what do you think is the biggest impediment to most people’s happiness or success, or something like that. And he said overconfidence. He said, “In all my decades of studying psychology and people,” he said, “I think most people’s fatal flaw is overconfidence.” I thought that was really interesting.

Jenny:

That is fascinating. That’s fascinating. That reminds me of your line from the book. You say, “I’m a student, not a guru.” And that in a way seems also like a counter to overconfidence. You’re saying, “I don’t have all the answers. I’m here to learn just like everybody else.”

Derek:

Yeah. It’s important to be in that mindset. I think in fact that’s part of why I’m out of the music business right now is because I noticed I was starting to get this know-it-all guru kind of mentality. Like, yeah, yeah, yeah, I’ve seen thousands of careers flourished. I’m a big shot in the big music business. I’ll tell you what’s what. And I would go up of these panels of conferences and answer everybody’s questions and felt like such a know-it-all. And, yeah, shortly before I sold CD Baby, I just realized, “Yeah, I think I’ve got my head at my ass a bit.” I’ve been giving the same answers to these questions for eight to ten years now.” And times have changed and I’m acting like they haven’t.

So I’m going to quit thinking I know what I’m talking about. I’m just going to assume that I don’t for a while and – I think that’s just a better mindset to get into – to get a fresh perspective on things, especially in an industry that’s changing a lot. When you see those websites where people are still making websites, like it’s 2001, like, “Oh no don’t. No, no, no. Time has change. Please stop it. I know that you learned how to make a website in 2001. But that’s not how you do it anymore.”

Jenny:

Right. Well, there’s an interesting paradox too, which is – and I think I’m getting really fascinated by the idea of paradoxes in our everyday existence. And there’s another one that, yes, share what you’ve learned. You have value, your stories are fascinating, your TED Talks had millions of views and maintain humility and a sense of willingness to be wrong and to continue exploring. And it sounds like just kind of joggling those two things that honestly we all could do that no matter what level we reach.

Derek:

It helps to not need to look like an expert. Right? I understand there are some people, whether they are realtors or consultants, or whatever, that there are some people that they need to look like an expert. It’s very important for their career that they look like they know what they’re talking about. And so, I feel lucky that I’m not in that position. I don’t care if I look like the biggest idiot in the world. I’m not looking to make a living off of my expertise in something.

Jenny:

It’s like you go minimalism, like you talked about minimalism.

Derek:

Right. Yeah.

Jenny:

It’s awesome.

Derek:

But I don’t need to make it sound like we all need to go out there calling ourselves idiots. There are some career strategies where you need to appear to be an expert that you know what you’re talking about. Like all those futurist. God, can you imagine what it would be like? A professional futurist where you have to say, “Yeah, I know what the future holds.” You have to go out there like a confident motherfucker say that kind of stuff wholeheartedly like, “Yup, I’m going to tell you what is going to happen in the future.” Yeah, those people need to show expertise and show confidence. They can’t shrug and say, “Well, we don’t know,” because then that’s their career.

Jenny:

I’ve always thought that about people who run for president. It’s like a special type of person that think, “Yup, I have everything it takes to run this country,” and it’s just amazing. When I say this country, I mean the States. But same principle anywhere, really. It’s amazing to me.

So, Derek, thank you. This has been absolutely fantastic to talk to you and hear your very wise words. Last question, what are you most excited about in the coming year?

Derek:

Really, just finishing my programming projects I’ve already started. I think life goes through different phases of times when we’re lifting our head up to take in new ideas and new input. And then times when we just need to put our head down and just do the work and finish what we started. And right now, I’m deeply in a head down phase of just shutting out everything, saying no to everything, putting myself on to the remote island of New Zealand and shunning everybody and just finishing what I’ve started a few years ago. So, that’s what I’m looking forward to most.

Jenny:

That’s awesome. Well, thank you for saying yes to this. And please let us know. I speak on behalf – at least of many of my readers and listeners who I like to bring generous people together and people who are smart and interested and helping others. So if there’s anything that any of us can do to be helpful as you wrap up or test your projects, let us know.

Derek:

Thanks. Well, actually, vice versa, really. Go to sive.rs, my website. And at the very bottom, you’ll see my email address in a big font. So drop me an email, introduce yourself.