22: Success on Your Own Terms with Derek Sivers

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Hi, I'm Jenny Blake, your host of the Pivot Podcast and author of the book Turn what's Working for your 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 and 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 for those of you Myers Briggs nerds. A minimalist and a California native now living in New Zealand, Singapore and Belgium. I reached out to Derek after reading Anything youg Want, which I read when it first came out in 2011 with Seth Godin's Domino Project team and Derek just republished with Portfolio Penguins. 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 friends.

So Derek, thank you so much for being here.

Thanks 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.

I did that with the book Geek in Japan. I'd 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 the book 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.

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

Japan. Okay.

No, you don't say.

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

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 it 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 for 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. And 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 afterward in such an authentic way. There's 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 you already have a plan for what's next or how did you navigate those first years afterward?

Hmm. 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 10 years, I'm no longer Derekdbaby.com Whoa. Like, I slept for like 10 hours that night, which I never do. I'm usually the kind of five hours a night kind of sleeper. I slept so long that night with just this 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. I was like, ooh, 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. And that was muck work. And you can even see the. I have to laugh when I look at the who is on the domain name. That. That day, literally the day after selling CD Baby, I registered the domain name for my next company and immediately started programming all day long and built the database and started to like, spell out everything the way it was going to work for this new business. And I think I even 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 into 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, dent in the universe, whatever you want to call it, we all have the different things that we're.

Out 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 would just be doing the same old process without really making a real change. So after a little soul searching, I decided to pause that. 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. Just 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 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.

Right.

Ideally, that should go without saying, but, you know, 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, doesn't matter what, you know, 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.

Climate. 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. In other situations where it would be wise to stop trying to make money and just.

Follow your dreams instead.

Well, 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 costs. 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 pulled back from that pressure to get outside funding or grow at all costs?

Sure.

The DNA of something matters, right? The DNA is what decides if something's going to be a pine tree or a penguin. So.

The DNA of CD baby was just a favor 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 the time. I even bought my house with the money I had made touring. So I was already living my dream like I was living the musician dream. There's 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, you know, mid-90s 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 to this little hobby to take over my life. So that was its DNA and that shaped its growth 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, you know, I wasn't broke and starving, so I wasn't desperate for money. And.

Yeah, I think that's why I got on this path of not wanting it to be bigger. But then even as it got 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 have done the Whole IPO path, you know, 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? But yeah, it just took some inward searching to realize that that wasn't the lifestyle I wanted. Some people like Jeff Bezos or 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. Right?

Right.

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. And well, because the earth is round, like 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 realized 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 that 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. You know, even doing the dishes.

Right. That's what was so fun about reading the book and how you programmed 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 just such a fun choice to make. As CEO, you could have easily delegated and hired and at the end of the day been only doing management or dealing with big finance guys. And instead you wanted to be there coding.

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. Like, I do think there are two things to take into consideration, like what do you love doing and what is useful to other people. So if you, if what you love doing is playing video games, well, you know, that's not very useful to other people. You probably cannot expect to do that and also.

Get a rewarding career out of that. You know, there might be three or four people who do, but most don't.

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

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 in that I had become a manager at Google. I was 24 years old, and up till 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. And 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 on my own and keep a relatively small business and in a way honor 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's 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.

Well, you know, 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 a new business or have started a new business will contact me and ask my advice about getting millions of users. And I have to ask this question 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, you know, the main thing I want you to do is to grow your list. No, the. 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.

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 this 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.

Yeah, that was a really. Oh, so we should tell the listeners what we're talking about. So what Jenny's 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 from Ced 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 you doing? And I would answer that question so many times that every time I'd get asked it, 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 any more 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 a webpage that I can just point people to, since this comes up a lot.

So I put it@sivers.org now it was a nice short URL that was easy for me to remember. So if somebody was asking by email, I could just type out, go to sivers.org 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 with public speaking, for example, like, for years I did lots of public speaking at events, and now I'm not. And I had to kind of publicly admit that to myself. Like, you know what? Yeah, I am not speaking at any events. That's not something I want to do.

So 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 retweeted 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 the bit that I mentioned already here. And within a couple 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, etc. 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, you know, having all of our stuff owned by Facebook or whatever. So I love that these, I don't know, I forget the number. It's up to now five or six hundred sites that have a now page. Each one is their own domain.

Yeah, kind of celebrating the.

Decentralization of the web, 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 useful. I mean, the second I saw your blog post, I thought, oh, my goodness, I need that ASAP. Because my about page is always about 6 months out of date, if not a year. I just cannot keep up with the changes. 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's now pages, which is so cool.

Yeah, yeah, it's been fun. It's been pretty much my full time job for the last month is just doing.

Now. So anybody listening? If you go to now now now.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 self thing where I would ask myself like, God, what 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 had the domain name and Twitter account for Now Now Now.

Anyway, you know you're an entrepreneur or an online.

Nerd when you collect domains for fun, as so many of us do, we hoard domains. And then it's so fun when years later, after you've purchased, you come up with the aha moment of what it can be used for.

Oh well, all right, Miss Jenny, on that note, I have had this idea forever. Part of the reason, 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. Instead 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 skill sets? And maybe even finding a way to tag people as well. First by location, you know, Chicago or Prague or whatever, and then by skill sets, what they have to offer. This person is really good at Photoshop. This person is a drummer. And then maybe 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 have 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 5 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 re inspired to maybe make this Karma List idea happen as like an offshoot of this now, now, now thing.

I love it. I absolutely love it already. I posted my now page and someone wrote through my blog an email, and they said, derek Sivers is a 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 call Brilliant Sparter because I have a concept too I call career Karma, which is plant seeds of generosity and don't expect anything back. But so much good will follow. And my brilliance partner is in momentum. And I bought this domain but parlayed it into momentum, which I call Take a penny, leave a penny. So come to this forum and if you did your Karma List, take a penny, leave a penny, you know, ask for help, and then throw out a seed of help somewhere. And just if we all did that and it'd be so great, there'd just be so much mutual sharing and connection happening as you're already facilitating, like you said.

Cool 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 set up the page and then Gregory chimed in and that that's actually what became the catalyst.

Yeah, I couldn't believe that here, you know, 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. It just, 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 imitated me that everybody else started too. I just had to laugh at how similar it was.

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 youg Want. You dedicate it 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 republish it a few years later?

Well, Seth did. I mean, 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 and I said, no, just 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 a new 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. And we talked about what it could be. At first he thought it might be a book about the music business. I said, I don't know, I'm feeling a little tired of that. And he said, well, why don't we maybe share what you've learned from 10 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, you know, onto the next phase of my life. So that's why I did it. Mostly just because Seth asked. But then the other reason was that's a good reason. A nice way to, to change chapters in your life is to share what you learned 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 a Thursday at 2 o', clock, you have a little mini epiphany and you go, wow, you know, I think I really learned 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. You know, I think that writing very public blog posts that stay in the world on your site forever is one way of cementing these lessons, and then putting them into a book is another way. Very similar, but I think 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 have been given its own little spotlight, it would spread better, last longer, be heard by more people. I try to take that approach.

Well, it really works. The book is 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 pages, 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 at a glance, Even just this 10 years in one diagram, most of that.

Sorry, I realized I didn't finish answering your question about deciding to and all that stuff. So really, again, it was really all Seth. I only wrote the words inside. He came up with the title, the COVID 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 kind of 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. Like, I remember when, you know, you look at when it was only four or five months old and those teeny, tiny, little, you know, two pixel little blips down there that felt big at the time. And then you look a year later and it's like, still, you know, tiny little 25 pixels. And that felt big at the time. And then later, you see, it just grew to this big ginormous thing. And I remember how awful that felt at the time, how it just felt like too much. And it's really interesting to see it in a graph. And then 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, a single lesson in each, and then matching them up to 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 learned this the hard way and lining them up to the graph. That was a fun way to see it. Visually.

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.

Yeah, I'm still fascinated with that. Like, I, 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, I'm still. I feel like I haven't gotten my answers to this, which. 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 and he's totally cool with having 100 companies and being worth whatever, tens of billions. That's his set point where he feels happy. And I feel that there are, See even Tony Robbins, 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.

Wow.

And I think about, about this now, like, wow. Like at 25, his self image was such that he saw himself as the kind of person that would own a resort in Fiji. Like, I still can't imagine myself as the kind of person that would own a resort in Fiji. That still feels like totally out of my realm of self image, 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, you know, those like me that only want a million dollars. But it's 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, you know, broke artists that they would feel uncomfortable if they had $10,000 in their bank account, you know, so. 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 months rent. And if they had 10,000 in their bank account, that would feel weird. So a lot of my friends are like that. And I don't know, I find this a very interesting subject, like where we have our set Points of where we see ourselves. So, yeah, for me, having a small company with a few people, maybe even up to like 15 people, I felt cool with that. Like, I felt like 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.

Well, 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 worth 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 path to happiness. And it seems like you've continued defining that for yourself. And that was a really courageous move and bold. Maybe you don't think so, but to give away all the proceeds to charity, it's amazing.

Thanks. I mean, yeah, it's. It's that same thing we were just talking about. That CD Baby had already been profitable for years. I already had a few million dollars saved up. I'd 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 am I? Why do I? What am I? I'm just going to give it all away anyway. So it was really my lawyer that suggested it. He said, look, if you're serious, if you're really going to give that all away anyway, well, then don't be stupid. Like, 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 I don't know. 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 this. Even just like a couple weeks ago, somebody offered to pay me, I don't know, I think like $20,000 plus all expenses to come out to 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 just am 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.

Absolutely. On the subject of, I'm glad you brought up 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?

Okay, well, the 3.3 million dollar mistake was because I didn't read the contract I was signing. So we'll just give that as the context. Okay, yeah. For the next point. So there's a programming phrase called you aren't gonna need it, and it's often abbreviated to the acronym of Y A G N I, you aren't gonna need it. And programmers use this pH 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. Or 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 not until then. So on a personal level, you can use this 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. You don't bring the probably not stuff.

Same with how you fill your house with stuff. You know, 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 are actually having a party to buy 16 plates until then, two to four are probably enough.

For design. You know, people often do these silly foofy page bloating things like this sliding JavaScript thing that makes the text fade in slowly.

All Blush websites from the 90s, 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 know, that's. That's. 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, you know, 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, you know, the. 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 employee, something planning. You know, you need to have the. I don't know. Just 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.

I love that.

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.

Yes, very good advice. I agree. I feel like when it comes to career pivots, which is 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 short sighted, of course we want to plan for some growth, but that starting with the fundamentals and the basics and then 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 lives. 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.

Yeah.

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

Hmm. I think it first has to have a confidence in knowing that, that everything's going to be okay. I think that's. It's scary for a lot of people. They think of these worst case scenarios.

Yeah. So I think confidence really helps in change. And confidence comes from two things.

From one, it's needing as little as possible to make yourself happy. You know, then 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 in 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. So that that's a good starting point to remember how little you actually need to be happy and then to define what it is. You know, like say you've found from experience that you just can't be happy without a view. That's good to know. Make sure that you know no matter how cheaply you're living. Maybe it helps to move out to the middle of Oklahoma, find a cheap place, but 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 get a. 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 thought, 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 that you don't get lost. Like, 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 and you address those things right. Like, I'm scared nobody will sign up for my new service I'm launching next week. Well, that's a valid concern. How do we address that?

Tackle that one. And then, you know, 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 up the guts to quit your job or whatever, I think it's very worth addressing your fears. In fact, As a little P.S. to that point.

Daniel Kahneman is the name of the Nobel Prize winning behavioral economic.

Economist that wrote the book Thinking Fast and Slow. Very widely renowned in his industry. I think I read a dozen books before his 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 months ago, somebody asked him one of those pithy, tiny little one sentence interviews 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 then I think most people's fatal flaw is overconfidence. I thought that was really interesting.

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.

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. I've seen thousands of careers flourish. I'm a big shot in the music business. I'll tell you what's what. And I would go up on these panels at college 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 up my ass a bit. Like, I've been giving the same answers to these questions for 8 to 10 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 and 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. Oh, no, don't. No, no, no. Times have changed. Please stop it. I know that you learned how to make a website in 2001, but that's not how you do it anymore, you know?

Right, 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 have had millions of views and maintain a humility and a sense of willingness to be wrong and continue exploring. It sounds like just kind of juggling those two things. So honestly, we all could do that no matter what level we reached.

It helps to not.

Need to look like an expert. Right. Like, 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. I don't care if I look like the biggest idiot in the world. Like, I don't. I'm not looking to make a living off of my expertise in something so ego minimalism.

Like you talked about.

But I don't mean to make it sound like we all need to go out there calling ourselves idiots. You know, there are some career strategies where. No, you, you do need to appear.

To be an expert that you know what you're talking about. Like all those futurists. God, can you imagine what it'd be like, a professional futurist, where you have to say, yep, I know what the future holds. You have to go out there like a confident motherfucker, say that kind of stuff wholeheartedly, like, yep, I'm going to tell you what is going to happen in the future. That's. 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.

I've always thought that about people who run for president. It's like a special type of person to think, yep, I have everything it takes to run this country and it's just amazing. Well, 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?

Really Just finishing my programming projects have 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 onto the remote island of New Zealand and kind of shunning everybody and just finishing what I've started a few years ago. So that's what I'm looking forward to most.

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 in helping others. So if there's anything that any of us can do to be helpful as you wrap up or test your project, let us know.

Well, actually vice versa, really. Go to sivers.org, my website, and at the very bottom you'll see my email address in a big font. So drop me an email, introduce yourself.

Great. Thank you so much.

I mean that to anyone. Awesome.

Yeah, that's for anyone listening. Awesome. Thank you so much, Derek. And we'll put all these links and books, including the one on Japan in the show Notes. So thank you again for being here and thanks everyone for listening.

Thanks Jenny.

Thanks so much for listening to this episode of the Pivot podcast. To learn more and get in touch with visit Jennyblake Me where I blog about systems at the intersection of mind, body and business. Or find me on Twitter ennyblake. And remember, build first, then your courage will follow. Hasn't it always.