Derek Sivers, so excited to have you here. Please tell our viewers who you are, what you’re up to these days, and where they could connect with you to learn more.
Where am I? I’m at home in Oxford, England. Who am I? I was a professional musician for 15 years. Way back in 1997, I was selling my CD on my band’s website when all of my musician friends said, “Hey dude, could you sell my music through your website too?”
I said, “Yes,” and I accidentally started the largest seller of independent music on the web. I called it CD Baby. I did it for 10 years until I felt done with it and sold the company in 2008, gave all the money to charity, and wrote a book about it for our mutual friend Seth Godin called Anything You Want, and that’s my book about my tale of how I built, grew, and sold the company.
In the last few years, I’ve been pop-philosopher at large. Asking myself questions, answering them, and questioning my answers. That brings us up to this moment.
How about a quick website or blog or social media?
sive.rs is my website where I keep everything.
Yes, and a brilliant blog. I love how clean it is, I must say that. Just super clean and easy and full of juicy goodness.
I actually know you through CD Baby. I was one of the early clients, and you helped me make some money as a musician way back in the day.
I read your book about that experience and what I love about that whole journey is the beginning. It’s this wacky collision of serendipitous moments that lead you from being a musician, hocking his CD on his own site, to developing this huge entity that is making it possible for millions of other musicians to do the same and augment their income as working musicians.
How has that serendipity continued to play since you left CD Baby?
I don’t know about continued, but there might be a lesson for your listeners in that moment because here we are talking on Creative on Purpose. You can be creative on purpose, but I think success can be an accident. It’s a little bit like lottery tickets, right? You never know what thing you do is going to hit.
For years leading up to that, I ran a record label and a booking agency. I had a recording studio. I put out my own music. I did lots of various things. Then this one tiny little side project that was one of the lesser things I did is the thing that just took off.
It felt a little bit like when I’ve read interviews with successful musicians. A lot of them say that the song that became their biggest hit was a song that they almost didn’t record and just threw away because it was just so silly or stupid. It was added at the last minute as an afterthought. It was a little joke song they used to sing on the bus, so they recorded it and boom. That becomes the big hit.
It’s so weird that you can pour your heart and soul into something that can have all kinds of meaning to you. You can say, “This is it. I’ve got a feeling! This is the powerful message I need to deliver to the world!” But then the world doesn’t care about that. This stupid little throwaway thing that doesn’t mean anything to you can become your big success.
So that actually happened later. I skipped a few steps when I told my initial “Hello” story. After selling CD Baby, I decided that I wanted to be a TED speaker. This was back in 2008 when I was into TED. I’m not anymore. But at the time I was into it. I was like, “Yeah, that’s what I want to do. I want to be invited to be a speaker at the TED conference, not TEDx. The real big main stage, TED. I set that as a mission.
I pitched three different talk ideas to them. I pitched the one that I really, really wanted to do. As a backup, I pitched the one that I also kind of wanted to do. Then they had a space on the forum where you’re supposed to fill in three ideas. For the third one, I said, ”I don’t know. There’s a Newsweek article I read this morning that was kind of interesting.“ I wrote that as the third one.
Of course, that’s the one they chose. So now I’m up on stage at the TED conference speaking about some article that I read moments before filling out a form, and that’s the one that was chosen to deliver on stage.
So for your listeners, I just want to re-emphasize the fact that people often like to make it look like their success was some kind of deliberate plan, but so often it’s just the random roll of fate.
I really appreciate and love that you highlighted that. One of the things I found is that it’s important for me to set an intention and to be aiming at something, but not to be attached to the outcome that I’m pointing at. Because that’s not really up to me.
In a conversation with Michael Bungay Stanier on this podcast, he talked about this. It’s important to set your aim. It’s important to remember that you’re rarely going to end up where you aimed at. You’ll probably end up somewhere still that’s really great because you are paying attention, taking advantage of the opportunities, and handling the obstacles amidst all these things that you could not possibly have known about until you started stepping into the possibility that you set forth for yourself.
One of the most interesting ideas I’ve ever heard about this topic is that goals are not meant to shape the future. We think of goals as some kind of tool to shape the future – not to get new agey, but the future doesn’t exist. The future is a term that we call our imagination. When we picture something in the future, we call that the future. In reality, the future doesn’t exist.
All we really have is the present moment. A good goal can’t shape the future because the future doesn’t exist. A good goal is something that changes your actions in the present moment. If a goal makes you jump out of your chair and get to work, it’s a good goal. That’s all it’s really meant to do.
What happens in the future? Who knows? But if you decide this is where I’m headed, if that changes your actions for the better in the present moment, it’s a good goal. Whether that was one of those giant goals like, ”I’m going to be a billionaire!“ Or if it’s just something like, ”I want to finish this song tonight.“
Whatever goal it is, it doesn’t necessarily shape the future. It just has to shape your present actions.
That reminds me of the Cicero’s Archer metaphor. He’s talking about Stoic philosophy. He says the archer must set his aim. He must aim at the bullseye. He must also accept that whether or not the arrow hits the bull’s eye once he releases the arrow is really not up to him. So many things can happen that may cause the arrow to go somewhere else. So his duty is in the present moment to put forth his best effort, and that the effort is the actual reward, not the achievement or failure of hitting the target.
I love that we use the word ”release“ when we talk about how we released an album and released a book. Yep! it’s released. It’s gone. You let go of it. We don’t really say I released an article on my blog. We say posted. It’s a shame. We should say released. I released an idea to the world [laughter].
What are some habits, ideas, or ways of being that have helped you? I get the sense from everything I’ve read of yours that through your whole journey, you’ve really experienced a pretty consistent state of feeling like you were flourishing and thriving. That what you were doing mattered. It had an impact. That it was serving others.
What are some of the habits or ways of being in the world that have helped you?
Sometimes I do things because I really, really, really want to do it and I really don’t care what anybody else thinks.
When you do that, you have to let go of the idea of financial reward or even social reward for doing that. That’s the classic starving artist problem. When somebody does something that has great value to them but not value to the world. There’s a separation.
If you want the world to reward you, then you have to do things that are valuable to the world. You could either define that as taking a job that pays well, or on the creative side, think of it as just getting the world’s feedback for what they want from you.
As soon as I sold CD Baby in 2008 and I launched my personal sive.rs site, I posted on the home page and said, ”Here are the six new projects I’m going to be working on in the upcoming year. Let me know if you’re interested in any of them.“
I had headline descriptions for each one of them. Four of them had no interest. One had a little interest and for one of the six, people went, ”Oh my god! Yes, I need that. Dude! Please let me be the first customer. Can I use it now? Can I try it now?“ There was one that was clearly the thing that everybody wanted from me. So I let go of the other five and I just did that one.
I do that a lot in life. I’m in constant direct communication with my audience, and that helps a lot. I listen to what people want from me and then I can decide if I’m looking for social or monetary rewards, then this is what I should be doing. Sometimes I hear what the world wants from me and I decide no, there’s something I really feel like doing. Even if the world doesn’t want it from me, I still feel like doing this. So that’s the mindset.
The artists that I know – musicians and otherwise, anybody that’s engaged in some sort of meaningful enterprise that intends to make the world a better place, or to enhance the lives of others – isn’t just serving their own selfish needs, wants, dreams. and desires. They’re actually paying attention to what the person in front of them needs, wants, dreams and desires, and trying to generously help that person get from where they are to where they want to go.
Right. I often think of it as being a public servant. I think of what I’m doing as public service because if it wasn’t, then I don’t have to release anything [laughter].
If I was just doing this for myself only, then I could just stay in the comfort of my room and just create all day long. I don’t have to release anything. I don’t have to get any nasty comments. I don’t have to get any spam. I don’t have to put my ass on the public stage.
Anytime you’re putting yourself out there publicly, I really do think it’s generosity.
Yeah, and courage. We were talking a little bit about purpose before we arrived here at the page. I’d love to go ahead and dive into that a little bit. You were talking about playing with your son and how that compares to the work that you do, and having that sense of play.
I find that approaching the hard stuff – the getting up in front of people, the ”here, I made this for you, I hope you like it“ – I find that if I approach that with that childlike sense of wonder, awe, curiosity, the lack of ego, it’s easier. It’s usually the self-inflicted anxiety that prevents you from standing up to speak your truth and share your talent. How does that land?
You also have some really interesting things to say about where purpose comes from, or where purpose lies in the work that we’re doing.
OK, two very different subjects. Let’s talk about the new one you just said. I’m not saying this is a good thing, and maybe it’s not, but I make a huge difference between private and public. My private creation, when I’m sitting here with my fingers flying and making things, that’s just like playing. That’s just completely selfless. I cease to exist. I’m just existing through the work. Playing with ideas, doing stuff, making ideas happen.
When it comes time to release something publicly, I put a very, very strong filter on what I put out there. Maybe it’s my minimalist tendency. I don’t want to put junk out into the world. My mailing list is about half a million people, so if I’m emailing half a million people saying, ”Check this out,“ I have to feel through and through that this isn’t going to waste a single minute of anybody’s time.
That’s why anything I post on my site, I edit the hell out of it. I found out recently that my average length of an article I post is 19 sentences but of course I have hundreds of sentences in my private version. I edit, edit, edit, edit until I can’t get rid of any more sentences. I tried, but this is as short as I can possibly make it and I’ve chopped out every unnecessary word and now I put it out into the public.
So no, I wouldn’t say that the public creation is child-like. It’s actually very, very mature [laughter]. But the private creation is child-like. It’s more play-like. Two different mindsets. Does that make sense?
Yeah, it does and I share that. I’m standing sitting here with less is more tattooed on my bookshelf because it seems to be the thing that I’ve been put on this planet to learn. I resisted mightily up until very recently.
Like you, I haven’t done sentence counts, but I try to keep my blog post at a two-minute read. I want to make one point and make it as succinctly as possible so that somebody can take that idea and do something with it.
At the same time, I’m thinking about the beginning of my journey with Creative on Purpose and where it actually existed as a different brand. I didn’t really have a clear idea of what it was, what it was for, who it was for. I was typing and blogging and broadcasting in an effort to figure out what it was that I was trying to do, and who it was supposed to be for.
There was a part of the process, at least in the early stage for me, that involved allowing myself to – without trying to contribute to the clutter – put stuff out that was just good enough to help me get what I needed, which was the clarity. So that I could better serve the people that I was aiming to serve.
At this point in your journey, you seem to be very clear and very precise with who it’s for and the change that you’re trying to make.
It’s funny. Through CD Baby years and even a little after, I felt like every single person I knew was a musician or connected with music. Then a year after CD Baby, suddenly I was on stage at TED. Not just once, but actually I went on the TED main stage three times in one year. For the following years, everybody I met knew me from the TED conference. People would ask, ”So what did you do before, TED?“
That was such a great moment for me because I really thought that CD Baby was going to be the peak of my career. It was really nice that it hasn’t been. It got a little confusing because now it felt like everybody I met was a TEDster, they call themselves.
Then, Seth Godin asked me to write a book and so I put out my book, Anything You Want, in 2011. It’s about starting, building, and selling a company. All of the people that met me through that book think of me as this tech entrepreneur because that’s the way it comes across. So I was meeting a bunch of these tech entrepreneurs that I have almost nothing in common with.
I got really confused about who my audience was. Now it’s pretty split up. There’s some music people, some TED people, some entrepreneur people. Sometimes I just want to talk about my kind of pop philosophy ideas on how to live and some people in my audience say, ”This isn’t music, so I’m not interested,“ or entrepreneurs say, ”This won’t make me any money, so I’m not interested.“
I am a little mixed up with who I’m talking to, but I’ll just keep carrying on and see who’s interested.
I’ve been following you since the CD Baby days, and I see a simpatico. I see a fellow traveler, I see a seeker and a striver. That’s what appeals to me about what you share. It was great that you helped me sell CDs.
Thank you for that. Believe me. The TED talk phase was inspiring. The book was very inspiring. In fact, I got the book for Christmas about eight years ago.
I continue to visit your blog today because you have a perspective on the journey that is different but enhances the same journey that I find myself on.
To me, that’s the kind of audience that I see. When I talk to other people that followed Derek Sivers, they’re people like me. They’re people that are on the path, on the journey, and looking for some insight and inspiration that will help them get where they want to go.
Cool. Thank you. So what have you found? Who’s listening to us now?
A lot of this audience is attached to the work that I do with and for Seth Godin and the Akimbo workshop. So there are altMBA alums and Akimbo workshop alums and just followers. I call them Sethlings.
[Laughter] I’ve never heard that! I love that. Sethlings!
[Laughter] Sethlings. That’s definitely a big part of it.
A lot of my list jumped from being followers of me, Scott Perry, musician, to Scott Perry, I-don’t-know-what-I’m-doing, to eventually Creative on Purpose, and they’ve stuck with me. Again, I would argue that all along, I think that the thread of seeking and striving to be and do more and be better at both has been a thread that causes people to continue to follow me.
I’m sure there are people here because, in the Seth world, you are a well-known and famous celebrity name. Maybe notorious as well. So they’re people like you and I. People that are living the dream. Acting as if, and eager to see what’s next.
By the way, cute story about my book. Since now that I know we’re talking to Sethlings, you guys will appreciate this. People asked me for years to write a book and I said, “No. I don’t feel like it. I want to write a book. I post my little articles. That’s enough.”
I had a staunch “No” to anybody who asked. In 2011, Seth called me. Not emailed me, called me. My phone rings, 914 area code. He says, “Derek, it’s Seth.”
I said, “Oh, hey Seth.”
He said, “I’m starting a publishing company and I want you to be my second author.”.
I said, “OK.” [Laughter]
And that was that. I really did the book because Seth asked. So that was kind of funny. Now I’m totally into it and I should be releasing three new books this year.
Oh, fantastic. As we’re wrapping up our time together, are you willing to give any hints?
Sure. The one I’m most excited about is the third one called How to Live, which is 29 one-sided arguments, answering one question with one conclusion. I’m so damn excited about the book called How to Live that when I started on it two years ago I thought, “Oh, man, this is big. This is exciting. This is huge!” Then I thought, “Well, I have to put out my previous writing before I released this. I want to honor the chronology of it.”
So while I’ve been working on How to Live, I’ll put out my collection of writing for musicians called Your Music and People. Then everything I’ve done since 2010 until now, I collected up the best of all of it and I’m calling it Hell Yeah or No, which are general thoughts on what’s worth doing. Then the third one after that will be How to Live.
Hell Yeah or No came up in a conversation in Seth’s community earlier this morning in a conversation that I was part of. That one idea perhaps is one of the most profound and powerful ones that you’ve ever shared. It’s had a huge impact on me and making progress in my endeavors.
I love the whole concept, and I would really love for you to just unpack quickly with that means for everybody else because it’s such a powerful idea.
First, I should say, it’s a specific tool for a specific situation. When you’re overwhelmed, if you’re spread too thin, if you’ve said yes to too much. The idea is, you’ve got to raise the bar all the way up. If anything that you’re presented with is making you feel anything less than “Oh, hell yeah! Oh my god. That would be amazing!”
If it’s anything less than that, you just say no. You say no to almost everything. The reason is that most of us feel that we’re supposed to fill up our time, but because you’ve filled up your time, you don’t have any time to throw yourself in completely when you find something amazing.
Instead, you say no to almost everything. So when that rare 1 out of 1,000 thing comes along, you can give it the biggest damn yes. You will have space and time in your life to throw yourself into it completely.
Ultimately, that’s better for your career, for your life, for your peace of mind. It’s more impressive to kick major butt on the occasional rare thing you say yes to. Instead of kind of half-assing everything else along the way. That’s the hell yeah or no philosophy.
I love it. In a way, you’ve answered the traditional last question, which is to deliver a one-piece tip or piece of advice that you’d like to leave the listeners with that will help them fly higher in an endeavor where they strive to make a difference.
Yeah, let’s do that!
What’s your top piece of advice or tip for somebody that wants to do better with, and for the people that they care about?
Ask them! Since you put it that way.
So many people guess what people might be wanting, but if you just ask them directly, it is so useful. One of the best things I ever did my last year at CD Baby, I had time on my hands, I sent a two-sentence email to a quarter of a million people in my database saying, “Hey. I’ve got time on my hands now. What can I help you with? Lay it on me.”
I got around 180,000 replies from people telling me exactly how I could help them in their own words. It was wonderful. Not a SurveyMonkey, not click this and fill in this box. No, just open-ended, this is important. Take the time to ask an open-ended question and listen to people’s replies.
I love it. Thank you so much, Derek, for sharing some wisdom and part of your adventures in living well. Thank you, everyone, for tuning in. We appreciate you letting us have some of your valuable time and attention. We hope that today’s broadcast motivates you to lean into an endeavor that matters with greater curiosity and courage. Learn more about Derek Sivers at sive.rs. Is that correct, Derek?
Yep. sive.rs. With a podcast now, too.
Of course, it’s always great to see you at creativeonpurpose.com. Now, go out and make a difference. Keep flying higher. Derek Sivers, thank you so much for your time today.