Interviews → Bucket List Life

Trav:

Hey, Hey, Hey, Bucket listers, welcome to another episode of the Bucket List Life Podcast. I’m so stoked that you’re here with me, and I’m so stoked that you’ve tuned in to another episode and, boy, what an episode this was. I spoke to Derek Sivers. You know, sometimes you speak to some people and just walk away absolutely inspired. He just got me thinking and really has affected me. I’ve got to say - not discounting any of the other guests that we’ve had on - but Derek is just a deep dude. He’s a deep thinker. He’s a professional musician/circus clown in a formal life, yes.

I love random people, and Derek is certainly one of these random people. He’s a music entrepreneur. He has sold a company by the name of CD Baby for $22 million. We talked about retiring and how retiring has an effect on his life - unbelievable stories. He has published 34 books. I mean, talk about having a goal. He’s done 3 big TED Talks, and the people, as he’ll mention in this episode, he’s got some big names in the audience, like the guys from Google, etcetera, etcetera. By the way, his TED Talks have been seen by something like 7 million people, a big deal. I saw those TED Talks probably about 3 or so years ago, which were amazing. I’m gonna put all those in the show notes here by the way, too.

We talked about what does a guy like this - ’cause he does random stuff - what does a guy like this put on his immigration card when he enters a country, true to his discussions with Tim Ferriss. He’s a mate of Tim Ferriss. What makes him so interesting? What have been the highlights, the lowlights? What is that he’s learned during his very colorful CV? We go through his CV, his resume, as you were and as you see, very random. What’s a typical day in the life of Derek? What’s some advice that he’d give to his 25-year-old self? Who impresses him and why? And then we get into, and I love talking about this bit, ’cause he’s got a talk on “Keep Your Goals To Yourself” as one of his TED Talks.

So, in relation to Bucket Lists, I asked him about what a bucket list means to him, what’s on his bucket list, and should we keep our bucket list to our self. He’s got some really interesting opinions on that. And really what he’s working on? Look guys, there’s a bunch of show notes here. You gonna absolutely love this episode. I am thrilled to be able to bring this stuff to you. Derek is such an interesting dude and has fully inspired me. Just enjoy. Thanks, guys.

[Welcome to the Bucket List Live broadcast with Trav Bell, the world’s number one bucket list expert. Bucket List life’s mission is to help you get off the thread mill, stop ground hog days, pack your habits and live a regret-free life, because we know life’s way too short not to live your bucket list life. So, please welcome your host, Trav Bell, the bucket list guy.]

Trav:

Hey bucket listers, this is Trav Bell, your bucket list guy and on behalf of the global bucket lister community, I’d love to welcome you to another episode of the Bucket List Life Podcast. The Bucket List Life Podcast is about turning the people who are out there living their lists, hacking the life experience to give you, the listeners, inspiration to play a bigger game and, boy, do we have someone who’s extremely interesting. You’ll see why in a second. Derek Sivers is on the show. Derek is a professional musician and circus clown, interesting, in the past, whether you do that now these days or not, we’ll get into that; a music entrepreneur that sold a company by the name of CD Baby for $22 million, a writer with 34 published books, speaker, having done 3 TED Talks with over, and I count them Derek, 7 million views now.

Welcome to the show.

Derek:

Thanks, Trav.

Trav:

I’m sure I could go on and on and on with your introduction but we’ll delve into it now. First question: You’re over there in New Zealand. You’re originally from California. When you’re coming into New Zealand or when you travel internationally, what do you put on your immigration card when you enter a country?

Derek:

Ahh, trick question. Guess what? I have a little story about this.

So, a few years ago, after I sold my company, my girlfriend and I brought two bicycles into England with the idea of doing this kind of cross U.K. bike ride. I think it’s Land’s End to John O’Groats. It’s like from the very southwest corner to the very northeast corner and it’s supposed to be a great bike ride and we’re coming in from Brussels on the Eurostar train and I thought nothing of it. I kind of met the border guy, the immigration guy, handed him our little blue cards where we tick the boxes saying how long are we gonna be here, and I think I wrote a month or something like that. And so he asked again, how long are you gonna be here, I said, “Well, probably about a month.” And he said, “Well, what do you mean probably?” I said, “Well, we’re gonna ride our bikes from one end to the other,” and he said, “Well, what is your source of funds?” And I said, “Well, I have money, it’s okay.” And he said, “Where do you work?” He said, “What do you do?” I said, “I’m a computer programmer.”

See that used to be the answer I put on the immigration card. I use to say programmer. So he said, “What do you do?” and I say, “Programmer.” He said, “Where do you work?” I said, “I just work for myself.” And he said, “Who pays you?” I said, “I don’t know; various people.” And then he asked me a few more questions and he was not satisfied with these answers and he said, “Look, I don’t think I’m gonna be able to let you into the country unless you can tell me about your source of funds.” I said, “What’s going on? All right, look, this is a little embarrassing but...”

Trav:

I can picture you do this exhale in front of him.

Derek:

Yes. I said, “Look, last year I sold my company for $22 million. I’ve got plenty of money. It’s not an issue.” He said, “Oh, just put ’retired’ then. God you’ll make our life a lot easier. You fill out one of these immigration cards. When it asks your profession just write ’retired.’”

Trav:

Sweet.

Derek:

It was an interesting lesson for me. I don’t feel retired, but as far as a government’s immigration program is concerned, I’m not taking anyone’s job. So, I guess I’m retired.

Trav:

You are not someone who, from doing the back story research, you are not someone that we put in a box and you, certainly, in your TED Talks and your books, from what I’ve read and seen, you are straight out of the box and that’s really what you talk about, isn’t it? You’ve done some amazing stuff. I really don’t know where to start, to be honest. I think we have started, though. What does make you so interesting? Please, give us a back story on your CV.

Derek:

I think what’s interesting to others or why my CV seems strange is that I’m not doing this for the usual reasons. I think when I was very young, when I was 21, my first serious girlfriend grew up on a commune in Vermont. It was a real hippie family, grew up without electricity and they just kept their cost so low, like her family kept their cost so low, that they never had a regular job. They would just do random little odd jobs when they felt like it, and yet that was enough money to put their daughter through college. That was a big influence on me. So, honestly, Trav, I quit my last job in 1992 and I haven’t had a job since. I’ve just done a lot of random things that I felt were interesting or that I felt were a challenge that would help me grow or develop in some way. And it was never ever about the money, because I always found a way to keep my cost super low, so as long as I found a way to make a few hundred dollars in a month that covered my cost, then I’m good to go.

Trav:

So go with intuition, what makes something interesting that’s where you paid attention, yeah?

Derek:

Right. Well it changes all the time so, say for 10 years, when I was running my company CD Baby, that’s what was interesting to me. I was completely fascinated with how to make this little project into the best little seller and distributor of independent music. I just got completely fascinated with it. So, 7 AM to midnight, seven days a week, that was all I wanted to do. It wasn’t work. It was just my fascination. But then after 10 years of doing it, I hit a point where I just felt done, kind of a painter with his final brush stroke on the canvas and steps back and looks at it and says, “Yeah, that’s done.” So I felt done with CD Baby.

Trav:

It’s sort of one journey to another. One interesting topic to another as you go through life, yeah?

Derek:

Yeah. So, in fact, a year after CD Baby, or maybe about that time after I sold it, I felt like I had just been doing nothing but music for 20 years. I was so immersed in the music business that suddenly TED fascinated me. I use to watch a lot of TED Talks and I was like, “This is the world I wanna be in. I wanna be in this world of intellectuals and thinkers and writers and speakers. Yeah, that’s what I wanna do.” So I really made it like this deliberate goal. I want to be known as a writer-speaker-thinker dude. I wanna speak at TED. And sure enough, within 9 months, I did it and not just once. I spoke at TED three times.

Trav:

Yeah, I know. What is it? One of them got five million hits. I thinks it’s 3-, 4- and 5 million hits on each one. I look at your TED Talks, in particular “How to Create a Movement” and your “Keep Your Goals to Yourself” TED Talks, which I’ll get into in a second. That “Create a Movement” was unbelievable. That’s your highest ranking TED Talk, isn’t it?

Derek:

Yeah, it’s kinda my hit single.

Trav:

Oh, my god, I saw that. That’s back in 2010 I believe.

Derek:

Yeah.

Trav:

And I would have looked at that when TED came out it was one of their signature videos on their highlights reel when you went into the TED website. So you connected with TED and then they said that this is a great idea when you pitched the idea to them? How did that come about?

Derek:

Yeah. It was something I had already written up on my website in a blog post that some people had seen and, yeah, the way they work at TED is it’s mostly invitation only, but if you’re already attending you can pitch an idea to them for a little 3-minute talk. So, yeah, I pitched a few ideas and they liked that one and asked me to do it. But it’s kind of funny how that works. All I was focused on was the room of people in front of me. Man, it was an intimidating, fucking room. It was like, there’s Al Gore, there’s Bill Gates, there’s the guy that started Google, there’s Tony Robbins.

Trav:

You see, you went into the TEDx. You were at the big TED Talks.

Derek:

The big, big, yeah, all three of those talks are at the big, big TED and so, that was an intimidating room, man, like, there’s Bill Gates just sitting there. It’s like, “What the hell can I say that’s going to be something he doesn’t know already?” So all I was worried about was impressing that room. I had no idea that they were gonna go put it on their websites. So, yeah, it’s kind of funny.

Trav:

You were so thrilled doing those. You’re very good at controlling your nerves.

Derek:

I was not, man. If I’ve ever been at risk of a heart attack, man, I’m surprised I didn’t die. I can’t believe. You think I’m thrilled during that moment? That just shows how nervous everybody was on stage ’cause, man, like my heart was about to explode while I was doing it. I don’t even smoke. I have to run off stage and ask somebody for a cigarette. I was just like, “Oh, my god, I finished.”

Trav:

TED made me stop smoking. What was the feedback--the immediate feedback? Who do you got in the audience? Al Gore, Tony Robbins. What was the immediate feedback? Did you get a chance to get feedback after your talks?

Derek:

Yeah. Actually, a really sweet thing happened. I mean, the most immediate feedback is like I got a standing ovation. That just doesn’t happen much at TED. That happens once a day. So that day it was me. That was very flattering, especially considering how nervous I was, so that was awesome. But then my favorite moment? I’ve never really written about this. About half an hour after I finished, I’m outside and they kind of hang out area there in California inside the TED, whatever conference zone, and I see Peter Gabriel and I actually see him and interrupt his conversation he’s still having with somebody. He kinda puts a finger up to them, interrupts them, stops what he’s doing and comes up to me to shake my hand, and he’s like, “Really powerful talk. It was profound and it was funny.” I said, “Thank you, Mr. Gabriel.”

Trav:

How old are you now? Can I ask?

Derek:

Forty-five.

Trav:

Forty-five. What have been the highlights in your working/just journey? What would have been the highlights for you apart from TED?

Derek:

I gotta say, selling a company is everything it’s cracked up to be. That was awesome. It’s kind of amazing to talk about that immigration card, to actually feel retired so that it changes the way you look at the world, to not do things for money anymore. It’s actually kind of a hard habit to break. My whole life, it’s not that I was so money-driven, I mean, probably less so than other people, but it’s just something we all live by. We’re always trying to make money. It’s just what we all do. It’s like animals are out there, they’re always looking for food and people are always looking for money. So it’s a really hard habit to get out of. So I think that definitely changed my life. That’s, probably, the single biggest change.

Trav:

Right. Has that allowed you to be more creative?

Derek:

Good question. No. I mean, allowed? I mean, I’m allowed to do anything.

Trav:

Yeah.

Derek:

Fuck everyone, I could do whatever I want. Does it made me more creative? No. Thanks for asking that. That’s a really interesting question. I think there’s a creative necessity that happens. I think Leonard Bernstein said, “To create great things, two things are needed: a plan and not quite enough time.” When you have to do things on deadline, or in short, when you have to do something, that can be an amazing creative spark, right?

Trav:

True, true.

Derek:

I had the luck of meeting lots of famous songwriters in my life and I’ve often asked them, “How do you do it? You’ve already had hit singles. You’ve had a lot of hit singles. You’re a multi-millionaire. What drives you to go write another song?” And many times they tell me, it’s the deadline. The record label says, “We need your new album to be finished” or even Sammy Cahn, who wrote all those great Frank Sinatra hits. I worked with him when I worked at Warner Brothers, so I got to ask him, “Why do you do it?” And he said, “Because they asked me to.” He said, “Write me a song about Christmas.”

Trav:

I like that saying “If it wasn’t for the last minute, I wouldn’t get anything done.”

Derek:

Nice. I love that, yeah.

Trav:

If you do get extremely creative I like it. So what have you learned?

Derek:

Oh, nothing at all.

Trav:

B.S.

Derek:

You ask me a smartass question, you’ll get a smartass answer.

Trav:

We’ll move on. What I’m interested in knowing is with your life now, like, you’ve sold a massive company, you’ve pocketed a bunch of cash, what is a typical day in the life of Derek Sivers look like?

Derek:

Well, I figured out that I really like working alone. So I think I had to notice that all the times in my life when I felt most exhausted is always when I was around other people and that has just exhausted me. Whereas if I work alone, like physically alone, even though I may talk on the phone five or six times a day to friends or interviews like this, I really like being alone. I, also, for some reason, I always wake up really early in the morning. I don’t even know why. I don’t try to, but I’m always up at 4:30.

Trav:

Really?

Derek:

I wake up in the dark at 4:30, make a pot of tea and I start writing. I start writing on whatever I’m working on. Sometimes I’ll start programming or answer emails and I keep doing that all day. I tend to get into one thing at a time, like, there will be three or four months where I’m doing nothing but programming all waking hours, right? And then, the next three or four months I’ll be doing nothing but working on a talk that I’m giving at a conference. So, yeah, I tend to just dive into one thing at a time. So right now I’m programming and, in fact, I made a little page on my site because people ask every now and then, like, “Hey, man, what are you working on?”

Trav:

I saw that, yeah.

Derek:

Flash Now. That’s the page that tells you what I’m doing now and any time I change what I’m doing I update it. It even shows you the daily output of my computer programming if you’re really that interested.

Trav:

Yeah, I did see that. You did put some computer programming stuff up there, too, which lost me, but I’m sure someone knows. Even for this interview, which was really interesting. You’re on Linux and that’s something I haven’t heard since, I think, the early 90s. Linux, you’re not on Windows, you’re not on Mac.

Derek:

Yeah, it’s because I have some web servers out there in the world and years ago, when CD Baby was growing, I couldn’t afford to pay someone to run them for me, so I had to figure out how to it myself. So sure enough I went and got a couple of manuals on Linux web server administration and learned the Apache web server and post GRASS database and it’s that and so I found that a great way to learn them was to actually “eat your own dog food,” right? By having my laptop running the same software that my server was running, I could always test out things on my laptop first before I push them out to the world, and I just kind of got stuck on it. It’s a really nice, minimalist, non-commercial operating system that you can do anything on. I love it.

Trav:

Yeah, cool. So, what time of the day in your typical day are you the most creative, you feel?

Derek:

Isn’t it usually, I think for most of us, it’s those hours where nobody else is expecting anything of you, so you can just carry on doing whatever you’re doing without interruption, right? So, whether that’s early mornings or late at night, I think it’s that lack of interruption where even if you don’t actually get interrupted, it’s a different mindset.

Trav:

It’s so true, yeah.

Derek:

Nobody’s looking for you, nobody’s trying to reach you, nobody’s expecting you to be on call. Even for me, I’m not beholden to anyone yet, still, I find that those hours just feel the best. God, I love those things where sometimes I would just sit down, dive into something and I’d just be programming and totally focused on what I’m doing, right? And then I’ll stand up and it would be like 10 PM, and I’d realize I hadn’t turned any lights on ’cause when I sat down it was 5 PM. It’s like, whoa, I haven’t even gotten up to pee in 5 hours.

Trav:

That’s what we call “flow,” isn’t it?

Derek:

Yeah. You know, that was a pretty profound thing I found is one of these books I’ve read said that people interviewed at the end of their life, the ones that claim to be the happiest with their lives were the ones that had spent the most amount of time in that state of flow. It’s like there’s a pretty direct correlation to your happiness in life is how much time you’ve spent in that flow zone.

Trav:

What makes you happy?

Derek:

Learning for the sake of creating. Let me tell you a tiny little story around that. I worked with a guy once. He was kind of like a business mentor, business coach of mine, but somewhere kind of segued into life stuff sometimes. So he asked me, “What is your single most important value?” I said, “I don’t know.” He said, “It’s okay. Most people don’t know. Tell me something that’s really important to you?” I told him something, I don’t know, “Programming.” And he said, “Well, what’s important to you about that?” And I said, “Oh, hmm,” and I answered. And he said, “Well, what’s important to you about that?” And then he just kept going and drilled down until we got to the core values. To me, it came down to two. It was learning and creating, and he said, “Now, ultimately, which one of those two is more important to you?” And even though for every other stage I had an answer for him, I knew which one was more important, this one I was stuck ’cause I’m like, learning or creating, which one is more important? No, neither. Equal. They have to be equal. He said, “No, at some point you have to decide which of those two things is more important to you.” And I thought about it for a bit. “No, I don’t, because you know what? I refuse.”

I mean, different languages have different words for different things, right? If you Google there are a few different websites I’ve seen that do this. Google for something like “words that don’t exist in English” or “concepts that don’t exist in English” and you find that different languages, whether Portuguese or Arabic or whatever, have a single word that in English takes like a whole paragraph to explain, but in that language, it’s just a single word. So I pushed back on this dude, saying like, “Actually, no. I think it’s kind of the fault of the English language that this is not one word because, really, it’s one concept, and here’s the one concept. It’s learning for the sake of creating.” You get what I mean?

Trav:

Yeah, I totally get it.

Derek:

Learning things for the purpose of creating things which, then, even loops around from some word that I’m creating things for the sake of learning, and I’m learning for the sake of creating and creating for the sake of learning. So to me, that is one thing. That’s one concept. The fact that it takes two English words to describe doesn’t mean that it’s two things. That is my one thing. That’s the main thing that I’m all about, learning for the sake of creating for the sake of learning.

Trav:

Yes. If you haven’t got that in your life, for whatever reason, it doesn’t give you fulfillment. You don’t feel like your own purpose if you haven’t got that in your typical day.

Derek:

Yeah.

Trav:

Yeah, cool, cool.

Derek:

Yeah, very good point. Great.

Trav:

What would be some advice to your 25-year-old self that you’d give to yourself?

Derek:

What was I doing at 25? I was with my band.

Trav:

Probably rocking out somewhere?

Derek:

Probably this and so I’m gonna generalize this a little bit for your audience. I find a lot of us, especially a lot of entrepreneurs, but even some creative artist types get stuck on one idea and they’re just convinced that this idea is the one. And they’ll spend years trying to make this idea work when the world is basically telling you, “No, that idea just doesn’t doing it for me.” So whether it’s like a band that keeps on gigging and keeps on gigging and it’s a struggle every time to just get 10 people to come down to your gigs, or if it’s an entrepreneur that’s got some idea, whatever, it’s Uber for makeup, whatever, and they just push this idea and they push it and they push it and they have a hard time and they’re out there and they’re trying to raise financing and they say, “hey, persistence is key; perseverance.” And they keep doing this thing that nobody wants. So, my advice to my 25-year-old self and a lot of other 25-year-old selves out there that are really stuck on one idea is to let it go.

I found being in the music business that the most successful songwriters were not the people that had one song that they really believed in and spent years banging their heads against locked doors in Nashville, New York and L.A. trying to get people to record their one song. No, it was the songwriters that wrote a song or two or three every week and they just kept writing and kept writing and kept writing, and every now and then, something they wrote would just hit in the right place at the right time and become a big success. And even then, they just kept writing and kept writing, and those were the most successful songwriters I ever saw. So I think entrepreneurs could really learn a lesson from this that when you’re trying an idea and the public just isn’t really freaking out and opening their wallets, begging you to take their money, then just move on and try a different idea.

This lesson that we hear all the time about how we have to be persistent. I think we’ve misunderstood the word persistent, thinking that it means we need to do the exact same thing over and over again. Really, I think, it means we need to persistently keep trying different things until we find out what works.

Trav:

Yeah, yeah, got that. That’s cool. I like it. Great advice. Who impresses you and why? You’re very worldly. You’ve read well. You’ve met some world leaders. So who impresses you and why?

Derek:

Let me see. Usually people that I’ve befriended, number one, actually, it’s usually the authors of my favorite books. I’m a real book junkie if you couldn’t tell. Books have been my main form of mentorship and have been the main source of all my learning for years. I know everybody has their own styles. Some people love podcasts. Some people love going to seminars and conferences or workshops or things with big groups of people in person, but for me, it’s books.

Yeah, so the authors of the books that I love are probably the people that I’m most impressed with, but for the most part, when I’m really impressed with somebody I try to reach out to them and get to know them. So these days I often think of them as just like my friends. People like Tynan or Tim Ferriss or Remit Sethi or [29:54]; people like that, that if I’ve just become friends with. Let me pick one just to give you a non obvious example.

On the entrepreneur side, I’m really impressed with this guy named Rob Walling. W-A-L-L-I-N-G. He has a website called micropreneur.com. M-I-C-R-O-P-R-E-N-E-U-R. Micropreneur.com and he wrote a brilliant book called Start Small, Stay Small. I think it’s a great must-read, especially for solo tech entrepreneur. If you’re just the kind of person that likes doing things and you want to have a little online company that can be profitable but doesn’t involve you gathering together 20 people and raising a bunch of financing. Check out Start Small, Stay Small by Rob Walling and check out his site.

Trav:

Cool, cool. Rob Walling. What impresses you about Tim Ferriss?

Derek:

Tim and I met in 2007 right after his book came out. He’s just one of those people that just turns out that we’d read all the same books and just like suddenly we were speaking in shorthand the minute we met. We’re just like our brains were connected. It was a really cool thing. We’ve been friends for years. Within this, he broke up with his girlfriend and then a year later he sat with me as I broke up with my girlfriend. So I know him more personally than professionally. Actually, we haven’t spoke as much lately because I often, before calling him to run something by him, I often think what would he say, and at this point I know him well and so I can kind of imagine what he would say, so then it’s like we’ve spoken and then I kinda take off letting inspired by something I think he would have said and then we talk later about personal stuff. So, yeah, some people you just admire their thought process.

Trav:

Yeah, that’s definitely one thing that I admire and having met the guy, I had lunch with him a few years ago. It wasn’t just me. There was a small group of people in [32:22] when he came to town to do a talk and, yeah, he’s just interesting guy, very, very humble and very determined but casual. I love it.

Derek:

You know, if you want to think differently than most people, you gotta have that confidence to get your thinking from a different source, like I talk about look into books or alternate sources of influence. If you’re just getting the same input as everybody else, then you’re very likely gonna have the same output as everybody else and I think sometimes you have to look for different sources of input that everybody else is getting and even just, intentionally, taking a different approach to things than others are taking like looking at what everybody else is doing and just trying the opposite, even if it’s the wrong thing to do. But then, just on principle, at least you’ve tried the opposite that gives you a different set of insights in a more unique point of view.

Trav:

Talking about that, you know I’m known as the bucket list guy and I talk about bucket lists and, normally, on this show, we do talk a lot about bucket lists and I’m interested to get your viewpoint on bucket lists, especially giving your TED Talk on keeping your goals to yourself.

Derek:

Okay. I have a lot to say about this.

Trav:

Bring it, love it.

Derek:

Not about the TED Talk, I mean, about the subject of bucket lists in particular. It’s kind of a subject of mine. It’s a big reason I was excited for our conversation. First, just to get the TED Talk out of the way, to be clear. So I mentioned earlier how TED works that you just kinda pitch a couple of ideas that if you’re already an attendee and especially for those short little 3-minute talks, they may just pick one. So that year I actually pitched three different ideas at them. There was talk number one, which I really wanted to give, talk number two, which might be nice to give, and then just like as an afterthought, I, literally, that same day they were requiring applications, I have read an interesting little Newsweek article. It was only like four paragraphs long but it just said, studies show that people who announce their plans get the social satisfaction, the pat on the back from their friends saying good on you for doing that, and I could never run a marathon. Wow, you’re more determined than me. And just feeling that bit of social satisfaction makes them less likely to do the hard work necessary to complete their goals, right?

So I read the Newsweek article that day, I was like, “Huh, I could talk about that. That’s kind of interesting.” And it was like an afterthought and, unfortunately, that’s the one they picked. So, suddenly, I have to get up on stage like I’m a damn expert or something. All I was doing is just quoting this dude’s work. One important fact in there that got lost in this two and a half minute delivery of a big idea is that it only applies to what they call “identity goals,” which are things more about your self identity, such as, like, I’m going to run a marathon or I’m going to learn this.

Trav:

[35:45]

Derek:

Yeah, but importantly, identity goals, and even then, this whole thing about announcing them to others, it only has shown to be a 30% influence on whether they get done or not. It’s not like a hundred percent, if you tell somebody your goals they will not happen. No, it’s just a 30% nudge that makes identity goals less likely to happen. But then, goal setting are things like, “Hey, I’m going to start a business.” It’s doing such and such. You should tell everyone, because the more feedback you get, the better. The more ideas that you get from the world, the better, and the more people that know you’re doing it, the better.

Trav:

And the resources might turn up a little bit faster, too, yeah?

Derek:

Exactly. Anyway, I think that TED Talk of mine was kind of misunderstood, but, I mean, who cares.

Trav:

It gets people talking and your views on bucket lists, I love to hear them.

Derek:

Yes, okay. A few years ago I thought about--I didn’t think of it in terms of bucket list at first--somebody later told me that what I was doing was making a bucket list. I thought of it as what if right now I was on my deathbed, what would I be the most upset at having not done? And I thought about that for a while and I made a list. I found it in my diary before we talked. It was March 22nd 2009. I sat there with my diary. This, man, if I were suddenly, right now, get hit by a car, my guts were bleeding all over and I realize I was dying, I had a minute to think about the fact that this is it for me. I was dying. I would actually be most pissed about these things.

Trav:

I just so wanna know what those are, then. What are they?

Derek:

I’ll tell you some of them, but a lot of them are private. But most importantly, after making this list, I looked at it and I decided to put a timeframe on it, like, how long would that really take to do, right? So let’s just pick a couple of the easy ones. I would really love to see China and I don’t mean just visit Beijing for a few days. I mean, I’d really love to go across China and stay with a guide from China that could show me around, really help me understand that big hard to understand country. And so I looked at something like that and I’m like, how long would that really take? Three weeks? Okay, let’s just say three weeks. Three weeks to do a cross country tour of China, but pretty surreal.

And then, say, like, scuba diving the Great Barrier Reef. How long would that take? Two days? There’s some things on the list that when you look at it, if you really focus on it, wouldn’t take that long to do.

Trav:

Oh, my god, we are speaking the same language, bro. I love it. I know it’s just the concept is overwhelming more than the actual doing.

Derek:

Yes, exactly. So even something like I want to be fluent in Spanish or Mandarin. There are quite a few websites out there that people are proving that you can get quite fluent in the language in three months and if you give it six months, you can certainly be fluent if you’re focusing on it. You’re taking the right approach. You’re using your space repetition flash cards. You’re immersing yourself. You’re in the country. You’re speaking it all day. Yes, you can be fluent in three to six months. So even something like I want to be fluent in a language, well, if this is important to you, then just go fucking do it, right?

Trav:

Doing the whole talk, I’ll just pretty much summarize, “Just go fucking do it.”

Derek:

Yup. Yes, that’s it. So, there were some things I noticed that under timeframe I wrote “infinity,” like, I wrote telling my tale, it’s like sharing what I’ve learned, so it’s like that’s not something that I could say, “Okay, check. There, I’ve done that.” No, it’s just an ongoing thing. That’s more like that’s the way I want to live, yet I still think it deserves to be on this, whether you call the bucket list or my deathbed regret list. I called it my deathbed regret list.

Trav:

It’s gonna be leave a legacy, too.

Derek:

Yeah, to me it was more like I would regret not having lived according to this belief or whatever you want to call that. I believe that I should tell my tales and share what I’ve learned or here’s an important one, a term I like--being fit and eating healthy. Like if you’re on your deathbed because your fucking arteries are clogged up and you haven’t exercised ’cause you’ve been sitting on the coach and that’s why you’re on your deathbed, and yet, you sure as hell would regret that you didn’t spend your life skipping a donut and eating your vegetables and just finding 45 damn minutes in the day that just go out on a nice healthy long walk or something. Yeah, that would certainly be a deathbed regret, but that’s not like a To-do list, that’s a daily [41:10].

Trav:

Yeah, that’s a habit. Interesting. I love it. You’ve really encapsulated a lot of my thought processes as well, but you just said a lot more eloquently, mate.

Derek:

Actually, before we changed the subject, I told you I mentioned earlier there was this guy, Jared Rose, that I worked with. It was kind of a business consultant, kind of a bit of a life consultant. So I first met him when I wanted to get better at the Ruby programming language. Well, technically, I just wanted to learn it. I hardly knew it at all but I wanted to master it. And, to me, that just felt like this big, overwhelming thing, like, I want to master the Ruby programming language, right?

So, he said, “Okay, how would you know that you’ve mastered the Ruby programming language?” I said, “Actually, I got these six books--these six big, giant, 300-paged programming books. Four of them are beginners, like, two beginners, two intermediate, two advanced books. If I knew and understood everything in these books and could quiz myself on it, and, basically, rewrite the book for myself, like, if I really knew these books inside out, I would say I had mastered Ruby.” He said, “Okay, how many chapters are in them?” “So what do you mean?” He said, “Go count the number of chapters. I know it will take a couple of minutes. Go ahead, I’ll go make a pot of tea. Go count the chapters.” So I was like, “Okay, book number one, 23 chapters; book number two, 17 chapters.” So add them all together. I said, “Okay.” “How many chapters does it total?” I was like, “Okay, a hundred and fifty.” He said, “How many chapters do you think you could do in a week?” Let’s say five chapters a week. He said, “Okay, a hundred and fifty chapters divided by five, great, that’s 30 weeks.” So there’s your plan for mastering the Ruby programming language in 30 weeks. You should do these six books, 5 chapters per week. That’s one per day and just assume that you’re gonna take weekends off or just two days a week off. With one chapter a day, five days a week, can you do that?

I went, “Oh, yeah.” Suddenly, it was so big and ambiguous and overwhelming and foggy. This thing is as simple as, “Okay, if you just do a chapter a day, five days a week for 30 weeks, you will have mastered it, like, that’s all there is to it.

Trav:

Yeah, reverse engineer the baby steps. Did you do it?

Derek:

Yeah.

Trav:

Now you’re based with the Ruby language. I love it. What are you working on at the moment? What’s getting your attention?

Derek:

After programming there had been some things that I started years ago that I never finished, some web app ideas that are listed on my site that I announced the date. Actually, this is why the TED Talk, it’s like I announced some of these things and because some of my friends patted me on the back for coming up with this brilliant idea I’m working on, I felt the satisfaction already inside. I never finished the damn ideas, so moving to New Zealand was somewhat symbolic for me. I was living in Singapore for two and a half years and Singapore is an easy place to get distracted. There are so many fascinating people there and it’s such a travel hub that you can go to 12 countries for under $200 from Singapore, and, god, I was becoming like a travel addict, to people addict, to meeting with everyone and doing everything and going everywhere. So I moved to New Zealand to cure my travel addiction. So I’m here focused on finishing the things that I started years ago.

Trav:

Created a little cave for yourself down there.

Derek:

Yeah, cave meeting right here, but touching waves on the ocean, yeah.

Trav:

Oh, nice, nice. Is there anything that you’d like to plug? We thank you for your time and plug away if you got anything to plug.

Derek:

I have a book called Anything You Want that is available everywhere. It tells my tale really. I mean, it’s not a plug. I’d actually like to say that the main reason I do interviews like this is because of the people I meet when I do them. The kind of people that contact me saying, ”Hey, man, I heard you on the Bucket List Guy Podcast.“ So, honestly, the kind of people that listened all the way to this interview are, true, my kind of people.

Trav:

Very cool.

Derek:

I’ll just give you my email address. So if you email me, that’s me. No assistant, it’s me.

Trav:

I love that. I love that.

Derek:

It’s something I actually enjoy doing. It’s kind of hearing from random strangers. So ask me anything or just introduce yourself and I’ll be happy to reply.

Trav:

Oh, I love it and that was my next question. Derek’s website, to you guys, is sive.rs. Why the dot org?

Derek:

I gave my dad the dot com.

Trav:

I thought it was gonna be some philosophical, world giving back kind of moment just now, but, no.

Derek:

Sivers is a rare enough name that I own the dot net, dot com, dot org. I think I got a few others. I think I’m not too greedy, I didn’t get them all, but, yeah, this is like way back in the mid 90s and I was like, ”Nobody else has got it, I’ll take it.“ So, yeah, my dad is actually running a business called The Sivers Company, so I gave him the dot com. You know, dot org is meant for non-profit things, so, yeah, my website is just my personal place. I’m not trying to sell you anything. There’s no ads even if you look in the html source. I don’t even do any of the Google analytics or tracking or nothing. I don’t care. It’s just my personal website.

Trav:

I love it. It’s really very fresh. That’s for sure.

Derek:

Thanks.

Trav:

Yeah, mate, so we’ll wrap things up. Is there anything you’d like to say before we do, officially, say goodbye?

Derek:

Crunchy bacon is a beautiful thing.

Trav:

This is a trippy conversation. I reckon we could have the heap of fun made. When I’m over in New Zealand, we have to have coffee and if not, something else. It’s been very fascinating. I love, love, love talking to interesting people, and you’re certainly one, Derek, and thanks so much for creating some time for us and I’m sure the bucket listers out there right around the world now got something out of that chat and just thanks again, man, so much.

Derek:

Thanks, Trav, I really appreciate it.