Derek Sivers

Interviews → John Fitch / Time Off

subtracting to add value, unlearning, play as work, shallow happy vs. deep happy, doing what you want most

Date: 2019-11

Download: audio (mp3)

Link: https://www.timeoffbook.com/#Podcast


John:

Howdy, everybody. John Fitch and this is the Time Off podcast, which is a part of the Time Off book project. That book comes out in 2020. You could find out more about it at timeoffbook.com. Have you ever heard of Derek Sivers? Well, I didn’t know about Derek Sivers until he was on an interview years ago on the Tim Ferriss podcast. Tim has interviewed some wonderful people on his podcast. Some very successful people. Derek’s interview is still to date one of my favorites. I could elaborate on that, but you could go listen to that interview.

It is a really cool thing for me to say that Derek was on the Time Off podcast recently. Shot him an email, talked to him about the project, and he agreed to do the interview.

A bit about Derek, he’s a musician, producer, was a circus performer, a technology-music entrepreneur, a TED speaker, and he’s published some fantastic books and has some coming up soon. His book is called, Anything You Want.

It’s his story about everything he learned while starting, growing, and selling a business. That business was CD Baby and HostBaby. Derek is an introvert, but when he decides to share his stories, he’s brilliant because he’s a slow thinker and he loves finding a different point of view on the human experience.

He’s now living in Oxford, England. He’s a California native, but I’ll just dive into the conversation. You’re going to learn a lot from Derek. We pretty much talk about everything in life. Thanks for your attention. Enjoy.

Great. Right before diving in, I just wanted to say I’m in the middle of wrapping up my first book, which is based on this podcast. In your post “Cut Out Everything That’s Not Surprising,” was the greatest editing advice that I’ve been given. I’m working with an editor right now, and I was needing a different story for me to do this last pass of editing with my co-author. That’s just my theme. Every paragraph I’m looking at, I’m asking myself that question. So thank you.

Derek:

Nice. For my book, it made a huge difference. When I decided that I was going to print hardcover books because nobody likes killing trees, I looked at every sentence like, “Is this worth killing a tree over?” [Laughter].

John:

Wow.

Derek:

Does a tree need to die for this sentence to live? I said, “If I can possibly make this book fewer pages, I should.”

I go back through every sentence. ”Is this hardcover worthy? No.“ So that was nice editing help for me, too.

John:

Well, thanks for sharing so much. Your frequency has increased on your site. From the comments alone, I know I’m not alone in enjoying the posts. Before we dive in, my first question is how’s that been for you? Just that process of posting something at that frequency.

Derek:

Not loving it. You saw my post about being a slow thinker. It’s often to a fault that people try to stick with their first answer to something. The first answer to something is usually not very interesting. I want to go beyond the first answer. The problem with the daily posts to me is I find that I was thinking in that mentality of, ”I have to come up with a post today. Shit. What am I going to write? I don’t know.“

I’d start to write something and say, ”OK, that’s something I can post. I’ll just use that.“ Before, I would have taken twice as long on this thing. I would have thought it over deeper. I would have slept on it. I would have come back to it a week later and thought about it some more. I would have discussed it with a couple of friends, bounce some ideas around, and come back to that again. Then, post it later once it aged or I had found a more surprising angle.

Because I’m trying to post something every day, it feels like I’m posting them too soon. They’re not worth someone’s time yet. I’m actually on the verge of deciding that no, this is no longer a daily thing. I was doing that just because Seth Godin said to [laughter]. It was exactly a month ago today that I started, so I’m like, ”OK, it’s been a month.“

I took my kid to Paris for a few days and I had no phone, no computer, no nothing, so I didn’t post anything those days. I’m thinking, ”Alright, I think what this exercise has taught me is that I’m going to post more often, but not make this a daily requirement.“ I’m writing every single day, anyway. I write for hours a day, anyway. If I’m feeling like something isn’t ready to post today, I won’t post something too early just because I said I will. I would consider it deeper and maybe post it the next day. That’s where I’m at now.

John:

You are known for enjoying solitude and in one of your posts about disconnecting, when people ask you what they can do to be more successful or to finish something, one of your pieces of advice is to disconnect. That doesn’t have to be for an entire day or a month sabbatical, but the point is, turn off distractions – your phone and wifi. You could create. You could write code. You could practice something. The point is, you’re focusing, and that’s actually rare and valuable these days – to not be distracted.

Can you paint a picture of significant moments of solitude that you’ve had? Based on looking at your site you mentioned at the ages of 22 and 27 were some key moments of solitude. Do you care to elaborate on those?

Derek:

Sure. First, I’ll talk about the reason why.

We have some things in our nature – the biological reason, or the evolutionary or hereditary reason, why when we get a box of cookies, we just want to devour the whole thing. It’s because for eons our ancestors would come across some food, it would often mean that this is the only chance they’re going to get to eat for a couple of days, so they would devour that because that was a good survival tactic. Maybe people who did that lived and people who didn’t died.

Here we are in a different age where eating all the sugar and salt you want is not a smart thing to do anymore. We have to go against our nature and make ourselves stop. We’re in the same thing with distractions, and I’m not just going to blame phones or the Internet because I’m sure it was different distractions 20 years ago and 200 years ago.

I often think in terms of competitive advantage. I like getting a little bit of a competitive streak in me thinking, ”What is the rest of the world doing?” So, almost by default, it’s going to be more valuable to do the opposite because it’s going to show me a different point of view or just help me stand out from the crowd.

Part of the disconnect thing is because of that smug satisfaction you get when you look at the rest of the world and everybody is addicted to their phones. You just know that not doing that will give you an edge. People get literally addicted to the connection to constantly connect and constantly ping and get those little notifications. I think it’s an addiction.

I also have this core belief and whenever I notice that I’m feeling addicted to something by any definition, even if it’s having mints in the car or something like that – I used to always have mints in the car – one day I ran out of mints and I noticed myself going, “Oh, no! I need mints! Quick, where’s the store?”

Then I was like, “Whoa! Hold on dude. What did I just say? I need mints? No, no, no.” [Laughter]. Since that day, no more mints in the car ever again. That felt too close to addiction. I don’t think of myself as having an addictive personality. I’ve never had a problem with drinking or drugs or anything like that, but anything that starts to look like addiction makes me run the other way.

So, with that as context, being hyper connected seems to be something that we need to deliberately avoid. Even if it’s in our nature and everything in our yearning and our wanting seems to want it. Sometimes we have to deliberately cut that off.

You were asking about the other two big times in my life? It was a little bit of a different time, though – meaning these two times when I was 22 and 27 were kind of pre-Internet. It was a more extreme cut-off.

First, when I was 22, I had been immersed in the heart of ambition and drive in New York City. It was a time in my life when I was working seven days a week and had been for two and a half years, hardly ever with a day off. I had a regular day job in New York City from 9:00 a.m. to 6:00 p.m. Then every single Friday at 6:00 p.m., I would dash out of there, run down to the bus station, take a three-hour bus up to New England and do gigs all weekend as a musician. All-day Saturday and Sunday. Then I’d sleep up there Sunday night and I’d catch the 6:00 a.m. bus back down to New York City Monday morning, and go back to my Monday through Friday job.

I’d been doing that for two and a half years and saved up 12,000 bucks. I was like, “Alright! $12,000. I can quit my job now!”

So really, my first disconnect had nothing to do with that little preface. We didn’t have cell phones. There was no Internet. It had nothing to do with needing to disconnect from that stuff because that stuff didn’t exist yet. This was more just me saying, “I want to give my full attention to my music.”

I just thought it made sense to do it somewhere besides noisy, crowded, congested New York City. I found a summer cottage on the Oregon coast in a little town that had a population of 50 in the summer and only two people in the winter. So I went there in the winter for six months. That winter, the population was three. I stayed there for six months by myself. No Internet, no TV, no media – just working on my music full-time. I’d make one phone call a day to my girlfriend in Boston.

Other than that, I had no contact with anybody. It was amazing. That six months, I wrote and recorded 50 songs. I read a ton of books. I got really fit from exercising on the beach and just had a really amazing, transformative time in my life. It was one of those major, major milestones. You know when you go through like a huge change in life? Whether it’s going to college or getting married or whatever people do. That six months at the Oregon coast was like a very clear transformation. After, I came out a different person.

John:

That sounds really active. It wasn’t just that you were sitting there, twiddling your thumbs, staring out at the sky and landscape.

Derek:

[Laughter].

John:

It was a lot of work.

Derek:

I guess we skipped the intro stuff. Hi, audience, I’m Derek! [Laughter].

When you first asked me about doing this podcast, my first reaction was like, “No, dude, I think you got the wrong guy.” Because I am not a relaxed kind of guy. I don’t really do downtime. I’m really, really driven. I bounce out of bed at 5 a.m. and I work every minute I’m awake until I go to sleep at 11:00 p.m. This disconnecting at the age of 22 and going to the Oregon coast, was in the name of that. It’s more like I’m so damn ambitious. I want nothing to come between me and my music. So while I was there for six months, I was up early every single morning. I had an exercise routine. I had a practice routine. I was learning new things. I had a reading routine. I was reading for three hours a day. I was practicing five hours a day. I was writing for four hours a day.

It was intense, but it was me-time. We’ll have to talk about that later – the definition of work. To me, that’s play. When I see my kid sitting there playing with Lego for six hours, we don’t call that work. He’s playing with Legos. I don’t see what I’m doing is any different than that.

When I was 27, I did a version of that again. I was back living in New York City, and I had been pushing myself a little too much. Mostly I felt like New York City was giving me a lot of friction in my life that I didn’t like – the traffic, the noise, the density, the crowds.

So I moved up to Woodstock, which is deep in the forest. Found a little 1920’s barn at a dead-end road by a swamp about a two-hour drive north of New York City. I got a little barn house there and again, just focused on my music. All in all, the common thread between these and other times I disconnected is solitude. Because solitude freaks out some people, but I just love it.

I have often been with someone and wished I was alone. Many times in life. That feels like the definition of loneliness, right? When you’re actually around somebody else, but you feel alienated. You wish that you weren’t there. That to me, feels lonely, feels bad. But I have never been alone and wished that I wasn’t. I have always loved the times I’m alone. I feel like I could do that almost indefinitely.

John:

Well, thank you for looking at it that way, and my goal with Time Off is to expand the connotations of what it means. When I first started, people were saying “Wait, you’re going to only talk about paid time off from work or vacations? That sounds really boring.”

I’m sure you’re familiar with Paul Graham’s “Maker versus Manager?”

Derek:

Yep.

John:

It’s a beautiful example of taking time off from New York City – from the grind, from this concept of being around lots of people where they’re controlling your time – whether you’re aware of it or not, and going more into this solitude, which is you-time.

Yes, it’s a form of work, but it’s time off from some defaults that I’m guilty of myself. Before I know it, sometimes I’m doing ten people’s work, and I haven’t shipped anything for myself. To take time off from doing other people’s work to focus on the things I want to create is this value you just spoke of.

Derek:

Cool.

John:

22 and 27. . .it’s been a while since then, I assume?

Derek:

[Laughter] That was a while ago. I’m 50 now.

John:

Cool. Have you had any significant disconnects or something similar to that in recent years?

Derek:

Anything recent feels different because when I think back about those two times, they were both pre-internet. When I was 22, it was entirely before the Internet was invented. Then when I was 27 and moved up to Woodstock, there was Internet, but it was dial-up modems. It’s interesting to think back about how internet usage with a dial-up modem was a different thing. You would dial the modem to go online. It would make that cute connection noise and then you would go online, do what you needed to do, and then you would disconnect again so that people in the house could use the phone.

I hadn’t thought about that change in a while since preparing for this interview, honestly. That was a really different process. It was this very deliberate thing about how you’d go online, get what you needed, then get offline. I kind of miss that. But anyway, when my son was born, I wanted to give him my full attention. I just realized that’s been the common threads of my disconnecting times – it hasn’t been as much a going away from, as a going towards.

Every time I was disconnecting, it’s because there was something that was so important to me that was just more important than everything else, and I wanted to give that one thing my full attention without any distractions. Every time I disconnect, it’s for that reason. It’s because there’s one thing I want to give my undivided attention to.

The first two that I talked about at 22 and 27, were to focus on my music. Then, seven years ago, I had a kid and wanted to give him my full attention. At the time, I was living in Singapore and I was very social and had a lot of friends there. I was meeting with everybody, and I was in the middle of everything, doing tons of public speaking and saying yes to everything.

Then I had this great six-month-old baby at home and I thought, “You know what? No. I just want to give him every single moment of my non-working time. Any moment I’m not working, that time should go to him. Not him and whoever else asks for it.” Moving to New Zealand was this very deliberate thought of, ”How far away can I get from the rest of the world?“

Even choosing where in New Zealand to live, I avoided any cities and went for a small town called Nelson where I knew nobody and said, ”Here. Here’s where we’re going to raise our kids. Away from all distractions,“ and so I did that for the last seven years. I was basically a half-time, full-time dad, where anytime I wasn’t working, he had my full attention. I did nothing else but that.

John:

In New Zealand, in a remote town where you didn’t know anyone there, just by doing that alone, there’s a lot of disconnecting. I believe you have a few definitions of what you mean by disconnecting?

Derek:

Yes. So I guess that’s what I meant when I said that my younger disconnecting times felt more disconnected because I was physically disconnected from everybody and digitally disconnected. I was just off the map. I was like, ”Bye, everybody [laughter]. I’ll be back in six months. Let me know how it goes.“

You know what’s funny? It gave me a new perspective on the news. It was the O.J. Simpson thing. Just before I went off to the Oregon coast, O.J. Simpson had the whole White Bronco thing. Everyone was like, ”Did he do it or did he not?“

It was in the news every single day. All anybody was talking about was O.J. Simpson. I went away to the Oregon coast, cut off for six months from everybody and everything, and when I came back, people were still talking about it. I thought, ”Wow, I missed nothing.“

John:

[Laughter].

Derek:

You people flittered about the news every single day and you got nowhere. Wow. That just really put the news in perspective for me.

So yes, there are different definitions of disconnecting. You can disconnect physically, but not digitally. That’s what I see in this Instagram culture of, ”Hey, look at me. I’m somewhere super far away and exotic. I’m in Cambodia.“

They’re just on their phones all the time. You’re not really in Cambodia. You’re physically in Cambodia, but really, everything about your presence is back in Chicago where you’re from. You haven’t actually disconnected yourself at all. Part of what defines us as being somewhere is that we’re not somewhere else.

Anyway, when I went to New Zealand seven years ago, I was disconnecting myself physically. I took myself out of the game, the rat race, the grind. I also turned off my ambition for those seven years. You can go disappear somewhere and read, or write, or travel, or whatever, but if you still use the Internet, you’re not really disconnected, like the Cambodia example. We can say that that’s disconnecting, physically – taking yourself away – but staying digitally connected.

The opposite is that you can disconnect from the Internet, turn your phone completely off, or set it in airplane mode. Turn off your home broadband, and you could disconnect yourself digitally, but still be physically present in your regular life. You could still see your friends or hang out with your family, even though you’ve disconnected from the Internet. So that’s disconnecting digitally, but staying physically connected.

Then I was thinking about nuances in that, too. You could disconnect from social media and news, and just stop all of that noise from strangers, but still keep the Internet connection on and just use your phone only to talk to your friends. For example, I think of that as separating the signal from the noise. You shut off the noise, but you’re not shutting off the good quality stuff.

John:

That reminds me, sometimes I’ll stare at my iPhone and wow, there’s so many powerful distraction engines in there, but I asked myself when I was journaling what the most valuable application I had on it was, and my answer came to my Contacts app because those are human beings. I went through all the names, and I actually don’t keep up with all of them because it’s too much to manage. Each name I read on there led to me being billowed in memories of human connection.

Derek:

Nice.

John:

To your point that you can still have this quality communication and this amazing technology. But to sit there, and really ask yourself, ”What am I using it for?“ The Internet can be used to still talk to certain friends directly. You and I are using the Internet right now.

Derek:

Exactly.

John:

But it can also completely overwhelm you with brain candy if you’re not careful.

Derek:

It’s funny, I don’t often look over people’s shoulders at what they’re doing. So it blows my mind when I see people that have Facebook, Instagram, Twitter, and Snapchat on their phone. I go, ”Oh, god, how could you do that?“

I have never in my life had a social media app installed on my phone. One thing that I did long ago that really helped a lot – I don’t think I would have gotten addicted to those things anyway because I just don’t find it that appealing – but if I did, this one hack really helped. For Facebook and Google and wherever else I had accounts, I would use a random password generator to generate one of those really long 32 character, super jumbled random passwords.

I didn’t even know what my password was. When it came down to the option of putting it on my phone where I didn’t have my password manager, I just thought, ”I can’t type that 32 long character jumble [laughter]. Never mind. That’s just not worth the effort.“

Besides, why would I want that noise on my phone? The noise of strangers, when I think of the public discourse, it just seems like everybody is shouting. I would never want that. I would never want to let that into my house. I don’t understand that.

I basically only use my phone to call and text friends and maybe use it for GPS when I’m going to a new place, but that’s about all I’ll use it for. Even on the little browser built in the phone, I went into preferences and I had it disable all cookies. So I don’t even have the ability to log in to any site, and that’s really nice.

If have to look up movie listings or the address of a place I’m going to, I can use the browser for that, but I like deliberately crippling something to make it less useful.

John:

One thing I’ve been very inspired by is in an article where you talked about your son. I was reminded of the beauty in the wisdom that if you really want to learn, teach. You said by cultivating your son’s long attention span, you’re cultivating your own, and I’d love to talk about these outings and these moments where you say you drop everything to be very present with your son to play and explore. Can you paint a picture for me? What sorts of things are you doing together?

Derek:

I don’t have a really interesting answer to that because we just do whatever he wants. I usually just take him outside and follow his lead. He’s the leader. He makes up games and adventures or makes things out of sticks and tape and cardboard, and I just follow along. In New Zealand, I would put him in the car and take him off to nearby forests or beaches every day.

We’re living in Oxford, England now, so we might just head to the local park, or it’s actually a really short, pleasant train ride to London – 50 minutes long. So we often just go to London. It’s just a two-hour train to Paris, so last week I just took him to Paris impromptu. We went to Paris for a few days because why not? [Laughter].

If we’re in a city, it’s the same deal. We also don’t plan anything in the city. We just step outside our door and he leads the way. We turn left or right or whatever way looks interesting, and it’s really cool. He gets really into details. In Paris, I tried to take him to the Louvr,e and he wasn’t interested. He was just like, ”Dad, look at these look these drops of water on this leaf! This is so cool. Oh my god! Puddle!“ [Laughter]. That’s way more interesting to him than the Louvre, you know? So instead of trying to force him into adult stuff, I find it more fun to let him lead the way, and I am there to be his playmate.

John:

That’s so beautiful. In the book, Time Off, there’s a whole deep dive on play. Specifically looking at the child mindset. There is this TED speaker, Alison Gopnik.

Derek:

Alison Gopnik, Yeah.

John:

Her beautiful analogy about how a child has lantern consciousness, and as you age as an adult, you have to manage life, pay taxes, and all these silly things. We develop more of a spotlight consciousness. I like when you sit there and play with your son and follow the lead, you’re sort of following his lantern-like consciousness on these adventures. It’s really beautiful.

When I follow a schedule, the whole day will go by, and I’ll say, ”Wait. I think I woke up this morning and how is it 8:00 p.m. now?“ Whereas when you do things unplanned, time slows down. What about that experience for you? Does it feel like time is slowing down with your son?

Derek:

I know what you’re talking about. There are some days where the day flies by, but there are lots of times where – I’m not supposed to admit this – but sometimes the stuff that he’s interested in, is not as interesting to me. Sometimes he really just wants to build something in the sand for three hours [laughter]. Sometimes that three hours can feel like nine hours, but for the most part, it’s not the time that changes, it’s more like when I’m with him, what changes are the thoughts that are running through my head.

When I’m alone and when I’m working, I’m thinking of myself and my work. All the time. My head is just filled with the thoughts of what I’m working on. When I’m with him, it’s more like meditation. The thoughts of my own self come into my head, but I just immediately just let them drift back out again, and keep my attention back on him.

I aim to stay fully engaged in his reality and see things through his eyes. I’m no expert on meditation, but from what I know about it, it’s that constant reminder where you focus on the breath. Thoughts will come into your head, just let them go back out again. Go back to focusing on the ground.

So to me, it’s “Focus on the kid.” [Laughter]. Thoughts will come in and let them go back out again. “Focus on the kid.” I like it, though. It’s peaceful.

John:

Everyone has their preferred methods, and I like that you’ve added a new one. I’m sort of method agnostic. I’m like, hey, if you’re getting to inner peace, centering, inner clarity that you mentioned, or any sort of focus – whether you’re washing dishes, or building a sandcastle with your son, good on you. That’s sort of meditating as far as I define it.

Derek:

I like that. It’s funny, I just realized today that when I walk, I get ideas. I can think and let my mind roam and just focus on whatever. But when I bike, I can’t think of anything else while I’m cycling. Maybe because it’s just faster and more intense, and I’m usually cycling in a city. There’s no time to think of anything else. I’ve heard some people that are rock climbers say that there’s no time to focus on anything but your next grip or focusing on your fingertips.

I’m thinking now about the difference between choosing an activity where you can do something mellow – maybe you’re chopping vegetables and thinking. It doesn’t require that much thought to chop a vegetable, or it doesn’t require that much thought to walk down the street or walk down a trail, but there are some things that do require your full attention. You might choose an activity like walking or cycling based on whether you’re in need of some more thought or in need of shutting off your thoughts.

John:

Beautifully said. You mentioned that there has been a period recently that you were on a semi-sabbatical and that really got my attention. The emphasis on ”semi“ for the last six years, give or take. What were you doing? What did the semi-sabbatical involve? I’m curious. What did that do for you?

Derek:

When my son was 6 months old and I said, ”You know what? No, I don’t want this distracted upbringing. I just want to give him my full attention for the next five or six years.“ I got that idea from John Lennon, by the way. I remember I was a Beatles fan when I was a teenager, and I remember hearing that John Lennon had two kids. His first kid, Julian, was born at the height of Beatlemania, so he spent no time with Julian. Then when he was around 35, he had his second kid, Sean. He said this time, ”I’m just going to stop everything and give him my full attention.“ He told his agent, ”The answer is no to everything.“

He just disappeared for five years, and he was just a full-time dad for the first five years of his son’s life. I remember making a little note when I was a teenager and thought, ”Yeah, that’s a cool way to do it. I think if I ever have a kid someday I’ll do the same thing.“

When my kid was born, like I said, I was super distracted. I was living in Singapore and saying yes to everything. Then I just said, ”No, I just want to do the John Lennon thing and just disappear for five years.“

I say semi-sabbatical because of what I said earlier. I was still online, but I shut down everything I was doing. No more projects. I had a book publishing project I was doing. I shut that down. I just really wanted to give him all of my possible time. That’s why I say semi-sabbatical, because when he was asleep or with his mom, then I’d be online working. So I wasn’t that cut off. I was a part-time sabbatical.

I also started considering myself retired when people would say, what do you do? Well, I’m retired for now. But I mean, the truth is, I was still writing a book, I was answering emails, I was learning a new programming language, and stuff like that.

John:

So in the semi-parts where it was more sabbatical-like, what did that provide you?

Derek:

The meditation effect. We said a few minutes ago where I was just really, really focused on him. Also, because we were in New Zealand. When I wrote one thing on my blog once about my approach to parenting, some people said, ”Oh, I find it tough to give my kid that kind of attention and not be distracted. It all depends on where you are. If I was sitting in a living room in my house in Iowa and my kid’s sitting there playing with Legos, I’m at home with all of the distractions there.

Then, I might find that hard, too, but I took him out every possible chance. Anytime it was time to play. I really wanted to raise a kid in nature. We moved to New Zealand when he was nine months old, so as soon as we arrived, just anytime I was on duty, I said, “Let’s go out!”

We’d go out to the beaches, or the forests, or the fields, or the rivers, and I just got so connected with both nature and place. I grew up in America entirely until the age of 40, but I have never felt as connected to a country before, as I do to New Zealand. All the plants, and birds, and sounds, and smells. When I counted up, I multiplied how many hours a week I usually spent taking him out to play, multiplied by 52 weeks, multiplied by the six years I was there. I realized that it was about 9,000 hours I spent in those six years just outside in nature with him. I thought, “Whoa, 9,000 hours.” Remember the Anders Ericsson rule?

John:

The 10,000 hour rule?

Derek:

Yeah, the 10,000 hour rule about skill mastery.

John:

So you’re a master of Nature Dad?

Derek:

Almost [laughter].

I thought, ”Wow. No wonder I feel so connected to that place. I spent 9,000 hours just in the forests, and beaches, and fields of New Zealand. I got to know every bird, every kind of moss, plant, and fern. New Zealand feels like my true home now because I just gave it my full attention like that.

John:

I was having dinner last night, and New Zealand came up as a shared desire of some of the people I was having dinner with. We all wanted to go and plan a hiking trip. It sounds so heavenly, and you left there?

Derek:

Before you consider it too heavenly, I have to say, while I was living there, I would often tell my friends – especially friends that lived in America – that would say, “Oh I want to come visit” – I did go visit there once in 2004, years before I moved there. The total cost of a two-week trip, including airfare, hotels, and some various activities, was around $12,000. It’s furiously expensive to get all the way there, and once you’re there, things cost about twice what they do in America. All in all, it’s not that different from Oregon, or Vermont, or Montana.

Don’t go spend $10,000 to go to New Zealand if you haven’t been to Montana or Oregon or Vermont yet. It’s not that different. It’s amazing that you can get on a plane for 16 hours and you get out of the plane and it looks like you haven’t left. It looks almost the same. I tell my friends if you want to get a good bang for your travel buck, go to India. Go to Japan. Go to Russia. Go to Thailand. Go to China. Get a real bang for your buck. Don’t just go to an alternate Oregon. So that said, it’s a great place to live. I always tell people, don’t bother visiting, but if you want to raise a kid somewhere, hell yeah.

John:

You mentioned previously, it became home for you, and you recently uprooted from there to move to Oxford. What led to that? I’m curious. Was there a significant moment or thought process that led you to make that, I assume, difficult decision?

Derek:

I just wanted my kid to experience different cultures. I wanted him to grow up in Singapore, but his mom said no [laughter]. We agreed on Oxford, England. He had only been in New Zealand his whole life. I wanted him to experience different languages, different ways of living, different cultures.

Personally, I was ready to be around ambitious people again. Because a lot of my friends are very accomplished and famous, or whatever, compared to my super, super hyper-ambitious friends, I feel like a slacker. So I started to define myself a bit as an unambitious slacker, but then I realized it was all relative because compared to everybody else around me, I’m almost off the chart ambitious.

I was missing being around ambitious people again. I was feeling ready to end my semi-sabbatical. I was looking to get back into the game again, whatever that game may be. That’s why I was ready to leave New Zealand now, but leaving New Zealand, to me, was like tearing a baby from its mother. I didn’t just cry, but I sobbed many times my last week there.

Often if I’m talking to somebody from New Zealand or somebody asks me that question. So what did you love about New Zealand? I’ll start crying when I talk about it. It really affected me in a big way. That was really hard to leave, but it was the right thing to do for now. I do consider it my long-term home, and I will go back there.

John:

Derek, one thing I really appreciate throughout your body of work, and I assume your programming, in your book, Anything You Want, and your business methodology, is this concept of subtracting. Less is more. I wanted to know, as someone who is a great example of living a life, you’ve made a lot of really important decisions to subtract. Which ones? Do you have one to three significant subtractions that you’ve made that have led to a significant inner peace or maybe success for you?

Derek:

I don’t know about success, but it’s funny, I wonder if it’s even a different thing? I heard somebody once say there was some book somewhere that said you can’t shrink your way to success. I still ponder that sometimes. As far as peace or effectiveness?

John:

Yeah. Effectiveness or inner peace. I think inner peace is one of the things I’m most interested in because, in my network, there are so many people that come to me overwhelmed.

Derek:

Right.

John:

They have a lot of abundance, but not a lot of inner peace.

Derek:

OK, so the core idea: I wrote an article on my site about this. I usually try to give these things memorable URLs so I can just say them off the top of my head. So it’s sivers.org/subtract. The core idea is that when we want to make a change in our life, we often think that we need to add something to get where we want to be.

We say, “OK, I’m here. I want to be there. What do I need to do, or what tool can I use, or what techniques can I use to get to where I want to be? What information do I need to get me there?”

The common thread of all those things I just said is there’s some form of adding. I need more information, more techniques, more space, more time, more this, or more that. But, it takes a while to realize that often subtracting something that’s already in your life is the better solution to get you where you want to be.

If you think you need to add a vacation to your life, maybe instead what you need is to subtract your interactions with a particularly stressful person that’s causing you these feelings of thinking that you need a vacation. Maybe there’s actually a person you need to remove from your life and suddenly you don’t need a vacation anymore. You just needed to subtract that person.

Or if you think you need to add more hours to the day, maybe instead you need to do is subtract all of these distractions and procrastination and find a way of just getting straight into what you need to do, minus the obstacles. Or if you need to add more space to your life, maybe what you need is to subtract your stuff.

Here’s one that came up for me. Just a few weeks ago, I had so many things I wanted to do. It felt like I never had enough time. I wanted to make music, and learn a language, and build a bicycle, and build a mobile app. I’ve never made a mobile app before. I’m living in England now. Oh, my god I want to travel around Europe. I have a list of 49 places I want to go to. I had a dozen more things like that. I was freaking myself out going, “I want to do all of these things!”

Most importantly, desperately, passionately, more than anything, I really wanted to finish writing my next book. That felt like a dilemma to me. I really do want to finish writing my next book. That is the most super important thing, but I also really want to make music, and I really want to learn a language, and I really want to build a bicycle, and all these other things. I was trying to find ways to add more time. I was actually getting resentful of anybody that was taking a single minute of my time. I was getting irritable and like you said, feeling overwhelmed and burnt out.

After a long time of feeling this pain, I decided to take a new look at it. One morning, I woke up and I looked at these two guitars that had been sitting there for a long time and this music recording equipment that I had bought long ago that was sitting there beckoning me every single day, and every single day I was feeling guilty because I wasn’t using it.

I looked at it all and I thought, “Three hours spent making music is three hours I could be spending on my book, or learning something new, or doing these other things I want to do.” Once I heard myself in that thought process, I thought, “Wow. This is something I need to subtract. I need to get rid of this.“ Weirdly enough, that just felt like the right answer right away.

That same day I called up a musician friend of mine here in Oxford, and I said, ”Dude could you use a couple more guitars?“

John:

Sweet!

Derek:

He was like ”Oh my god!“

I said, ”How about a synth? Do you need a synth?“

He’s like, ”Yes! Oh, my god. That synth of yours? That’s my dream synth. You seriously don’t want it?“

I said, ”No, dude. It would actually make me really happy if you would use it. In fact, here, you want my speakers?“

He was like, ”YES!“

So, I just gave him everything. He’s thrilled. He’s a professional musician, and he’s using it every single day. Whereas I had that stuff sitting here for nine months just looking at me. Making me feel guilty.

I gave away all of my music equipment, and the meaning behind that is that I gave up on making music. I have now removed that from my self-identity, from my list of things that I tell myself I’m going to do. Then I looked around at more stuff, like this idea of building a bicycle. I thought, ”You know what? I think that’s one of those things in theory, rather than in practice things where I like the idea of it, but come on.

In the big picture, how much of that is going to improve my life versus finishing my book? No, finishing my book could make a huge difference in my life. Building my own bicycle? Where did I get that idea? OK. I’m letting go of that one.

Then something like making the mobile app? I don’t need to delete that. That’s just an idea, but I’m going to think of it in a new way. I’m just filing that whole thing away. Literally putting it in a folder on my computer that’s just called “Someday”.

Alright, now that’s filed away. Someday when I feel like making that app, it is now tucked away in a folder called “Someday” with all the research and everything I know about it, but I’m not going to do that now. In fact, it might never happen and I’m totally cool with that.“ Then I went through a few other things that were on my plate. I said, ”Yeah, I don’t really need this either. Yeah, that plan I had to travel around Switzerland? Yeah, maybe, but, time is not infinite. It’s 24 hours a day. We can only do so much.“

I removed all of these things until basically, the only two things left are finishing my book and being with my kid. That’s all I’m doing in my entire life right now. Now, most days I work on my book from 5:00 a.m. to 10:00 p.m.

John:

I like that there is the concept of subtracting physical items to help you focus on what it is you’re actually doing. In your case, literally and physically, you’re subtracting this music equipment, this bike equipment, and just getting back to the core essentials.

I’m interested, Derek, in subtracting also knowledge or subtracting strongly held beliefs, which is all under the theme of unlearning, which you’ve written about. I had a whole podcast episode with Kevin Kelly about learning how to unlearn being a crucial meta-skill. I really want to know what you’re learning right now and therefore, what are you having to unlearn to be successful in learning those things?

Derek:

The most obvious example for me recently was starting to look into the music business again after 10 years gone. For those of you listening, I had a long history in the music business. It was basically my entire life from the age of 14 until 38.

It was my sole focus. My every waking thought was music. From the age of 14 to 29, I was a professional musician, and from 29 to 38, running CDBaby.com. It was my everything. My whole world. I read every single book having to do with the music business. I just knew everything about it. I was deep in the game.

Then in 2008, I sold CD Baby and had to look the other way for 10 years. I just wanted to have nothing to do with the music industry for 10 years. Now it’s been 11 years, and it was so weird to me to turn my attention back to it and find out that everything I knew for so many years is now completely wrong.

To even think that I know anything about the music business, or have any kind of authority on it at all, clouds my thinking. That’s my most obvious example where I had to deliberately unlearn all the stuff that I knew was true.

Even how you get a gig? How do you sell music? [Laughter] Sell music? Does that happen anymore? It was weird to blink and realize people don’t even sell music anymore. That’s a core concept that’s gone.

John:

Wow.

Derek:

Then, there are tiny little nerdy examples in technology. If I’m learning a new kind of computer programming, like a PostgreSQL database programming, it’s a style of programming called declarative, or thinking about learning the Elixir programming language. That would be a kind of programming called functional programming that’s opposite from the object-oriented programming I learned is with Ruby language.

That’s something where you have to unlearn your way of doing things and just say, ”OK, everything you knew about that way is wrong. You have to forget that because it’s a completely different way of doing things here. Another tech example is when you think about things just 10 years ago, I would have needed a powerful computer to do music recording. If you wanted to run a digital recording studio, you’d have to get a pretty powerful computer. But now, you realize that a little mobile phone or iPad can do everything you need.

Those little changes require unlearning. You think you know something about the way the world is, and you’ve been stating it’s a fact for a while. Then you catch yourself one day stating something is a fact and going, “Oh wait. Actually, that’s not true anymore. I can’t just paint over that.”

It’s like when you see those old walls that are 50 years old and people have put eight different kinds of wallpaper on top of the old wallpaper? You can’t just wallpaper over what you know, you have to scrape off the old and make sure you really understand that that’s not true anymore. That you learned that at a time when it was true for a while, but that is not true anymore.

Lastly, another example are some cultural things. I grew up in America, was born in California, grew up in Chicago, Boston, and New York. Then I moved to Singapore at the age of 40 and met a lot of Singaporeans that would say to me, “Well I really wanted to be a musician, but my parents wanted me to get a law degree. So I’m a lawyer now, and I don’t make music anymore.”

I’d think, “No, no, that’s wrong. You have to follow your dreams. Do what you want!”

I spent my first year in Singapore feeling like that. Everytime, I heard that story – because I heard that same kind of story over and over again from Singaporeans, I would think, “No! That’s wrong.” It took me about a year as I did more listening than talking to realize that no, this belief of mine that what you personally want is the most important thing, that’s just my American individualism belief. That’s just the culture I grew up in. It’s not a true fact of physics, or nature [laughter].

It’s just one way of looking at the world, but the more Confucian style way of looking at things, that a lot of my Singaporean friends were raised in, is equally valid. It’s an opposite, but an equally valid way of looking at things, which is that what’s best is what’s best for your group, your family, your neighborhood, your country. That’s what’s best.

What you personally want? That doesn’t matter so much. Almost like the meditation metaphor we used earlier, where wants and desires just come and go. You want to be a poet or you want to be a musician. You can let the thought come and then let it go right back out again because you do what’s best for your community [laughter]. I felt like I really had to unlearn what I thought was objectively right and wrong. Then I’d say, “OK, this one way of looking at things is equally right.”

John:

Do you think it’s in your writing, in your walking that you mentioned earlier, where you have this moment of detachment, or the unlearning sequence begins? Is there a common practice where you think you’ve unlearned the most? Maybe not. I’m just curious. I don’t even have an answer for that myself yet.

Derek:

The moment usually comes when I open my mouth and say something, and I hear myself say something out loud that I know isn’t true anymore, and I suddenly realize, “Oh, wow I’m full of shit. I just basically lied by accident.”

Maybe I feel a little extra bad about it just because I’ve had some success. Some people look up to me as some kind of authority. Then when I say something – like the music business examples I said before – when I said something that used to be true in 2000 and it’s not true anymore in 2019, I think, “Oh I just opened my mouth and sounded like a complete idiot because that’s just not true anymore. I’m going to shut up now.”

It usually comes in those moments where I catch myself saying something out loud and I think, “Yeah that’s wrong. I need to shut up and never say that again because it’s not true anymore. I’m echoing something that used to be true.” But then we could get into a whole thing because sometimes that happens with personal preferences too. You catch yourself saying, “I like tea, not coffee.”

Then you have to go, “Hmm is that still true? Do I really? I mean, I did. I’ve been saying that for years. Do I actively like tea or am I just still saying that out of reflex? Do I really not like this food anymore and still like that food? Huh. That used to be true.”

John:

I like that. It’s a moment of awareness of your reflex. That’s when mine happens as well. Whether I’m just regurgitating something I’ve said and it usually gets a typical response.

Derek:

Right!

John:

Whereas I don’t actually have that strongly held belief anymore.

Derek:

That’s why we call it a knee jerk reaction. I think that’s supposed to reference that moment where the doctor hits under your kneecap with the hammer and your right leg just jerks automatically. Somebody brings up a subject or asks you a question and your mouth says the thing that’s your automatic reaction. Then you hear yourself say it out loud and go, “Oh, that’s not true anymore. Whoops.”

John:

You have an article, again for listeners: it’s sivers.org/relax

I really like that. That’s at the heart of what I’m hoping Time Off, as a book and podcast, helps people do. To find out their own rest ethic so they can relax more. You can still be very active. You can still work very hard, but you can do so in a relaxing way. That article really helped me think about this concept of slow is smooth, and smooth ends up being sustainably fast and you can actually see something through. In that article, you mention a bike ride where you had an “aha” moment around realizing this smooth, lesser effort. Do you mind sharing a bit about that?

Derek:

Sure. I was living in Santa Monica, California, which is right on the beach. Not just the beach, but on that beach, there’s this 15 mile stretch on the Santa Monica beach where there are two different paths, one for pedestrians, one just for bikes. It’s an amazing place to hop on your bicycle and go on a 15-mile ride. It’s completely flat and the weather in Santa Monica is always about the same. They don’t really do the whole four seasons thing there.

My bike ride was my main form of exercise. I’d sit there writing and programming all day long, and at some point every day I’d stand up and say, “Alright I’ve been sitting down too long. I’m gonna go on a bike ride.”

I would give it my all. I physically like the feeling of pushing as hard as I can. I’d get on my bike and go as fast as I can. I’d usually do it in the middle of the afternoon when it wasn’t crowded. I would push, push, push as hard as I could and I’d time myself. I’d start my little stopwatch as soon as I hit the beginning of the bike path and I would go as fast as I could. Always the exact same 15-mile loop, and when I was done, I would look at the timer and it was always 43 minutes. I was like, “OK. that seems to be my max effort. No matter what I do, it’s always 43 minutes.”

I would always come home exhausted. It was an intense 43 minutes. My face was bright red, and I was panting. I was exhausted. I’d get home and I’d have to lie down and do nothing for 45 minutes and then take a shower. Then I’d go back to my day two hours after I left. I had been doing this for a number of months and I noticed that I was less inclined, less desiring of going on this bike ride because every time I did it, I was just absolutely flat out exhausted. So one day I said, “You know what? I don’t have to push that hard. I’m going to go on the same bike ride today but I am just going to chill. I’m gonna go at 50 percent.

I’m just going to relax and pedal like a little ride through the countryside. So I get on my bike and I chill. I was sitting upright. I was looking around. Saw some dolphins jumping in the waves and thought, ”Whoa dolphins!“

There’s this part in Marina del Rey, where there are always pelicans on the rocks. Some pelicans flew over my head and thought, ”Whoa, pelicans!“ I go on this same 15-mile bike ride and I had set my timer because I was curious. I was thinking, ”Am I at an hour and a half? Did I double my time? What is it?“

I looked at the timer when I was done, and it said 45 minutes. I thought, ”Wait, what? Hold on. It usually takes 43 minutes. Now it took 45 minutes? How could that be? I was totally chillin’. How could it be that all of that relaxing added just two minutes?“ Apparently, all of that exhausting I had been doing gave me a 4% boost, which is just ridiculous. It was embarrassing to think about.

I thought, ”Wait a second. I could just take it easy and chill and get 96% of the results. One way leaves me exhausted and the other way leaves me rejuvenated. I’m like, “Wow, this blew my mind.”

It made me think metaphorically about all the other times in life when we stress out about something or drive ourselves to exhaustion. So I just try to remember that bike ride and try dialing back my effort by 50%.

We admire those people that just seem to do that as their nature. A few weeks ago, I saw the new Quentin Tarantino movie, Once Upon a Time in Hollywood. Not a great movie, but I’m thinking about Brad Pitt who plays this guy that’s just like, “Yeah, man. Alright, whatever.”

He doesn’t give anything too much effort. We admire those people that don’t seem to put too much effort into anything, and you know what? It all gets done anyway. Maybe 20 seconds longer than people who are stressed out about it, but it gets done. It’s fine.

John:

I like that. I’ve been looking at that in the context of exercise. There’s this concept called “The Flow Zone”, which is a basic XY chart. You essentially want your effort to be above boredom so that you’re still active, but it’s under anxiety, which is the huffing and puffing red face. If you find that zone, as your story just showed us, you not only enjoy it, but you’re more likely to continue the next day, or at a higher frequency. Operating in that zone allows you to have a higher volume over time. Then in the case of exercise, forming a healthy habit.

Derek:

Interesting.

John:

Versus blasting it all out at a class that you’re not prepared for. Not only are you filled with anxiety, but you’re super sore.

Derek:

Right.

John:

And not looking forward to it the next day because you’re so sore. Are there any other activities besides bike riding that you apply this concept of dialing back your efforts by 50 percent?

Derek:

Parenting. I want very badly to be the best possible parent and to give my kid the best possible childhood. Sometimes I get intense about that. Despite what I said earlier about generally following his lead, there are other things I do when I’m not around him. Even just thought processes I go through about wanting to give him a great childhood and be a great parent. But sometimes I just get exhausted. Sometimes I’ll wake up and I didn’t get enough sleep or something.

I feel bad, and I think “Oh, god, I’m not at my fullest self today.” Sometimes I just say, “How about we just sit on the couch and watch YouTube?” [Laughter].

Then I feel bad about saying that. I think I’m a bad dad for just watching YouTube on the couch. But almost every time we’ve ever done that, those times are also wonderful and sweet and affectionate. We’re sitting there cuddling and watching YouTube, and he’s showing me what he likes and we’re laughing and bonding. I think, “OK, parenting is probably something where I could dial it back 50 percent and then get almost the same result.”

John:

I have my own take on Tim Ferriss’ billboard question, which I’m sure he asked you the interview did with him. Mine has to do with a push notification. So just as widely seen but on a digital device. If I gave you the ability to send a push notification on everyone’s phones, what message would you like for people to see on their lock screen?

Derek:

Hmm. If I had to do it and it could literally just be a message, [laughter] here’s the very un-John Fitch answer. The very opposite of this podcast, it’s something I wrote on the back of my notebook when I was at Berklee School of Music, which is a quote, I think it’s a martial arts quote from somewhere. I loved it. It said, “Whenever you are not practicing, someone somewhere else is practicing and when you meet him, he will win.”

[Laughter] I was like, “Must be practicing at all times! 4:00 a.m., get up! Must practice! Midnight, must practice!” I drove myself to the grave, but that comes to mind.

Something else I’ve been thinking of is a helpful saying that stopped me in my tracks recently. It was something like doing what you want now versus what you want most. Very often we think in terms of, “What do I want now? What do I feel like doing now?”

It should be, what do you want most? That is a great distinction.

John:

That’s a great prompt.

Derek:

If I really could go beyond your question and put a message and a feature on the phone, then if I’m going to be a real bully about this, the message would say, “Sorry, closed. Back tomorrow.”

Like a business when you go to a shop when they close at 5:00 and you get there at 5:10, the sign says, “Closed. Come back tomorrow.”

I like the idea of our phone. This device that we think of as our little slave. Can you imagine if it had a mind of its own? It was just like, “Eh, closed. Back tomorrow. I’ll open again at 9:00 a.m. tomorrow,” and your phone would close down and wouldn’t open until tomorrow at 9:00 a.m.

You just have to go, “Oh. Um. . . oh well. OK, I guess I’ll use it after nine o’clock tomorrow. There’s nothing I can do.”

John:

[Laughter] Have a good rest. That’s brilliant.

A few more things I want to talk about. First, as you’ve traveled a lot. Is there somewhere you want to travel to that you haven’t been to yet?

Derek:

Everywhere. I mean, almost everywhere. But more for education than pleasure. I noticed that, at least at this phase of my life, maybe because I just spent seven years in the paradise of New Zealand, I’m not looking for a hedonistic, visceral, look at the pretty mountains trip. I want to learn. I think often about the difference between deep happy and shallow happy.

Shallow happy is having an ice cream. Deep happy is following your exercise schedule [laughter]. It may not be like, “Weeee fun,” but ultimately, it makes you happier in a deeper way than eating the ice cream.

I really want to understand the different world views, the different living philosophies of the world. I’d like to understand why Norwegians are like this. The Spanish are like that. The Italians are like this. Then places that I don’t know anything about at all. I’d like to understand Slovenia, Slovakia, Azerbaijan, and Estonia. These places are a mystery to me. I’d like to go have them not be a mystery. I’d like to understand these places better.

John:

That’s beautiful. Again, this whole concept of going to, rather than going away from.

Derek:

Oh, yeah.

John:

You’re going deep into study rather than escapism.

Derek:

The thing I said earlier about these subtracting, subtraction, subtracting. No, there’s nothing I’m looking to escape. My life is just the way I want it. [Laughter] I got rid of everything that wasn’t. I stripped it all down.

John:

I like that there was a solid consideration of this not being relevant since you do enjoy your work. You read to it being me-time. You also mentioned to me that it’s play. I was going to ask what your next scheduled activity of intentional rest is, but [laughter] for you, it may not look like what rest for most people is. I think that’s OK and fine, and I’d like for you to elaborate on that. You’re sort of the opposite in terms of intentional rest – as in, I’m going to not do anything.

Derek:

Right. Last year, I was seeing this woman who is like an Olympic athlete. Part of what was super appealing when I first met her, we met randomly and started talking, was when I said something about hanging out. She said in her French accent, “Hanging out? Is this when people sit on couches? I do not do this. I do not sit on couches, I do not hang out.”

I was like, “Ohhhh,” and my heart swelled.

I love this idea of, “I do not sit on the couches and do nothing. My life is short. I have much I want to do.”

My friends just roll their eyes at me. I’ve always been intense. Ever since I was 14 and I decided I wanted to be a famous rockstar. I’ve always been super, super, super intense. Except for a brief period of two years from the ages of 19 to 22 where I had a job for three years.

Except for that, everything I do, all of my intensity, is doing exactly what I want to do. For example, my kid is out of town right now. He and his mom are traveling. Now that he’s out of town, I get up at 4:30 or 5:00 in the morning and immediately like within five minutes, I’m writing.

I write from 5:00 a.m. until 11 p.m. every day. I take maybe three little 10-minute breaks to eat, but that’s it. Or maybe I’ll stop if a friend calls, like this call right here. I’m not writing right now. But other than that, I’m working every possible moment.

I realized recently that I’ve been using the word “work” for years. I tell people I need to work. I’m working. People would always say, “God, you’re always working.”

I thought, “Hold on. Maybe we need a better word for this.” I picked the word “work” because it’s the socially acceptable term. When I thought about it and asked myself, what is the real definition of what I’m doing? It’s me-time.

It’s me doing what I want to do most. Speaking of that message to show on somebody’s phone. What you want to do now vs. what do you want to do most? Me-time is about doing what I want to do most. I think of it as more fun than fun.

John:

[Laughter]

Derek:

Again, deep happy versus shallow happy. Shallow fun might be watching a movie, but then ultimately, that’s like the ice cream. I kind of regret it. The movie was alright, but that’s two hours I could have been spending doing something that I want most instead of just want now. For me, finishing my book or even preparing for this interview. So when you said, “Let’s have this call.” I said, “OK,” and I spent probably two hours thinking and writing in preparation for our call.

After we’re done, I’m going to get back to programming a PostgreSQL database, for a shopping cart I’m making to put on my site so I can sell my books directly from my site instead of having to rely on Amazon.

This is all play. This is more deeply satisfying than a shallow, happy, hedonistic style of fun because it’s also keeping in line with my beliefs. It’s accomplishing my goals. It’s scratching a years-long itch. Some of the things I’m doing now are things I’ve been wanting to do for years, and they’ve finally moved up the queue. It’s satisfying curiosities or feeling that exciting brain tingle of learning new things, or feeling that great pride of finishing something difficult.

There’s no deeper happiness than setting out to do something difficult and achieving it. That’s the ultimate play. That’s the ultimate reward. That’s the deepest happiness. I wouldn’t call that leisure or rest, but it is play, but I call it work when I’m explaining it to strangers.

It’s almost like when I fly on airplanes and somebody next to me says, “Oh, what do you do?” I used to say I’m a musician, which would lead to 20 follow up questions like, “What kind of music you do? Is it something I can hear?”

I always thought, “Eh, I don’t want to talk to a stranger next to me on a plane.”

Then I found that about 20 years ago I started singing. When people ask, what do you do? I say, “Computer programmer.”

They go, “Oh.”

It’s a wonderful conversation stopper, right?

John:

[Laughter] Yeah.

Derek:

I find the same when I just say, “I’m working. Sorry, I’m busy. I’m working.”

People go, “Oh, OK.” It’s the answer that gets people to just leave you alone. In Steven Pressfield’s books, he talks about doing the work and being a pro. He absolutely calls it work. And a lot of other creative artists say, “This is my work.” If you want to sit down and redefine it, I’m sure that could probably come up with a more accurate word, but it’s OK to just use the word “work” because we’re communicating it to others.

John:

One of the goals I have after the Time Off book is that it feels absolutely necessary to follow it up with Time On, which is diving more into work ethic. There’s plenty of books out there that dance around the concept of work ethic and upgrading your work ethic, whereas I wasn’t able to find a lot for rest ethic and that’s been my focus.

You’ve given me some really good ideas here around this concept of work being play and the me-time concept.

Derek:

You’ve seen Stefan Sagmeister’s talk?

John:

Absolutely. That literally was the nexus of the project.

Derek:

OK good.

John:

We have several profiles in the book and he’s one of the ones that I had to include because that TED Talk woke me up. I ended up taking my own sabbatical.

That was a life-changing event for me and then I became obsessed with sabbaticals. Then that opened up into me asking, “Well what are all these different elements of rest ethic that people do?” Some of them are very active, some are not. There’s just been a fascination with what value lies in rest ethic.

Derek:

There’s a book called The Power of Full Engagement by Jim Loehr and Tony Schwartz. The little blurb I wrote about it said the author worked with the best athletes and executives for years and found out the best ones know how to push themselves, then recuperate, push and recuperate. You take the same approach to your emotional, mental, physical and even spiritual life, and it’s a powerful metaphor.

Think in terms of sprints, not marathons. Be fully in whatever you’re in. Then give time to recuperate, but push further each time past your comfort zone like a good exercise plan.

I know you’re at the finishing of your book in the final editing, but you might want to read The Power of Full Engagement for a little last-minute inspiration.

John:

That would be great. We have a section called “The Future of Work” that we ended on. Our argument is that that ability is important and it’s backed up by a quote from Naval Ravikant, who was the founder of Angel List. He once said that 40 hour work weeks were a relic of the industrial age and that we now live more in a knowledge economy. Knowledge workers function, to your point, like athletes. You train, then you sprint, and then you rest to reassess and repeat.

In the book, Rest, written by Dr. Pang – it’s funny how it comes back full circle to our conversation – you mentioned the 10,000 hour rule. That study was done on a number of dimensions of different types of talent. One was musicians and violin players, specifically. He said what’s not commonly talked about is that that mastery included around 45,000 hours of rest so that the effort could be learned.

Derek:

Nice.

John:

The last question I have for you is, I have friends around me, as well as my mother has been going through some mental health issues, and they’re all correlated to being extremely burned out. In my estimations, it’s from not taking enough rest or solitude, enough me-time. Do you have any words of encouragement for those people out there that right now are feeling really burned out or overwhelmed?

Derek:

I don’t know if anything I could say would help, but there is one story in my past where I was in my final days of running my company 12 years ago, and it was really stressing me out. I was feeling overwhelmed. I was working with a coach at the time. I said, “I have to do this and I have to do that.”

He said, “You don’t have to do anything.”

I said, “Well, yeah. I have to pay my employees. I have to pay my taxes. I have to ship customers orders that they’ve paid for.”

He said, “No, you don’t.”

I said, “Yes, I do! Of course I do! Of course I have to pay my employees and ship the customer’s order.”

He said, “No, you don’t! Look, I’m not just being glib or quippy or trying to be contrary. This is a really important point. You need to really understand this before we talk about anything else. You don’t have to do anything. You could, right now, decide to go lay down in the grass in a park for the next 10 years and do nothing.

Yes, after a while, your employees would stop showing up to work because you were no longer paying them. A couple of them might try to file some kind of small claims lawsuit and you’d get notices in the mail in your mailbox. Maybe you’re not even checking your mail. If you don’t pay your taxes, then in five years the IRS will notice, and they’ll come after you and you’ll have to pay them now with interest.

But there’s a difference. You don’t have to do anything. You just need to understand that if you don’t, there may be consequences and probably less consequences than you think there would be. You really need to make sure at all times that you understand that you’re choosing to do whatever it is you’re doing, but you absolutely don’t have to. You need to understand that difference.”

It’s pretty esoteric, but sometimes I think of that when I’m feeling overwhelmed and I’m like, “I have to do this and I have to do that. . .Oh, wait, I don’t have to. I’m choosing to.”

Some people like to have an accountability buddy. [Laughter] I’m the most terrible accountability buddy. I say no to anybody who asks me to get into any kind of accountability situation with them, because to me, it always comes back to me thinking, “Well, you don’t have to do anything.”

“But we promised each other!”

I’m like “Eh I mean, you don’t have to. I choose to. Maybe I don’t want to anymore.” So I don’t know if that’s useful to anybody.

John:

A lot of that anxiety and overwhelm is a deep belief in trying to manage, so many “have-to’s”.

Derek:

Right. The subtraction process we talked about half an hour ago, it’s really interesting to look at all of these things in your life and realize that you can just quit. Almost all of them, maybe even all of them. All these situations we get ourselves into. So many times in the past, I used to say yes to a lot of conferences and events and people would ask me to speak and I’d say yes. People would ask me to do this and that, and I’d say yes to everything. A couple of times it was just overwhelmingly, not impossible, but. really inconvenient or just really bad for me to follow through and do the thing I said I was going to do and appear at the conference I said I was going to appear at.

There were just a couple of times in my past where I felt horrible about it, but I was like, “Hey, I’m really sorry. I need to cancel. I know I said I was gonna come speak at your conference, but I just can’t.” You could imagine before that phone call happened, I’m sure there were 15 hours of me wrestling and feeling like, “No, but I have to. I said I would. There’s no way I could cancel. I’d be horrified. I’m sure that would mess up their whole event.” It’s so funny that every time I’d get into one of these situations because I think it happened three or four different times.

Each time they would go, “Oh, okay, no problem. Thanks for telling me.”

It was no big deal. My cancellation was a total nothing. It was one of 100 things on their to-do list for the day. They were just like, “Oh, okay, we’ll get a different speaker.”

Whereas I was all wrought and upset about it. It doesn’t matter that I said yes to it. If it’s not working for me, I said yes at a time where I was predicting that it would be good for me, but predictions are usually wrong and now that reality is here in front of us, it looks like I made a wrong prediction. I have no problem saying, “I’m sorry, predicted wrong. I’m sorry this is upsetting.” There have been some big ones in the last couple of years.

I almost bought a house. It was months into the process. The day before I was supposed to send the wire transfer, I said, “You know what? I’m not feeling it anymore. I’m really sorry. I thought I wanted this house, but I don’t.”.

They said, “What? How dare you!”

I said, “Sorry!”

Obligations, events I said I was going to do – there are a lot of these things we’ve said yes to. It’s a little upsetting for the people on the receiving end when you say sorry, “I can’t do it anymore.” There’s actually really good advice in David Allen’s famous Getting Things Done book.

He actually had a follow-up book that hit me a little harder called Ready for Anything where he said that, yes, we should follow through on all of our commitments. The opposite of what I just said. He said anything you’ve committed to doing, make yourself do it because I want you to feel the pain of saying yes to things. Feel the pain so that next time somebody asks you to do something, you’ll remember how painful that was last time you said yes to something. Then you’ll know to say no in the future.

Finish all of your current obligations. Quit the ones that you’re allowed to quit, but the things you said you would do? Finish it up and do it, but remember that pain and do not say yes to things anymore unless you really want it. Which is the subject of my next book, Hell Yeah or No.

John:

[Laughter] That’s a great plug at the absolute last second. I love it.

Speaking of that, was there anything that you wanted to share that I didn’t ask?

Derek:

No [laughter].

John:

Okay. Awesome [laughter]. You mentioned sivers.org.

Is there anywhere else that people can say hello?

Derek:

The local pizzeria. If you happen to be there when I walk in. Say hello.

John:

[Laughter].

Derek:

Sivers.org is probably the best place to find me. You’ll see that I do actually enjoy checking my email. I like it when people introduce themselves and say hello. It makes my inbox a little more interesting when somebody tells me something about themselves and I don’t have to answer a question. I always encourage people to introduce themselves and email and say hello. So go to sivers.org and you’ll see the ’Contact Me’ link.

John:

Awesome, Derek. This has been a real honor for me and I appreciate all the things that you considered. You prepped beautifully for this in such a thoughtful way. I can speak for the audience ahead of time that we’re grateful.

Derek:

Thanks, John.

John:

Thank you so much for listening to that entire conversation. If you made it this far. Thank you very much. I hope after hearing Derek and I talk you have a bit of an upgrade to your perspective and maybe we’ll think more about less, saying no, cultivating more silence and solitude for yourself, and not work so hard so that you get overworked.

Derek and a few other people are covered in the book Time Off, which will be coming out in 2020. The book is going to be fantastic and beautiful. We’re working with a wonderful illustrator, and you can subscribe for updates at timeoffbook.com. Max Frenzel and I have been working hard on the book and we’re super excited to get it into your hands, so check us out online. Have a calm rest of your day. I appreciate your attention.