Derek Sivers

Interviews → Productivityist / Mike Vardy

Why I don’t like holidays, How to Live, how constraints give you more freedom

Date: 2020-05

Download: mp3



I’d like to welcome Derek Sivers to the Productivityist podcast. Derek, thanks for joining me today.


Thanks, Mike. I’ve practiced saying Productivityist a few times before our call today.


[Laughter] You are not the first and you will not be the last. But the other thing that happens is some people end up saying, “Well, thanks, Mark Vardy.”

So they nail saying Productivityist, but then say, “Well, thanks, Mark.”


It’s a good word though. I like it. Productivityist.


I’m an enthusiast about productivity, and I became a specialist and a strategist about it. So we threw the “ist” at the end. I coined it ad hoc on a podcast that I used to co-host. Someone heard me say it, mentioned it in a blog post, and it took on a life of its own.

What’s interesting is I’ve never really said that I’m THE Productivityist. I say that anybody can be a productivityist. Even my old podcast producer said, “I’d like to welcome The Productivityist, Mike Vardy.”, and I said, “I’m not The Productivityist. That’s the name of my company.


Yeah, like people call Debbie Harry, “Blondie.”


That’s true. I mean, it’s a band but you’re right. I guess that’s the way it works.

I want to talk a little bit about one of the books that you’ve been working on as of right now. And it’s a pretty ambitious title. What’s the reason you decided to write this book called How to Live? And what lessons have you’ve learned while writing that book


I often think about other approaches I can take in life.

Sometimes I would create a possible future where I dive down the hole of intellectualism and into the world of ideas and study. I read a book every single day and I study a new culture every month and I learn a new language every year. I’d spend many hours or days writing about that way I could live.

Then I’d take a little walk outside in the forest and I’d think, “No, you know what? No, this is how to live. In nature. It’s just oxygen and life and living.” Ideas are interesting. But, you know, I need to move my legs and breath fresh air and appreciate the nuances of that rotting tree and the curls on this fern. Yeah, this is how to live.

And I’d spend a while thinking that’s the way to go. Then, I’d think, “No, you know what? Travel. Travel is what it’s all about. You got to experience these things. You can’t be in theory. It has to be in practice. You have to go to a place and visually experience it.”

You know what? No, it’s time I start a business. Yeah, creating a business. That’s creating value to the world. That’s giving back to the people.

I could keep going. And so I did.

I spent many years of my life thinking of these possible futures.

So the book How to Live is exploring all these possibilities. I never feel that one thing is right and others are wrong. Instead, I always see it as just another way of looking at things. Like for whatever true thing you believe, the opposite is also likely to be true.

How to Live is very opinionated. Each chapter thinks that it is right and all others are wrong. But the catch is that each chapter has a different perspective, so it disagrees with all the other chapters.

That’s the book, and it’s an absolute blast to write. And what’s cool is it comes to a conclusion. That was actually a total surprise to me. And made me scream with delight when I found the conclusion to all of this, but I’m not going to reveal the conclusion yet.


There’s no right or wrong way. These chapters are warring against each other. And one of the things that you mentioned, you seem to be endlessly curious too. So I’m guessing that writing this book fed that curiosity to a real strong degree.


Curiosity? I guess so.

I guess I have an active mind. I’m 50 now, and it helps that for decades, ever since I was a teenager, I’ve slowly been crafting a life of freedom. Whenever I was given the choice, I moved towards a life of less responsibility and more freedom.

So, I’ve crafted a life where I have lots of free time. I spend hours and hours and hours a day just thinking and writing. Well, actually, just always writing. Thinking is writing. I’m always writing. Pretty much from as soon as I wake up until I go to sleep, I’m doing some form of writing or talking like this. I have very little nil time. I rarely watch movies or shows or videos.

I think one of the lessons learned is that it’s easy to get sucked into believing that one way is right. I do it every time I write a chapter of this book. I’m writing Chapter 7 about delayed gratification. And while writing it, I’m completely convinced that, yeah, you know what? This is truly the best way to live. This is the answer to life. This is how we should all be living.

I get sucked in to believing that this is right and other things are wrong. And I think it’s because we want certainty. And in that mindset, these certain things are right and everything else is wrong. But then it’s also so easy to get into a different mindset if someone shows you a different point of view.

I love those transformation of belief movies. The first one that comes to mind is American History X where somebody believes one thing at the start of the movie very, very strongly, and by the end of the movie, they believe the opposite. I love that. We all do that in our lives.


You’ve worked your way towards more freedom and less responsibility. I’d love to hear you talk a little bit about that because I think some people really need framing and constraints to kind of keep them from going too far off in a direction that they don’t necessarily want to go in. And then they find themselves going how the hell did I get here?


Totally agree. And this is a under discussed subject. I love that you brought this up.

If you’re looking at a blank page, it’s a little daunting to think of what to put there. But if somebody said, “OK, now make me a drawing using only a triangle, this piece of charcoal, and four lines and make something that represents growth or whatever else it is.”

Well, now you’ve been given some guidelines and constraints. That’s somewhat inspiring and maybe even liberating. Ironic because the root of the word liberating is freeing, but sit’s more liberating to have some constraints.

Now, it frees you from the daunting prospect of infinite possibility and reduces it down to a limited possibility that we can comprehend. Same thing with music. If somebody says, “Write me a song about anything, go,” that’s daunting. But if they say, “Write me a song about this using only these three notes but you can never play these two at the same time, go.” Now you’ve been given some creative restraints.

There is a beautiful book called The Listening Book by Walter Mathieu. He said, “Restrictions will set you free.” I love that.

That’s creatively, but in personal life, I felt it when I sold my company. I was single. I was not attached to anywhere. I’m not really into family. I had friends, but they were already spread out around the world and suddenly I had really no responsibilities. And it was overwhelming. It was the blank page syndrome.

I felt like, “Oh, my God, I could go anywhere right now and do anything.” I could go make chessboards in Istanbul. I could move to Chile and start a blueberry farm. [Laughter] I could work on a fishing boat. Oh, my God. The world is so overwhelmingly free. It was paralyzing.

So, I did come to the conclusion that it’s good to have constraints.

You have kids, so you know that it can be amazing and enriching to commit to somebody which is the opposite of freedom. And it can be amazing and enriching to commit to a place and become a part of a community.

People talk about the preppers who are always preparing for the day that disaster strikes. Well, community is what you do when disaster strikes. It’s not about being alone in a bunker in Montana. That’s not a good survival plan. It’s about being an integral part of a community. And that takes commitment and not always being a constant nomad.

So like many things, people find the balance that’s right for them. There’s no right or wrong answer. There’s a spectrum. Some people are really happy having total commitment. They have four kids and three dogs, and they’ve been living in the same house with their spouse for 40 years. That’s their happiness set point. And somebody else might be at the opposite end. You have to find the level of commitment that feels right for you


I’m a big believer in productivity being personal. You wrote about the idea of why time is personal and in fact, as of this recording, it’s the most recent post that I’ve read.

Right now, especially as we’re going through this season of uncertainty, it’s like time is more fluid than it’s ever really been. Can you touch on that piece in particular?


For the audience listening, I wrote a post on New Year’s Eve because I was kind of annoyed that everybody was talking about the “New Year”. Like it’s a big deal that it’s a new year tomorrow. But I felt like today is just a regular old day. And so is tomorrow.

There were times in my life that were massively transformational, where today is different than yesterday because I made a big decision or something big happened. But, you know, December 31st is not one of them. So how weird to celebrate an assigned day. Like on February 14th, you’re supposed to be extra romantic that day?

Then I thought about midnight. I’ve often had discussions with friends about the concept of midnight, where suddenly at 12:01 a.m., they say, “Well, that was yesterday. Now it’s tomorrow.” I say, “No, come on, look outside. Did something change? No.”

What a weird, arbitrary, forced agreed upon lie. That 12:01 is tomorrow and 11:59 was yesterday. If you ignore these man-made clocks, which are a very, very recent invention, and you look outside, nobody would agree that midnight is when it became tomorrow. So I’d argue that it’s when the sun comes up.

I understand we have to have airplanes and trains that schedule and arrive on time. So I understand why it was invented. I’m not arguing that we demolish it. But let’s admit it what it is.

I don’t know how much of this point of view is influenced by the fact that I am quite an introvert. I think I didn’t even realize how much of an introvert I was until I was living in Singapore in Marina Bay. It’s a very central area where they put on events and things like marathon races begin.

People kind of assume that nobody really lives there. But some people live on that square, and I was one of them. I signed a two-year lease, and I regretted it almost right away because I found out that almost every week there was some big, noisy event that started on Sunday at 6am.

What the hell? I’d look out my window and I’d see like a bunch of people with numbers on their chest and a bunch of people with bullhorns yelling and everybody organizing and PA systems and all this fuss and screaming and yelling. And it’d just be like some race going on outside.

I thought, “who would subject themselves to this?” You could have gone on the same 5K run yesterday, and you would have been the only person out here. You could have gone running along the shore. A nice, quiet 5K run. But why would somebody subject themselves to all of this noise. My friend said, “Derek, I think you’re an introvert. Some people like being around other people.” And I went, “Oh, right.”

So some people like getting into Star Wars on the 4th of May or celebrating with hearts and flowers and boxes of chocolates on the 14th of February. And they like getting together with everybody on December 31st to get drunk and silly, nostalgic, or whatever. They like that.

Personally, I like my celebrations to be private.


Well, and I think the interesting thing about that is you can have ebb and flow too.

I start my year on September 1st, but the rest of my family thinks I’m crazy. But they know on the 31st of December, I’ll celebrate with them. But it isn’t completely arbitrary because my kids start the school year in September.


I was just about to ask you if that’s why September 1st because for most of my childhood that felt like the new year. Like the smell of autumn and the fresh pencils and school blocks and the new notebooks and erasers is the beginning of a new year. Yeah, I get it.


I’m not the only one that does this. I think I’m probably a pseudo extrovert. I’ve read, Susan Cains’ Quiet. I used to be far more extroverted, but I think over the years, I’ve kind of pulled back a little bit or I’ve just always been that way and have pushed myself out a little bit.

Martin Short starts his year in September. He does it for the same reason – the school year. Gretchen Rubin mentions that she starts September as well.

What’s interesting is when people listen, to use a Star Wars reference, only a Sith deals in absolutes. [Laughter] I’m not saying you’re a Sith lord, let’s be clear. But I think that what’s interesting is you can pick and choose.

I’m married, but my wife and I don’t really celebrate Valentine’s Day. But my daughter was born the day before Valentine’s Day. She’s got a boyfriend now, so don’t try to combine those gifts. I think having an understanding of that is important. But what’s more important is not to be beholden to them because everybody is. I mean, just because New Year’s Eve for the Gregorian calendar says January 1st doesn’t mean it needs to be that way for you. In fact, for most people, it isn’t. Look at Chinese New Year for crying out loud.

I want to talk a little bit about what gets your attention. The authors that you’ve read, the kind of the edicts that you follow when you first started this journey versus now. Where is your attention shifted? What’s remained the same? I’d love to hear some of that.


I’ll answer it, but first, I think I’ve had many big phases in my life, and the one I’m in now is the 4th big phase. Kind of like saying the beginning of this journey is the beginning of Chapter 4, you know?

I had a whole section of my life where all I wanted to do was to be a famous musician. I was completely monomaniacally focused on that one thing. I did that for 15 years, and then I did nothing but CD Baby for 10 years. And now I think I might be at the tail end or at the end of this 12 years of just kind of exploring and adventuring and lifting my head up and enjoying having no responsibility and feeling very nomadic, like the nomadic explorer.

Sometimes it’s a personal feeling of feeling done with something, but sometimes the world nudges you. So the reason I moved to England last year was to travel my butt off. And now in 2020, I’m having to make a whole new plan and realize that that the reason I’m here is now moot and the idea of traveling is not necessary for what I want. So I’ve had to reevaluate all that.

But you were asking who? So I read Tim Ferris’ 4-Hour Work Week as I was already kind of living it. I was the owner of a company that had 85 employees, and yet I was living across the world, solo. When Tim was talking about delegating all the work and outsourcing your business and all that kind of stuff, I was already kind of living it.

And it’s sweet, actually. I haven’t read it, but I hear that I’m in the 2nd edition of the book. I was such a fan of the 1st edition of the book in 2007, so I contacted Tim. This is amazing. We met up and became friends. But that was a huge influence on me because that was right as I was coming out of 10 years of being monomaniacally focused on running CD Baby. I was just lifting my head up and feeling done with it.

Sure enough, I sold the company the next year. Again, that was nudged from the outside. I just had three good offers in one week to buy the company. I’d been saying no for years, and so I finally said yes. So the world gave me a little nudge through the door that I was already headed out.

Seth Godin is somebody that was very much a guru to me when I was running my company. And as much as he’s still a friend now and I love his podcast, the stuff he talks about isn’t as pertinent to what I’m doing now or interested in now.

But on the other hand, Tyler Cowen has this great podcast called Conversations With Tyler. He’s an economist at George Mason University, and he’s written a bunch of books. His thinking is becoming much more interesting to me. And so is John McWhorter, who is a linguist that I find fascinating.

I’m more into cultural learning than I was before, and I’m taking myself more seriously as a writer. I never called myself a writer before until just a year or two ago. I finally admitted that I’m into writing now.

I’m thinking of myself less as an entrepreneur and more of a writer. So I don’t know. I think you’re catching me at the very end of my fourth phase and ready to start a new one. So sorry. I’m not sure if I gave a good answer.


The reason I asked that question is because when I first started doing this, like I was reading the David Allens and the Stephen Coveys, and all that stuff. And now I’m finding that I’m spending more time looking at, say, the Austin Kleons. I’ve read your work throughout.

And even when I read Seth Godin’s stuff now, a friend of mine said, “You know, not everything Seth writes resonates, but I stay subscribed because every once in a while, there’s something that just hits.” Right?

Cal Newport’s another one who I’ve read for but it’s not for the productivity stuff. It’s for the some of the deeper stuff. So the reason I ask that is because I feel that as you make your way through the stuff you paid attention to earlier, elements of it are still there but now, the horizons have changed. Like you said, there’s different seasons or phases that you’re in.


Actually, let’s stay on this topic for just a second. I was deep in music for 15 years, and I’m not even talking CD Baby. I mean for 15 years from age 14 to 29, I spent every waking moment completely focused on making music. That’s all I did and all I cared about.

And I learned a ton about music. And I was deep into music and I read books about music and I analyzed songs and I broke it apart and just everything. I don’t make music anymore, but I can still appreciate it because that was one of my worlds. I lived there. You know? It’s like a like a physical place that you used to live. I used to live in Chicago, but I haven’t in a long time. But if I read the Chicago news, I’m like, “Ahh, my old neighborhood.” And you can get into it. You know the references you get. Oh, yeah, the hot dogs. I get that. Oh, wow, Comiskey Park, the Navy Pier…

So that’s what I meant about Seth Godin. I only listen to three podcasts, and Akimbo, Seth Godin’s podcast is one of them. I’ll read anything he puts out instantly. I’m still a super fan, but it’s mostly speaking to my Chapter 2. It’s speaking to my previous chapter when I was focused on my business. And now, anything having to do with business customers, marketing, profits, all that stuff, I’ve noticed that my eyes just glaze over, my ears blur when somebody talks about these subjects because it’s just where I used to live.


You’re kind of delighted by it, but there’s different levels of it.

What’s fascinating to me now is that I take that some of the things I’ve learned from comedy or even when I’m watching something like pro wrestling – I’m a fan. I’ll be delighted by it to a degree because there’s certain things that I can see from it and go, oh, does how does that fit now? And if not, I just toss it.

But sometimes it does and I’m like, oh, this is cool. Let me dig deeper into that. Does that still happen for you with music? Like the business stuff. Does that still kind of resonate with you?


I love that we’re talking about this because not only does music still resonate with me but I went to a jazz school. I know a lot about jazz. I know a lot about orchestration. I also know a lot about ’80s metal because that’s what I started in.

And I love these separate interests. But then what I love is continuing to expand these interests into things that, a few months ago, I had no interest in. Just a couple of months ago, out of curiosity, I learned something about men’s suits. I had never had any interest in suits. And suddenly I did. Somebody told me something about Savile Row. I’m living here in Oxford, England and London is just down the road and Savile Row is this interesting road in London with this long history of tailors. I just wanted to learn something about men’s suits and why people get really into it.

And there’s this brilliant guy on YouTube. I’d love it if you could link to him in the show notes. Hugo Jacomet, a French guy with long white hair that talks on YouTube about the sartorial excellence of men’s clothing. And I found it fascinating learning about what a double-breasted versus single-breasted suit communicates and why the peak lapels versus notch lapels and all of this stuff and not doing it for any goal. But it just became a thing that I learned about and now I find interesting.

And so now it’s become a language that I speak a little bit. Like if you learn a little bit of French and now you can recognize when somebody says it’s just a little je ne sais quoi. And ah, I know what that means now. So then there’s the same with Indonesia and now same with dogs. Two years ago, I had no interest in dogs. A year ago, I got interested in dogs. I just learned how to play backgammon two months ago because I went to Istanbul in January and saw that everybody’s into backgammon. And I thought, you know, this is like a 4000-year-old game. There must be something good about it.


It’s been around for a while.


I read a book about backgammon. I got a background and training app and just in that last hour before falling asleep, I started learning backgammon and playing against the computer. I think it’s kind of cool that now I get backgammon. It’s really fun to expand your horizon with these things and understand Chinese opera and understand whatever, the dairy industry.

There’s a great book called Salt, written by the same author of that wrote Cod. So Cod is this masterpiece of a book explaining how the fish cod changed the world. And then later, he wrote the book Salt, explaining how salt changed the world. Looking at the world through the point of view of salt. It’s just so fun to expand your horizons, to understand these things.


I’ve started to look at TikTok because my daughter is really into it. I wanted to understand it and see it to speak her language a bit. I did the same with YouTube too.

One of them happened to be a child actor that my daughter used to watch when she was growing up. And we would watch this show together. His name is Josh Peck. And I’m like, oh, I remember this guy. He used to be on the show and I watched one of his YouTube videos. So I’m starting to explore.

And then all of a sudden at the end of the YouTube video, he goes, “Listen to my podcast called, Oddly Enough.” Coincidentally, I’m curious. I thought, “Oh, he’s probably just talking to YouTubers and his friends.” But no. He’s talking to David Epstein. He’s talking to Malcolm Gladwell. He’s talking all of these people that I’m interested in. So it broke my impression.

You’ve talked about these monthly self-expansion projects. But I think it’s also not just not just themes or topics of interest, but people of interest that I’m finding, especially right now with this lack of connection that we are experiencing since we can’t see people as easily. That’s something I’ve been leaning into and I’ve been fascinated by as well.


I love it. Yeah. Thank you for bringing that up. It’s so fascinating and that especially the TikTok example and that guy. That’s such a great example.


I’m going to talk about the productivity stuff to a degree, but I’m going to have fun doing it which is something that I think people can lose sight of a bit when they are so wrapped up in being productive. They lose the joy and fun.

This has got to be fun for you right now, just this season in particular, has it always been that way? Because when I’ve followed your work, you always seem like you’re having a lot of fun.


What do you mean about this season?


This phase in your life right now? You just finished talking about different chapters of your life.


Yeah, that’s the reason I do things. Back when I was an aspiring musician, I wasn’t having as much fun. There was a lot of anguish, I was trying very hard to be famous and living in, you know, swimming in the pool of rejection every single day. So that was a bit of a drag.

But I was free and I was a full-time musician. I bought my house with the money I made making music. I was kind of living the dream, even though it was a difficult struggle.

CD Baby was just fun. That was a blast. It got to be a real drag at the end when I had too many employees and too many employee issues. But that’s why I left. And then everything since then, of course, has been just doing whatever seems interesting.

I don’t do something if it’s not fun and that’s a wonderful luxury to have. And sometimes people criticize me for that luxury or give the whole kind of yeah, easy for you to say, you’re rich kind-of-thing. But I was like this in my 20’s, too, when I had, $12,000 dollars in the bank, and that was enough for me,. I’ve always just found a way to live on very little so that I don’t have to do things I don’t want to do.


As we get close to wrapping up, I want to talk about something that might not be fun for a lot of people. And that’s email, especially when they hear the numbers I’m going to throw at them right now. You recently wrote, as we’re recording this talk, “I have answered 2100 emails in the last 48 hours. 4000 left. This is intense, but I’m thankful for the connection.”

So what led to this particular period where you said, “I’m answering this many emails?” That was that was a deliberate choice. Is that something that you do regularly? What is your relationship like with the email? Because I think a lot of people struggle with that.


Sure. There’s a famous quote that many writers have said, which is, “I hate writing, but I love having written.” So, I don’t love emailing, but I love having emailed. On the other hand, I don’t hate emailing. I mean, it takes time and it’s emotionally draining, but so is socializing.

You know, if you were going to lots of parties or meeting with lots of people or lots of events or lots of conferences, it is draining, but it’s worth it for the people you meet. You would walk away from that having connected with lots of people and have a great network of people you now know.

So that’s what my inbox is. To me, it’s way more efficient than flying across the world to attend an event in person or way more efficient than meeting up one-on-one, face-to-face with four different people a day. Instead, I can plow through 500 emails per day. And it’s a little connection, but I’m OK with that.

But then there’s also the fact that many of my good friends and even great loves of my life have started as a stranger in my email inbox, so I get a huge sense of security from all the people I know in the world. It feels wonderful to me that I could go to Ghana and look up in my database from my past emails. Who do I know in Ghana? Alright, I know 12 people in Ghana, and I can email them and say, “Hey, I’m in Ghana, can you meet up?” And that’s such a great feeling.

That 12 strangers from Ghana who have reached out to me. And I replied. We’ve got a kind of reciprocity going on. It’s a loose connection, but it’s there to potentially turn into a deeper connection. And yeah, like I said, a few have turned into the deepest possible connection.

And lastly, let’s admit it, emailing can be a wonderful way to procrastinate when the other option is doing some really hard work, whether that’s hard emotional work or hard intellectual work. It can be nice to just revert to the email inbox and just do that. So I enjoy it for all of these reasons. It’s difficult, but it’s worth it. And wherever I am in the world, I find it pretty amazing that I can be sitting in one spot with my cup of tea connecting with hundreds of people from all around the world in different walks of life.

And actually, I love that I don’t know how old people are and what they look like. Sometimes, I don’t even know the gender. I can’t tell by the name. That’s really cool. I like that we can just have these little conversations without any of the prejudices of age or gender or race or whatever. You know, it’s like, I don’t know, I just all around love it. So, yeah, as you can tell, audience, you should you should email me and say hello and introduce yourself.


Derek, it’s been a great connection today. I really do appreciate taking the time. Where can people email you and then where can they keep up with what you’re doing right now?


Just go to, my website. My email address is there. So email me and introduce yourself and say hello.


Derek, thank you so much for joining me today on The Productivityist Podcast.


Thanks, Mike.