Derek Sivers

Interviews → Pausecast / Rachel O’Meara

A guided pause, living life as a series of grand experiments, asking yourself questions, possible futures, and the Muppets

Date: 2020-04

Download: mp3



Hi, I’m Rachel O’Meara, author of Pause: Harnessing the Life-Changing Power of Giving Yourself a Break.

Welcome and thank you so much for joining me today on the podcast. I am here with a very special guest, Derek Sivers.

Hi, Derek. How you doing today?


Hi Rachel. Thanks for having me.


So glad that you’re here. For those of you who don’t know Derek, I want to share a little bit about him.

Derek has been a musician, a producer, a circus performer, entrepreneur, Ted Speaker and book publisher. And I know you’re already working on your latest book, which we’ll talk about.

You were the founder of CD Baby and being a double clicker. I see you as a thought leader by contributing to how to shape and influence society, how we think about ourselves, and in the music world. I have a lot of respect for you.

You have a podcast as well. And you endorsed my book, Pause. I’m always grateful for that.

Your YouTube video called the First Follower has always stood out to me. I’ve seen that in so many trainings. I use it myself. People still talk about it today.

It’s so nice to have you here.


Thank you. Likewise. I’ve spent a few hours of my life reading your words and a few hours of my life listening to your show. It’s good to finally speak with you live.


This is the first time you and I are speaking live. We’ve had many email conversations. It’s lovely to communicate in this new way.

I wanted to invite you to lead us in a guided pause if you’re up for it?


I like your definition of pause. My version of it is to stop and rethink things. We often need to rethink things. Maybe you thought you wanted to travel the world, or start your own business, or get a dog, but now you find out that you can’t.

Or maybe you tried it and it wasn’t what you hoped for. Very often, I have to go back to the drawing board and rethink my decisions. I open up a blank page and I start writing. I’m usually compelled to start writing because something feels wrong. I always start by asking myself a question. I ask, “What’s wrong?”

I answer that question and I write until I have nothing more to say about it.

When something feels really wrong, I always have to stop and ask, “Am I in danger? Am I in pain?” The answer is always, “No.”

It’s nice to remember that I’m OK.

So, let’s ask again. “What am I upset about?”

I’ll answer again until I have nothing more to say. Then, I’ll ask something like, “Why is that bad? What could be good about this problem?”

That’s a hard one. If you’re upset, you have to think until you have a few answers to that, because if you’re in a bad mood trying to think what’s good about something, it doesn’t come naturally.

Some of the other questions I ask are, “Why did I want this in the first place? What was the original inspiration to make me want this? Has the situation changed now?”

Maybe the situation has changed so much that the original reason I wanted this is moot.

“Is there another way to get what I wanted?”

I think, “OK. That’s one way. What’s another way? What’s easier now, considering the new situation? What’s the most direct way to get what I wanted? What if I embraced the opposite and decided to do the opposite of what I planned?”

I like to try on different approaches. For each of these questions, I’m not sitting there with my eyes closed asking questions.

That would be pretty pointless. I actually make myself answer each one. Sometimes this can go on for a couple hours, but it’s so useful.

I ask myself, “What would be the most interesting new plan of action if you look at all your options? What would be the plan that goes with the flow of my past experiences? If I look at my past actions, what do I naturally seem to gravitate towards?”

That’s an important one. That’s been a hard lesson learned. My actions often disagree with my words. I’ll say that I wanted to do something over and over again for years, but if I look at my actions, I don’t seem to want to do that.

I go through this process almost every week with something going on in my life, or whenever I’m at a fork in the road.


You’re posing some really contemplative reflections for me. Writing things down is really therapeutic and helps me sort my thoughts.

It sounds like you’re writing twelve hours a day sometimes and going through that process.

Do you ask yourself a question and then write your stream of consciousness after that?


Exactly. I write down the question and then you try to empty out my head and put all of my concerns into writing so that I can see them.

I always push myself to squeeze out that last little drop, like with a toothpaste tube. I always try to squeeze out every last bit of it out because everything counts.

When I feel empty, I go on to the next question. It’s really therapeutic and very useful to save these, especially if you keep coming back to a certain subject in your life.

For example, if you have a certain relationship that’s ongoing and difficult, it really helps to have all your thoughts about that relationship in one place, so you can see what you wrote about it three months ago or three years ago. Or maybe it’s a job choice or the place you live. “What are my thoughts on California and my ongoing relationship with this place?”


What is the end result of this process and how does it help you feel more connected to yourself?

I define a pause as any intentional shift in behavior.

This is clearly you intending to shift as you process.


I’ll give some concrete examples.

This process recently helped me realize that I can stop feeling torn about not making music. I gave away all my instruments after that.

A few months ago, it helped me realize that I want to move to New York City and then Covid-19 happened and it helped me stop and reassess. I had even booked my flight. I was ready to get a little apartment in Tribeca and live in the middle of Manhattan and join that type of life again. A month ago, I had to say, “Wait a minute. This situation has changed and the reasons I want to go there are different now.”

I put many hours into reassessing that whole decision and realized that I want to move back to New Zealand.

It’s also why I’m living in England. I moved here to travel my butt off in Europe. I was hopping on planes every week to go visit 50 places in Europe that I’d always wanted to know better. That’s why I’m here. But now, I can’t do that.

I had to reassess all of that and what it means to me. I asked myself, “Why do I travel? What’s the point? How can I still get the benefit of that? What’s the most direct way to do that?”

This process helped me first make peace with the idea of not travelling anymore. I like to take thought experiments to an extreme. In that case, I asked myself, “What if I could never travel ever again? Would I be OK with that?”

I made my peace with that thought and asked, “What was the original reason that I’m traveling?”

I’m not a hedonistic type. I was really doing it to learn more about other cultures, so I asked, “Is it possible to learn about a culture without getting on an airplane?”

Yes, of course it is. “How can I do that?”

I also apply this process to little programming projects because it helps me question why I’m doing them. “What’s the real point? Why did I start this project?”

Lastly, it gives me creative insights into alternate paths to get what I want. I often start down the path that’s obvious. Halfway down the path, I realize that the obvious path is not the optimum path, and so on.


As someone who’s lived in many places, you’ve had many opportunities to pause.

Tell us a little bit about what you’ve learned from pausing.


Pausing helps me process disappointment.

I often deliberately do these ridiculous life experiments based on some theory. I try things out just to have an adventure. Someday when I can’t walk anymore, I want to look back at a full life.

In theory, certain things sound really nice, but in practice, things usually are not what you think they’d would be. There’s always a difference between in theory and practice.

I use pausing and reflecting as a time to process that and re-evaluate. Like I said. So. Yeah. Right. Yeah. Your definition of the changing of actions. The changing of actions always first starts with this process of rethinking.

An intentional shift in behavior comes after an intentional shift in how you’re thinking about things. So that’s why I didn’t explicitly say that. That’s why I’m so focused on how I think about things. I have to realign my beliefs in order to shift my behavior.


That’s a great way to think about it. I commend you for using all of these components and creating mini experiments for yourself.

Are you working on any experiments at the moment?


Let me be clear, these experiments are not tiny. They’re usually massive, life size experiments. Did you see the movie Big Fish with Ewan McGregor?


I think I did. But it was so long ago.


In the movie, Ewan McGregor plays a guy who comes from a small town in Mississippi who wants to go discover the world. He ventures out of his town and stumbles upon a forest filled with spiders.

Then, it opens up into a little paradise of a village where everybody is sweet, and the weather is perfect. The food is the most delicious food he’s ever had. Everybody there loves him. They all tell him, “Please stay forever.”

He spends one night there and then says, “No. I’m sorry. I need to go see the world. This has got to be the sweetest place I’ve ever seen, and I can’t believe I’m saying this, but I’m have to go have my adventure.”

I lived in Santa Monica for five years or so and loved it so much. I felt like it was the end of the rainbow. The Big Fish story is exactly how I felt about Santa Monica.

My girlfriend at the time wanted to travel the world. I said, “Travel? We live in Santa Monica. Do you think you’re going to find a better place than this? This is amazing!”

I refused to travel. I was so happy there. Then, while reading a random book I came across, the author said that if you want to keep learning and growing, you need to be surprised. If you’re not surprised, you’re not really learning because everything you’re experiencing fits into your existing understanding of the world.

Some ways you can continue to surprise yourself or learn about things that you know nothing about is to move to a place that’s completely different than where you grew up. That’s one of the best ways to surprise yourself on a daily basis, because everything around you will be unlike what you know.

I read this one little thought, and in that second, the wires in my brain re-configured themselves. I thought, “I need to get out of here. I’m like that guy in Big Fish. I’m so comfortable that I could see myself getting stuck here.”

I forced myself to leave my favorite place on Earth in the name of learning and growing. Even more so, I realized that I spent the first 40 years of my life in the U.S., so I wanted to spend the next 40 years out.

I’m still living that grand experiment that came from a paragraph in a book and a process of rewiring of values.


Speaking of surprises, we’re all experiencing that right now in our right now in the current situation of Covid-19.

Are you personally doing anything different or is life the same for you right now during this forced pause?


My day to day life isn’t any different. For the past year, I’ve been completely isolated. I wake up and write for 15 hours every day in my little cottage on the edge of the English countryside. But I mentioned earlier that I moved to England so that it could be a home base for weekly travels. I specifically chose Oxford because of the great schools here for my son.

But now the schools are all shut down and we can’t travel, I had to rethink the whole situation and ask myself the question, “Even though I’m here now, would I have chosen to move to Oxford given the new situation?”

The answer was no. I realized it was time to go.


When we’re dealing with uncertainty, there’s a need to refresh and renew. Is there anything you do to refresh and renew?


Sleep. I don’t have a power down routine. I’m one of those Energizer Bunny types. I bounce out of bed at 5:30 A.M., typing at full speed until I drop at midnight, sleep for five hours, then do it again.

Sometimes in the middle of the day, if my brain feels stuck, I stand up, walk away and go lie down somewhere. I’ll lie on the couch with no intention.

Usually, whatever I was stuck on works itself out in my head and suddenly after five minutes or 20 minutes, without meaning to.

Then, I jump up and get back at it. But for the most part, I sleep well.


You’re following your deeper desires every day. Pandemic or not, you’re feeling fulfilled. You’re writing, creating, learning, creating, and spending time with your son.

That’s so important and that is renewal in itself.

You’re probably busier than many people, and yet you feel renewed. I think many of us push our dreams aside because we’re busy doing X, Y, Z. We get ourselves in a bind and have a hard time finding that balance.


Thank you. I lead a very tranquil life. I say “no” to everything and say “yes” to almost nothing. My life is the opposite of busy. People ask if I meditate or do yoga and I don’t because my life is already so tranquil that I don’t have a yearning to make it even more so.


It’s great that you’re saying “no” and creating those boundaries.


It’s a luxury to say “no.” A lot of people wish they could say “no” more often. I’m 50 now, and at every stage of my life since I was a teenager, I chose that life path that would let me say “no” to more things. After 30 years of practice, this is the result.


Can you tell us about your book titled How to Live?

I’m very curious and it sounds really enticing.


Before discussing the book, I have a fun metaphor.

You’re the first person I’ve told this to.

I started this conversation by sharing all those questions that I ask myself. These questions are meant to bring up different possible futures.

I start making a catalog of possible futures in my head. I don’t stop until I’ve got at least 10 or 15 different options.

The problem is that I see most people come up with two options and think they need to decide between the two. They have a little mini dilemma because they only have two options.

Never come up with less than 10 options. Then you can decide. Here’s the metaphor I came up with.

Coming up with many options is like somebody trying to break into a combination safe. You put your ear up to the safe until you hear something click.


Like in the Muppet movie?


Exactly. The Muppet movie is the first thing that comes to mind when I think of cracking into a safe [laughing].

You put your ear up to the safe and keep turning until you hear something click. That’s when you know that you’ve found the right number. When I make a catalogue of possible futures, one of them clicks and I go, “Ahh, yes. That’s the one I want to do.”

This process can take a long time – days, months, or years.

After I sold my company in 2008, I spent a year and a half trying out possible futures in my head and none of them clicked for a year and a half. I felt lost. One day, I was sitting on an airplane, still running through possible futures in my head, and suddenly I thought, “Oh my God. I know what I want to do!”

For the first time in a year and a half, I shot up straight in my seat and started furiously planning out how I was going make this idea happen. That’s the click.

You can think of many possible futures in your head, but you know you’ve found the right one when it makes you jump into action.


You feel like you’ve been hit by something.


You have been hit by a Muppet [laughter].

Sorry I derailed your question about my next book.

I’m still writing it. I’m not here to promote it, but it’s called How to Live. It is so damn fun to write because it’s a lot like the possible futures idea.

There’s a brilliant book called Sum by David Eagleman. It’s probably my single favorite book of all time because I adore the format. It’s 40 different answers to the singular question, what happens when you die?

He makes up 40 little short stories. Each one starts at exactly the same. Each one says, “When you die, this is what happens.”

Each chapter completely disagrees with the previous chapter and they’re each two or three pages long. It’s a massively creative format to make yourself come up with 40 radically different and conflicting answers to one question.

I loved this book so much. I read it a couple times over the years. One day while driving, I thought, “Oh, my God, I want to write a book called How to Live in that format!”

I answer how should you live your life in different, conflicting ways. Each chapter is completely convinced it has the right answer. For example, you should live your life by delaying gratification and saving all your money. The next chapter will say to free your senses, do it all, see it all, taste it all, touch it all. You’re only in this world for a short time. You need to fill your senses.

The next chapter will completely disagree with the previous and say you should steer towards the pain. All growth comes from pain. Look for the painful situations. This is how you will grow.

My book has 27 of these one-sided arguments. I have a great conclusion, but it’s going to be a surprise.

It’s a blast to write each chapter. I become completely convinced as I’m writing each chapter and think, “Forget all those other chapters. This is actually how I should live.”

Two days later, I’m writing the next chapter and I’m fully convinced all over again. It’s a fun and funny book, but also helpful, I hope.


Does your daily reflection and writing process ever intertwine with writing your book?


Yes. After I had the idea to write this book, I realized I’m uniquely suited to write it because it’s what I’ve been doing in my diary for 10 years now.

I’m constantly trying on different approaches to life, like I said earlier when I realized I needed to get out of Santa Monica. Then I lived in Singapore for a couple years and was completely convinced that I should be an entrepreneur in Singapore and raise my son in Asia.

I started a publishing company and published books about 16 countries in Asia. Then, once my kid was six months old, I thought, “Wait, no, I want my kid to grow up in nature. I’m moving to New Zealand.”

I’ve lived through many of these deliberately conflicting approaches to life. I write about dozens more in my diary, so I’ve basically been writing this book for 10 years. It’s exciting to turn it into something concrete like this.


It sounds really cool.

Speaking of how to live, knowing we’re in this in this uncertain time and moving through things in ways that are unprecedented, do you have any thoughts on how to be creative during this time?

Any tips for finding adventure or joy?


When everything first hit the fan, I emailed my whole mailing list because I know a lot of them.

I emailed everyone and asked, “How are you? And yes, this is a real question. Please reply. Let me know if you’re OK.”

I got around 7,000 replies and I read and replied to all of them. I learned a big lesson learned from reading 7000 people’s updates on how they were doing with this. Most people don’t make a change in their life until something pushes them out of the nest.

A lot of people in the world are stuck in a rut and they’ll stay there until something pushes them out. Most people need somebody else to make that change for them.

Many people are changing their behavior right now, willingly or not. If you have anything in your life that you’ve ever wanted to change, now’s the best time to do it, because the whole world is taking a sick day in the big scheme of things.

Nobody’s expecting much of anybody right now. It’s a great time to deliberately make any change that you’ve been putting off.


Thank you for that thought. That’s awesome.


Do you want to know something cool?

The whole time we’ve been talking in my little house here in Oxford, England, it’s been raining. Two minutes ago, it became weirdly sunny all of a sudden.

Now there’s a giant rainbow across the sky.

Speaking of the Muppets...

[Starts singing Kermit the Frog’s “Rainbow Connection”.]


The Muppets bring it home with the Rainbow and Mother Earth.

Derek, thank you so much for this lovely song. What a great way to end.

You’re a joy to talk to you. I enjoyed how present you are. Keep singing your song.


Thanks, Rachel. I loved your book. I love what you do. I love your podcast. It’s been great to finally talk with you.