Derek Sivers

Interviews → Elevate Podcast / Robert Glazer

Success, radical honesty, doing the things that scare you, why I love changing my mind

Date: 2020-03

Download: mp3



Welcome to Elevate, a podcast about achievement, personal growth, and pushing limits in leadership in life. I’m Robert Glazer.

I chat with world-class performers who’ve committed to elevating their own life, pushing the limits of their capacity, and helping others to do the same.

Our guest today, Derek Sivers, is a true renaissance man, brilliant thinker, and creative mind. Derek’s a prolific writer and thinker who’s constantly looking for fresh perspectives and ideas.

Derek, welcome. I’m excited to have you join us. I’ve been looking forward to this interview for a long time.


Thanks, Rob. Me too.


You’ve had a very unique life path. Can you give us a quick history to set the foundation?


Sure. It didn’t seem very unique to me until I got out of it. Most people look at me weird when I tell them my past but when I was living it, it felt normal.

Ever since I was 14 years old, I wanted to be a successful musician. I set out on that path, which is one of the best things that ever happened to me. It helps a lot in your teens and 20s to have some focus and pursue something.

Because when you’re pursuing something, then you’re looking out for clues on how to be successful at that. In doing so, you achieve other things along the way.

So, I just set out to be a successful musician and I really dove into it hard. I went to Berklee School of Music in Boston and I joined the circus because it was a paying gig. I was the ringleader M.C. of the Circus from the age of 18 to 29 and did over a thousand shows.

I got a job playing guitar for a Japanese pop star touring the world and playing to audiences of 12000 people when I was 22 years old. Then, I moved to New York City and got into the music business working inside Warner Brothers.

I learned a lot about how the inside of the music industry worked from that job. Then, I was a freelance musician doing the hustle. I quit my last job in 1992. I haven’t had a job since, and I’ve been a freelance agent ever since.

When I was a full-time musician in New York City doing whatever it takes to make a buck, I started selling my own C.D. on my band’s website. It took a few months of work to figure out the whole e-commerce thing back in 1997. There was no PayPal or Amazon.

The only way that you could have a “Buy Now” button on your website was to pay around a $1,000 in fees to get a credit card merchant account.

An actual inspector would be sent out to your location to make sure you were a valid business. I had to incorporate. I had to set up a separate bank account for my corporation. They wouldn’t let you do it under your personal name. After about three months of hard work and $1,000 in set up fees, I had a “Buy Now” button on my website.

My other musician friends in New York City said, “Dude, can you do that for me, too?” That’s how my company CD Baby got started. I was just helping out my fellow musician friends in New York.

Back in 1997, things were a little different. If you were a musician with a CD that you wanted to sell, there was basically only one way to do it, and that was through a guy named Derek in New York that could do it for you.

That’s why CD Baby took off so fast and quickly became the largest seller of independent music on the web. I ran it for 10 years until I got sick of it and then sold the company in 2008.

After that, I became a pseudo retired, intellectual at large, public speaker, author type of guy. That brings us up to today.


You said you don’t consider yourself an entrepreneur anymore. Was there a specific moment that made you realize you didn’t want to be considered in that way?

A lot of people think entrepreneurialism is in their DNA. Did your decision force you to redefine yourself?


For one, it feels icky to speak in present tense about something that’s historical for me. How many times can you tell the story about something you did in high school?

You can imagine how it must feel to be Macaulay Culkin. Everyday people see him and freak out about Home Alone, and he probably says, “Yeah, yeah, yeah I’m the kid I did home alone. Let it go.”

I realized that you have to keep earning your title or it expires. Let’s use high school as an example. Somebody who played football in high school can’t call himself an athlete forever. Someone who did something successful long ago can’t keep calling himself a success. You have to keep earning it. If it was something you did 20 years ago, it doesn’t count anymore. It’s past tense. “I was a success.”

If you want that verb to be present tense, you have to keep doing it. Success comes from doing not declaring. When you hold onto an old title and say, “I’m an entrepreneur,” that gives you satisfaction without the action.

You can’t say, “I am an entrepreneur,” if you haven’t started a company in a long time because an entrepreneur means somebody who starts something.

If it’s been a long time since you started something, you used to be an entrepreneur.

Maybe you’re retired or maybe you’re retired.

Here’s the real problem and the reason I force myself to overcompensate and refuse to speak in present tense about past accomplishments. If you use the title without doing the work, you fool yourself into thinking that future success is assured.

You think, “This is who I am. I am an athlete.”

Or, “I am an entrepreneur.”

Even worse, “I am a successful person.” That premature sense of satisfaction can keep you from doing the hard work that’s actually necessary because you can get overconfident.

I made a point to stop fooling myself and to be honest about what’s in my past and what’s in my present.

Lastly, I think that if you don’t like the idea of losing your title, then you have to do something to keep it. This goes for titles like leader, or risk taker, or good friend.

If you call yourself a good friend to this person, are you still actively a good friend or did you just used to be a good friend and you coast on that status? You must constantly re-evaluate the present and the past.


I read article recently about talking to kids. When we say, “You’re smart,” you’re assigning a character trait rather than talking about the action.


There’s a woman who’s done a lot of research on this. Her name is Carol Dweck. She wrote a great book called Mindset. I highly recommend it to anybody interested in this subject. I read that book enthusiastically and took copious notes.

She refers to the fixed mindset versus the growth mindset. The fixed mindset says you are good at math. The growth mindset says you studied hard and did a good job. It’s about your actions. I very influenced by that philosophy.


Sometimes we do one small, good thing and think that excuses a lot of bad things. There’s data on this.


If we zoom out and get very meta, I adopt philosophies not because they’re true, but because they’re useful to me at the time.

I’m very utilitarian about that. Talking about earning your title, I find that philosophy useful because it keeps me focused on the action and not coasting on my past success.

But that philosophy might not be useful to somebody who’s not in that situation. You have to decide if this works for you. If this philosophy makes you take action, then it’s a good one. If it doesn’t, then it’s not.


This relates to identity and embracing fear. It’s hard for people to day, “That’s not who I am anymore.”

At work, I think many people are afraid to share more of their personal selves in professional environments for fear of being judged. It’s hard for them to be vulnerable, don’t you think?


That’s a tough one. I’m curious to ask you more about that. Ever since I was a teenager, I’ve had a rule of thumb that’s served me well: whatever scares you, go do it because then you won’t be scared anymore.

You could almost see the whole world as a to-do list of fear. Whatever you’re scared of, that’s what you should be doing, because as soon as you do it, you’re not scared of it anymore. But what’s best for you isn’t what’s best for others.

Look up something called radical honesty and the top hit is probably an article in Esquire magazine called “I Think You Are Fat.”

Everyone should read it. It’s one of the most interesting articles I’ve read on the web in 20 years. That’s saying a lot.

It’s a profile of this funny guy in South Carolina who says that radical honesty is a philosophy that he lives by and he goes around his day to day life being a radically honest with no filter at all. He tells everyone around him what he’s honestly thinking at all times. The waitress asks, “How’s your meal?” He dumps the radical truth on her.

I remember where I was when I first read the article in 2007. I presented it to my girlfriend at the time. I said, “We have to do this radical honesty thing. This is the way to go.”

But the more I thought about it, the more I realized that honesty is like nudity for intimate and committed relationships. It can bring you closer, but for most situations, nobody wants to see your junk.

Most interactions in the world are transactional. When I’m hiring someone, I want them to be professional. Professionalism means focusing on the delivered work, not on your personal, fleeting feelings or mood at this moment. We say someone is professional if they leave their personal problems at home and come to work ready to focus on others.

Your question leads me to think that that everything must be going very well for you at work to be concerned about more holistic things like people sharing their personal selves more at work.

That’s a good sign that you’re asking this question, assuming that you were asking it from your point of view. But I think that anything can be done to a fault.

For example, if someone is only professional and never shares their feelings, they might boil over with frustration and snap instead of addressing their problems.

What are your thoughts on this? I’m curious where that question came from.


I think this topic is very interesting. I want to clarify something you said earlier. You said do what scares you. Is that a personal thing, or do you believe that to be true of other people, too?


That’s a rule of life. I think about it so much that I actually turned it into a lullaby for my kid when he was two. When he slept at night, I wanted this thought to get into his subconscious.

I sang him a little song at night.


Whatever scares you, go do it.

Whatever scares you, go do it.

Whatever scares you, go do it.

Because then you won’t be scared anymore

Won’t be scared anymore.

Won’t be scared anymore.

That’s his lullaby that he’s fallen asleep to hundreds of times since he was two years old.


It helps that you can actually sing. If I sang that to my kids, my singing would scare them [laughter].


I started out singing Beatles songs or other lullabies to him and I thought, “Wait a minute. I’m a songwriter. I can do this!”

I thought about getting that message into his subconscious. I think it’s an important rule of life for everybody.

On the other hand, I’ll use radical honesty as an example. If I’m scared to be radically honest and then I decide to go around telling everyone what I think, that might not be helpful either. That may be good for you, but it doesn’t mean it’s good for others.


I have a 16-year-old daughter now and we’re heading into the high school and college age. It seems that everything is about getting on the right track. I don’t know how you embrace fear if failure is so negatively looked down.


Making mistakes is the fountain of youth. There’s often the question, “What would you tell your 20-year-old self now?”

Every time I come back to that question, my answer is the same every time. I always say, “Nothing. I like all of my past mistakes. I had to make my past mistakes in order to learn.”

For most of us, that’s how we learn. People can tell you things, you can read articles, hear tips, or have somebody wag a finger and tell you something. But most of us are going to have to learn everything the hard way.

You don’t learn until you feel the pain. You have to feel the pain to know something is a mistake. That’s another reason why, when I do make a mistake, and my friends try to say, “It’s for the best. Don’t worry.”

I say, “No. I need to feel the pain of this. It’s not for the best. That was that was a huge damn mistake. I need this to hurt in order to remember. I really want to make sure that doesn’t happen.”


If you touch the hot pot, it’s hot.


Exactly. With my rule of thumb, whatever scares you, go do it, I like applying it even to the tiniest little day-to-day moments.

For example, are you scared to talk to that intimidatingly beautiful person? You should do it.

Scared to quit your job? You should do it.

Scared to start this new thing? You should do it.

From the tiniest thing to the biggest thing, I like applying that same rule.


I’d love for you to share how you came to this idea of hell yeah or no. Can you describe what happens when we say “yes” to something we don’t want to do?


Hell yeah or no is for a specific situation. It’s a decision-making tool. If you’re feeling anything less than, “Hell yeah, that would be amazing!”

Then say, “No.”

The idea is to say “no” to almost everything. Leave space in your life. That’s the real key. Most of us say a lukewarm “yes” to too many things and our time is full.

We’re too busy. When something great comes up, we rarely have the space to give it the “Hell yeah!” attention it deserves because we’ve said “yes” to too many half-assed things.

Instead, imagine an alternate version of yourself where you actually had many hours of spare time each day because you’ve said “no” to almost everything and your schedule is almost empty.

When the occasional big deal comes along, you say, “OK, fuck yeah! This is worth throwing myself into.”

Now, you have the capacity, time, and energy to knock it out of the ballpark because you said “no” to everything else.


What are the big reasons why we don’t do that already?

Are we afraid to let people down or are we afraid to put ourselves first?


There’s the obvious fear of missing out. You had Cal Newport on your show a few weeks ago.

I love when Cal Newport talks about the Any Benefit model when people say, “I need create a social media account because it has some benefits. . .”

Don’t say “yes” to something just because it has ANY benefit. You have to also think of all the downsides.

That’s similar to the hell yeah or no idea.

“I should go to this event. I might meet somebody could there, so I should probably do it. It could have some benefit.”

But no, there are downsides too. It’s going to fill up your time. I aim to never fill up my time. I’d love to keep my time incredibly empty so that when the occasional great thing comes along, I can do it.

People usually say “yes” to too many things for fear of missing out. It’s also our culture where we think we’re supposed to stay busy all the time doing something.

I’m sure there’s another culture in the south of France where most people do nothing.

Most of the time they’d be laughing at this conversation of ours. Who knows?


But there are some things that you have to take the chance on. Sometimes it’s hard to know what has the potential for greatness.


I’ve never heard somebody bring this up before. I’m so glad you did. Thank you.

At the very beginning, you said this is a tool that everybody should use.

I get a lot of emails from people fresh out of college who say, “Hey man, I heard you talk about hell yeah or no. This is great. I’m going to apply it to everything in my life.”

I say, “Wait! No. You’re fresh out of college. In the early parts of you career, you should ‘yes’ to everything. Hell yeah or no is a specific tool for managing the overwhelm. If you’re overwhelmed with opportunity, then you need this.

If you’re starving for opportunity, don’t use this tool. It’s a tool to keep you from drowning. It’s a tool for being overwhelmed.”

Like you just said, you never know what might be a hit. Opportunities are like lottery tickets. The more you buy, the better, as long as they’re free. But get them all. Say “yes” to everything. Find what you love and let it kill you. Work harder. Sleep less. Do it all.

Then, when the world is giving feedback about what’s worth doing, that’s when you switch strategies and say “no” to everything else. That’s when you double, triple, quadruple down on that one thing.

I read an interview once with Charlie Munger, Warren Buffet’s partner. His advice to young investors was to imagine that you have one of those little loyalty punch cards that you might get from the ice cream shop.

Imagine that this is your entire investment career and you can only make 10 investments for your whole life. You might be better off sitting and doing nothing for a few years and waiting until that one thing comes along that you can tell is going to be a homerun.


This reminds me of my favorite Charlie Munger quote. He said, “Show me the incentive and I’ll tell you the behavior.”


Yes! I think about that all the time.

People also need to reframe the way they think about maximizing every second of their day. You believe productivity is not about filling your calendar.


You’ll run out of days before you run out of emails. That’s like a scary thought. The day that you die, emails are going to keep pouring into your inbox from people. It will never, ever stop.

To think that you can get on top of it is the wrong idea. Imagine that you’re an author who gets famous, or even worse, imagine that you win the Nobel Prize for something.

That would be the worst thing that could happen, because now you’re going to get invited to everything. You’re going get glamorous invitations that nobody can refuse. Everybody will want a piece of you.

Or even worse, everyone will want to email you to express their gratitude. Who could refuse that? But if you say “yes” to all of these things, you’ll never write another book.

This is short term thinking versus long term thinking. In the short term, you may have to disappoint people in order to serve them better in the long term.


We tend to unintentionally reward people who process quickly.

What are the benefits to being a slow thinker?


I see it as my job. There people who have jobs where they need to respond instantly, like a customer service job. There are many other jobs in the world where you must respond instantly to excel.

I’m happiest finding a different point of view.

If somebody says “Name a famous painting,” you say, “Mona Lisa” because it’s the first thing that comes to mind.

But the first thing that comes to mind isn’t always very interesting.

If you were to ask again and say, “No, no, no. Besides the Mona Lisa, what’s another famous painting?”

After the third or fourth time you ask this, you get a much more interesting answer because it’s not a knee jerk reaction anymore.

Most of my quick answers were outdated too. I answered that question long ago, held on to the answer, and recited it like a reflex.

Sometimes I would hear myself saying something out loud as an answer to a question and realize it’s not true anymore.

Being a slow thinker allows you to come up with more interesting ideas because you’re not trying to be fast.

I got an email from somebody in India who read my article about being a slow thinker. He said, “I do software sales in India. My clients are asking me questions about the software. I have to give them an answer right away. What should I do?”

I said, “No, you don’t have to give them an answer right away. In fact, if you always give them the answer right away, they’d be right to assume that you might be full of shit. If a client asks you something you don’t know the answer to, say ‘I don’t know the answer to that, but I’ll go find out for you and get back to you tomorrow.’

Then, go find out the answer. As a customer, I’d find it really impressive that you’re taking their questions seriously and you’re going to take the time to find the real answer.”


I think there’s a clear distinction between success and achievement.

I view success as something we achieve to impress to others. Whether that’s a huge house, great job, or a sportscar.

Achievement is something that you’ve intentionally sought out that only matters to you.

How do you make sure that you’re achieving things that matter to you and not others?


I’m testing a new technique for this. Don’t let anyone see your life. Stop taking pictures. Ask yourself if you would still want to go to that exotic location or eat at that famous restaurant if you never took a photo and never told anyone about it.

We’re all susceptible to this. I don’t just mean in the shallow Instagram right way. There are so many things that I find myself wanting, for example, writing a song or wanting to start a new company, that later I realize I liked the image it portrays more than I actually want the outcome.

Last year, there was a couple that was thinking of traveling the world for a year. Because they knew that I’ve traveled a lot, they emailed me to ask my advice.

I told them, “My advice? Don’t bring a camera and don’t tell anyone but your parents where you are. That will help you know if you actually really want to travel the world for its own sake, or you just like the way it sounds or the way it looks.

Do you want the glamour of saying, ‘We’re traveling the world,’ or do you really want the day to day slog if no one was witnessing it? Would you still want it?”


Many people judge success by material things and social acknowledgement versus being holed up in a cabin writing in New Hampshire.

You might be really happy. You might actually have to sell your house to do what makes you really happy.


I’ve been living this way for a long time.

When I went back to my high school reunion 10 years later in Hinsdale, Illinois, everybody else had these well-paid mid-level managerial jobs.

I was a full-time musician and traveling with the circus. I probably had $10,000 in the bank tops. But everyone was jealous of me. Everyone I talked to said, “I wish I did that. Now, I have a boss and I have to wear this suit.”

There’s a cliché stereotype of what success looks like. It has gold stars all over it.

If I asked someone, “You can either have money, fame, or freedom, which would you choose?”

Almost everybody wants freedom. That’s what it really comes down to.


Ryan Holladay wrote a great piece last week on happiness. When you achieve something, you automatically move the goal post on yourself. You never really let yourself enjoy it.

None of his five books made the New York Times Bestseller List. Then, his sixth book landed the number one spot. He was mowing the lawn and got the notification on his cell phone about making it to number one and shrugged. Even though it was something he wanted so badly for so long, he said, “OK. Cool I did it.”

We’re so conditioned to move the goalposts that it will never provide the euphoric happiness you dream about.


Most of us will go beyond that and do things we thought we wanted in theory, only to learn that we don’t want that.

I found out the hard way that I don’t like living in a big house with a lot of furniture. You can’t be mobile.

I’m quite a minimalist now, but I didn’t used to be. I had a lot of stuff when I was in my late 20’s but I started moving a lot. After three or four moves of packing and unpacking, I thought, “Having stuff really sucks.”

I had to learn the hard way. I can inform somebody about the benefits of minimalism, but they have to feel the pain and learn the hard way to adopt the theory.


This reminds me of thinking of a means to an end.

No matter the outcome, sometimes you’re not satisfied. But if you enjoy the means, there’s value in the whole ride.


I think we all have this. There are some things we do for the goal. We’re not in it for the process. We want the end result.

This might be an inherent personality trait. Some people are introverts. Some people are extroverts. Some people are goal driven. Some people are process driven.

Indulge me while I share a little personal example. I have a story on my website. You can find it at

It took me 15 years to become a good singer. Every single day for 15 years, I practiced singing for at least an hour a day and I sucked. I was a terrible singer. I met so many people that would say, “Just hire a singer. You’re not a singer. You’re writing these great songs and you can play guitar like a motherfucker. Be Eddie Van Halen and quit trying to be David Lee Roth.”

I’d say, “No. I’m in it for the process. I want to learn to be a great singer. I don’t care if I suck for decades.”

Somebody who’s goal-oriented would hire a singer to sing their songs and put out a record. Then, your goal would be achieved.

I’m so glad I didn’t do that. It’s a personality trait of mine. I’ve started a few different “companies” that I developed for years and right before launching, I said, “I enjoyed the process. I don’t think the world actually needs this,” and I don’t launch.

Maybe it’s fear that stops me, but more than that, I’m very process driven person and I don’t care about the end goal.

I met a sailor on the beach in Spain last week who told me this great story. We were talking about this subject and he told me about this big race around the world in a single boat that few people in the world have ever achieved.

One man was in the lead. When he was almost to the finish line, instead of crossing it, he turned sideways and decided he would rather just keep sailing. He purposely didn’t get the gold because he realized he didn’t want to stop.

I can relate to that.


It sounds like you have learned not to fall victim to the sunk cost bias.


Oh no, not at all. I’m thankful for all the people who made us very aware of all these cognitive biases.

I’m glad that someone gave that one a catchy name because I think about that often.

For example, it costs around $7,500 to attend a TED conference. Ten years ago, I attended it a couple of times and really enjoyed it. Then, I had a kid and didn’t go for six years.

A couple of years ago, I thought I might want to attend again but you have to register 11 months in advance. They sell out far in advance. I paid my $7,500 and when it came time to get on the plane and go, I thought, “I don’t want to go. I don’t feel like schmoozing for three days and listening to other people talk. I’m on a good roll with my writing right now.”

I blew it off even though I spent $7,500 on a ticket and $2,000 on the flight and hotels. I thought, “Damn, that’s hard to walk away from, but that money was already spent 11 months ago. That’s the sunk cost fallacy, isn’t it?”


That’s the quintessential hell yeah or no. You decided what you really want.

The thing I’m almost embarrassed about it that I actually did that two damn years in a row. Now, I’m no longer handing $7,500 to Ted for no reason. It’s nice to know that half of it goes to charity, but I’m not doing that again.

I think a lot about the difference between services and goods and our regret factor.

If we go out to dinner and it’s below our expectations, we pay $100 and it’s done.

But when we buy a $100 sweater and never wear it, it sits there and bothers us. It’s not any more money than the dinner, but we can’t get rid of it.

There’s something about the sunk cost in this physical realm.


I’d argue that the dinner is already a finished transaction. The money’s gone when the food’s gone and you pay the bill.

The sweater is like the story someone who bought a stock that tanked. They don’t want to sell it because selling it is an admission of failure. Getting rid of the sweater is the admission that it was just a dumb purchase. But if you hold onto it, there’s hope that you might wear it one day.


Shouldn’t the admission be freeing? I actually think the pain is felt by something sitting there staring at me. It’s not about the money, it’s what it represents.


A month ago, I gave away all my musical instruments.

My two guitars and keyboard were in my line of my sight every single day. My soul was conflicted. Every day I would look at that musical equipment and go, “I want to do that, I need to do that.”

But my priority was programming and finishing my book.

I called up a friend of mine here in Oxford that’s a full-time professional musician.

I said, “Mark, how’d you like to have my guitars?” He said, “No way. Dude, are you serious? That Fender.”

I said, “Yep. You want it?”

Mark said, “Hell yeah, man!”

I said, “Do you want my Native Instruments keyboard?”

He said, “Holy shit. I was just about to buy one of those myself!”

He was so thrilled. He uses it every single day. He’s so happy. I thought I would have a period of mourning after giving my music away. Instead, I felt so much lighter.

And I’m so glad that I’m not looking at that stuff feeling guilty every day.


You describe many of your ideas and arguments as being countermelodies.

Does being a contrarian come naturally to you? Why is taking that perspective important to you?


Mostly, I do it for my own sake. I like the personal challenge of finding a different perspective.

It’s more useful to others, too. If I gave you standard, conventional answers to all your questions, it would be a waste of time for people to listen to. Nobody would hear anything new or surprising.

I have a theory that we we only really learn when we’re surprised. If something doesn’t surprise us, it fits in with what we know already and with our view of the world.

We didn’t change any brain cells. We might have added some information, but we didn’t learn anything. When I accepted your invitation to come on your show, it became my job to help find a different, surprising, unexpected perspective to anything you’re going to ask me. That’s now my job as the guest.

People listen to an interview like this because they want new ideas. They’re not looking to reinforce what they already know. They want an eyebrow to go up.

I think of it as my job in the world as a public writer, thinker, speaker at large.


How do you think about that particularly with the U.S. and politics, where everyone is entrenched in their beliefs?


That’s a big question. I suspect that some people won’t ever change their foundational beliefs. They say, “No. Damn it. This is who I am. This is what I’m all about.”

I’m not even going to go there. I’m not going to touch that stuff. I will not talk politics. I don’t even want to debate. I’m not going to try to argue somebody out of their point of view. Nobody’s going to do admit with their humble head hung down that they were wrong.

That doesn’t happen. Instead, I like to think of these tiny things in our everyday life that we’re not using to prop up our identity.

Here’s another way to think about being busy. Here’s another way to look at fear. Here’s another way to look at radical honesty. Let’s talk about things that are not button pushers.


It’s important to try and understand why someone’s buttons are pushed. I want to understand their side. It’s in my interest to do that, rather than block it out.


Sometimes there are times in our lives where we don’t want to have our minds changed.

“I’m barely hanging on. This is all I can do. I don’t want my mind changed on this thing. Damn it. I’m just trying to make it through the day.”

Many people aren’t open to it.

You also mentioned wanting to understand somebody else’s point of view.

I have a story about this. Ten years ago, I moved to Singapore and I became a permanent resident. During the first year I lived there, I thought everybody was wrong. Many universities invited me to speak to their classes.

Singapore Management University asked me to speak to one of their business classes.

I started out by asking, “How many people here want to start their own business?”

Out of a 60-person class, one hand slowly, reluctantly went up. I thought, “What the hell? I’m so confused.”

If you ask that question in California, 61 hands will go up. Somebody will run in from the hallway to raise their hand. Everybody wants to start their own business in California.

I thought, “Maybe they’re just being shy.”

I picked out specific people and asked, “Why don’t you want to start your own business?”

This student said, “I’ve spent a lot of money on the school. I can’t take the risk.”

I asked another kid, “My parents are shop owners they worked hard so that I don’t have to be a shop owner. I want to get a steady job.”

The whole time I thought, “No. You’re all wrong. You’re doing life wrong.”

It took me a good year of living in Singapore and having lots of Singaporean friends before I finally understood the Singaporean mindset. It’s Confucianism. It’s very top down. Doing your own personal desires are whimsical and not important. Do what’s best for the group.


This is where I’ve learned that travel is critical.

Danny Meyer and some people in the USA are working to eliminate tipping at restaurants. There’s some clear data around prejudice and tipping.

You don’t tip the nurse at the hospital who works for you and you don’t tip the barista, but you tip the bartender to get to your beer.

Nowhere else in the rest of the world does tipping exist like it does in the US.

Traveling opened my eyes to this. Sometimes tipping is actually offensive in other countries. People that are deep in the industry here can’t fathom that.


I love that. In Japan, almost everything is opposite.

Once, I asked a Russian guy why Russians don’t smile. He looked at me with a frown and said, “Smiling is rude. If you smile at somebody, it’s like saying, ‘Fuck you. My life is awesome. Yours is bad.’ If somebody smiles, they’re trying to be superior. Either that or they’re showing themselves to be a fool because of what kind of fool would smile at this world we’re in.”

These are the small things that I like to sing the countermelody to. Nobody is going to change us from being a liberal to a conservative, but you can start to understand another point of view on smiling or tipping. It’s fun to see things from this opposite point of view.


I’d love to hear a little bit about your creative process.


I don’t have much to say about this because I’m not very deliberate or structured about it. I do keep an open email inbox. It’s something I really enjoy. At the end of this conversation, I’ll ask your listeners to send me an email and introduce themselves.

I really like hearing from people around the world and hearing what they’re doing and learning about what they’re struggling with. It inspires me. I like thinking about all these questions people ask me. I like hearing about other people’s problems.

I actually love noticing where I disagree with the assumptions that society has. For example, you have to stay busy, you have to keep moving forward at all times, you have to tip.

It’s fun to replace a period with a question mark. I do a lot of journaling. I usually write for one to three hours a day privately asking myself questions, and most importantly, questioning my answers.

First, I ask myself a question, then I answer it. Then, I question my answers and doubt myself. I assume that I’m full of shit and that anything I’m saying is an old, outdated belief that it’s time to expire or beat it up a bit and see how robust it still is.

All of this is driven by one of my greatest joys in life – better than chocolate, better than sex, better than a good James Brown song, which is to change my mind about something.

It is such a deep, deep joy to have your mind changed about something. You suddenly see something important or big from a new point of view that you could have never imagined yesterday.

That’s why I love living around the world. That’s why I moved to Singapore. It’s why I moved to New Zealand and why I’m living in Europe now.

It’s also what I love about a place like Japan or Finland. It’s so interesting to read books about the culture of Finland and learn about the Finnish attitude towards silence or communication.

To answer your question, I don’t have a creative process. I’m not a daily ritual kind of guy. It is a constant, ongoing life pursuit for me.


You have structured daydreaming, right?


Quite often I lay down on the couch and just do nothing but sit, space out and think.

I usually end up bouncing back up with an idea that I would have never thought of if I didn’t lay down on the couch.

I also have these blank text documents that I type my ongoing thoughts into every day. That’s where I do most of my thinking and questioning and challenging beliefs.


That’s my last question. What is a personal and professional mistake that you’ve made and learned the most from?


The example that comes to mind is mis-classifying myself and what I’m doing. Years ago, I would have said that I’m a programmer and entrepreneur who sometimes writes little blog posts sharing what I’ve learned, but that’s something on the side.

I never felt quite right about my titles. Anytime I was around other entrepreneurs, I found myself getting tired. I noticed that whenever people wanted to talk business, I wanted to go to sleep.

Last year, I asked myself during a journaling session, “Who are my heroes?” I wrote down about 12 people and looked back at the list. I thought, “Oh my God. All the people that I look up to the most and would most like to meet are all authors.”

I misclassified myself and misunderstood what motivated me. I realized that I actually wanted to be a writer.

I deliberately rearranged my hierarchy of interests and reclassified it in my own head. I admitted that while I enjoy programming, I do it as a hobby. It’s not my main pursuit.

Someday, I’ll probably start another business. But really, my main love and top priority is writing.


Maybe you should start a business to help authors just like you started a business to help musicians.


In the E-myth revisited, the author talks about the difference between being a cook and opening a restaurant. Maybe you just want to be a cook. You don’t want to turn it into a whole system. My writing is something I’m not going to systematize.


We’ll wait and see what’s next.


Like I said a bit ago, I really like meeting the people that listen to these interviews. It’s the main reason I do this. I’m not here promoting anything. I really enjoy meeting people who listen all the way through these interviews.

If you listened all the way to the end of this, please go to and send me an email. My email address is in big letters and I still read and reply to every email.


Derek has a great minimalist website and his newsletters are short and concise. You can see what he’s working on. I can attest he does write back.

Do you have some books coming out soon?


My next two books are already done. My previous book was published through Penguin.

There’s a very sweet woman who was my main rep at Penguin Portfolio. She’s wonderful. We’ve gone out to dinner and she’s a fan of my work.

She told me that they’d like to publish my next few books, but I told her I wanted to try out self-publishing. I enjoy doing things myself, even if it’s the hard way, even if the book earns less because I really enjoy that process.

I thought I was going to follow the typical template and put them out through Amazon like everybody does, but I started feeling a little punk.


So not a surprise, by the way [laughter].


[Laughter] Thank you.

When I started CD Baby in the mid-late 90s, there was a certain indie music spirit where all the musicians who signed their rights away to EMI, Universal, and other big corporations suddenly said, “Man, I don’t need to sign away my rights. I can do this shit myself, even if I’m going to earn less. I get to keep my own rights.”

I’m punk about this publishing route. I’m going to put my book on my own site, sell and ship it directly, and have the downloads directly on my own site, at least for quite a window of time.

Maybe I’ll put the books on Amazon afterwards, but I’m really enjoying doing all of this myself.


I’m excited to see how it all works out. Doing what everyone else is doing often produces a disproportionate result.


I get the direct relationship with people buying my book and I get to customize things that can’t be done if I did it through Amazon. I’m enjoying nerding out on this. As you can tell, I’m not driven by the big bucks. I enjoy the process, control, and the creativity.

Thanks for a fun conversation. I really enjoyed this.


Thank you for coming on the show. I’ve been huge fan of your work for years and you did not disappoint.