Derek Sivers

Interviews → Famous Failures / Orzan Varol

Dealing with criticism, how quantity leads to quality, separating decisions from the outcomes, why I don’t believe in failure.

Date: 2020-05

Download: mp3



Hello and welcome to another episode of Famous Failures, where I interview the world’s most interesting people about their failures and what they learn from them. I’m your host, Orzan Varol. Today’s guest on the show is Derek Sivers. Derek is one of my favorite thinkers and authors.

In the episode, Derek and I talk about how Derek cultivated a practice of questioning assumptions, why he has what he calls a making room instead of a living room, what a controversial blog post taught Derek about handling criticism, why you should distance your private persona from your public persona, what a failed marriage taught Derek about the meaning of failure. why you should separate your decisions from the outcome of those decisions, and finally, how Derek cultivates calm in his life. Derek, welcome to the show.

Six years ago, I heard about you from Seth Godin. I picked up a copy of your book, . Anything You Want: 40 Lessons for a New Kind of Entrepreneur, which I’m holding in my hands right now. It’s less than a hundred pages long. It’s the kind of book that you can read in an hour or two. Still to this day, it’s the only book where I forced myself to stop and limit myself to one chapter a day.

I read the book over the course of 40 days because it was a delicious feast and I wanted to enjoy every bite and not binge on it. So, it’s such a pleasure to be speaking with you.


Thanks. That’s a great compliment. I appreciate it.


You are a master at singing the countermelody to other people’s melodies. How do you determine what to question in life? And once you determine what to question, how do you actually practice questioning those assumptions?


That’s a great question. It’s kind of trivial, but you just reminded me something that I haven’t thought of in 20 years.

When I was 18 and at the supermarket, I put my groceries on that black belt that rolls up to the checkout counter. I started stacking them up in a funny pyramid. Why not play with it? I didn’t think anything of it until two months later, somebody stopped me on the street and said, “Hey, do I know you from somewhere?”

I said, “I don’t know you. I’m sorry.”

He said, “I know! You’re the dude that stacked up your groceries at the grocery store last week.”

I said, “How do you remember that?”

He goes, “I thought that was really cool. I’ve never seen somebody do that with their groceries before.”

I said, “Oh, I wasn’t trying to be cool. I didn’t know anybody was watching.”

I think I set the bar very, very low for what to question. That’s why I told that story.

I enjoy the process of asking myself if there’s another way to think about things. Start questioning when something’s not working. If you’re doing something that you need to do, but it’s exhausting you, or you’re not getting the results you want, or it’s not fun anymore, then you should question it.

For example, some people are always looking for a mentor, but they don’t have one. That’s something that you should question. Do you need a mentor? Why do you need a mentor?

Then there’s asking yourself, “What could be better?” If you feel something has a lot of unnecessary rituals, or if something’s over complicated, or if it could be improved in any way, then you should question the assumptions around that.

A recent example of that is I suddenly felt that everybody around me was quoting others. They were trying to make a point, but they were spewing bibliographies out of their mouths every time they speak, “This philosopher said this, and that book said that. I was reading something the other day in The Washington Post and this columnist said this. . .”

I thought, “Come on. That’s a lot of verbal garbage. Just get to the point.”

Another category would be if something just feels wrong. If it seems to offend your sensibilities somehow. To me, it feels wrong that so many people are dependent on the cloud right now. They put all their stuff in the cloud and they think that the cloud is going to take care of their stuff, as if Google cares about you.

I worry when I check my email inbox and 90 percent of all emails I get are Something feels wrong about that. That should be questioned.

Lastly, my favorite is curiosity. Look at almost anything in life short of stacking your groceries on the belt and ask, “How could this be different?”

I’m sitting in my house looking over my shoulder at this room that most people would call the living room. When we moved to England, I questioned if I even wanted to buy a house. The house I had my eye on had this great, big room in the middle and I thought, “A living room? I don’t watch TV. I don’t sit on couches. I don’t hang out. I’m just always making things.”

My kid is the same way. When we play, we’re constantly making things. I said, “That’s not the living room. That’s the making room! There will be no couches in that room. We’ll have making tables!”

As soon as I had that thought, I said, “Yes. OK, now I want that house. This is going to be a making house with the making room.”

There is nothing wrong with a living room. But I was curious. Is there a different way to look at your house? Instead of thinking of it as a place to relax and veg out and do nothing, can my whole house be turned into a place that exists to create?

Those are four categories for you, but you asked how to cultivate the practice, too.

Questioning assumptions can be done in conversation with friends, but I find it most useful when I’m writing in a private journal. Even among friends, you might find yourself accidentally holding on to a point of view just because we have a social instinct to defend our point of view.

If somebody says, “Why do you think that.” you tend to get an almost visceral, physical reaction and put up your shield. Suddenly, you are defending a point of view that you don’t actually really care about that much because it’s human instinct. So, I found that writing privately in a journal seems to be the most useful.

You can write a simple sentence like, “A house has a living room,” and as soon as you write that sentence, you can write, “Does it need to? Why is that? Do I want to spend my life sitting on a couch watching things? No. What do I want to spend my life doing?”

A great question to ask is, “What’s the real point?”

Try to boil things down to their essence. Ask, “What’s the real point of that?” See how far down you can go to get to the essence of why.

Going back to the example of people always looking for a mentor, “Why do you think you need a mentor?” It might be because you want someone to tell you what to do, so you can try to make smart choices.

Ask yourself, “Does that need to be a person that’s going to spend many, many, many hours with me over the course of years? Someone who knows me deeply? Or can that wisdom come from a book? Let’s look at my history. Where have I gotten the best ideas that I’ve ever had? Was it from somebody that got to know me really well for a long time and then gave me some bit of holy wisdom? No. So why do I think I need that?”

For quoting others instead of saying it yourself, ask yourself, “What’s the real point of quoting this person?”

People want to share interesting and useful ideas and assume they need to give credit for everything they’re sharing because it’s not their own idea. Why do we think we need to do that?

We don’t want to be seen as plagiarizing or stealing from others, but we’re not writing academic journals. We get that habit from schools where we have to list all of our sources. Ask yourself, “How would it look if I didn’t quote? If I simply heard an idea that I like, can I say that idea without crediting the source? How would that go? Is that evil? Is that OK?” Consider it.

I mentioned depending on the cloud. What’s the real point of that? People want to share their photos, contacts, or documents and have them available on a server that’s outside of their device. Well, do you need to use Google or Facebook for that?

And then lastly, the curious category. My favorite example is when I was in New Zealand at the Auckland airport. I saw the globe rotated around so that New Zealand was on top instead of the bottom.

All of the other countries from Canada, Russia, Europe were on the bottom. I thought, “The globe is a circle. Why did we assume that this has to be up, and this has to be down? You can look at a circle from any perspective, and this map is also correct.”

I did my first, and still my favorite, TED Talk on this subject. If you go to and search Derek Sivers, the talk is called “Weird, or Just Different?” My single favorite fascination in the world is to think about things from an opposite perspective of how we’re used to thinking of them.

It’s still correct. The opposite is also true. In my little tiny TED talk, I give my favorite examples of that.


It sounds like you’re applying the scientific method to your ideas in your private journal. You write down a hypothesis: A living room is for a living. Then, you question that hypothesis. You try to falsify it, and then question it again and again. It’s a continuous cycle of questioning until you get to the essence of something.


Right. The only difference with the scientific method is that I’m not trying to prove a right answer. I’m deliberately looking for a different approach. Just for fun.

If I’m doing something that’s not working or if I feel that something could improve, then yeah, I’m trying to look for something that seems better than the current way. But often, I’m looking for a different approach for the sake of being different. It’s fun.


I teach law students, and one of their biggest problems is over-quoting. They’re constantly quoting other sources.

Partially to avoid potential plagiarism issues and also to protect themselves from criticism. Because if they’re attacked, they can retreat and say, “I’m relying on this other, more important, smarter person’s views and not my own.”

I want to ask you about facing criticism.

People often worry about what other people are going to say about them. If I start a blog, or a business and it fails, what if others point and laugh? What if I make a fool out of myself? What are my family and friends going to think?

Can you share a moment in your life when you faced some serious criticism and how you handled it?


I should start by saying that everybody should have an Internet name that is not their real name. Everybody should have a stage name. It’s really handy. Bono’s real name Paul Hewson. If people are attacking Bono, he knows that they’re attacking a character that he created as the singer of U2. But it’s not him.

The real Paul Hewson sits at home and has tea with his family. Then he puts on the shades and the outfit and goes up on stage to be Bono.

Years ago, I wrote a blog post about the Ruby on Rails programming system. You wouldn’t expect it, but it’s almost like a religion when you get into a programming language. If programmers use the Ruby language, they’re convinced that Ruby is the best. If somebody uses Haskell, they say “No, no. Haskell’s the best. How dare you say it’s not?”

I wrote all of my software for my company, CD Baby, in the PHP programming language at first because it’s all I knew. Then, I tried to rewrite everything in Ruby on Rails for two years, and after two years I gave up. I thought, “No, I’m just going to leave it in PHP. It’s fine.”

I posted a little blog entry that I thought nobody would see titled, “Seven Reasons Why I Switched Back to PHP after Two Years on Rails.” This was before I had a public blog. I posted this on a little technical blog where I had zero viewers.

But two programmers over two months had asked me, “Hey, dude, why did you switch back to PHP?” I got sick of answering the question by email, so I wrote the blog post to share with the occasional nerd who wanted to know.

After I wrote the post, I went to bed. Coincidentally, it was my birthday. When I woke up in the morning, I saw that many of the tech news sites had reposted my article. There were hundreds and hundreds and hundreds of people attacking it and insulting me. They said things like, “This mouth breathing idiot is the biggest problem with the world today. This guy obviously can’t code his way out of a paper bag!”

For 15 minutes, I was really upset. I thought, “What the hell guys? I was just trying to share my thoughts. Wow. People are really mean.” There were hundreds of comments and 95% of them were negative. Every now and then, there was a little voice out there that said something positive, but then everybody else would attack that voice.

But then, something clicked in my brain. I said, “Wait a minute, these people don’t know me. They also don’t know my code. They’re telling me I’m a bad programmer, but none of my code is public. So, they’re not even really talking about me. They’re talking about themselves, or their beliefs. Or, they’re just spewing stuff to justify their decision of learning Ruby on Rails. How dare somebody criticize the last two years of my effort learning Rails?”

I realized that they weren’t talking about me. Yes, it was my name on the article, but they were attacking a mannequin of me – a cardboard cutout in the shape of me. That’s what they were throwing tomatoes at. In that one split second, something detached in my head. I realized that my public self is not the real me. The real me is the Derek that a few dear friends and family know.

But Derek Sivers is a public character that I put out into the world. My articles, books, and videos are all public creation. In hindsight, I wish I would have created a stage name. But if it’s not too late for you and you haven’t started to put a ton of stuff out in the world, go get yourself a stage name and use that publicly so that if people attack it, it’s not the real you. You can shrug it off as feedback.

If I put an article out into the world and everybody attacks it, I think, “OK, I need to think through my thoughts on that subject because it’s clearly being misunderstood.”

But I never for one second think that they’re attacking me. This also means that you can’t take any praise personally either. When people say really nice things about me in public, it also has no effect on me. I’m disconnected from all of it. So, any praise, or any criticism? It’s feedback on something I’ve created. None of it is about me.


You can’t take the compliments and the praise and then reject the criticism.

You have to treat both the same.

It reminded me of a verbal tweak I implemented in my life when I first started out in academia. At conferences, I would say, “I argue X, Y and Z.” Then, when people attacked my arguments, I would get defensive. Because when I say I argue, my arguments and beliefs are tied up with my identity. So, when those arguments and beliefs are attacked, it’s almost like my identity is being attacked.

I think this is why so many disagreements in the real world turn into these existential death matches. When you have people who say that they are paleo, or they are vegan, or they’re crossfires, those labels tend to get tied up with ego and identity.

So, I switched from saying I argue to I hypothesize. That simple verbal tweak was really useful in separating me from my ideas and products. I think your approach is even better because it takes us a step further.

There’s a difference between the private me and the mannequin of me, the public me. As long as you’re doing that for both criticism and praise, that’s a great way of handling any critique that comes your way.


And a different name would help. My son is only eight years old. A year ago, he wanted to create an account on Minecraft and I said, “OK, it’s time to make up your Internet name.”

He said, “Internet name?”

I said, “You can’t use your real name on the Internet. You always have to use a different name on the Internet.” It has become a truism in the household. I think it’s really healthy.


Can you share one to three of the most valuable failures you’ve had in your life and what makes them such?

I’d also love to hear about your personal definition of failure. I’ve been doing the show for now over two years and people have different views and different definitions of failure.


I don’t believe in failure because it seems to imply that something has ended. Even if you want to pick the most obvious example of a failed business, if you learned something from it and you’re going to try something else, then you could say that it wasn’t a failed business.

We’ll use my first marriage as an example. First, I need to clarify that she was my girlfriend from Sweden. She kept coming to visit me in America, but the third time she came to visit me, immigration at the airport told her, “I’m on the verge of rejecting you, but I’m going to let you in this one last time. I’m putting a note on your account. You’re not allowed into America anymore unless you have a work visa or a marriage visa or something. You’ve been visiting too much. Something’s up.”

I tried to get my company to hire her, but it can be like a year and a half of paperwork. So, we went down to city hall and signed a piece paper. I thought, “There, we’re married. Leave us alone.”

So, yes, she was my girlfriend. But no, we didn’t make this decision to spend our whole lives together. We stayed together for six and a half years, and it was awesome. We were really, really happy.

We didn’t fight during our six and a half years together. We had one disagreement about whose turn it was to clean the bathroom. We got along so well. It was just great. But our lives were going in slightly different directions. She wanted to stay in L.A. and dive into film school. I wanted to be up in Portland to work on CD Baby. We could tell that we were drifting apart.

One day, we went out to a movie and after the movie, we were at the Third Street Promenade in Santa Monica, California. We got two lemonades. We looked at each other and one of us said, “Do you want to breakup?” And the other one said, “Yeah. Do you?”

“Yeah, I think so.”

“You’re not upset?”


Are you hurt?”

“No, I’m good.”

“Wow. Yeah. Let’s do this.”

So, we broke up and did a little cheers with our lemonades and walked home.

That night while she was asleep, I was so excited to start a new chapter in my life that I packed my bags, hopped in the car, kissed her goodbye, and never saw her again. It was a great marriage. But a lot of people would call that a failed marriage.

Now, let’s talk about songwriting. All professional songwriters write many, many songs and most of them don’t become big hits. But are all of those songs failures? Of course not. You don’t say that’s a failed song. That’s so condemning. Instead, you say, “Those weren’t a big hit. So what? Who expects every song to be a big hit?”

Another example is dandelions. I’m surrounded by them right now. You blow on the dandelion, and 100 little seeds go off into the wind. Are they failed seeds if they don’t turn into more dandelions? Of course not because quantity prevents the failure mindset.

The only songwriters I ever met who might have said that a song was a failure were the occasional oddballs who only wrote one song about their mother or their wife or something. They went around L.A., New York, and Nashville trying to make this song a hit and nobody wanted it. They were putting so much effort into this one song, they’d get really upset when people didn’t like it. To me, when you believe that this one thing is everything and everything’s riding on it, that is more of a failure mindset.

This is true even with businesses. You can make lots of businesses with the songwriter approach. You can start four businesses a year. In the future, if 25 of those businesses didn’t become a big hit, does that mean they were all failures? Probably not, because you think of it differently when you think in terms of quantity.

Quantity prevents the failure mindset.

I once asked Jeff Bezos how Amazon seems to make no mistakes. I said, “It seems like everything you do is a big hit.”

Instantly, he named seven failures. And for each one of his examples, I thought, “Oh, yeah, I’d forgotten about those.” They were almost all things that I had heard of but forgotten about. They drifted into history and nobody mentioned any more. That was interesting to notice.

You don’t necessarily have to launch an absolutely new company every few months. If you have one company, you can try lots of things inside of it. Think of yourself like you’re in the quantity business, so you can keep trying many things.

There’s a great story in the book Art and Fear. It’s a story about 50 pounds of parts.

The teacher of a pottery class decided to do an interesting experiment. He stood in front the class and split them in half. He said, “Those of you on the left half of the room, you’re going to work on one piece of pottery for the whole semester. At the end of this semester, I’m going to grade you on how great that one piece of pottery is. Those of you on the right half of the room, just do whatever the hell you want. Create, create, create as much as you can. And at the end of the year, I’m not even going to look at what you make. I’m just going to grade you by weighing how much you’ve made. Alright. Go.”

At the end of the year, they actually brought in an objective outside judge to judge all the pottery in the room, not knowing which half of the class it came from. The pieces of pottery that the outside expert found to be the best were, of course, as you can predict, the ones that were in Group B, the people who were focused on quantity. They became better potters.


With respect to your question for Jeff Bezos, we tend to remember the highs and not the lows. People forgot about the Amazon Fire phone, which cost the company a lot of money.

It was a colossal failure.

Tom Hanks is one of my favorite actors and he’s been in some awful, awful movies. But when you think of Tom Hanks, you think of Philadelphia and Apollo 13. You don’t think of The Man with One Red Shoe, which is awful [laughter]. So that’s important to keep in mind, too.

Quantity leads to quality, but the “failures” tend to be forgotten. People tend to remember the hits.


I have this thing that I call my ThoughtsOn journals. I used to only write a daily diary, but I found that there were certain subjects I kept coming back to, so I started creating new text files for these topics.

I have a journal called Regrets. Every time I do something I regret, I write about it in that journal. It’s a catalog of my regrets. For each one, I ask myself, “What happened? What do I wish would have happened? What do I regret doing? What will I not do next time?”

One of my biggest regrets of all time is a little weird to talk about, but I sold CD Baby in August of 2008. It was an all-cash deal. I suddenly had a bunch of cash. I read investing books for the six months prior thinking, “I have to learn about investing now.”

Not like Silicon Valley angel investing, but more like old, tried and true wisdom about passive investing into broad indexes of the entire world economy. One of the truisms I learned was from a Warren Buffett quote that said something like, when everybody’s screaming, “We’re all going to die!”, then it’s a good time to buy.

He said you should be the most optimistic when everybody’s scared and you should be the most scared when everyone’s optimistic. It was weirdly lucky timing that I sold the company in August of 2008 because weeks later, the financial collapse began. It was collapse, collapse, collapse. Dominoes falling everywhere.

So, I did nothing. I sat in all cash. I hired an investment adviser. Somebody to bounce ideas off of because I was new to having money. I was totally new to investing. I opened an account at Vanguard and I had this guy who I’d call monthly to bounce ideas off of.

In February of 2009, the cover of every big magazine claimed we were going to be in the next Great Depression. We’re in for a long period of doom. I thought, “This is what the wisdom told me about. Everybody’s screaming, ‘We’re all going to die.’ This is peak pessimism. I’m ready to invest now. I want in. I’ve already got my asset allocation decided. I’m going to invest now.”

I called up the investment adviser. I said, “OK, I’m ready. Let’s do this. I’ve got the asset allocation picked. Here’s the mutual funds and the indexes that I want to do.”

And he talked me out of it. He said, “Derek. This is why you hired me. We’ve got a long way to go. You ain’t seen nothing yet. It’s going to fall another 90 percent. You mark my words, Derek. This is why you hired me. Don’t do anything. Just wait. Don’t be foolish.

I said, “No Stephen! I can’t. This might not be the absolute lowest, but I’m ready. We’re in times of great pessimism. Everybody’s predicting doom. I’m ready. This is a great time to get in.”

“Derek, I’m telling you, this is why you hired me.”

I let him talk me out of it.

But I went to one of those sites like Google Finance, and I put together my hypothetical portfolio that I would have done. I was curious to see. Over the next five years, that portfolio went up 1000%. I was right. If you look at the Dow Jones Industrial Index, that day that I had the phone call with my investment advisor turned out to be a bit like the bottom of the market.

So, that truism held true. When everybody’s screaming, “We’re all going to die,” it’s a good time to buy. I was really mad because I sat in cash and then things started skyrocketing up and up and up. So, I stayed in cash. Eventually, I fired the investment adviser.

Years later, I humbly admitted that I had made a huge mistake. Here’s the interesting thing – in this case, I was right, and he was wrong.

I can say that I should’ve trusted my gut. But what if the random meandering of the stock market had gone the opposite way and he was right, and I was wrong? I would have said, “Boy, it’s a good thing I listened to him. I guess it’s good not to trust my gut. Our feelings are often wrong. We should listen to the wisdom of our elders. . .”

It made me think about something that would be really interesting to talk about, which is the difference between good and bad decisions and good and bad outcomes.

I could have made a good decision that day and gotten a bad outcome. I could have taken all the wisdom I learned from all of the investing books and done the wise thing, and it still could have totally tanked. It could have had a bad outcome. But maybe, I would have said that was actually still a good decision.

Or, I could have made a dumb, crazy, bad decision that day. I could have said, “ I really like my new iPhone so I’m going to invest in Apple, even though I know nothing about the internals of Apple or whether it’s a good investment. I just like Apple. I’m going to put all my money on this company.”

And then that one investment could have skyrocketed, and I would have said, “See? That was a good decision.”

But no, you could objectively say that that was a bad decision, even if the outcome turned out amazing. We need a different way of judging or quantifying a good decision or bad decision, regardless the outcome.


Applying that in practice, I have a chapter in my new book called “Nothing Fails Like Success.” I talk about a series of bad decisions that NASA made in the lead up to the Challenger and Columbia space shuttle disasters. Those bad decisions produced successes and so they went unchanged until we ended up with disaster.

In this chapter, I talk about the need to conduct postmortems or investigations after both success and failure. We should ask ourselves the same questions after both success and failure. What went right with this failure? What went wrong with this failure? Similarly, what went right with the success and what went wrong with the success?

One thing I struggle with is applying that in our personal lives. The outcome is almost like a blinding light. When you get a successful outcome, it becomes really hard to resist the tendency to start popping champagne and lighting cigars and actually dig deep and say, “How do I figure out which of these decisions were bad and which of them were good? Did I get lucky in this instance from a bad decision, or did I actually make the right call?”

Do you have thoughts on that?


I wish that we had an objective and even catchy way to describe what makes a good decision. Something like “Five Rules that Make a Good Decision,” so that people could reference that in moments of decision making. I asked my music teacher, Kimo Williams, about this. I wrote a story about at He was a huge influence on me. He was my music teacher when I was a teenager and we’ve kept in touch.

He’s the one who introduced me to this concept of separating the decision from the outcome. I asked him about his decision to raise his daughter in central downtown Chicago. He said, “ We definitely didn’t get the outcome we wanted.”

I asked, “Do you regret the decision?”

He said, “Oh, no, it was a good decision.”

I said, “Wait, wait, wait. But you didn’t like the outcome?”

He said, “Those are two different things. We made a wise, intelligent decision using the best of our knowledge at the time. It wasn’t an off the cuff emotional decision.”

Kimo described off the cuff and emotional as signs of bad decision making – a decision without even trying to gather more information. A decision we make quickly have this moment of decision be over. That is a bad decision, even if it ends up surprisingly having a good outcome.

Kimo’s decision to raise his daughter in downtown Chicago didn’t yield the outcome he wanted, but it was a good decision. I found that a fascinating idea.

I wish that you, or I, or somebody will soon popularize that and make a catchy way to help us remember that when we’re assessing a good or a bad decision.


You are one of the most relaxed, smart people that I know. I’m sure that those who are listening can sense the soothing, calm, quality to your voice. From my experience intelligence and calm don’t go hand-in-hand.

How do you cultivate calm in your life? Are there any practices you use that might be helpful to others?


For one, it’s my nature. I’ve read a few different books on the subject of happiness in people, and I remember reading that our happiness is 50% genetic. It’s a roll of the DNA dice. The other 50% is of your own volition, your own choices in life. I got a lucky roll of the dice. I’ve always been a happy person, but I also think a lot about how to be happy.

The conclusion I’ve come to so far is that it’s all about eliminating obstacles. I woke up yesterday morning thinking about how I’m here in a little house that I did not expect to be in, in a place I did not expect to be in. Part of me would like to be somewhere else.

Then I thought, “But I’m happy here.” This is me at 5:30 A.M. thinking, “Why am I happy? I know why I’m happy. Because there are no obstacles.”

If I lived right next door to a paper mill that was spewing smoke into my window, that would be an obstacle to my happiness. If I was in a place that was unbearably hot and had no air conditioning, that would be an obstacle to my happiness.

If I was living upstairs from some party people who wouldn’t stop making noise all night, and I couldn’t sleep, that would be an obstacle to my happiness. But as long as there are no concrete obstacles, then I can be happy just about anywhere.

If something’s troubling me, I usually stop and ask myself, “Is this real, or is it a memory or a prediction freaking me out?” People get freaked out about images in their head that aren’t even real. Either they’re picturing a prediction of something they think is going to happen, or they’re remembering something that did happen and putting a spin on it. They’re just reacting to images in their head.

But if you stop and look around at your physical environment and ask yourself, “Am I in physical pain right now? No. Then what’s really wrong? Nothing. I’m in a room. I have a roof over my head. I’m able to move my limbs. I’m fine.”

My definition of happiness is that it’s the state when nothing is wrong. That being calm, relaxed, and happy is the default state when nothing’s wrong. I think a lot of people are always asking themselves what they need to add to their life to be happy. They look to blogs and podcasts or even shopping sites to tell them what to buy.

A common podcast interviewer question that I hate is, “What’s an item under $100 that’s improved your life?” No! Don’t ask that. You’re trying to appeal to this side of people that thinks, “Ahh, I have this thing now. Now I can be happy.”

Instead, look at what you can remove from your life. Don’t add, subtract. Look at the obstacles in your life, whether it’s people in your life who are a source of misery or things that are preventing your physical comfort. Look at physical obstacles.

Somebody once asked Lee Kuan Yew, the founder of Singapore, what he thought the biggest technological innovation was in the last 100 years – it could have been the automobile or anything, but he said, “Air conditioning.”

The audience laughed, and he said, “I’m serious. Singapore was an unbearable place to work before air conditioning. Now, with air conditioning, we’re one of the most prosperous countries in the world because we can throw ourselves into work without dripping all over and feeling miserable and exhausted.”

Something as simple as air conditioning can be the key to living a fulfilled, self-actualized, prosperous life [laughter]. Don’t ask yourself what you should add. Think of what you could subtract in your life that would take away the obstacles.

Being calm, relaxed, and happy is your default state when nothing’s wrong.


I encourage everyone to check out Derek’s very minimalist website, which I think exemplifies removing obstacles [laughter].

This was so much fun. Thank you for joining us. If people want to get in touch with you and want to check out your work, what’s the best way for them to do that?


Go to

My favorite thing is when people introduce themselves and say, “Hello.” My email address in on the site. Click contact and send me an email and introduce yourself.