Derek Sivers

Interviews → Long Distance Love Bombs / Jeremy Goldberg

Big fun questions. Five types of thinking and how to improve them, achieving success and motivation, deliberate daydreaming.

Date: 2020-05

Download: mp3



Earlier, my girlfriend asked, “Who are you talking to you today?”

I said, “Derek Sivers.”

She said, “Who’s that?”

I said, “He’s a big thinker, writer, dreamer type of guy that used to have a business that he sold for a bunch of money. Now, he’s a pensive, thoughtful Monk who does crafts and creative things.”



I like that description.

It’s cool for me to hear you say that, because when I sold CD Baby at the age of 38, I thought that I had peaked. I thought my best was behind me and that I would be forever known as the guy who made CD Baby and not much since. It was a really nice surprised that I transitioned into many other things.


It reminds me of a talk I watched with Liz Gilbert, the writer and author of Eat, Pray, Love.

She said that after Eat, Pray, Love, there was no chance her next piece of work would ever attain the commercial success of that book. She was in a malaise of, “What do I do now?”

What did you do after you sold CD Baby?


I drifted for a year and a half. I wasn’t sure of what I wanted to do. Then, I had a flash of inspiration to do what I’m doing now. I went about it in a very deliberate, methodical process.


You’re a very thoughtful person. You’re also a systems guy, right? I know you have a computer programming background.


Mainly, I have a background in music. I learned programming out of absolute necessity. Now that I know how to program, when I’m faced with a problem, I think, “I not only want to solve this problem for myself, but how can I solve it for the world?”

I want to build systems to solve a problem. It’s fun to think about making systems that everybody can use.

That type of thinking came after I started CD Baby. I made CD Baby just for me.

I built this a little storefront to sell my own CD on my band’s website. It was only out of necessity. Then musicians kept asking me to sell their CD, too. I thought, “How do I turn this into a system?”


You unintentionally created a business?


Yeah. Even when it was clear that I had started something, I considered it a hobby. I was doing it for free. I wasn’t charging any of the musicians. I felt that I was giving back to the music community. Only after about 100 musicians came my way and I started to work on it full time, I thought, “I better start charging something for this.”

Charging money was an afterthought. Business was an afterthought. I was just giving back to the music community.


When I work with clients as a coach, I try to help them see things from a different perspective. I help them recognize that our brain is doing things without our control and that we can reclaim our power and see things differently.

How do you get better at thinking?


I think about this a lot. There are different types of thinking. For example, short-term versus long-term thinking. Are you thinking in terms of this week, or in 50 years?

This type of thinking is also a way of asking, “What do I want now?” versus “What do I want most?”

There’s also fast versus slow thinking. Do you go with your quick instinct, gut feeling on something? Or do you lean towards slow, deliberate consideration?

There’s also fixed versus fluid thinking. I like this one a lot. Fixed thinking is when you think that people and things are just the way they are. It is what it is.

Fluid thinking is when you see everything as temporary and malleable. You think, “This is the way it is now. But everything can be changed.”

There’s also analysis versus creative thinking. Analysis thinking is when you dissect a frog versus creative thinking where you invent a new amphibian.

That type of thinking is related to truth seeking versus option seeking, which is another way of saying reductive versus expansive.

When you’re truth seeking. You’re being intentionally reductive. You’re trying to figure out. You think, “Yes. But what is the answer? I need to boil it down. Let’s remove these options that don’t feel right. Let’s answer these questions.”

Option seeking is the opposite of boiling it down. It’s splattering the situation onto the 20 walls, or deliberately adding options, or deliberately not answering any questions and only asking more questions.

Option thinking is dear to my heart. A lot of people are trying to figure out the answer to things, especially if you look at the history of philosophy.

People are often saying, “I’ve got the answer. This is it. This is what life is all about.”

That’s no fun. That’s not interesting or true. No matter what they say, there is no one answer. I much prefer to play with all the options.


How does that affect your day to day experience?


It means I’m not a leader because a leader, by definition, has to be easy to follow. A good leader of a project would say, “We’re doing this. This is our project. This is our outcome. Let’s get to work.”

Whereas an explorer is somebody who goes off into the darkest jungles of Peru and has no idea which way they’re going, they’re doing it to explore.

I’m exploring. I don’t expect anybody to follow me. I’m not being a leader. I’m off exploring different options over here.


As an explorer, you post your findings online for people to devour, and ironically, you do have followers.


If somebody finds my explorations interesting, then that’s the physical metaphor of the adventurer that’s off in Peru who sends back tales of what they’ve found, but not expecting anyone to actually do what they’re doing.

On the other hand, some people say, “I found the way. Everybody follow me. This is the way to be.”


How is your relationship with authority?


Take a guess [laughter].


Not so not so grand?


Not so grand.

I don’t even follow my own authority. If I declared something to be true yesterday, I may rebel against my previous self today.

I didn’t answer the second half of your question. You asked about different kinds of thinking, but you also asked how I get better at thinking.

Speaking of exploring versus leading, it helps to know what kind of thinking is needed for your current situation.

Don’t let anybody else tell you how you should be thinking. Nobody knows your scenario better than you do.

Are you in a short-term or a long-term decision-making mindset? Which is more appropriate right now?

Sometimes you shouldn’t be making long-term decisions. You only need to decide something for today – not forever.

Sometimes you really need to solve something in one minute. Somebody is waiting on you and they really need an answer this instant.

Other times you can ask yourself, “Does this person standing in front of me really need the answer today? Can I sleep on it?”

Usually you can sleep on it. We can all think a lot more slowly and carefully than we usually do.

Have you considered every option and now you can start to boil it down?

Or is now a better time to keep considering more perspectives?

As soon as people come two options, they say, “I have these two options. I’ve got a dilemma and I need to decide.”

No, you need to add 12 more options first before you consider that decision. Don’t stop when you’ve come up two options.

The most important thing that distinguishes good thinking from bad thinking is jumping to conclusions.

What we often call being “stupid” is people who jump to conclusions. They have one quick thought and declare that to be the answer because it’s the first thing they thought of and they don’t like thinking.

People try to decide before they get all the facts. Instead, it’s much healthier and smarter to go beyond the first, second, or even third thought that comes to mind.

Ask yourself more of these creative questions like, “What’s the opposite of that? What would be outrageous? What’s the everything option? What’s the nothing option? What’s the go insane option?”

Lastly, stepping outside yourself is extremely useful.

When I’m trying to decide something, I’ll deliberately impersonate one of my heroes. I’ll ask myself, “If I were to call this legendary person that I look up to so much, what would they do? What would they suggest?”

Or you can put yourself into a character like Spock or Data from Star Wars. Pick a character that’s purely rational and thinks emotions are strange. Ask yourself what Spock would do.

Imagine being that purely rational, unemotional person that looks at the facts and ignores all the emotion. Role playing is a great exercise.


I’ve heard a similar example where you create a board of directors for your life.

Periodically, you sit down with them. You get to choose who’s on the board. There’s power in creating a good board and having a diverse set of opinions, backgrounds, and emotions.

You should choose people that can see your situation from very distinctive perspectives.


I often consult a grumpy rabbi. After living in New York City for 10 years, I imagine a rabbi with the long beard and he’s busy and grumpy.

I come in trying to describe my problem and he looks at me, “Have you considered this book? Why not do the obvious? Why did you do this?”

I like the idea that this guy isn’t my friend. In fact, he doesn’t care about me. He just wants me out of his office [laughter].

I find that useful because he’s not taking all of my emotions into consideration. That’s sometimes the problem.

We depend too much on friends and our friends care about us. They take our emotions into consideration. We often need somebody who’s not taking our emotions into consideration and is able to look at the situation.

We need someone who will say, “Remove yourself from this equation. The answer is obvious.”

That’s what the grumpy rabbi does for me.


There is power in having somebody who is totally unattached to your relationships and your perspective on the world. They can help point out alternatives.

I read your book, Anything You Want. You have a section where you talk about creating a business under many different scenarios.

You say, imagine you had to create a business in six months? Go!

Imagine you’re backpacking in Thailand? Go!

Imagine if you knew everything would always work out? Go!


I do that a lot. That’s a perfect example of what I meant when I said don’t stop at two options. Keep going. Think of alternate scenarios.


That’s one reason why people feel stuck. They think there’s only two or three options available to them, but they don’t realize they have an infinite amount of choice.


If nothing else, add “Do nothing,” and “Go crazy,” as your next two options [laughter]. Keep brainstorming.

I could move to Iowa and start a carrot farm. I could change genders and move to New York.


To succinctly wrap this topic up, it’s about recognizing that there are different ways to think about life.

There are ways to consciously think differently about certain situations based upon an internal evaluation of what’s required at that time.


Keep a little checklist in your head of the different ways to think. Long-term versus short-term, fixed versus creative, dissecting versus creating.

Try all of them on, because we often get stuck into one habitual way of thinking that we’re used to.

Deliberately, even if you have to pull up a checklist, look at a different way of thinking of it.

Ask yourself, “What would my 90-year- old self want? What would what would be the better decision for my great grandkids someday?”

Deliberately mix up the way you think about the world. Put on a different tune. Change the music in your head.

Next, do you want to talk about how to control your mind, so that your mind doesn’t control you?


You said that in such a such a creepy voice [laughter]. You sound like a villain in a movie.


[Laughter] When Jeremy asked me if I wanted to do this interview, I asked, “What do you want to talk about?”

The first thing he said was, “How do you control your mind, so your mind does not control you?”

I had to laugh at this. You realize it’s a funny question, right? Your mind is controlling your mind. There’s no one else here.

I have this image in my mind of a dog with its leash in its mouth walking itself.

One tangent that makes me smile is knowing that the brain named itself.


[Laughter] I like that.


That’s not a word you learn right away in a foreign language. I wonder what the word “brain” is in Turkish and Hindi and Finnish. That would be fun to find out.

Circling back to controlling the brain. My advice is, don’t try to control it. Observe it. Watch your mind and see what it does. Most importantly, let it talk. Write it down and let it all out.

Your brain has a lot to say. We often feel that we need to shut up our brain and solve all our issues, but your brain won’t shut up until you’ve let it speak.

I journal for hours a day, and that’s why. Most importantly, once you’ve let your brain have its say, doubt it and question it. This is my favorite thing.

I am such a skeptic. I don’t believe a word I say. If my mind says, “I want to be a millionaire,” or “I want to be in love,” my next thought is, “No, you don’t. Let’s tear that apart.”

No matter what you’ve stated as your truth, ask yourself, “What’s the opposite of that? Could the opposite also be true?”

Then ask yourself, “What’s the real point of that?”

Once you get to the real point of it, ask, “Was all that stuff in between really necessary? What’s a more direct path to what I’m really after?”

Sometimes you might get stuck on a thought like, “I need a swimming pool in the shape of a unicorn because that’s what my hero has,” but all you really want is just tranquility.

Challenge your preferences. If you keep saying that you want a long-term relationship, ask yourself, “What if I really don’t want that? How would that look if I decided I don’t want that?”

This process works for negative thoughts, too. If your mind keeps saying, “That person wronged me. They are so wrong!”

Be a skeptic and doubt that too. “I doubt that they were wrong. Let’s tear that apart. What if I’m actually so powerful that I made all of this happen and I made that person act the way they did? What if this whole thing is my fault because I’m a superhero that doesn’t realize it? I woke up and stretched my arms and accidentally knocked down a skyscraper [laughter].”

What if you created all this destruction in your life that you keep blaming others for?

Don’t believe a word you say. I like the physical metaphor of picking up a geode or a gem and looking at it from all different angles. Hold it upside down, hold it up to the light, look through it, flip it upside down.

It has a very different shape from each angle. You might even realize that your gem is made of paper and you can fold it into any shape you want.

You can talk yourself into beliefs that empower you and help you take the actions you want. You can also talk yourself out of things that don’t empower you.

Acknowledge that you have many different selves inside of you with many different conflicting desires. I talk about this with friends a lot. A voice inside of you grabs the mic and says, “I want adventure. I want to travel the world.” You talk for hours to whoever will listen about your plans for adventure.

A week later, another voice in your head speaks up and grabs the mic, “I want security and stability. I want commitment.”

You may plan to buy a house in a smart neighborhood that you can stay in for decades and plant down roots in.

All of these desires are true. You want both. This is where it gets annoying for friends who listen to you often.

They’ll say, “You want one thing one week and then you want the opposite the next week.” It sounds like you’re changing your mind, but the truth is, you want both things.

These desires are conflicting, but they’re both true. You have many selves. You have to decide what to do it. I see this a lot with people who want to start a business, but they’re also really scared to start a business.

People often ask me how they can get over their fears. My response is, don’t get over your fears. Acknowledge them. Let them speak. Let all those fears voice their concerns and heed them.

Same with people who want a committed relationship, but they also want the variety of having different loves in their life. Both of those feelings are true.

You don’t have to declare of those feelings as “wrong.” You have different sides of yourself and you need to acknowledge this.

Give yourself time for the other voices to speak up because they don’t all grab the mic at the same time. Sometimes it takes a week.

When you’re in the throes of excitement about your plans to travel the world, it may take two weeks for that quieter voice to speak up and acknowledge that it actually doesn’t want that and is a little embarrassed to say so.

Never hush those other voices in the name of consensus. You don’t need to make your different selves agree. You can acknowledge that they disagree and address them and let all the voices have a chance to speak.


If we accept that our identities contain multitudes and that they’re all liars, how do we move forward?


It’s often by circumstance. Look at your situation. This is a perfect time to say this, because we’re talking in May 2020.

There are a lot of people who had very different plans four months ago than the ones they’re doing right now. Some people have had to completely change their plans based on our current situation.

I heard from some people that four months ago, they quit their job to travel the world, and one month into their travels, all the airports are closed.

When these things happen, look at your current situation and say, “No matter what I said before, now the situation has changed. What do I want in this situation?”

Brainstorm many different options. I often end up picking the option that makes me jump up and take action. A good goal makes you take action in the present moment.

If one of your voices has an opinion or a plan that makes you jump up and take action, doing something is usually better than doing nothing. Start trying things in reality instead of in theory.

After you consider your values and different perspectives, lean into those “aha!” moments and feelings of excitement as a guidepost or a breadcrumb towards where you’re supposed to be.


Yeah. Nice summary.

When I’m playing out hypotheticals for myself, I don’t separate thinking and feeling. When I think about different options, I pay attention to how each of them feels in my gut.


You mentioned that you journal for several hours a day.

Do you have a specific process? Why and how do you do it?


I journal in times of decision. I write when I’m wrestling with a situation and trying to figure out what I think about.

When I was 44, I found myself wishing that I could go back to ages 29-38.

I looked back at my daily diary from then to see if that was I as happy as I remember. My memories are getting blurry with time.

For 20 years, I would only turn to my diary as a way to sort out my confused or tangled thoughts. When I look at my past diaries, all I see are dilemmas that I was trying to work through.

I wish I had journaled more about the mundane. I wish I had written on a day to day basis, and said “Here’s what I did today and here’s how I felt,” even if it was only a few sentences.

Today, journaling about the mundane doesn’t seem important. But your future self might wonder how you were feeling back in 2020, or how you were feeling when you met your future spouse, or how you were feeling when you first made that cross-country move.

It wasn’t until I was 44 and wished that I had done it in the past. That’s when I started doing it. That was six years ago. I’m 50 now. Every day, no matter what, I put aside a little time just to write what I did that day.

I write down some thoughts or feelings and emotions.

After a few years of doing that, I found that there were some topics that kept coming up over and over and over again.

I had thoughts on Singapore because I was trying to decide if I should move back there. I kept coming back to that idea in my diary. Finally, I thought, “I should really organize all of my thoughts on Singapore in one place. So, I made a new folder called Thoughts On.

I started a new file in there called Singapore.txt, and I stamped the date. Anytime I have more to say on the subject of Singapore, I time stamp the document and I start writing in that one same file.

Then I can go review my history of my thoughts on Singapore. Once I started that, I made a Thoughts On file for everything. For example, thoughts on movies, thoughts on getting a dog, thoughts on Erika, thoughts on parenting.

Now I write in my Thoughts on folder and my daily diary. With my diary, I open up a plain text document and start dumping my mundane actions and thoughts into today’s diary. But when I’m recurring back to something, I go into a separate Thoughts On journal for that subject.


You’re very much a systems guy.

I imagine that your Thoughts On journal is a really good folder for blog posts.


Of course. When I’m sitting there exploring a thought and asking myself questions, sometimes I think, “Wow that’s really interesting!”

Then I start a new file which may turn into a blog post because it’s usually a topic that applies to other people, not just me.


To give the listeners a little background, you are a slow thinker and you like time to consider ideas so that you feel prepared for conversations.


Everyone thinks I’m brilliant in the moment. [laughter].


Because of this, I sent you a couple of questions beforehand. The third question was, what does a successful life mean to you and how do you get there?


I’m so glad you asked this. I had never actually thought about it. Here’s my direct definition of success, debuting on


Goldberg’s podcast.

Success means nothing more than feeling proud.

Since it’s a personal feeling, nobody else can tell you what success is. So Maybe you only need to make $100 doing something you love. Maybe success is having a healthy and happy family. Nobody else can tell you otherwise because it’s whatever makes you feel proud.

Success doesn’t necessarily mean taking action. It can be stopping an action. You can successfully quit drinking and that can be a big success.

You could change the way you’re thinking so that you’re at peace. Even though your actions haven’t changed, a shift in your mindset can be a success. You can successfully get over a bad breakup.

By that definition, when you asked me how you achieve that, I thought, “Make yourself proud. Whatever that is for you.”

If you tell yourself, “I’m going to make myself proud,” usually something comes to mind. It’s usually doing the difficult thing, but the right thing.

Lastly, you have to know whether you’re driven by satisfaction or dissatisfaction. If you want to make yourself proud, you could lower the bar all the way so that the tiniest little thing makes you proud. But that’s only if you are motivated by satisfaction.

If satisfaction motivates you, then lower the bar all the way down so that you have daily wins and then raise it bit by bit so that you can feel successful the whole time.

If dissatisfaction motivates you, then what you need to do is raise the bar so that you don’t feel successful until you’ve achieved this really difficult mission. This comes up a lot when I talk with friends about trying to achieve something.

I often recommend raising the bar all the way and many friends say, “No way. That that sounds horrible!”

I realize they’re not driven by dissatisfaction. This is a person that wants to feel success along the way and that actually motivates them more.

Some people are only motivated by raising the bar so high that they prefer to stay in a state of dissatisfaction until they get their success. Those people are usually dissatisfied with their life, but also proud of it.

When I lived in Singapore, I had a very wise Scottish friend. I mention that he’s Scottish because outsiders often have the best insights into a local culture of a place.

I mentioned something about how Singaporeans always complain. He said, “As I’ve traveled around the world, I’ve noticed that the places that are the most dissatisfied and complaining are usually the most prosperous ones. The places that have an attitude of ‘Don’t worry, be happy, enjoy the day,’ end up being the least prosperous ones. They may be happier, but they don’t progress as fast.”

For example, he pointed out that Chileans in South America are always dissatisfied, but they are more prosperous than its happy-go- lucky neighbors. I found that really interesting.

This goes for people too, not just cultures. If you’re not satisfied of quality of your work until it’s an absolute masterpiece, then you’ll hammer away and practice into the night until it’s perfect.

Whereas somebody who has a mindset that their work is good enough, they may happier, but the quality of their work might not be as good as that person that remains dissatisfied.


I’m thinking of this as a formula. Success = Pride + Dissatisfaction

It’s an interesting idea to accept that a successful life requires dissatisfaction on some level.


Only for some people. Many people would be so demotivated by constant dissatisfaction that they would quit. They need daily or weekly wins to feel that they’re on the right path.


It’s a spectrum.


Yes. You have to know your preference and what works for you. Usually by trial and error. There’s a massive difference between theory and practice.

First, go to one of those countries that’s really laid back and chilled out and everybody is super stoked. They think they’re successful. Then, go to Chile and see it through a new lens.

I have never been to Chile, but I always think of Singapore as a great example. They have an amazing and brilliant government. It’s genius and yet Singaporeans are still not satisfied with it. They still hold it to higher standards and say it’s not good enough, even though it’s amazing.

But that’s what keeps pushing the Singapore government to continue to get better.


I suppose some level of contentedness or wellbeing relates to where you draw that line on that spectrum.

If you are perpetually seeking and not obtaining, then you’re going to be dissatisfied more often than not. Your life might suffer in some sense.


Maybe, but let’s go back to the original definition. Success means nothing more than feeling like a proud individual.

Success is not a subjective matter. It’s totally up to you. If the person hanging out on the beach in Sicily is happy with their life, then who cares that the people in Singapore are making more money?

By that person’s measure, they are successful because they’re proud of their life and what they’re doing.


I want to amend my formula. Another potential element could be honesty.

I mean that from a deeper sense of authentic truth. Ask yourself, “Am I really proud of this life or am I using this life to hide from the things that I truly desire? How do I really want to show up in the world?”


It’s interesting that there are people who have millions and millions of dollars and don’t consider themselves successful enough yet. They’re still not proud enough of what they’ve done.


How have you dealt with the comparison trap?


I’ve always felt so removed from the game of society’s norms that I never really measured myself by everybody else’s measures. I don’t consider myself to be playing the same game.

I’ve never needed to impress others. I live in a tiny little empty home. I’m happy with it. I don’t care what it looks like from the outside. That’s why a lot of the decisions I make it seem weird. I don’t care to follow the norms.

I get a deep sense of pride knowing that I’m not doing the normal thing. I’ve made up my own measures.


What are some examples of things that you’re proud of in your life?


I’m proud of my mental shuffle of rethinking things. I’m proud that I didn’t get sucked into following the norms. That mindset came from being a long haired, rebellious musician at the age of 14 and deciding that I wanted to go be a rock star. In high school, I never felt that the stuff I was being taught applied to what I want out of life and that set me on a good path.

When I was about to go off to music school, I had a great music teacher who taught me that the way they teach things in music school was moot and that I was much smarter than that. He told me to ignore the curriculum and go make things happen.

At every step along the way, the rewarded message and common theme was that the typical rules don’t apply. I’m proud of myself for sticking on that path. I created my own way of looking at the world.

Nothing has any inherent meaning. We project meaning onto things if we want. People often project meaning onto things because they’ve heard other people do it and so they do it, too.

If you’re able to shake it off and start from scratch, you can realize that nothing has any inherent meaning. For example, my friend was shocked that I didn’t call my mother on Mother’s Day. Hallmark invented that holiday. Sorry, your guilt isn’t working on me.

Societal norms say, “You must do this, and you must do that.”

But I think, “No, I don’t think so. Someone made that up.”

Another example is the notion of countries. Europe is considered 35 countries and India is considered one, but it could have been the opposite.

This whole mentality of “That’s them and this is us. We’re going to keep you out of our country,” reminds me of kids playing hot lava with the floor.

“Alright, I’m going to draw this line and you can’t cross the ground now. It’s hot lava.”

“That’s Canada now. That’s Belgium.”

[Laughter]. Somebody made this up.

Yeah. That’s so true.


As an American during a global pandemic, it feels so surreal that there are parts of Earth that I can’t go to just because of a line on a map.


Somebody asked me once, if I could have any physical thing in the world, what would it be?

I said I wanted a universal passport so that I could have the legal right to live in any country in the world.


Freedom sounds like it’s a core value for you.


Yeah. And options. My favorite option is the option that gives you more options.


Question number four. What’s your advice for people who are struggling with presence?


When you emailed me about this question, you said people are struggling with presence, they’re anxious about the future, lost in the past, et cetera.

I love that you put it that way. Being present is one of many options. It’s not your only choice, and it’s not always the correct choice. You get to make your own virtual reality in your head.

You can go somewhere else in your head and take a trip anywhere you want. You can immerse yourself in videos from that place. I actually go to YouTube and watch videos from a certain place. I’ll go read a book from that place and vividly imagine myself there so that I actually forget that I’m in my own bedroom.

You can deliberately daydream. You can visit the past on purpose. I have a couple really happy memories that I’ll revisit if I’m having a hard day or need help sleeping.

I’ll put myself in that moment and or replay that movie a few times. I’ll make it bigger and more awesome than it even was. I will vividly and deliberately immerse myself in the past.

You can practice counterfactual thinking this way, too. You can think about how things could have turned out differently in the past.

Your imagination is so amazing. You can make many possible future you want. Don’t ask yourself, “What’s my ideal future?”

That’s a dangerous question because it limits you to just one. Instead, I love coming up with ten different futures to please the different sides of my personality.

Part of me really loves this daydream of finding a really nice, safe, secure place in Golden Bay, New Zealand, right there in between two of the best hiking tracks and one of the most beautiful, wonderful, safest little nooks of the world.

But another part of me really wants to go fully nomadic and adventure around the whole world and get to know it all.

You can daydream about an overwhelming, adventurous future and also daydream about a sweet, romantic future. Do this one at a time. Don’t confuse yourself too much with. You could daydream about the last thing that anyone ever expected of you, or a future where all of your dreams come true.

You get to make up scenarios for yourself. You could ask, “What would I do if I got a hundred million dollars tomorrow? What would I do if I got paralyzed tomorrow? What would I do if I became famous tomorrow and suddenly everybody in the world wanted a piece of me? How would I react to that? How would that be?”

I know this is going to sound bleak, but it’s not.

I’ve been deliberately picturing a worst-case pandemic, dystopian future. I picture the worst doomsday scenario and ask myself, “What if we never find a cure? What if we’re never able to go out again? What if travel is eliminated completely?”

Then I ask myself, “How could I thrive and be happy even in that scenario?”

That question leads me to reflect on, the minimum I need to be happy. I broke it down and came up with four things. As long as I have these four things, I’m good. I really don’t care what happens in the outside world that much because I know I can be happy even in that dystopian future.

My point is that being present is overrated.

Don’t struggle to be present. Instead, feel free to deliberately daydream.


I’m curious, what are your four things?

Number one is quiet. I’ve noticed that as long as it’s silent, I’m happy. Number two, we take it as a given, but climate. It would be hard to be happy if I was freezing and shivering and huddled in front of a fire. It would be hard to be happy if I was dripping with sweat because it was unbearably hot. As long as I have a decent climate I’m good.

Number three is that I want to live near nature of any sort. It can be a city park or a massive forest. I spend about one or two hours a day walking around forests and fields. That’s a major part of my daily happiness.

Number four is to have a comfortable home with a view. Even if I in a quiet, climate-controlled jail cell that was near nature, I would find it hard to be happy with no windows.

My eyes get blurry and really messed up if I can’t look more than 20 feet in front of me. I’d like to live in a place that has a window where I can look outside and see something that’s more than 20 feet away.

Those are my only four criteria. If I have those four things, I’m good. It’s nice to know your minimum. Because once you’ve got those things, everything else is just the icing on the cake.

Then of course, you can build upon that and go fight for whatever you feel like fighting for.


It’s not a matter of needing more, it’s a matter of needing less.


I think a lot about what I would do if I got 100 million dollars tomorrow.

It’s a folder in my Thoughts On journal because it stumps me every time. I think, “What would I do if I had 100 million dollars tomorrow? What would I buy? What would I get? What would I hire?”

I get so stumped because I think, “Wait a minute, I don’t want a big house. What would I do with five bedrooms? I’d have to clean them. I’d have to buy stupid furniture to put in them.” No matter what material object money can buy, I immediately think of the downside.

Even when I think about hiring somebody, then I realize that I’d have another person’s expectations on me. I’d have somebody else that I’m responsible for.

I always come back to the same conclusion to give it all away.


I think we’re kindred spirits. Do you mind mentioning what you did with the money after you sold your business?


Sure. Go to to read the full tale.

In short, I had a letter of intent with the company that was buying my company. And we had an agreed upon price of 22 million dollars. At the time I had no debts. CD Baby was already profitable. I already had a few million dollars in the bank. I was the sole owner. I had no investors. It was free and clear. I didn’t need 22 million dollars and I didn’t even know what the hell I was going to do with it.

I mentioned that to my lawyer who had a background in tax law. He was a really nice, good guy. I told him, “I’m going to give it away to charity.”

He said, “All of it? How serious are you about this?”

I said, “On a scale of zero to 10, it’s a 10. I’m absolutely 100 percent going to give it all away. I do not want it. In fact, I think it would be harmful for me to have it in the bank. I think it would burn a hole in my pocket. I would do stupid things.”

He said, “If you’re really serious about this, we’ve got time to restructure this deal before it happens. You can set up a charitable trust. You can transfer the entire ownership of the company into the trust and then it’s gone. You can never, ever, ever get it back. Even if the sale falls through, that company is gone. Now it belongs to charity.

Assuming the sale goes through, then the purchaser will buy CD Baby from the trust and that entire 22 million dollars will go to charity.

If you keep it in your name, the 22 million dollars is going to come to you. 7 million dollars will go right back out to the IRS and only 15 million will go to charity.”

I said, “I want the whole 22 million to go to charity. I don’t want it to ever touch my hands.”

He said, “Are you sure? Sleep on this for a week. Tell me next week.”

A week later, I was still sure of my decision, so we set up The Independent Musicians Charitable Remainder Trust. I loved this idea so much because that money came from musicians and now will go back into the circle of life to fund the next generation of musicians.

When I die, it’s going to all go back to music education to help train the next generation. That plan made me deeply happy. I can’t even say I’m that super proud of having done it. It was just the right thing to do.


I think we need more people doing more good in the world. So, thank you for that.

Derek, I so appreciate your time. Thank you for coming on. This was fascinating and I’m sure has resonated with a lot of people. You have a very incredible mind and your voice is like a soothing, warm blanket [laughter].

Several times I found myself looking out the window at massive tree and then having to snap back and remind myself that I’m not listening to a podcast, I’m hosting a podcast.


I don’t mean to have a soothing voice, but ever since I was a teenager, you don’t know how many friends have literally fallen asleep on the phone with me while we’re talking [laughter].


You need to make a sleep meditation.


When I ran CD Baby, I would listen to every single album that came through the door.

We would listen to the albums so we knew how to categorize it, how to rank it, and how to link it to other things.

We had a category of people that made meditation albums. I’d listen to the soothing music and then sometimes, they would have the most annoying voice.

[Starts speaking in a nasal voice] “Imagine yourself as a ball of light.”

I’d think, “You really need somebody with a different voice!”

By the way, thank you for asking some really fun, deep questions. And thanks for having me on.


You’re very welcome. I appreciate you being here.