Hi, Derek. Welcome to the Flowgrade Show. I’m really excited to have you.
Thanks, Max. Me too.
We’re meeting digitally for the first time. But what if we had run into each other in a cafe in Munich, which I know you considered moving to at one point?
I probably would have asked, “So what do you do in life?” What would have been your response?
If I wanted to talk to you, I would probably call myself an author now. But that’s a pretty new thing for me.
On the other hand, if you were a stranger, I would respond differently. I have enough social interactions in life. I’m a pretty social guy.
If a stranger asks me, “What do you do?” I usually don’t want to get into it. So, I just tell them I’m a programmer. I’ve found that it’s the most wonderful answer because if I say I’m a programmer, people tend to go, “Oh.” They have nothing more to say about that.
I was a full-time musician for around 15 years. If I say I’m a musician, people ask, “Oh, my God, what kind of music do you do? Where can I hear your music? Are you on the radio?”
I think, “Oh, never mind.” So, I started saying, “I’m a programmer.” It’s a wonderful way to shut people up.
You just mentioned you’re a jack of many trades. It’s amazing how many interests you have and how much curiosity you have for the world.
It tends to go in phases.
I don’t think I’m actually a jack of many trades. I spent 15 years of my life just doing music – massively, singularly obsessed with making music. And then I accidentally started CD Baby.
As soon as I started CD Baby, my attention shifted. I think it was like somebody who goes from being a basketball player to a basketball coach. It’s like you’ve had your time in the spotlight. You’ve had your time on the court. Now, it’s your time to coach others.
My main focus in life shifted completely. As soon as I started my company, I instantly poured all of my attention into helping musicians. I never wrote another song or ever made music again.
I tend to get very single-focused. But I guess that’s what we’re going to talk about – flow. That’s why I’m here.
Was there a point when you realized, “OK, my music career is now over, and I’m going a different direction?”
Imagine you’re walking by a lake for a long time, and you come up to a great mountain in nature and you say, “Oh, I’m going to climb that mountain.” You’d probably be halfway up the mountain before you go, “Huh? I guess I’m not next to that lake anymore.”
It wasn’t a conscious decision. I never thought, “I am no longer going to make music, just like you wouldn’t decide, I am not going to walk by that lake anymore.” Instead, you’re just focused on something more exciting.
We are actually right in the middle of the first topic that I wanted to inquire about, which is how to deal with time.
I recently came across a quote actually that made me think of you. It was by Ram Daas, the late and great thinker who once said, “If you want to live high, you have to live outside of time.”
All of a sudden, you popped into my head, and I thought about how you make decisions on moving to different places. For example, it seems that you move just because you feel uncomfortable – not based on any time frame. Especially now, I think that a lot of people are being thrown into totally different lives. Time becomes a new concept for many of them.
And as someone who plays around with time a little differently, my first question is: What role does time play when you go about your day, when you work, when you make plans?
I think it’s kind of moot. We’ll talk about it from two different aspects.
For work, I don’t work with a schedule or deadlines or really any structure at all. Instead, I throw myself completely into whatever project is the most important to me next. I do only that. Whether that project takes me three days or three months or three years to finish, I do that one single thing until it’s done.
I’ll give a concrete example. Until Christmas this past year, from the end of March until Christmas, I was doing nothing but writing my next book every single day, like fifteen hours a day. But at Christmas time, my assistant told me that she was stuck waiting for some technology things that we needed on our back-end system that she couldn’t really work without.
I went, alright. It’s clear that right now this more important than me finishing the book. She’s unable to work. So, from Christmas until just three weeks ago, I paused my book and I threw myself into programming. I woke up and did nothing but programming all day long until I fell asleep.
Then three weeks ago, when the COVID thing was really starting to affect people’s lives, I did something I’ve never done before. I sent an email to my entire mailing list of tens of thousands of people. I just sent three sentences. I said, “How are you? Are you OK? Yes, I’m really asking.”
Around 6000 people replied, and I went, “Oh, God.” So, for the last three weeks, until two days ago, I did nothing but answer about six hundred emails a day for 15 hours a day. I did that for 15 days until I was done.
That’s the role time plays in my life. I don’t look at clocks. I don’t have a schedule. I don’t have a structure to my day. I tend to throw myself into one thing at a time.
Now, that I’ve answered all those e-mails, I’m going to go back to finishing my book as I was doing before Christmas.
That said, I don’t think this is the best way to be like. Ideally, I wish that I would stop for two hours a day to practice my Portuguese or work on my book for four hours every morning first and then throw myself into answering emails or programming. But I have this thing in me where I don’t like it when things are incomplete.
When I’m in the mode or in the flow, I get so into one thing that everything else I ever did in the past is just gone. I’m not thinking of it.
I said we’re going to talk about two aspects of this. The second one is parenting. I had a kid eight years ago. When he was born, I was spending all my time with him. I thought about this whole concept of clocks. It’s a recent, kind of artificial invention. This whole idea of it’s one o’clock, you should go to bed. It’s seven o’clock, it’s time to go to sleep.
It’s so silly when you look at it through the lens of nature and kids’ natural flow of being tired or being enthusiastic or whatever. So, ever since he was born, whenever I’m with him, all devices are off. All clocks are moot. We just hang out and go by whatever timescale he’s feeling.
I think that was a good inspiration for my own life, too. I realized the clocks are only needed when you need to coordinate with other people.
That’s exactly the anxiety that I get usually when I leave my calendar. Being German, we’re a very calendar conscious country. People are afraid of letting go of the linear time.
I’m also someone who’s loses track of time often and my colleagues and friends know me for that. You recently recorded an episode that really resonated me, called “Time is Personal.”
It was right before the New Year and you said you’d rather focus on special events than calendar dates or holidays.
How do you deal with the expectations that the outside world has of you in terms of your calendar? How do you get out of your calendar and not feel anxious about it?
Number one, try to avoid situations where you’re expected to do something on a certain calendar date.
If you adjust your life in a way where you can say, “This will be ready when it’s ready,” people learn through reputation and reliability that you will get it done within a reasonable amount of time.
It’s not going to be done by one o’clock on Thursday. It’ll be when it’s done. I’m lucky that nobody in the world, except maybe tax payments, are expecting anything by a particular date from me. I try not to make those promises.
Right now, there are only two things that I put into my calendar for the last 10 years – flights and interviews. Those are the only two things where I have to be somewhere at a coordinated time.
For the last six years, I was living in New Zealand raising a kid. I wasn’t flying anywhere, and I didn’t do any interviews, so I didn’t even own a calendar. The calendar app on my phone had no entries, and I never looked at it.
But, when I was in college in Boston, I owned an executive planner with every hour of every day scheduled out and I loved it.
If I had one hour in between classes, I’d say, “OK, that’s an hour. I’m going to work on my jazz piano scales.” If had two hours here and I’d say, “I’m going to go running for one hour. Then, I’m going to practice my arpeggios.”
I actually really liked living that way, and I got so much done. I made so much progress in my life that I’ve considered doing that again, but I haven’t. I’m always so into what I’m doing right now that I just really enjoy doing everything to completion.
As a musician, you deal a lot with rhythm in music.
In life, do you have any routines that help you establish a daily rhythm and build momentum?
No. Off the top my head right now, rhythm and momentum feel to be in conflict. The way I describe my workflow is more like a drone than a rhythm [laughter]. I just do one thing. I have no concept of time.
My advice is, try to do things to completion because then you don’t lose the momentum in the first place. It’s hard when you’ve switched your attention to something else, and you have come back to your original project.
If I look at programming code that I wrote even a few months ago, I think, “Did I write that? What is that? What the fuck is that about?” It takes me almost a full day or two to go, “Oh, right. I haven’t looked at this in a few months now. I remember what that’s doing. That’s why. . .”
I end up having to write documentation for my future self to tell my future self. It’s like I’m writing to a stranger. But that stranger is my future self. Same with writing my book. I don’t know if you had that experience writing your book. When you’re deep into writing, there’s a flow, but if you do something else for a while, it’s really hard to put yourself back into that mindset.
That’s exactly what I feel when I’m in a flow state. When I’m writing, I’ll realize at 3 a.m. that it’s dark outside. I have no idea what time it is.
To me, this is momentum.
I used to go back and forth between Singapore and the US and I dealt with jet lag a lot. At some point, I decided not to fight it. If suddenly I was falling asleep at 5:00 in the afternoon and waking up wide awake at 2:00 in the morning, alright. I’m going to roll with it. I’m not going to beat myself up. That was where my energy was, so I’d get up at 2:00 a.m. and start working.
Eventually, things fell into place. But I think there’s a lesson in that, even for those of us who aren’t jet lagged. You should go with your natural energy. If you get tired at three in the afternoon and don’t want to work, that’s a good time to do nothing for half an hour.
You need to be quite in tune with your immediate emotions and what you want.
I think a lot of people struggle with not knowing what they should be doing at the moment, or what they actually want to do.
Isn’t that related to what it means to be in-flow? Mihaly Csikszentmihalyi wrote a book called Flow. I love when he says that flow means we know what needs to be done next. That is the most crucial thing for me, and what I wrestle with the most. If I know what needs to be done next and it’s within my abilities, then then I stay in flow.
When I don’t know the next step, I get stuck. When people say, “I don’t know what I’m doing with my life,” by definition, that’s the enemy of the flow state – not knowing what’s next.
So, first you have to figure out some way to figure out what’s next and then you can throw yourself into it.
When something intuitively feels good, even if you can’t really rationally explain it yet, I tell people to keep going. Keep doing more of it, and then you usually get deeper and deeper into a flow state.
That happens to me when I’m writing my book. I’ll have an idea and then I end up writing a different chapter than what I intended in the first place. I’ll lose myself in this new concept. At the end, it somehow fits in even though I couldn’t explain that rationally at first.
Do you know that experience?
Ideally, when you’re writing, it’s best when it’s discovery. You don’t want to sit down and just spit out stuff you already know. That’s a chore.
But when you sit down to write and you’re discovering new things as you’re writing, that’s exciting. I found out that the original meaning of the word essay is from the French word, essayer, which means to try, or to attempt. I love that.
Michel de Montaigne started this idea of writing essays while he was figuring out what he thinks about something. It was writing as exploration.
By the way, you recently had a project where you wrote a new article every day.
I read your summary where you mentioned that it became a chore. I mention this this project because it seems that this got you out of balance and out of your flow state.
When you get out of flow, what are your go-to methods for getting back into a productive state?
I’m a little embarrassed of that. When I started out writing an article a day, I didn’t think it was going to only be for 30 days. I thought optimistically that I would do this permanently and make it my top priority. This is my job. I’m going to write a new interesting article every day. And after 30 days, I wasn’t able to get much else done.
I don’t write quickly, I write very slowly. So, I was spending five hours a day on one article.
I’ve described to you the way that I like to work. I love to do one thing at a time. Suddenly, every single day was split into parts. The first three to five hours of the day, I was trying to write my article that I promised the world I would do.
Before the experiment, I would post an article on my site and it was a rare event. I’d announce the article, everybody would read it, and I would get 350 comments on it. But with the new articles, once I was posting every single day, some of them were getting three or four comments. I thought, “Wow. I’m trying harder than ever. And people are reading less than ever because I’m just writing too much.”
As for you question, how do how do I get back into flow? It’s about finding the next step. Whenever I find I’m not in flow, I have to ask myself, “What is the next step?” I’ll get very meta. I’ll go into my journal and ask myself questions.
“What am I doing? Why am I doing this? What’s the ultimate outcome? Where am I at in the process? What’s what are the big steps? Which big step am I on now? What are the little steps? What is the next little step and what is the next little step after that? Is it small enough for me to handle or am I stuck because it’s too big? Do I need to break it down smaller?”
That usually helps me figure out, “OK. Right. I now remember what I’m doing. Now I know the next step.”
That brings me to another idea that you put into my head. This idea to write your own autobiography starting with the last chapter.
How did you come up with that idea? And have you already written your autobiography?
It’s not done.
Actually, there’s very little of it done because I’m still 3/4 of the way done with my next book called, How to Live. I want to finish that first. But how cool would it be to keep writing your autobiography your whole life? When I say, “You’re always writing the last chapter,” I mean that you don’t number the chapters in advance. You say, “OK, whatever phase in my life I’m in now, this is the part that I’ll be writing.”
You have to go back and fill in the backstory, so you write backwards. You could start with right now and fill in the past, or if you have plenty of time, start writing from the beginning. The idea is that you don’t stop at the age of 40, 50, or 60. You keep adding to it so that when you die, the book is ready to go, even if you are mid story.
You could be mid-sentence and if you die the next day. Well, that’s the end of the book. Leave instructions on how to release the book. How cool would it be to have the book in a state of constant completion and it could be released the day after you die?
It’s a very intriguing idea. With my second book, I started writing the last chapter first to see what I wanted readers to feel like when they have read the whole book. It really helped me get motivated and start writing.
Cool. It’s a great approach. I’ve never heard that.
You just mentioned your newest book project, which I’m really excited about, called How to Live.
It’s a really interesting concept. Can you tell me the story of how you came up with this project and share a little bit about what we can expect as readers?
It was inspired by a book called Sum by David Eagleman.
I think David may have gotten the format from the book called Einstein’s Dreams. The idea is that every single chapter is just a two- or three-page short story about what happens when you die.
But each one deliberately conflicts with the previous one.
When you die, you’re surrounded by a bunch of thuggish little creatures looking at you saying, “What is answer? What is answer?”
You find out after a while that what you knew of as your life was actually an artificial intelligence program. You are an artificial intelligence program that they wrote to go figure out the meaning of life. Now, that the program has stopped running, they’re trying to get the answers out of you. So, you try to tell them what you learned about life.
But every time you tell them, they just looked at each other with furrowed brows and say, “What is answer?” You realize that if we were to write an artificial intelligence program smarter than us, we would be too dumb to understand its answers.
That’s it. That’s one of the chapters. Then the next chapter will say:
When you die, you’re greeted by a handler that who tells you in your last life you chose to be a man. But once again, you can always choose whatever creature you want to be. Every time it’s your turn to live again, you get to be whatever creature you want. You remember a wonderful day you had as a man when you watched a horse grazing in a field. You admired its simple life, just eating grass in a field. You say, “You know what? I’d like to be a horse.”
No sooner said than done, you start to feel your arms change into legs and your hands turns into hoofs. Your neck lengthens and your muscles change.
But then, you start to feel your brain turning into a horse’s brain. You’re starting to forget what it feels like to be a man. You realize, “Oh, no. What I loved was being a complex man, appreciating the comparatively simple life of a horse. But if I don’t even know what a man is anymore. I won’t appreciate my simple life. I’ve made a horrible mistake!”
You say, “Wait!” But all that comes out is [horse sounds]. And at the last minute, before you completely turn into a horse, you have a horrifying thought which is, “I wonder what kind of beautiful, complex creature I must have been before I chose the simple life of a man?”
They’re beautiful, short stories. It’s a gorgeous, brilliant creative format to write a book with forty conflicting answers to the same question. While I was driving, I thought, “Oh, my God, I want to write a book called How to Live. Every chapter will deliberately conflict with the previous one. It’ll be 40 answers to one question, “how to live?” If one with disagree with the previous one.
I don’t know if there will be 40 answers. It’ll probably be more like 25 answers.
But what’s so exciting about it, and what I’ve discovered while writing, is that there are many completely valid and true approaches to life. They conflict with each other.
You could say rightly that the way to live is to delay gratification. You should live for the future. Your present self should be in service of your future self. You should always work towards making a brighter future. Both for yourself, for your kids, for your grand kids, for the world. Defer all gratification in order to make the world a better place. Look at the magic of compounding interest and use that as your guiding law of physics. You can elaborate on that infinitely.
That’s just one idea. A minute later, you could argue, here’s how to live:
Fill your senses. We’re only on earth for a short time. See everything. Hear everything. Taste everything. Go do it all. Go everywhere. If you really believe that this is the correct way to live, then you’re going to need a system. Never listen to the same thing twice. Never go to the same place twice. Never eat the same thing twice.
If you’re going to do that, well, then you might as well have one of these guidebooks like, “1,001 Places You Must See Before You Die,” and systematically go to all those places. Find the best food in the world. Listen to the best music ever made, but never more than once, because there’s always something more to be listened to.
It keeps going and going, and each one of these answers conflicts with the other.
It’s fun to write because every single chapter, I get so into that philosophy that I think, “Oh my God, this is the way to live.” Then I finish that chapter and it’s on to the next chapter, which is completely in conflict with the previous one. It’s a blast.
During the current situation of Covid-19, have you changed your perspective on life at all? Has this inspired one the answers in your book?
To me, the different approaches to life all exist in my head at the same time. So, I don’t think that something would happen in the world to make me say, “This is now the right one.” I disagree with the idea of the “right” approach to life.
Stoicism is a little overhyped right now, but at its core, it’s about preparing yourself for a more difficult future. So, I think that living with the unknown, where you don’t know what the future holds, it’s interesting to assume or expect the worst.
If you were expecting things to get worse this whole time and now they are, then it’s no big surprise to you. It’s not devastating. Even coming to terms with your own death.
Being deliberately pessimistic is to not look on the bright side, but to go darker and deeper and ask yourself, “What is the worst possible thing that could happen?”
Name 20 terrible things that could happen and make your peace with those things. Come to terms with the fact that the worst that could happen is not that bad.
In fact, it’s fine. And if you’re cool with that, then anything that happens is OK. When I originally sent that e-mail out to my whole mailing list three weeks ago, thousands of e-mails from people came pouring back with devastated and things like,
“Oh, my God, my father just died. Now my wife is coughing, and I can’t stop. I think she may have it.”
“I was just fired. We can’t pay next month’s rent.”
“I’m here in a strange country where I don’t have any friends and I can’t afford to fly home. I don’t know what I’m going to do.”
I found myself feeling like, “Oh man, we’re all fucked.” I shut off the computer for a bit and walked in the forest. Birds were chirping in the trees. They’re just fine. In fact, I’m just fine.
I was going through the scenarios thinking, “What’s the worst that could happen? I die. Is that so bad? No, I’ve already put my savings into a trust and I’ve taught my kid what I could, and I gave him a good life.”
What else could happen? I lose everything I have, and I fall deep into debt. Is that so bad? No. As long as I’m able to write and read, I’m happy. As long as I’m allowed to get out of the forest.
What if I lost my health and could never go outside again? Is that so bad? I’d be OK with that. It’s not ideal, but I’m cool with it.
I played through these awful, worst case scenarios in my head and made my peace with it. To me, that’s the gist of Stoicism – to both strengthen yourself for a more difficult future and make peace with the worst outcomes.
If you could plant one thought into the minds of all the listeners right now, what would that thought be?
Generosity is worth it.
Very nice. Next question. What are you afraid of?
Voters continuing to elect harmful leaders.
With what person would you like to change shoes for one day?
All of them. It’s my life’s fascination to understand what it’s like to be someone else.
Ideally, if I could trade places with everybody for a day, that would be my favorite answer. But if I had to pick one person, I would pick a person that seems the most unlike me. A woman in Guatemala, or Tibet, or Tokyo.
Someone who would be as culturally different from me as possible. I would love to be in her head for a day to see what it’s like to be her. To hear and understand her belief systems and values. To see the world through her eyes, and then see how people treat her so I can understand what that’s like. That would be my dream.
What do you believe to be true, even though you cannot prove it?
The future will be better than the past.
What a beautiful way to end this wonderful episode.
Yay for Lightning Round! [Laughter].
I really, really enjoyed this episode. Thank you for your time and also personally for me, thank you for all the inspiration you’ve given me as a writer and as an entrepreneur and as a human being.
So, thank you for your work. It really does inspire people. I’m proof of that, and I’m very excited to present it to my community.
The main reason I do these interviews is that I like meeting people that introduce themselves to me from across the world. It’s one of my favorite things about my inbox. I’ll get an email from a guy that makes guitar pedals in Slovenia or somebody who’s an investor in Lebanon.
So, people listening to this, please send me an email and introduce yourself. Say “Hello.”