Derek Sivers

Interviews → Misfits / Bryan Victor Lim

48 rapid-fire questions about dating, Singapore, value, and life

Date: 2020-04

Download: audio (mp3)

Link: https://bryanvictor.com/2020/04/23/derek-sivers/


Bryan:

Why start doing podcast interview again? 

Derek:

I enjoy the questions, and coming up with new answers each time.

Bryan:

Why say yes to my podcast invite, when you have turn down 4 other people?

Derek:

I care about you. We’ve been emailing since 2016 and I’ve been excited to see your path.

Bryan:

Why not talk about virus or business?

Derek:

I have nothing new to say about those things.

Bryan:

“The woman I was madly in love with married the guy she would always complain to me about.” Did you get divorce twice? What’s the story and what did you learn from it? https://sive.rs/loss 

Derek:

I’ve been married twice, but neither one was a decision to spend our lives together. Both were just documents to let us be together over international borders.

Bryan:

Anything we should prep before marriage? Prenup?

Derek:

You don’t really know a person until you’ve seen them lose their luggage. Go have adventures together. But also have monotony together.

Bryan:

What do you like about “Models” by Mark Manson and where is it lacking to a fulfilling relationship?

Derek:

It’s not lacking anything. It’s the wisest, most philosophical book for men about women.

Bryan:

How does a programmer (aka Derek’s) system to dating before? 

Derek:

No, I have no system for that.

Bryan:

How much should you trust your feeling when you pick a wife/partner?

Derek:

Feelings change over time. Trust time. Don’t pick until you’ve spent time.

Bryan:

When is it a good time to break up with someone? 

Derek:

When you don’t want to improve the relationship.

Bryan:

What are 3 interesting things you’ve learnt about sex.

Derek:

1. Everyone’s approach is different

2. You have to communicate

3. Some people physically click physically even if they don’t emotionally or intellectually

Bryan:

How did you became resident in Singapore? Did you give up on your US citizenship? If not, how did you get a Singapore citizenship?

Derek:

Financial investor scheme. I applied for Singapore citizenship, but it is still pending.

Bryan:

What surprise you about Singapore after you lived here?

Derek:

How many Singaporeans told me they didn’t follow their dream to be a musician or artist, but instead did what their family wanted them to.

At first I thought this was wrong, but now I understand better.

Bryan:

Tell me more about Singapore Government? What the role of government (in general and in Singapore)? 

Derek:

When people say bureaucracy anywhere else in the world, we assume it’s a bad thing.

But Singapore’s government is so well-run that bureaucracy is a good thing.

Learning how the government is run is like looking under the hood of a Ferrari. It’s a very impressive machine.

Bryan:

“Singapore was founded on the ideals of the Age of Enlightenment”? Why do you say Singapore is influence by confusician-ism? 

Derek:

The “age of enlightenment” quote I got from the Discovery Channel documentary about Singapore.

I don’t know much about confucianism, but the thing I said earlier about people doing what is best for their family or even their country, instead of only following their individual preference.

Bryan:

Who do you think are the govt system designers? 

Derek:

I don’t know.

Bryan:

How’s mentoring in EDB, Spring and ACE? What did you do? What is your role as a mentor?

Derek:

It was ten years ago, so I’m sure it has changed much since then. I just helped judge startup competitions, and met with many many young entrepreneurs wanting to start a business, to help give suggestions.

Bryan:

Who are 3 interesting/memorable person you’ve met in Singapore?

Derek:

1. Meng Weng Wong

2. Pete Kellock

3. Lucian Teo

Bryan:

How do you disagree well (define) and make people see that own bias without being defensive? When you are asked a loaded question, what your method of answering?

Derek:

I’m happy to say I disagree with the question.

Like if someone says, “How can we get over our fears?” I’ll say, “No. You shouldn’t get over your fears. You should get under them.”

Bryan:

Why did you think that Seth told you to sell (“if you care, sell”) your company? Looking back, would you say the same to yourself then?

Derek:

I was doing a dis-service to my clients by remaining the leader of a company that I didn’t want to improve.

And yes, it was great wise advice.

Bryan:

Through your relationship with Seth Godin? What did you learnt from Seth Godin? What makes him special?

Derek:

He’s surprisingly wise, and incredibly gracious and encouraging. He makes others feel special.

Bryan:

How did you settle your $3.3million dollar mistake? https://sive.rs/mistake

Derek:

I didn’t. It cost me $3.3 million and that was that.

Bryan:

Would you be open to talk about these and your lesson? https://sive.rs/loss

Derek:

The hardest times are when you learn the most. Don’t wish not to have them. Don’t avoid mistakes. Just make sure to reflect on them and learn from them.

And write in your journal every day, so your future self can look back to see how you really felt then.

Anything that feels like a huge problem will be solved and forgotten in 10 years or even 1 year.

Bryan:

In the context of life, where do you think “feeling” stands? Should we use it at all to make decision? How?

Derek:

I believe two conflicting things.

1. Our emotions contain the wisdom of everything we’ve learned. So trust your feelings, because it’s the summary of all the facts. Read “How We Decide” by Jonah Lehrer about this.

2. Our emotions can be easily manipulated by yourself and others. So don’t trust your feelings. Perhaps even deliberately manipulate them to match the facts. Watch “How to Hypnotize Simon Pegg” by Derren Brown about this.

Bryan:

Do you feel that you know yourself? What are the best tools (80/20) to know yourself. Why?  How does one learn about themselves? 

Derek:

I know a lot about myself, but the unconscious things are still unconscious.

Write write write privately. Journal. Diary. Ask yourself questions. Then question your answers.

Most importantly, observe your behavior. What you SAY doesn’t matter, really. It’s what you DO.

Bryan:

How do you define personal value? How did you found yours? Learn - because you “Need” to keep being surprise - or is it a “want”? And why create? 

Derek:

Values change depending on your situation. If you’re lacking money, you may say money is your top priority. But if your health goes bad, suddenly health is your top priority.

So it’s interesting to note which values seem to always be there for you, no matter what happens in life.

For me it’s learning and creating, but for someone else it might be charitable giving, care-taking, spirituality, or money.

Bryan:

What is your monthly burn rate that you set for yourself? How do you know that is enough for you to be truly satisfied with your life? Then that you don’t need to work for money anymore.

Derek:

You have to experiment to find out. Try living well below your means, and see if you’re OK with it. It probably means knowing what’s really important to you.

For example, I’m happy eating on $5/day. I don’t care about food much. But for someone else, that would make them miserable.

Bryan:

Why do you think people ask that question - “What is the purpose of life?”

Derek:

They’re annoyed at the uncertainty of it all. They want more certainty in their life.

Also they want to know what they should be doing.

Bryan:

Why do you want to think slowly, or be un-reactive in interview? Is it the same with you in conversation with friends? Was it like that since young? If so, what made you decide to change your mind?

Derek:

It’s different when I know I’m being recorded, and it’s archived forever.

When I do things in public, I’m very aware of the microphone. I’m aware of my 200,000 followers.

If I say something into the microphone, that means I believe it’s worth their time to stop and listen.

That’s why I don’t post nonsense or lightly share random things.

Bryan:

Why do you choose to take on replying to email (550 emails a day?) more people treat it as a job?  Do you enjoy it?

Derek:

I enjoy the connection, yeah. It’s a huge sense of security to me, knowing so many people around the world.

And it’s really interesting, especially to know people from very different places or careers.

A professional athlete in Uruguay. A piano-builder in Russia. And a cool dude in Singapore getting to know the misfits.

Bryan:

Why you don’t do public speaking anymore? You don’t like the format or the reach is not enough?

Derek:

Even as a musician, I’ve always been more interested in recording and sharing my work with the whole world, instead of just one room of people somewhere.

I spend so much time preparing that it feels like a sad waste to have it all disappear the minute it’s over.

Bryan:

Why do you take on the label as an author? Does you hep you with your life?

Derek:

It’s the activity I find most interesting right now. So calling myself an author is a way of doubling-down on that one thing, instead of thinking of myself as an entrepreneur and programmer that does a little writing.

Bryan:

You seemed to be very happy taking care of your son. Was it planned for? Did you knew you were selfish-ly wanting it all along? Or did you learn about your own selfishness along the way? Why is parenting selfish, ultimately? Why is taking on that view, better for you? 

Derek:

It wasn’t planned, but it’s been a nice surprise.

I don’t think parenting is selfish, no. Quite the opposite.

But I’ve found that being a great parent benefits me as well.

Bryan:

What is the 3 biggest illusion that is preventing people to be happy?

Derek:

1. You can’t help the way you feel

2. You should react to what’s going on now

3. If you add something to your life, it’ll make you happier

Bryan:

What is happiness to you? Describe the feeling. 

Derek:

It’s my default state when I’m not letting myself get sucked into worrying about problems.

Bryan:

What were 3 things you unlearn in 2019? 

Derek:

1. I thought I knew what I wanted for my future. I found out you only know by trying.

2. I thought I wanted to make music. Though my words said so, my actions did not.

3. I thought having my books translated into other languages would be fun.

Bryan:

How to be happy? Advice?

Derek:

Let go of goals.

Bryan:

After since arriving at UK, what surprised you? (It’s next on my list to visit)

Derek:

Absolutely nothing. It’s completely comfortable and unsurprising in every way.

Bryan:

What email delivery software do you use?

Derek:

I wrote my own. A little Ruby script that queries my PostgreSQL database, and sends the emails directly from my server.

Bryan:

What contact software do you use? What your system of implementing this? https://sive.rs/hundreds

Derek:

I wrote my own. Mostly in the PostgreSQL database, with Ruby doing some web app wrapping around it. I’ll make it open source some day.

Bryan:

How do you make night mode on your site?

Derek:

That’s just one line of CSS:

@media(prefers-color-scheme:dark){}

That lets the user decide on their device if they want to switch to night mode.

Bryan:

What is currently the top 3 most useful idea, product, software in your life now?

Derek:

Idea: expect the worst and make peace with it.

Product: the weight rack in my garage.

Software: the PostgreSQL database.

Bryan:

Whats the idea behind the “how to live” book? How are you writing it? Personal? Why save them into a book? 

Derek:

There’s a great book called “Sum” by David Eagleman that answers the question, “What happens when you die?” - but with 40 different conflicting answers, one per chapter.

I love that format, so I thought it would be fun to answer the question, “How to live?” - in 27 different conflicting answers, one per chapter.

Each chapter completely convinced it has the answer to how to live, but it goes completely against the previous chapter.

Then I was surprised and thrilled to find one grand conclusion. But that’s a secret until you get the book some day.

Bryan:

How do you get a dot org domain? 

Derek:

Register it anywhere.

I have sivers.com and sivers.net too.

But “.org” has a historical use for non-profit organizations, and I wanted to make it clear that sive.rs was personal, not commercial.