In this Deep Dive I have a conversation with my friend; entrepreneur and author Derek Sivers. Some of the highlights of our discussion can be found below, as well as time-stamps if you fancy listening to us talk :)

Derek is an American writer, musician and entrepreneur who founded CD Baby, an online CD store for independent musicians, back in 1997. He sold CD Baby in 2007 and has since embarked on other ventures including writing 4 books including Anything You Want - one of the three books that I've listed as having changed my life.

πŸ™πŸΌβ€β™‚οΈ Derek Β πŸ’» Website / 🐀 Twitter / πŸŽ™Podcast

πŸ“šDerek's Books:


00:45 – Background and Career
02:00 – Anything You Want Book Discussion
03:00 – Writing a Book
07:00 – Fear of Plagiarism
09:35 – Advice on Writing, Apps and Productivity
16:05 – Current Books Being Written
19:00 – Building Your Own Store
24:20 – Do What Makes You Happy
27:30 – Avoid Quoting From Other People
32:50 – Identity: Music and Being A Doctor
37:20 – Music Theory: Is it really that valuable?
44:45 – Musical Originality
46:05 – Derek’s Singing Journey
50:15 – Ali’s Singing Experiences
53:00 – On Making Friends
55:45 – What Does Friendship Mean?
59:40 – Vulnerability, Exposure and Making Friends
01:07:00 – Talking To People On The Phone
01:08:45 – The Famous Broadway Musical Composer…
01:13:35 – Weird Like Me, Shared Experiences and β€˜Burning The Ships’
01:20:00 – Connecting With People and Strangers
01:23:20 – Replying To Everyone
01:28:30 – Replying To People Asking For Advice
01:33:20 – Imposter Syndrome
01:35:10 – Goal Setting in Life and Business
01:42:45 – The Most Powerful Thing to Remember About Goals
01:45:30 – Closing Thoughts

Highlights From Our Discussion

Life Advice Quotes

There’s more to life than efficiency – sometimes you do things just because you love doing them. I’m very process driven – I do things for the doing rather than the goal.
When you do what makes you happiest, it puts fuel in your tank. If you are just trying to optimise everything for analytical returns, yes it may be optimised but you might not be excited to get out of bed every morning. Whatever excites you the most, that’s what you should be doing.
When deciding what to do in life, I find it helpful to ask what do I hate not doing? If I was to remove everything, what would I hate not doing the most?
It’s always easier to give advice than to take it because you’re detached – you’re seeing it from a distance. By giving someone else advice, you are being your highest self because you are emotionally detached. In other words, giving advice puts you in your highest self and you can take your own advice later.

On Writing

  • Some people think writing a book is big, daunting prospect but it’s better not to think in terms of a book but rather in terms of ideas that you want to share.
  • Limit yourself to one idea per article and share the articles in public as you go. Eventually your articles will form the basis for the chapters of a book after having had exposure and feedback from the initial public exposure in the form of the article.
  • Writing offline is essential – when it’s time to write, actively turn off your internet so that you cannot go online or get distracted and the you write. We all have a habit in the modern world of thinking that we need to look something up but then you fall down a rabbit hole and then you’re not writing. When you think you need to look something up, just add it to a to-do list somewhere else.
  • We don’t NEED apps – any form of text editor that gives you the space to write your thoughts is as good as any app. The desire to find apps to increase our productivity, paradoxically becomes the enemy of productivity.
  • Avoid quoting people or listing long bibliographies before you get to a key point. The idea is not to hide the source but just not to force t upon someone who didn’t ask for it. Imagine if it was the norm that every time you ordered a meal at a restaurant the chef would come out and explain the heritage and history of every ingredient – it would be quite strange! If you want to know you can ask, but it’s not the norm – the same philosophy can be applied to this idea of quoting people appropriately.

Key Quotes

One idea per article ensures that each idea gets a spotlight.
Writing offline is my biggest productivity tip. When it’s time to write, go over to your modem and turn it off.
I personally see apps as the enemy. I use a text editor from the 70s. When someone says you need a certain app – no you don’t. People used typewriters and before that a pen – we’ve coped without apps for hundreds of years.
The desire to find apps is the enemy of productivity.
Real professionals don’t hide behind their tools – real professionals use what’s around them. It’s the amateurs who try to nerd out about their tools - it's all a distraction from really doing the work.

On Music

  • Music theory is akin to grammar in language. Many living languages have never codified their grammar but still exist without getting analytical about them. Music theory can be viewed through the same prism – it always comes later and isn’t necessary for the learning or playing of music.
  • To analyse music, make up your own system for reading. The reason we have sheet music was to make universal standards but on a personal level, you’re not going to be writing out music for orchestras and so you should create a system for yourself.
  • Learning an instrument or learning to sing is easier when you enjoy doing it for its own sake – that it’s process driven rather than just a goal.
Music theory is like language grammar. If you were to ask a linguistic, they would tell you that there are about 6000 languages in the world but most have never been written and therefore most languages today haven’t codified their grammar but people learn to speak them well anyway without getting analytical about them. They just listen and speak. I think it’s the same thing with music theory – music theory always comes later. It’s absolutely not necessary to the playing or learning of music.
My best advice would be to make up your own system for writing it. You can take your favourite songs and make your own system for analysing them. Just notice and pay attention to the organising and layering of tracks and instruments. Just to see the way that instruments are dropping in and out of a song can be abstracted to use for your own song.

On Making Friends

  • Don’t be afraid to reach out to people, you probably have a lot more in common than you might imagine – just be cautious about putting that person up on a pedestal too much because you are implicitly putting yourself in an inferior position.
  • We all have phones, yet we rarely use them for their overriding raison d’Γͺtre – to phone people!
  • We feel one way about something and we assume other people feel differently about it – if a friends was to call us, we are generally delighted to speak to them and yet we have concerns of calling them ourselves for fear of disturbing them.
The word friend is too vague – it should have many sub-divisions.
Just because someone is smart, and a good conversationalist doesn’t necessarily mean they are good friends.
The real friends provide emotional safety. I can have good conversations with strangers but there is a tight inner circle of people you feel emotionally comfortable with that you could call when you are really down and you will know that you will feel safe to be not your best self.
I really like the phone – my five best friends are in five different countries. The phone is crucial to me – if someone doesn’t like the phone then they’re only going to be C level friends.
You should reach out to people that you feel a connection with. You probably have a lot more in common than you think – the reason you were drawn to their work is because it resonates with you.
You don’t need to text somebody to ask if they can talk – the sound of a ringing phone is the inquiry as to whether someone can talk.

On Goals + Metrics

Obsessing about metrics is like obsessing about the odometer or fuel efficiency on a car – it’s not wrong but it’s missing the point of why you got the car in the first place.
One of the most powerful things to remember about goals is that goals aren’t there to shape the future. The future doesn’t exist – all that really exists is the present moment and your memories of the past.
A goal is only a good goal if it makes you take action in the present. If a goal excites you and makes you take action in the present, then it’s a good goal. If it doesn’t, then it’s not a good goal for you.
Goals only exist to change your present actions for the better.