Derek Sivers — Podcast — Making It with Chris G.

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One of my favorite things in life is having conversations with people that challenge the way I think and inspire me to break old habits to explore new ways to approach different situations in life. Derek Sivers has become one of my favorite thinkers when it comes to living a fulfilled life, breaking the habits of how we are “supposed to” do things, and living outside of the box, really never even allowing yourself to be in the box in the first place. One of his first ventures was the pursuit of becoming a professional musician, playing multiple instruments at a very young age. Eventually his journey lead him to the Berklee College of Music in Boston, and shortly after joining a circus as ringleader/MC musician.

Derek was a professional touring musician, who was looking for a way to release his music online. At the time, the only way artists could sell their music online was being on a major label, or a label that had distribution through a major. This inspired him to the creation of CD Baby in 1997, which for the first time gave all musicians an opportunity to release their music online, and has become the biggest distributors and seller of independent music. In 2008, Derek sold CD Baby, giving the proceeds to a charitable trust for music education. Since, Derek has written several books, articles, frequent TED Speaker, has become a master programmer, philosopher, teacher, and inspiring creative thinker.

In this conversation, you’ll learn about Derek’s story, philosophies and strategies on how artist can approach the music business in new and creative ways, and much more. It’s such a gift to have Derek on the podcast, and to share this conversation with the world. My tagline for the podcast is “go see shows, meet people, make stuff.” I hope this conversation inspires you to go make stuff and pursue the things that “interest you the most at this moment.”

Quotes from Derek Sivers
“I like the idea of your site as the definitive source of information about you.”
“It feels kinda cool, punk, and indie, to just do it myself.”
“When I look back at my career, so many great things happened because I was right there in the game. Right there in New York City where everything is happening.”
“It’s a huge benefit, it’s actually still underrated benefit, to be in New York, LA, and maybe Nashville.”
“When you go to these conferences you’re meeting people who are usually in the game right now, making things happen right now.”
“Hell, yeah or no is a mindset to use when you’re already successful and you’re overwhelmed with opportunity.”
“Have your shit together so that when you’re encountering people for the first time, it shows that you’re serious, you got it going on.”
“Always do whatever is interesting you the most at this moment.”
“For most of us what you need is right there already in your head and in your fingers, and it’s just a matter of mastering distraction.”
“Whoever works the hardest and work the smartest and master distraction instead of having distraction master you, that person is going to win.”
“Real change will feel like it’s not you. You’ll be acting like someone else. It will feel weird when you’re doing it right.”
“You have to try everything yourself. Feel the pain of making mistakes, and then feel the deep happiness of coming out on the other side of something difficult.”
“The fountain of youth is to make more mistakes.”

Highlights from this Episode
[4:00] About Page and What I’m doing Now page
[7:35] What’s happening NOW with Derek Sivers
[11:36] Getting started in his Music Career
[15:15] Working at Warner Chapel Music
[19:35] Pursuing a Music Career in today’s Music Industry
[25:00] Moving to New York or Los Angeles, and Conferences
[27:36] Training your personal Self-Awareness
[30:33] Saying Yes
[33:11] Hell Yeah or No
[36:20] Tasks musicians can outsource
[38:58] Building your team – Strategies on how to get peoples attention
[44:10] Derek’s writing process
[51:20] Building your craft with experiments
[55:13] Experiments in personal life
[57:25] Writing and telling your story
[1:04:10] Getting unstuck from your current season
[1:07:20] Imitating your role model
[1:11:35] Note taking from reading books
[1:14:35] Mentors
[1:18:30] Advice for parents looking to build a creative environment
[1:27:00] Getting to Know Derek Sivers - Quick Questions