Why Explorers Make Poor Leaders

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My Guest: Derek Sivers is the founder of CD Baby and author of "Hell Yeah or No" and "Useful Not True." He shared how he graduated from Cal Berkeley in two years instead of four because the "standard pace for chumps" - a lesson that shaped his entire career of institutional skepticism and unconventional thinking. From creating viral shipping emails to understanding why explorers make bad leaders, Derek shares why being busy means being out of control, how your first thought is an obstacle to your best work, and why you can't predict what the world will want from you until you try everything and listen closely to what it's telling you.

Notes:

No Speed Limit – Most things are paced so the slowest person can keep up. If you're driven and motivated, you can go so much faster than the standard pace. I graduated from Berkeley in two years by learning four semesters of harmony in one hour. "The standard pace is for chumps. You can do so much better than that."

Question the Standard Process – When someone says you must go through usual channels or something will take a certain time, assume there's probably a hack. Develop institutional skepticism - there's usually a better way than how most people do it.

Create Opportunities, Don't Wait for Them – You don't have to wait until a company is hiring. If you can see how to benefit them, walk in and show them what you can do for free first. Alan Tepper made Warner Brothers more money than anyone that year by just showing up with a plan.

Make Everything Valuable to Others – The starving artist spends all their time on work valuable to them but not to others. Use money as a neutral measure - if you can make money with your art, it ensures what you're doing is valuable to other people. "It's almost impossible to predict what the world will want from you... Keep yourself out there and listen closely to what the world is telling you it wants from you."

Stand Out by Being Different – Don't imitate what everyone else is doing. I wrote a silly shipping email in 10 minutes that became one of the most viral emails ever mentioned in business books. Ask yourself constantly: What has nobody done before?

The First Follower Creates the Movement – We focus on the shirtless dancing guy, but the first follower is what made everything happen. Until then, people kept their distance from the freak. If you find someone doing something great, follow them and show others how to follow.

Every Sentence Must Matter – My books are 90-100 pages, but start as 1,000-page rough drafts. I spend 1-2 years full-time chopping every sentence that doesn't absolutely need to be there. "I'm not gonna put a single sentence out into the world that doesn't need to be there." Make every word count - eliminate everything that doesn't add value.

Hell Yeah or No is Context-Dependent – This tool is for when you're overwhelmed with options and need to raise the bar. Straight out of college, say yes to everything because opportunities are like lottery tickets. Once something rewards you, then say no to other things and double down.

Busy Means Out of Control – "Busy to me implies out of control. You're busy if you've let other people shove shit into your schedule." Leave space instead of filling it - that time to think is what creates valuable insights others don't have time to develop.

Your First Thought is an Obstacle – Don't honor the thought that came first. In brainstorming, acknowledge the first idea, then keep going - don't stop at two or three. Even silly ideas can seed great ones you'd never reach without that stepping stone.

All Beliefs Are a Myth – People worshiped Zeus for centuries; now we call it mythology. But we say our own beliefs are true while others' are superstitions. I expected China to be awful from American news, but found it wonderful - question what you've been told.

Use Prejudice as Your Compass – If you notice you're prejudiced against something, that's exactly what you should explore. Burning Man sounds awful to me; therefore, I should probably go. Steer into your biases to overcome them and gain new perspectives.

Explorers Make Terrible Leaders – Explorers try everything and change direction constantly, which frustrates teams. Leaders go in a straight line to a clear destination, unwavering in mission even if the path changes. I loved changing my mind, which made me a bad leader until I learned the difference. Set projects with clear missions, even if you're personally exploring other things.

Try Everything Until the World Says Yes – I had a booking agency, a record label, a recording studio, and my own music - all failures. Then, a side project to help friends (CD Baby) took off. You can't predict what the world wants from you, so try many things and listen closely to what it's telling you.

1. What "standard pace" are you accepting in your business or career that you could actually accelerate if you questioned it? Where have you assumed something has to take a certain amount of time just because that's how it's always been done?
2. Are you spending time on work that's valuable to you but not to others? How could you test whether what you're creating actually solves problems people are willing to pay for?
3. Are you acting more like an explorer or a leader right now? If you're constantly changing direction, how could you set clearer missions for your projects while keeping your personal explorations separate?

Derek's Content:

• Derek's website and blog 
• "Leadership Lessons from Dancing Guy" (First Follower) TED Talk - Derek Sivers 
• "No Speed Limit" essay 

Former Episodes Referenced

• #647 - Tim Ferriss - Chasing Your Curiosity
• #562 - Nikki Glaser -  The Creative Process of a Comedian 
• #644 - Blaine Anderson - Confidence, Curiosity, Connection 

Episode Timestamps

02:20 Early Life Lessons from Kimo Williams

05:21 Corporate Lessons and Unconventional Paths

09:10 The Power of Adding Value

13:57 Viral TED Talk: Leadership Lessons from the Dancing Guy

22:03 The 'Hell Yeah or No' Philosophy

27:29 The CD Baby Experience

28:02 Starting an Online Record Store

29:10 Creating a Unique Shipping Notice

30:01 The Viral Impact of Creativity

32:53 The Importance of Regular Writing

35:17 Questioning Assumptions and Beliefs

36:23 Exploring New Perspectives

40:41 The Explorer vs. The Leader

48:21 Advice for Aspiring Leaders

Resources:

• Read: The Score That Matters
• Read: The Pursuit of Excellence
• Read: Welcome to Management
• To Follow me on X: @RyanHawk12