The Surprising Benefits of Working Weird and Awful Jobs (ft. Derek Sivers)

Successful people talk a lot about what made them successful. But they're rarely asked about all the things that went wrong.

What about all of the things that failed? Or all the times they got fired? Embarrassed themselves? Spent time in jobs that were just plain weird or awful?

No one asks this stuff. Until now of course.

In this episode, I talk to my friend Derek Sivers about the weird and awful jobs that eventually led him to become a millionaire. From circus ringleader to founder of one the most successful music start-ups of our time, this guy has a story to tell.

Derek Sivers is the author of four books, founder of CD Baby which he sold for $22 million (then gave most of it away), and just an all-around badass.

CHAPTERS

Chapters

• 00:00:00 Introduction: The Jobs That Didn't Work Out
• 00:01:44 The Pig Show That Changed Everything
• 00:04:53 The Professional Pest: Getting Paid to Annoy College Students
• 00:08:50 Mark's Investment Banking Disaster
• 00:13:50 The Metaphorical Time Zone and Corporate Reality
• 00:17:48 Class Reunions and Working for Dreams, Not Money
• 00:19:46 Telemarketing and the Art of Not Being Yourself
• 00:24:30 Identity, Authenticity, and Cultural Differences
• 00:26:42 Mark's Three-Week Career as a Bouncer
• 00:30:07 The Value of Weird Jobs and Empathy
• 00:30:52 Comfort as a Trap and Keeping Your Baseline Low
• 00:42:22 Home as a Place With No Obstacles
• 00:34:14 Quitting the Marathon: When Goals Don't Serve You
• 00:35:25 The Landmark Forum and Life Having No Inherent Meaning
• 00:38:10 Investing in Skills Over Paychecks
• 00:31:51 The Horizon Principle: Why Hardship Doesn't Feel Hard
• 00:39:42 What Cities Whisper: New York, Luxury, and Success
• 00:48:12 Being Around Greatness: Geography and Ambition
• 00:44:22 How Derek Became a Japanese Rock Star
• 00:55:46 Alan Tepper and Creating Your Own Job
• 00:58:39 Mark's Career as a Men's Dating Coach
• 01:01:40 Transactional Thinking and Missing Father Figures
• 01:03:59 The Teacher Learns More Than the Student
• 01:06:34 Wrap-Up: Failed Jobs That Made Us Who We Are

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