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 $75 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 ⇨ Sign up for my newsletter, Your Next Breakthrough. It will help make you a less awful person: ⁠⁠⁠⁨https://markmanson.net/breakthrough⁩⁠⁠⁠ ⇨ Get clarity on what actually matters. Try Purpose, Mark's AI mentor app that learns your patterns, challenges your blind spots, and helps you take action. Get started at ⁠⁠⁠⁨https://bit.ly/4w46FMH⁠⁠⁠ FOLLOW MARK Mark's IG: ⁠https://www.instagram.com/markmanson⁠ Solved IG: ⁠https://www.instagram.com/solvedpodcast/⁠ Twitter: ⁠https://x.com/markmanson⁠ LinkedIn: ⁠https://www.linkedin.com/in/markmanson/⁠ YouTube: ⁠https://www.youtube.com/@IAmMarkManson