Episode 19: The Surprising Benefits of Working Weird and Awful Jobs (ft. Derek Sivers)

February 28, 2024

About the Episode

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.

About Derek Sivers

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.

Derek Sivers Quotes From the Episode

I never work for money. Nothing I’ve ever done has been for the money. Any job I took, it was only if I would have also done that job for free.
When a gig comes up that you want, don’t be casual. Go fucking over the top, all the way, maniacal until you get the gig, because that’s what you have to do to prove that you want it.
When you’re early in your career, just say ‘yes’ to everything. Because you never know what stupid little thing is going to lead to a bigger thing.
You can make yourself a job. It doesn’t matter if they’re hiring or not. If you go to them and show them that you can make them more money, you can make things happen.

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