Why Derek Sivers spent fifteen years failing at singing on purpose

From the age of fourteen, Derek Sivers wanted to be a great singer, but his pitch was off and his tone was rough, and pretty much everyone who heard him said so. He kept at it anyway: eleven years of voice lessons, an hour of daily practice, several live shows a week fronting his band. At twenty-five, he recorded his first album and brought it to someone he considered a real mentor, who listened closely and told him plainly that he simply wasn't a singer, that he should accept it and find someone who was. Sivers left that conversation unbothered. He figured he just had more work to do.

At twenty-eight, he started noticing his voice was actually getting good. By twenty-nine, after roughly fifteen years of practice and about a thousand live performances, he had become, by his own standard, a genuinely good singer, good enough that a listener meeting him for the first time later told him singing must be a gift he was simply born with.

Sivers tells this story alongside two others from the same years of his life. He wanted to learn studio production himself rather than hire a professional, even though friends told him hiring an expert would take weeks instead of years. And when CD Baby needed a database-driven system beyond his basic website skills, he bought a twenty-five dollar book on programming and taught himself, rather than hiring someone who could have done it faster.

In every case, the efficient move was obvious, and it wasn't the one he chose. He argues this only makes sense once you separate two different goals that people quietly treat as the same thing: wanting to have something finished, and wanting to be someone capable of making it. A finished recording, a working website, a successful company are all things you can have, and having them faster by outsourcing is usually the smart, efficient choice. But if what you actually want is to be a good singer, a skilled producer, a real programmer, then handing the hard part to someone else doesn't just save you time, it takes away the exact thing you were trying to gain. Sivers is direct that this cost him money and speed. His employees were furious that he insisted on doing all the programming himself well into the company's growth, certain they were losing business because of it. He was fine with that trade, because the entire reason he was doing any of it was to be happy, and doing the work himself was where his happiness actually lived.

Ask yourself honestly, for whatever you're currently trying to outsource or shortcut, whether you want the finished result or whether you actually want to become someone who can do this. If it's the second one, commit to doing the slow version yourself, even knowing it will take longer and probably cost you something in speed or money. Expect people around you to question this, and prepare a simple answer for why you're choosing the slower path on purpose. Track your progress by what you're becoming capable of, not only by what's getting finished, and let that be enough justification on its own.