Two opposite mistakes nearly destroyed the same company

Derek Sivers spent his first three years running CD Baby answering every question himself, from seven in the morning to ten at night, seven days a week. Someone would ask whether a customer could change album art after it had gone live, or whether they could combine two orders to save on shipping, and it all went through him. He hit a breaking point, stopped going into the office, and realized he had to make himself unnecessary to the business. So he started gathering employees around every time a question came up, answering it, explaining the reasoning behind the answer, and having someone write both the answer and the philosophy into a manual. After two months of this, the questions stopped. He moved to California to make it obvious that running the place was no longer his job, and over the next four years the company grew from one million to twenty million dollars in revenue while he stayed almost entirely out of it.

That looks like the whole lesson: delegate everything, trust your people, walk away. But Sivers ran into the failure mode on both ends of that idea, and it nearly cost him the company twice.

First, he handed the entire digital delivery system, the part of the business that got music onto iTunes and other stores every week, to one employee, trained him carefully, and then stopped checking. Months later he discovered that albums hadn't been delivered anywhere in weeks, because the employee had quietly fallen behind and never said anything. Sivers had trusted completely and verified nothing, and the company's reputation took real damage before he caught it.

Then he overcorrected. When employees asked which health plan or profit-sharing structure to choose, he told them to decide entirely on their own, every time. Months later his accountant asked if he knew his employees had voted to give themselves all the company's profits. He had handed over so much authority that he'd effectively surrendered it, a mistake he later learned has a name: to abdicate, meaning to give up power entirely rather than share it. The result was a company of eighty-five people who saw him as an obstacle to be removed, not a leader to consult.

The uncomfortable truth Sivers draws from both failures is that delegation isn't a single move you make once. It's an ongoing balance between trusting people enough that they can act without you, and staying close enough that you'd actually notice if something quietly went wrong.

Pick one recurring decision you're still making yourself and hand it to someone else, but explain your reasoning out loud as you do it so they understand the philosophy behind the choice, not just the answer. Ask that person to write down what they learned, so the thinking survives without you repeating it. Set a simple, recurring check-in, not to redo their work but to verify that the most important commitments are actually being kept. And before you hand over a decision that affects everyone, like money or benefits, decide in advance which parts are genuinely theirs to choose and which parts you still need to weigh in on, so generosity doesn't quietly turn into an abdication you regret later.