He Quit His Job And Makes $10M/Year Writing Online

The Turning Point

Dickie Bush was a Wall Street hedge fund trader working 60-hour weeks, making $180,000 a year in New York City. By conventional standards, he was winning. But he watched a 37-year-old colleague ask for permission to attend his son's Little League game — and get denied. "If I do everything right for 14 more years, I might be sitting here having to ask for permission to go to my kid's little game," Bush realized. That moment broke the appeal of the trajectory he was on.

He didn't quit immediately. He considered that a mistake many people make: operating from scarcity. Instead, he started a newsletter inside BlackRock as a way to get his name out. After a few months, he realized he was capping his audience to one company when the internet could give him millions of eyeballs. In January 2020, he started writing publicly.

The Viral Breakthrough

Bush committed to a 30-day personal writing challenge: publish something every day for 30 days. "If it doesn't work, I'm gonna go have to find something else," he told himself. On day 27, he hit publish, got zero engagement, and went to bed assuming the experiment was over. He woke up to find the post retweeted by Naval Ravikant and other high-profile people. It had thousands of likes. His newsletter went from 250 subscribers to over a thousand.