The most important decision I made in my twenties (to quit my secure job working for the federal government in Washington, DC, and move to San Francisco to start writing) pissed off my boss and my parents very nervous. But it also led to me writing a book, getting a book deal, building a profitable speaking business, and becoming much happier. If you’re making people around you nervous, you’re probably doing it right.
I look back and realize that if I had kept my capital and invested it in index funds, and continued to work, I would now have so much wealth that I would never have to work again. I could live by taking such a small piece of the gains in the assets that the principal would continue to grow at a faster pace than inflation. I also recently realized that if I had left all of my wealth in the original company that it came from, I would now have around $35 million.