Here’s how to live: Be a famous pioneer. - Derek Sivers

When talking with people, ask deep open-ended questions — like “What’s your biggest regret?” — that will lead to unexpected stories.
When ordering in a restaurant, ask them to surprise you.
When doing creative work, let the random generator make your artistic decisions, shaking up your usual style.

Being stupid means avoiding thinking by jumping to conclusions.

Every year or two, change your job and move somewhere new.
Change the way you eat, look, and talk.
Change your preferences, opinions, and usual responses.
Try the opposite of before.