How Should You Plan Your Year?

Bill Perkins says his family plans in time-bucket periods rather than one someday list. While his son Kai is under five, they want to live in another country, particularly Japan, and they are deciding whether that stay is a summer, a year, or two years. The larger questions, where to settle, which culture to learn, and which activities matter, stay open. Day to day they are often catching events and moving them, because the travel schedule is already full.

Shaan Puri says he now blocks three days a year to think about how to spend the other 99 percent. He tries to picture the most exciting version of the year, puts dates on it, and then makes those dates happen. Perkins treats that kind of planning as useful. His own version is frequent talks about the long arc, not a single retreat.