The benefits of working in a distributed work environment are many. No overhead for office real estate, no employee commutes, flexible work hours, the ability to hire talent where it resides. But what are the pain points? Can working in a distributed workplace be done successfully? Workplaces often provide camaraderie; how do you get that when you’re working in isolation? How do you measure productivity when you can’t see what employees are working on? How do you ensure your employer recognizes your contributions? Since our start in August 2005, Automattic, best known for its work on WordPress.com, has employed people from all over the world. We don’t have formal offices; instead we choose to hire the most talented people to work from where they’re already located. What lessons have we learned? What should be avoided?