How did you dive into digital nomad-ism?

Nowadays, a lot of freelancers are taking the “digital nomad” plunge and working remotely from just about any location they want. From Bali to the Santa Cruz Mountains, it seems like the ideal lifestyle, but what thought, if any, went into YOU deciding to live that kind of lifestyle? What was hard about it? Easy? What do you regret? How do you meet new people? All the questions…