This is a fun read - I've been working from home for a software company for the past 4 years, so it is interesting to read about other experiences or advice for accomplishing this. I've found that lots of the big, stable software companies are flexible on working remotely, as long as your role and manager support it (and not just software engineering roles allow for being remote). If you don't want to freelance or bounce around, but still want flexibility for working location, it's really helpful to work in the office for some period of time (few years, perhaps?) and then try to shift. Even though I think productivity can actually increase while remote, I do not think I would have been able to ramp up or grow as quickly without the foundation of a few initial years of face-to-face interaction with other teams and the management above me.