How did you start working remotely ?

I started to work remotely since I became an independent developer, just like creating my own company (a.k.a. consultant). This means that I can do my task anywhere. I currently work mainly at home, cafe, and bar. However, I may be able to work aside beach, on mountain, abroad if I want (and I have my strong will to work even in such places).

Some companies don't want their employees to work remotely, because they have their face to face culture (at least In Japan). They think highly of working at the same place, to create something cool. However, it is obvious that they cannot ban their outsourcings to work remotely. It is easier to be independent developer than applying remote jobs, in my opinion.

I've been a consultant most of my professional life. The majority of my customers were train- or plane-rides away. While the initial engagements were typically "on site", it made little sense to return to effect fixes that only took hours (maybe even only minutes). This meant perfecting two skills: telecommuting and/or walking people through the processes.

Other thing that being a consultant has meant is that I've worked on geographically-disbursed teams. Learning how to effectively collaborate via email, SMS, and chat is critical to success in such organizations ...and can be just as helpful when it comes to dealing with customers.

I don't work full-time remote but we have remote freedom and it all started by aspiring to let folks do so as a company. Hard to ask for that kind of stuff on your own in a lot of environments.