I've been working remotely since the beginning of this year and was having the same questions, so I approached some experienced remote workers about the challenges that they face and how they overcome them. For me the “loneliness” aspect of a remote lifestyle (lacking colleagues etc) was a bit of a concern which led me to create a startup based around that very concept! I wrote down the learning points that I picked up from these experienced remote workers here:

http://www.theremotetrip.com/2016/11/02/challenges-every-rem...

Other articles that might help you: 1. 7 Tools that will boost a remote workers' productivity on the road every day: http://www.theremotetrip.com/2016/10/21/7-tools-will-boost-r... 2. How to negotiate a remote work agreement with your employer: http://www.theremotetrip.com/2016/10/12/how-to-negotiate-a-r...

Hope it helps.