About 10 years ago, I met for the first time someone who was working remotely. I hate commuting (As an employee, I have always lived close to my office) and at that point, I had decided this was what I wanted. It took me about 3 years to get to that point. Here is how it worked for me:

- Start freelancing. I started by negotiating with my employer to transform a full-time job into a part-time one. This is a great way to start.

- Accept what you find until you can get 100% freelance, but have a preference for remote work. Be ready to cut your rates to work remotely.

- Grow your network and reputation until you can have 100% of remote work at a decent rate.

Now we moved to a countryside we like with my wife, we have a house for half the price of an apartment in the city we used to live. I now say upfront to clients that I can only work remotely. I occasionally go to meetings in Tokyo (which is a bit less than 2h away from where I live) but Skype works most of the time.

Be available. Be reactive. Be ready to make mistakes that will cost you time and stress. Be ready to have some shitty clients that will bitch and won't pay. It takes a few years before you get to a level where the stress is lower than an employee job but it is worth it IMHO.