I've been a US-based remote worker for close to 3 years now.
I started doing contracting work in Rails while I worked full time in .NET (while going onsite everyday). I also networked a lot within the local Ruby community. When I was ready to jump to Rails full time, a friend through the community was staffing up an early stage startup with remote devs spread across the city. This was a good way to dip my toes into remote work while still maintaining local connections.
After a year of that, I jumped to a larger company to join their remote team of Rails developers (currently about 10 of us are remote). Now I'm pretty adjusted to the remote lifestyle and it would be very hard to let go of it since the impact to family life is so positive.
My advice would be to do as many others have done and start with remote contracting to see how it works. Then you can either convert to full time or find another full time role later if you need benefits. However, if you can remain as a contractor I would generally advise people to do that if your financial situation allows for it.
I started doing contracting work in Rails while I worked full time in .NET (while going onsite everyday). I also networked a lot within the local Ruby community. When I was ready to jump to Rails full time, a friend through the community was staffing up an early stage startup with remote devs spread across the city. This was a good way to dip my toes into remote work while still maintaining local connections.
After a year of that, I jumped to a larger company to join their remote team of Rails developers (currently about 10 of us are remote). Now I'm pretty adjusted to the remote lifestyle and it would be very hard to let go of it since the impact to family life is so positive.
My advice would be to do as many others have done and start with remote contracting to see how it works. Then you can either convert to full time or find another full time role later if you need benefits. However, if you can remain as a contractor I would generally advise people to do that if your financial situation allows for it.