I've been remote for 4 years and it all started at a company who didn't have a remote culture, but my boss wasn't too worried about me going remote.
I was on a software team for 2 months before finding out I needed to move. I told my boss I had to move in 4 months, but I really wanted to keep my position and wanted to switch to working remotely. More than half of the engineering team at the time was offshore; however, they were all in an office with close communication with the higher-ups there. My boss basically said to me that he'd been working with remote folks for his entire career and if the other engineers had no problem with it, he didn't see an issue either.
4 years later I'm still remote and I couldn't be happier. Not at that same company, but at a new remote position.
The offshore team, previous bias to remote employees, and potentially the need to keep me onboard to get shit done for cheap helped me here. There were other employees who inquired about going remote, but they were turned down - one even needed to move for their SO (same as my case), so they ended up leaving the company when they moved.
It's really hit or miss unless you find a remote position where the company expects you to be remote right off the bat or you just get lucky and your boss trusts you to switch. Just remember that trust goes both ways - if your company doesn't trust you, maybe don't trust that you'll retire there. Going remote is a great way to test both sides of trust.
I was on a software team for 2 months before finding out I needed to move. I told my boss I had to move in 4 months, but I really wanted to keep my position and wanted to switch to working remotely. More than half of the engineering team at the time was offshore; however, they were all in an office with close communication with the higher-ups there. My boss basically said to me that he'd been working with remote folks for his entire career and if the other engineers had no problem with it, he didn't see an issue either.
4 years later I'm still remote and I couldn't be happier. Not at that same company, but at a new remote position.
The offshore team, previous bias to remote employees, and potentially the need to keep me onboard to get shit done for cheap helped me here. There were other employees who inquired about going remote, but they were turned down - one even needed to move for their SO (same as my case), so they ended up leaving the company when they moved.
It's really hit or miss unless you find a remote position where the company expects you to be remote right off the bat or you just get lucky and your boss trusts you to switch. Just remember that trust goes both ways - if your company doesn't trust you, maybe don't trust that you'll retire there. Going remote is a great way to test both sides of trust.