I'm a software engineer working for a "remote-first" company, with the condition that employees must be based within the EU. Back in May, I requested a "work-cation" in Chiang Mai, Thailand. It needed approval from my manager, and the directors. Surprisingly, it got approved within a few days without hesitation, just a "go and book your flight" Now, I’ve fallen in love with Chiang Mai, and with the new Digital Nomad Visa (DTV) announcement, I’m seriously considering a more permanent move there. However, I’m concerned that bringing this up with my boss might be pushing it too far. Has anyone had experience convincing their employer to allow full-time work from Thailand under the new visa while still being a PAYE employee? How did the process go for those who’ve done this? Was there any negotiation involved? Any advice on how to approach the conversation would be really helpful! (I was originally thinking of bringing it up casually at the next company event, maybe after a drink or two, but I’m not sure I can wait until the Christmas party — another UK winter might be too much! 😂)