How to Money · Wednesday, September 9, 2026
According to Rochelle Gamlam, many US companies deny requests for employees to work remotely from other countries, primarily due to tax, healthcare, and time zone concerns. To circumvent this, she suggests asking for a switch to a 1099 contractor status, which shifts tax and healthcare responsibilities to the individual.
“That is a great question. I would say people are doing all sorts of different things. And what I have seen is this challenge where people with fully remote jobs ask their job if I can you know if we could take that abroad, And I have strategies for how to get this conversation going, which we can talk about today, But typically the answer is no, they don't want you to take it outside the US, mainly for tax reasons, healthcare reasons, and time zone reasons, sometimes also security reasons.”
“And so one thing that we can do is ask them to switch you to a ten ninety nine contractor like if you're from the US, so that then they are not responsible for the taxes of the healthcare. You handle that, which is fine because you're moving to a country where that's going to be a little bit easier and more affordable for you. And so that's one route that we do.”