I work for an all remote US based company of around 50 people. Our small company is under a larger holding company.

I just got back from abroad where I traveled and worked for four months. A week after I was back I got an email from our CEO asking for my return date (thought I was still abroad) as “anything longer than 180 days would cause legal and business issues and would acquire special approval”.

I want to travel again in the new year and am wondering if I should ask for permission again or just tell them where I’m headed. Worried “asking” if I can do it will give them opportunity to refuse.

I’m probably just overthinking the email I received…