On SG pay? That is nice. Congrats to your early retirement
I am not sure if it will be allowed. Our company has very strict rules about international remote (max 1 month a year) and for someone who has made up his mind to leave the company, I dont think they will make any exception.
My company doesnt have any presence in India. However, they have outsourced to IT partners, but even those IT partners are in different city from where I am going.
Basically, while resigning I am going to tell my boss, my plan is not to quit for a better salary or a better role in another company; like most people resign, like 90% people resign inorder to jump to another company.
It is very rare that people would resign to retire early. So I am going to tell him, if he can offer me some options to work from home from India, I might consider taking it up. Although, it is unheard of, of anyone getting this option.
Infact, there is a Malaysian working in our company and he travels daily in and out from JB. All of us, work in office only 3 days a week, but this Malaysian has to come to office 5 days a week, because international remote is not allowed.
So, I dont think they will make any exception in my case, my base case is I resign and go, but I will put the ball in the court of my boss to see if I can get any options.
Actually, it is not that my role is very critical, but the stuff that I do, I really take care of lot of things and my boss doesnt have to worry about them. But if I leave, he will have to find a replacement, who may not be as keen in taking the same level of ownership that I do.
But then we never know, we all overestimate our worth in the team. We think if we leave, the team will scramble and will have a hard time. But that rarely happens, I have seen so many much more important and established people leave and my company didnt give a damn, they were all told by our department head "I am happy for you". So I dont expect anything different.