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Kindly recommend some self help books!
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Just keep in mind that working remotely from locations other than your home state can have tax implications for both you and the company you work for.
I've never really thought about timeline, I've always just done it when it feels right. I think a month is probably sufficient. Once you get a good feeling for how the company operates, you should be free to travel without issue.
As long as you maintain a professional presence, there's no timeline.
I'd personally not want my first day to be while I'm traveling because it's more difficult to control variables (like hotel fire alarms during an important call), but beyond that, I don't even tell people when I'm traveling.
Just do good work and maintain a professional presence. You'll be fine.
If you need to be online during work hours, make sure you pick a location with great wifi. Hotel wifi is unreliable unless they offer upgraded options.
Also, did you provide your employer with your ip address? If so, they know your location.
I’ve only done one work vacation. It was after maybe two years in the role?