Transitioning Jobs – Maximizing Paid Days Off

I’m switching companies for the first time in September and have some questions regarding my transition.

My current company has a policy of using all remaining paid days off before leaving. I can potentially take over a month-long vacation if I do. However, I don’t have any specific plans during that time.

1. Can I start working at the new company while still on paid days off from my current job? Any similar experiences?

2. How should I notify the Immigration Office about changing companies, especially if the starting date of my new company is earlier than my leave date from the old company?

3. Will receiving pay from two companies for a month cause any tax problems? potential implications?

I’d appreciate any guidance or personal experiences you can share.
Thanks in advance.

3 comments
  1. Depends on company rules, you should contact both companies if you’re going to start working during your PTO

  2. Neither company will like it as it creates a big hassle for them in regards to taxes and insurance (It also defeats the purpose of paid “holiday”). The new company will likely want you to be completely finished with with your previous one before you start working.

    You could ask your current company to pay out your holidays and move your resignation date up a month earlier. They may or may not go for it. If not, take a holiday.

  3. Even if you take PTO, you are still on paper employed by your old company. Once your PTO is done, then you are free to go. Otherwise you’ll be working at two companies at the same time, and tax office ain’t gonna like it.

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