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I have a crazy amount of days left for PTO, over 3 weeks. I want to give my company enough time to off-board me but also want to take all of my PTO because it is use it or lose it. Can I collect a paycheck from the company I am leaving while on PTO but start my new employment with the company I am going to?

For example, last day in the office of Company A is July 31 but I am taking PTO until Aug 30 which means I will receive a paycheck on Aug 1 and Aug 15. Can I start a new job at company B on August 10 and still receive the Aug 15 check?

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    Depending on where you are in the world, overlapping employment like that has tax repercussions... its best to ask for the PTO as a lump sum at end of employment. – Moo Jul 29 '16 at 19:04
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    In the US, many (maybe even most) states require that the employer pay out earned vacation time at the end of employment. This is true even if your company has a use it or lose it policy that eliminates unused vacation days at the end of a calendar year. You don't say where you are, but you may be entitled to payment for unused vacation days. – Thomas Owens Jul 29 '16 at 19:07
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    @ThomasOwens Well I have had state employment commission tell me the exact opposite twice in that I worked for companies that went under and did not pay us the PTO. The response was unless the contract explicitly assigns a value to a PTO then the value is zero. – paparazzo Jul 29 '16 at 19:43
  • @Paparazzi It looks like about half the states have something in the laws. Massachusetts law (where I work) considers paid vacation time to be wages, and as such, vacation time must be paid out upon separation (if your company offers paid vacation time). Things like sick leave and floating holidays, however, aren't. – Thomas Owens Jul 29 '16 at 22:14
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You should look into your company's policies as this varies from one place to another.

I've seen a lot of places where you "cash out" remaining PTO days and get paid for them since it's essentially "work hours" that you have stored up and not used.

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You need to be careful. Unless the contract has a cash equivalent of PTO it has a value of zero. I worked for a company that went under and we did not get paid for our unused PTO. I filed with the state employment commission and that is the answer I got. You could turn in your notice and at the same time take vacation but you take the risk they will just terminate you. Or you could take the PTO and then on the last day resign with no notice but they might withhold you check. A lot of way this could go wrong.

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    This is true for all of the jobs I have worked at (across 3 states). Even worse, the employer could choose to not approve PTO or vacation time after putting in my two weeks. Stream even went as far as not paying me on already-approved vacation time spent after I put in my 2 weeks. Therefore unless state laws or your contract offer sufficient protection, it's better to use it prior to putting in notice. – user17163 Jul 29 '16 at 20:32
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I have never worked for a company that allowed a person to take PTO after they put in their notice. Look in your HR handbook if you have one for the policy. Also just because you can often take PTO ahead of earning it, in many companies you do not get the whole pool of days at a the beginning of the year but earn so many minutes or hours a pay period, so your earned leave balance may be considerably smaller than 3 weeks.

In some countries, you cannot work for two companies simultaneous like that, so there may be other legal implications as well.

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I work in the United States.

The employee handbook should address this, it should also tell you when all your benefits stop.

In all companies where I have worked there has been a written policy that addresses vacation or PTO when an employee leaves.

They have all fallen under two options:

  • They pay you for your hours at your normal hourly rate in a lump sum after your last paycheck.
  • They pay you in a series of 'paychecks' each of which has 80 hours of pay for for vacation/PTO.

When sick was a separate bucket they didn't pay those hours, but under the PTO plan there is no way to separate the hours. The policy should also address floating holidays and other similar plans.

In all cases once you stopped coming to the office, you were no longer an employee and were free to start work for your new company.

Note: in one case employees were given an option regarding the payout of PTO. Lump or two weeks at a time. The difference is that a bigger check has an larger initial chunk taken out for taxes, but you get it all at once. At the end of the tax year it makes no difference which method is used, but it could make a difference to some people in the short term.

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The answer to this qurstion is always going to be at LEAST company/contract specific (i.e. different for the mailboy than the CEO).

That said, in general the problem with your scenario is that your last day of work is prior to your last day of employment. If you aren't working you aren't taking time off before returning to work.

There are other factors in your being an employee than your raw salary -- insurance to name just one. It is generally not going to be in the organizations interest to have you on the books as an employee past the time when you are working.

In short, while possible, it is unlikely.

Note that extending your notice period with PTO may be acceptable -- by this I mean you give 5 weeks of notice and take 3 weeks of PTO in the middle. You working a week or a half week after your PTO may be beneficial to them. You'd have to get approval from your other job for that, which may be a harder sell.

Bottom line (and why this question may get closed): it depnds.

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