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PdS per lavoro subordinato to Autonomo

Hi other expats in Italy!

My name is Yurie, and I live in Puglia.
I am currently working in a company with tempo indeterminato for almost 2 years but I would like to leave before December 2017 and take long holiday+prepare for next. My permesso di soggiorno lasts till February 2018, and I am planning with my commercialista to ask for laboro autonomo as libero professionista. This part is simple and questura said it shouldn't be a problem to process it.

Since I need to go to other countries for next steps+holiday in December, I believe it's better not to move from Subordinato to Autonomo yet. Because I'm not going to my home country and I prefer not to travel with just a ricevuta of next PdS.
I am planning to request it in January but obviously I will prepare all the documents and register P.IVA/CCIAA before January. 

So here is my question: does anyone know if this can be a problem? Leaving subordinato job then a month later to ask for next PdS? I know it's a silly question and I'm pretty sure this doesn't make any problem if there is a permesso di soggiorno but I would like to know if anyone encountered same situation before or experienced before!

Grazie!
Yurie

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