8 answers
Angy
Student
Milan, Lombardy, Italy
23
Questions
Asked
2008 views
How to communicate important plans for your life to your manager?
Hi I got this offer from this great company with great pay and really good quota for a SDR role, I will be opening a Italian LLC to work with them. Now the job is fully remote and me being in Italy I wanted to move abroad to study physics and acting. The thing is that during the hiring process I didn’t tell them the fact that I was going to move abroad. After I’ve signed the contract I told my manager that I wanted to move abroad and do acting and he was perfectly fine with it(I didn’t tell him tho that I wanted to go to college). But now while talking with the accountant and communicating this they said there could be some issues with that because of tax regulations, but the guy who interviewed me(the CEO) said that he didn’t know that I wanted to move abroad and that he didn’t know that and he seemed pretty annoyed that I didn’t communicate it sooner(I actually thought I did in my first interview). Now I don’t know how to tell him that I want to move to LA to do acting and physics, and I need the job to pay for my studies. I’ll have to start in September and I’ll do one month of just working. I also have to tell this to my parents and everything is pretty stressful on its own. How do I tell him? Do I tell him that I won a scholarship for this school and If it’s okay for him that I go. He said he didn’t have problems with people going all around the world as long as they could do the job right. Please I am drowning
Login to comment
8 answers
Albina Temisheva
Career Strategist dtmymonday.com
7
Answers
Florence, Tuscany, Italy
Updated
Albina’s Answer
Hi Angy.
As an entrepreneur who works in the Italian market, I can tell you that CEOs understand business realities better than it seems. His annoyance is probably more about being surprised than actually disagreeing with your plan.
Here's what I would do in your situation, and this will definitely help because this is how things actually work in real life. Honesty works for you and your reputation and gives you tons of opportunities in the future. Be honest with everyone always - with yourself, with your parents, and with employers, and especially with Italian tax authorities (these guys don't mess around!).
I would immediately do several things:
1. Communication strategy with CEO (with examples of what I would focus on):
Ask for a meeting immediately - don't put this off, it's super important
Start by admitting the mistake: "I realize I should have been clearer about my plans from the beginning, and I apologize for any confusion"
Present this as an opportunity: "I've been accepted to study physics and acting in LA, which will actually enhance my creativity and problem-solving skills for the SDR role"
Emphasize your commitment: "This opportunity is exactly why I need this job - to fund my education while delivering excellent results for the company"
Offer a trial period: "I'm willing to prove during the first month that location won't affect my performance"
2. Tax issues - critically important:
According to Italian law, your situation creates several risks:
If you spend more than 183 days in the US, you stop being an Italian tax resident. This means completely different tax rules for you as an LLC owner, and for the company you plan to work for through your LLC
The company may face additional tax obligations
There could be double taxation problems
Immediate actions:
Find a tax consultant who specializes in international law
Look into Digital Nomad visa options or other special tax regimes. Italy offers special programs for remote workers and digital nomads (Digital Nomad visa, Regime impatriati) that can reduce your tax burden, but they require meeting certain conditions (like proving income, living in Italy for a certain time)
Prepare a clear tax planning proposal to present to your employer
3. Talk with your parents:
Present this as an investment in the future, not as a "dream"
Show them a financial plan: income from work will cover study expenses
Emphasize that this is temporary and strategically planned
4. Managing employer expectations:
Offer regular check-ins to monitor performance
Ensure overlap with Italian working hours
Be ready for compromises (like periodic visits to Italy)
What I would say to the CEO:
"I want to be completely transparent with you about my situation. I've been accepted to study in LA, and I understand this creates both opportunities and challenges. I'm committed to making this work for the company and am willing to invest in proper tax consultation to ensure full compliance. Can we discuss how to structure this to benefit both sides?"
Remember: honesty and professionalism in solving problems often make a better impression than having a "perfect" situation from the start.
Good luck!
As an entrepreneur who works in the Italian market, I can tell you that CEOs understand business realities better than it seems. His annoyance is probably more about being surprised than actually disagreeing with your plan.
Here's what I would do in your situation, and this will definitely help because this is how things actually work in real life. Honesty works for you and your reputation and gives you tons of opportunities in the future. Be honest with everyone always - with yourself, with your parents, and with employers, and especially with Italian tax authorities (these guys don't mess around!).
I would immediately do several things:
1. Communication strategy with CEO (with examples of what I would focus on):
Ask for a meeting immediately - don't put this off, it's super important
Start by admitting the mistake: "I realize I should have been clearer about my plans from the beginning, and I apologize for any confusion"
Present this as an opportunity: "I've been accepted to study physics and acting in LA, which will actually enhance my creativity and problem-solving skills for the SDR role"
Emphasize your commitment: "This opportunity is exactly why I need this job - to fund my education while delivering excellent results for the company"
Offer a trial period: "I'm willing to prove during the first month that location won't affect my performance"
2. Tax issues - critically important:
According to Italian law, your situation creates several risks:
If you spend more than 183 days in the US, you stop being an Italian tax resident. This means completely different tax rules for you as an LLC owner, and for the company you plan to work for through your LLC
The company may face additional tax obligations
There could be double taxation problems
Immediate actions:
Find a tax consultant who specializes in international law
Look into Digital Nomad visa options or other special tax regimes. Italy offers special programs for remote workers and digital nomads (Digital Nomad visa, Regime impatriati) that can reduce your tax burden, but they require meeting certain conditions (like proving income, living in Italy for a certain time)
Prepare a clear tax planning proposal to present to your employer
3. Talk with your parents:
Present this as an investment in the future, not as a "dream"
Show them a financial plan: income from work will cover study expenses
Emphasize that this is temporary and strategically planned
4. Managing employer expectations:
Offer regular check-ins to monitor performance
Ensure overlap with Italian working hours
Be ready for compromises (like periodic visits to Italy)
What I would say to the CEO:
"I want to be completely transparent with you about my situation. I've been accepted to study in LA, and I understand this creates both opportunities and challenges. I'm committed to making this work for the company and am willing to invest in proper tax consultation to ensure full compliance. Can we discuss how to structure this to benefit both sides?"
Remember: honesty and professionalism in solving problems often make a better impression than having a "perfect" situation from the start.
Good luck!
Josafat Ruiz
Management
3
Answers
Heredia, Heredia Province, Costa Rica
Updated
Josafat’s Answer
Hi Angy, transparence and honesty are always the best way to go - you have a great opportunity and although the moving to LA upset the CEO, he seems to be OK with it as long as you perform to expectation and deliver results. Balance your priorities and see what you need against what you want, work and study first - then, invest time in personal goals when you are steady with your responsibilities. If you are close to your family, share with them - seek for advice and support, most times communicating/sharing goes a long way and helps a lot with though decisiones and situations. Figure out the tax situation and dont hide your true goals with the scholarship, hope this helps. Best of luck and success.
Vanessa Herrera
Provider Relations
3
Answers
Long Beach, California
Updated
Vanessa’s Answer
Hi Angy,
I think it's best to continue being honest and transparent about your future plans. Just like in all job interviews and onboarding processes, employers take a chance on new hires and need to assess the employee's ability to deliver/demonstrate quality work; there's usually a probation period. If you can perform your job duties from a different country, accommodate business needs e.g., business hours, and you accept the pay/tax regulations, the employer should uphold their initial response to you. Hope it all works out!
I think it's best to continue being honest and transparent about your future plans. Just like in all job interviews and onboarding processes, employers take a chance on new hires and need to assess the employee's ability to deliver/demonstrate quality work; there's usually a probation period. If you can perform your job duties from a different country, accommodate business needs e.g., business hours, and you accept the pay/tax regulations, the employer should uphold their initial response to you. Hope it all works out!
Roxangely Cortes
Global Operating Engineering Manager
1
Answer
Aguadilla Pueblo, Puerto Rico
Updated
Roxangely’s Answer
Hi Angy!
My suggestion would be to talk things through with both your manager, CEO and parents. I believe you'll feel much better after doing so. It looks like you have a plan so just share it with them. Regarding the job, explain to you CEO and manager that you will be able to do the job remotely. Remember to bring out all those qualities that got your selected for the position and let them know you are confident in your ability to execute the tasks you agreed on when accepting the offer. Ask them to please work with you to figure out a way to incorporate your move into the agreement. As for your parents, let them know about the great job opportunity you earned and explain why going to school is so important for you and what are your plans long term after obtaining the degree. Mention how you'll be able to pay for school with your job. Acknowledge it will be a big move a responsibility but that you are looking forward to it and will be putting in your best effort to make it happen. I bet your parents will be proud of you.
My suggestion would be to talk things through with both your manager, CEO and parents. I believe you'll feel much better after doing so. It looks like you have a plan so just share it with them. Regarding the job, explain to you CEO and manager that you will be able to do the job remotely. Remember to bring out all those qualities that got your selected for the position and let them know you are confident in your ability to execute the tasks you agreed on when accepting the offer. Ask them to please work with you to figure out a way to incorporate your move into the agreement. As for your parents, let them know about the great job opportunity you earned and explain why going to school is so important for you and what are your plans long term after obtaining the degree. Mention how you'll be able to pay for school with your job. Acknowledge it will be a big move a responsibility but that you are looking forward to it and will be putting in your best effort to make it happen. I bet your parents will be proud of you.
James Constantine Frangos
SOFTWARE ENGINEER SINCE 1972; NUTRITIONIST SINCE 1976.
7094
Answers
Gold Coast, Queensland, Australia
Updated
James Constantine’s Answer
Hello Angy,
You're a valued employee, and the company really wants to keep you. There's concern about you leaving, so much so that the CEO forgot what you had said! It is important to meet with the CEO to discuss your plans. You might consider working remotely and helping with the Sales Development Representative role from afar. The company will likely need a manager in Italy, and you could guide the team there as a consultant through online meetings from LA. You can stay involved with regular Skype or Zoom calls while you continue your studies. You will benefit from meeting with your parents to discuss your future. Balancing work and study will require good nutrition, and I'm here to help if you need advice.
You're a valued employee, and the company really wants to keep you. There's concern about you leaving, so much so that the CEO forgot what you had said! It is important to meet with the CEO to discuss your plans. You might consider working remotely and helping with the Sales Development Representative role from afar. The company will likely need a manager in Italy, and you could guide the team there as a consultant through online meetings from LA. You can stay involved with regular Skype or Zoom calls while you continue your studies. You will benefit from meeting with your parents to discuss your future. Balancing work and study will require good nutrition, and I'm here to help if you need advice.
Suzi Leão
1
Answer
São Paulo, Brazil
Updated
Suzi’s Answer
Hi, Andy!
In my opinion do you have to be sincere and honest.
Tell the CIO that you won a scholarship at a school in another place, but this will not be a problem; in reality, it will be good for your professional life, and you appreciate that they consider your efforts to begin a professional life with stability.
We will not know the reaction of other people, but you will know that you are doing the right thing!
In my opinion do you have to be sincere and honest.
Tell the CIO that you won a scholarship at a school in another place, but this will not be a problem; in reality, it will be good for your professional life, and you appreciate that they consider your efforts to begin a professional life with stability.
We will not know the reaction of other people, but you will know that you are doing the right thing!
Daniela Salas
Operation Manager
3
Answers
San José, Costa Rica
Updated
Daniela’s Answer
Hello Angy,
My suggestion is to communicate openly and authentically. Be clear about your intentions and share a well-thought-out action plan to show how your work performance won’t be affected by relocating to another country. Companies value transparency and a solid plan that demonstrates your commitment to maintaining the same level of quality from abroad.
The same goes for your parents — showing them that you have a clear life plan and direction will help ease their concerns and build their trust in your decision. Good luck!
My suggestion is to communicate openly and authentically. Be clear about your intentions and share a well-thought-out action plan to show how your work performance won’t be affected by relocating to another country. Companies value transparency and a solid plan that demonstrates your commitment to maintaining the same level of quality from abroad.
The same goes for your parents — showing them that you have a clear life plan and direction will help ease their concerns and build their trust in your decision. Good luck!
Aravind C
39
Answers
Bengaluru, Karnataka, India
Updated
Aravind’s Answer
Hi Angy,
Be clear about your plans: Clearly explain what you want to share, why it’s important, and how it might impact your work.
Pick the right time: Choose a moment when your manager isn't too busy or distracted. It's best to set up a private meeting.
Be ready for questions: Think about how your manager might react and prepare answers, especially about timelines, changes, and your dedication.
Communicate honestly: Be straightforward and sincere so your manager can easily understand and accept what you're saying.
Be clear about your plans: Clearly explain what you want to share, why it’s important, and how it might impact your work.
Pick the right time: Choose a moment when your manager isn't too busy or distracted. It's best to set up a private meeting.
Be ready for questions: Think about how your manager might react and prepare answers, especially about timelines, changes, and your dedication.
Communicate honestly: Be straightforward and sincere so your manager can easily understand and accept what you're saying.