Digital Nomad as a tax strategy

Has anyone here actually found a company or organization that is okay with letting you work from anywhere?

Either as a organization or an individual?

I tried it with my company, whom I’ll probably be leaving once I find a new gig. I work full remote, asked to do a shift for cost of living purposes either as an employee or contractor and was flat out denied. That was also the same day that I ordered my mouse mover

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u/ConsequenceFew6931 — 14 days ago

Company won’t accommodate nomad status

HR at a small company (a few hundred ish) I have been working for quite a while, even though I believe my role was one of extreme value, stated they wouldn’t be able to accommodate me working as a nomad or a change to my employment structure.

Not sure if I should raise an argument to the CEO/CFO, but I would be bypassing HR.

Feel like at this point it would be better to just get a job that pays more even though if it means I’d only be able to travel on vacation.

Should I side step HR and go talk to the CEO?
Or look for a company which would let me work the nomad lifestyle

HR basically already said they wouldn’t offer contracting jobs or accommodate employees in other countries

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u/ConsequenceFew6931 — 28 days ago
▲ 371 r/FleeingCanada+1 crossposts

Is anyone planning to leave Canada?

Genuine question and it’s been discussed a lot in my circles nowadays.

Seems like affordability is on the top of young people’s mind, and no one in charge seems to be thinking of them even though “Affordability is the best it’s ever been in 10 years”

What do you guys think? Is there a future in Canada?

Is anyone making a plan to leave?

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u/ConsequenceFew6931 — 1 month ago

Any remote workers thinking of leaving Canada?

Thinking of leaving Canada for a country with a cheaper cost of living, a better future and the tax savings.

Wondering if anyone is also in the same boat or has already made the move?

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u/ConsequenceFew6931 — 1 month ago

Anyone else fed up with how much in taxes we pay and what little we get out of it?

How many of us are living on the brink paying a rent or mortgage like a slave while we get taxed for everything we do?

When will things change?

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u/ConsequenceFew6931 — 2 months ago

Hey everyone.

I’ve been with my current company for about six years. It’s a small company where everyone knows everyone, so there’s some leeway to adjust my employment agreement
but I don’t want to push things or create unnecessary complexity for my employer.

I’m considering moving out of Canada to a country that doesn’t tax foreign-sourced income. Panama is my first thought because of its territorial tax system, weather, and cost of living.

The issue: my employer isn’t set up to handle a permanently overseas employee from a payroll, tax, and compliance standpoint.

My thought is that switching my status from employee to independent contractor would significantly reduce that burden on them.

I’m aware the CRA has its own tests for employee vs. contractor classification, but my understanding is those concerns largely fall away once I’m a non-resident for Canadian tax purposes — since there’s no Canadian source income, no CPP/EI owing, and nothing for CRA to claw back.

Would this arrangement actually be feasible? Anyone who’s done something similar - what am I missing?

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u/ConsequenceFew6931 — 2 months ago
▲ 0 r/cantax

Apologies in advance if this isn’t the right sub.

I’ve been with my current company for about six years. It’s a small company where everyone knows everyone, so there’s some leeway to adjust my employment agreement
but I don’t want to push things or create unnecessary complexity for my employer.

I’m considering moving out of Canada to a country that doesn’t tax foreign-sourced income. Panama is my first thought because of its territorial tax system.

The issue: my employer isn’t set up to handle a permanently overseas employee from a payroll, tax, and compliance standpoint.

My thought is that switching my status from employee to independent contractor would significantly reduce that burden on them.

I’m aware the CRA has its own tests for employee vs. contractor classification, but my understanding is those concerns largely fall away once I’m a non-resident for Canadian tax purposes — since there’s no Canadian source income, no CPP/EI owing, and nothing for CRA to claw back.

Would this arrangement actually be feasible? Anyone who’s done something similar — what am I missing?

reddit.com
u/ConsequenceFew6931 — 2 months ago

I work remote full time and have been doing so for almost 5 years. My company is small around 150ish people.

They said working from abroad is something they’re not equipped to do because of how complex it is from a tax compliance and payroll standpoint.

Anyone know what I could say to that? I was going to bring up working as a contractor but then again I wasn’t sure if that would just sound naive.

Many companies do let employees work remote (think off sourcing, company’s that ship jobs overseas).

Anyone advice is appreciated

Edit: Title should have been convincing company to let me relocate to a foreign country

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u/ConsequenceFew6931 — 2 months ago