Canadian expat tax guide: “If I work abroad, where do I pay taxes?”—and other questions answered

And don’t forget: Canadian healthcare coverage eventually expires for expats. According to the CRA, your provincial health plan might cover some of your medical expenses outside the country should you get injured or sick, but you’ll have to pay those fees up front. And after six to eight months, your coverage becomes invalid. 

“I’m always talking to people about health insurance, disability insurance and life insurance. In Canada, disability insurance is often a part of your employment package but that’s not the case for many people working overseas, so build those into your budget,” suggests Hiscock. “Find a broker that can assist with expat insurance.”

Set up an emergency fund to cover three to six months of expenses. This is advisable for everybody, including residents of Canada, but even more so for expats, who face higher risks. “And if you don’t have a job, then set aside a significant emergency fund, depending upon your situation,” suggests Hiscock. 

Talk to other expats

The more information and lessons learned you collect from other expats, the better off you’ll be, says Judith Asher, a Montreal-born executive and leadership coach who moved to Italy 20 years ago with her Danish-born husband. The language barrier and not understanding how Italy’s taxation system worked when setting up her own consulting company proved challenging.  

“When I first moved to Italy, there was much less information and advice available online from other expats about sorting out financial issues—Italy is notorious for its bureaucratic and often-changing financial rules,” she recalls. 

“Until my Italian language abilities improved, I was unable to understand official government websites on my own and had to rely on others to explain the rules to me, which left me feeling frustrated and disempowered.” 

Asher also wrongly assumed that when speaking with local accountants, she would be given options and financial advice that was in her best interest. 

“I wish I’d known to ask probing questions like: ‘What else might I do to lower my tax burden?’, ‘What other deductions could I claim that we have not spoken about?’, ‘How might opening a company be more/less beneficial than being a freelance professional in terms of taxation and bureaucratic burden?’, ‘After I make these payments, what other payments will need to be made and when?’ and ‘What kind of documentation do I need to keep in order to claim deductions?’,” she says.