It’s all over Reddit. People are working multiple full-time jobs. So I went looking for Canadians doing the same thing. They agreed to talk to me, as long as I didn’t use their real names.
“Jamie” from Vancouver: The engineer who bought a condo
Jamie works as a software engineer for a tech company in Toronto. During the pandemic, she picked up a second full-time remote job in Seattle.
“I told one company I live in Eastern time and the other that I’m in Pacific,” she said. “That gives me a three-hour window every morning to get ahead.”
Jamie wakes up at 5:30 a.m., logs into both laptops, and keeps one camera off for meetings. Her combined income is about $230,000 combined. Her main job pays $130,000, and the other adds another $100,000.
“I used the extra money for a down payment,” she said. “I’d never be able to afford a place in Vancouver otherwise.”
But she admits the stress is constant. “I dream about Slack notifications. I have two phones, two work calendars, and I pray I don’t unmute the wrong mic.”
Her bosses have no idea, and she plans to keep it that way.
A labour lawyer weighs in:
When I asked Alex Henderson, a labour and employment lawyer for MBAA Law Professional Corporation in Oshawa, Ont., whether that kind of setup is legal, he said it technically is.
“Yes, it is technically legal to work multiple jobs in Canada simultaneously,” Henderson told me. “However, an employee has a duty of loyalty and fidelity to each employer. That means they must prioritize each employer’s interests, and that can be hard to do when juggling multiple jobs.”
“Devin” from Toronto: The marketer who treats it like a game
Devin started his first marketing job in 2021 during the pandemic, working remotely for a U.S. agency. Then another recruiter reached out.
“They were offering almost the same job. Same hours, remote, good pay. I thought, why not?”
He now manages ad campaigns for both companies and earns about $190,000 total. He says it’s like “playing Tetris with deadlines.”
When asked whether it’s ethical to balance two of the same job, he says it’s the reality of today.
“The trick is to never let anyone suspect you have too much free time,” he said. “If someone asks for a meeting, I offer three time slots. I make sure one overlaps with the other job so I can multitask.”
He has two work laptops, a shared calendar on his phone, and a strict system. “If both companies have all-hands meetings, I attend one live and watch the recording of the other at night.”
Devin says his LinkedIn only lists one employer. “I’d rather look unemployed than overemployed,” he said.
It’s smart to disclose a second job, says employment lawyer
When I asked Henderson if people have to disclose a second job to their employer, he said they don’t, but it might be smart to.
“An employee doesn’t have a legal obligation to disclose a second job,” Henderson explained. “But it might be wise to do so before accepting it. That builds trust and gives the employer a chance to flag any potential conflicts before it becomes a problem.”
He added that conflicts of interest are one of the biggest risks.
“If working another job creates the possibility of a conflict with the original employer, that conflict could result in termination, possibly for cause,” Henderson said. “Employees should avoid working for multiple employers within the same industry or field.”
“Sonia” from Calgary: The analyst supporting her family
Sonia works two finance jobs. Her first is a full-time analyst position at a bank, and her second is a contract with a real estate firm.
“My husband was laid off in 2022, and we have two kids,” she said. “I didn’t have a choice.”
Her total pay is about $175,000 a year. It’s double what she used to make.
She keeps two separate home setups in her basement: One desk for the bank, and one for the contract. “If I’m in a meeting and my other job pings me, I use voice notes on my phone to remind myself what to do later.”
Her biggest fear is getting caught. “If my bank finds out, they’ll fire me. I don’t think it’s illegal, but it’s definitely against policy.”
When tax season came, she had to use an accountant. “I got slammed with income tax because both employers were deducting as if they were my only job. It’s complicated.”
When I brought this up to Henderson, he said performance and loyalty are key.
“As long as there is no conflict of interest or breach of confidentiality, an employer is unlikely to terminate an employee for having multiple jobs if their performance isn’t compromised,” he said. “That said, employers are generally free to terminate employees at any time, as long as they comply with applicable laws.”
What if you are working fewer hours than your contract?
For many contracts, you'll see a minimum number of hours or predetermined hours of duty. So is it illegal to work a second job during that time? And could you get in serious trouble for it? Henderson told me this is where overemployment becomes risky.
“Technically, working for one employer during another employer’s set working hours would be a breach of the employment contract,” he said. “Contracts set out an employer’s expectations, and one of those key expectations is working hours and availability.”
He also told me that, except for approved breaks, vacation, or leaves, you’re expected to be working when your contract says you should be working.
“If an employee is not available during an employer’s set working hours, it could lead to discipline or even termination. This is commonly known as time theft, and it has become much more prevalent with the rise of remote work.”
I asked him if this crosses into criminal territory. He said it usually doesn’t, but it’s not harmless.
“While an employer could sue an employee for time theft, it likely wouldn’t be worth the expense or time. Time theft will typically be addressed via discipline or termination if it is a persistent issue.”
What happens if you get laid off?
One of my biggest questions was about Employment Insurance (EI) and what happens if someone loses one job but still has another?
Henderson told me it depends on how much the second job pays.
“If an employee is laid off from one job but remains employed elsewhere, they may still be eligible for EI,” he explained. “However, their EI payments will be reduced as a result of the income they earn from the remaining job. If that income is high enough, they may not be eligible for EI at all.”
Why are people doing it anyway?
All three people told me the same thing: overemployment started as a way to survive inflation and layoffs. It’s not greed, but rather, safety.
Jamie said she wouldn’t quit either job unless forced. Devin said it gave him leverage to quit toxic bosses. Sonia said it saved her family.
Henderson said that reality doesn’t surprise him.
“The unfortunate reality is that many Canadians cannot live comfortably on one source of income,” he said. “Before accepting a second job, be honest with yourself. Is the income worth the impact on your personal life and health? Will you realistically be able to perform both jobs well?”
