The Secret Side Hustle: How Working Two Full-Time Jobs Can Unlock Financial Freedom

In today’s hyper-connected world, the 9-to-5 job is no longer the only path to success—or survival. A growing number of professionals are taking on multiple full-time remote jobs simultaneously, a trend known as being overemployed. What started as a niche strategy whispered about on Reddit forums has exploded into a larger cultural and economic phenomenon.

The driving force? Financial freedom.

What Does It Mean To Be Overemployed?

Being overemployed doesn’t necessarily mean working 80-hour weeks in a nonstop hustle. In many cases, it's about leveraging the flexibility of remote work to discreetly juggle two (or more) full-time salaried positions.

These professionals attend meetings, hit deliverables, and meet expectations—often without either employer knowing they're not the only one.

While the ethics and legalities are still being debated, the overemployed workforce is expanding—and the reasons are becoming clearer every year.

Why Professionals Are Choosing the Overemployed Life

1. Economic Instability and Stagnant Wages

For many, one income simply isn't enough. In Canada, over 1.1 million people—or 5.6% of the workforce—held more than one job in 2023, a slight increase over previous years. And while the cost of living climbs, wage growth hasn’t kept pace.

Among those holding multiple jobs, nearly 41% worked more than 50 hours per week, according to Statistics Canada. These aren’t just side hustles—they’re real efforts to close the growing gap between earnings and expenses.

2. Remote Work Made It Possible

The rise of remote work, catalyzed by the pandemic, eliminated the physical boundaries that once made working multiple jobs impractical. Now, thanks to flexible hours, asynchronous communication, and Zoom meetings, many Canadians are finding it feasible to balance two full-time jobs from their living rooms.

Online communities like Reddit’s r/Overemployed have Canadian professionals openly discussing how they manage dual roles—often without breaking a sweat.

3. Living Paycheck to Paycheck Is the Norm

A recent ADP study found that 56% of Canadians live paycheck to paycheck, with more than half of multiple jobholders still struggling financially. For those juggling three or more jobs, 61% say they still find it difficult to get ahead.

When asked why they hold multiple jobs:

• 34.9% said it was financial necessity

• 34.8% aimed to boost income

• Only 14.5% were doing it for personal interest or passion

  
  

This paints a clear picture: for most, overemployment isn’t about ambition—it’s about survival.

4. A Fast-Track to Financial Goals

For some, however, overemployment is a short-term strategy to reach long-term goals. Whether it's saving for a down payment, paying off student loans, or building a retirement cushion, many Canadians see working multiple jobs as a way to escape the rat race faster.

And with many reporting that they feel less burned out than they did in traditional roles—thanks to setting their own pace—overemployment is starting to look more like a calculated move than a desperate one.

Is It Ethical? Legal? Sustainable?

That depends. Some Canadian employment contracts include exclusivity clauses, while others are more relaxed. Ethically, critics argue it’s deceptive. But proponents counter that employers have long abandoned loyalty when convenient—mass layoffs, stagnant wages, and vanishing pensions are all proof of that.

Legally, unless you're breaching a contract or underperforming, holding multiple jobs is often in a gray area—particularly if you’re transparent about your availability and performance.

A Quiet Revolution in Canadian Work Culture

The rise of overemployment in Canada reveals deeper cracks in the traditional employment model. With inflation outpacing wages, housing costs soaring, and financial pressure mounting, professionals are no longer relying on a single employer to meet their needs.

Instead, they're hacking the system: building multiple income streams, reclaiming autonomy, and rewriting the rules of modern work.

Final Thought:

The overemployed aren’t lazy or dishonest—they’re strategic. They're creating a buffer against economic uncertainty, taking control of their finances, and exploring new ways to live and work. But like any strategy, it comes with risks—and rewards.

Would you consider working multiple full-time jobs if it meant reaching financial freedom sooner? Or does it feel like a dangerous game?