Supporting Employees with Multiple Jobs: What HR Leaders Need to Know

More Canadian workers than ever are holding down two—or even three—jobs. Some do it to keep up with living costs, while others find it an effective strategy for building financial security. Whatever the motivation, this trend is reshaping the employer-employee relationship, and HR leaders can’t afford to overlook it.

This article explores why more Canadians are working multiple jobs, the personal and organizational risks involved, and how HR leaders can respond with empathy, strategy, and support.

Moonlighting—once used to describe traditional evening or weekend work—has evolved. Today, it encompasses a broad range of secondary work: freelance projects, gig economy platforms, online businesses, and creative side ventures. The core idea stays the same, though: holding a second (or third) paid role alongside a primary job.

For employers, moonlighting raises critical questions:

• Can employees maintain performance while juggling multiple responsibilities?
  
• What risks does dual employment pose for burnout and well-being?
  
• When do side jobs create conflicts of interest—or opportunities?
  
• Should organizations have formal policies on outside employment?

These questions aren’t just theoretical. With more workers seeking supplemental income or personal fulfillment through second jobs, HR professionals must determine how best to support their workforce, without compromising productivity or culture.

Rising living costs, long-term financial goals, and greater access to gig work are key reasons that more Canadians are taking on second jobs—blending necessity with opportunity and ambition. Let’s examine in more detail the reasons that Canadian workers take multiple jobs.

According to ADP Canada’s 2025 “People at Work” survey, nearly half of Canadian workers holding two jobs say they’re doing so to cover essential or extra expenses. Economic insecurity, rising housing costs, and stagnant wages are pushing employees to supplement their income in any way they can.

This isn’t a fringe issue. Holding multiple jobs has become a pragmatic response to the financial realities many workers face. It also reflects a growing need for economic resilience, particularly among younger professionals navigating student loans, inflated rent prices, and long-term cost-of-living increases.

Interestingly, the motivation isn’t always immediate financial survival. The same ADP survey found that 58% of Canadians with three jobs say they’re working to build their savings or prepare for retirement. For this group, holding multiple jobs is a long-term financial strategy.

This finding is particularly important for employers focused on employee retention. Workers who are unable to meet savings goals through their main job may eventually seek full-time opportunities elsewhere that offer better compensation or financial benefits.

Side gigs are more accessible than ever. When remote workers with enough flexibility access platforms like Uber, DoorDash, Upwork, and Etsy, they can pursue a much-needed extra income outside traditional work hours. Other individuals see those apps as opportunities to monetize their skills or passions as a first step toward entrepreneurship.

From an HR perspective, this shift offers both challenges and opportunities. While gig work can increase burnout risk, it can also help employees to build transferable skills that benefit the organization, if appropriately supported.

Holding two or more jobs might solve financial problems, but it often comes at a personal cost. The pressure of managing multiple roles can lead to chronic stress, fatigue, and emotional strain. For many Canadian workers, burnout is no longer an abstract risk—it’s their day-to-day reality.

Burnout is especially pronounced among workers juggling full-time jobs, caregiving duties, and additional employment. This “double burden” is most commonly experienced by women, who are more likely to balance paid work with unpaid responsibilities at home, such as raising a family.

When burnout escalates, it can lead to:

• Decreased job performance
  
• Higher absenteeism and turnover
  
• Mental and physical health challenges
  
• Erosion of workplace culture and morale
  

HR leaders must be proactive and prepared to address those challenges with strategies that support employee well-being.

The generational shift in burnout trends is hard to ignore. Where previous generations often experienced burnout mid-career, younger professionals are now reaching that point much earlier. Data shows that Millennials and Gen Z workers are experiencing significantly higher levels of stress, exhaustion, and disengagement than their older peers.

For HR leaders, this generational difference is critical. Younger employees are not only burning out faster, they’re also more likely to make drastic career changes as a result. Without targeted support, organizations risk losing emerging talent to burnout, disengagement, or more flexible job opportunities elsewhere.

Multiple jobholding isn’t going away, and ignoring it won’t make it less relevant. A more productive approach is for HR leaders to recognize the broader context around moonlighting and find ways to adjust workplace practices accordingly. Here are five key strategies to consider:

Flexible schedules and remote work arrangements help employees to manage their time more effectively—particularly those balancing multiple jobs. However, flexibility must be paired with clear expectations. HR teams should work with managers to set performance benchmarks that allow for autonomy while maintaining accountability.

At the same time, trust is critical. When employees hide their side jobs to avoid consequences, it can be a severe blow to workplace culture. A transparent and flexible policy helps to normalize honest conversations and set appropriate boundaries.

As we’ve seen, working two jobs can significantly strain mental health. Consider offering Employee Assistance Programs (EAPs), mental health benefits, and wellness tools that can help employees manage stress. Today’s workforce increasingly values on-demand services, virtual therapy options, and burnout workshops.

Even simple steps—like promoting no-meeting days or encouraging use of vacation time—can help reduce overwork and support better work-life integration.

A formal policy on outside employment can prevent misunderstandings and reduce potential conflicts of interest. Your HR team must work with legal counsel to define what types of external work are permitted, what must be disclosed, and how these activities should be reported.

Policies should focus on transparency and mutual benefit, not surveillance. When handled openly, many side jobs can actually complement an employee’s growth and value to the company.

If employees pursue second jobs to grow skills they aren’t using in their primary role, it signals an opportunity for internal development. Help employees to grow within your organization, so they’ll be less likely to look elsewhere, either for extra income or professional fulfillment.

Consider investing in:

• Skills-based learning programs
  
• Stretch projects or internal gigs
  
• Mentorship and coaching
  
• Cross-functional mobility pathways

Dual jobholding is, in most cases, a reflection of economic necessity or ambition. So, you shouldn’t see it as a failure of loyalty. When employers respond with empathy instead of judgment, they open the door to better retention, employee engagement, and morale.

As an HR leader, it’s your role to foster a culture that encourages open dialogue, respects employee autonomy, and values financial wellness. This culture can support a resilient, future-ready workforce.

Multiple jobholding is now a permanent feature of Canada’s labour landscape, driven by financial need, evolving career goals, and expanded gig opportunities. With 1.1 million Canadians holding more than one job, HR leaders must adapt. Younger and female workers face higher burnout risks, while others seek flexibility and income security.

When employers support work-life balance, mental health, and skill development, they’ll strengthen retention and engagement. Don’t think this shift is about lowering expectations, though—it’s about meeting today’s workforce where they are. Forward-thinking organizations will turn this reality into a strategic advantage by fostering trust, transparency, and resilience.

Also, consider adopting outplacement services in your organization to add an extra layer of trust. Companies that offer outplacement see higher engagement and talent retention and an improvement in brand reputation. Contact our experts at Careerminds and learn more about our modern, result-driven approach to outplacement.