It’s official: the "side gig" has moved from a hobbyist’s passion project to a professional staple. According to recent data from Careerminds, over two-thirds of American adults now have a side hustle.
But here’s the reality check for leaders: for most of your team, this isn't about "finding themselves"—it’s about financial survival. With 64% of side hustlers citing job security concerns as their primary motivator, managers can no longer afford to ignore the elephant in the room.
If you want to keep your top talent engaged and productive, you need to stop viewing side hustles as a distraction and start seeing them as an opportunity. Here are five strategies to help you navigate the side hustle era.
1. Lead With Curiosity, Not Judgment
The moment a manager discovers an employee has a second job, the "knee-jerk" reaction is often fear: Are they distracted? Are they quitting? This reaction kills trust. Instead, approach the discovery with genuine curiosity. Understanding the "why" behind the hustle helps you support the human behind the desk.
The Benefit: An employee freelancing in graphic design or running an Etsy shop is building skills—like digital marketing or customer service—that can actually benefit your organization.
Expert Tip: In your next one-on-one, try asking: "What motivated you to start this project, and what are you hoping to gain from the experience?" ### 2. Set Boundaries (Without the Micromanagement)
With some employees clocking up to 20 extra hours a week outside of their 9-to-5, burnout is a real risk. Clear boundaries protect both the company and the employee’s mental health.
The Non-Negotiables: Side projects shouldn't happen during work hours, shouldn't use company equipment, and must not compromise the quality of their primary role.
Expert Tip: Focus on results, not activities. Instead of asking if they’re working on their project during the day, ask: "How are you managing everything on your plate right now?" This invites an honest dialogue about workload.
3. Address Conflicts Early
Not every side hustle is harmless. If a marketing manager is freelancing for a direct competitor, you have a problem. Proactive transparency is the only way to prevent "accidental" ethical breaches.
The Solution: Implement a simple, one-page disclosure form for employees to list their side projects and clients.
Expert Tip: Frame this as a protective measure for the employee. Ask: "Will this work involve any of our competitors?" Finding these overlaps early allows you to find collaborative solutions before they become HR issues.
4. Leverage the "Hustle" Skillset
When an employee runs their own business, they become a "scrappy" problem solver. They learn to make data-driven decisions, manage tight budgets, and handle difficult customers.
The Opportunity: Don't let those skills stay siloed. If an employee is learning supply chain management through a side business, find ways to use that insight in your department.
Expert Tip: Try saying: "Your side project has given you a unique perspective on e-commerce trends. I’d love to hear how we might apply some of those insights here."
5. Offer Support That Reduces the "Need" to Hustle
Over 63% of side hustlers say they would scale back if they felt more supported by their primary employer. While pay is a factor, stability and growth are often just as important.
What Employees Want: According to the survey, 61% want upskilling opportunities, and 50% want regular updates on job stability.
Expert Tip: Address the root cause of their insecurity. Ask: "What support would help you feel more confident about your future here?" Transparent communication about company health often provides more peace of mind than a minor bonus.
The gig economy isn't shrinking—it's projected to reach over $2.5 trillion by 2035. Side hustles are a permanent fixture of the modern workplace.
The most effective leaders won't spend their time policing their employees' off-hours. Instead, they’ll build a culture of empathy, clear boundaries, and mutual growth. When your team feels secure and valued in their primary roles, they don't just work for you—they invest with you.