I’ve been freelancing on and off since I graduated college in 2013. It’s helped me make extra money, chase things I actually care about, and stay sharp during the gaps between full-time jobs. And truthfully, almost everything I’ve learned while freelancing has made me better at every 9-to-5 I’ve ever had.
Side hustles aren’t new, but the numbers are wild. Around 39% of working Americans report having a side hustle, which is roughly 80 million people. Among millennials specifically, that number climbs to 50%. And it’s not just a money grab. Nearly half of Gen Z and millennial side hustlers say their primary motivation is to be their own boss, while 42% are driven by the desire to pursue their passions.
Side hustling is clearly the norm now, not the exception. So if you’re a business owner or manager, the real question isn’t whether your employees have something going on the side. It’s how you’re going to handle it.
The old school take is that “moonlighting” is a red flag: a distraction, a foot out the door, a conflict of interest waiting to happen. I’d argue the opposite. The best employees I’ve ever managed had side hustles. They were ambitious, resourceful, and they made the whole team better. Here’s why.
They don’t wait for someone to hand them a solution.
When you freelance solo, there’s no one to escalate to. You figure it out or you lose the client. That muscle, the one that says okay, what are my options here instead of whose problem is this, translates directly into the workplace. Side hustlers tend to be the people who actually solve things, not just surface them.
They’re constantly getting better at their craft.
Employees with side gigs are learning outside of work hours, on their own dime and their own time. The skills they’re picking up, like client management, project scoping, communication, and learning new tools, all come back with them on Monday morning. It’s like a professional development conference that you didn’t have to budget for. (You should still invest in development for your team, obviously. But the point stands.)
You can learn from them (if you’re paying attention).
The worst managers I’ve encountered think learning flows in one direction. It doesn’t. The people on your team who are running their own thing on the side have figured out how to manage client relationships, juggle multiple projects, and maintain some semblance of work-life balance. If you’re smart, you ask about it. Some of what they’ve figured out might apply to how your whole team operates.
They have discipline that most people don’t.
Working a full day and then coming home to work on something else — not out of obligation, but because you’re building something — takes a specific kind of focus. 67% of side hustlers report experiencing burnout, which tells you how demanding it actually is. The people who do it anyway and do it well are showing you exactly what kind of employee they are.
How to actually support your side hustlers.
If you have someone on your team doing their own thing outside of work, supporting them is an investment in your relationship with them. They’ll trust you more, and they’ll be more likely to stay. Not because they have to, but because they want to.
A few ways to do that:
- Ask about it. Not in a surveillance way, but genuinely. Follow up. Show that you see them as a whole person, not just a job title.
- Ask what they’re learning. Invite them to bring new skills or processes back to the team if it makes sense.
- Be honest about the trajectory. Let them know you want them to grow, even if that eventually means outgrowing the role. Said with the right tone, this builds way more loyalty than pretending it’ll never happen.
- Give creative employees some breathing room. Even a few hours a week of “professional development” time can make a real difference in engagement and output.
The one thing you do need to sort out: conflicts of interest.
None of this means you ignore boundaries. If someone’s side work directly competes with your business or creates a real conflict, that’s a conversation worth having clearly and early, not just when it becomes a problem. That kind of transparency benefits everyone.
I’ve been on both sides of this equation for over a decade now. Side hustlers make better employees. Hire them. Support the ones you already have. And if you’re not side hustling yourself, maybe it’s worth asking why not.
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