Got a thriving side job? Here's how and when to tell your boss about it — and why you probably should. (2024)

Forty-four percent of Americans had a side hustle in 2022, a 13% increase from 2020, according to an online survey of 2,073 US consumers between the ages of 18 and 76 from the financial services marketplace Lending Tree.The risk of a possible recession and layoffs across prominent companies could continue driving entrepreneurial folks toward an outlet for ancillary income this year, which makes the question of when and how to address a side hustle with managers increasingly pressing.

From a professional point of view, being transparent with your boss helps build trust. Besides, you wouldn't want your manager to find out about your side hustle from Instagram, especially if you're using the platform for marketing, said Susie Moore, a business coach and the author of "What If It Does Work Out?: How a Side Hustle Can Change Your Life."

"It's important to be upfront and honest," Moore said. "You're not hiding anything, and a side hustle is a worthy endeavor that shows you have initiative."

Insider spoke with three experts, including an entrepreneur who took her side hustle full time, who shared their advice and tips on how to have a productive conversation with your manager.

Steel your nerves

Research by Jennifer Nahrgang, a professor at the University of Iowa's Tippie College of Business, found that employees fear disclosing their side hustles to their bosses for a number of reasons. Some didn't want their managers to think they didn't have enough to do at work. Others were concerned about being judged for having a side hustle for financial reasons.

One of their biggest concerns, though, has to do with the so-called ideal-worker norm, she said. "There's this notion that ideal employees are devoted to their jobs and available 24/7," she said. "Some worry that having a side hustle may signal lack of commitment."

In a survey of 50 managers, Nahrgang found that about 35% of managers were supportive of their employees' side hustles; 30% were unbothered as long as the side hustle didn't interfere with their jobs; and 20% thought it wasn't their business. But a minority of managers were worried about employee burnout or concerned that their employees' side hustles would take time away from the organization.

Knowing these potential reservations can help you decide how best to broach the subject, she said.

Be transparent — to a point

If you're still in the ideation phase of entrepreneurship, Moore, the business coach, recommended keeping mum until you're sure you're going to pursue it. "You don't want to have a conversation with your boss about something you're feeling out if it's going to fizzle in a couple of months."

But if your side hustle is already a thriving business, you should mention it right away, she said.

When it comes to figuring out what to say, don't divulge more than you need to. Moore suggested saying something like, "There's this exciting thing that I do on evenings and weekends, and I find that I'm learning new skills that I use in my day job."

Don't be apologetic or act as though you're asking for permission, but there's also no need to be overly fawning. Don't say, for instance, that your side gig is your life's passion, and that you can't wait to do it full time.

Chase Coleman, a full time employee at Amazon, already had his side hustle as a content creator before joining the tech company. However, he disclosed this information to Amazon during his initial interviews.

"I would rather get out ahead of it than them find it and I feel like I'm getting fired because of it," he said.

His managers did not care if he had a side gig, as long as it wasn't impacting his work and that it didn't reflect the company poorly, Coleman said.

Talk about the benefits of your side hustle

Even bosses who greenlight side hustles want your full attention during work hours. "The minute you make a mistake or your performance slips, your boss might think you're not focused," Nahrgang said.

That's why it's critical to maintain a strong level of performance. Keep hitting your deadlines and meeting your goals. If you have a good relationship with your boss, consider having a frank conversation about how your full-time work benefits from the side hustle.

"Talk about what you're learning and highlight how it gives you a creative outlet that helps you be more energized and more satisfied with life and work," she said.

That's how Lissette Calveiro positioned her side gig to her manager in 2013. Calveiro is the founder of The Marketable Millennial — a blog focused on careers, mentoring, and breaking down the barriers to social-media influencing. In telling her boss about her venture, she explained how it allowed her to develop new skills that benefited her then employer, a PR company.

The experience she gained building her brand on social media, fostering a community, and marketing herself helped her do the same with clients at her full-time job, she said. When Calveiro's social platforms started growing, other teams at her company asked her to help improve their own results. Being transparent about her thriving business allowed Calveiro to help the company while simultaneously building her own.

Set boundaries for your time and energy

Finally, it's important to set parameters on how you'll divide your time and energy — and to make sure that your boss knows how you're reinforcing those boundaries.

"I highly believe in not just time management, but energy management," Calveiro said. "The things that drain your energy, dedicate time to it," she said, adding that sometimes those tasks should be saved for the weekends so as to not sacrifice the energy you need for the workday.

"If I tried to do it in between lunch breaks, I would come back for my lunch break drained," she said. "You want to protect your employer's space, you want to protect your own side-hustle space, and the more you cannot intermingle them, the better."