Moonlighting: Should You Tell Your Boss?

July 2, 2009 — -- When fitness buff Amanda Furgiuele began teaching pole-dancing classes after work two years ago, she didn't broadcast it to colleagues at her day job as a television producer.

"Although I know that pole dancing is a legitimate fitness pursuit, most people still refer to it as 'stripping class,'" said the Maui, Hawaii resident, who has never worked as a exotic dancer and does not allow nudity in her classes. "I was kind of worried about the social stigma. I didn't want to appear unprofessional."

Despite her discretion, it didn't take long before Furgiuele's co-workers found out.

"One of my student's cousins was my office manager," she said. From there, it was only a matter of minutes before her evening occupation was laid bare before the entire office.

"After a thorough round of teasing and a few moderately inappropriate comments, it's mostly smoothed out at my day job," Furgiuele said. "I'm glad everyone knew me as a person before they knew my 'other profession.' I'm not sure they would have been so understanding had they thought of me as a pole dancer first."

According to a January survey conducted by The Daily Beast, 23 percent of those polled have more than one paying job. Some said their second job was a hobby that had morphed into a money-making operation. Others said they needed the extra income.

So does the fact that we've become a nation of cash-strapped moonlighters mean that your employer will support your after-hours vocation? Or could fessing up that you've been serving cocktails, driving a limo or designing canine outerwear on the side jeopardize your reputation, or worse, your day job?

The short answer is, it depends.

Spilling the Beans About Second Jobs

"Moonlighting is sort of the American way," said employment attorney John Robinson of the Florida law firm Fowler White Boggs. "It only becomes a problem if it interferes with your primary job."

Obviously, running a side business from your cubicle is a no-no. Ditto for stealing your employer's customers or showing up to work exhausted because you've been burning the midnight oil at your other gig.

Jeannie, a business development administrator at a San Diego construction company, had these golden rules in mind when seeking part-time work in October once business got slow. Her side gig? Working for a children's birthday party entertainment company on weekends ("I've been a clown, an elf, a fairy, a princess and a pop star," she said).

Because her part-time job didn't affect her Monday through Friday work, she decided to come clean with her employer right away.

"I figured it was better to explain myself and make light of the situation on my own terms," said Jeannie, who didn't want her last name mentioned. "My worst nightmare would be to show up at a co-worker's house for their kid's birthday party dressed as a clown or fairy."

The reaction at her office?

"People here love it -- they're always asking about my parties," Jeannie said. "I think people are more understanding of side gigs now than they would have been a few years ago. People have even said it's admirable that I'm doing what I need to do to make sure I can make my house payment and have money saved up for emergencies."

Avoiding a Conflict of Interest

Of course, not all moonlighting gigs are created equal, reminded Robinson.

"If you're going to be up there naked and dancing on stage and you work for a church, that's a problem," he said.

Likewise, he added, "If you're someone who's working at a nuclear power plant during the day, I think your employer's entitled to say that's your only job. You shouldn't be out at night leading fishing tours."

Some employers maintain a no-moonlighting policy. Others have a non-compete policy that forbids employees from working for industry competitors. Understandably, they want your undivided loyalty and they want you to keep their trade secrets quiet.

Even so, some workers find their employer's attitude toward moonlighting oppressive.

Take Michael (not his real name), a freelance designer in Cincinnati. Before striking out on his own in December, he worked for a company that allowed its creative staff to take freelance jobs paying less than $10,000 -- pending their manager's approval.

"The catch was that the manager would never take time to officially approve your request," said Michael, who moonlighted first for the extra cash, then to build up his own business. "So you either lost the client because of the long approval period, had to let the client go because the wait was embarrassingly long or just said 'screw it' and did it."

While it's rare to see a company sue an employee who's been two-timing them, if you don't abide by an employer's moonlighting policies you do run the risk of being fired, Robinson said.

A New York marketing professional I'll call Sarah is willing to take that chance. Although she isn't sure her employer would approve of her writing research reports on the side to line her savings account, she likes "the security of knowing you haven't put all your eggs in one basket."

Given the economy, she said, "It really makes me feel a lot less nervous about getting laid off from my day job."

This work is the opinion of the columnist and in no way reflects the opinion of ABC News.

Michelle Goodman is a freelance journalist, author and former cubicle dweller. Her books — "My So-Called Freelance Life: How to Survive and Thrive as a Creative Professional for Hire" and "The Anti 9-to-5 Guide: Practical Career Advice for Women Who Think Outside the Cube" -- offer an irreverent take on the traditional career guide. More tips on career change, flex work and the freelance life can be found on her blog, Anti9to5Guide.com.