By Kathleen Furore
With both remote work and “side hustles” becoming the norm, it has become easier than ever for employees to juggle multiple jobs behind the scenes. If someone is working a second job or starting a business on the side, should they let their primary employer know?
The career experts and business owners I reached out to all believe it is fine to have a side hustle.
“As long as an employee is producing high-quality work and is attending all required meetings, there’s little downside to having them engage in a side hustle,” Caleb Rule, inbound marketing manager at The Pedowitz Group, says.
“I sincerely believe that whatever my employee does in his free time is no longer under my control,” concurs Sherry Morgan, CEO and founder of Petsolino. “This means that if he decides to get a side hustle outside of the full-time job he has with me, it’s totally fine as long as it is not a conflict of interest with my company and he is not sacrificing his time for the job he has with me.”
Opinions differed, however, about how open a “side hustler” should be with an employer.
Rule advises keeping information about any “extra” job you might have to yourself. “What you do with your outside-of-work time is up to you,” he says, but he also notes two exceptions, including “potential conflicts of interest” or if it impacts “your ability to make a particular deadline.”
Rule continues, “I’d argue it’s a poor company culture if employees feel they have to report what they’re doing outside of work to their manager.”
Daniel Cook, who specializes in business development, HR, and team motivation at the law firm of Mullen and Mullen, takes the opposite view. He thinks people should be open about any side hustle. In fact, several employees have discussed their side hustles directly with him.
“Usually when an employee tells me about their side hustle, I try to be as supportive as possible, since these are trying times and employees are trying their best to establish their careers while providing for their families,” reports Cook, who cites one possible side benefit of sharing your side hustle: “It’s possible that they learn about your other skills through this and improve your job description.”
Cook also points out an unintended negative to keeping information from your primary employer.
“Hiding your side hustle from your boss could later on result in an awkward conversation when they find out about it from somewhere else,” he says. “Imagine your co-worker bringing up your work in front of your boss at lunch and you have no way to cover it up. Hence, it’s always better to be honest with your primary employer and gain their trust.”
No matter how you handle it, Rule stresses there are three things that employees working a side job should do:
- Manage your calendar. “For example, I have my lunch break blocked off on a daily basis, so if I have a side hustle call, I’ll take it at that time so as to not interrupt my workflow for my primary employer,” Rule explains.
- Give 100% to the primary employer. For many people (if not most), the primary employer is the primary source of income (and often of benefits too). “The side hustle is extra, and so your efforts should reflect that!” Rule says.
- Keep your side hustle and day job separate. “Otherwise, you risk blurring the lines of responsibility and using company resources for your own gain, which isn’t ethical,” Rule says. “Do the job you were hired to do.”
And there’s one thing that both employers who are worried an employee might be doing outside work on the company’s dime and employees who are tempted to beg out of a meeting so they can turn their attention to their side hustle should remember.
“For remote work, there are certain measures you can take to monitor employees such as the use of time and activity tracking software to prevent this type of situation,” Morgan says.
– Kathleen Furore is a Chicago-based writer and editor who has covered personal finance and other business-related topics for a variety of trade and consumer publications. You can email her your career questions at kfurore@yahoo.com.

