By Kathleen Furore
I recently spoke with someone whose side gig is growing and taking up more time than it had in the past – but it isn’t at the point where this entrepreneur can quit his full-time job, which he really enjoys. He gets great reviews, is close to his supervisor and is wondering if he should talk to her about his situation to see if there is a way to adjust his schedule.
I reached out to career search professionals and entrepreneurs, who all said essentially the same thing: Don’t let your full-time job get in the way of pursuing your dream, and approach the situation in an honest way with a dose of caution.
“You only live once! If your side gig is starting to take off and you fail to give it a fair shot to succeed, you’re going to wind up resenting your ‘day job’ – no matter how much you think you love it,” says Terry Kasdan, founder of and creative director for at Communications LLC, and an adjunct professor who teaches entrepreneurship in the University of Illinois’ Department of Advertising. “Ten or 20 years from now, you’re going to regret not taking a chance.”
Anna Kate Anderson, an executive resume writer and outplacement services provider, understands the desire to grow a business from scratch.
“It’s exciting when a side gig starts to grow, and you can see it being your full-time employment. I know because that’s exactly how I started my career services business,” says Anderson, who believes that approaching the subject with a supervisor is a good idea – provided that supervisor knows about the side gig and supports it.
“You may be able to ask for an adjusted schedule based on completing your work and showing that the side gig is not cutting into your regular, full-time job,” Anderson says. “If you can have an open, honest discussion – and if you can answer whether you will be leaving to support your side-gig full time, without worrying that you’ll lose your job – I say go for it. These kinds of supervisors are rare!”
Kasdan agrees, and notes that someone who loves their existing job likely has a supervisor who cares about them.
“If that’s the case, he or she should recognize the fact that you’re not just an employee but also a human being with your own dreams and aspirations,” Kasdan says. “Don’t be afraid to ask for reasonable accommodations that allow you to continue performing your current role but also enable you to pursue your passion. This might involve working from home a few days a week or adjusting your hours to arrive earlier or leave later in the day.”
However, Anderson does add one caveat.
“If the supervisor doesn’t know about the side gig, I would be cautious,” she says. “Instead of asking for a different schedule, I would set a time limit and/or revenue goal to help you boost your confidence in the side gig, and then think about asking for a different schedule or eventually leaving full-time employment. That could be as simple as [saying to yourself], ‘I’ll see where I am in six months,’ or ‘I’ll see how long it takes me to match my full salary with my side-gig.’ ”
Leadership brand and career strategist Karen Huller, founder of Epic Careering, also cautions that the right approach depends on the supervisor and organization. She says anyone wondering if they should discuss the situation with a supervisor should ask themselves a few questions before scheduling that meeting with the boss:
Is the company under-resourced?
How much am I asking to cut down?
Is the company historically friendly to flexible reporting?
Can I get done what needs to get done in fewer hours?
What accommodations will the company have to make in order to oblige?
Will I need to outsource some of their work? And can I delegate it?
If you do decide to move forward with the conversation, Huller says now is the time.
“Most companies in this climate would rather accommodate a valued employee than lose them and have to replace them. It’s an interesting job market, especially with talks of a looming recession,” she says. “If this person is going to approach his/her/their boss, it’s probably best to do it now than to wait.”
But do realize the risk, she adds.
“There’s no guaranteeing that the company/supervisor won’t look out for themselves and start to recruit for this person’s replacement in the case that the side gig takes over,” Huller says. “Perhaps they can agree to revisit in three months so that the company doesn’t feel that threatened.”
In the end, it’s really about how much risk you’re willing to take to pursue your dream, Kasdan says.
“As I frequently remind students in the entrepreneurship course I teach at the University of Illinois, employment opportunities come and go,” he says, “but the window of opportunity to turn a budding small business into a mature one doesn’t stay open long.”
– 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 email@example.com.
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