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You love your day job, but just have to scratch your entrepreneurial itch. How do you do it? Stay clear, don
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Serial entrepreneur Asher Epstein rises at 6 a.m. every day to take two hours of conference calls with an Israeli company for which he’s a consultant. At 8, he heads to his job, where he works with 25 different startups all day long, guiding them on the ins and outs of entrepreneurship. At night, he works freelance again, this time with an East Coast company.

Epstein uses the same skill sets in his freelance consulting that he does during his day job — helping companies grow. What he does – keeping a great day job while branching out on the side to feed his own entrepreneurial urgings – is far from uncommon, but it can be tough to juggle both.

“The key is to be unbelievably efficient with your time,” says Maryland-based Epstein. “Use nights and weekends for your second job, and make sure you’re staying focused on both opportunities.”

That’s exactly what Lesley Zwick did when she started Chocolate Impressions, a company that mounts photographs on chocolate as lagniappe at private events and corporate functions. Working full time as program director for a Detroit non-profit, Zwick made sales calls and printed chocolate before heading to the office at 10 a.m. After work, she’d do more for her side business.

“You’ve got to be real organized,” says Zwick, who juggled both jobs for a year and a half. “You’ve got to be able to manage your time and know what you’re getting into. I was fortunate that my boss knew what I was doing and was supportive of it, as long as it didn’t affect my work ethic and my working ability for my other job.”

That’s key, say those in the know. Don’t let your day job suffer from the demands of your side business.

It’s important to clearly and cleanly separate your two roles. “You don’t want your primary company claiming you were doing this on their time and therefore they have rights to it,” Epstein says.

It’s about time

“Mark off two to three hours a day when all you’re going to work on is your side business,” says Heidi M. Neck, an assistant professor at Babson College. “Instead of watching TV at night, work on your business.”

Such free time, as you’d expect, is one of the first things to go. You may have to forgo movies with friends, family barbecues and the like to keep on top of your business pursuits, Epstein cautions.

Build a plan for your new business, says Alan Carsrud, executive director of the Eugenio Pino Global Entrepreneurship Center at Miami’s Florida International University. Lay it all out so you’ll efficiently use your available time.

Also, carve out space in your house – the garage, basement or an extra bedroom – that’s just for your side business. Then add create stationery and business cards to give your burgeoning business “legitimacy,” Neck advises.

Consider the Conflict

How do you know if your sideline business is a threat to your day job? Easy. “If you’re working with the same customer base potentially, it’s confusing to both your company and your customers,” says Tim Faley, managing director of the Samuel Zell and Robert H. Lurie Institute for Entrepreneurial Studies at the University of Michigan.

“If you have a non-compete agreement then you’re pretty much forbidden from working in the industry for so many years after you leave,” Faley explains.

And do not try to hide what you’re doing from your boss. If you have to keep it undercover, then it is, or is going to be, a problem.

Know If and When You Should Quit

Many sideline entrepreneurs are happy to continue just as they are, without problems, if they take such common-sense tips to heart. But inevitably, success breeds growth and for some, the balance shifts. It’s an obvious signal that it’s time to think hard about giving up your day job or your side work.

“A lot of people do this during the startup phase,” Carsrud says. But when it becomes clear that you can’t continue to do both, a tough decision gets up in your face.

“It’s very hard to serve two masters,” he says. “There are some jobs where it’s an accepted part of the business model,” like writing, psychology or academia, where it’s not only OK to work on the side, it’s encouraged.

The turning point, Faley adds, is “when your passion and your time are more and more into the side project, your startup business.”

Lynne Meredith Schreiber is a freelance writer for StartupNation.

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