OnTheSide_Body.jpgby Erin McDermott.


When you’re doing what you love, the day doesn’t end at five o’clock.


For many following their entrepreneurial passions, eight hours at the office is followed by the next shift: at their side business. The motivations are varied. Some folks dream of self-employment, while others want a hobby that provides a lucrative outlet, or maybe a backup plan for an uncertain economy. The American economy is full of success stories that began in a lamp-lit garage or on a basement desktop computer late at night.


But until you can make the leap to go solo, there’s a rocky road to navigate. On the one hand there are the demands of a bill-paying career and a relationship or family responsibilities. On the other is the pull of that side business that taps into your true passion. How do you keep these worlds from colliding in disaster? Here’s a look at people who are making these epic multitasks work, and the lessons they learned along the way.


Keep your schedule consistent

Jason Swett says he struggled in his initial attempts to juggle a software engineering career while launching Snip Salon Software, an appointment-management suite he built in his off hours for the hair-stylist market. While each of those endeavors was formidable, he says he didn’t see the effect these commitments had on something more important: his relationship with his wife.

To better manage his hours, Swett decided to work freelance while pouring the majority of his efforts into getting Snip off the ground. Looking back, he says he failed to grasp how unpredictable those outside assignments would be, and the difficultly of scheduling work hours around the unknown. “The idea sounded great on paper but didn't work out well in reality,” he says. “It can be a boom-or-bust situation, and no one was happy.”

What did work: Swett says he now gets up at 6 a.m. to put in a few hours work on Snip, before his family wakes up and he heads off to his full-time job. He’s able to put in two hours a day and stays in email contact with clients, who know his schedule and are on board. And even at his regular place of work, his supervisors and colleagues know about his unrelated side business, where his experience has sometimes given him a leg up. “It cross-pollinates at times,” Swett says, adding that Internet service vendor sidelines aren’t all that uncommon in the IT world. “When we’re facing a problem, I’ve said ‘I’ve faced this decision before at Snip, and this is how I handled it….’ I was in a position to give some unique advice and I think they appreciated that.”

OnTheSide_PQ.jpgManage your time wisely

Behold the power of the smartphone. Answer emails on break, return calls from a client on a coffee run, or set up meet-and-greets over lunch hours. Leave clerical and administrative tasks to the weekends, if possible. And use calendars everywhere, on the smartphone, on email, on the wall, and on your desk.


Be clear about why you’re doing it

It never hurts to have a Plan B these days. Mark Mason was long fascinated by Internet marketing. So, he started educating himself on the specifics after work from his job at a Dallas-area Fortune 500 company in the early 2000s. When rounds of downsizing hit, his position survived. But, shaken by the experience, he started to look more seriously at his “cash-flow positive hobby.”

“It was something that could be a business and something I looked forward to doing every day,” Mason explains. These days, he’s focusing more on helping other side-jobbers get their start in the business, providing the help he never found during his early days, largely through his podcast, Late Night Internet Marketing. His main message on how to manage the balance: Know why you have the side job, know why you have the regular job, and know how much you value your personal life—and be present for all three. His “why” for his sideline: “I’m passionate about helping people and I get these emails from people about how I’ve helped them change their lives,” he says. “That’s why I’m doing it. That’s what helps me focus.”

SBC newsletter logo.gifDon’t get overwhelmed

Katie Niemeyer’s a runner. But when she run in the Texas heat, sweat would trickle down her forehead and sting her eyes, which are still sensitive from a severe adverse reaction she had to a medication as a teenager. That’s how she found her niche. Instead of using a bandana wrapped around her hand or the ’80s-style terry-cloth headbands she saw online, late last year she came up with an idea about how to keep the sweat beads at bay. She created the Handana wrap, a modified wristband that athletes can wear on their hands to wipe away accumulating moisture. Within six months she had orders from (OK?)  stores all over North America and offered the wraps to runners at the Disney Princess Half Marathon in Orlando, Florida.

What worked for Niemeyer: Don’t aim to rush from A to Z; start by focusing on A to B. When she wasn’t at her job as a certified registered nurse anesthetist or spending time with her kids, she took her Handana work one step at a time, finding her Dallas-area manufacturer through a hospital colleague with her own line of medical scrubs. “I guess it was good that I was naive enough to just go step by step,” she says. “If someone said I had to be on a talk show with these in six months or selling in Europe, I wouldn’t have gone for that. It’s just a steady pace, week by week of what the next step is. But if doors keep opening, I’m going through them."

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