Skip navigation

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."

homeoffice_Body.jpgby Robert Lerose.


At first glance, the thought of having your own office at home to run your small business can sound exciting. You'll have the freedom to set it up exactly the way you want, without having to conform to the restrictions of a corporate environment. For some business owners, that feeling of euphoria is short-lived when they realize that they don't have the expertise to design a workspace for maximum efficiency.


According to a U.S. Census Bureau report released in October 2012, an estimated 13.4 million people—or about 9.5 percent of the American workforce—worked at home at least one day per week in 2010. Even people who are typically well organized can easily find themselves overwhelmed by the endless tasks of managing paper flow, storing records, stockpiling equipment, and battling the clutter that mysteriously appears. Before the tower of reports and client files at the edge of your desk comes crashing down, here's some practical advice from three design and organization experts.


Be imaginative

Finding an adequate amount of space seems to top the list of priorities when planning a home office. Even when you think you've allotted a sufficient amount, it's not uncommon to outgrow it quicker than expected—a problem that can afflict professional designers, too.


"We actually have an office in our home that is the whole basement level, and we're always looking for more space," says John Loecke, partner in Madcap Cottage, a New York-based design firm. "If you have a really tiny home or studio apartment, maybe you're better off getting a space outside the home because you're always going to find you never have enough space."


For small business owners who want to stay put, however, Loecke suggests finding a space away from high traffic areas. Instead of using standard issue industrial office furniture, a vintage table or desk can transform a dull workspace into something unique. Loecke prefers natural light, as well as paint colors and decorations that reflect your personality.


Using your imagination can extend to other necessary but unattractive items, too. "Filing cabinets can be hidden inside of something or they can be skirted and hidden under a table top that's used for something else," Loecke says.


For example, Loecke faced a dual space and storage problem when he designed a home office for a mortgage broker who lived and worked in a one-bedroom apartment in Manhattan. "We did a wall of built-in cabinets that not only hid the desk which folded out, but also hid all of the cabinets," Loecke explains. "The desk chair got put away when everything was folded up. It didn't look or feel like an office, except when she needed it to function that way."


homeoffice_PQ.jpgFind your own system

Managing paper flow and being able to retrieve documents efficiently is an ongoing dilemma for many small business owners. As with designing an office that reflects your personality, establishing a filing system should match your individual way of thinking, too.


"Some people think linear from A-to-Z, others by categories, still others by merchants," says Kim Oser, a Certified Professional Organizer and owner of Need Another You, a Maryland-based service. "There's no one cookie cutter system for everybody."


Oser herself uses a monthly system created by FreedomFiler. Everything that is not a permanent or tax-related document goes into a monthly folder and gets deleted every two years.


"I set up two sets of monthly tabs: January through December odd year and January through December even year," Oser explains. "For example, this year we're in July, odd year. So when I got to July 1st, I had stuff in there from July 2011. I could take that whole stack and stick it in the shredder. So now I had an empty clean folder for anything that came in for July of this year. It self-recycles."


Storing old and current items can be perplexing, but Oser suggests using an A-B-C-D method to streamline the task. An "A" location is for items that are easily within reach when you're sitting at your desk. A "B" location is for items where you would have to swivel in your chair or reach down to pull out a file drawer. Items in a "C" location would require you to get up from your chair and walk across the room. And a "D" location is for items in a distant location, such as a basement.


Have a concrete plan

Thinking vertically—such as using tall bookshelves as opposed to short ones—is a particularly efficient use of space, especially in apartments or cramped spaces. Keeping your space free of senseless distractions is another.


"Be mindful of what I call beautiful clutter," says Angela Kantarellis, founder and owner of New York-based AKorganizing. "It's an item that has something in it, such as a container, that you don't use. You want to reduce, reuse, and recycle clutter."


For example, Kantarellis was doing some decluttering of her own when she came upon a binder and a beautiful leather notebook for business cards that she never used. She took the business cards out of the binder, so she could reuse the little plastic sheets for something else, and gave everything else to her sister.


One of Kantarellis's pet peeves is what she calls the Someday/Somehow Syndrome: setting a worthwhile goal that never seems to get done because there is no concrete plan. To counteract that, she suggests setting goals that are specific, measurable, attainable, realistic and time-bound, or what goal-setting experts call SMART for short. For example, saying that you will organize your files by a particular date, instead of getting around to it someday.


Spending time at the end of every day—15 to 30 minutes—to organize your desk and writing down your plans for the next day can be a huge boost to productivity. "Keep your files rotating, so you only have active files on your desk," Kantarellis says. "Do a seasonal review—say, every quarter—in addition to the daily decluttering. Keep the files that are no longer important or active in your archives in a different place."


Small business owners can find an assortment of filing systems today. For a client who hated traditional filing systems, Kantarellis found a multi-drawer storage cabinet, manufactured by Bisley, and also available at The Container Store. "He was able to stack things in piles based on projects," Kantarellis says, which eliminated the stress and clutter in his office.


Taken as a fun challenge, organizing your home office may actually be good for your bottom line and your disposition.

Filter Article

By tag: