How A Side Gig Can Be Your Key To Career Satisfaction

Moonlighting isn’t just a way to earn extra cash; done right, it can transform and enrich your career.

How A Side Gig Can Be Your Key To Career Satisfaction
[Photo: courtesy of Framebridge]

Susan Tynan was working at LivingSocial, managing its home services division, when the idea for her own business came to her. She noticed customers weren’t happy with the framing services being offered and thought: “There must be a better way to do this.”


She began to really pay attention to what customers were and weren’t satisfied with. “I did most of the customer development as my side project,” says Tynan, who founded Framebridge in early 2014, after leaving LivingSocial and doing a brief stint at a startup called Taxi Magic (now Curb).

While she didn’t found her company until after leaving her full-time jobs, so much of the inspiration for Framebridge was formed during her time working elsewhere. “Your career makes more sense in reverse,” she says. “When you look back at it, everything looks like a stair step leading to where you are.”

Having a side gig to work on outside of your regular job isn’t just about earning extra cash. Most importantly, a side project offers the opportunity to do meaningful work that can promote career growth and satisfaction. “Choosing a side gig is deeply personal; the right one fits like a favorite pair of jeans, stretchy in all the right places,” writes Kimberly Palmer in her book The Economy of You. “Side-giggers find ways to exploit their unique skills and interests along with what’s currently marketable.”

But where to begin? Here are four key components to consider when taking up a side project that can enrich your career and experience.

Pinpointing Your Sweet Spot

It’s important to think through what work might be most meaningful and fulfilling to you outside your regular job. Palmer, who spoke with people across industries about how and why they launched their side jobs, says taking the time to assess where to focus your attention is a critical early step. What topics do you seem to naturally gravitate toward in your free time, when talking with friends, or when spending time online? Are there particular ways you most like helping others, or unique skills you aren’t using at your job?


Think about what gives you pleasure and how you can focus more time on a side gig as a way in. Palmer also suggests talking with others who have already figured it out for themselves. “What do people you consider role models do to find new sources of income?” she says. Perhaps there’s part of your full-time job you enjoy doing but wish you could spend more time on outside the office.

Find Ways To Let A Side Gig Enhance Rather Than Distract From Your Job

For Tynan, the entrepreneurial bug was always there, but she made sure she stayed focused while at her day job, even as she grew more and more excited about starting her own business. “The only way former employers are going to like you is if you were fully devoted to your job,” says Tynan. For Framebridge, this was particularly important because, after founding the company, Tynan was able to bring on Living Social’s CEO as one of her first investors.

What’s more, that entrepreneurial spirit is one that employers are increasingly seeking out when hiring. One out of every three employers claim they actively look for entrepreneurship experience when recruiting, according to a survey by research firm, Millennial Branding, sited by Palmer.

“One of the richest sources of side-gig ideas, in fact, might be your day job,” she writes. “Finding a pursuit that makes your employer look good, or teaches you extra skills, such as html coding or public relations, that your employer can then use to its advantage, offers a double payout–earnings from the side gig as well as increased value at your job.”

The People Around You Might Come Along For The Ride

Today, Framebridge has 75 employees including its production staff, but of the company’s 20-person management team, 15 are former coworkers or people Tynan knew from previous jobs. Being able to maintain and draw from that strong network has been hugely important to the growth of the company and her ability to take it from a fledgling idea to a full-time business.


It’s clear you never want to burn bridges when going from one job to the next, but more importantly, keep your eyes open for others who might want to get involved and come along for the ride. “Working hard at the work we were doing while daydreaming was good for the company, but it was good for us as well,” says Tynan of her time spent brainstorming and developing the idea for Framebridge.

What Makes For A Strong Side Gig?

Having a meaningful side project won’t always mean you’re bringing in outside income. But it does create the opportunity to enhance your work life so that you can get more out of your existing job and feel more fulfilled by the work you’re doing.

Still, logistics will always play an important role. You want your side gig to have a low startup cost; be easily scalable; and work well with a flexible schedule. But most importantly, it should focus on your unique skills and how they can contribute to a larger story. “Successful side-giggers ask: What fields are growing?” writes Palmer. “What does this world need? What problems can I solve?”

Related: Are You Ready To Go Freelance?

About the author

Jane Porter writes about creativity, business, technology, health, education and literature. She's a 2013 Emerging Writing Fellow with the Center For Fiction