The Fine Art Of Mastering The Side Hustle

Working a second job after hours can be rewarding if you know how to manage the extra demands without going crazy.

The Fine Art Of Mastering The Side Hustle
[Photo: Flickr user Janne Hellsten]

When Christine Hebbring and Jennifer Murray first decided to start a side business, it was less about making money and more about making room.


After years of “treasure hunting” at flea markets, Goodwill stores and other local consignment shops, the Milwaukee, Wisc.-area best friends said their homes were packed to the gills with the vintage-style goods and furniture they call “farmhouse swag.”

So early last year, they started posting messages on Facebook pages for “Buy, Sell, Trade” groups in the area and meeting up with interested buyers in local parking lots.

“It became total mania,” said Christine. “It was like we had groupies–as soon as we would post stuff on Facebook, it would sell.”

Spotting an opportunity, the women launched their own vintage-inspired home goods retail site, Painted Fox Treasures, about a year ago. Now, they say, the business is doing so well it’s changed their financial reality.

“So many times, we just laugh out loud that this thing that was a dream is, for all intents and purposes, coming true. We’re almost afraid to say it out loud,” said Christine. “It’s made the difference as two women with kids. It’s taken off that financial edge.”

Maybe at some point in the future–if the company became so successful it wouldn’t be a source of daily stress–they’d consider doing it full time. But both Christine, a second grade teacher, and Jen, who helps run her family’s business, said part of the joy of Painted Fox is its part-time nature.


The two-career two-step

And they’re hardly alone in embracing the two-career two-step. Thanks to new technology and digital tools that support small businesses, as well as an up-and-down economy, the side gig is going mainstream. More and more small business owners I meet are juggling their own ventures with a 9-to-5 job. And, personally, I can attest that it can be hugely rewarding–both personally and financially. About two years ago, I decided to turn my own passion for yoga into a profitable side venture, and I’ve never looked back.

If it’s something you’re considering, here are a few tips for making it work.

Be realistic about how it will fit into your life.
Chances are, your life already feels pretty full. So before you dive into the deep end of the small business world, do a quick inventory of your commitments and determine how much time and energy you’ll actually be able to give to your new enterprise.

Christine and Jen are both moms with day jobs. But Christine acknowledged that since her kids are out of high school, she has more time for a side business than she might have had during other points in her life.

If your schedule is packed but you still want to pursue your business, figure out where you can cut back on commitments or how you could find extra support.

Be prepared to sacrifice the extras.
Do you end each day with an episode of your favorite TV show? Or enjoy a weekly happy hour with friends? Get ready to say goodbye to regular downtime–at least in the beginning.


“You’ve got to be prepared to work,” said Jen. “We look at each other and, combined, we’re putting in unspeakable hours to this. Every one of them is worth it because we love the business. But it’s no wonder more people don’t to this.”

Still, they added, running a side business has helped them become more organized and disciplined with their time.

Create your own structure and accountability.
For many people, the side hustle often starts out as a passion project, not a profit engine. But because it’s a nice-to-have, not a need-to-have, it can be all too easy to let it fall to the bottom of your to-do list.

For Christine and Jen, working on Painted Fox as partners meant that they were accountable to each other. But if you’re forging ahead solo, build structure and accountability into the project through monthly meetups with other entrepreneurs in your area or regular check-ins with mentors and friends.

Automate and outsource wherever you can.
Launching your own company means being game to master whatever challenge is thrown your way. But to grow your business, you need to be smart about automating and outsourcing the tasks that don’t match up with your strengths.

When Christine and Jen first launched their company, they built their website on Squarespace. But within a year they migrated over to Shopify because it simplified the systems needed to run an online store. They also said that using accounting software removed the pressure of importing and organizing their financial information and gave them more time for the tasks they’re better suited for.


Be nice.
Life can get crazy when you’re juggling two jobs. You’ll probably be shouldering more stress and maybe struggling to manage a shorter fuse.

“Just be nice,” said Christine. You can’t build a business alone and you’ll likely find more helpful hands if you treat other people with kindness and respect.

Amy Vetter is the global vice president of education and head of accounting-USA at Xero, an online accounting software for small businesses.