Side Hustle

5 Questions to Ask Yourself Before Starting Your Side Hustle

If you think you're ready to turn that business idea that's been simmering in your brain into a full-fledged business, read these tips first to get started on the right foot.
5 Questions to Ask Yourself Before Starting Your Side Hustle
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The following excerpt is from Jessica Abo’s book Unfiltered: How to Be as Happy as You Look on Social Media. Buy it now from Amazon | Barnes & Noble | iBooks | IndieBound

If you’ve been sitting on an idea and feel it’s time to pursue it, be ready for the amount of time and energy it will require. If you can work a full-time job and get your side hustle up and running (before or after work, on the weekends, and on your vacation), you may find that road to be best. Here’s the story of one entrepreneur who did just that, along with some tips for doing that yourself.

Shawna Lidsky had been working as a sports broadcaster for more than 12 years and could feel the tide shifting in local media. More cable channels were popping up, and job security was low. She knew it would be a tough job when the time came to start a family since sporting events mainly take place at night and on weekends. She also wanted more vacation time and flexibility, but her news station in Vermont required her to work there for 15 years before getting a third week of vacation time. Shawna says the job was a great gig in her twenties and early thirties, but she couldn’t envision doing it forever.

While she’d only made brownies from boxes, she thought it would be cool to source local ingredients and make a product that Vermonters could be really proud of and enjoy. As she says, “I love the Vermont lifestyle and had the crazy idea of capturing that in a brownie.”

Sometimes the best way to incorporate a side hustle is to blend it with your day job. You can’t always draw stark lines between the life you have now and the life you want. When that happens, think of ways you can test your ideas for the new gig while maintaining the status quo at your day job.

For example, Shawna started playing with different brownie recipes before and after her news shifts and on the weekends. With an exhausting work schedule, no business background and no professional baking experience, it seemed like the perfect recipe for disaster. But the key to her success was not biting off more than she could chew. She didn’t have a business idea one day and quit her job the next. Instead, she brought every batch of brownies she made into the newsroom for everyone to try. Her colleagues were happy to eat the brownies and give her unsolicited feedback, and she was thrilled to turn them into an informal focus group. No one knew she was starting a business, so she stored away their opinions. When Shawna got laid off from the newsroom due to budget cuts, she had a decision to make: apply for another TV job or pursue her business full time. She decided it was brownies or bust, and the Vermont Brownie Company (VBC) was born.

Long before you start thinking about quitting your full-time job, Shawna recommends asking yourself these questions:

1. Do I have the time and money my idea needs? Shawna was willing to spend all her free time in the kitchen, but she didn’t want to burn through too much money too soon. At first, she even mixed the brownies with a spoon because she didn’t own a mixer! Her then-boyfriend (now husband) attached a wire hanger to a drill to make her one. Disclaimer: Do not try this at home.

2. Have I read books or spoken to entrepreneurs to find out what I’m really getting myself into? Shawna admits she was so concerned about not knowing how to bake that she almost threw in her apron before she even started. She dug into reading books on entrepreneurship and found a resonating theme that marketing was just as powerful a skill as baking, if not more so.

3. Can I handle extreme highs and extreme lows? In Shawna’s case, she almost put herself out of business before she began. She asked friends and family to have a few people over to their homes to sample different flavors, and she gave everyone who attended a cou­pon for 50 percent off. One woman gave her coupon card to her husband, who then ordered $4,000 in corporate gifts. Shawna couldn’t produce $4,000 in product for $2,000 when she was just getting her company off the ground. She went from being excited by such a big order to nervous her business would be destroyed. Luckily, she survived this snafu and had the stomach to handle the stress.

4. Am I OK not getting a paycheck the first year? “You have to be willing to sacrifice the exact things you hope to gain back over time; making money is one of them,” Shawna says. You need to be aware of what you have to spend while knowing you won’t be making bank deposits into your account any time soon.

5. Am I comfortable working with people who are better than I am at certain things and who are often smarter than I am? “Ignorance on fire is bet­ter than knowledge on ice,” Shawna says. “There was a whole lot of ignorance on fire during the startup phase, and working with people who were experts in marketing and packaging was vital to VBC’s success.”

Shawna also encourages you to:

  • Surround yourself with great people.
  • Remember there are very few problems that don’t have solutions. You just have to go out and find them.
  • Forget the idea that others have it easier than you. Your business is not the only one struggling! Every business model has flaws unique to its industry or product.
  • Keep in mind, transition is scary (even when it’s good).
  • Always remember the most challenging and scariest opportuni­ties often reap the greatest rewards.

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