Side Hustling: Is It the Right Option for You?

One minute I’m speaking to a women’s group about my new novel. The next, I’m digressing about side hustling as a furniture restorer and my day job as a professional organizer. Before I know it, I’m mentioning my love for Bruce Springsteen.

As my workshop ends, all hands go up at once. One woman wants to know the best way to remove stains from an antique wooden door. Another woman wants to know how many times I have seen Springsteen. Another person asks me about a portion of my book that is all about how Italian Americans make Sunday gravy. Before I can figure out how any of these questions relate to my new novel, I realize that I have a long line of people waiting to purchase my book.

Swirling, aka side hustling

Among the readers is an energetic and stylish woman named Betty Galvan. “It was great listening to you. I am a swirler, too,” she says with a wink. My look of puzzlement begs a definition. She tells me that a ‘swirler’ is a term coined by screenwriter, author and publicity and content strategist Melissa Cassera. ‘Swirler’ refers to someone who incorporates all of the best parts of themselves into one uber-career or brand. Galvan began her swirly career in teaching while side hustling at a beauty salon. That led to a successful blog and job in digital marketing. Today she has combined all of those passions into career advice as she helps other Swirlers navigate business success in the worlds of digital marketing and social media with her company My Friend Betty Says.

This meaning of “swirling” might be new, but the concept of creating more income is not. People have been moonlighting, taking side jobs and even investing in real estate to create more revenue streams for generations. Up until this point, I mistakenly labeled my career habits as a bored, “Jacklyn of all, mistress of nothing” type. But new times call for a new definition. So, I went to Cassera, who literally wrote the workbook on swirling. The Swirl Effect explains the importance of combining your passions with business success

“When you are doing an activity that’s one of your passions, you feel like the absolute best version of yourself,” she says. “Once I figured that out, it transformed my business. I quadrupled my revenue, building a business that brings in multiple six figures every single year.” 

Side hustlers are mostly Millennials and Gen Z.

I had an epiphany after talking with her, as I am sure most people do. The conversation made me realize that I had been swirling my entire life. I moonlighted on my publishing career with professional organizing and began writing my novel while refinishing furniture. Like Galvan, I have always had a side job, or in today’s parlance, a side hustle. “Hustle” is a term I became familiar with while listening to Ann Shoket present her book, The Big Life. The book devotes significant space to the importance of the side hustle, an opportunity to learn something new on your own time. Shoket’s book is directed toward the millennial, which is no surprise. She spent the first part of her career building the confidence of young women as the editor-in-chief at Seventeen magazine.

According to a 2022 Zapier report, 59% of Generation Z and 61% of millennial respondents currently have a side hustle, while only 36% of Generation X and 22% of baby boomers said the same. Additionally, 60% of Gen Z and 55% of millennials were planning to start a side hustle at some point in 2022 at the time they were surveyed, with only 35% of Gen X and 13% of baby boomers reporting the same thing. 

Nick Loper is founder and chief side hustler of Side Hustle Nation. He says he sees this trend as strong among millennials more out of necessity than passion. “We’ve seen the cost of housing, education and healthcare skyrocket over the past 30 years while wages have been flat,” he says.

Loper cites the popularity of his site as a societal trend that is growing among the millennials and beyond. He attributes this increase to a “proactive drive to take over our financial lives.”

Loper took back his own financial life when he took his original side hustle, a comparison-shopping site for footwear, into a full-time business. He later realized his passion was talking about business and marketing, and created his site as a resource for people to take control over their own financial well-being through entrepreneurship. “And that’s really what the hustle is about: being proactive about the one thing you can control, your own effort,” he says.

Become an entrepreneur without quitting your day job

The idea of side hustling can be comforting for someone who has a business idea and is reluctant to quit their job. It can also be an intimidating and often unrealistic proposition. Chris Guillebeau founded Side Hustle School to help people create an all-new source of income without quitting their day job.

“This is critical, because these days everyone is being told that they should become an entrepreneur, but not everyone wants to do that. Everyone, however, wants more money and more options,” he says. 

Guillebeau’s podcast assists in his mission through its focus on sharing how people came up with their ideas, and the mistakes and money they have made. He differentiates the side hustle from the gig-based economy, which implies contract work with short-term engagements. “I’m focused on helping people create assets for themselves, not just more work, or a part-time job. I’m interested in stories of people who wake up in the morning, check their phone and see that they’ve made $200 while they were sleeping,” he says.

Loper recommends starting small with the ‘Side Hustle Snowball.’ Itemize out your monthly expenses and then try to erase those with income streams outside of your day job. “It’s intimidating to try and replace your day job salary right out of the gate,” he says. 

And for those of you still trying to decide which term defines you, in the words of Cassera, “Swirl on!”

This article was published in October 2017 and has been updated. Photo by Viktoriia Hnatiuk/Shutterstock

Mary Carlomagno is the owner of Order, which specializes in clutter control, urban apartment solutions, office spaces and shopping addictions. Mary’s philosophy is simple: do not let clutter control your life. Her easy-going approach, sense of style and strong communication skills create an atmosphere that makes organizing fun. She is the author of three books, Give it Up! My Year of Learning to Live Better with Less, Secrets Of Simplicity and Live More, Want Less. Mary has been featured on The Oprah Winfrey Show, The Today Show, CBS News, in Redbook, Real Simple and Woman’s Day. She has been interviewed on National Public Radio, the Joan Hamburg Show and Martha Stewart Living.

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