Alan R. Simon - Side Hustles For Dummies

Eric and Brittany had been single-mindedly focused on their respective full-time careers, both before they met as well as after they began dating and eventually got married. Eric is a high school teacher, while Brittany is a drug sales rep for a large pharmaceutical company. When the COVID-19 pandemic hit in early 2020, however, both of their professional worlds turned upside down. Eric continued teaching but solely online because his high school switched over to all-online courses. Brittany’s job was eliminated as part of the pharmaceutical company’s cutbacks, and she began working 15 to 20 hours a week shopping and delivering groceries for Instacart. As the months went by, Brittany also began delivering meals for both Grubhub and Uber Eats, as well as occasionally driving for Lyft. Eric began doing college entrance exam tutoring on the side, in addition to his full-time teaching. Eric is now wondering if he should quit his full-time teaching job and not only do even more SAT and ACT tutoring, but maybe even do some Lyft or Uber driving.

Pop quiz time!

From the blurbs above, who is in the side-hustle game? Meghan and her Uber driving? Jack and his community college teaching? Bhavna and her online boutique? Brittany and her portfolio of gig-economy jobs? Eric and his college entrance exam tutoring?

If you answered “all of the above,” you’re absolutely correct. Even though the particulars for what Meghan, Jack, Bhavna, Eric, and Brittany are doing vary at least a little bit from one person to the next, each one of them has already jumped onto the side-hustle bandwagon.

Some side hustles are actually part-time jobs rather than a small business or some gig-economy side work. In fact, you get paid for your side hustle through a regular paycheck — just like most day jobs — rather than in the less-than-predictable manner of most side businesses.

Take Jack, the Scottsdale software developer. Jack doesn’t have a side business in the traditional sense. He’s not creating and trying to sell instructional videos about software development or other technology-related topics. He does sign class-by-class contracts for each course that he teaches at the community college, but he gets paid through the college’s standard biweekly payroll on a W-2 basis while he’s teaching. If Jack isn’t teaching during some stretch of time — say, the first part of the summer, or during the latter part of a spring semester — then Jack doesn’t get paid anything. Basically, Jack is a part-time, on-and-off employee of the community college, rather than, say, an outside consultant.

But is Jack “materially invested” in his part-time teaching? Well, he teaches on a regular basis, most of the year (including at least part of each summer), and has been doing so for the past three years. He spends 10 to 15 hours a week while he’s “on the clock” on his teaching gig, between the classroom and other support activities such as grading and holding office hours to meet with his students. And he’s doing all this while holding down his full-time job, so you could definitely say that Jack is hustling!

Other side hustles come in what you could think of as a “convenient multipack,” packaged with other side hustles.

Take Eric and Brittany. Brittany no longer has a full-time job because her now-former employer laid her off during the COVID-19 pandemic. Instead, Brittany has her own small portfolio of what might otherwise be side jobs for someone who was employed full-time. Does the absence of a full-time job exclude any of Brittany’s side gigs — Instacart, Grubhub, Uber Eats, Lyft — from being considered a side hustle? Absolutely not!

In fact, Brittany’s little portfolio of side gigs — yes, that’s right, side hustles — in lieu of a full-time job is becoming increasingly common (see “ Seeing the Connection between Side Hustles and the Gig Economy,” later in this chapter). In fact, notice that Brittany’s husband, Eric, is contemplating voluntarily leaving his full-time teaching job and joining Brittany with his own portfolio of side hustles.

Other side hustles are much more like running a regular full-time business rather than a “here and there, whenever you feel like it” side activity. You don’t have the leeway to just say, “Nah, I don’t feel like packing and shipping a couple dozen customer orders this weekend, I want to go skiing. They can just wait for their jewelry, even if they paid for two-day shipping. I’ll get around to filling those orders early next week….” Nope!

Bhavna’s boutique, which she runs in addition to working her full-time, career-track engineering job, isn’t any sort of gig-economy activity that she can sign in to or out of on a moment’s notice. Running an online business entails regular commitment and being proactively responsive to her customers’ needs: processing and fulfilling orders, restocking inventory, addressing problems with suppliers, handling returns, and all the rest. Although Meghan, Brittany, and anyone else who delivers groceries for Instacart or drives for Uber or Lyft can arbitrarily choose not to engage in those activities if they’re too tired or just aren’t “feeling it” for a couple of days, Bhavna can’t necessarily “go dark” on her business for too long of a stretch.

But does Bhavna have a side hustle going? Absolutely — every bit as much as Brittany, Eric, Jack, and Meghan do.

Back in the early ’80s when I started my first side hustle, I called what I did a side consulting business or described what I was doing as moonlighting. The term side hustle wasn’t used very commonly back then.

However, according to Merriam-Webster ( www.merriam-webster.com/words-at-play/words-were-watching-side-hustle ), the phrase dates back to the 1950s! So, even though the popularity of the term side hustle may seem to be a recent phenomenon, the phrase dates back many decades, just as side hustles themselves do.

People start side hustles for a variety of reasons. For many people, money is the prime motivator. But to some people, the financial side of their side hustle is so secondary that it’s almost an afterthought.

So, why are you interested in a side hustle? Maybe it’s money, knowledge, or experience. Maybe you’re hoping to make a big career change. Maybe you’re looking to monetize a hobby or passion. Maybe you want a safety net in place in case you get laid off. Or maybe you’re trying to make ends meet after losing your full-time job. Whatever the reason, a side hustle can be right for you!

Our professional lives are hallmarked by a simple, straightforward equation: Work equals pay. Or, stated a bit more broadly: You put forth effort and provide value, and in exchange, someone pays you for your labors.

Many people are satisfied with what they earn from their full-time jobs, so the idea of making more money from some type of side hustle isn’t exactly top of mind.

For many others, however, their full-time jobs may come up short on the financial side. Maybe they make just enough to pay the bills and save a little, but their kids’ college tuition is on the horizon in a couple of years, and they’re not sure how they’ll afford it. Or maybe they want to pay for a wedding or a dream vacation that’s been on hold for too long.

Whatever the reason, doing something on the side — yep, a side hustle — may be the answer for how you can have your professional cake and eat it, too. In other words: Continue to hold down a full-time job that provides stability and benefits (even though the financial side isn’t quite what you’re looking for), while still earning money above and beyond what comes from your job.