Side Hustles For Dummies. Alan R. Simon

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.

      WHEN WAS THE TERM SIDE HUSTLE COINED?

      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.

Knowing What You’re Looking for from a Side Hustle

      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!

      Money, money, money … money!

      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.

      CAN VOLUNTEER WORK BE A SIDE HUSTLE?

      Take another look at the broad definition of a side hustle: an activity outside of your full-time job in which you are materially invested. Maybe you’re materially invested in some type of volunteer work — dog walking a couple times each week at a nearby animal shelter, or being on the board of a local charity that assists homeless veterans. You aren’t getting any sort of pay for this volunteer activity, but it certainly takes up a fair amount of your time and needs to be balanced with your full-time job. So, could you think of your volunteer work as a side hustle?

      Well, maybe. If you limit the definition of a side hustle to an activity — any activity — that fits the “work equals pay” equation, then no, volunteer work isn’t really a side hustle. However, if you leave aside the compensation and income aspect of side hustles, you may, indeed, find a great deal of similarity between certain types of volunteer work and certain kinds of side hustles.

But now we’re diving deep into the terminology weeds, or splitting hairs, or whatever other metaphor you’d like to apply here. A better way to think of volunteer work and side hustles is that you could combine “traditional” side-hustle activities with your volunteer work to benefit a particular cause. You could, for example, write blog posts or create YouTube videos about your favorite cause, which bring in a little bit of advertisement-sponsored revenue. Or you could create an online retail site in Shopify and sell donated clothes — sort of an online thrift store. You could then (maybe after covering your costs) donate some or even all of your proceeds to your favorite charity. So essentially, you’re engaged in some sort of side-hustle activity, but you’re forgoing part of the “reward structure” — the income — for a good cause.

      Extending your knowledge and gaining experience

      Your journey into the world of side hustles might follow that fabled path of least resistance, where you embark on an activity or business