Alan R. Simon - Side Hustles For Dummies

Cindy majored in mechanical engineering in college. These days, she lives in Seattle and works for an aerospace company. She enjoys her full-time career, but on the weekends she really wants to forget her day job and enjoy the Seattle party and music scene. While Cindy was in college, she worked weekends as a bartender in one of the most popular bars near campus. Just because Cindy graduated and now has a “grown-up job” as a mechanical engineer doesn’t mean that her bartending days need to be in the past. Cindy makes an important decision: She’s going to do some sort of side hustle related to bartending!

Miguel was an accounting major during his college days in Boston. He stayed in Boston after graduating and is now a staff accountant at a large consumer products company. If you were to look at Miguel’s and Cindy’s résumés, at first glance the two of them would seem to have very little in common other than being fairly recent college graduates. But if you were to get to know Miguel and Cindy, you would learn that just like Cindy, Miguel also worked as a bartender during college and, likewise, has a continuing passion for the “mixology arts.”

Miguel, like Cindy, has a pretty straightforward 9-to-5, Monday-through-Friday work schedule. With his evenings and weekends almost always free, Miguel makes an important decision just like Cindy did: He’s going to do some sort of side hustle related to bartending.

Will Miguel wind up doing the same sort of bartending-related side hustle in Boston that Cindy does in Seattle? No! Why? Stay tuned, because selecting “bartending” as their respective side-hustle interest is only the first of many key decision points along the pathway toward finalizing all the specifics of a side hustle.

In the meantime, Cindy’s father, Sandy, has been a sports fanatic for his entire life. When Sandy was growing up many years ago, he played baseball, soccer, football, and basketball year-round. He also collected sports cards and memorabilia all the way from elementary school through high school. Eventually, though, Sandy’s interests shifted, and he stuffed all his baseball cards, football cards, autographs, and other sports collectibles into a dozen cardboard boxes. Originally, those cardboard boxes were stashed in the basement of his childhood home, but eventually they wound up in the attic of his current house, all still sealed tightly. In fact, Sandy hadn’t even looked at any of his old sports cards or other collectibles for years — until the start of the COVID-19 pandemic, when all of a sudden sports cards became wildly popular again. Now working from home, Sandy went up to the attic one Saturday, brushed away a bunch of cobwebs, and found and opened all those long-ignored boxes — and he was instantly overcome by a flood of nostalgia. Cindy had told her father about her own side-hustle ideas, which sparked a few of their own in Sandy’s mind. Cindy may be thinking about a side hustle related to bartending, but Sandy has a few ideas for side hustles related to baseball cards and sports memorabilia.

At the start of the COVID-19 pandemic, Lori’s hours working in a mall clothing store were cut way back. Fortunately, she kept her job because the store also has an online presence, and Lori was able to work from home packing and shipping orders for the store’s suddenly booming online business. But instead of working 40 hours a week, Lori was now working only about 20 hours a week, sometimes even less.

Unlike Cindy, Sandy, or Miguel, Lori doesn’t have any particular area of interest to turn into a side hustle. Still, she wants to — actually, she needs to — earn some extra money to supplement her weekly pay, which is now about half of what it used to be. Fortunately for Lori, many of the gig-economy delivery-oriented jobs went sky-high in popularity as people hunkered down in their homes. She signed up with Instacart and soon began spending about 20 or 30 hours a week shopping for groceries and other goods and then delivering those products to people’s homes.

In Lori’s case, you know exactly what she’s doing for her side hustle: working as an independent contractor for a gig-economy company, doing shopping and home delivery. But what about Cindy? Or Sandy? Or Miguel? You know that Cindy and Miguel are interested in bartending as their respective side hustles, while Sandy wants to do something related to sports memorabilia. But exactly what kind of side hustles will they wind up doing?

Cindy, Sandy, and Miguel all fall into the first of the two main side-hustle areas: choosing some topic that’s interesting to them as the foundation for their respective side hustles. They need to work their way through the progression of decisions covered in this chapter, and so far they’ve only reached Step 1: selecting a topical area.

Lori’s side hustle falls into the second area. She’s simply looking for some sort of flexible side hustle that doesn’t require any particular skill or passion, but from which she can still earn money above and beyond her regular paycheck.

Even if Lori’s hours at the mall hadn’t been cut, she could still head down this second side-hustle path. In fact, after businesses began reopening, the mall clothing store where she works — which, fortunately, was able to stay in business — increased Lori’s in-store schedule back up to 40 hours per week. Does Lori need to quit her Instacart side hustle? Absolutely not! She may scale back the number of hours she signs in and does shopping and delivery; or maybe she’ll keep the same level of Instacart activity but do more on the weekends and when she’s not working at the mall than she did when her day-job hours were cut.

Figure 2-1 illustrates the two main side-hustle “families” along with some great examples of specific side hustles for each one. Note, though, that Figure 2-1 only includes a small number of examples of specific side hustles. Plus, Figure 2-1 only includes the topical areas, not how to flesh out those subjects or topics into specifics, as you’ll see in the next section.

FIGURE 2-1:The two main side-hustle families.

Choosing a topical area of interest for your side hustle is only the first step. You then need to add substance and detail to your first idea and decide what exactly you’re going to do for your side hustle. You might do one or more of the following:

Perform some sort of service on a contract basis.

Sell some type of product, and maybe make the product as well.

Build online content to provide information.

Build online content to monetize yourself.

Monetize an asset.

Take on a part-time job as your side hustle.

Cindy and Miguel have both decided that a bartending-related side hustle is around the corner. Cindy decides that she’s going to do some bartending on the weekends for private parties. Miguel, however, decides to create a series of videos that he’ll upload to either YouTube or TikTok.

Many side hustles involve performing some kind of service, such as: