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15 years, my side hustle writing business and tech books not only earned a little bit of extra money, but also helped establish credibility in my day job. I reached a point, however, where I had maxed out the career benefit from business and tech writing, so it was time to switch to what I enjoyed more, which was writing novels.

      

You can follow the same strategy: Have some synergy between your full-time career and your side hustle at first, but eventually shift your side hustle to provide a break from your day job. Or you could head right for the “something different” road right from the very beginning.

Show Me the Side Hustle Money!

      Earlier in this chapter, I introduce you to Lori, who began doing gig-economy side-hustle work at Instacart when her hours at her full-time job were cut back. One of the main reasons Lori headed for the gig-economy side of the side-hustle world was the predictability of what she would make in exchange for her efforts. She was fairly confident that she could do 20 hours a week, maybe even a little more; and she knew what Instacart paid and what she could expect from customers’ tips in addition to her contract pay.

      Likewise, Jack, the Scottsdale software developer, is absolutely certain how much money he’ll make from his community college teaching side hustle — the payment amount for each class is right there in his teaching contract.

      Some side hustles come with highly predictable incomes. In Jack’s case, he knows exactly what he’ll make; in Lori’s case, she’s highly confident of the range in which her income will fall each week, and she knows that if she decides to work extra hours one week and fewer hours another week, she’ll make more or less money, respectively.

      But what about Cindy, the part-time weekend bartender? Cindy’s side-hustle income is less predictable than Lori’s or Jack’s. She won’t necessarily have a bartending gig every weekend, so in any given month, she could make more or less than she makes in another month, depending on how busy she is (or isn’t).

What about Miguel and his bartending videos? Or Mark and his accounting videos? Or Max and his hiking-and-biking-comedian-around-Boston videos? All three of these guys work together during the day, yet any one of them could be wildly successful with his side hustle while the other two could flop miserably and make little or no money. Or two of them could be successful; or perhaps none of them will be successful!

      Some side hustles come with highly predictable incomes, or at least a high confidence for the range of money you can make, while other side hustles could wind up bringing you anywhere from no money at all to literally millions of dollars! So, how do you align your side-hustle selection with your financial needs?

      

If you need your side hustle to help you cover monthly expenses or to meet some specific financial obligation, then choose one that comes with “guaranteed” — or at least predictable — income. Think of these types of side hustles as having “lockstep income” — in other words, the income you make from your side hustle moves more or less in lockstep with the effort that you spend on that side hustle.

      You don’t necessarily need to do a gig-economy job or a part-time job in pursuit of predictable income. Most of the time, a real estate–oriented side hustle such as a second home that you lease out, or a condo at a resort location that you rent through Airbnb or Vrbo, can also provide somewhat predictable income.

      But what about the various monetized videos that Miguel, Mark, and Max plan to do? Or whatever Sandy decides to do related to his recently rediscovered sports cards and memorabilia? True, none of those side hustles could turn out to be a winner … or each could bring in ginormous amounts of money!

      

Many side hustles are built around the concept of passive income, which is actually a widely misunderstood concept. Many people think that the term passive means “no work required” — sort of like a side-hustle version of the old Dire Straits song “Money for Nothing.” Actually, passive-income side hustles do require work, but that work and the resultant income do not typically occur in lockstep with one another.

Dhiraj creates a techie course that he uploads to Udemy. He spends three solid months on the course: recording and then editing the videos, creating assessments, producing the MP4 files, and then uploading everything to the account that he creates on the Udemy platform. As shown in Figure 2-3, Dhiraj spends 200 hours from the time he begins work on his course until the course is published. During that time, he makes absolutely no money at all from the course.

      The course starts slowly, but over the next three months (until the six-month point) Dhiraj pulls in $2,500. Not bad, especially because during those first three months that the course is active, he does almost no additional work! Basically, he’s sitting back and letting the money roll in, which means that he has now crossed the threshold and is earning passive income.

      FIGURE 2-3: A successful passive-income side hustle.

Over the next six months, Dhiraj pulls in another $23,000 ($8,000 in the second three months that the course is active, and then $15,000 during the following three months). During this entire time (refer to Figure 2-3), Dhiraj is still doing almost no work; in fact, he spends only about 25 additional hours after the course is published answering emails from people who purchased the course or maybe doing a small update here and there to include some new topic and keep his course fresh and up to date.

      

You have absolutely no ceiling on how much money you can make from passive-income side hustles, especially when you have more than one going — at least in theory. Max, Mark, and Miguel could conceivably bring in tens or hundreds of thousands of dollars each month if their respective videos catch on and the advertising and affiliate marketing money starts rolling in.

However, those three guys — Max, Mark, and Miguel — could also theoretically make little or no money from their videos. In fact, the same fate could befall Dhiraj and his adventures into online course development as a side hustle. Figure 2-4 shows a different outcome for Dhiraj’s course on Udemy.

      Dhiraj still spends 200 hours of his time creating and publishing his course. Now, though, instead of $25,500 in income just in the first year (and with momentum on his side, probably indicating an even better second year!), he brings in only $325 for the entire year. At least as of the first year, Dhiraj earns less than $2 per hour for all the time that he put into his side hustle. Not good!

      FIGURE 2-4: An unsuccessful passive-income side hustle.

Passive-income side hustles can be big winners or big losers (or somewhere in between). Sometimes, no matter how much planning you do or how good an idea seems, something just doesn’t “click” and you wind up spending a ton of time for very little money in return. Other times, though, you could hit the jackpot and that upfront effort will really pay off as the money rolls in for months or even years to come.

      You also have financial considerations on the investment and expense side of your side hustle. Suppose you want to start an online boutique and sell leisurewear. You could line up suppliers — many of whom will have minimum order amounts — and set aside a bedroom in your home as a “warehouse” where you’ll stash all

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