yourself what will happen if your sales estimates are incorrect and you’re stuck with all that inventory that you just paid a bundle for?
Alternatively, you could find suppliers who do drop shipping, where the suppliers themselves actually pack and ship the orders and you never have to stock — and more important, preemptively purchase — the products that you hope to sell. You’ll typically make less with drop shipping than you would by fulfilling your own orders, but you also have a lot less money at risk if your side hustle comes up short of what you thought it would, sales-wise.
Your Side-Hustle Clock and Calendar
Some side hustles have fairly rigid schedules. Jack can’t just decide on the fly what days of the week or time of the day he’ll teach his community college classes next semester. Cindy’s day job limits her to weekends for her bartending gigs.
Other side hustles give you far more flexibility, at least when it comes to when you’ll record videos, or pack and ship orders for your online boutique, or spend many hours handcrafting jewelry.
Max, Mark, and Miguel all plan to create online videos that they’ll then monetize for their respective side hustles. Miguel decides to do a new bartending-related video every week. Mark, however, figures that a new small business accounting video every two weeks is enough for his intended audience and fits better with his available time to record, edit, and polish the videos before uploading and publishing them. Max, on the other hand, settles on a far more fluid schedule for his “monetizing himself” videos. Some weeks, he’ll do two or three videos, and then he may pause for a couple of weeks until he does another two or three.
You also need to be honest with yourself about how your energy level aligns with the time you’ve set aside for your side hustle. Back in the 1990s and early 2000s, I would typically have two or even three active book projects at various stages at any given point. Because I was spending most of my time traveling, I allocated every hotel night to writing — at least on paper. But you know what? Sometimes, after a really long and stressful day, I would go back to my hotel after dinner, sit down at the desk, open my laptop, and not be able to string together two coherent sentences.
Figuring Out Whether You Need Special Skills or Licensing for Your Side Hustle
You can jump headfirst into some side hustles with absolutely no prerequisites at all. Interested in starting an online boutique? Go for it! Weekend bartending? Start pouring the drinks!
For other side hustles, though, you may need special skills or even need to be licensed by some governmental agency to certify that you are, indeed, qualified to do whatever that particular side hustle calls for.
For example, Shauna and Miranda have been friends since high school. Both are interested in doing infusions and other skilled medical treatments for people in their homes — a growing business in general, and one that is perfect for a side hustle.
Shauna graduated from nursing school and not only has ten years of experience as a hospital nurse, but also has all the up-to-date licenses required by the state where she lives.
Miranda? Well, she has a business degree and has been a sales rep for one of the big pharmaceutical companies for the past ten years. Miranda may be interested in providing home health-care services as a side hustle, and she may even turn out to be skilled at giving injections and similar treatments, but she doesn’t have the formal educational background or the licensing to legally be able to provide those services. Miranda’s story may be an extreme one, but you get the idea.
Many — maybe even most — side hustles have no formal licensing requirements of any kind. Others do, though. Just because you’re interested in health care, for example, doesn’t mean that you can just start a side hustle giving home infusions or providing similar services.
Even if you’re not thinking “health-care side hustle,” you still need to be aware of any licensing requirements. Suppose you want to make and sell homemade wine. Guess what? Most states in the United States require you to have a license for anything related to the manufacture and sale of alcohol.
PAY UP!
A long time ago, I was invited to give a paid presentation in Toronto as part of my consulting side hustle. I landed at the airport and, as I was going through Customs, they asked me why I was coming to Canada. I answered honestly: I was there to give a presentation. “Are you getting paid for the speech?,” they asked. About two seconds after I answered “Yes,” they told me that I needed to purchase a work visa to be able to work in Canada. Surprise! It wasn’t a whole lot of money, and at least I was able to take care of the visa on the spot. But I should have known what to expect. I do now!
Filtering and Finalizing Your Side-Hustle Short List
Maybe you began with a relatively simple “Hey, this side-hustle stuff sounds pretty good!” But I made you run the gauntlet through one decision point after another. Trust me, though: By taking the time to methodically evaluate all the key decisions and factors covered in this chapter, you’ll be in much better shape when it comes to a side hustle that’s a good match for your interests and expertise.
Cindy and Miguel both began with “bartending” as the theme of their respective side hustles. Now, after stepping through the decision points:
Cindy is going to do weekend bartending and will advertise her services on several local marketplace websites. She doesn’t need to make any significant investments, and she can reliably figure on about $1,000 in extra income each month from four or five gigs at the most.
Miguel is going to