Alan R. Simon - Side Hustles For Dummies

I should know, because I’m one of them. My entire professional life has been filled with side hustles.

In 1982, I was a U.S. Air Force computer systems officer, writing software on an antiquated 1960s-era UNIVAC mainframe using an even more ancient 1950s programming language. “Microcomputers” (PCs) were just coming on the market and were all the rage, and I was concerned that by the time my Air Force commitment was up in the mid-1980s, I would be way behind the curve when it came to the newer technology of the day.

I started a computer consulting business on the side, writing PC-based applications for small businesses and not-for-profits in Colorado and Arizona. That side hustle spawned another one when I wrote my first book for McGraw-Hill, How to Be a Successful Computer Consultant, which described how to create and operate what we would refer to today as a side-hustle consultancy. That first book led to a revised edition a couple of years later, followed by 30 more technology and business books over the years.

Eventually, my consulting business and those writing projects spawned other side hustles, including university teaching, video courses for Lynda.com (now LinkedIn Learning) and Udemy, and writing novels.

And I’m not the only person in my family who has embraced the idea of side hustles. My wife started an online boutique while she was doing business consulting, and that online boutique led to her latest side hustle: building and maintaining Shopify sites for other small businesses. My parents had a side-hustle mail-order business back in the 1970s, in addition to my dad’s full-time job. My father and uncles owned a chain of retail record and video stores in Tucson from the 1970s to the mid-1990s, but one of my uncles started a side business for used records, which, in turn, spawned yet another side hustle selling used CDs. Finally, a century ago, one of my great-grandfathers was sort of a pioneer in the world of side hustles: His day job was owning and running his family produce store, but on the side, he was a bootlegger, making and selling illegal alcohol during Prohibition!

In some ways, a side hustle is like any other job, or running any other small or medium business. But the very nature of side hustles — the fact that you’re doing something alongside a full-time job, or perhaps alongside other side hustles that you’ve got going — presents unique challenges, as well as unique opportunities, above and beyond a “regular” job or self-owned business. Understanding those challenges, and taking advantage of those opportunities, can be daunting as you jump into the side-hustle game.

That’s where Side Hustles For Dummies comes in.

Side Hustles For Dummies helps you make sense of the ABCs — acronym anarchy, buzzword bingo, and complicating confusion — that you frequently find in short articles, blog posts, and online videos about side hustles.

This book is not just a tutorial about side hustles; it also serves as a reference that you may find yourself consulting on a regular basis. You don’t need to memorize large blocks of content (there’s no final exam!) because you can always go back to take a second or third or fourth look at any particular point during your own side-hustle adventures.

Right from the start, you find out what you should expect from the world of side hustles, as well as see what challenges are lurking. You dig deep into deciding what kind of side hustle will work best for your individual and family situation — or if one even does! — and then wrap your brain around the big picture of how the operational, financial, and legal sides of your side hustle all fit together.

I don’t use many special conventions in this book, but you should be aware that sidebars (the gray boxes you see throughout the book) and anything marked with the Technical Stuff icon are skippable. So, if you’re short on time, you can pass over these pieces without losing anything essential. On the other hand, if you have the time, you’re sure to find fascinating information here!

Within this book, you may note that some web addresses break across two lines of text. If you’re reading this book in print and want to visit one of these web pages, simply key in the web address exactly as it’s noted in the text, pretending as though the line break doesn’t exist. If you’re reading this as an e-book, you’ve got it easy: Just click the web address to be taken directly to the web page.

The most important assumption I’ve made about you is that you either are seriously exploring the world of side hustles or already have a side hustle going and are looking for additional insights to help you make the most of your efforts.

Perhaps you’re driving for Lyft or Uber, or delivering packages for Amazon, or delivering food for Grubhub or DoorDash, in addition to your full-time job. Or maybe the professional side of your life thus far has been limited to a full-time job, but you’re getting the itch to do something on the side.

Maybe your satisfaction level with your day job has been on the decline in recent years, and you’re thinking about switching careers, but you want to get a better idea of what you’re getting into. A side hustle could be the perfect way for you to have your cake and eat it, too: Keep your full-time job and financial security for the time being, while seeing if the grass really is greener doing something else.

Or you could already have a side hustle underway that’s going so well that you’re thinking about expanding your business. Not quite sure how to take your side hustle to the next level? This book has the answers.

You don’t need to already be in the side-hustle game for Side Hustles For Dummies to be helpful. No prior business knowledge or experience is assumed, nor do you have to already be laser-focused on one particular side-hustle idea. You’ll find all sorts of ideas and plans in these pages to either get you started or keep your side hustle moving along.

As you read this book, you’ll find icons in the margins that indicate material of particular interest. Here’s what the icons mean:

These are the tricks of the side-hustle trade. You can save yourself a great deal of time, and avoid more than a few false starts, by following specific tips collected from the best practices (and learned from painful experiences) of those who preceded you in the world of side hustles.

Side hustles are often filled with detours and roadblocks. Pay particular attention to situations that are called out with this icon.

Occasionally, I take a deep dive into a particular topic related to side hustles, and these sections are identified with this icon. If you’re not particularly interested in the nitty-gritty details, you can skim or even skip over these sections.

Some points about side hustles are so critically important that you’ll be well served by committing them to memory. You’ll even see some of these points repeated later in the book because they tie in with other material. This icon calls out this crucial content.