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Beschreibung

Get yourself paid and broaden your skillset with this everyday guide to side hustles The gig economy is growing by leaps and bounds, partly because it's easier to find a flexible work-life balance. Those of us who don't want to leave our full-time jobs, however, can still grab a piece of excitement and extra income for ourselves by starting a side hustle. Or you can bundle your own personalized set of side hustles to replace your full-time job and take full control of your professional life. Whether you're thinking about driving for Uber, developing apps, or starting an online boutique, Side Hustles For Dummies walks you through every step of the way of starting your own side gig. You'll learn about how to structure your new business and keep records, create backup plans, and steer clear of scams. You'll also: * Find out whether you need investment capital and learn what your new time commitments will be * Learn to create a business plan and patch any holes in it before you get started * Discover how to incorporate a vibrant side hustle into your already busy life * Learn how to adjust your side hustle to meet changes in your personal life and the overall business climate Side hustles are for everyone, from high school and college students to full-time professionals to retirees. If you've been looking for an excuse to pursue your latest passion, hobby, or interest--or you're just in the market for some extra income--Side Hustles For Dummies is the easy-to-read, no-nonsense guide to creating a rewarding and engaging new life.

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Veröffentlichungsjahr: 2022

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Side Hustles For Dummies®

Published by: John Wiley & Sons, Inc., 111 River Street, Hoboken, NJ 07030-5774, www.wiley.com

Copyright © 2022 by John Wiley & Sons, Inc., Hoboken, New Jersey

Published simultaneously in Canada

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Library of Congress Control Number: 2022934337

ISBN 978-1-119-87013-5 (pbk); ISBN 978-1-119-87014-2 (ebk); ISBN 978-1-119-87015-9 (ebk)

Side Hustles For Dummies®

To view this book's Cheat Sheet, simply go to www.dummies.com and search for “Side Hustles For Dummies Cheat Sheet” in the Search box.

Table of Contents

Cover

Title Page

Copyright

Introduction

About This Book

Foolish Assumptions

Icons Used in This Book

Beyond the Book

Where to Go from Here

Part 1: Getting Started with Side Hustles

Chapter 1: Joining the Side-Hustle Game

Getting Clear on What a Side Hustle Is

Knowing What You’re Looking for from a Side Hustle

Seeing the Connection between Side Hustles and the Gig Economy

Recognizing That Side Hustles Are For Everyone

Chapter 2: Surveying Your Options

Your Side-Hustle Topical Area

Running with Your Side-Hustle Idea

Taking Your Side Hustle to Market

Deciding Whether to Pursue a Side Hustle Related to Your Full-Time Job

Show Me the Side Hustle Money!

Your Side-Hustle Clock and Calendar

Figuring Out Whether You Need Special Skills or Licensing for Your Side Hustle

Filtering and Finalizing Your Side-Hustle Short List

Chapter 3: Determining Your Side-Hustle Personality

Understanding Your Personality

Personality, Meet Side Hustle

Part 2: Getting Your Side Hustle Up and Running

Chapter 4: Putting Your Plans Together

Starting with Free-form Brainstorming

Transforming Your Initial Brainstorming into Your Value Chain

Risky Business

The Best of Times, the Worst of Times

Building Your Business Plan

Chapter 5: Taking Your Side Hustle for a Test-Drive

Questions, Questions, and More Questions

Establishing Success Criteria for Your Side-Hustle Test-Drive

How Much Fun Are You Having?

Deciding How Long Your Test-Drive Should Be

Checking Out Some Side-Hustle Test-Drives

Chapter 6: Putting Your Side Hustle in High Gear

Your Side Hustle Is Cleared for Takeoff

Stick to the Plan, Stan!

Alert! Alert!

Bracing Yourself for Your First Side-Hustle Hiccups

Doing Your Three-Month Checkup

Chapter 7: Running Your Side Hustle Like a Business

Choosing Your Side-Hustle Business Structure

Your Side Hustle by Any Other Name

Technology and Your Side Hustle

Playing It Safe on the Legal Front

Chapter 8: Show Me the Money

Do’s and Don’ts for Your Side-Hustle Finances

Budgeting Basics for Side Hustles

Funding Your Side Hustle

Money Coming and Going

Chapter 9: Keeping Track for You and Everyone Else

Accessing Your Side Hustle’s Foundational and Tax Documents

Keeping Track of Everything

Digging Into Your Side Hustle’s Analytics

Taking Those Old Records Off the Shelf

Chapter 10: Pay Up: Side Hustles and Taxes

Income Taxes and Your Side Hustle: The Basics

Staying Legal and Staying Honest

Filing Your Side-Hustle Income Taxes

Calculating and Filing Estimated Income Taxes

Tracking and Reporting Payments You Made to Others

Sales Taxes and Your Side Hustle

Part 3: Mastering the Side-Hustle Game

Chapter 11: Avoiding Conflicts with Your Day Job

Trouble Ahead, Trouble Behind: Navigating Issues with Your Employer

Knowing Which Outside Activities Are Approved

Making Sure You Don’t Use Your Employer’s Resources for Your Side Hustle

Dodging Employer Tricks and Traps

Chapter 12: Spinning Off Your Current Side Hustle into a New Side Hustle

Spinning the Side-Hustle Web That’s Right for You

Putting Together Your Side-Hustle Jigsaw Puzzle

Chapter 13: Other People and Your Side Hustle

Give That Side Hustle Proposition the Once-Over

Howdy, Partner!

Joining Someone Else’s Side Hustle as a Partner

Your Side-Hustle Supply Chain

Interacting with Your Side-Hustle Customers

Divvying Up Your Side-Hustle Workload

Chapter 14: Deciding When to Change Directions or Pull the Plug

Sign, Sign, Everywhere a Side-Hustle Sign

The Biggies: Time, Money, and Fun

Roll with the Changes

Turn Off the Lights, the Party’s Over

Chapter 15: Deciding What to Do If Your Side Hustle Gets Really Successful

Is Your Side Hustle Ready For the Big Time?

Your Side-Hustle Business Plan, Take 2

Looking at Key Financial Considerations

Leaving No Going-Full-Time Stone Unturned

Part 4: The Part of Tens

Chapter 16: Ten Tips on Earning Passive Income from Your Side Hustle

Remember That “Passive” Does Not Mean “No Work Required”

Watch Out for Get-Rich-Quick Schemes

Recognize That Some Side Hustles Are Mislabeled as Passive Income

Know the Difference between Investment Ideas and Passive-Income Side Hustles

Pay Attention to Your Fans

Weather the Storm of a Failed Side Hustle

Find the Right Flavor of Passive-Income Side Hustle

Be Prepared for the Financial Ups and Downs of Passive-Income Side Hustles

Calculate Your Passive-Income Side-Hustle Life Span

Stack Your Passive-Income Side Hustles

Chapter 17: Ten Leading Gig Economy Platforms

Angi

Fiverr

FlexJobs

Freelancer

Guru

99designs

TaskRabbit

Toptal

Upwork

ZipRecruiter

Chapter 18: Ten Signs That You Need to Adjust Your Side-Hustle Strategy

You’re Not Making Any Money

You Don’t Have Enough Time

The Overall Environment Is Shifting

You Experience a Major Life Disruption

An Even Better Side Hustle Has Surfaced

A Key Supplier Can’t Deliver

You’ve Achieved Your Goals Sooner Than Planned

A Business Partner Has Let You Down

Your Early Test Phases Don’t Prove Out

You’re Not Happy

Index

About the Author

Advertisement Page

Connect with Dummies

End User License Agreement

List of Tables

Chapter 2

TABLE 2-1 Side-Hustle Topical Areas and Example Subcategories

Chapter 3

TABLE 3-1 Omya’s Side-Hustle Personality Assessment

TABLE 3-2 Jason’s Side-Hustle Personality Assessment

TABLE 3-3 Key Personality Traits Relevant to a Travel/Lifestyle Video Side Hustl...

TABLE 3-4 Matching Omya’s and Jason’s Personality Traits with Those of Their Sid...

TABLE 3-5 Breanna’s Side-Hustle Personality Assessment

TABLE 3-6 Kylie’s Side-Hustle Personality Assessment

TABLE 3-7 Key Personality Traits for an Online Craft Jewelry Side Hustle

TABLE 3-8 Matching Breanna’s and Kylie’s Personality Traits with Those of Their ...

TABLE 3-9 Carl’s Side-Hustle Personality Assessment

TABLE 3-10 Matching Carl’s Personality Traits with a Ridesharing Side Hustle

TABLE 3-11 Matching Carl’s Personality Traits with a Delivery Service Side Hustl...

Chapter 4

TABLE 4-1 Sarah’s Risks and Mitigation Strategy for Her Custom Jewelry Side Hust...

Chapter 12

TABLE 12-1 Pairing Up Synergistic Side Hustles

List of Illustrations

Chapter 2

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

FIGURE 2-2: A typical MLM hierarchical structure.

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

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

Chapter 4

FIGURE 4-1: Using an organization diagram to document your value chain.

FIGURE 4-2: Sarah’s organization diagram for her side-hustle value chain.

FIGURE 4-3: Sandy’s organization diagram for his side hustle.

FIGURE 4-4: Cindy’s organization diagram for her side hustle.

Chapter 9

FIGURE 9-1: Creating a comprehensive set of analytics across multiple side hust...

Chapter 10

FIGURE 10-1: Use a Schedule C to file your side-hustle taxes for a sole proprie...

FIGURE 10-2: Use Form 1120-S to file your side-hustle taxes for an S corporatio...

FIGURE 10-3: Use a Schedule K-1 to link your side hustle business tax return wi...

FIGURE 10-4: Transfer your side-hustle income information from your Schedule K-...

FIGURE 10-5: Use Form 1065 to file your taxes if you organized as a partnership...

FIGURE 10-6: File Form 1096 to help the IRS keep track of who your side hustle ...

FIGURE 10-7: File Form 1099-NEC to tell the IRS who you paid money to for your ...

FIGURE 10-8: Form W-9 is where you their share tax identification numbers and d...

Chapter 14

FIGURE 14-1: The internal and external components of your side hustle’s value c...

Chapter 15

FIGURE 15-1: Revisiting your side-hustle value chain.

FIGURE 15-2: Miguel’s side hustle: part-time with his day job versus going full...

FIGURE 15-3: Miguel’s full-time side hustle with only half the revenue.

Guide

Cover

Title Page

Copyright

Table of Contents

Begin Reading

Index

About the Author

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Introduction

When you entered the work world, you might have thought you’d do that job — and only that job — until you left that company one day. Until then, your day job (or your night job, if you work evenings) would be your only job.

Not so fast. Tens of millions of people in the United States, and hundreds of millions of people around the world, supplement their primary jobs with some type of business activities on the side. These people all spend at least some of their professional lives embracing the idea of side hustles.

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.

About This Book

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.

Foolish Assumptions

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.

Icons Used in This Book

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.

Beyond the Book

In addition to what you’re reading right now, this product also comes with a free access-anywhere Cheat Sheet. There you can find reasons to start a side hustle, categories of side hustles, and ways to avoid conflicts between your side hustle and your day job. To get this helpful content, simply go to www.dummies.com and type Side Hustles For Dummies Cheat Sheet in the Search box.

Where to Go from Here

Now it’s time to dive into the world of side hustles! If you’re totally new to the subject, you won’t want to skip the chapters in Part 1, because they provide the foundation for the rest of the book. If you already have a side hustle underway, I still recommend that you at least skim Part 1 to get a sense of how to get beyond all the hype, buzzwords, and generalities related to side hustles.

From there, you can read the book sequentially from front to back, or jump around as needed, using the table of contents and index as your guide. Whatever works best for you is how you should proceed.

Part 1

Getting Started with Side Hustles

IN THIS PART …

Get the straight scoop about the world of side hustles.

Figure out if you’re ready to jump into a side hustle.

Find the perfect hustle to match your mindset and your lifestyle.

Chapter 1

Joining the Side-Hustle Game

IN THIS CHAPTER

Defining a side hustle

Matching side hustles with your own aspirations

Linking side hustles and the gig economy

Looking at side hustles for all ages and life situations

If you’re thinking about jumping into a side hustle — or if you’ve already taken the plunge — you’re not alone! According to a study reported on Side Hustle Nation (www.sidehustlenation.com/side-hustle-statistics), 45 percent of working Americans — around 70 million people! — had at least one side hustle going. Even better: Another 60 million were thinking about jumping into the side-hustle game.

Side hustles aren’t only popular in the United States either. According to an article paid for by GoDaddy appearing on the USA Today website (www.usatoday.com/story/sponsor-story/godaddy/2017/12/12/how-people-side-hustling-around-globe/108532604), 54 percent of people in the United Kingdom, another 54 percent of people in Singapore, and an astounding 77 percent of people in the Philippines had side hustles.

Side hustles are all the rage, all around the world. But what exactly is a side hustle?

Getting Clear on What a Side Hustle Is

If you were to put ten people in a room and ask them to define the term side hustle, you would probably get 15 different answers. Instead of having some precise, everyone-is-in-agreement definition for the term, we have a lot of shades of gray and wiggle room in defining what is — and what isn’t — a side hustle.

Some people think that a side hustle is limited to activity in the so-called gig economy (see “Seeing the Connection between Side Hustles and the Gig Economy,” later in this chapter), filling a services industry type of role on a contract basis, with self-set flexible hours — for example, shuttling passengers in your own car for Lyft or Uber, delivering packages in your spare time for Amazon, shopping and delivering groceries for Instacart, or delivering restaurant meals for DoorDash or Grubhub.

Some people limit the world of side hustles to part-time roles in businesses that operate under the multi-level marketing (MLM) structure. Anything else is, well, something else, but not necessarily a side hustle. (See Chapter 3 for a discussion of MLMs.)

Other people think of a side hustle as being limited to anything where you’re compensated on a non-employee basis rather than as a salaried employee. In the United States, that means you file a W-9 form and have your income reported on a 1099 form, rather than being paid a salary (even a part-time salary) on a W-2 basis. To their way of thinking, if you’re paid as part of someone else’s payroll and receive a W-2 at the end of the year, then whatever you’re doing isn’t a side hustle. (See Chapter 8 for a discussion of the various business structures for your side hustle.)

Which of these perspectives is correct? Well, a better question to ask is this: Are any of these perspectives too narrow? The answer: Yes, they are all too narrow — not necessarily wrong, just too limiting in attempting to define what is and isn’t a side hustle.

A better way to look at a side hustle is to consider an activity to be a side hustle if it’s one in which you’re materially invested (basically, what you’ve started isn’t some passing whim, but rather something you’re really, really interested in doing) but it’s not your full-time, salaried, career-oriented job. Basically, a side hustle is an activity that is “on the side” of your primary, full-time job and that requires more than a minimal amount of time and energy (at least as you get established).

Now consider a few examples:

Meghan is a financial analyst for a Denver-based insurance company. She lives in the south suburbs of the Denver metro area but works downtown. Three or four times a week, if she doesn’t need to be back home after work by a certain time, Meghan signs in to an app and becomes an Uber driver, earning a little bit of extra money during her evening commute. Sure, she and her car don’t exactly take the most direct route back from downtown to the south suburbs, but a song from way back in the late 1970s by the rock group Supertramp perfect describes Meghan’s journey on those Uber-enabled evening drives: She takes the long way home!

Jack is a software developer for an app development company based in Scottsdale, Arizona. Jack’s employer supports both flexible hours and working from home. As long as Jack and his coworkers meet their deadlines for assigned work, they have a great deal of autonomy for how they manage their time. Taking advantage of his employer’s flexibility, Jack teaches a programming class two afternoons each week at a community college campus about 5 miles from his apartment.

Bhavna graduated with top honors from a leading engineering school and works as a mechanical engineer at an aerospace company in Seattle. She’s very good at her job, but after a couple of years, Bhavna is becoming disenchanted with the aerospace industry and even her chosen engineering profession! If she had a time machine, Bhavna would go back to her college days and study what she belatedly discovered she’s really interested in: the world of fashion and retail. No worries, though: Last year, Bhavna started a small online boutique, selling clothing and accessories. She spends a couple evenings a week, not to mention most of her weekends, on a range of tasks for her boutique: finding and buying new products, packing and shipping orders, and doing all sorts of general business management functions. Soon — maybe

very

soon — Bhavna plans to ditch her full-time job and devote all her energies to her boutique.

Eric and Brittany had been single-mindedly focused on their respective full-time careers, both before they met as well as after they began dating and eventually got married. Eric is a high school teacher, while Brittany is a drug sales rep for a large pharmaceutical company. When the COVID-19 pandemic hit in early 2020, however, both of their professional worlds turned upside down. Eric continued teaching but solely online because his high school switched over to all-online courses. Brittany’s job was eliminated as part of the pharmaceutical company’s cutbacks, and she began working 15 to 20 hours a week shopping and delivering groceries for Instacart. As the months went by, Brittany also began delivering meals for both Grubhub and Uber Eats, as well as occasionally driving for Lyft. Eric began doing college entrance exam tutoring on the side, in addition to his full-time teaching. Eric is now wondering if he should quit his full-time teaching job and not only do even more SAT and ACT tutoring, but maybe even do some Lyft or Uber driving.

Pop quiz time!

From the blurbs above, who is in the side-hustle game? Meghan and her Uber driving? Jack and his community college teaching? Bhavna and her online boutique? Brittany and her portfolio of gig-economy jobs? Eric and his college entrance exam tutoring?

If you answered “all of the above,” you’re absolutely correct. Even though the particulars for what Meghan, Jack, Bhavna, Eric, and Brittany are doing vary at least a little bit from one person to the next, each one of them has already jumped onto the side-hustle bandwagon.

Some side hustles are actually part-time jobs rather than a small business or some gig-economy side work. In fact, you get paid for your side hustle through a regular paycheck — just like most day jobs — rather than in the less-than-predictable manner of most side businesses.

Take Jack, the Scottsdale software developer. Jack doesn’t have a side business 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 that is similar to what you do for your day job, but different enough to scratch that side-hustle itch. I should know — that’s exactly how I jumped into the side-hustle game many years ago.

Many years ago, in the early days of my professional career, I was a U.S. Air Force computer systems officer. I was stationed at Cheyenne Mountain in Colorado Springs, Colorado, and was assigned to an office of about ten other officers and civilians who were responsible for writing software for the missile warning defense of the United States. Basically, our software received messages from sensor sites all around the world that detected missile launches and then used some head-spinning math to figure out if this alert was just a test launch by “the other side” or if (cue the ominous music) they had just started World War III.

A pretty cool-sounding job, right? This was in the early and mid-’80s, at the height of the Cold War, and you could say that business was good for the missile launch detection mission and expanding the functionality of our software to support new and upgraded sensor sites. Only one problem: Our software was written in an ancient programming language called JOVIAL that was already obsolete and was only used in certain military-oriented applications and systems. Well, make that two problems: Our JOVIAL-written software ran on antiquated UNIVAC mainframe computers from the ’60s and ’70s. (In fact, our UNIVAC was so out of date that the university where I went to school — Arizona State — had retired its UNIVAC two years earlier because it had become too obsolete for academia!)

The early and mid-’80s were also when so-called “microcomputers” — what we know as personal computers today — were hitting the market and quickly becoming wildly popular, not only for home use but also in business. Wouldn’t it be great to get some experience in this hot new area of computer technology, even if the hardware and software of my full-time job was light-years behind what was coming to market? I was almost certain that I wasn’t going to stay in the Air Force past the four years that I owed in exchange for my college scholarship, and when I reentered the civilian world, I would be four years behind so many other people in the tech field.

I bought my first personal computer and started a little application development and computer training side business, aimed at small businesses and not-for-profits in Colorado Springs and in Arizona, where I had gone to college and lived before going on active duty. And of course, I crammed and crammed and crammed, learning as much as I could about these new-fangled microcomputers and then-modern PC programming languages and software development frameworks.

Soon enough, I landed my first consulting project at a local tourism-oriented business. That first project was a doozy! I learned the hard way how packaged software development frameworks didn’t always work as advertised and were often full of bugs (as we refer to software problems in the programming trade). I had to program a lot of workarounds into the customer’s system to prevent the applications from blowing up, or to help them get back up and running if their application suddenly and abruptly terminated. I think I sized and priced the job at about 150 hours and wound up putting an extra 30 or 40 hours into the project that I didn’t bill for to handle all the complications.

But I learned a ton! And I learned even more on the next customer’s project, and the next one after that. Fast-forward to when I got ready to leave the Air Force and started looking for a job. Everything I learned during four years of doing software projects (and also some computer training) on the side — in other words, my first side hustle — really helped me get the perfect job and jump-start my civilian tech career.

Was I trying to make some extra money above and beyond my Air Force salary? Of course! Back in those days, junior officers didn’t make a whole lot of money. So, I was absolutely after money!

But even more than the additional income, my primary motivation was the knowledge and experience that I gained from my side-hustle consulting and software business. Could I have just bought a PC and taught myself modern programming skills and microcomputer administration without starting a side hustle? Sure. But my thinking at the time was — and still is, even with 40 years of hindsight — that if I didn’t force myself to spend all those hours behind a keyboard because I owed finished applications to my clients, I might not have had the motivation to do more than a perfunctory amount of self-learning. And I almost certainly wouldn’t have run into all the unforeseen software hiccups for which I had to find workarounds, which served me well even in my full-time Air Force job, not to mention when I became a software product developer after leaving the Air Force.

You can do the same thing that I did so many years ago, no matter what your full-time job is or what industry you currently work in: Start a side hustle to learn new skills, and make some money at the same time for your efforts!

Jumping onto a different career track

Maybe you’ve been in your career field for 10 or even 20 years, but you’re at the point where going to work every day is starting to be harder and harder. True, you’re making decent money. But the days drag, and you can’t wait until the workday is over.

Or maybe you wound up with the job of your dreams, but those dreams turned out to be more of a fantasy. Sure, you knew about the crushing hours and the wearying travel, but you were actually looking forward to the fast-track lifestyle on the road toward that big-time paycheck. Now, after only a year or two, you’re asking yourself, “What in the world was I thinking?”

You’re not quite ready to hit the ejection seat without a new job. You could start interviewing for jobs with a better work–life balance. But one message that has come through loud and clear every time your boss tells you that you need to work all weekend and miss a family event: You really want to be your own boss.

A side hustle can be the perfect gateway between your current career path and something — anything — that is totally different. Not sure exactly where your passions lie? Try out one side hustle that fits your available time and passions. If it works, great: You can work on taking that particular side hustle to the next level and turning it into a full-time business (see Chapter 15). If that one doesn’t do it for you, no problem — try another one, all the while still trudging along at your full-time job.

Or, if something miraculously happens for the better in the realm of your full-time job — say, you wind up interviewing with and then accepting a new job in your current career with better hours and a much lower stress level — you can either keep your side hustle going or slowly unwind and stop doing your side gig (see Chapter 14).

Profiting from a hobby or passion

Whether it’s sports memorabilia, Pokémon cards, stamp and coin collecting, scrapbooking and crafting, gardening, homebrewing, or winemaking — or any one of dozens of other hobbies — there’s probably an opportunity for you to monetize your hobby by adding on some sort of side hustle.

Todd started collecting baseball and other sports cards when he was a kid and collected them all through high school. When he went away to college, he tossed all his cards — carefully, of course! — into the closet of his old room at his parents’ house. Fortunately, Todd’s mother didn’t throw out all his sports cards when he moved away, as many of Todd’s friends’ mothers did. Almost 20 years later, Todd rediscovered his old cards during a Thanksgiving visit to his parents’ house.

What did Todd do next? Sure, he began buying current cards for his personal collection at the local big-box retailers and also at hobby shops. But he also discovered something interesting: Some of his childhood cards were now worth a fair bit of money! He began reading blogs and listening to podcasts about the investment and speculation side of sports cards. He began bargain-hunting on social media, at swap meets and flea markets and estate sales, and anywhere that he might find cards for sale. If he found a good bargain, he would buy cards — sometimes lots of cards — with the intention of flipping them for a modest profit.

Then Todd had another idea. Sure, there were already lots of podcasts and YouTube channels about sports card collecting and investing. But he had some interesting and unique ideas about topics that he didn’t see covered anywhere else. By the time baseball season was underway, Todd’s YouTube channel was up and running. Several months later, Todd had more than 1,500 subscribers. At that point, he applied for YouTube’s Partner Program so he could begin monetizing his YouTube presence. (Just in case you’re not familiar with the term monetizing, it means “to make money from” and it’s a key element to many side hustles.)

Fast-forward six months to October and World Series time. Each of Todd’s videos was now generating a large number of views, and he was pulling in a couple thousand dollars a month from ad placement revenue.

Todd had taken his newly rediscovered passion — sports card collecting — and turned it into not one, but two side hustles: sports card investing and flipping, and also monetized videos about the hobby he had rejoined after being away for 20 years.

Playing defense

The signals are crystal clear: Your job is in jeopardy!

Maybe the overall national economy hasn’t been that great for the past six months and seems to be slipping into recession. Or maybe the economy is just fine, but your employer made a couple of serious missteps and profits are way, way down — and rumors of layoffs are swirling through the office.

Whatever the reason, you can read the writing on the wall: Losing your job may be in your near-term future — and even though you’ve been a top-notch performer, there’s nothing you can do about it.

Or is there?

A side hustle can help you “play defense” and cushion the blow of being laid off, should that unfortunate turn of events actually come to pass. If you’re already doing something on the side, great! You can ratchet up your efforts and try to earn even more money from your side hustle than you already are. Driving 10 or 15 hours a week for Uber? Ramp that up to 20 or 25 hours, if you can make the schedule work with your full-time job. And then if you wind up getting laid off, you can immediately start driving 40 or 50 hours a week to help make up for the loss of your full-time salary.

Or maybe you’ve already maxed out the number of hours or level of effort you can put into your current side hustle, but you can add another side hustle if your schedule has — unfortunately — been “freed up.”

If you were fortunate enough to receive a severance package when you lost your job, and if you’re also receiving unemployment insurance payments, great! But don’t procrastinate with your side hustles! Sure, you may need to take a week or two to process your job loss, but get back on that proverbial side-hustle horse as soon as possible!

At the first inkling of a possible job loss, if you don’t already have a side hustle underway, take a long, hard look at some ideas that you think you could make work. Because the last thing you want is to not only lose your job, but to be totally powerless when it comes to your own financial fate.

Activating your financial emergency response plan

The worst has happened: You’ve lost your job, for one reason or another. Even more than that: You now find the traditional world of full-time employment so distasteful that you cringe every time you think about heading out on the interview trail. Even the thought of receiving and accepting a job offer, rejoining the same grind that you just left, makes you queasy. Maybe this isn’t the first time you lost your job, and in your mind, you’re about to jump right back onto the same treadmill that inevitably ends with your being whooshed off the back, tumbling onto the floor. If so, a side hustle may be just the ticket: a way to earn money while being your own boss.

Seeing the Connection between Side Hustles and the Gig Economy

According to Investopedia (www.investopedia.com/terms/g/gig-economy.asp), the term gig economy refers to an economic climate where “temporary, flexible jobs are commonplace and companies tend to hire independent contractors and freelancers instead of full-time employees.” (Investopedia also goes so far as to claim that “a gig economy undermines the traditional economy of full-time workers who often focus on their career development.”)

What’s relevant in this definition for understanding the concept of side hustles is the reference to “independent contractors and freelancers.” When Meghan takes the long way home from downtown Denver because she goes on the clock with Uber, she’s functioning as an independent contractor rather than as an employee of Uber. If you take a step back and look at the big picture of the ride-sharing business, one of the points of contention is that Lyft, Uber, and other ride-sharing companies use independent contractors to compete with taxi companies, limousine services, and airport shuttles.

From Meghan’s sort-of-microeconomic point of view, she has a little side hustle going a couple times a week to earn a little extra money. From the big-picture, macroeconomic view, however, Meghan’s side hustle “enables” the gig-economy concept and has helped disrupt longstanding business models.

THE “GREAT RESIGNATION” AND SIDE HUSTLES

A somewhat surprising byproduct of the COVID-19 pandemic and its disruption of global business has been the so-called “Great Resignation” of 2020 and 2021.

The early stages of the pandemic, in spring and early summer of 2020, saw massive job loss in the United States and around the world. U.S. unemployment peaked at 13 percent in May 2020 and may actually have been a point or two higher than what was officially reported (www.pewresearch.org/fact-tank/2020/06/11/unemployment-rose-higher-in-three-months-of-covid-19-than-it-did-in-two-years-of-the-great-recession) before beginning to drop back to more “normal” levels in the latter part of 2020 and into 2021.

Normally, high unemployment levels lead to workers exhibiting three perfectly natural behaviors:

Those who are lucky enough to avoid being laid off often cling to the security of their current jobs for dear life, doing everything they can to avoid joining the ranks of the unemployed.When an economic recovery arrives and picks up steam, many people continue to cling to their jobs. Maybe they do so out of gratitude for being able to keep their jobs, or perhaps they saw the financial and personal toll on others who weren’t as fortunate and did lose their jobs.Many of those who do find themselves unemployed — temporarily, they hope — do everything they can to find new jobs and then likewise cling to those jobs and do everything in their power not to again lose that job security.

But 2020 was different. Maybe the extreme safety net measures taken by governments all around the world made this severe downturn different from previous ones. In the United States, for example, state-level unemployment payments were boosted by additional federal government money that came through the Pandemic Unemployment Assistance (PUA) program. The bottom line was that for many people, unemployment during the early stages of the COVID-19 pandemic wasn’t as disruptive and painful on a personal or family basis as it might otherwise have been.

With some of the lost-my-job pressure reduced, many of those newly unemployed workers started dabbling in a little bit of this or a little bit of that during their now-free time. Others who kept their jobs were working at home with far greater schedule flexibility than they had ever had before. Many people enjoyed another side benefit of working from home: saving one, two, three, four — or maybe even more! — hours a day by not having to commute to and from an office. And what did many of those folks do with their now-free time? They also dabbled in a little bit of this or a little bit of that.

Stated another way: Lots of people picked up the side-hustle habit during the spring and summer of 2020.

By the autumn of 2020, COVID infection rates were dropping along with the unemployment rate. Largely due to the extraordinary measures taken by governments around the world, the business world didn’t collapse during the worst of the pandemic. Now, recovery was on the horizon, and many companies began refilling the positions they had terminated earlier in the year.

But tens of millions of people in the United States, and tens of millions more around the world, had a taste of the world of side hustles and were now rethinking the very idea of rejoining the full-time workforce.

Even more people eyeballed side hustles from the security and stability of their careers and decided to ditch full-time work in favor of a portfolio of side hustles. An October 2021 study by leading consultancy McKinsey noted that 19 million workers had quit their full-time jobs since April of that year (www.mckinsey.com/business-functions/people-and-organizational-performance/our-insights/great-attrition-or-great-attraction-the-choice-is-yours)! Where would a person head after quitting a full-time job? For many, the answer is crystal clear: the world of side hustles!

Jobs with lower wages and even lower satisfaction levels — not to mention traditionally high turnover — have been particularly hard hit by the Great Resignation. Many of these jobs were in the service industry: restaurants, retailers, cleaning- and repair-oriented businesses, and others. But surprisingly, according to a September 2021 Harvard Business Review article (https://hbr.org/2021/09/who-is-driving-the-great-resignation), “resignation rates are highest among mid-career employees.” Maybe even more surprising: “resignations are highest in the tech and health care industries.”

And so, the Great Resignation got underway during a climate when most experts would have expected otherwise. People still needed to make money somehow, though, which is a large part of the reason that so many people jumped onto the side-hustle bandwagon for the first time beginning in 2020.

Suppose, however, that Lyft, Uber, Instacart, DoorDash, Grubhub, and other similarly structured companies didn’t have a large pool of independent contractors to drive, deliver groceries or meals, or perform other services. Say these companies had to hire full-time employees. Basically, their business models would fall apart. The primary utility they provide is brokering between those who are available to provide certain services and those who want to take advantage of those services.

But the nature of those services is unpredictable and subject to peaks and valleys. Many of these services are also very short-term in nature — maybe a 45-minute drive to the airport or an hour’s worth of grocery shopping and delivery. Large portions of the so-called gig economy are built around short-duration “service matchmaking” between an ever-changing pool of providers and those who need those services, at least at the moment.

Even longer-duration services fall under the gig economy. Going on a two-week summer vacation, but not taking the two family dogs? No problem: Use Rover or another pet-sitting service, and you can find someone to stay at your house and take care of Fido and Spot for the two weeks. After your vacation is over, you head back home and your pet sitter heads off to a new gig — or, you could just as accurately say, to a new client for their pet-sitting side hustle.

The key point is that side hustles and the gig economy are made for each other. In the United States and in much of the world, traditional employment and career notions are being turned on their heads. Companies are foregoing the idea of hiring full-time or even regular part-time employees in lieu of independent contractors who can come and go with little or no disruption to business operations. And many people are turning their backs on full-time jobs and careers in favor of less secure but more flexible, shorter-duration independent contractor assignments.

Recognizing That Side Hustles Are For Everyone