Alan Simon began his first side hustle in 1982, doing consulting for small businesses and not-for-profits. He's been juggling a variety of side gigs ever since. Alan has been writing novels for 20 years and is currently the managing principal of Thinking Helmet, Inc., a boutique consulting firm.

Introduction 1

About This Book 2

Foolish Assumptions 3

Icons Used in This Book 3

Beyond the Book 4

Where to Go from Here 4

Part 1: Getting Started With Side Hustles 5

Chapter 1: Joining the Side-Hustle Game 7

Getting Clear on What a Side Hustle Is 8

Knowing What You’re Looking for from a Side Hustle 12

Money, money, money money! 12

Extending your knowledge and gaining experience 13

Jumping onto a different career track 15

Profiting from a hobby or passion 16

Playing defense 17

Activating your financial emergency response plan 18

Seeing the Connection between Side Hustles and the Gig Economy 18

Recognizing That Side Hustles Are For Everyone 21

Chapter 2: Surveying Your Options 23

Your Side-Hustle Topical Area 24

Running with Your Side-Hustle Idea 28

Contracting to perform a service 28

Selling products (and maybe making products as well) 29

Providing information 30

Monetizing yourself 32

Monetizing an asset for your side hustle 33

The part-time job side hustle 33

Drilling into your side-hustle topical area 35

Taking Your Side Hustle to Market 38

Going to market on your own 38

Leveraging an online marketplace 39

Multilevel marketing organizations 40

Deciding Whether to Pursue a Side Hustle Related to Your Full-Time Job 42

Show Me the Side Hustle Money! 43

Your Side-Hustle Clock and Calendar 47

Figuring Out Whether You Need Special Skills or Licensing for Your Side Hustle 48

Filtering and Finalizing Your Side-Hustle Short List 49

Chapter 3: Determining Your Side-Hustle Personality 51

Understanding Your Personality 51

Extrovert or introvert? 52

How many balls can you juggle? 53

Can you give yourself that kick in the pants to get going? 53

Working past the point of wanting to stop 54

Painting your side-hustle picture 55

Collaborating (or not) 56

You hurt my feelings! 57

This fight isn’t over! 58

Shaking off failure 59

Sorry, not interested anymore! 60

The picture or the thousand words? 61

Personality, Meet Side Hustle 62

Creating and monetizing travel-related lifestyle videos 62

Making and selling craft jewelry 66

Finding the right gig in the gig economy 69

Part 2: Getting Your Side Hustle Up and Running 73

Chapter 4: Putting Your Plans Together 75

Starting with Free-form Brainstorming 76

Whatcha gonna do? 76

Who’s there? 77

Location, location, location! 77

Drafting your timeline 78

How now, brown side-hustle cow 78

Okay, but why? 79

Doing the brainstorming two-step 80

Transforming Your Initial Brainstorming into Your Value Chain 81

Risky Business 86

The Best of Times, the Worst of Times 87

Building Your Business Plan 89

A short overview and a really short elevator pitch 90

Your time commitment 91

Your schedule and major milestones 91

Key players in your side hustle 92

Your customers 92

Startup money, budget, and financial projections 93

How you’ll operate 93

Risks and mitigation 93

Chapter 5: Taking Your Side Hustle for a Test-Drive 95

Questions, Questions, and More Questions 96

Establishing Success Criteria for Your Side-Hustle Test-Drive 97

How Much Fun Are You Having? 98

Deciding How Long Your Test-Drive Should Be 99

Checking Out Some Side-Hustle Test-Drives 100

Creating videos to monetize online content 100

Making and selling your own products 104

Doing delivery services 107

Chapter 6: Putting Your Side Hustle in High Gear 111

Your Side Hustle Is Cleared for Takeoff 111

Doing your preflight check 112

Marking the date 113

Telling the world! 114

Stick to the Plan, Stan! 115

Alert! Alert! 115

Paying attention to your technology 116

Having your backup supply chain on standby 117

Making sure you don’t get blindsided by social media 117

Bracing Yourself for Your First Side-Hustle Hiccups 118

Doing Your Three-Month Checkup 120

Chapter 7: Running Your Side Hustle Like a Business 123

Choosing Your Side-Hustle Business Structure 123

Sole proprietorship: The path of least resistance 124

Partnership: Not going it alone 126

Limited liability company: Playing it safe 127

S corporation: Straddling the corporate world 129

Your Side Hustle by Any Other Name 130

Technology and Your Side Hustle 131

Your technology behind the curtain 132

Your side-hustle website 132

Your storefront 134

Social media 134

Playing It Safe on the Legal Front 135

Welcome to the side-hustle zone 136

Running a side hustle out of your home 137

Considering the rules of your apartment complex 138

License and side-hustle registration, please 138

Chapter 8: Show Me the Money 141

Do’s and Don’ts for Your Side-Hustle Finances 142

Budgeting Basics for Side Hustles 143

Forecasting your revenue 144

Separating your gross revenue from your net revenue for budgeting purposes 150

Planning your expenses 151

Funding Your Side Hustle 156

Using your own money 157

Borrowing money for your side hustle 158

Bringing in outside investors 159

Money Coming and Going 161

Collecting payments 161

Paying your bills 162

Chapter 9: Keeping Track for You and Everyone Else 163

Accessing Your Side Hustle’s Foundational and Tax Documents 164

Quickly pulling information from documents 165

Have another helping of documents 165

Keeping Track of Everything 166

Your official side-hustle records 166

Your backup and catchup plan 168

Side-hustle record-keeping tools and tech 169

Digging Into Your Side Hustle’s Analytics 170

Taking Those Old Records Off the Shelf 173

How long should you keep your side hustle records? 174

Record-keeping for your real-estate side hustle 175

Chapter 10: Pay Up: Side Hustles and Taxes 179

Income Taxes and Your Side Hustle: The Basics 180

Filing requirements based on your side hustle’s legal organization 180

Tax rules and forms depending on your specific side hustle 181

Everyone wants a piece of the tax action 181

Decision time 182

Staying Legal and Staying Honest 183

Business deductions for your side hustle 183

Taking your side hustle across state lines 184

Now for your next side-hustle tax trick 185

Uh-oh — you goofed! 187

Filing Your Side-Hustle Income Taxes 187

Keeping the feds happy 188

Your state wants their cut, too 192

Keeping your tax money local 193

Calculating and Filing Estimated Income Taxes 193

Tracking and Reporting Payments You Made to Others 194

Sales Taxes and Your Side Hustle 197

Part 3: Mastering the Side-Hustle Game 199

Chapter 11: Avoiding Conflicts with Your Day Job 201

Trouble Ahead, Trouble Behind: Navigating Issues with Your Employer 202

Noncompete clauses 203

Conflicts of interest 204

Conflicts of commitment 205

Knowing Which Outside Activities Are Approved 211

Making Sure You Don’t Use Your Employer’s Resources for Your Side Hustle 213

Computers 213

Company Wi-Fi networks 214

Audio/video resources 216

Company time 218

Company premises 218

Dodging Employer Tricks and Traps 219

Side-hustle awareness begins even before you start a job 220

They’re coming after you! 224

A little paranoia never hurt anyone 226

The employer strikes back 226

Chapter 12: Spinning Off Your Current Side Hustle into a New Side Hustle 229

Spinning the Side-Hustle Web That’s Right for You 230

All aboard the synergy train 230

Building a balanced side-hustle portfolio 231

Passing the side-hustle baton 232

Putting Together Your Side-Hustle Jigsaw Puzzle 234

Making sure you have enough time available 234

Checking for conflicts 236

Balancing your side-hustle checkbook 237

Chapter 13: Other People and Your Side Hustle 239

Give That Side Hustle Proposition the Once-Over 240

Gathering your team of advisers 242

Deciding what to share and with whom 244

Howdy, Partner! 246

What does a potential partner offer? 246

How do the two of you get along? 247

How does a potential partner get along with other stakeholders? 247

What are this person’s weaknesses? 248

What other alternatives do you have? 250

How will the financial picture of your side hustle change? 250

How will the voting and ownership of your side hustle change? 250

Joining Someone Else’s Side Hustle as a Partner 251

Why are they asking you? 252

What do you offer? 252

How will the compensation and ownership be set up? 252

Can you be kicked out? 253

Can you wind up on the hook financially? 254

Your Side-Hustle Supply Chain 255

Interacting with Your Side-Hustle Customers 256

Divvying Up Your Side-Hustle Workload 257

Chapter 14: Deciding When to Change Directions or Pull the Plug 259

Sign, Sign, Everywhere a Side-Hustle Sign 260

Changes in your customers and markets 260

Supply-chain changes 262

Climate change, the side-hustle version 263

Don’t look now, but you’ve got company! 265

The Biggies: Time, Money, and Fun 267

Time is — or isn’t — on your side 267

Checking the cash register 267

A great time was had by all 268

Roll with the Changes 268

Musical chairs 269

Addition by subtraction 270

Addition by addition 270

Turn Off the Lights, the Party’s Over 271

Cleaning out your closet 272

Saying your goodbyes 272

Tidying up the financial side 273

Chapter 15: Deciding What to Do If Your Side Hustle Gets Really Successful 275

Is Your Side Hustle Ready For the Big Time? 276

More time! 276

You have your money bases covered 277

Get me out of here! 278

Your Side-Hustle Business Plan, Take 2 279

Letting your brain storm again 280

Updating your side-hustle value chain 285

High hopes versus dashed dreams 286

Looking at Key Financial Considerations 287

Leaving No Going-Full-Time Stone Unturned 289

Part 4: The Part of Tens 291

Chapter 16: Ten Tips on Earning Passive Income from Your Side Hustle 293

Remember That “Passive” Does Not Mean “No Work Required” 294

Watch Out for Get-Rich-Quick Schemes 294

Recognize That Some Side Hustles Are Mislabeled as Passive Income 295

Know the Difference between Investment Ideas and Passive-Income Side Hustles 295

Pay Attention to Your Fans 296

Weather the Storm of a Failed Side Hustle 297

Find the Right Flavor of Passive-Income Side Hustle 297

Be Prepared for the Financial Ups and Downs of Passive-Income Side Hustles 298

Calculate Your Passive-Income Side-Hustle Life Span 299

Stack Your Passive-Income Side Hustles 300

Chapter 17: Ten Leading Gig Economy Platforms 301

Angi 302

Fiverr 302

FlexJobs 303

Freelancer 303

Guru 303

99designs 304

TaskRabbit 304

Toptal 304

Upwork 305

ZipRecruiter 305

Chapter 18: Ten Signs That You Need to Adjust Your Side-Hustle Strategy 307

You’re Not Making Any Money 307

You Don’t Have Enough Time 308

The Overall Environment Is Shifting 309

You Experience a Major Life Disruption 309

An Even Better Side Hustle Has Surfaced 310

A Key Supplier Can’t Deliver 310

You’ve Achieved Your Goals Sooner Than Planned 311

A Business Partner Has Let You Down 312

Your Early Test Phases Don’t Prove Out 313

You’re Not Happy 314

Index 315

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