Side Hustle Table of Contents

The Side Hustler’s Handbook

The rise of the YouEconomy wasn’t born only of a certain generation’s unwillingness to follow the status quo.

It wasn’t born only of the Great Recession, either.

You’ve heard tales of the changing work and economic landscape—the rise of the freelancer. What was once the storied pickle-jar-tip life of the determined musician has become the norm for 35% of working Americans, according to an annual study conducted by Upwork.

What it means to participate in the YouEconomy is up for debate, and that number might not include those who are seasonal workers, neighborhood side-hustle owners, direct sellers and occasional freelancers. The side hustle has become a way for full-time employees to stretch their creative muscles, test new products or fund annual vacations without sacrificing the security of traditional employment.

The main benefits of having a side gig, of course, reside in flexibility, virtually limitless earning potential and the satisfying feeling of being your own boss, even for just an hour or two a day. But what is the price of that freedom?

This article doesn’t cover the history or the scope of side hustles or why, more than a decade after the term became popular, it continues to be the primary way most people first dip their toes into the YouEconomy. That’s not new information. What we will offer is a set of ground rules for you to consider as you embark on an adventure that could—and should—alter the way you view business, income, free time and success. We’ll also share some advice from those who have made it their life’s work to help people thrive in this new economy. They’ll be the first to tell you that, no matter the size of your side hustle, you should be prepared to work hard, show some grit and get creative when problems arise.

Perhaps the greatest contradiction to this story is that choosing the “other” option for your life means abandoning the time-worn handbook, the rules we are supposed to follow as workers, and stepping into freedom and uncertainty. Opting for the red pill means casting aside any previously held beliefs and keeping an open mind. It’s probably nothing like the lessons you learned in your career exploration courses in college or high school, and you’ll have to turn a deaf ear to the well-meaning friends who advise a more conventional route.

A side hustle can be as small as driving for Uber a few hours a week, or as big as the creation of a new product that scales into your main source of income. The key to success is to understand your motivations, your strengths and where you want to see it go.

Below are the unofficial laws of the side hustle, taken from those on the front lines.

Law #1: Understand that there are numerous paths to the same finish line.

Just because you have 10 friends who make extra income walking dogs in their neighborhood doesn’t mean it’s the right option for you.

If your motivation is earning additional income, that shouldn’t come at the cost of doing something you don’t find enjoyable. Even worse, don’t be tempted to sacrifice the better option for the easier option. Instead, take time to think through your set of skills and what you enjoy doing in your free time. Be stubborn in the pursuit of your dreams, but be flexible in how you get there.

Law #2: Be selfish, but understand that it’s not all about you.

Selfish, in this sense, means putting yourself and your needs above the needs of the person issuing your paycheck. What would you do if money were no object? Images of remote islands with fruity drinks and no emails might spring to mind. And sure, this would be fun for a few days or even weeks, but what about after that? Maybe you dream of creating something that brings you riches and fame. What about after all of that?

The point here is that in the end, most of us don’t want a life that revolves only around ourselves. The best side hustles, both practically and in terms of fulfillment, are ones that add value to other people, that change the world in some capacity.

Law #3: Remember that your side gig can help your day job, and vice versa.

Although the number of traditionally employed people with side hustles continues to increase, just as many feel uncomfortable talking about their side hustles with coworkers. They might even downplay the idea as “just this little thing I’m working on,” as if their side hustle somehow means they don’t care or are less invested in their main jobs. For many, though, having a side gig bolsters their resume rather than detracting from it.

For example, if you work in technology and build an app on the side, those skill increases will often translate into your main job. Another example: You are a marketing leader for a national company and you just sold a book on the side.

“You are not your job,” says Susie Moore, a New York-based author and career coach. “Your job is one part of your multi-faceted, potential-filled self.”

One more thing to keep in mind: Many companies offer continuing education benefits in the form of funds to allocate toward classes, conventions and workshops. Get creative and find some resources that can benefit both your job and your side hustle.

Law #4: Just make sure that your side gig doesn’t cost you your day job.

We’re breaking society’s rules about how employment is supposed to work here—not your company’s actual rules.

If your company has non-compete clauses or specific language about outside business ventures, make sure that you’re not violating them. Although you’re typically not required to divulge a side hustle to your employer, it can sometimes mean additional support and flexibility within your primary job.

Law #5: Be ruthless with your schedule.

This is not the time to daydream about your side hustle while slacking off on your employee duties. When you’re at work, be at work; when you’re working on your side hustle, be there too.

Moore advises her clients to use the fringes of time between appointments and during commutes to respond to quick emails, type out a few notes or schedule some appointments. If you have three minutes to wait on your train, ditch the Instagram scroll for a quick burst of productivity.

Law #6: Adopt a side-hustle mindset within your traditional job.

Your side hustle is exciting. You’re focused on maximizing your time, staying efficient and prioritizing the things you value. You have fully embraced a mindset of growth and innovation. But who are you at your day job? What if you translated some of that ownership and personal responsibility into your full-time position? You might find that you have more autonomy in your 9-to-5 than you once thought. Consider sitting down with your supervisor to discuss ways to eliminate needless meetings, reduce time-sucking email threads and increase time for creative thought.

Law #7: Harness your fear.

Being afraid is inevitable when going it alone. It’s a natural response to change and unknown environments. But fear has no place in the side gig world. It can cripple you faster than anything.

Launching a business of any size is risky. You risk your time, your energy and probably some money. But you’re playing for something more: the chance to gain happiness, significance, financial security and independence… the chance to gain success.

Diane Mulcahy, author of The Gig Economy: The Complete Guide to Getting Better Work, Taking More Time Off, and Financing the Life You Want, advises writing down your worst-case scenarios and then, if they are even slightly reasonable fears, creating a plan to avoid them. An example: No one will care about my product or service. That’s a possibility. To quiet that fear, focus on bolstering your personal and professional network. Gather 10 people from that network and conduct an informal product test.

Law #8: Never work for free, but understand that payment isn’t always monetary.

You didn’t start this side hustle out of thin air. You already possess some knowledge or skills that pertain to your product or service. If you’re promoting yourself as a photographer, you have probably used a camera before, and you’ve hopefully been told that you have an eye for framing. Maybe you’ve even been asked to take some engagement photos by a friend.

The point is, you are already equipped with a set of skills that not everyone possesses. You should be compensated fairly for those skills. But if you’re in the very beginning stages of your side hustle, consider asking for testimonials or referrals as a form of payment while you build your brand and reputation.

Law #9: Seek originality, but know that it is not necessary.

“What we perceive as original is often just a rearrangement of what has come before,” writes Jeff Goins in Real Artists Don’t Starve: Timeless Strategies for Thriving in the New Creative Age.

A popular excuse among would-be entrepreneurs is that it’s been done before. That’s true, but it hasn’t been done by you. Some of the best creators have spent years studying and mimicking others in their field, including author Stephen King and renowned dance choreographer Twyla Tharp. After you perfect the art of mimicking, the natural progression is to add what’s uniquely yours, which is the accumulation of your experiences, personality and worldview.

Law #10: Tackle procrastination—it is negativity in disguise.

Side gigs are a risk, even with countless hours of research and planning. We devote all our spare attention to this interest that might fail, and in doing so, we forfeit the opportunity to devote attention to other interests. This idea is a procrastination technique that Moore hears constantly.

“Just because you launch something doesn’t mean you’re handcuffed to it for life,” she says. “All businesses evolve and change over time.”

Procrastination techniques might sound like thoughtful analysis of a risky bet, but if we listen to that negative voice, we’ll never start anything.

Law #11: Don’t try to be an expert at everything.

You’re like Liam Neeson (in some ways!): You have a very particular set of skills.

You likely launched this side gig because you have a certain talent, interest or experience for this type of work. But problems will arise when you have to take on 15 other hustle-related tasks that aren’t in your natural wheelhouse. If you’re not turning a large enough profit to outsource these, it seems the only option is to complete the tasks yourself. That can be a fallacy.

If you need a portfolio website, for example, consider what’s truly more expensive: spending countless hours learning how to build a website or investing a one-time fee to have an expert build a simple, clean website that displays your offerings.

Law #12: Don’t make business more complicated than it needs to be.

No amount of preparation will leave you feeling prepared to launch your side hustle, no matter the size or scope of your endeavor. You might think that, because you don’t have a business degree or a decade of experience in the corporate world, you’re ill-equipped as a business owner.

“If you’re going on a road trip across the country, you don’t need to know every single stop sign; you just have to see a little bit further ahead,” Moore says. “Business isn’t complicated. It’s a margin. Are you making money and are you happy with how much you are making for how much work you’re doing?”

Law #13: Be prepared to break the rules.

Fast-forward six months. You have a fledgling side hustle as well as your traditional office day job.

Maybe you’re making enough money to fund a vacation or cover the majority of your mortgage payment. Maybe you’re only making enough to cover groceries. You’re working a lot, and for the most part, it’s still enjoyable. But then you come home from a long day to find an upset client from your side gig. Your brain is already fatigued and now you’re asking yourself, Why am I doing this? Is this worth it?

It’s in these moments that you need to evaluate your situation. Are you just having a rough day or has this side hustle started to bring you down? Remember, the point of a side gig is not to add more stress to your life, but rather to offer a creative outlet, bring in some supplementary income and bolster your life resume. Don’t be afraid to let go of something that no longer serves you. This is the YouEconomy, and it’s endlessly customizable.

But let’s say you’re six months in and your side hustle has really taken off. There’s fairly common advice from YouEconomy experts about when to make the leap from double-duty to focusing 100% on what started as your side hustle: The instant it’s making you more money than your day job.

The idea goes that your side business will benefit from having all of you—all of your skills, effort and attention—rather than sharing you with your employer. And that’s probably true. But you should know your business well enough to have an idea of how far it can actually scale. You should know yourself well enough to have an idea of how long you can keep up a day job while also building your own business. Maybe you like the work you do for your traditional employer, and love the people you work with.

Again: This is the YouEconomy, and it’s endlessly customizable.

Do what works for you.

Avoid the Side Hustler’s Paradoxes

Going it alone with a side gig is intended to bring us happiness, fulfillment and supplemental income, among other things. But these things come at a cost.

After all, you’re balancing a full-time job with a business that could always benefit from more of your focus and time. We address three of these paradoxes with Moore, career coach and author of What If It Does Work Out? How a Side Hustle Can Change Your Life.

Brand awareness vs. maintaining your mental health

Consider the types of side gigs where you might have to promote yourself to secure more and higher-quality gigs. Brand awareness is key. It also opens you up to a constant stream of feedback, which is necessary.

But with that necessary feedback often comes cruel comments and useless negativity. Social media has been proven time and again to increase feelings of low self-worth and diminish creativity. How do you balance the two?

“What is more important?” Moore says. “Is it the fact that you want to hide, or the fact that you really want to make this and you want people to see it?

“Create without any expected outcome—just with the intention of doing something valuable that feels real to you. As Brené Brown says, unless someone is in the arena doing work like me, I don’t care what you have to say.”

Limitless growth potential vs. life balance

In the YouEconomy, there can always be more clients, bigger growth, more productivity. Your side hustle is supposed to bring you happiness and fulfillment, but how do you keep that from becoming an unhealthy addiction?

“If it’s just you creating whatever it is that you create, there is going to be a cap on that,” Moore says. “But I know plenty of side hustlers who are really happy with that cap. Set an intention: How much money do I want to make? Most people don’t do that. They think it has to keep growing; it has to get bigger. Bigger can be better in some cases, but not always.

“However, if you want to scale and grow, you probably need resources and help. People tend to ask for help quite late.”

Favors vs. paychecks

As an entrepreneur, you and your brand are linked. This merged identity can open the door to blurred relationships between friends and potential clients. When anyone can be a client, what does it mean to be yourself? Where is the line between a friend asking for a favor and a client?

“You’ve probably been side hustling for free in some capacity for a long time without knowing it,” Moore says. “It’s what gives us the confidence in the beginning to get going.

“If you’re trying to build a brand, offer a price that feels reasonable, such as a special launch price. Then give it an expiration date… Not everyone can do [what you do]. Appreciate your talents and appreciate yourself.”

8 Side Hustles You Haven’t Heard 1,000 Other People Doing

1. Listening services

Basically an unbiased friend-for-hire.

2. Errand runner 

For the elderly or home-confined.

3. Garden consultant

Because not everyone wants to hire an expensive landscaper.

4. Live insect wholesales 

For reptile owners; this business brings in $15,000 per month for Jeff Neal, founder of TheCritterDepot.com.

5. Snack organizer 

Richard Foulkes, founder of JensSweetShop.com, runs this business providing customizable treat boxes in the evening hours after his day job.

6. Private security

An appealing option for veterans or those in the public service industry.

7. Flipping antiques or collectibles

Buy low, sell high.

8. Breakup coach 

This niche therapy category allows Chelsea Trescott, founder of Breakupward, to work with clients all around the world.

You Can Start Today!

Direct sales offers side-hustling’s lowest barrier of entry.

So you may be reading all of this and thinking, sounds good, I’d like more money and a chance to stretch myself. And at the same time, you might also be thinking, but… I can’t code. My writing isn’t great. I’m no artist.

We hear you. And this is where direct selling might make sense. Because you need no highly-developed or special skills in direct selling (also known as network marketing or social selling), you may be equipped to succeed immediately based on nothing more than your desire, determination, drive and willingness to grow in something new.

Here’s how it works: Companies that operate on a direct selling model provide products and services backed by research, funding and fully-formed marketing systems to side-hustlers who are excited to try their own thing. The individual entrepreneur has constant access to the marketing, support and technical resources of the company providing the products or services.

Direct selling is one of the industries that best leverages social media to market and even sell, making the financial cost of getting started minimal. Many direct sellers say the low-cost, easy-to-learn and supportive systems are reminiscent of joining a family business. If you are intrigued by the idea of starting up a proven side hustle, ask someone you know who’s already in direct selling to show you how they got started.

“There are some steps in between desire and riches, but you begin with the desire,” the iconic motivational speaker and author Jim Rohn, who got his start in direct selling, once said. “[Direct selling] is a chance to turn pennies into a fortune, a chance to turn nothing into something.”

“There are some steps in between desire and riches, but you begin with the desire,” the iconic motivational speaker and author Jim Rohn, who got his start in direct selling, once said. “[Direct selling] is a chance to turn pennies into a fortune, a chance to turn nothing into something.”

What Type of Hustle Is Right for You?

The below questions address your work style and motivations. Circle the answers that best resonate with you. At the end, your scores will be represented by how many a’s, b’s or c’s you circled. There are no right or wrong answers here. This is the time to explore the scenarios where you work best and determine how you want to join the Gig Economy.

This article originally appeared in the Fall 2019 issue of SUCCESS magazine and has been updated. Photo by Shutterstock