12 Keys to Choosing and Building Your Best Side Hustle

There is a reason that January is a popular time to start a business. New Year, new you, fresh start, all that.

The good thing about a side hustle is that you don’t have to ring up a lot of financing to get started, and you don’t have to worry about all the paperwork and legalities of a big, full-time business. After all, it’s called a side hustle for a reason, because you’re making money on the side, outside of a traditional job or business.

When it comes to making extra income, one of the coolest and most profitable side hustles over the past few years has been reselling sneakers. Tales abound of sneakerheads boxing up profits by flipping Air Jordans at triple-digit margins.

We’re not talking here about memorabilia, like the pair of Air Jordans worn by none other than Michael Jordan that just sold for a record $2.2 million in April 2023, according to the auction house Sotheby’s.

We’re talking about athletic shoes that people collect not because some famous athlete wore them but because they are cool–and valuable. That particular side hustle has stubbed a toe. Supply has caught up to demand. Sneaker resale prices are down. Small operators who cannot compete at scale are closing shop.

For some sneakerheads who jumped into reselling with both shoes, the price slide provides a painful lesson in the importance of timing, planning and homework.

Side hustles beckon as ideal starting places for aspiring entrepreneurs with a business idea because they provide extra income, require only part-time labor and usually demand little investment. But that does not mean side hustles are easy paths to earning money online or putting extra cash in your pocket.

12 Things to Consider in Starting Side Hustles

Choosing and developing lucrative side hustles requires homework and forethought. The stakes and investment may prove lower, but choosing your side hustle is not that much different from choosing a full-fledged business idea.

It’s not just about asking what’s the No. 1 side hustle. Nor is it about asking which side hustle pays the most.

So, if you’re looking to turn your spare time (or a spare room) into extra cash, here are some important things to consider in starting side hustles:

1. Follow your heart, not just the extra money

Are you looking for something fun to do as a side hustle? Following your passion? Or just looking for more money?

Listen to your heart a bit. Tap into your creative and inventive self for your hustle ideas and you will find the energy you need to make money.

“You can’t use up creativity,” Maya Angelou said in a quote that has inspired many. “The more you use, the more you have.”

Choose side hustles that align with your passions and skills and the work will be more enjoyable. Your best chance at a successful side hustle will be doing something you love.

2. Go with what you know

Related to doing what you love is … doing what you know.

Think of how many people went after opportunities in cryptocurrency without really understanding crypto or researching whether crypto was a reliable vehicle for their own financial goals.

Whether you will be spending a few hours a week or all your free time, choose an area you feel confident in. And be able to explain what you do clearly, briefly and confidently.

“Your idea may be amazing, but a concept that is too big and complex to produce in the real world is a non-starter,” writes Wes Dening in this article on choosing a business idea. “Forget an elevator pitch; you should be able to explain your concept before those elevator doors even close.”

At the very least, a side hustle executed in familiar territory will help you improve your skills and show them off to the world even as you pursue that extra money.

As Georgi Todorov, founder of ThriveMyWay, put it in this article on top side hustles:

If you’re new to your industry and you need more experience to advance, doing a side hustle outside of your work hours can really help. It also applies if you’re trying to break into a specific industry and you don’t yet have a good enough portfolio to showcase your skills and experience.

A good portfolio makes you a much more attractive prospect for hire. So whether it’s future clients in your side hustle or hiring managers for your next job opportunity, you can’t go wrong with a strong portfolio.

Essentially, you can use your side hustle as a way to get more work done that’s going to help advance your career. While your day job might pay the bills, you need to devote some of your time to your future prospects so you can keep moving forward.

3. Don’t stay in the moment

Ask yourself whether your side hustle idea is tied to a market bubble. (Sneakers, anyone?) Or does it have staying power?

Too often, entrepreneurs can get caught up the excitement of an idea or rush to trust their instincts and just get going. That energy is a key element of success, including for side hustlers who want to get paid beyond a full-time job.

But diving in to a fad puts your side hustles at risk if you have failed to do your homework.

Look beyond the flavors of the moment or any fleeting “top 10 side hustles” list for your extra money. If your side hustle ideas have the feel of “here today, gone tomorrow,” be wary.

4. Address consumer needs, get paid

Is your side hustle addressing a consumer need? Be ruthless in assessing whether people really need or want what you have to offer.

You can do all the business planning and social media management you like, but if no one wants what you are offering, you will find yourself left with only your full-time job in just a few months.

On the other hand, if your side hustle is addressing a consumer need, may find yourself facing the opposite question: Whether it’s time to abandon your day job and and invest yourself in your hustle job for your full-time income. At that point, will have to assess whether your side hustle is scalable and whether you can grow your business—freelance writing, pet sitting, what have you—into a high paying, full time gig.


Related: Best Web Hosting for Growing Your Side Hustle into a Small Business


For good advice on that question—when a fun side hustle becomes more than a side hustle—see this first-person account from Luisa Zhou.

She built her side hustle social media consulting business into six figures, ultimately allowing her to turn her side hustle into a full-time job.

“I didn’t hand in my notice before I was sure my business would work in the long run and I had plenty of people lined up to work with me,” Zhou said. “The biggest reason you won’t have to take on external funding is your day job, so stay at it until you’re making at least two times what you’re making in your 9-5. Financial stress can ruin your business, so making enough money in your side business is one of the most important things you can do for yourself and your business.”

5. Solve people’s problems, also get paid

A cousin to whether side hustles address a consumer need is this: Does your side hustle idea solve a problem? If your side hustle does that, you are on your way to positive income.

And when we say solving problems, that can mean merely helping another person or a business or an institution become more efficient.

If a local school has a calendar of online courses, for example, but lacks staff to produce them all, your expertise in that subject matter could help solve that problem. Or maybe your neighborhood association has a problem with icy sidewalks. Your snow shoveling abilities can help solve that problem and provide you with good money.

Best of all, learning how to solve problems with side hustles is a way many business owners got their start. Simple supplemental income ideas can lead to bigger things–and a much bigger bank account–down the road.


Most read: What’s the Average Income of a Subway Restaurant Franchise Owner?


Ryan Robinson presented the problem-solving component in a compelling way in this article about best side hustles:

Start by asking yourself these questions to examine whether or not there’s a market for solutions to the problems you’re good at solving.

Are there any particular problems or topic areas that people tend to come to you asking for advice and assistance with?

Are you seen as a resource or a resident expert at something?

Do you find yourself answering the same questions over and over again in the office?

Is it easy for you to connect people you know to others who are good potential customers, partners, investors or otherwise?

Have you built your own internal tools or processes for doing something quicker?

Do you have a coveted skill that seems difficult for others to build and replicate?

6. Competing side hustlers

What’s the competition? Whether it’s freelance writing or a dog walking service or pet sitting, keep in mind that you will be fighting over the decent cash with other side hustlers.

Take a look at the Facebook Marketplace, for example, to see who else is out there trying to pick up a few extra bucks.

The space for your side hustle may be crowded–just look at the dropshipping business–but if it’s a huge market, you still may be able to find clients and decent money.

7. Spare time vs more money

Do you really have the time? Can you be successful doing your idea as a side gig for a few hours a week, or would you need to perform it as a full-time job to get paid the way you want?

Just as important, is the type of work you want to do for your side hustle inherently flexible?

Keep your full-time job in mind as you look for side hustles that offer flexibility in terms of when and where you work for that extra income. Try to be as honest as possible about any lifestyle choice your side hustle might demand. And try to go slow at the start so your side hustle doesn’t become just a side hassle.

8. Side hustles can go wrong

Assess the risks.

Yes, we are talking about side hustle ideas here, not major investments with hefty start-up costs and more money going out than extra money coming in. But anytime you want to run your own business—and a side hustle is your own business, if only smaller—you will be running some risks.

Maybe that risk is throwing good money after a bad idea. Maybe your side gig imperils your high paying job. Maybe the risk is taking too much time away from the fun things you like to do and the fun people you love. Maybe there is a legal or reputational risk.

That spare room might present an opportunity for extra cash, for example, but renting to strangers can be complicated.

9. More to digital than making money online

You don’t have to do anything fancy right away. In fact, don’t fall into the trap of creating digital assets for a side hustle that doesn’t even exist yet as an online business.

But do start thinking about what you want your online presence to be. Eventually, even some basic digital marketing practices and social media management will come into play.

The best side hustle jobs don’t even need to be an online business, of course. You probably won’t need to test your ideas out on a focus group, at least not in the early stages. You may not need to conduct online surveys or hire social media consultants.

But digital marketing will likely play a role in some way, even if it is only posting about your garage sales or personal training or dog sitting services on a neighborhood website.

Decide what you want your social media profile to be, whether you want an online store and how much you want to spend to earn points with digital consumers.

10. Side hustles demand research

Even beyond looking at the competition (see No. 6 above) and assessing the risks (see No. 8), you must find out ahead of time whether your side hustle will require any licenses or permits from governmental agencies, whether that’s at the federal, state or local level.

If you’re making more money with passive income, how does that affect your taxes? What are the terms and conditions of any platforms you might use to sell your goods, get paid or deliver packages?

Unless you are setting up a bookkeeping business, then the business of bookkeeping might be new to you.

Maybe take an online course in your spare time to fill in your knowledge gaps.

11. Speaking of this bookkeeping business

Yes, yes, this is a side hustle. Your side hustle. You are not running Apple.

But your side hustle is your own business, and you need to not only make money but also account for the hustle expenses as well as the hustle income.

If you want a profitable side hustle, keep track of every penny of extra cash you get paid and every penny you pay out. And do this from the moment you start a side hustle.

At some point, whether it’s after a few months or a full year, all side hustlers have to ask whether the extra money is worth the extra effort. Or should they just bag the side income.

Having all your expenses and positive income counted up in front of you will tell you whether you have a profitable side hustle and help you make that decision.

12. Get inspired. Stay inspired.

Look, you’re going to have days. Good side hustle days. Bad side hustle days. Days that are high paying and then days when you wonder whether there is any such thing as positive income.

A dog walking business? Whose bright side hustle idea was that?

So, when the bad side hustle days come, you will need to draw on some inspiration to keep going with your online tutoring or pet setting or dropshipping business.

Here, then, is a great list of books aimed at informing, guiding and inspiring you in your Great Side Hustle Quest.

Remember, you’re starting a side hustle not just to create some passive income or make money online. So don’t let your bank account be your only inspiration.

Conclusion

Following all 12 of these things to keep in mind when starting side hustles doesn’t guarantee success. If there were guarantees in business, or in life, there probably would not be so many entrepreneurs as there are.

But follow this guidance and at least you will have a sound basis for getting started on your side hustle.

And on the flip side? Not taking the time to vet your side hustle ideas, put together a plan and do your homework will definitely raise your risk of failure.

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  1. “Go with what you know” is very important! I see people ALL THE TIME who want to chase a new, shiny thing (crypto, AI, etc.), but they don’t have any relevant experience in it. There’s much less brain damage when you are creating something that is familiar to you from your experience.

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